Lessons from John Cutler

On Product Management and Strategy

"Most 'source of truth' problems in product development aren't really about the source of truth at all. They assume that everyone wants the truth, that they can agree on what truth they're seeking, and that they're willing to put in the work to forge coherence when there are different versions of the truth." [1]
"What matters is coherence and shared understanding…being able to link the narrative between bets." [2]
"Often, efforts to simplify this beautiful mess just distract us." [2]
"Too many companies get worked by tools instead of making tools work for them." [3]
"A product manager is C-a-a-S... context as a service... it's not translator as a service." [4]
"Any developer working down here should be able to tie what they're doing to the bets that matter up here in a coherent way without sort of making it up as you go along." [4]
"I've always seen product as sort of a creative activity with a bunch of people who are very passionate about what they're doing who care about it having an impact." [4]
"The PM's job is recontextualizing the same core bit of data in dozens of ways." [5]
"You can think about work just in terms of time... 1 to 3 hours 1 to 3 days 1 to 3 weeks 1 to 3 months 1 to three quarters 1 to 3 years and 1 to three decades." [5]
"I've been at this a while, and I'm usually right, like 98% of the time, but being right is rarely helpful." [3]
"When a product team is truly aligned around an outcome, it becomes harder and harder to tell a simple story to explain why they are successful." [2]
"Bets can take many forms. Bets are small and large. Bets are risky and safe." [2]
"Often, risky exploratory bets are followed by more prescriptive and certain bets." [2]
"At any given time we have 1–3 hour bets linked all the way up to 1–3 decade bets." [2]
"When times are good, companies develop a mix of good habits and bad habits. When times get tough, they can no longer get by with bad habits." [6]
"Good product people know that lifting a model from another company without understanding the underlying conditions is risky. That's systems thinking." [1]
"The second we ask for any kind of visibility they push back. The second we ask for a timeline they push back. I understand! I was like that. But this is non-trivial." [6]
"You can have a really complex problem and you can oversimplify it and that's not great but you could have a complex problem and be like you know what I need to hold some things constant." [7]
"I just wish people could just maybe even lean into the theater i mean just have a big block on your road map that says pending the strategy reset." [5]
"Everyone argues about you know uh problems versus solutions or output or uh you know outputs and outcomes and all that it's all there no matter what you do." [5]

On Goals and OKRs

"To me, OKRs are goals. And you know what? Goals are hard." [1]
"Companies somehow believe that OKRs, alone, will magically solve the problem of goal setting. They help... But still, goals are hard." [1]
"What pains me is that you see teams adopt OKRs and assume these are the only goals you need to set?! Goals are everywhere. Goals are pure intent." [1]
"Product work is filled with intent—from the tasks we hope to complete today, all the way through to how we might want to change a vertical or solve extremely complex customer problems." [1]

On Metrics and Measurement

"This is why story-point velocity, in my opinion, is a faulty metric, but that measures of rapid learning, rapid experimentation, impact, and rapid integration are helpful." [2]
"A VP of Engineering friend of mine shortens a team's sprint to one day when they've had trouble working small. Is this one day cycle time? Did they suddenly improve? Good question!" [2]
"The irony is that if we evolve product teams to where we want them to be…we'll actually be less, and less able to identify 'chunks' of work. It becomes more continuous and adaptive." [2]

On Organizational Culture and Dynamics

"In these companies, there is a knee-jerk reaction to anything that suggests things are harder than they appear. There is a veneer of simplicity, and any suggestion otherwise is quickly tamped down." [1]
"These companies often reject nuance outright because it threatens the narrative of control and efficiency." [1]
"Leaders: 'But why didn't you tell us that? No wonder things are going so slow!' Managers: 'We tried, but then you asked us to simplify! You told us not to make excuses!'" [1]
"Leaders: 'It is your job to push back! Why didn't you escalate this?'" [1]
"Eventually, the dust settles. Teams scramble to repackage the truth. A new format emerges. A cleaned-up view... And so it starts again. The cycle repeats itself." [1]
"It's like when someone finally tries to get organized. They list out everything... The raw, unfiltered truth. It's overwhelming. So they clean it up... For a while, it works. The simplified version feels good. Manageable. But slowly, it drifts from reality." [1]
"You are threatened. They are threatened. You'll have to work through it." [6]
"Discussions about productivity are extremely tiring for all the reasons mentioned above, and you might save your brain and heart for something else." [6]
"There's a big difference between resignation and contextual awareness." [1]
"There's a lot of who. I think you could draw some broad boundaries around for example the people who are involved in making the thing." [5]
"There's so many directions of management there's management up there's management up and diagonal there's manage to the side where you're managing your peers there's managing down diagonal you're managing the people who work for your peers you're managing the people who work for you you're managing out to the customers in the world you're managing out to the partners in the world you're managing to the general company investors that you're doing." [5]
"I think that one of the big questions for companies is how much to actually engage with customers themselves." [5]
"You just have to be aware of your company rhythms and where these things fit in." [5]
"Map the company calendar like what happens it's like every August People seem to be surprised that we're going off into strategy season every October seem people seem to be surprised that there's another budget cut yet it happens every single year." [5]
"The biggest source of waste is not low performers or having too many employees." [6]
"They say we're now in 'war-time', but that assumes we were in 'peace-time'. We weren't: we were in crazy-time. And we were raising these flags the whole time!" [6]
"I get the empowerment thing, but there is a level of hubris here on the part of our product managers." [6]
"It pays for us to help to try to unravel that as we think about our work." [5]

Learn more:

Lessons from John Cutler

On Product Management and Strategy

On Goals and OKRs

On Metrics and Measurement

On Organizational Culture and Dynamics

Written by Antoine Buteau

Lessons from Bob Fifer

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