The Three Innovation Blockers
Diagnose why a team plays it safe by checking the three specific things that quietly kill big thinking
- Difficulty
- Moderate
- Time to result
- ~months to results
- Steps
- 4
- Confidence
- 92%
Teams rarely choose to work on incremental, boring things on purpose — something is stopping them from thinking bigger. Eeke de Milliano isolates three root causes and a countermeasure for each: fear of failure (normalize and de-risk it), urgent-work overload (clear the debt), and no permission to think (build thinking into the process). Rather than asking why some teams innovate, she asks why most teams don't.
Origin
Eeke de Milliano, Head of Product at Retool and an early Stripe PM, developed this from observing innovative vs. plodding teams across both companies.
Core principles
- 01No one wakes up wanting to build boring incremental work — a blocker is always in the way
- 02Leaders want the upside of innovation but avoid paying its cost, which is occasional public failure
- 03Big thinking is genuinely hard and requires deliberately protected time, not willpower
- 04Lowering the stakes of a swing is what makes creative risk-taking possible
How to run it
- 1
Shine light on failure to remove the fear
Normalize failure by making it public and framed as learning. Rename postmortems to retrospectives, have people write and circulate their learnings to the whole org, and let them present at all-hands.
Pro tip Airbnb ran a short-lived award for the biggest failure/project — a trophy that celebrated the swing.
Watch out If an individual or team fails consistently without learning, that is a real problem to address — normalizing failure is not tolerating repeated non-learning.
- 2
Give people more at-bats to lower the stakes
Anything that takes a year to ship with no customer feedback makes failure feel devastating. Keep bet teams small (don't over-resource them) and get customer feedback as fast as possible instead of waiting for perfection.
Pro tip Small teams + fast feedback loops mean a wrong guess is cheap, so people swing more freely.
- 3
Clear urgent work so teams can climb the hierarchy of needs
Teams buried in tech debt, product debt, bugs, and instability have no headspace for creative work. Diagnose whether a team is stuck in firefighting and actively get them out of it before expecting innovation.
Watch out Enlightened, big creative work is impossible while a team is heads-down on incidents all day.
- 4
Give teams explicit permission to think
Create moments in your culture and processes that literally tell people 'thinking bigger is part of your job.' Add a 'think bigger' section to every team charter asking 'with 20% more time, what would you do that isn't on this list?' and run a company-wide Crazy Ideas doc.
Pro tip Ask 'if you doubled the team today, what would you do?' in planning docs — people plan toward the team they have, not the team they should have.
In the wild
At the start of each year, David sends a blank doc titled 'Crazy Ideas' to the whole org, with the prompt: ideas we shouldn't obviously do, ~90% chance they make no sense, but in the 10% chance they do they make a 10-100x difference. The org loves it and its energy is high; ideas span product, org operations, and marketing.
→ Reviewing the prior year's doc, Retool consistently ships three-to-several items from the list; at least one or two of the three products launched in the prior year originated as crazy ideas — including Retool Workflows.
Retool maintains a 'shipped' email list; when someone ships (including a failed effort) they send their learnings to the org, turning what is normally only a success channel into a place to celebrate and learn from failure.
→ Failure gets a positive public twist instead of being hidden, reinforcing the norm that swinging big is safe.
Common mistakes
Wanting innovation's upside without paying its cost
Leaders ask for big swings but punish or hide the inevitable stumbles, which teaches everyone to stop swinging.
Expecting creativity from a team drowning in urgent work
A team stuck on bugs, tech debt, and incidents has no headspace for big thinking, so exhortations to innovate fail until the urgent load is cleared.
Is it for you?
Best for
Product and engineering leaders whose teams keep shipping incremental work and who want a concrete diagnosis of why
Not ideal for
Very early startups still hunting for product-market fit where survival, not innovation cadence, is the constraint
From the transcript
“one is this fear of failure like I think leaders want the upside of innovation but they're not really willing to deal with the cost…”
“you have to start Shining Light on failure that's that's really the only way like you have to start normalizing it a little bit”
“instead of calling something a postmortem called a retrospective so that it's kind of a positive thing”
“you have to figure out how to give folks more at bats”
“there's just too much Tech debt there's too much product debt bugs instability it's like massive hierarchy of needs”
“give teams permission to think so create these moments in your company culture”
“crazy ideas are ideas that we shouldn't obviously do there's a 90 chance that they make no sense but in the 10 chance that they…”
From the episode
How to foster innovation and big thinking
Eeke de Milliano (Retool, Stripe)