Eeke de Milliano

A strong writing culture forces clear thinking and rigorous analysis across the organization.

"Stripe had a very strong writing culture. All communication was along from writing business reviews, strategy memos, product reviews... I don't think you can be a good writer, unless you're a clear th..."

A 'Science Fair' format allows for more interactive and deep-dive alignment between product and sales than a standard roadmap presentation.

"We are doing a science fair. Where, each product team has a little booth. And they get to stand there, and anyone who has questions about the product can come... from the go-to-market side, can come a..."

Unaddressed tech and product debt acts as a ceiling on a team's ability to innovate.

"Sometimes teams are just getting bogged down by really urgent work. There's too much tech debt. There's too much product debt. Bugs, instability... There's just no way that they're going to be able to..."

Asking candidates to explain their success without citing luck reveals their level of self-awareness and first-principles thinking.

"To what do you attribute your success? And you can't say luck... I always kind of wanted to know, 'How self aware are you, and how curious are you?'"

Build a 'talent portfolio' by balancing internal 'culture carriers' with external hires who bring different professional rigors.

"I really like to balance product teams with homegrown product managers, who really get the product... with product managers who've come from other companies, and have done it, and can bring a little b..."

Use a culture guide during the hiring process to attract candidates who align with your specific operating style and deter those who don't.

"We actually wrote it to share with candidates. Because the idea was like, 'Look, we're kind of opinionated about how we do things here. Most companies struggle to describe what their culture is... our..."

Balance long-term optimism with short-term critical thinking to ensure high-quality execution.

"Micro pessimists, macro optimists. It was just this idea that, 'In the long term, we expect the curve to go up. We very much believe in the upward trajectory of just about everything. But on the day-t..."

High-performing individuals may require 'breaking' standard organizational processes or structures to allow them to do their best work.

"Claire, who used to be the COO of Stripe, would always say, 'Are you willing to break the org for this person?'... some people are just that good that like, 'Yeah, of course you'll break the org for t..."

Distinguish between reversible (two-way door) and irreversible (one-way door) decisions to maintain velocity.

"Is it a trapdoor decision? Which I think is an Amazon concept. One-way door, or two-way door... Stripe was actually really good at being rigorous... about what actually was a trapdoor decision."

Reframing post-mortems as retrospectives helps normalize failure and focuses the team on learning rather than blame.

"Instead of calling something a postmortem, call it a retrospective, so that it's a positive thing. Like, 'Hey, we're learning from this thing.'"

Publicly celebrating the learnings from a failure reinforces a culture of innovation and psychological safety.

"Have people talk about the failure in these sort of public forums, where usually you talk about the successes. So have someone actually write a note that's like, 'Hey, here are all my learnings from t..."

A low-stakes, company-wide 'Crazy Ideas' document can surface high-leverage opportunities that standard planning misses.

"Crazy Ideas... David will send out a blank doc to the org and it's titled Crazy Ideas. The Prompt is, 'Crazy ideas are ideas that we shouldn't, obviously, do. There's a 90% chance that they make no se..."

Explicitly asking for 'big ideas' in planning documents prevents teams from only focusing on incremental improvements.

"At the bottom of every team charter we have a section called, Think Bigger. 'With 20% more time, what would you do that isn't on this list already?'"

Use a portfolio approach to resource allocation to balance core maintenance, strategic growth, and high-risk bets.

"70/20/10 investments model... 70% of your building time should really be going to your core product, that has product market fit. 20% of your time should be going to strategic initiatives that aren't..."

Every team should maintain three core documents: a charter, a set of goals, and a roadmap.

"Those documents, to me, are the charter: 'What is your mission, your vision and your strategy?' The goals: 'What are you aiming to do and how are you going to measure success?' And then the roadmap: '..."

In early product development, optimize for the 'power user' or ideal customer rather than getting bogged down by edge cases or potential abuse.

"Build for your best user, not your worst user... you shouldn't really be building for them. I think a really good example of this is onboarding processes... Really, you should just be building an onbo..."

An MVP should be a functional, end-to-end version of a smaller value proposition, not an incomplete piece of a larger one.

"Build the scooter, not the axle. So if you're trying to build the minimum viable product for a car, don't build just the wheels and the axle, build the scooter first. And then from there, you build th..."

Direct, informal communication channels like Slack provide faster and more honest feedback loops than formal surveys.

"We use Slack very heavily to talk to our customers... we have hundreds of Slack channels with customers. Every time we're testing a new product... We will work with them in Slack, to get there off-the..."