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Eeke de Milliano

Episode #85

Head of Product

Retool

⚡Execution🎯Product Strategy👥Team & Culture

📝Full Transcript

13,230 words
Eeke de Milliano (00:00:00): Process, by definition, is variance reducing. You're introducing it, because you worry that the variance in your org is too high. You want people to sort of meet a certain standard. Eeke de Milliano (00:00:13): And the cost of that is obviously, while you are reducing the standard and bringing folks up to the average, you're also bringing other folks down to the average. And oftentimes, the folks you're bringing down are your highest performers, your most creative thinkers. The folks who, I think actually don't really need process to do their best work. Eeke de Milliano (00:00:34): And so, that, I think is always the tension that you have with process. And obviously one of the reasons why companies introduce process much more and more, as companies get bigger, is because it's harder to get all these folks who don't need processing. You actually want to reduce the variance. Lenny (00:00:52): Welcome to Lenny's podcast, where I interview world-class product leaders and growth experts, to learn from their hard own experiences, building and scaling today's most successful companies. Lenny (00:01:01): Today, my guest is Eeke de Milliano. Eeke is head of product at Retool. Prior to that, she was a longtime PM at Stripe. She was actually one of their very first PMs, where she helped build some of their foundational products like Stripe Checkout, Stripe Connect, Stripe Radar, and Stripe Chargeback Protection. Lenny (00:01:18): I had a total blast chatting with Eeke. We covered Stripe's internal culture and what makes it so unique and innovative. How to foster and protect innovation at your own company. What is the right amount of process by stage of company? How to build a talent portfolio. And so much more. Lenny (00:01:32): I am really excited for you to hear this episode. And with that, I bring you Eeke de Milliano, after a short word from our wonderful sponsors. Lenny (00:01:41): Today's episode is brought to you by Miro, an online visual wh...

💡 Key Takeaways

  • 1Treat process as a variance reduction tool: use it to raise the floor, but provide escape hatches so you don't lower the ceiling for high performers.
  • 2Implement a 'Crazy Ideas' annual ritual where the prompt is specifically for ideas that have a 90% chance of failing but a 10x-100x return if they succeed.
  • 3Utilize the 70/20/10 resource allocation model: 70% core product (including maintenance), 20% strategic non-core initiatives, and 10% pure speculative bets.
  • 4When building MVPs, 'build the scooter, not the axle.' Ensure the smallest version is functional end-to-end rather than a component of a larger dream.
  • 5Stop hiring in your own image; audit your team every six months to identify gaps in your 'Talent Portfolio' (e.g., visionaries vs. executors) and hire specifically for those missing traits.
  • 6Use the 'Trapdoor' decision framework: Pricing is rarely a trapdoor (you can grandfather users), but titles are (hard to revoke).
  • 7For technical products, build for your best user first, not your worst user. Don't let fear of abuse cripple the initial product definition.

📚Methodologies (3)

⚡ Execution

A philosophical approach to process implementation that acknowledges process reduces variance (both bad and good). It aims to standardize the average while allowing high performers to bypass strictures to achieve exceptional results.

Core Principles

  • 1.Acknowledge the trade-off: Process raises the floor but lowers the ceiling; use it only when variance reduction is the priority.
  • 2.Embed 'Escape Hatches' in templates: Explicitly state at the top of documents (PRDs, specs) that if the template doesn't fit the problem, the author should break the format.
  • 3.Empower managers as gatekeepers: Managers must identify high performers who don't need the process and provide them organizational air cover to bypass it.
  • +1 more...

"Process, by definition, is variance reducing... The cost of that is obviously, while you are reducing the standard and bringing folks up to the average, you're also bringing other folks down to the average."

#minimum#viable#process
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The Crazy Ideas Pipeline

by Eeke de Milliano

🎯 Product Strategy

A structured mechanism to solicit, fund, and incubate non-obvious ideas that would typically be killed by standard prioritization frameworks. It treats the company as a VC and product teams as startups.

Core Principles

  • 1.The 10% Probability Prompt: Create a specific document for ideas that have a 90% chance of making no sense, but a 10% chance of 10x-100x impact.
  • 2.VC-Style Funding: Fund selected ideas with minimal resources (e.g., 1 PM + 1 Eng) for a specific period to prove value before scaling.
  • 3.Organizational Separation: Keep incubation teams separate from the core reporting structure initially to prevent them from getting bogged down in 'keeping the lights on' work.
  • +1 more...

"Crazy ideas are ideas that we shouldn't, obviously, do. There's a 90% chance that they make no sense. But in the 10% chance that they do, they will make a 10x to 100x difference."

#crazy#ideas#pipeline
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👥 Team & Culture

A hiring strategy that treats the team composition like an investment portfolio, seeking a balance of complementary assets rather than uniform excellence in one specific trait.

Core Principles

  • 1.The 6-Month Audit: Every six months, chart the current team to list collective strengths and collective weaknesses.
  • 2.Hire for the Gap: Write job descriptions specifically targeting the identified team weaknesses, not just a generic 'Good PM' profile.
  • 3.Balance Homegrown vs. External: Mix 'Homegrown' PMs (culture carriers, deep product knowledge, non-traditional backgrounds) with 'External' hires (traditional rigor, best practices from other top companies).
  • +1 more...

"I really think that a lot of product management can sometimes be reduced to funnels and portfolios... Instead of having a bunch of PMs who all spike in one particular area, figure out how you can create complimentary skillsets."

#product#talent#portfolio
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