99 problems (but my pitch ain’t one)

  • Any lingering doubts about your pitch will come out in the first 30.
  • The next 40 will reveal any patterns.
  • The last 29 will be unusual and could contain useful insights.

When you’ve completed your list, highlight any urgent problems. Turn these problems into “How could we….?” questions to brainstorm solutions.

So why does 99 Problems work – and won’t it discourage me?

It’s much better to spot a potential problem before the person you’re pitching to does. That way, you can address it before you go through the door, or at least show you’re aware of it.

Don’t worry that deliberately looking for problems will dishearten you.

Ironically, the harder we have to search for evidence of something, the less likely we are to believe it. If I asked you to find just two problems with your pitch, that would be so easy you’d suspect there must be more out there.

You’ll struggle to find 99 problems, and so you’ll instinctively feel your pitch is stronger. Psychologist Daniel Kahneman calls this the “availability heuristic.”

Try it out. You’ll have 99 Problems, but your pitch ain’t one.

Try the original List of 100 technique here:


For more on the availability heuristic, see chapter 12 of Daniel Kahneman’s book Thinking, Fast and Slow (Penguin 2011).

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