John Cutler
John Cutler writes the popular and beloved product newsletter The Beautiful Mess. For many years, he was a Product Evangelist at Amplitude, which led him to meeting and working with a large number of product teams around the world. Through this role, he gained unique insight into how the best product teams operate.
AI & Technology Skills
LLMs are highly effective tools for perspective-taking and de-biasing by simulating how different worldviews would interpret a single business problem.
"I like the ChatGPT thing because I like having things, having a developer inspired by Hemmingway debate, a developer inspired by Tolstoy... you can actually make it do really funny things. And back to..."
Growth Skills
Deep expertise in retention and engagement is built through massive, iterative research projects that combine customer success insights with product management.
"Our CS team developed 110-page bulk of research from working directly with customers around retention engagement, then we had a PM and a great content writer, Archana, zero in and kind of make it pala..."
Hiring & Teams Skills
Asking candidates to narrate a situation from a colleague's perspective is a powerful way to gauge their self-awareness and empathy.
"Imagine I'm interviewing a person you worked with. Now answer in there, tell me about of the same situation... what was that story from the perspective of one of the people you worked with? I think it..."
High-performing hiring processes focus on de-biasing decisions through standardized 'bar raisers' and explicit job-linked standards.
"I was just reading that working backwards book about Amazon and they're in this chapter about basically their bar raisers thing and I share it with my partner who's the head of HR at a company. She's..."
High performance is a result of 'coherence' where the organizational structure, incentives, and technical architecture all align to support the business strategy.
"The first thing you notice is the companies that are very high performing have coherence between the structure of their company and their current strategy. This is a structural thing... Their funding..."
Values like 'ownership' are meaningless without defining the specific behaviors that manifest those values within the company's specific cultural context.
"Ownership defined in an individualistic culture is going to look very, very different than ownership defined in a collectivist culture. What I find with companies is that... they're just like, 'Well,..."
Leadership Skills
There is no single 'best' decision process; high-performing teams succeed by choosing a process (rigorous, collaborative, or top-down) that is coherent with their leadership and culture.
"The better teams make high, better decisions faster... Company A buys into the whole idea of an extremely rigorous decision-making process. It's very process driven... Company B, maybe they're just al..."
Effective decision-making requires first identifying the type of system you are operating in (clear, complicated, complex, or chaotic).
"There's things like that out there. There's this thing Cynefin, which is a way to understand the systems and decision-making problems have, are you dealing with a clear system, a complicated system, a..."
Product leaders must distinguish between what 'can' be done (feasibility) and what 'should' be done (strategic value) to avoid being trapped by pragmatism.
"In some environments there's this should/can divide... some people are just locked into the can. They're uber pragmatic people... And then there's people who for some reason go in and say, 'Should we..."
A significant portion of the transcript is dedicated to the specific skill of 'nudging' legacy or non-Silicon Valley companies toward modern product practices without causing systemic rejection.
"Most of those companies need to think of frameworks appropriately... they see adopting the frameworks as the end goal."
Product Management Skills
North Star metrics are most effective when treated as a qualitative model that helps teams align on value before adding measurement.
"I wrote the North Star Playbook in partnership with Jason who was a co-writer with that. We did a lot of one-to-one coaching sessions. I had these things called product therapy sessions when I would j..."
The North Star framework serves as a qualitative model that bridges high-level strategy with specific measurements.
"In Amplitude, we have this data informed product loop that we would teach, and it's basically, you need a strategy, you need to develop qualitative models, you need to add measurement to those models...."
Product success is a cumulative 'layer cake' of strategic decisions made years in advance, rather than just recent actions.
"The Jeff Bezos thing, that the success of today was set in motion three years ago, that product is a layer cake and that you are layering on decisions, the success you're having now is a layer cake of..."
Universal techniques like Opportunity Solution Trees provide a standardized way to define problems and explore solutions regardless of company size.
"There's the people like Teresa Torres and others that have come up with a technique that is universal. You can teach an element of product thinking with her techniques or this opportunity solution tre..."
The primary driver of team improvement is 'reps'—the frequency of completing the full cycle of shipping, measuring, and learning.
"In many of those companies, they should focus on creating these sort of areas or pods where a company can, a team can get in the reps that they're trying to be able to do... Shipping and learning, goi..."