Based on Lenny's Podcast data
Idea #1 — Pre-Mortems
Imagine It Already Failed
🐯 Tiger
Will actually kill us
🗒 Paper Tiger
Seems scary, isn't
🐘 Elephant
Nobody is saying it
"Imagine this project has miserably failed 6 months from now. Work backwards — what went wrong?"
- Post-mortems extract insight after failure. Pre-mortems extract it before.
- The magic: psychological safety to voice concerns that feel "too negative"
- Include every function. Alternate talking with 5-min silent writing in shared doc.
- At end: each person votes for the tiger someone else mentioned — not their own
- Result: shared vocabulary. Future meetings use "I have a tiger" with no hesitation
Idea #2 — LNO Framework
Not All Tasks Are Created Equal — Stop Treating Them Like They Are
L
Leverage
Put in 1X, get 10-100X back. Write the PRD for the key feature. Do the strategic review.
N
Neutral
Put in 1X, get ~1X back. Routine stakeholder updates. Standard team meetings.
O
Overhead
Put in 1X, get far less back. Expense reports. Admin. Process tasks nobody reads.
"I was a perfectionist doing L tasks and O tasks identically. That's why my to-do list was endless and I was stressed — I was optimizing overhead like it was strategy."
- Reserve your highest energy for L tasks. Let your inner perfectionist shine only there.
- The same activity (e.g. writing a bug report) can be L, N, or O depending on what's at stake
- The extra time for L tasks must come from N and O tasks — not from working longer hours
- Most ambitious PMs fail this — they treat everything like it deserves their best work
Ideas #3 & #4
Three Levels of Work — and Why Execution Problems Are Really Strategy Problems
3 Levels of Product Work
Health Work — Keep the product alive and stable. Fix bugs, pay technical debt, maintain reliability.
Growth Work — Move the core metrics. Activation, retention, monetization improvements.
Delight Work — Create new value. New features, new experiences, new reasons to love the product.
When teams don't agree on which level they're working at, tension looks like an execution problem — but it's a strategy problem.
Execution = Strategy in Disguise
"Most execution problems are actually strategy problems. The team isn't slow or dysfunctional — they're executing a fuzzy strategy at full speed."
- Symptom: "Why aren't we shipping faster?" — Real cause: two teams with different strategic assumptions
- Symptom: "We keep re-prioritizing" — Real cause: no clear conviction on what matters most
- Symptom: "Lots of conflict between teams" — Real cause: teams working at different levels without realizing it
- Fix: name the level, name the goal, get explicit alignment — before blaming execution
Idea #5 — Prioritization
The Common Pitfall: Confusing Effort for Impact
- PMs naturally talk about what they spent the most time building — not what matters most to customers
- John Collison (Stripe): "Talk about the product in terms customers understand — not in terms of the effort you put in"
- Feature effort ≠ customer value. The things easiest to build might deliver the most value.
- Prioritize by impact on the user's life, not by complexity of implementation
- Ask: what would make users love this product more? (Jack Dorsey's one question)
Jack's one question
In a Stripe acquisition meeting with all the metrics and strategy laid out — Jack Dorsey simply asked: "How does this make our users love Twitter more?" Nobody had an answer.
Contrarian
PM Wisdom Worth Unlearning
✗
A post-mortem prevents the next failure
INSTEAD →
✓ A pre-mortem prevents the failure. Post-mortems extract insight from wreckage. Pre-mortems avoid the wreckage in the first place.
✗
Work harder when overwhelmed
INSTEAD →
✓ Classify your work first. Overwhelm is almost always caused by doing O tasks with L task energy. Stop, sort, refocus on leverage.
✗
We have an execution problem
INSTEAD →
✓ Almost certainly a strategy problem. Get explicit on which level of work you're doing and what the goal actually is before optimizing execution.
✗
Highlight the hardest thing you built
INSTEAD →
✓ Highlight what most changes the customer's life. Effort and impact are independent. The best feature might have taken 2 days to ship.