Problems One and Two
Stop reporting your productivity on problems 3-100; get stuck on the two hardest ones
- Difficulty
- Easy
- Time to result
- ~ongoing to results
- Steps
- 3
- Confidence
- 90%
A discipline for senior operators who are highly productive and therefore highly capable of avoiding the hardest problem. The rule: identify the two hardest problems in your domain, and make them the only things you bring to your leadership one-on-ones — even if the team is legitimately working on ninety-eight other things. Being 'stuck' on problems one and two is the job; a long checklist of solved problems three through one hundred is often a sophisticated form of avoidance.
Origin
Direct feedback from John Collison, Stripe co-founder, to Jeff Weinstein about nine months into reporting to him. Weinstein would arrive at his one-on-one with a clipboard of accomplishments, blockers and escalations, flipping paper somewhat frantically. Collison told him he was one of the best people he'd ever worked with at solving problems three through 100 — but he needed him stuck on problems one and two. Weinstein calls it a gut punch and deeply impactful advice.
Core principles
- 01High productivity on the non-hardest problems is a real, and comfortable, form of avoidance — usually not deliberate.
- 02Nobody wants to be stuck on something extremely hard when there is so much else that can be visibly progressed.
- 03Reporting a long list of accomplishments to your leader signals breadth but consumes the scarce time you should be spending on the two things that matter.
- 04Your team can continue to work on problems 3-100; the change is what you personally get stuck on and what you escalate.
How to run it
- 1
Rank the problems honestly
Write out the problems in your domain in genuine order of difficulty and importance. Be honest about which two you have been circling rather than sitting inside.
Pro tip The clipboard test: if your one-on-one prep is a long, frantic checklist of things done and things blocked, you are probably reporting on 3-100.
- 2
Bring only problems one and two to your leader
Change the one-on-one agenda entirely. Show up with problems one and two only, and do not talk about three through one hundred — even though you and the team are still working on them.
Watch out This feels career-threatening: Weinstein's reaction to the feedback was 'oh shoot, I'm going to be fired.' The point is precisely that the visible-productivity signal is what you're giving up.
- 3
Get stuck, together, on purpose
Use the leadership time to be genuinely stuck on the hardest thing rather than to demonstrate progress. That shared stuckness — not a status update — is what senior time is for.
In the wild
Nine months into reporting to John Collison, Weinstein would run into their one-hour one-on-one somewhat manic, with physical checklists — everything accomplished, every problem, every place needing escalation, every place stuck — flipping pages over frantically. Collison told him: you are one of the best people I've ever worked with at solving problems three through 100, but I need you stuck on problem one and two.
→ From then on Weinstein brought only problems one and two, never mentioning three through 100 even while the team worked on them. He calls it phenomenal, deeply impactful advice.
Common mistakes
Mistaking throughput for impact
Clearing problems 3-100 feels productive, is visibly valuable, and is genuinely useful work — which is exactly why it's such an effective mask for not engaging with the two problems that actually determine the outcome.
Using leadership time as a status report
An hour with a founder or executive spent listing accomplishments is an hour not spent getting unstuck on the hardest thing. The accomplishments could be an email; the stuckness cannot.
Is it for you?
Best for
Highly productive senior operators and product leaders who always have a full clipboard and never quite get to the hardest problem in their domain
Not ideal for
New joiners or ICs whose leadership genuinely needs breadth-of-status visibility, and contexts where the two hardest problems aren't yet identifiable
From the transcript
“you are one of the best people I've ever worked with at solving problems three through 100 but I need you stuck on problem S…”
“from then on I would show up to him with problems one and two and not talk about provs 3 through 100 even if we…”
From the episode
Building product at Stripe: craft, metrics, and customer obsession
Jeff Weinstein (Product lead)