How to foster innovation and big thinking | Eeke de Milliano (Retool, Stripe)
Eika Demigliano, Head of Product at Retool and former Stripe PM, discusses fostering innovation, the right amount of process for company stages, Stripe's unique culture (rigorous thinking, writing, decision-making), and building a product talent portfolio.
Deep Dive Analysis
14 Topic Outline
Eeke de Milliano's Journey: From Sales to Product at Stripe
Stripe's Unique Culture: The Role of PMs and Rigorous Thinking
Stripe's Operating Principles and Decision-Making Philosophy
Why Teams Struggle with Innovation and How to Overcome It
Cultivating a Failure-Safe Space and 'Permission to Think Big'
Retool's 'Crazy Ideas' Initiative for Fostering Innovation
Launching Three New Products at Retool in One Year
Strategies for Rapid Product Development with Small, Independent Teams
The Right Level of Process for Different Company Stages
Product Building Philosophies: Best Users and 'Scooter, Not Axle'
The 70-20-10 Framework for Product Investment and Maintenance
How Retool's PMs Maintain Close Customer Relationships
Product Building in Sales-Led vs. Product-Led Organizations
Building a Balanced Product Talent Portfolio
6 Key Concepts
Process as Variance Reducing
Introducing process aims to reduce variance in an organization, bringing people up to a certain standard. However, the cost is that it can also bring down high performers and stifle the creativity of those who don't need rigid processes to do their best work.
Trapdoor Decision
An Amazon concept referring to decisions that are irreversible or very difficult to undo. These types of decisions require rigorous thought and careful consideration because you cannot easily go back on them once made.
Micro Pessimists, Macro Optimists
An operating principle at Stripe that encourages critical thinking and attention to detail in day-to-day decisions, focusing on potential issues and how things might not work. Simultaneously, it maintains a belief in a long-term positive trajectory and upward growth.
Permission to Think Big
Creating specific moments and cultural elements within a company where employees are explicitly encouraged and given dedicated time to think creatively and strategically beyond urgent, day-to-day tasks. This helps counteract the tendency to get bogged down by incremental work.
Build the Scooter, Not the Axle
A product development philosophy that emphasizes building a simple, functional, complete product (like a scooter) that delivers immediate value, rather than just components of a larger, more complex product (like an axle for a car). The idea is to get a viable, end-to-end experience to the customer quickly.
Product Talent Portfolio
A management approach to building product teams by balancing diverse skillsets and backgrounds, rather than hiring people who all excel in the same area. The goal is to create a complementary team where the whole is much stronger than the sum of its individual parts.
6 Questions Answered
Stripe, and similarly Retool, built products for developers, meaning the engineers building the product were often the customers themselves and understood their needs. PMs became necessary as the customer base and organizational complexity expanded.
Stripe fostered a culture of rigorous thinking, a strong writing culture (believing good writing indicates clear thinking), and a focus on quickly making reversible decisions while being rigorous about irreversible ones.
To foster innovation, companies should mitigate the fear of failure by normalizing it and learning from it, address urgent work that bogs down teams, and explicitly give teams 'permission to think big' through cultural practices like 'crazy ideas' lists.
Process reduces variance, bringing average performers up but potentially stifling high performers. Companies should aim for 'minimum viable process' (MVP), providing templates but allowing escape hatches for creativity, and adjust the time horizon of planning documents (charter, goals, roadmap) based on maturity.
Retool achieves this by hiring PMs with customer-facing backgrounds, having highly technical PMs who understand the product deeply, using Slack for direct customer interaction, and building/using their own product for internal tooling.
Managers should avoid building teams in their own image and instead focus on creating a 'product talent portfolio' that balances diverse skillsets, such as homegrown PMs who deeply understand the product with PMs from other companies who bring traditional rigor.
23 Actionable Insights
1. Implement Minimum Viable Process
Introduce processes (like templates) only when necessary to reduce variance, but always provide “escape hatches” for high performers to deviate if it doesn’t serve their purpose, acknowledging the cost of creativity.
2. Empower High-Performing Innovators
Managers should identify top talent who don’t need rigid processes and provide them with “air cover” and special treatment, being willing to “break the org” for their potentially transformative contributions.
3. Give Teams Permission to Think Big
Actively create cultural moments and processes that encourage bigger thinking, such as a “Think Bigger” section in planning documents or an annual “Crazy Ideas” document, to counteract the daily grind of a startup.
4. Mitigate Fear of Failure
Leaders must accept that big swings will sometimes stumble. Normalize failure by using “retrospectives” instead of “postmortems” and encourage public sharing of learnings to foster a culture of continuous improvement.
5. Adopt 70/20/10 Investment Split
Allocate 70% of building time to the core product (including maintenance/bugs), 20% to strategic initiatives, and 10% to ambitious bets, treating product management as a portfolio of investments.
6. Build the Scooter, Not Axle
When developing a Minimum Viable Product, focus on creating a simple, functional, end-to-end slice that delivers complete value to the customer, rather than just components of a larger, future product.
7. Build for Your Best User
In early product development, prioritize building for the ideal user who will immediately understand and benefit from the product, rather than over-optimizing for potential abuse cases or less-suited users.
8. Cultivate a Strong Writing Culture
Encourage long-form writing for all major communications (business reviews, strategy memos, product reviews) as it forces clear thinking and is a strong indicator of success within the organization.
9. Practice Rigorous, First-Principles Thinking
Instill a culture of questioning “why” and challenging assumptions, rather than accepting “best practices.” This can be driven top-down by founders and reinforced through a strong writing culture and questioning the status quo.
10. Cultivate Balanced Product Talent Portfolio
As a manager, avoid building a team in your own image. Instead, actively balance complementary skillsets (e.g., homegrown vs. external PMs, execution vs. visionary) and hire specifically to address team weaknesses.
11. Increase ‘At-Bats’ for Innovation
To encourage bigger swings, limit resources for new initiatives (small teams) and seek customer feedback as quickly as possible, reducing the risk and impact of potential failures.
12. Foster Customer Proximity in PMs
Implement strategies like hiring PMs from customer-facing roles, ensuring technical PMs for technical products, leveraging Slack for direct customer feedback, and using your own product internally to be your own customer.
13. Differentiate Trapdoor from Two-Way
Speed up decision-making by rigorously identifying truly irreversible “trapdoor” decisions (e.g., titles) and moving quickly on “two-way” decisions that can be easily reversed or adjusted (e.g., pricing for future users).
14. Launch Products with Startup Mentality
Start new product initiatives with minimal resources (1-2 people), treat them like internal startups requiring ROI proof for further funding, and initially keep teams separate from the core org to foster independent, rapid development.
15. Establish Core Process Documents
Ensure the company, functions, and individual teams have clear Charters (mission, vision, strategy), Goals (aims, success metrics), and Roadmaps (what’s shipping), working from top-down (Charter first).
16. Adjust Process Time Horizons
Recognize that the time horizon for planning documents shifts with company maturity; an early-stage startup’s charter might be 3 months, while a mature company’s could be a decade.
17. Consider Sales for Aspiring PMs
For those looking to enter product management, a sales role can be highly valuable for gaining direct customer interaction, understanding pain points, and figuring out how products solve business needs.
18. Understand Full PM/Manager Scope
Before pursuing product management or management, be “really, really sure” about what you’re signing up for, including the less glamorous but essential tasks like performance reviews, one-on-ones, and cross-functional influence.
19. Communicate Roadmaps Effectively
When sharing product roadmaps with sales, success, and support teams, experiment with formats like a “science fair” where product teams staff booths to provide demos and answer questions at varying depths.
20. Publicly Share Learnings from Failures
When a project fails, use it as an opportunity to learn by having teams write notes to the entire organization or present at all-hands meetings, detailing their learnings and fostering a positive twist on the experience.
21. Fund ‘Think Bigger’ Initiatives
To encourage longer-term thinking, leaders should be willing to fund small teams or individuals to explore new ideas, use hackathons, and ask “what would you do if you doubled the team?” in planning processes.
22. Allow Flexibility in ‘Think Bigger’
When asking teams for “Think Bigger” ideas, provide minimal structure (e.g., bullet points or full demos) to avoid pigeonholing or intimidating contributors, encouraging broader participation.
23. Manage Maintenance within Core Product
Integrate maintenance, tech debt, and bug fixing squarely within the 70% allocation for the core product, allowing teams to determine their specific approach (e.g., Friday bug bashes).
6 Key Quotes
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 meet a certain standard. And the cost of that is obviously while you're reducing the standard and bringing folks up to the average, you're also bringing other folks down to the average.
Eeke de Milliano
I don't think you can be a good writer unless you're a clear thinker. And if you couldn't write well, I think it was actually pretty hard to be successful at Stripe, at least in the early days.
Eeke de Milliano
I always wonder, like, what is it that stopping folks from being creative and thinking bigger? Like, I feel like no one wakes up in the morning and thinks like, yeah, today, I want to work on like boring, incremental stuff. But most teams do end up working on like pretty incremental stuff.
Eeke de Milliano
If you make this decision, is it like one door or is it, is it two doors? And like, can you come back from this decision?
Eeke de Milliano
Build for your best user, not your worst user.
Eeke de Milliano
Wouldn't that be an amazing problem to have?
Anthony (Retool founder, quoted by Eeke de Milliano)
1 Protocols
70-20-10 Product Investment Model
Eeke de Milliano- Allocate 70% of building time to the core product that has product-market fit, including maintenance and bug fixes.
- Allocate 20% of building time to strategic initiatives that are not core but are strategically important for the company.
- Allocate 10% of building time towards big bets or innovative explorations.