Personality and “strength” tests at work have never sat right with me.

Why organizations are often more diverse in belief than they appear to be in behavior

Life update!

Everyone is talking about “return on tokens.” Vendors love it (as long as the news is good).

I had a friend reach out recently for advice. I started writing...

If what you are mapping is incoherent, don’t fall in love with the map (or your personal ability to navigate with it).

Last week, things got super heavy with a post about identity, thriving, and figuring out how to navigate the workplace (when you love your work).

This post is important.

AI can be your scribe, your thought partner, data-stitcher, or your counselor.

My goodness.

So you want your team to figure out how to use AI for the benefit of your company?

I have been thinking a lot about self-care, especially for people who find themselves pulled into helping people and making things better. The desire to help can be a gift. It can make you notice pain...

This post is about the people who built the fiefdoms now looking to AI to save them from the fiefdoms, and why that will only work if we are honest about what those fiefdoms were built to avoid in the...

It has driven me to some “back to basics” thinking. One model I’ve been playing with lately is the triad of Exception, Presence, and Delegation. The ideas aren’t new, but it has sparked some good conv...

YouTube video by Rise8

...and the journey of self-awareness we are all going through

A skill that efficiently recommends posts from The Beautiful Mess - johnpcutler/tbm-recommender

I guess I’m putting together an AI series of sorts.

(Sometimes I get excited by a topic and write more than once a week.

A seven-step behavior diagnosis framework for organizational change, built on COM-B, BCW, BCTs, and original diagnostic lenses. - johnpcutler/change-lenses-and-actions

There is a big difference between legibility and legitimacy.

In my day-to-day work (at Dotwork), I hear about all the real-world exceptions, “things that work,” “things that never work” (but we keep trying), and everything in between. I’m a big fan of saying, “...

But I’d reframe it slightly. The work of product leadership isn’t simply defining the problem and handing it to the team. It’s creating the conditions where people can engage with the situation from m...

(I used to do more of these visual build posts.

Here’s a simple model I’ve been using lately to discuss strategy and focus.

AI is supercharging legacy leadership assumptions about context and control.

This essay is about hope, fear, AI, and the tension between control and collective sensemaking.

I made a simple tool to help make sense of a new team, group, or company: https://johnpcutler.github.io/team-association/ .

A story in five acts...

Hey again! Welcome back to part two of me reflecting on the past few quarters and writing down my answers to John Cutler and Tom Kerwin’s questions on how...

I was in a discussion recently about Strategic Portfolio Management (SPM), and I asked what turned out to be a surprisingly uncomfortable question: if the people responsible for strategic portfolio ma...

Happy 2026, and thank you for reading the newsletter!

Nearing the big 400!

I created this graphic a couple weeks ago.

It’s all bets, opportunities, and BAU until someone loses their job.

So much becomes clear when you actually label the relationships between things. It’s something I do every day, and I do it very naturally. But it is not something everyone does naturally.

YouTube video by The Beautiful Mess-John Cutler

In the past, I have used the term “functional feature factory” to describe a somewhat nebulous concept. The basic idea I was trying to convey was twofold: There’s a middle ground of product-centricity...

I’ve been thinking a lot about why some people are wired for concrete solution-thinking while others naturally gravitate toward more abstract, problem-focused, or strategy-level thinking.

"My company has a highly detailed process involving project codes and program codes, tracking time, highly detailed (and premature) estimates, and lots of very precise reporting with dollar figures do...