How to foster innovation and big thinking

Eeke de Milliano, head of product at Retool and a longtime PM at Stripe (where she was one of the first PMs), discusses how Stripe's culture of rigorous thinking and writing shaped its innovation. The conversation also covers fostering big thinking, the tension between process and creativity, team structure for new products, and building a balanced product talent portfolio.

01Key learnings

• Process reduces variance but can pull down top performers; introduce it deliberately and give high performers escape hatches, such as a 'minimum viable process' with an explicit option to go beyond templates.
• Reframe failure as learning: rename postmortems 'retrospectives' and have people share failure learnings publicly to normalize risk-taking.
• Lower the stakes of big bets by using small teams, getting customer feedback early, and not waiting for perfection before testing.
• Give teams explicit permission to think: include a 'Think Bigger' section in team charters asking what they would do with 20% more time or a doubled team.
• Run a company-wide 'Crazy Ideas' doc each year; Eeke says a few of these ideas typically get built, and two of Retool's three launched products started there.
• Start new products small (one engineer and one designer), fund them only once there is evidence of value, and run them as startups that must prove ROI.
• Build for your best users rather than your worst, and ship a 'scooter' (a smaller, complete slice of value) before the full vision.
• Hire to balance your team's strengths and weaknesses, and build a talent portfolio that mixes homegrown culture carriers with people who bring outside product rigor.

02Frameworks mentioned

Summary and takeaways written by PM Atlas; quotes are short excerpts. © the original author.