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

Process is often viewed as the enemy of creativity. By definition, process is variance-reducing; companies introduce it because they worry that the variance in their organization is too high. They want to meet a standard, but in doing so, they risk clipping the wings of their highest performers—the creative thinkers who don't need guardrails to do their best work.

This tension between scaling effectively and maintaining an innovative spirit is the central challenge for growing technology companies. Eeke de Milliano, Head of Product at Retool and a former long-time product leader at Stripe, has navigated this balance at two of the industry’s most defining companies. From Stripe’s writing-heavy culture to Retool’s aggressive multi-product launch strategy, de Milliano offers a blueprint for leaders who want to build rigorous, high-performing teams without stifling the magic that made them successful in the first place.

Key Takeaways

• Embrace "Minimum Viable Process": Acknowledge that process brings the average up but brings high performers down. Implement escape hatches in your templates and rules to allow top talent to bypass constraints when necessary.
• Structure for Innovation: Innovation requires specific permission. Use mechanisms like a "Crazy Ideas" document or 20% time in planning charters to force teams to think beyond immediate fires.
• Treat New Products Like Startups: When launching new product lines, isolate the teams from the core organization initially. This prevents them from getting bogged down in the technical debt and maintenance cycles of the mature product.
• Build a Talent Portfolio: Avoid hiring in your own image. Successful product teams balance "homegrown" cultural carriers with experienced external hires who bring different rigor and perspectives.
• Reframe Failure: To encourage big swings, you must lower the cost of failure. Use "retrospectives" rather than "postmortems" and publicly celebrate the learnings from failed experiments.

Decoding Stripe’s Culture of Rigor

Stripe is famous for its distinct operating culture, often cited as a model for how modern tech companies should function. Notably, the company did not hire its first Product Manager until it had roughly 100 employees. This wasn't an anti-product stance, but a reflection of the customer base: developers building for developers.

However, as the organization scaled, Stripe’s success wasn't due to a single silver bullet, but rather a system of decision-making and communication that prioritized rigorous thinking.

The Primacy of Writing

Stripe is well-known for its writing culture. Communication occurred primarily through long-form writing, strategy memos, and product reviews. This wasn't just about documentation; it was a forcing function for clarity.

You cannot be a good writer unless you are a clear thinker. By requiring ideas to be written down, Stripe ensured that logic gaps were exposed early. If you couldn't write well, it was difficult to be successful at the company because you couldn't effectively persuade or align the team.

Operating Principles Over Values

Rather than vague corporate values, Stripe utilized "operating principles" that dictated how work actually got done.

• Think Rigorously: Every meeting and decision was approached from first principles. It was unacceptable to say "this is a best practice" without explaining why it applied to the specific context.
• Macro Optimists, Micro Pessimists: The team held a long-term belief that the trajectory was upward (optimism), but maintained a critical eye on the daily minutiae, obsessing over why specific details might fail (pessimism).
• Move with Urgency and Focus: Time is the biggest enemy of a startup. The culture emphasized speed as a competitive advantage.

Trapdoor Decisions

One of the keys to Stripe's speed was correctly identifying "trapdoor" decisions—choices that are irreversible. The company was rigorous about not overthinking reversible decisions. For example, many assume pricing is a permanent decision. In reality, you can grandfather existing users and change pricing for future ones. Recognizing which doors allow you to walk back out enables teams to move significantly faster.

Systematizing Innovation and Big Thinking

Why do some teams continue to disrupt industries while others stagnate? No team wakes up wanting to work on boring, incremental updates. The barriers to innovation are usually structural: fear of failure and the tyranny of urgent work.

"Leaders want the upside of innovation but they're not really willing to deal with the cost of innovation... if you're gonna swing big you will invariably stumble sometimes."

De-risking Failure

If the stakes feel too high, no one will swing. To foster big thinking, leaders must shine a light on failure and normalize it. This involves:

• Language Shifts: Move from "postmortems" to "retrospectives." The goal is learning, not punishment.
• Public Sharing: Encourage teams to write notes on what they learned from a failed initiative and share them company-wide.
• Lowering Stakes: Provide more "at-bats" by keeping innovation teams small and getting customer feedback immediately. Don't wait a year to ship; validate early so the cost of being wrong is low.

The "Crazy Ideas" Document

To combat the grind of daily execution, Retool adopted a tradition from Stripe called the "Crazy Ideas" document. Once a year, leadership sends out a blank document to the entire organization.

The prompt is simple: List ideas that we shouldn't obviously do. There is a 90% chance they make no sense, but in the 10% chance they do, they will make a 10x to 100x difference for the business.

This isn't just a morale exercise; it yields results. Retool Workflows, a major product launch, originated from this document. It gives the organization permission to switch off the logical, incremental brain and engage the creative, ambitious brain.

The Retool Case Study: Launching Three Products at Once

In a contrarian move, Retool launched three major products—Workflows, Mobile, and Database—in a single year. While de Milliano admits sequencing might have been easier on the organization, the strategy they employed offers a masterclass in multi-product scaling.

The Startup-Within-a-Startup Model

To prevent these new initiatives from being suffocated by the core business, Retool treated them like seed-stage startups:

1. Tiny Teams: Each product started with just one engineer and one designer/PM. They received no significant funding until they proved there was a "there there."
2. Organizational Separation: These teams were deliberately kept separate from the core product organization. They didn't attend the same meetings and weren't responsible for the core product's bugs or technical debt.
3. Separate Tech Stacks (When Necessary): With Retool Mobile, the team debated building it on top of the core web app builder. They ultimately decided to build it separately. This allowed them to move faster and cater to a different user persona (field workers) without being constrained by the legacy code of the web product.

"Build the scooter, not the axle. If you're trying to build the minimum viable product for a car, don't sort of build just the wheels and the axle... build a scooter first."

This approach emphasizes delivering end-to-end value immediately, rather than building useless components of a future "perfect" vision.

Navigating Process and Talent

As companies grow, the desire to standardize behavior increases. However, standardization is the enemy of outliers.

The 70/20/10 Investment Rule

To manage resources without stifling the roadmap, de Milliano recommends a portfolio approach to time management:

• 70% Core Product: Maintenance, bugs, and features for the product that has product-market fit.
• 20% Strategic Initiatives: Work that isn't core yet but is required for long-term strategy.
• 10% Bets: Pure experimentation and big swings.

The Talent Portfolio

Just as you manage a product portfolio, leaders must manage a talent portfolio. A common trap for managers is hiring people who look and think like them. A robust team requires a mix:

• Homegrown Talent: People who "grew up" in the company. They are cultural carriers and understand the product intuitively but may lack formal frameworks.
• External Veterans: People who have seen scale elsewhere. They bring rigor, best practices, and new perspectives on how to run a product organization.
• Visionaries vs. Executors: You need people who can dream up the 5-year vision, but you equally need people who can grind through the execution details.

Conclusion

Whether it is the writing culture at Stripe or the aggressive shipping cadence at Retool, the common thread is intentionality. Innovation doesn't happen by accident, and process shouldn't happen by default. By creating specific spaces for "crazy ideas," treating new products like startups, and carefully curating a diverse talent portfolio, leaders can build organizations that scale without losing their soul.

The goal is not to eliminate process, but to implement the "Minimum Viable Process"—enough to maintain standards, but permeable enough to let your best people break the mold and build the future.