This week’s love goes out to this simple illustration that made my LinkedIn feed brighter this week.

Image credit: Posted by Salman Hashmi - LinkedIn

I love when things are so simply explained by a picture that are so complex when people describe them with words. This is the most underrated skill in project management! If you work on one thing for the rest of the year make it drawing better illustrations!

From the Practice

This week I’m highlighting the intersection of several pieces I came across around one of the hottest topics in our practice at the moment: AI projects.

First, a very interesting piece from McKinsey Quarterly on where AI will create value and where it won’t. As of late 2025, nine in ten companies had deployed some AI within at least one business function, but 94% reported a lack of value from those implementations. However, the McKinsey team points out that most of these implementations were productivity focused and basic economic theory teaches us that if everyone is doing it, no one is reaping a reward.

Any good project manager knows that those questions get asked during project discovery or pre-project work as the business case for the project is shaped and the project charter is created.

Price Waterhouse Coopers annual CEO survey found CEOs were almost as likely to report additional earnings from AI (26%) as additional costs (22%). Only one in eight CEOs reported both higher earnings and lowered costs.

The McKinsey team found three core areas where AI steadily added competitive advantage:

• proprietary data, especially where this improved performance over time

• AI beneficially embedded into customer workflows that reduced incentives to switch products

• faster iterative learning

Price Waterhouse Coopers reported the most common areas CEOs were making AI investments in were:

• demand generation (22%)

• support services (20%)

• customer offerings (e.g. products, services, experiences) (19%)

• strategic direction (15%)

• fulfillment (14%)

There is an obvious misalignment between those two findings that every project manager should note; and in doing so, it should then not come as a surprise that Gartner found 40% of agentic AI projects will be canceled by 2027. What might surprise you is that Gartner reported that statistic in 2025. The reasons for cancelation? Escalating costs, unclear business value, and/or inadequate risk controls.

If we just stop for a moment and reflect on this, we can see that in fact this is a lack of control or direction period. If we’d been fleshing out the business case properly we’d have never got started. If we’d chartered these projects properly we’d have never gotten started.

Margareth Fabiola S. Carneiro a PMI Fellow points at a key gap:

Margareth goes on to point out that many project managers have focused on AI adoption, not the management of AI projects. In fact, less than 1000 people have completed the new PMI-CPMAI® credential. And maybe like me you were a little skeptical at first about this new certification.

But on closer examination, the curriculum covers everything you need to know about data, model development, business cases, and implementation; even designing metrics to measure success. And you can learn more about the Cognitive Project Management in AI methodology for free from PMI’s website. PMI members can also access a Practice Guide for free.

So Margareth and I are rethinking an investment in the PMI-CPMAI credential, and maybe you should too.

The writing is on the wall that project managers who master these competencies will become critical assets to every organization. Generalist PMs with big picture thinking, the ability to see through complexity, and strong collaborative problem-solving skills who invest in skills to manage AI projects will become the superheroes of the next decade.

An interesting read

As Q2 is off to the races, we are entering the season where many project managers feel a time crunch. School is about to let out. Summer vacations are about to need space. Meanwhile, the project just keeps needing attention and the juggle is real.

So this week’s interesting read is a thought-provoking read (or watch) of an interview by Jeremy Caplan (a.k.a. author of Wonder Tools) of Laura Vanderkam author of several books (most recently “Big Time”) on how to make the most of time.

I’m going to be honest and say that this article stopped me in my tracks, which is rare.

I think of myself as a person who uses time impactfully. And now I’m rethinking if I can make it even more powerful.

I’d love to hear how this landed with you. What’s one thing you might consider changing after reading it?

Leave a comment

A tip

Next week something exciting is happening for women in project management:

PMI Poland Chapter is hosting their first international conference for women in projects.

Held in English and 100% virtual, conference topics include: leadership, soft skills, resilience, sisterhood, barriers women face in career development, elements of AI, and the ability to navigate technological and social change.

The agenda includes presentations from outstanding speakers from Europe - practitioners who not only share knowledge, but also inspire and demonstrate how to turn it into real action. Participants can expect a solid dose of expertise, fresh perspectives, and experiences from different industries and cultures. Among them are keynote speaker Bruno Morgante and speakers Yasmina Khelifi, Laura Neuwirth, and Liz Hector.

Register here.

A lesson

This week’s lesson is about something PMI-CPMAI isn’t going to teach you: “the meta-skill of reading context”. For most generalists, this is instinctive but unrefined. In a recent article John Cutler suggests that if you invest in refining this meta-skill, you might just blow the AI playbook wide-open in every organization you touch.

This is a journey that is not for the faint of heart. John points out something we are all feeling and not saying:

So how can we navigate the journey?

In short, generalists are poised to travel this road more easily and more quickly than others because our natural adaptive learning style means we are often comfortable with the kind of ambiguity we will encounter and we’re ok to just see it through and learn along the way. This is a lesson we can practice. It is also a lesson we can teach. Both will be tremendously valuable to the future ahead.

This week I’m loving

If like me you’re taking stock and feeling like you need to refocus, I’m throwing back to a segment I wrote in only the second issue of this newsletter that is still a truly brilliant framework for how we manage our own personal effectiveness.

Practical and actionable advice from the wonderful Kathryn Montbriand about the real-life juggle of a generalist.

In her article, published for Generalist World, Kathryn described the “plight” of the generalist as “we can do anything…so sometimes we do everything.” I’m sure for you this strikes a chord as it does for me. However, the answer that the world gives us for this problem, is usually delegate, take on less, focus. How good are we at this?

Enter, the mental model of the stovetop. Your value is finite. You can only spread yourself so thin before you’ve dispersed your energy across too many things. The stovetop has capacity for 4 pots. Try to cook more than 4 pots and there isn’t enough heat. The burners are different sizes and this represents the energy you can invest in each of the things. I don’t know about you, but I loved this visualization. Just like cooking on a stove, you can dial-up and dial-down the energy you put into the 4 pots.

The beauty of this mental model at first glance is in its simplicity. However, what I also loved is that it simplifies a tough scenario we generalists encounter often: the need to give up on something. If you use this model correctly, firstly, choices might be simplified by focusing on the impact you can make with your valuable energy. This might make it easier to select the 4 pots. Secondly, you don’t have to feel that you must give up on something when other things are competing. You can dial-down the energy on something to dial-up somewhere else, and the 4 pots can stay on the stove.

It’s a mental win-win.

Kathryn goes on to provide practical advice about how to use this model combined with quarterly planning and objectives. I recommend you read the full article if you are inspired to try this.

From the Practice

I’m looking ahead to so many exciting things that are coming into view for the rest of 2026. Speaking engagements, working with women in project-oriented roles and entrepreneurship, and rebuilding my consulting practice. I’m feeling new levels of clarity as a generalist PM and as a consultant and this week I put that clarity onto paper (I think).

If you are working in an environment where taking stock as we enter Q2 has raised a lot of red flags about progress to date, a root cause you might need to examine is value alignment. Misaligned work can be a tremendous cost. I’ve put my approach for assessing your value alignment down into two tools that I released for free this past week.

If you are questioning whether your project is aligned properly with strategy, I’ve developed a checklist that will help you score your project’s alignment to strategy.

Download the checklist here.

If you use this tool, I’d love to hear your feedback!

The second tool is to support assessing alignment with strategy at the organizational level. For this, I’ve developed a guidebook which will help someone in your organization facilitate a session with a cross-cutting team to examine everything you are executing and figure out what you can prune to refocus. If this sounds more like what your organization might need, you can get your copy of the guidebook for free here.

An interesting read

I think we can feel the volatility of the world growing under our feet causing us to feel uncertainty everywhere as we look ahead to the rest of 2026. I wanted to throw back to a great read I featured in September of 2023 that feels like we might want to remind ourselves of it for the road ahead.

Judgement; the ability to form an opinion objectively, with authority and wisdom, is a critical skill used often by project managers.

It involves the ability to combine personal skills and experience, with information from the environment and team to define a course of action. We use it commonly in project planning, but as you become more experienced, also in project definition and project oversight. Some people believe it may be a key quality of exemplary leadership.

Cultivating so called “expert judgement” - the project manager’s secret sauce - can be a daunting task of trial and error. Especially if you are practicing as a lone wolf.

This week’s read is a great article featured in Harvard Business Review which discusses the elements of good judgement and how to improve this competency as a leader.

The article breaks good judgement down into six components:

• Learning

• Trust

• Experience

• Detachment

• Options

• Delivery

There are many great stories and highlights in the article so I really hope you enjoy reading it. However, I wanted to feature a couple of important concepts that speak specifically to good judgement as a generalist skill.

First - the article cautions that deep expertise can cause us to get comfortable in a decision-making rut. This can bias our judgement. However, as generalists often don’t seek out or need to exercise their deep expertise, this may make us better at the practice of expert judgement in project management.

Second - leaders with good judgement are experts at synthesizing information. This includes processing both written and oral information at a high level of comprehension. In short

…leaders with good judgment tend to be good listeners and readers—able to hear what other people actually mean, and thus able to see patterns that others do not. They have a breadth of experiences and relationships that enable them to recognize parallels or analogies that others miss…

I don’t know about you but patterns other people can’t see are the essence of generalist existence.

If you read the article - I’d love to hear what you thought.

Leave a comment

A tip

My friend Raquel Horta brought up a great insight this past week. If you’ve been feeling like your meetings go great and you have alignment on everything but nothing is getting done, maybe check if you have accidentally mistaken agreement for commitment.

Image credit: Raquel Horta - LinkedIn

A lesson

Finally, a reminder I have been feeling deeply this past week which I hope is valuable to you, first written in the April 19, 2024 issue:

Insight is a secret skill of Generalist PMs because the definition of an insight is “the capacity to gain an accurate and deep intuitive understanding of a person or a thing.” This requires emotional intelligence, the ability to see details while understanding a big picture, and the ability to combine knowledge and information in situations of complexity. These are core skills for a Generalist PM.

Strategy guru Alex Smith says:

Why? Because strategy success comes from having an understanding or knowledge that is different or unknown in comparison to your competitors.

How do you tap into your ability to generate insights?

Here’s some ideas:

1. What are the things you know about your organization, and/or know how to do, that are unique to you? (These are your secrets which are a form of insight).

2. What are the things that you feel are obvious but which others don’t seem to notice? (This is your unique ability to see through complexity that gets in the way for others. This is a form of insight).

3. What gaps can you see that are causing problems or failures in the systems in your organizations? (You’d be surprised that most people can’t see these and so they are unique insights you can offer).

4. What steps can you see on the pathway ahead that no one is talking about? (Your ability to breakdown a mission into an actionable process is your project management superpower, don’t assume everyone knows how to do this).

You might think that you don’t have insights, but I assure you that you do. Tapping into these is a powerful offering to any organization you work for. I’ll close out with some wisdom from Alex:

This week I’m loving

This week’s love goes out to Timothy Tiryaki for a solid perspective on culture in organizations.

Image credit: Timothy Timur Tiryaki - LinkedIn

One of the best parts about this model is it acknowledges that culture feels different for different groups or perspectives within your organization. This, in my experience, is extremely important to understanding culture dynamics.

I deeply appreciate the recognition that culture is the operational fabric of an organization: i.e. it has a direct influence on delivering value. Centering this on decision-making is a really important aspect of understanding if operational culture is serving the needs of strategic execution.

Finally, acknowledging the gap between inspirational culture and lived experience is a key callout informing cultural work and improvement in an organization. The idea that leaders need to be capable of seeing culture from all the lenses is also extremely important. It gives a valuable insight into why culture transformation often fails. Since many culture transformations are undertaken as an improvement in lived or operational experience but not in leadership of culture.

If you are leading transformation work right now, does this resonate?

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From the Practice

This past Wednesday was Earth Day, and the Project Management Institute quietly released the latest version (Version 4) of their Practice Guide for Sustainability in Project Management (goes along with the PMI® GPM® credential). PMI members can get the guide free here.

Today, I wanted to highlight, one little gem from within the guide that might be useful to a lot of you: the PRiSM Project Life Cycle.

Image credit: Project Management Institute - Practice Guide for Sustainability in Project Management (Version 4) April 2026.

PRiSM (Projects integrating Sustainable Methods) is the life cycle developed by GPM Global (Green Project Management) in 2013. PMI and GPM have had a strategic partnership to improve the integration of sustainability in project management since 2022. I’m sure it is not lost on you that this “standard project life cycle” features some key areas that many have argued should be in PMI’s “standard project life cycle” for many years. In particular the “Pre-project” phase which I also appreciate in DSDM (Agile Business Consortium) and the direct connection of Authorization and Benefits Realization as components of the expected “life of the project”.

This life cycle is further strengthened by defined business case development during the pre-project phase (something I have long advocated for by requiring it ahead of drafting a project charter); rolling planning throughout the life cycle (e.g. the closure phase is planned during the delivery phase); and a responsibility of the project team for a “Benefits Realization Plan”.

I can’t count the number of teams I have worked with who had a “Discovery Phase” in their project life cycle and now this is legitimized with a series of activities crucial to shaping this part of a project.

Another interesting tidbit is the framework for Project Success criteria. You’ll recognize the base triangle but check out the addition in the center of the triangle!

Image credit: Project Management Institute - Practice Guide for Sustainability in Project Management (Version 4) April 2026.

We often see Quality show up in the center of the triangle but the practice guide points out that Quality is really a roll-up into overall Stakeholder satisfaction and not a category on its own. This is because the perception of Quality is driven by stakeholder expectations.

What I really like about this framework is often sustainability solutions are at a cost trade-off and so the traditional triangle penalizes them. In this version, stakeholder interests that benefit from a costly solution are considered in the frame.

One final little gem from my read through is the discussion around value drivers, and in particular, this diagram showing a visual way to map these.

Image credit: Project Management Institute - Practice Guide for Sustainability in Project Management (Version 4) April 2026.

I think this makes centering around value in early project discussions so straight forward and I’m excited to try it out with a team very soon!

If you checked out the Practice Guide, leave your thoughts and insights for others here:

Leave a comment

An interesting read

This week’s interesting read raises an important question for every project manager to consider: how is decision-making going in your organization? Specifically, executive decision-making — the strategic kind.

Author Fola F. Alabi shares some common challenges organizations are encountering:

• Accelerated decision timelines

• Incomplete information to make decisions

• Increasing precision for outcomes

Fundamentally the gap between strategy and execution is widening.

A key weakness is planning for value, and specifically how to measure value over time. The realization of value following delivery isn’t immediate. Organizations need to consider both short-term and long-term evidence and be prepared for the differences in these assessments.

Strategic execution is a collaboration between visionary and executor. But a lot of our efforts focus on the optimization of execution without considering the gaps in vision. Further, most organizations separate these two functions with minimal opportunity for collaboration.

A critical gap is the lack of ability to incorporate “execution intelligence” (that is knowledge about how to execute, how execution will likely go, execution tradeoffs etc) into strategic decision-making.

The solution? Shared responsibility.

Three non-negotiables driving the solution:

1. Define value before any resources are committed.

2. Use dashboards to measure outcomes not activity.

3. Create transparency between strategy and execution.

A tip

PMI has released the updated study materials supporting candidates writing their PMP exam from July 9, 2026 onwards. This includes PMI Study Hall subscription which combines refreshers with question, mini-exams, and full-length simulations available across desktop and mobile. Subscriptions start at $59USD for 3 months of access.

A lesson

This week’s lesson is a ship themed tale by Tom Geraghty. A story that despite my marine interests I had not heard before! The story of the Vasa Disaster. There’s a museum in Stockholm, Sweden, that houses this best-preserved 17th century ship after she was rescued in 1961 from her watery grave of 350 years.

The construction of the Vasa is a lesson in all things not to do on a project. Shifting requirements, a lack of construction standards, scope creep, poor communication, and a change in project leadership part way through construction.

A key dynamic that resulted in the tragedy was a dramatic power differential.

The lesson is an illustration in the reasons why psychological safety is a critical component in managing organizational risk.

This week’s love goes out to Ash Maurya for his reminder to be aware of our assumptions. It begins with the simple statement:

And this is true.

But it is also true that every project is a bundle of assumptions. That’s why in every project charter I write, there’s a whole section devoted to Assumptions.

Ash recommends a thorough practice, not unlike risk identification, to identify assumptions. He shows how this can be done using a Lean Canvas.

Image credit: Ash Maurya - LinkedIn

This tool also works for projects and the process can be applied in the same way.

Many project teams struggle to figure out the right order to deliver things in. I find, in fact, that teams will address this by delivering the easiest things first even though the hard things are what take the most time. This is your number one reason for a sliding schedule BTW! Ash shares my concern in his context. He advises ranking assumptions by risk (specifically how critical the assumption is and how much evidence there is that the assumption is valid). Test the assumptions that have high criticality and low evidence first (a.k.a. build and deliver these first).

Now here’s a key: every assumption’s rank should be based on how critical it is to the business model. But that also means you need to know and understand the business model before you can evaluate. I like the business case to be summarized in a project charter as a reminder of this and to provide context for subsequent project reporting and evaluation.

How often do you think about assumptions in your project practice?

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From the Practice

This week I’m highlighting a great little article from Adriana Girdler on the roles that project managers play that go beyond the title.

She labels these roles as:

• Diplomat

• Negotiator

• Psychologist

• Cheerleader

• Firefighter

• Detective

Wearing your Diplomat hat you need to read the room - understand stakeholder motivations, and tailor communication accordingly. This is about managing relationships. As a generalist PM lean into your big picture and empathy skills to successfully fulfill this role.

Many project professionals think the Negotiator role is just about conflict. Adriana points out that negotiation starts long before the moment of conflict - at the very beginning of the project. As a negotiator you inject clarity and neutrality into challenging conversations that shape priorities. As a generalist PM lean into your collaborative problem solving and strong communication skills to successfully fulfill this role.

Wearing a Psychologist hat might not be your first instinct as a project manager but the ability to see what is going on under the surface of interactions and assertions you observe is one of the most underrated skills in project management. Use curiosity to test your observations, deploy active listening to deepen understanding, and then use your emotional intelligence to clarify what’s really going on. As a generalist PM your empathy and strong communication skills are your strengths in this role.

Intentionally shaping the energy and momentum of the team is a key component of successful project Cheerleadership. When the team is getting bogged down, pump up the energy with praise, belief, and a little patience. When the team is overconfident, ground everyone in priorities and requirements to ensure the right outcomes are delivered. Your most important quality as a generalist PM in this role is your ability to adapt. You’ll navigate highs and lows and the unpredictability of Tuckman’s stages of group development before you reach the finish line.

The Firefighter role isn’t about being reactive or dramatic. Instead, it is being steady, composed, and prepared because you know projects won’t go as planned. Build risk awareness and cultivate contingency thinking from the start. Your generalist superpower when wearing this hat is your flexibility.

Finally, the final role you might need to adopt is that of a Detective. Here you’ll uncover expectations, assumptions, and requirements that aren’t coming to the surface on their own. You are asking the right questions at the right time. As a generalist PM you are tapping into your ability to recognize patterns and see through complexity that might be masking these details.

As you finish reading this I hope you are nodding your head in alignment with this. But I also want to acknowledge that the heavy load many of us feel in delivering successful projects comes from the context switching of these roles, often not acknowledged by others in our organization and often which we ignore or forget ourselves.

If, on the other hand, you are a junior PM, cultivating your skill at wearing these hats is what takes you to a senior level and beyond the PMBOK®.

The path to better visibility in your organization is being seen as competently wearing these hats overtly to improve project delivery.

An interesting read

This week’s interesting read is a thought-provoking idea from the Experience Institute that I think every generalist PM needs to get immediately acquainted with.

Lately I’ve been thinking about what it means to operate in this age of discontinuity.

In 1969, Peter Drucker wrote a book titled “The Age of Discontinuity” which discussed the rise and demise of large organizations alongside the massive shift from manual work to knowledge work. Today we are seeing another shift of a similar scale from knowledge work to “perceptual work” or the “co-pilot era”.

With this disruption, the article argues we are seeing the need for a new capability emerge: collective intelligence.

Image credit: Wednesday Words newsletter by the Experience Institute

As generalist PMs, one of our most important curiosities is our interest in early adoption. Our flexible mindset and willingness to adapt make us capable of early adoption ahead of many of our colleagues.

Pause here for a moment and reflect: what would happen if you started managing your team for collective intelligence instead of collaboration? What friction are you feeling that you might move past if you asked a different question? Generalist PMs are quick to move into problem-solving mode. What are you quietly filtering out when you do this? What value would this have if you let the collisions happen?

I think this might be the key to what generalists offer in this new age of discontinuity. We offer a willingness to recognize our own patterns and temporarily suspend them in favor of experimentation and in favor of collective intelligence.

Leave a comment

A tip

More and more, project managers are being engaged in strategy. And yet, not much is being done to help us cultivate strategic competencies.

Worry no more. Alex Smith has a great summary of the essentials in his Strategy Cheatsheet.

Image credit: Alex M H Smith - LinkedIn

A lesson

This week’s lesson comes to us from Victoria Christensen who writes the Project Management Lab. In her recent post, Victoria writes about her experience chasing perfection and how this awakened perspective on the importance of usefulness rather than perfection. I’ve met many a project manager who struggled with perfectionism. But the truth is that worrying about how the work reflects on you is the most detrimental manifestation of your ego there is. That’s an internal focus when the duties of a project manager are external - to the team.

Usefulness is external.

Where are you striving to be perfect, when you should be striving to be useful?

This week’s love goes out to Simina Fodor for yet another tour de force post. This one subtly hints at one of the key reasons I feel generalist PMs are strongly positioned to lead the future: empathy.

This is your secret superpower.

Often people say that you might use “soft skills” to navigate this space.

But really - to understand what is going on under the surface you have to think and feel someone else’s thoughts. That’s just one skill.

And as we continue down the road our profession is on, more and more of the navigation will be in disruption, murkiness, and uncertainty. The place where frameworks are a pipe dream and work is coming to a standstill.

From the Practice

Several weeks ago now, the Agile Alliance and Project Management Institute publish a new thought provoking document called the Enterprise Agility Manifesto. I’ve been pondering on this document for a while and still feel strongly that it has its pros and cons. But this week, I read Americo Pinto’s article on the link between the Manifesto and PMOs and I have to say friends, this one is worth the read.

The PMO’s responsibility is shifting critically away from doing to guiding. And this guiding isn’t about execution. It’s about value.

Organizations aren’t just going to be adopting some best practice or other and continuing to largely be the same. They will be reconfiguring, fundamentally, at the strategic core.

A PMO isn’t just going to be shaping the projects it oversees. It is going to be influencing the design of the organization overall.

An interesting read

This week’s interesting read comes to us from Mike Fisher. This one is dense and juicy, so grab a quiet corner and a cup of coffee and really dive in and I promise you won’t be disappointed. Mike jumps into the heart of something we are seeing in many organizations at the moment: an obsession with data and dashboards as a way of “automating” our understanding of our business. AI is driving this obsession by helping organizations find data they didn’t know they had and instantly present it like it is valuable.

Mike uses a real world event from 2003 as an illustration of this risk highly effectively.

This article will leave you asking some tough questions about your metrics, your data, and where your failsafes are.

A tip

I’ve met many generalist PMs operating outside the core project management roles. One common area is Product Owners. If you are looking to enhance your skills in this area check out a recent release of self-paced learning available from Scrum.org.

A lesson

This week’s lesson is around something I’m seeing more and more teams struggle with: “relentless delivery pressure”. You know the symptoms: a team with no slack; constantly feeling behind; struggling to deliver fast but paradoxically going slower while doing so. As agile adoption spreads, it feels like this problem is sweeping behind it like a wave. This week’s lesson is the antidote: agile governance.

As teams transition from traditional project management to agile ways of working governance is often thrown out the window. People are thrilled to get rid of the compliance rituals they perceived as blocking progress and the endless approval hoops to jump through. But the absence of governance in agile projects isn’t the right approach.

It’s a well-timed, intentional slow-down, that allows the team to accelerate as it exits the reflection.

Governance doesn’t provide moments of restriction or constraint - it provides moments of orientation.

Interested to learn more? In addition to the great explanations in the article the Agile Governance Consortium Business Agility Think Tank has produced a thorough white paper on Agile Governance. Check it out here.

This week I’ve been inspired thinking a lot about group dynamics and you might notice this as a bit of a theme in this week’s edition of the Generalist PM. I read an interesting paper on the impact of group dynamics on the success of teams. It is an older publication now (2016) but they found conclusive support over a large systematic examination of various types of teams that the most successful teams had a specialist core that were provided key supports by generalists.

This sparked some reflection on how much we design a team for success, and how much of success is about the individuals who form the team vs the team as a whole.

What do you think matters more?

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This week I’m loving

There are many moments in a project management career where uncertainty will well up inside of you. No matter how experienced you are, sometimes, things just don’t go as planned, and when that happens you may find yourself searching for what you should do and coming up empty handed.

Many of us having typical coping patterns we engage in when facing this challenge.

But does it really help you?

Next time this happens - maybe try these great tips from Chris Guillebeau on how to disrupt your default behavior.

I personally find going for a walk can be very helpful. It amazes me how easily the human brain can just chew on a tough problem simply by getting outdoors in the sun at a brisk pace.

If you are feeling helpless, helping someone else can build a sense of accomplishment.

Separating your thoughts and emotions through calming practices like deep breathing can help you gain a new perspective.

Lifting your head and looking toward the horizon and the longer term objectives can refocus your mind and help you see a way past the immediate obstacle.

And another personal favorite of mine: a change of scenery can do wonders for your mood and outlook. Treat yourself to that Starbucks, or touchdown at your favorite coworking spot for a refreshed energy.

Got a tip you’d like to share with our community?

Leave a comment

Bringing our whole, healthy, authentic selves to the teams we lead is a critical contributor to positive group dynamics and team success.

Tool of the week

I’m working with a team at the moment that is Storming along with each other and we really need to accelerate toward Norming as soon as possible as they have lost a lot of productivity, energy, and patience as they navigated the storm.

And if you don’t know much about Tuckman’s stages of group development, learn more here.

I know this type of situation has happened to you as it has to almost every project leader at some point in their career. But shifting these group dynamics is a delicate exercise.

One technique I use that helps teams accelerate to Norming is to conduct a deliberate norming exercise. There’s a few forms this can take. Some teams benefit from documenting their personal needs in a Manual of Me to help teammates work in a compatible manner. Some teams are able to cover norming as part of a team chartering exercise.

But for teams that are really Storming, or teams that have some distance to cover in Forming (a.k.a really fresh) a facilitated team norms exercise can be helpful.

Here’s a method I like to use.

Each person on the team needs to outline three things:

• What they can GIVE to the team

• What they need to GET from the team to go full throttle

• What they will have GRATITUDE to the team for when it is going right

It works well if each person can write each thing onto a sticky note (real or virtual).

Then you can choose one of two options. If the group is small - facilitate the clustering of these sticky notes into common themes shared among the group. Usually there will be some people who GIVE things that other team members need to GET and these would be clustered together. If the group is larger you can split them into 3 groups and have each group work on one set of stickies.

Next, look at any outliers where a cluster wasn’t possible. These should be discussed as a whole team because they could represent something people didn’t think of or didn’t want to share that the whole team was feeling, or, they represent a disruptive behavior that the team needs to figure out how it will streamline. Disruptive behaviors can hinder a team from achieving Norming if this isn’t figured out.

Finally, convert each of the clusters into a statement about expectations as a collective. This arrives at a list of team norms or a foundation for a team charter.

An interesting read

This week’s interesting read comes to us from the s + b newsletter and talks about a unique group dynamic that we often encounter in the business world: the standout.

Many teams have them. That one person who just seems way smarter, way more talented, or simply achieves a level of performance that can’t be expected of the others on the team. At first glance, this seems like a problem for group dynamics, but in reality, we have many examples in life where stars and teams coexist effectively. The article does a great job of drawing parallels between soccer and business with this concept in mind.

I have a different analogy I have often used to explain how these “stars” can valuably guide a team to a whole new performance level with the right support. Where I grew up there is a sport known as “chuckwagon racing”.

Image credit: Shane Kuhn, Calgary Stampede

Now this is a controversial sport with a storied history (where I come from the sport has been around for 100 years). I was fortunate enough to grow up in the presence of a person who knew how to drive a very large team of horses (a virtually non-existent skill these days) and the secret to great horse teams is in the pairing. Where multiple teams exist, each pair must be compatible and there actually is only one lead horse, the rest of the horses are following. Teaching this to ordinary working horses is hard enough - horses can be very spirited and independently minded animals.

Chuckwagons, take this to a whole new level. The horses that run in chuckwagon teams are actually retired thoroughbred race horses. Pause for a minute here and imagine with me. We take the fastest horse - bred especially for this probably through many generations - he’s trained to run at an elite level all by himself to win and this is all he has known. And then, so that he doesn’t go to the slaughterhouse, we hitch him up to another horse and tell him to run together with it. Then - just for fun - we add two more horses. And actually - all these horses are those thoroughbreds but only one of them now gets to be the leader. Imagine the patience you require to teach these horses how to do this. Realize the eye that you need to find these magical pairings and teams. And you’ll get a tiny glimmer into my fascination with the sport.

Because, like the chuckwagon driver, a great project manager is able to figure out how to put a pack of thoroughbreds together, motivate them to follow a maverick and chase a seductive idea together to the end of the race.

You, as a generalist, have a unique talent for seeing this human chemistry, so lean into it - and watch your group dynamic thrive around your “maverick”.

A tip

A great reminder from the ever-wise Jasper Polak. I’ve met many a project manager that thinks meetings are the answer to keeping things on track. It is rarely the case.

Image credit: Twitter.com

A lesson

One tough part about a career in project management is that while we run teams, and we serve teams, we are often by ourselves as project managers and thus not really “on a team”.

If you work with a consistent project team for a while, it can sometimes feel like we are on that team (and indeed sometimes we deliberately cultivate that feeling to be effective) but rarely is this really true. There is always a distance.

Failures happen, and sometimes projects are set that simply can’t be successful. This can lead to tough reflections, and sometimes separation from people you have worked with for a long while (either because the team is disbanded or because you end up on the blame seat and maybe formally separated from the organization and team). Like a knife forged in a blacksmith’s shop - this is just the strengthening of your “expert judgement” likely from lessons that can’t be learned any other way.

But it can spark difficult reflections. Sometimes a period where you may wish to redefine yourself. I feel like generalists are more prone to this feeling both because of our thirst for learning but also because we are constantly reinventing.

How can we cultivate resilience as we navigate this period? Here’s some wise advice from the wonderful Susan David.

Image credit: Susan David.com

Susan wrote a lovely personal story about this theme which you can read here. May it carry you forward through any storm.

I’ll admit that this week has been hectic and I didn’t have much time to slow down and show the love. But this morning, as I write to you, a little quote written in a little post by Elitsa Raynova stuck out to me on LinkedIn that I thought I would share:

This past couple weeks I’ve had a few conversations with project managers who came to me for advice. In each of these conversations we discussed what being a generalist PM feels like. We talked about discovering being a generalist. We talked about finding belonging as a generalist. There were tears, there was laughter, there was a feeling of coming home to something you maybe knew deep down but have tried not to acknowledge.

I thought about my own journey to owning being a generalist PM, and starting this newsletter 4 years ago. So today I’m sending you the love. I’m saying thank you for being part of this circle. Thanks for helping other generalist PMs feel like they belong. Thanks for helping me grow as a writer, as a leader, as a role model. I’ve been thinking a lot about what is next lately, and I’m excited to see where the road takes us.

From the Practice

Agile project managers working with Jira have a must read item this week from Stefan Wolpers. In his Food for Agile Thought newsletter, this week Stefan discusses the limitations of Jira in the era of AI and what might need to be on your radar instead to ensure your organization can maintain the insights it needs.

I very much agree with how Stefan sets the stage around the limitations of Jira as a “ticket-oriented” tool and not really a project management tool. He then goes on to shine a light on some of Atlassian’s latest add-ons with a strong summary of the pros and cons to consider.

And then the problem statement that reflects key challenges almost every team I work with that uses Jira encounters:

The recently released Wellingtone State of Project Management Report for 2026 found that 72% of project leaders are spending at least half a day every month collating data for project reports!

Image credit: The Wellingtone State of Project Management Report - 2026

Next, Stefan dives into what needs to shift to enrich the data organizations are seeking about agile projects:

Stefan points out that this fate is likely to befall most tools whose function is to display data without structured context.

An interesting read

This week’s interesting read (or listen!) comes from Julie Zhuo who captures some great tips from DoorDash Chief Growth Officer Brian Hale on what differentiates teams that grow exponentially from their counterparts. I’m going to let you read it rather than digest it here.

A tip

For those of you leading product development work rather than strictly project work, this tip from Ash Maurya is one of the best reminders I have seen of the different types of risk to consider and what typically gets overlooked.

Image credit: Ash Maurya at LeanStack

A lesson

This week’s lesson comes to us from my dear friend Amber McMillan who cautions us on the temptation of the quick answer. We’ve all felt this moment:

As you give in to the urge to resolve the discomfort out flows an answer. Is it the right answer?

More damaging is what this habit breeds; an organizational culture that thinks urgency = clarity and judges competence by how quickly an answer is given.

Amber reminds us that pausing in the space of “not knowing” can be powerful. It avoids solutions that aren’t thought all the way through. It gives space for people to challenge assumptions. It validates that we are solving a problem that we have fully understood.

This week’s love goes out to a little write up by Janelle Jones for all you systems thinker generalist archetypes out there. The article starts out with a storyline about family routines and how parents may be accidental system architects. It shuffles this brilliant statement in front of you so subtly you might miss it:

It can be easy to assume that people just aren’t working hard enough. Janelle points out that people are responding to their environment.

Janelle also calls out that we often design systems with the ideal in mind. Creating fragile moments of failure at the very first test.

Think about the systems you are in right now, whether it is at work or in life. Which ones are really actually helping? Which ones are full of noise instead of energy? How can you help?

From the Practice

We’ve all had the night where we barely slept ahead of a conversation we were dreading. This week, in From the Practice, we shine the spotlight on a lovely little read from Dr. David Burkus about how a little shift in our approach to these conversations can amplify their power and impact: stop labeling the conversation “difficult”.

But if you don’t go in with an adversarial attitude:

There’s some great tips in this article about how to have a successful “difficult” conversation and I want you to read it rather than for me to digest these. But I’ll leave you with one final parting gem:

An interesting read

This week’s interesting read brings food for thought on our role as project leaders. In the article, Margareth lays out two leader styles that dramatically influence project success but only one of which really influences organizational success. Personally, my experience is this is potentially the true difference between agile leadership and traditional project leadership. Definitely it is relevant to generalist PMs who are natural collaborative problem solvers and may be interested increating safe environments where others can make good decisions.

The article goes on to highlight three key qualities in multiplier leaders and how to cultivate these.

I’m curious, which kind of leader do you think you are?

Leave a comment

A tip

I’ve been discussing project chartering this week and I came across this great reminder of the essential questions everyone should be asking at the beginning of a project.

Image credit: Calvin Omonuk - LinkedIn

A lesson

This week’s lesson is a great reminder about the importance of project closure and an honest look at the real challenges in doing this well. Which of these has happened to you? What strategies did you employ to address them?

Leave a comment

My biggest pet peeve is the 90% syndrome. This is the number one reason folks talk about “transitions to operations” for a project rather than a really delivered outcome. The real root cause? Not having defined a clear endpoint for the project and not holding the team accountable to achieve this. Often pressure that creates this situation is the desire to “deliver on time” organizationally. Formal project closeout can help to identify projects that are lingering and provide an impetus for properly finishing them.

Image credit: Nitin Sharma - LinkedIn

Hey friends! I hope that this week’s newsletter finds you all at the end of a successful week.

Over the past few weeks I’m been pondering an idea and this week I’m being brave and asking you for your thoughts on it.

We’ve got a good little community together around this newsletter and it is my belief that this more than proves that a “generalist PM” is a real archetype in project management.

I know that every company I have worked for has needed a generalist PM exactly at the moment I have worked there.

I’ve heard similar thoughts from those of you I’ve discussed the journey with.

Which leads me to a problem: How do companies that need generalist PMs and the generalist PMs themselves meet each other?

If you’ve got a super great place where you source your roles, let me know here!

Leave a comment

And if you don’t, which has been my straw poll so far, I’m curious, would it be helpful to you if there was somewhere to find a perfect match? If so, what would you want or need?

Leave a comment

From the Practice

This week’s “From the Practice” is highlighting a recent article from Fola Alabi that provides a cool approach to closing strategy gaps in project management and organizational practices. As we have frequently discussed, generalist PMs bring strong talents to strategic execution that can be grown into a strategic practice over time, but just as for most PMs, we rarely have training specifically targeted at this competency. What I liked about Fola’s approach is it helped to both identify areas where competencies are needed and breaks down what to work on or develop to close the gap. This means that any reader could design their own professional development plan to develop the suggested competencies using pre-existing education existing in the relevant areas.

The framework also recognizes that this is a partnership to cultivate professional competencies alongside organizational capability (something I also advocate for in the area of value delivery).

If you’ve been looking at this gap in your own environment and wondering how to address it, this read is for you. If you check it out, I’d love to hear what you thought!

Leave a comment

An interesting read

As project managers we frequently face situations that require us to act in a way that will carry consequences we may not be thrilled about. This week’s interesting read addresses how you can evaluate when are the right moments to stand tall, even when risks arise as a result. I loved this article for providing a simple but effective framework that supports making difficult decisions.

One of the hardest moments as a project manager is when you need to stand up and go against the expected direction. Author Sunita Sah coins a term for this leadership quality that I deeply appreciated: Strategic Defiance.

Acting in this manner is an opportunity to:

• Build credibility

• Earn trust

• Demonstrate integrity

• Think for long-term survival

How do you recognize the moments where Strategic Defiance might apply?

You’ll be feeling tension. That nagging in your gut keeping you awake at night as you chew over the scenarios hoping to find something that won’t create discomfort.

It can be tempting to push that feeling to the side, but, instead, naming your discomfort and examining where you feel the tension is an important step on the path to a solution.

Next you examine the potential application of Strategic Defiance using the framework Sunita describes as the “Defiance Compass”.

Image credit: Harvard Business Review - Sunita Sah

If, after this evaluation, you’ve made the decision to act, your first step is Escalation. Bring the matter to the attention of relevant stakeholders. Ask for clarity.

Communicate that you may not comply. Give the stakeholders an opportunity to reconsider their position.

And finally, if nothing changes, then take your principled action.

Not all acts of Strategic Defiance are loud or large. It is a muscle that you can exercise with small acts where you practice reflecting, using the compass, or resisting without going all the way.

A tip

If you haven’t already registered, I highly recommend signing up to attend PMXPO 2026. This free virtual event hosted by PMI each year is always packed with trend-worthy discussions and knowledgeable speakers. Registering for free allows you to attend live and access on-demand content if you are a PMI member.

Key topics that may be of interest include:

• Pulse of the Profession: Leading Project Success in a Complex World

• Influencing without Authority

• Product Delivery in 6 Steps

• Refocusing PMOs on Business Outcomes

Learn more and register here.

Image credit: Project Management Institute

A lesson

This week’s lesson highlight, with several lessons to offer, comes from Hanadi Usman who writes from her practical experience in Canada leading a high profile transformation initiative in Canada. Here are my key words to live by from Hanadi’s reflections.

You don't need consensus. You need clarity about who decides, and a process that moves fast once the decision is made.

Plan enough to start. Adjust as you learn. Build feedback loops that let you course-correct without starting over.

Decision velocity matters as much as decision quality. Build structures that let you decide fast and adjust if you're wrong.

Fast execution requires stronger governance, not weaker governance.

You don't need to approve every decision. You need to see every decision.

Credentials get you the interview. Judgment gets you the outcome.

This week’s love goes out to this gem that popped up in my LinkedIn feed and resonated deeply with my identity as a generalist. The premise was the idea that organizations design roles to try to put people in boxes, failing to recognize the true capabilities that people actually bring. What if we designed organizations differently? The transition to skill-based employment is happening and I am hopeful that more and more organizations will have greater recognition for what you truly bring instead of the box they try to fit you in within a very near future. But in the mean time, I hope this visual satisfies you as it did me.

Image credit: Liz Fosslien for Corporate Rebels

From the Practice

This week’s From the Practice is sparked by a post from my friend Benjamin Chan discussing resilience. Coincidentally in my inbox was an issue of Strategy & magazine with an article discussing resilience as a skill originally published in 2020.

As we dream of a skills-based economy something stands out to me that demands clarity: the need to differentiate skills, behaviors, and assessments. If you are interested in becoming a sought after project manager with future-ready skills, which I assume is why you read this newsletter each week, this distinction must be ingrained in your daily approach.

In the Strategy & article, authors Azeem Azhar and Ceir Ann Droog discuss resilience as a skill. But they also suggest “some people are naturally resilient”. I agree with the idea that resilience is a skill, but I don’t agree that people naturally have this. We are not born with skills. We may be born with a talent capacity, otherwise known as an aptitude which can be shaped through training and practice into a skill. We are not born with skills themselves. This draws attention to an important distinction between “naturally resilient” teammates and those cultivating the skill later in life: upbringing.

There is a natural aptitude that relates to resilience and it is called Grit. Angela Duckworth characterizes this as the combination of passion and perseverance in her book titled “Grit”. Angela believes that grit can be cultivated and that it is done so through training in adults and upbringing in children. Exposure to opportunities that reinforce passion or perseverance or the combination of the two is the magic here.

Ben brought up the idea that resiliency could be interpreted as or mistaken for stubbornness. Stubbornness is definitely not a skill, instead it is defined as being unwilling to change one’s mind, actions, and/or attitude within a given context. In actuality, the actual act of being unwilling to change one’s mind is a behavior known as obstinacy. When we characterize someone as “stubborn” we are actually carrying out an assessment of their behavior that presumes that their obstinacy is without justification. For example, I could be dogged about telling the truth of a situation and be perceived as “stubborn” by someone who has a different perceived truth. When in actuality I am behaving obstinately because I am attached to my truth (often also stated as “the truth” but we’ll discuss the complexities of that some other time).

Viewing workplace interactions with the lenses of skills, behaviors, and assessments allows us to see new perspectives when evaluating interaction quality. Being conscious of the risk of assessment can help us to see and uncover biases during evaluation of workplace interactions. Getting clear on skill gaps and undesired behaviors provides us with a productive baseline from which to coach employee development.

So here’s the framework I suggest you consider as you move forward:

Skill - a learned capacity to achieve a specific outcome such as achieving a goal or completing a task.

Behavior - an observable and measurable response to internal and external environments

Assessment - an observation and evidence-informed evaluation of a skill or behavior

Other terminology that confuses this clarity:

Talent - exceptional competency in a skill or behavioral context

Aptitude - an innate predisposition toward a skill or behavioral context

When we hire or engage team members we are assessing aptitude, talent, and/or skill. Behavioral interviewing, an increasingly popular technique in modern hiring, is an effort to evaluate a candidate’s response to internal and external environmental scenarios. It potentially has a significant flaw: it relies on the detection of conscious responses, ignoring that many environmental scenarios can prompt unconscious responses which are very difficult to measure or assess in an interview setting. As projects present relatively stressful environments with plenty of unknowns, this approach in particular is unlikely to uncover the patterns that will be seen during employment as unconscious responses are triggered.

To apply this framework and reduce bias in your hiring and management practices you can use these powerful questions:

• What skill do I need to acquire through this hire?

• What aptitude(s) am I able to cultivate in this individual?

• What are this candidate’s most relevant talents?

• In this situation what is the desired behavior?

• In this situation what are the potential unconscious responses?

• How am I measuring this behavior?

• Why did I observe this behavior?

• Why am I reacting to the observed behavior in this way?

• Is the combination of this individual’s skills, aptitudes and likely behaviors productive in the interactions we will require of them?

• If I improved the assessment of this individual’s skills what would I be looking for?

• If I improved the assessment of this individual’s behaviors what would I be looking for?

• What is the first step this individual can take to cultivate the desired aptitude, skill, or behavior to be more aligned with my expectations?

The language we use around expectations, norms, and values shapes the development of skills, behaviors, and aptitudes. Objective assessment is the most powerful tool in your management toolkit.

An interesting read

Loved this little read this week that touches on what it is like to be a generalist in a world that expects a specialist storyline.

Image credit: Meg Scheding - Strategic Pivotery on Substack

This week in the Generalist World community there was some ongoing discussion about the exhaustion that comes from trying to tell your story in entirety, in ways that are understood from the lens of specialism, and Meg’s article felt like it offered a brilliant solution.

What if you could boil your story down into a slide this simple? Would it help during interviews? Family dinners?

Image credit: Meg Scheding - Strategic Pivotery on Substack

I’m thinking about what mine would look like, and also which one of Meg’s hats to buy. I hope you enjoy this read as much as I did.

A tip

One of the big challenges I found in making the leap from projects into strategy & operations was terminology. As a scientist by training, project management and lived experience provided most of my business acumen toolkit, at least until completing my executive MBA last year. Metrics are a critical area project managers need to be engaged on these days but translating the lingo around common metrics can feel intimidating. Here’s a great cheat sheet I came across on common KPIs you may encounter.

Image credit: Chris Donnelly - LinkedIn

A lesson

We close out today’s issue with a helpful lesson on the power of the straw man from Mark Warner at the Project Management Blueprint. While Mark explains the concept in the context of software development, my experience is that a straw man can be useful in many scenarios in projects. Think, a straw man governance diagram presented to early project stakeholders. Or a straw man product concept presented to user focus groups before a higher fidelity design. etc.

You all know that I’m a big fan of Alex M. H. Smith but this week, I’m sending the love out to one of his best posts ever about your unfair advantage. And, my generalist friends, I hope you listen up because this is a sweet spot for us: personal curiosity.

Image credit: Alex M H Smith - LinkedIn

Pause for a moment and feel valued. As a generalist, this means, your uniquely meandering life experience is uncopyable. It is your brand. It is what helps you to deliver unique value to everything you touch. All you need to do is:

• Focus it

• Speak it

• Act on it

Image credit: Alex M H Smith - LinkedIn

From the Practice

This week’s “From the Practice” features practical advice from Antonio Nieto-Rodriguez for keeping up with the evolution from task management to transformative leadership he brands “Career 3.0” for project managers.

Specifically, an entrepreneurially mindset that defines direction instead of following instructions or prescribed practices. This is something I both deeply believe in (and have spoken about at a few conferences) and feel is a moment for generalist PMs; here’s why:

• The new project management career is a “portfolio of value-creating experiences” (I almost drafted a new format of my resume thinking about this)

• The new landscape will reward project managers who approach their roles with curiosity, initiative, flexibility, and a growth mindset. If that doesn’t sound tailor-made for a generalist PM I don’t know what does.

• The new superpowers lie in observation and connecting the dots no one else can see (*ahem*)

• The role requires being comfortable with ambiguity, and creating space for people to show up authentically. (! empathic leader !)

• Your greatest visibility will come from standing out as a strategic partner (that’s right folks, your big picture lens is in demand!)

• Careers are shifting to be narrative based instead of accomplishment driven. (*phew*)

Career 3.0 is yours for the taking!

An interesting read

It was tough to choose a great read this week as there were a few of them, but I’ve opted for the one that landed close to my heart this week. I feel it might speak to all of you deeply when you think about the limits we place on ourselves and the limits the world may dictate to generalists on occasion. I loved every minute of this read and I know I will go back to it again and again for its beauty. So, just read it, no other notes from me. If you like it, show Keta some love!

A tip

As the end of Q1 quickly approaches, ask yourself, are you burning out? Not sure, or need some support? We are getting lots of great feedback on a recent webinar I participated in for the PMI “In My Shoes” series discussing how to prevent project failures due to burnout. View the recording here.

Image credit: Emily Luijbregts and PMI

A lesson

As you climb the project management ladder, a key part of your management evolution is in less “doing”. With this, comes the responsibility of delegation. Few project managers are taught this. This week’s lesson from Dr. Hayley Lewis at HALO Psychology will teach you how to delegate in six easy steps.

This great post from Jeroen Kraaijenbrink that drives home a really important consideration about attention distribution in many organizations today. Namely, that it isn’t properly directed at strategy. But also that we perhaps don’t properly devote it to real implementation.

There are other statistics to back this up. For example in 2022, Asana’s Anatomy of Work survey found that only 9% of knowledge worker time was spent on strategic work.

Image credit: Anatomy of Work Survey - Asana - 2022

As project managers, it can be easy to get caught up in the work Jeroen highlights as “analysis and planning”. But generalist project managers can bring our big picture lens to prevent this. Jeroen cautions that if you think you have a strategic execution problem, before jumping straight to a correction in strategy or the implementation plan, analyze attention. Is attention directed in the right proportion at the right targets? If not, fix that first before pivoting in other areas.

I especially appreciated the clarity of these distinctions:

How does strategic implementation feel in your organization? Did this post resonate?

Leave a comment

From the Practice

This week’s segment on the practice of project management highlights a recent academic publication in the Project Management Journal discussing and contrasting decision-making between artificial intelligence (AI) and human project leaders. This article set out to evaluate the suitability of AI as a substitute for human decision-making, particularly in top-level decisions in projects. The authors collected 37 human responses and corresponding answers provided by an AI tool surrounding identical decision-cases. Human respondents were people who frequently acted as Project Sponsors or had similar senior roles. The AI used was ChatGPT 3.5. The aim was to answer the question: how do human and AI decisions differ?

Top management decisions were categorized into the following types:

• go-ahead decisions (a.k.a Go or No-Go decisions)

• prioritization decisions

• goal-setting decisions

• value-setting decisions

• structure-setting decisions

• authorization decisions

• agenda-setting decisions

• oversight decisions (informed by project data)

• choice of action decisions

• mediation or conflict resolution decisions

• approval/acceptance decisions

• termination decisions

AI answers scored significantly higher in logical reasoning and creativity; however significantly lower on bias and moral hazard. Results were inconclusive on speed and efficiency of decision-making.

The authors then considered the possible future where AI and human decision-making are used together in project decision-making, an outcome viewed as highly likely based on current trends. They discussed the risk that over time this causes influence on decision-making overall based on the results of decision patterns by the AI and the human project leaders.

Over time, the authors indicated the risk is, “AI-induced deviation in decision-making”. A recommended best practice was documenting the use of AI for decision-making to help differentiate decision data used for AI development. The introduction of AI into decision-making in top-level project decisions should be done consciously and under dogged scrutiny. The decision to outsource decisions to AI should be the responsibility of leaders who will be held accountable for those choices.

The moral of this story is, just as we are finding in other sectors and AI implementation in general, successful implementation of AI for project decision-making will require reimagining roles, process, and policy.

An interesting read

Our interesting read this week comes from Jeffrey Yip and Dritjon Gruda, hot off the Harvard Business Review presses. The article discusses something I know project managers are highly familiar with: managing up. Specifically, managing a boss or project sponsor who is struggling with insecurity.

What I loved most about this article is it presents a framework for addressing the most common presentations of insecure leadership: anxious leaders and avoidant leaders.

Anxious leaders - you’ll recognize this person by their constant desire for connection. If they feel excluded or criticized, watch out! This leader walks an unpredictable path that can change direction abruptly with the perception of being slighted. They are constantly cycling between micromanaging and overapologizing. You will have moments where you love this leader’s energy and moments where you are exhausted of the rollercoaster ride with them.

Avoidant leaders - you’ll recognize this person by their distance. While they appear calm and independent, this façade hides deep turmoil under the surface. Having an open dialogue will be next to impossible. This leader will tend to drift into control when the stakes are high; react dramatically when criticized; and you’ll constantly feel like you don’t know much about them. They are afraid of needing you too much and distance is their defense.

Working with these leaders you’ll encounter common pitfalls.

• Unequal collaboration - you spend your time anticipating needs and glossing over bad news. Over time boundaries blur and you find yourself striving for unrealistic expectations.

• Independent operation - the absence of useful support from your manager or project sponsor causes you to seek their input less. You try to solve things on your own but find that the situation gets worse, not better.

• Confrontation - well-intentioned advice provokes a reaction you don’t expect and escalating breakdown in communication. Rather than solving your frustration you find yourself being benched.

Yip and Gruda recommend a three-step process they call “The 3Rs”. Regulate - Relate - Reason. This is informed by attachment psychology and acknowledges that most leaders under pressure are reacting based on instincts rather than logic. Here’s a quick overview of the approach:

1. Regulate. Help your leader to regulate their nervous system by reducing ambiguity, communicating clearly and slowing things down. Exude soothing nonverbal signals.

2. Relate. Respond relationally. People who feel safe are more likely to hear what you have to say. Be consistent. Use inclusive language. Minimize change and ambiguity. Meet them where they are at and communicate/collaborate in the mode they prefer.

3. Reason. Communicate clearly and frame your rationale within the relationship you have built. Invite collaboration. Document discussions and decisions to confirm alignment.

A tip

A lot of project managers and especially those working in transformational or strategic projects, will encounter change management as a necessary duty. There’s a lot of natural alignment in change management and project management, especially around planning, complexity, and of course — getting things done through people.

Our practical experience with change management, however, is often painful. What sounds good on paper is rarely everything we need and we spend a considerable effort on managing the unknowns.

So I loved this great reminder from Justin Balaski that one cause of this is our desire to plan change too far in advance. Like agile project management, we can’t plan what we don’t know. What will work is learning and adapting as we go.

Image credit: Justin Balaski - LinkedIn

A lesson

This week I’m highlighting a great lesson that many project managers will encounter, especially in startup environments, shared by Janna Bastow, who writes from the product lens.

Here’s the scenario:

• You’ve built a roadmap

• You present it to your CEO

• And you get the age-old question: “when will this be done?”

In this moment, no matter whether you are a product leader or project leader, the pressure to address this question is the same, and so is the result. A date that won’t be real, and the slowly growing dread of the conversation that will be had as the date arrives. Janna points out:

The CEO asks for dates because it satisfies their anxiety. Their anxiety, however, might really be around questions like: does the team have the direction needed? Is money being spent wisely? Are we working on the right things?

Frame your roadmap discussion differently to eliminate this problem.

Project and product leaders are embedded in a “translation layer”. Where project details, links to strategy, and data that shows progress are abundant in tools that make sense to these leaders, and obfuscated from executive leadership. We end up in a role interpreting these information sources for the executive team. Doing a good job of this will instill confidence. Not addressing it will erode time and trust.

So the next time you find yourself being asked to give dates you know you can’t commit to, pause — ask yourself: what anxiety is filling the room here? Consult your sources of truth and select information that can address the anxiety, and then — translate these details into a story line focused on fostering confidence.

This week’s love goes out to Jesus Romero for a fun LinkedIn post in honor of Valentine’s Day about project manager love languages. He points out that if our love language is a mismatch to our stakeholder’s expectations then we can experience misalignment and disruption.

Image credit: Jesus Romero - LinkedIn

I think I would add a few things to this list.

Speaking in Stoplights. The love language of risk. “This project is about to run a yellow. I think we should…”

Acts of Advice. The love language of mentorship. “If I was in your shoes I’d…”

Process Gardening. The love language of continuous learning. “What I see going off the rails here is…”

Which love language is your favorite?

What would you add?

Leave a comment

From the Practice

This week’s Practice spotlight shines on a great write up by Joshua Barnes one of the creators of Disciplined Agile that discusses something many project managers overlook: whether a project can be broken apart into smaller pieces. For those of you not familiar with Disciplined Agile, this article may be a tad unapproachable, but the message is important, so I’ll simplify it here.

Joshua points to a question we might all want to be asking: “Are your projects too big to succeed?”

Technical project managers will be familiar with the idea of breaking down work into smaller pieces or slimmer slices but we typically apply this concept only at the task level. Joshua asks, should we also apply this at the project level?

You may ask, what is the advantage of breaking a large project into smaller projects?

Joshua notes several important considerations:

• Reduced dependencies

• Exposed assumptions

• Earlier value delivery

And most importantly, in my opinion, earlier value intelligence (i.e. if we deliver earlier we can learn whether we have the right bet earlier).

Further, this also reduces initial investment and the ROI (Return on Investment) risk, and when we learn early about a “first step” on our planned path, we can possibly avoid wasting the rest of the investment entirely!

So how can we slice and dice a large project?

Joshua suggests a simple approach.

1. Map all the known requirements into a single visual workspace.

2. Group these requirements based on natural patterns such as being related to the same persona, workflow, or outcome.

3. Look for a group that is well understood, can be estimated, addresses priorities, and makes sense in a high-level sequence toward the final desired outcome.

4. Scope this group as a project.

You can repeat this process for other groupings and also examine which things depend on each other and which things may be able to be executed simultaneously. This can fundamentally change the organization of our resources as well.

An interesting read

This week’s interesting read is an article by Maarten Dalmijn that talks about something I teach in many organizations I work with: the advantage of PULL planning vs PUSH planning.

Like Maarten, I’ve seen many companies take what we now view as a “traditional” approach to planning that takes into account things like holidays, team size, resource allocations, historical velocity, and sometimes various complex simulations such as Monte Carlo experiments. My chief concern with these efforts is that they waste a ton of time for essentially zero benefit.

Maarten draws the analogy of this effort to the myth of Sisyphus. If you don’t know this story, read about it here.

The biggest problem with this approach is it only works if your forecasts are accurate and your forecasted capacity exceeds the required effort. At the start, we use estimated effort to represent required effort, and I hope that you can intuitively see what will be wrong with that substitution. If the required effort exceeds the estimated capacity - which it likely will since someone always gets sick; then we simply run out of capacity for the required effort and cannot complete the deliverables in the time planned. The boulder, rolls back down the hill. Worse still, likely your organization did something cray cray like plan the whole year of work, so when the first boulder rolls back, not only is that work not finished, but now it has put every other work package at risk as well. And… like Sisyphus, you are now in an eternity of never getting the boulder to the top.

My mantra I give to companies struggling with this problem is:

We need to shift our mindset from allocating resources to work; to allocating work to resources.

When we make this shift our approach is informed not by theoretical capacity but by actual capacity.

Now the typical reaction to this shift is expression of worry about how we will know when we will achieve the ideas we set out to deliver. Most businesses have stakeholders to report to and accountability to customers that drive this panic.

And here’s the answer: have clear priorities that define what is “Must Do” vs things we hope to be able to accomplish. You can take this all the way to a full MoSCoW framework if you want, but at a minimum, we need to know the non-negotiables.

Then, we focus the team on those “Must-Do” items and the trade off is: when real effort exceeds what we expect, some of the “nice-to-have” items fall by the wayside. As the team focuses on work, and accomplishing it within the effort required instead of within an artificial, and wrong estimate, of the work required — the team also accomplishes greater productivity because their stress and burnout trying to achieve artificial targets is reduced. If you implement a properly prioritized PUSH system you should actually improve your delivery, not reduce it.

And the ultimate bonus? You get all that time back that you waste on those perfect spreadsheets for resource allocation and all the simulations that built them.

A tip

This week’s tip is a reminder about kindness from Victoria Repa.

89% of employees say kindness at work is a top priority.

Kindness is a skill. You’re not simply born with it.

Image credit: Victoria Repa - LinkedIn

A lesson

This week’s lesson is a reminder from Alex Smith about the strategy antipattern seen in many organizations known as “Optimization”.

Image credit: Alex Smith - LinkedIn

I strongly recommend reading through Alex’s document in entirety as it is one of the best breakdowns of why this is a problem that I’ve seen.

What motivates organizations and leaders down this path?

Image credit: Alex Smith = LinkedIn

Watch out for this behavior in yourself and others in your organization. Being conscious of it, is the first step to correcting it.

This week’s love is headed toward a zone that isn’t that typical but since many generalist PMs are working in smaller businesses or startup environments I’m betting that you’ve encountered this at least once.

GTM (Go-To-Market).

And more specifically, GTM that isn’t working.

Krista Mollion, published an excellent overview of GTM and also covers some really common anti-patterns you’ll see in early efforts. If you’re in a startup environment, I highly recommend the read!

From the Practice

This week we are going to talk about something that is difficult for all project managers.

A deliberate pause.

In today’s workplaces it can often feel like the pressure to move faster is constant. But this week’s PM Global Career Compass reminds us that this can often mean we are mistaking speed for effectiveness. One of the most valuable skills you can cultivate is knowing when to pause.

This is sometimes also known as: “strategic patience”.

Slowing the pace down can improve the quality of decision-making; create space for alignment; and increase the value of the project’s outcomes.

It also creates an important space for project managers to tap into their strategic thinking skills. Maybe the answer is in the big picture if you take time to zoom out. Maybe with time to think you can create value you couldn’t see before. Maybe you need time to dig into the details or play around with the sequence of things to adapt the schedule. Maybe the team needs time to discuss substitutes and alternatives to find the best course of action. Maybe there’s an opportunity that you almost rushed by because of the stress. In all these situations, pausing, is powerful.

A strategic pause will have a few hallmarks:

1. Momentum is maintained.

2. Communication is clear.

3. Credibility is earned with stakeholders.

4. Urgency is imposed, not genuine.

An interesting read

This week’s interesting read comes to us from Mike Fisher who hits a home run with a practical discussion of the challenges of speed from the organizational perspective.

Interestingly, he picks rugby as the metaphor in the article.

I really want you to read the article so I’m not going to summarize it here. But the essence is:

Notice the use of the word “allow”.

We often think of conditions as constraints - guardrails that produce or contain an outcome.

But this subtle cue reminds us that the highest performance environments are permissive, not contained.

If you want your team to go fast, here’s the lessons:

1. Unglamorous effort comes first. Speed is earned.

2. Ruthless focus is required.

3. Create shared intent and action will follow instinctively.

4. Prepare, so that adaptation is inevitable.

5. Eliminate the fear of making mistakes.

A tip

Potentially the most exciting conference this year just opened for registration.

If you’ve dreamed of visiting the Dubai World Trade Centre, this is your chance!

Early bird rates end in 10 days, don’t miss out! Register here.

A lesson

There’s a lot of talk these days about understanding EQ (emotional quotient), also known as “emotional intelligence”. But what do we really know about EQ?

Dr. David Burkus provides us with this week’s lesson on what many leaders get wrong on the topic.

Emotional intelligence has four dimensions:

• Self-awareness

• Self-regulation

• Social awareness

• Relationship management

But this isn’t just about people getting along with each other.

Because emotions are a driver of behavior. Ignoring emotions is failing to engage one of the most powerful levers for team performance.

In fact, for teams dealing with low self-awareness, performance can be cut in half.

How can you use this powerful lever to your advantage?

1. Be intentional with your own emotions. Ask yourself “How do I want my emotions to affect my team?” Plan how you’ll show up to fulfill that.

2. Listen for what people don’t say. Empathy and honesty will create space for focus and engagement.

3. Reinforce trust with signals that indicate to your team that they are being heard. Nod your head, make eye contact, paraphrase their statements to confirm understanding.

This week’s love goes out to Linda Cureton for her excellent article highlighting the underlying cause of workplace politics: scarcity.

I loved this article because it helped me to understand something very important about being a high performer: competence can lead to favoritism. Being reliable and effective may cause leadership to choose you for tasks more frequently. As favoritism emerges, people defend their ground by shifting their selection for tasks to minimize perceived threats to their own positions. As decisions shift in this manner, power becomes guarded, and scarcity is reinforced.

How can we avoid this?

Ensure you build a workplace culture that awards responsibility based on whose skills are best suited. Connect decisions with clear problems. Ensure solutions focus on value. Encourage lateral collaboration and influence.

As generalist PMs one weakness we have is our focus on the big picture and our natural tendency toward collaborative problem solving can mean we don’t notice politics as early as others. I hope this article resonates with you and shows you some clues to keep your eye out for to avoid the pain of high performance in a scarcity-driven culture.

Image credit: Linda Cureton - LinkedIn

From the Practice

With all the buzz about AI a the moment it is starting to feel like every hiring candidate is an AI expert. This has prompted a lot of talk about differentiating and assessing true skillsets. I recently was working in a space, for example, where the subtle but very important difference between machine learning and computer vision mattered.

As project managers we are often involved in selecting/hiring a team and since many organizations are starting AI projects or transformation activities that require acquisition of capabilities, I anticipate this will be fairly common for the next 24 months.

But how do you assess candidates?

I love the framework suggested by Alex Ewerlöf in his recent post here.

He focuses on levels of AI Fluency. Like learning a new language, there are various levels of engagement, competency, and relevance in each level.

If you check it out, I’d love to hear what you think!

Leave a comment

An interesting read

This week David Epstein (author of the book “Range” all about being a generalist) interviewed Brad Stulburg with an intriguing new book launching this week called “The Way of Excellence: A Guide to True Greatness and Deep Satisfaction in a Chaotic World”. I’ve added this to my reading list and I imagine many of you will be interested to do so as well.

David sums Brad up as a: “psychology-infused modern philosopher — who can deadlift 530 pounds. I mention that last part because his work often stresses the importance of doing difficult and engaging things in the non-virtual world.”

The book is about how to figure out how to do things that are worth doing. David asked Brad what prompted him to decide to write about this.

The book outlines “excellence”, not as a crowning achievement, but as a process — caring deeply and committing to give something your all.

I personally love this idea. In particular, as a recovering over-dedicated project manager, I love the idea that there might be a way to improve our ability to judge when to invest this care.

Brad’s discussion of the difference between satisfaction and happiness was also illuminating.

I think as generalists focusing on satisfaction may be a more useful approach than happiness.

There is also some great discussion around sense of self and how we define our identity. In particular I feel this is deeply valuable for generalists who don’t have the obvious “one thing” that specialists can easily identify with.

Finally, Brad has some great reflections about stepping outside our comfort zone and owning our ability to deliver in that environment. Something all generalists need to cultivate.

I’m looking forward to diving deeper into Brad’s thoughts in the book!

A tip

Here’s a list of 7 mindset shifts that can accelerate your project management career this year courtesy of Benjamina Mbah Acha.

Image credit: Benjamina Mbah Acha - LinkedIn

A lesson

This week’s lesson comes to us from Jeroen Kraaijenbrink on the topic of change.

A significant portion of change efforts fail. Many of these failures can be attributed to leadership choices.

Jeroen calls out that this isn’t just to do with the plan around the change. Instead he notes two key forces that must be carefully balanced:

• Involvement

• Structure

The warning signs are when involvement goes beyond what is needed and when structure turns into control.

Good change management sets the wheels in motion, treats people as capable humans, and understands the right level of engagement to keep the change moving on the right path.

Keep an eye out for these pitfalls and focus on balancing the management of change and you’ll succeed.

Image credit: Jeroen Kraaijenbrink - LinkedIn

This week I’m loving…

Practical and actionable advice from the wonderful Kathryn Montbriand about the real-life juggle of a generalist.

In her article, published for Generalist World, Kathryn described the “plight” of the generalist as “we can do anything…so sometimes we do everything.” I’m sure for you this strikes a chord as it does for me. However, the answer that the world gives us for this problem, is usually delegate, take on less, focus. How good are we at this?

Enter, the mental model of the stovetop. Your value is finite. You can only spread yourself so thin before you’ve dispersed your energy across too many things. The stovetop has capacity for 4 pots. Try to cook more than 4 pots and there isn’t enough heat. The burners are different sizes and this represents the energy you can invest in each of the things. I don’t know about you, but I loved this visualization. Just like cooking on a stove, you can dial-up and dial-down the energy you put into the 4 pots.

The beauty of this mental model at first glance is in its simplicity. However, what I also loved is that it simplifies a tough scenario we generalists encounter often: the need to give up on something. If you use this model correctly, firstly, choices might be simplified by focusing on the impact you can make with your valuable energy. This might make it easier to select the 4 pots. Secondly, you don’t have to feel that you must give up on something when other things are competing. You can dial-down the energy on something to dial-up somewhere else, and the 4 pots can stay on the stove.

It’s a mental win-win.

Kathryn goes on to provide practical advice about how to use this model combined with quarterly planning and objectives. I recommend you read the full article if you are inspired to try this.

Tool of the week

Many organizations I have worked for and consulted for struggle with resource planning.

Many project management tools either lack resource management tools (sad face Asana), charge sizeable fees for a resource management add-on (ahem… Smartsheet), integrate resource management with features that go beyond project management (I love you Harvest Forecast but…), or just overcomplicate resource management with makework and hassles (I’m looking at you Jira).

But there’s this little known tool I’ve used successfully in a lot of settings that finds the sweet spot among many of these problems. You might have seen me be a huge fan of this tool on Twitter. They advertise themselves as “Blissfully simple resource management software” and they live up to this promise in my opinion.

If this sounds like the magic you’ve been dreaming of. Check out Resource Guru.

And in case, you aren’t sold yet here’s the reasons I recommend it:

1. Costs start at a little over $4/mo per person. Everybody gives up one Starbucks latte a month and voila, you can afford it. But Harvest Forecast is only $5 per month, you say…yes but try using Harvest Forecast without it’s sister tool Harvest Time Tracking at $10+ per user per month. Call me when you’ve got that working as well as Resource Guru.

2. Don’t just track availability and scheduling. Understand your resources. Importantly, track teams, locations, and skills for every resource. Better yet, search these skills and metadata when you start a new project to find the right fit team every time.

3. Project scheduling and portfolio views of project schedules. Paying for that Asana Business subscription to get drag and drop scheduling that immediately rolls up into an overarching view across Projects? (Still my favorite part of Asana!) Resource guru can do this too for a fraction of the cost. Working in a tool like Trello for free? Here’s the paid tool that integrates and levels up your project management while avoiding breaking the bank.

4. Finally, you don’t just have to manage people resources. Schedule your equipment and meeting rooms in the same tool.

Still not sold… you can try it out with a 30-day free trial!

NOTE: Tool reviews are entirely my own. I don’t get any support from the tools I mention in this newsletter.

An interesting read

This week I’m shining the spotlight on a great article by Jason Orloski that describes the traits of a great PMO (Project Management Office) Leader.

As a former PMO leader myself, and someone who now coaches organizations with respect to design and implementation of PMOs, I can attest to the importance of the mentioned traits.

So, what are the traits of a PMO leader? Well, it’s a balance between a strategist, nurse, psychologist, analyst, fire fighter, negotiator, and boxing referee all rolled into one.

For generalist project managers aspiring to PMO leadership here’s some particularly noteworthy traits to consider:

• Strategic Mindset and Executive Advisor (I particularly love the emphasis on giving advice to Executives)

• Communication Skills

• Empowering People Leader

• Flexible but effective Change Agent

• Self-managing and humble leader

• Decision-making (especially Decisiveness)

• Playing a long game beyond the short-term obvious

A tip

Project chartering is an essential art learned and practiced by the great project management masters.

Just one problem, we don’t really teach it.

I’ve spent over 10 years refining my approach to project chartering to the point where I now teach the same method to every organization and project manager I work with.

Here’s the biggest secret.

I define and link Project Objectives, Deliverables, and Success Criteria by publishing them in a table.

Bonus, it naturally reads left to right to support understanding.

I’m finalizing a template and guide for Project Charters that will be available in Notion or for Google Docs. Want to check this out ahead of everyone else?

Reply to this email.

A lesson

I started my PMP career in the worst learning environment possible. As a wolfpack of one.

Worse, I didn’t know any PMPs within the organization (even though there were 5000 staff); and my boss was a doctor. Not someone who could help me learn the craft.

This…as they say…is the trial by fire.

I learned every failure through actual failing. I learned every stakeholder misstep by actually messing up relationships. I learned about risks by failing to identify them. I learned about how to motivate project teams by trial and error.

But I also learned, that I was immensely valuable in a sea of colleagues who couldn’t see the world the way I could.

Project managers have a completely unique perspective on organizational success.

Own it.

Live it.

You got this!

This week’s love goes out to a health leader whose work I have loved for a very long time: Helen Bevan. This week Helen was inspired by this graphic:

Image credit: Tanmay Vora shared via Helen Bevan on LinkedIn

What I loved about Helen’s post is that she called out curiosity as an important strategic capability. We have been talking a lot about how our role in projects is shifting toward strategy. We have been talking about how this suits generalist PMs because of our natural love of the ‘big picture’. But I bet you hadn’t considered that curiosity might be the true skill you bring to this facet of your evolving role.

In my junior PM days I remember often being prompted by my supervisors to approach things with “curiosity”. However, the desire in this advice was often to simply superficially apply appreciative inquiry as a tactic in interpersonal exchanges and I have always felt that I was, in general, a curious person even if I was not always perceived that way as a leader.

The truth is that simply asking questions doesn’t set the stage well for teams to become genuinely interested. As I quickly learned from the early advice I had received, just asking the question tends to just draw attention to the uncertainty.

My questions often became perceived as a demand for a solution and I think many project managers are guilty of this to a degree as we are often tactically focused on “how do we fix this”.

Helen reminds us that if we can tap into our curiosity and rephrase the question as “what might we be missing?” we can avoid the threat response and defensiveness and tap into the team’s creative problem-solving instead.

So the next time your team is in crisis and you are tempted to ask “how do we fix this?” don’t. Instead try these behaviors:

• Signal that questions are welcome and that it is ok to not understand or know the answer.

• Design meetings around questions rather than updates. Avoid the long powerpoint deck and instead prompt discussion with 2 or 3 curious questions.

• Thank team members who raise issues or ask clarifying questions.

• Encourage experimentation and small tests that “try-out” potential solutions with a view of failure as learning.

• Ensure diverse perspectives are welcomed to the discussion.

And follow Helen. You won’t be disappointed.

From the Practice

This week’s practical reminder is about one of my top pet peeves: story points. It comes to us in the eloquent and impactful narrative we have all come to know and love from Simina Fodor. I’m excited that I’ll get to be on a panel with Simina discussing women in agile project management in March (get your tickets here).

I’m limiting my summary here as I really want you to read Simina’s post, but if you don’t have time, the reminder in a nutshell is:

One problem that I think contributes to the scenario Simina describes is teams don’t really understand how story points should be properly used and project managers aren’t equipped with a process to teach this.

So here’s how I teach it to teams that are struggling with this.

First, some basics we all need to understand to use story points effectively.

1. Story point values follow the Fibonacci sequence 1, 1, 2, 3, 5, 8, 13… This models exponential growth as a reflection of complexity.

2. One problem with this method is people will define their understanding of complexity from their perspective; meaning what my value of 1 is will be different from your value of 1. This means the team needs to agree on what we mean by 1 before we try to assign points to everything and this problem is what drives the idea Simina references to connect point value to time. I solve this by using an item itself as the reference value where everyone agrees on its relative complexity as the simplest.

3. All stories should be slim. This means that there should be a limit to the complexity contained within a story. If a story is so complex we want to score it very high on the Fibonacci sequence this is a sign the story should be broken down before we incorporate it into our scored work. This is because there is a high likelihood that a degree of complexity that high would also exceed the delivery timebox of our iteration (e.g. sprint). My rule is I don’t let teams score higher than a 13. If a story is assigned a 13 it simply will be reviewed at backlog grooming for breakdown before it is allowed to enter work-in-progress.

With these points in mind, I have a team follow this process:

In Step #1 - make sure the team agrees on the item that is “simplest”.

In Step #2 - rank the rest of the items in order from the item agreed upon as the simplest to the highest complexity. There are NO POINTS at this stage. Again, achieve consensus on the ranking which ensures everyone’s perspectives on risks and complexity are included.

Finally, in Step #3 - each item is assigned a rank that is either equal to the item before it, or the next value in the sequence if the complexity is greater. The question asked of the team for each item is - will this item be the same complexity or greater complexity as the item we just scored?

During the discussions about complexity the team may try to drift into time. For example - we think this item will take 2 days compared to the item before it which we think is one day or less. Resist these assertions about why an item is complex. Instead ask questions like: what risks do you see? What uncertainty is there in how we will approach this item? What are we learning or defining as we try to deliver this item? This will force the team back into thinking only of complexity to ensure your ranking is validly grounded outside of time.

Once you’ve done this - you and the team are excited. You’ve planned a sprint everyone agrees can be delivered and you didn’t falsely promise time for the items.

But… as a project manager you have a problem… your sponsor and stakeholders will immediately ask you: “when can we expect feature x to be available?”

And you’ll feel tempted to convert those story points into time just like your team was tempted.

Stay strong!

Here’s the tools available to you instead:

1. What’s guaranteed in the timebox is the “Sprint Goal” item(s) or increment. If you aren’t using Scrum, this might also be your project milestone. Only promise this and just promise it at the end of the timebox.

2. Your product roadmap might be able to set expectations with your stakeholders if you are using a Now, Next, Later format as the “Now” items will have an implied delivery meaning (e.g. this quarter).

3. Your feature prioritization may also be able to support expectation management. If you are using MoSCoW, your MuST priorities will have a delivery expectation associated with them at the project level and you can remind people of this promise rather than focusing on the immediate timeboxes.

An interesting read

This week’s interesting read comes to us from Antonio Nieto-Rodriguez and was featured in the January 2026 issue of PM World Journal. Antonio has been a strong voice discussing the reinvention of the project management profession for some time now but this article was a wonderful framing for each of us to center on as we embark into a year where our profession is truly evolving.

My biggest objection to the re-integration of many of the “old” constructs of prior PMBOK’s into the essence of PMBOK 7th edition was that it catered to a philosophy that is holding us back: a focus on methodology instead of mindset.

And while, in the end, the final publication of the 8th edition of PMBOK wasn’t as problematic as I was initially concerned it would be, this attitude prevails in our profession.

Antonio calls this out as:

I loved this article’s honesty about the challenges of assuming Agile is a magic bullet to solve all of our problems. Antonio calls out 4 real challenges that are not solved by agile on its own.

• How to prioritize what we focus our energy on

• How to motivate talent towards the most important work

• Who owns outcomes?

• How to know when to stop something after assumptions change

Antonio calls out exactly what I have seen happen when agile transformations don’t address these structural issues:

Finally, a key revelation the article presents (although it is packed with value beyond what I’ve noted here) is:

And one challenge that we will face this year is this won’t just be a shift in our role towards leadership - it will be a need to educate our fellow leaders and sponsors about the project management capabilities we know are needed for organizational success. By the end of this year I’m quite certain we won’t just need to be leaders, but teachers as well.

If you dive into this read, I hope you’ll share your thoughts as well!

Leave a comment

A tip

It is all well and good for us to say: project leaders need to be more strategic!

But what does that mean exactly?

It might mean you need strategic skills you don’t have.

It might mean you will participate in strategy setting or strategy translation.

It might mean you will be accountable for strategy delivery or implementation.

But these things all have something in common.

They require you to have time.

So the biggest change you need to make isn’t in skill development, or role clarity, or new leadership: it is in making time for yourself to think strategically.

And if you want to dig deeper on this or need tips on how to make this happen in your packed schedule, read this great piece of advice from The Effective Project Manager.

A lesson

This week’s lesson comes to us from a friend of mine who specializes in people management and offers a critical insight into team performance problems that is frequently overlooked in projects and other organizational lenses.

Most project managers learn to step into problems like this through reinforcing accountabilities, increasing oversight, or resetting expectations. But this has the unfortunate side effect of creating pressure on a team that is already struggling. The dysfunction you are actually seeing is beautifully characterized:

Instead of clamping down, pause and take a moment to recognize that what you are seeing is actually an indicator that something has changed. This could be unspoken changes in performance standards; evolving priorities that haven’t been meaningfully discussed; assumptions about understanding; or perhaps even the evolution of the mission overall.

Discover what has changed by asking yourself these questions:

With your answers, approach the team with communication that addresses the clarity gap and performance will recover.

This week I’m loving

This week’s love goes out to Mike Fisher for a great article on the risks of losing track of organizational culture in the hustle to move forward.

I’ve certainly worked with many a startup that didn’t pay a lot of attention to culture early on, favoring the importance of shipping the offering ahead of how people collaborated. It has been my experience that this rarely works.

I loved the analogy in the article that culture debt subtly accumulates rather like technical debt.

I recently wrote on LinkedIn about an experience I had in an early stage startup where the founders led a session deriving company “values” at a company retreat. Of course, saying it and living it are very different things and as Mike points out, a better approach is to recognize that culture will be a living thing within the business subject to regular upkeep.

You’ll notice that Mike doesn’t suggest culture is about who we hire. Something that is a pet peeve of mine, as lately it seems many startups think their corporate values are criteria for filtering candidates. Instead culture should focus on:

• How we work

• What we value

• What we won’t tolerate

• How wide the lane is (what freedom and responsibility look like in practice)

Once these things are settled, you can watch for culture debt to appear by observing three signals:

• When your rewards diverge from what you say you value

• When people are motivated by survival

• When the cost of short-term wins is at the expense of long-term damage

And the real reason behind this?

Culture is fundamentally about decision-making. And when we have culture on a wall and not to guide our decisions, our decision quality tends to suffer.

The solution is deliberate attention paid to culture and Mike defines some habits that ensure you minimize culture debt:

1. Culture is a leadership responsibility (C-suite).

2. Values describe observable behaviors. How do people show up in decisions?

3. Reflection rituals (e.g. retrospectives) are culture maintenance.

4. Ensure honesty is a valued contribution not a risk.

5. Revisit cultural assumptions regularly. Don’t assume what was working is still working.

From the Practice

As you set your professional development goals for the year, here’s some advice from PM Global about where your priorities should lie:

• Judgement over methodologies, frameworks, and tools. Focus on developing your abilities to interpret data, weigh trade-offs and make recommendations even when you face uncertainty.

• You are leading through complexity and communication is your superpower. Develop your assertive communication muscle; practice difficult conversations; and if you haven’t done a course in influencing without authority, make this your top learning choice.

• Cultivate credibility-building behaviors like follow through, preparation, documentation, and proactively closing loops. Become a dependable leader who handles pressure calmly and consistently.

• Mitigate burnout risk by focusing on energy management, attention control, and fostering resilience. Own your calendar in a way that balances time for deep work with meeting loads and define your recovery habits.

• Acknowledge ambiguity and develop your skills to operate without full information.

• Demonstrate professional integrity through ethical awareness and governance literacy.

The good news is these areas for development all mark our growing responsibility and influence and investing in them will drive your 2027 opportunities.

An interesting read

This week’s interesting read comes to us from McKinsey, and was a read where I shouted “yes!” every other sentence.

The topic: creating performance advantage in teams and organizations.

I believe, that generalist PMs, bring this “edge” to organizations because of our big picture thinking abilities. I also think that in the coming years of uncertainty and upheaval in the business world, this “edge” will be a critical differentiator of those who rise and those who fall.

The article uses “transformations” as the use case to describe their observations, but since many transformations are carried out through projects, and many changes are actually transformational these days, I think the point applies more broadly than the article might at first glance imply.

What I especially liked about the article is it calls out that many change management efforts focus on “driving change” rather than on the outcome of change: the behavioral shifts that actually alter how people work, lead, and collaborate.

90% of organizations are focused on at least one of these behavioral themes during transformational efforts:

Image credit: McKinsey & Company, December 15, 2025

These themes are common because they enable organizational health. They are also rewarding because they are related to indicators of engagement.

Fewer than 1 in 3 transformations actually focus on behaviors that move the needle of long-term performance.

Image credit: McKinsey & Company, December 15, 2025

These behaviors were critical to transformation success by creating:

• Disciplined execution that sustained transformation impact

• Accountability to ensure performance is measured

• Performance transparency, motivating sustained performance at new levels

• Improved capabilities through coaching & development of existing team members

• Sharpened decision-making abilities

• Heightened competitiveness

If you are managing a transformation project right now I recommend stopping for a moment and asking: are you building engagement or are you building competitiveness? If your answer is engagement, examine whether you can include some of the blind spot behaviors to deliver true transformation success.

A tip

Fostering strong collaboration is a critical element for project management success. It is a Generalist PM superpower because we are inclined to have strong communication skills and a preference for collaborative problem solving.

But engineering collaboration isn’t something we are taught much theory on.

So this week I’m highlighting some helpful work from Timothy Timur Tiryaki on engineering collaboration. He has a two-part post series on LinkedIn outlining what to look for and how to assess the collaboration maturity you find.

Part 1 covers “Collaboration Zones” which maps collaboration within and across teams.

Image credit: LinkedIn - Timothy Timur Tiryaki

Part 2 covers “Collaboration Maturity” and will help you assess if collaboration in each zone is actually effective. You’ll notice that this is aligned with the levels of psychological safety but may give you different language to support discussing these hallmarks within your organization.

Image credit: LinkedIn - Timothy Timur Tiryaki

A lesson

Calling all Scrum Masters - are you questioning your role right now? In the job market and bewildered by the job descriptions you are seeing? Never fear: Simina Fodor is here with her typically sage advice. I’m putting this here because the lesson within is for every Scrum Master to consider.

I know that all of us are encountering complexity more and more in our project management practice and often it can feel difficult to fully characterize the situation. I’m not the most visually-oriented person but since pictures are worth a thousand words I often try to create visuals to explain abstract things. Complexity certainly fits this bill.

Together, we are now equipped with amazing ability to visualize complexity thanks to this comprehensive resource outlining every possible approach to explaining complexity you could possibly think of. Thanks to a good friend I had the fortune to stumble upon this amazing resource this week, and its a Canadian driven initiative to boot! I hope the team that created it is feeling all the love right now!

From the Practice

With all the recent buzz around value thanks to the revised definition of a project featured in PMBOK 8th edition, I was pleased to see this piece from Dr. Tony Prensa discussing a potential manifesto to help you reposition your PMO around value. I agree with a lot of this philosophy but will be curious to hear how it resonates with you!

Image credit: LinkedIn - Dr. Tony Prensa

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An interesting read

As we begin again in 2026 (and even as we rush to the 2025 finish line) we’ll be making a lot of decisions. Loved this great, and practical, read about making decisions quickly and effectively as a project manager from The Effective Project Manager. No digestion from me, just read it!

A tip

If you work in startup land like me you probably have encountered situations where you get pulled into discussions about funding. Sharing this excellent outline of different funding sources and how to choose between them from Eric Partaker.

Image credit: LinkedIn - Eric Partaker

A lesson

Unfortunately, I know that this time of year can bring “the crunch” and generate a lot of stress for some project managers. This week’s lesson comes from Susan David’s newsletter and discusses how to recognize and manage these waves of stress.

Image credit - Susan David

This week’s love goes out to Alex Smith, author of No Bullsh*t Strategy, and one of my favorite weekly inbox reads.

We know as project managers that we are needing to become more strategic.

We also know, that we don’t get taught much about strategy.

If you want to sound compelling in your strategy conversations, try Alex’s 7 memorable phrases that help you hone in on the 7 essential principles of good strategy.

Image credit: Alex M H Smith - LinkedIn

From the Practice

This week’s From the Practice is in support of all your efforts to plan 2026 including New Year’s resolutions and professional development plans and whatever else you may use for personal growth motivation. The team at PMI Global have put together Actionable Steps to prepare you for success in 2026. I’m sharing these because I think they are bang on. But I’d also like to know, how can the Generalist PM support you in 2026? Let me know here:

If you want something else, pop me a note to let me know your idea!

An interesting read

In PMI land there has been an increasing rhetoric around the relationship between sustainability and projects. Truthfully, this is really just a reflection that many businesses are starting to notice that “business” isn’t as removed from the planet as we might think (unless you actually work for a company whose business is space). According to recent data released by Price Waterhouse Coopers, actually 55% of the world’s gross domestic product (GDP) (about $58 trillion USD) is materially exposed to natural risks. This week’s interesting read dives deeply into what this means for business decision-making and risk management.

Six years ago I was briefly involved in disaster recovery plan development at a health tech company in Canada. Specifically, I supported the initial risk identification efforts and risk plan development as the author of the company’s risk management framework. One of the key risks we identified at the time was our company headquarters dependence on municipal electrical power that relied entirely on a single trunk line that supplied the region we operated within. A mere 4 years later a major forest fire would threaten that very power supply and multiple neighbourhoods as well as a small town around 90 minutes away would be sacrificed, in part, to protect that vital infrastructure. How does a company plan around a risk like this that is entirely outside their control? Some companies simply acknowledge the risk and decide that they can’t mitigate it as they don’t have influence or resources that can directly address this. But, this might not be the only answer. The article gives an example of a company who identified their operations were dependent on water, increasingly in short supply, but that restoring local catchment areas, improving water efficiency, and strengthening nearby ecosystems might be a risk mitigation approach. This is one way that private dollars end up supporting regional sustainable goals.

The key is recognizing that nature isn’t just a stakeholder interest to optimize: it is an integral part of business models in almost every industry.

The article goes on to outline how you might go about this, with a very clear process and a structured action approach once your potential areas of activity have been identified.

A tip

Interested in expanding your horizons from projects into products? If so, you may be excited to learn that the team at Scrum.org has released a self-paced Professional Scrum Product Owner™ Fundamentals course that will help you prepare for your PSPO I exam.

Image credit: Scrum.org

A lesson

This week’s lesson is inspired by a cautionary tale about roadmaps from Janna Bastow. While Janna writes from a product lens, everything she notes is relevant for project managers as well and since many generalist PMs end up in product shoes I think this fits our category well.

First, roadmap is one of the most dangerous words in agile practice, fighting for a top rank alongside “velocity”. The biggest problem is that the word means different things to different people. Sometimes it might be a high-level strategic plan, sometimes it might be a high-level milestone schedule, sometimes it might be an action plan for product evolution. People think of it as a planning tool, a strategic tool, a schedule, or worst of all a series of sales deliverables. It is none of these things in entirety. What it is, regardless of your perspective, is a projection. By nature that means it isn’t a plan or a schedule. A projection is also not a strategy, it is a vision that a strategy might fulfill. If you reframe your “roadmap” as a “best guess” what does that do to how your organization plans or decides next product steps?

The next problem is that because people think of a roadmap as a plan/strategy/schedule there’s enormous and unspoken pressure to perform to this. In some, very misguided organizations, this pressure is real because your sales team is already selling the roadmap to customers. Janna draws brilliant attention to the biggest problem with this:

She urges you to think about the emotional and operational cost of pretending your roadmap is a plan/strategy/schedule rather than a projection.

What are your warning signals?

• Delivery paralysis. Your experienced team has ground to a halt despite the clarity you think you have.

• Your PM is hesitating, uncomfortable. You are asking for answers and getting the run around.

• The team is meeting and meeting and meeting without forward progress.

What is the solution?

Invoke step-wise planning.

What is the smallest possible move that will improve clarity and unlock a decision?

Do that.

Then repeat.

But…you say…how do we satisfy the desire for the roadmap?

My solution is:

1. Use the Now, Next, Later framework (this is actually Janna’s framework). I tend to do this as Now (current quarter), Next (upcoming quarter), Later (rest of all time).

2. Instead of planning “features”, plan the problems you will solve in each window. Your “backlog” should be a list of problems you’ve identified need solving for users and your “backlog refinement” is breaking big problems into smaller problems that can be engineered for. This also, by the way, helps your research team as they have clarity on questions to ask and workflows to investigate with users based on the problem idea you have identified.

This way your sales team and executive leaders still have a vision for where you are going. But now, they help customers understand when their pain points will be addressed and they can inform you of pain points that become more urgent based on customer feedback.

Meanwhile, you’ll probably find that your team finds a new gear of productivity thanks to greater clarity and reduced stress from trying to make your big bets come true.