How to foster innovation and big thinking | Eeke de Milliano (Retool, Stripe)

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Eeke de Milliano is the Head of Product at Retool and a former product lead at Stripe. In this episode, we discuss how any team can become an innovation machine. We talk about how a culture of writing led to a team of rigorous thinkers at Stripe. We cover tactics to breed innovative teams that you can replicate at your own company: From embracing retrospectives to creating systems that give individuals the "permission to think big". Eeke shares her framework for prioritizing resources between core products, strategic initiatives, and big bets, and how it helped Retool launch three new products in a year. She also gives a comprehensive overview of the right level of process for companies of different sizes, and how to build a talent portfolio.

Listen now on Apple, Spotify, Google, Overcast, and YouTube.

Find the transcript for this episode and all past episodes at: https://www.lennyspodcast.com/episodes/. Today’s transcript will be live by 8 a.m. PT.

Where to find Eeke de Milliano:

• Twitter: https://twitter.com/eekedm

• LinkedIn: https://www.linkedin.com/in/eeke-de-milliano-3b05a629/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• Twitter: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

Referenced:

• Snir Kodesh on LinkedIn: https://www.linkedin.com/in/snirkodesh/

• Stripe: https://stripe.com/

• Stripe’s operating principles: https://stripe.com/jobs/culture

• Retool: https://retool.com/

• Brian Krausz on LinkedIn: https://www.linkedin.com/in/bkrausz/

• Retool Workflows: https://retool.com/products/workflows/

• Retool Mobile: https://retool.com/products/mobile

• Retool Database: https://retool.com/products/database

• Ian Leslie on “Being Human in the Age of AI”: https://www.econtalk.org/ian-leslie-on-being-human-in-the-age-of-ai/

• Claire Hughes Johnson on LinkedIn: https://www.linkedin.com/in/claire-hughes-johnson-7058/

• Scaling People: Tactics for Management and Company Building: https://www.amazon.com/Scaling-People-Tactics-Management-Building/dp/1953953212

• Linear: https://linear.app/

• Bird by Bird: Some Instructions on Writing and Life: https://www.amazon.com/Bird-Some-Instructions-Writing-Life/dp/0385480016/

• Lex Fridman Podcast: https://lexfridman.com/podcast/

• EconTalk: https://www.econlib.org/econtalk/

• The White Lotus on HBO: https://www.hbo.com/the-white-lotus

• Gong: https://www.gong.io/product-demo/

• FullStory: https://www.fullstory.com/

• Rewind: https://www.rewind.ai/

In this episode, we cover:

(00:00) Eeke’s background

(03:36) Eeke’s time at Stripe

(08:58) Why Stripe didn’t add PMs until hitting around 100 employees

(11:03) Why being a PM is not for everyone

(12:22) Stripe’s internal culture guide

(17:36) Stripe’s operating principles 

(20:52) Why isn’t every team innovative?

(23:21) Retool’s “crazy ideas” list 

(27:27) How to cultivate a failure-safe space 

(28:47) Fostering risk-taking and innovation

(32:03) The three products Retool launched this year

(35:06) How Retool was able to launch several products at once

(38:00) The amount of process needed through different stages of growth

(45:37) Why you should build products for your “best users”

(47:34) Build the scooter, not the axle (why you should make something simple but functional first)

(48:37) The 70-20-10 framework for investing resources and time

(49:57) Finding time for maintenance and bug fixes

(50:59) How Retool’s PMs keep close to customers

(53:29) Building product in a sales-led org vs. product-led growth 

(56:10) The product talent portfolio: how to build diverse, balanced teams

(58:43) Lightning round

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