Learning from Failure: Stories from Product's Biggest Missteps

Compilation

Katie Dill, Paul Adams, Tom Conrad, Sri Batchu

MULTI-PART

Trust First

Katie Dill's Leadership Lesson: Trust Over Force

"I hadn't earned their trust. So whether how right or how wrong what I was doing was is the key piece, I wasn't bringing the team along with me."

Came in "swinging" with ambitious plans to change the design org at Airbnb
Got called into a meeting where half the team read prepared feedback on her failures
The real issue: she was executing change without building trust first
Shifted approach: listen, understand what people care about, bring them along

Notable Disasters

Product Failure Patterns from Pets.com & Quibi

Pets.com: Great product execution, broken business math, couldn't acquire customers profitably at scale
Quibi: Made a bet that bespoke short-form content could drive subscription retention at scale, the equation was wrong, not the execution
Google+: Born from competitive fear, not from solving real user needs
Google Buzz: Privacy disaster that showed what happens when fear-driven products ship at scale

Tom Conrad on Quibi's Math"If the equation is fundamentally broken or a big swing in and of itself, no amount of iteration and execution can get you out of the failed outputs of the broken equation."

Paul Adams on Google's CultureMany failures came from a place of fear rather than solving user problems. Fear-driven product decisions lead to broken outcomes.

Build Culture

Ship Fast, Learn Faster, Embrace Failure

Design the culture you want: Intercom built a "ship to learn" philosophy that celebrates failure as long as you're learning
The craft-speed tension: High standards vs. fast iteration is a real trade-off; both matter
Big bets require big learning: If you make bold bets, you'll fail more often than not, design your culture to accept that
Fail conclusively: Design tests that can fail cleanly, not ambiguously

Paul Adams at Intercom

"We've high standards ourselves. We never want to be embarrassed by what we ship. So there's a real tension there between high standards and shipping fast."

The Steve Jobs analogy

Simple interfaces, infinite use cases, one quality bar, shipping fast doesn't mean low quality; it means focusing ruthlessly on what matters.

Experimentation

Fail Conclusively: Sri's Framework

Most experiments fail (~70% failure rate is normal)
Failure ≠ not learning. Failure = not knowing why it didn't work
Design tests to fail conclusively, not ambiguously
Maximize treatment effect: throw all possible tactics at the hypothesis, then optimize if it works
If it fails even with maximum effort, it's a real "no"

The ABM ExampleAccount-based marketing gets tried repeatedly without conclusive tests. Each new exec tries it halfway, it fails ambiguously, next exec tries again years later.

Contrarian

What Great Product Leaders Actually Believe About Failure

✗Good leaders minimize failureINSTEAD →✓ Good leaders design their team and culture to fail well. Make big bets, fail fast, learn hard.

✗Failure is the opposite of successINSTEAD →✓ Failure is part of the path to success. If you're not failing, you're not experimenting hard enough.

✗Perfect execution saves bad strategiesINSTEAD →✓ Even flawless execution can't save a broken business equation. Fix the strategy first.

✗Failing ambiguously teaches you somethingINSTEAD →✓ Ambiguous failure is a waste of time. Design experiments so they fail conclusively, then you own the answer.

Based on a compilation episode of Lenny's Podcast. All ideas on this page are from the episode.Watch on YouTube

GO DEEPER IN THE EPISODE

03:25 Katie Dill: The single meeting that changed how Katie leads forever 08:03 Paul Adams: Freezing onstage in front of thousands of people 18:38 Tom Conrad: Lessons from Pets.com and Quibi, two of the most famous product disasters of all time 33:19 Sri Batchu: When you fail, make sure you fail conclusively 39:00 Jiaona Zhang (JZ): One of the biggest product misses at Airbnb 44:32 Gina Gotthilf: Everyone has an “A side” and a “B side,” and we should all share our B sides more 57:57 Maggie Crowley: Her favorite interview question about failure, and lessons from a personal failure 1:00:33 Thanks for listening

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