Is it too late to say Happy New Year? I think so long as it’s done before January 15, you’re safe, eh?
I’m still planning out my content approach for the rest of the year and will have more to report on this before the end of the month.
In the meantime, I’m sharing a new prompt I’ve been putting to use lately because of it’s ability to help me see angles and scenarios I may not have seen on my own. It might be just one prompt, but it always delivers for me.
The method I’m using isn’t new: a pre-mortem. This classic analysis is simple but the frame of mind it puts you and your team in typically surfaces ways in which your project could go off the rails, in ways you may not have taken the time to game out if you just focused on planning out the project’s milestones and deliverables.
However, sometimes you don’t have time to get everyone into a room for an afternoon to conduct this exercise. This is where AI can help you.
I like using ChatGPT 4-o1 for this, due to its advanced reasoning capabilities.
Paid subscribers will find the prompt sequence below.
Give it a try and let me know how this one simply prompt performed for you and how you adapted it.
Priming Prompt
I would like you to think like a pre-mortem specialist.
Think about all the ways something might go wrong, so you can effectively plan to stop it from happening.
My hope is that by running this thought exercise at the beginning of our project, you can highlight things that might slow us down or stop us later on. What's the worst that could happen? Now's the time to figure that out.
I will first brief you on the current plan for our project. Then, I would like you to leap forward in time and you've found the project has failed spectacularly. Your job is to write every reason you can think of for the failure.
Are you ready to begin?ChatGPT should then confirm that it’s ready to begin.
You’ll then need to provide a detailed brief to ChatGPT before you can advance to this next script. The more detail, the better.
From there, engage in a thought exercise. Ask ChatGPT to provide more detail on each scenario.
Other ways I might adapt this prompt:
Ask ChatGPT to play specific roles on your team or project to think through different angles.
Use the Five Why’s to surface the specific aspects of each scenario that could go sideways.
Ask it for its thoughts on appropriate contingency plans for each scenario.


