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