Feb 2, 2023 · 1h 2m · lennys-podcast
How to foster innovation and big thinking | Eeke de Milliano (Retool, Stripe)
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode, Lenny Rachitsky interviews Retool Head of Product Eeke de Milliano on the operational playbooks, first-principles culture, and minimum viable processes needed to drive big-thinking innovation and high-performing product teams.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Lenny holds 27.8% of the talking time here. How this is scored →
Lenny as informed peer 3.3 Guest teaching 4.3 Guest disagreement 0.6 Lenny pushing back 0.2
speaking balance: gold is Lenny, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 21:43 Eeke reframing the innovation inquiry
Eeke actively inverts Lenny's question from why top companies innovate to why most teams naturally default to incrementalism.
Hardest push from Lenny ▶ 47:00 Lenny challenging best-user vs worst-user focusLenny pushes back on Eeke's advice to ignore worst users, pointing out standard optimization frameworks that prioritize marginal users in funnel flows.
Biggest teaching moment ▶ 39:40 Eeke's masterclass on process as variance reductionEeke breaks down the trade-off of corporate process, explaining that raising the floor drags the highest performers down to the mean.
Lenny holds their own ▶ 49:10 Lenny comparing resource allocation frameworksLenny directly benchmarks Eeke's 70/20/10 split against his own established product management heuristic on maintenance and bets.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Lenny as informed peer | Guest teaching | Guest disagreement | Lenny pushing back | Why |
|---|---|---|---|---|---|---|
| From Sales to Product: Early Days at Stripe | 2 | 3 | 0 | 0 | Lenny sets up the foundational questions regarding Eeke's background at Stripe, and Eeke provides detailed context on transitioning from early sales to building core products like Stripe Connect and Radar. | |
| Why Developer Tools Resist Product Managers and When to Hire Them | 4 | 4 | 1 | 1 | Lenny notes the industry narrative around developer-tool companies resisting PMs. Eeke reframes this with practical nuances about how expanding customer archetypes and cross-functional complexity necessitate PMs. | |
| Stripe's Internal Culture, Rigorous Thinking, and Writing | 3 | 5 | 1 | 0 | Eeke explains Stripe's writing-centric culture, rigorous decision-making, and two-way vs one-way door framing, correcting common assumptions like treating pricing as a trapdoor decision. | |
| Operationalizing First Principles and Stripe Operating Principles | 4 | 4 | 0 | 0 | Lenny connects Stripe's principles to Airbnb's cultural mechanisms, while Eeke elaborates on Stripe's operating principles like 'micro-pessimists, macro-optimists.' | |
| Overcoming the Fear of Failure and Fostering Big Thinking | 3 | 5 | 1 | 0 | Eeke flips Lenny's premise from why some teams innovate to why most default to incrementalism, explaining psychological barriers, operational friction, and structural permission to think big. | |
| Tactics for Cultivating Audacious Ideas and Safe Failure | 3 | 4 | 0 | 0 | Lenny questions how to move beyond superficial ideation, and Eeke describes concrete methods such as Retool's 'Crazy Ideas' annual doc and the 'Think Bigger' section in team planning charters. | |
| Sponsor Message: Eppo Modern Experimentation Platform | 3 | 5 | 1 | 0 | Lenny asks about Retool's launch of three products in a single year; Eeke shares candid retrospective critique regarding sequencing and operational isolation of early bet teams. | |
| Minimum Viable Process and the Core Planning Documents | 4 | 6 | 1 | 0 | Eeke delivers an articulate analysis on how process reduces organizational variance at the expense of high-performing outliers, outlining the three essential planning docs and MVP frameworks. | |
| Breaking the Org for Exceptional Talent | 5 | 4 | 1 | 1 | Lenny compares investment breakdowns and resource allocations with his own heuristics, while Eeke outlines 'breaking the org' for exceptional talent and building for best users. | |
| Staying Close to Customers and Dogfooding at Retool | 3 | 4 | 0 | 0 | Eeke highlights Retool's tactical customer proximity practices, including shared customer Slack channels, technical PM hiring, and deep internal dogfooding. | |
| Aligning Product with Sales and the Science Fair Model | 3 | 4 | 1 | 0 | Eeke rejects a rigid dichotomy between product-led and sales-led growth, proposing bidirectional interaction models and a science fair approach for GTM alignment. | |
| Building a Balanced Product Talent Portfolio | 3 | 3 | 0 | 0 | Eeke wraps up the main discussion by outlining the 'talent portfolio' framework, detailing how to audit team skill sets biannually to counter managerial pattern-matching bias. |
Statements from this episode (28)
Aspiring product managers should start their careers in sales
“And to this day, when people ask me, hey, like, what's your advice for going into product management? I'm like, well, you should go get a sales job. I think it's like pretty, pretty valuable.”
Stripe hired its first product manager at around 100 employees
“I think we actually had our first PM at, I want to say about a hundred employees.”
Early developer tool startups do not need product managers
“I think actually both in the Stripe case and the Retool case, the thing that both of these companies have in common is you're building for developers. The people who are building the product are the customers in a lot of ways. So like they get it, you know, th…”
Developer tool companies need PMs when their customer segments diversify
“The moment at which it became clear, like we really do need PMs at Stripe. And I think we felt the same way at Retool is your customer base starts expanding. You start having different kinds of customers. You need to understand Sort of the whole market, all of…”
Pricing isn't a trapdoor decision because existing users can be grandfathered
“I think a lot of people, for example, think pricing is a trapdoor decision, but actually like it's really easy to grandfather your existing users into some existing pricing model and change pricing for future users.”
Job titles are trapdoor decisions because they cannot be revoked easily
“Once you've given someone a title, you can't really take it away. So, you know, you better be damn sure about, you know, the title you want to give someone.”
Company 'operating principles' are more effective than personal 'values'
“Stripe would call them operating principles, actually, which I think is actually better, because values is almost like, you can't really tell people what to value, like everyone has their own value set, but you can tell people like, hey, here's, Here's how we …”
High performers pair macro-optimism with micro-pessimism on details
“Micro-pessimists, macro-optimists. Yeah, it was just like this idea that like long, in the long term, we expect the curve to go up. Like, we believe, like, you know, we very much believe in the upward trajectory of just about everything, but like, on the sort …”
Milliano: Leaders want innovation's upside without accepting necessary failures
“Leaders want the upside of innovation, but they're not really willing to deal with the cost of innovation, which is like, look, if you're going to swing big, you will invariably stumble sometimes.”
Retool product charters include a 'Think Bigger' section for ambitious ideas
“At a retail, we have these team charters, and we do team planning, and at the bottom of every team charter, we have a section called Think Bigger with, you know, 20% more time. What would you do that isn't on this list already?”
Retool's CEO circulates an annual 'Crazy Ideas' document for 10x bets
“Another really neat tradition that we had at Stride, we have a retail now too, is this idea, this thing called crazy ideas. So at the beginning of every year, David will send out a blank Like a blank doc to the org, and it's titled Crazy Ideas, and the prompt …”
Retool ships three to eight items from its crazy ideas document annually
“Every, so every year that we send out the doc, we look at the past year, the doc from the past year and we're like, okay, like, What did we do anything on this list? And like consistently we do anywhere between like three to eight things on the list.”
Retool Workflows originated on the company's internal crazy ideas list
“So that was actually one of the crazy ideas and that ended up becoming Retool Workflows, which, you know, we launched just last year in November.”
Product teams default to planning for existing headcount rather than ideal scope
“Like, I think you kind of end up planning towards the sort of the team that you have, not the team that you should have.”
Retool incubates new product bets with one or two people for months
“We started really small with all of these initiatives. So, you know, I think I mentioned we really had one or two people working on, on each of these products for like the first six months. So it was like one engineer and one designer or one engineer and one P…”
Retool separated new product teams to avoid core product-market fit drag
“And we eventually decided that we were going to run it as a separate team because we wanted the team to be able to move really, really quickly. And we didn't want it to get bogged down in what are just the realities of running a product that has product market…”
Process is variance-reducing and pulls down an organization's highest performers
“Process by definition is variance reducing. Like you're introducing it because you worry that the variance in your org is too high. Like you want people to sort of meet a certain standard. And the cost of that is obviously is like while you're reducing the sta…”
De Milliano adds escape hatches to organizational templates to prevent rigidity
“So I've started referring to this as like the MVP, the minimum viable process. So if I give folks a template, I'm like, look, use the template, but if you want to break out of it, please absolutely do. And like, Start writing this at the top of templates now. …”
Every team needs three documents: a charter, goals, and a roadmap
“There's just a set of documents that are like really, really viable that every sort of like, I guess, level of the organization should have throughout its life cycle. And then, you know, I think how sort of involved it is or how, like, long term it is really d…”
Managers must give high performers air cover to bypass standard process
“To me, the unlock for organizations is managers. For this. Because like, you need managers to both detect the high performers and be like, this person doesn't need the process. And then you need managers to give that person air cover to be like, we're honestly…”
Product teams should build for their best users, not worst users
“Build for your best user, not your worst user. And what I mean by that is, I think it's actually really easy to kind of get stuck or to sort of focus on like, what if there's abuse of this product or think about all the ways in which the product won't be used …”
Allocate product resources 70-20-10 between core, strategic initiatives, and bets
“The 70, 20, 10 investments model in my head is just like, 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 core, but like they're strategic …”
Every Retool product manager has a CS degree or engineering background
“Like our PMs are really very technical. Like everyone has, you know, either a CS degree or has done some sort of engineering. In the past.”
Retool builds its product roadmaps and feature flagging directly inside Retool
“We use Retool to build Retool. So our product roadmap lives in a Retool app and the app that we use to, you know, to have feature flags for particular features is a Retool app. So PMs are just in the product all day long, every day. They're their own customers…”
Product-led and sales-led companies constantly envy each other's go-to-market motions
“Teams that have one always want the other. Like whenever, whenever I talk to candidates, I feel like you can always tell what, you know, their company has because they'll be asking a lot of questions about the opposite. Like they're probably like growth compan…”
Retool pilots an internal science fair to align product and go-to-market teams
“This year we're actually trying something different. We are doing a science fair. Where each product team has a little booth and they get to sort of stand there and anyone who has questions about the product can come, you know, from the go to market side, can …”
The best product teams build complementary talent portfolios over homogeneous spikes
“I think it's really tempting as a manager to build a team in your image because you understand their skillsets and you value those skillsets and you're going to be able to detect and assess those skillsets better. But the best product teams in my mind have rea…”
De Milliano audits team skill gaps biannually to hire for specific weaknesses
“I do a little personal exercise for myself every six months where I, like, sit, like, sort of chart out the team that we have today and, like, write down all the strengths that we have, all of the weaknesses that we have as a team, and then I try to sort of hi…”