Planning guides
Pre-mortems, pressure-testing, finding holes in your own thinking before they find you.
The questions to ask before starting anything that costs you time. Pressure-testing a plan you've already gotten attached to. The failure modes you're not currently looking at.
Quick answers to more planning questions — each with the tool that does the heavy lifting.
How to Find the Holes in Your Own Thinking Before Someone Else Does
Your thinking has holes. So does everyone's. Five steps for finding the ones in yours before they get pointed out by someone with bigger stakes than you'd like.
- Steelman the strongest objection you can imagine
- Ask three different people who'll think differently
- Look for what you're avoiding examining
- Identify what would change your mind
- Know when finding the holes has become self-sabotage
💀 Pre-Mortem does this for you.
How to Know if Your Business Idea Is Actually Going to Work
You can't know with certainty before you start. You can know whether the question itself is the right one, what assumptions you're making, and what would change your mind. Five steps for an honest read.
- Define what 'work' actually means — concretely
- Find the five ways smart people would say no
- Stress-test the assumptions you can't easily test in advance
- Identify the smallest experiment that could change your mind
- Know when 'is this going to work' is the wrong question
💀 Pre-Mortem does this for you.
How to Plan a Project So It Doesn't Fail in the Obvious Ways
Most failed projects fail in ways the team should have seen coming. Five steps for surfacing the failure modes you can already see — before they become the post-mortem.
- Imagine the project failed — write the failure narrative first
- Identify which failure modes are unique to this project, not generic
- Pressure-test assumptions you didn't know you were making
- Build mitigations for the top three, not all of them
- Know when the obvious failure modes aren't actually the dangerous ones
💀 Pre-Mortem does this for you.
How to Pressure-Test a Plan Before You Bet Money on It
Most plans look better than they are because the person who wrote them is also the person evaluating them. Five steps for finding the weak points before the money goes in.
- List every assumption — including the ones that feel like facts
- Sort assumptions by reversibility cost
- Find the cheapest experiment to test the most expensive assumption
- Identify the kill criteria upfront
- Know when pressure-testing has become procrastinating
💀 Pre-Mortem does this for you.
The Questions to Ask Before Starting Anything That Costs You Time
Time spent is the cost you can't get back. Five questions to ask before committing real time to anything — and the meta-question for when the questions themselves are the problem.
- What does success actually look like — concretely?
- What's the cheapest version of this I could test first?
- What am I implicitly betting on that's outside my control?
- What does failure look like — and at what cost?
- Know when these questions have become a way to never start
💀 Pre-Mortem does this for you.
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