ISSUE 21 · ME+MACHINE
Your AI has seen a lot of how you work, and not the tidy version of it either.
So ask it what it's noticed.
I like to do this with my meeting notes. Every now and then, I'll ask it to read through the last few meeting transcripts and tell me which question I keep skipping. You can give it anything, though:
Meeting notes or transcripts. Granola, Google Meets, or whatever you're using to take notes. Make sure your AI is reading the full transcript, not just recaps. It's probably the best look you'll get at how you come across with other people.
A project folder. You get to see what you planned at the start compared to how it really went, as well as all the decisions along the way.
Your last 30 to 90 days of chats with the AI. This one's potentially quite broad, since it picks up whatever you happened to be thinking about that month.
Anything you wrote just for yourself. A journal, notes in Notion or Google Docs, the long message you drafted and never sent. Nobody was reading over your shoulder, so it sounds different from everything else here.
Here's an example of what I might ask.
Here's [describe the material]. Use only what's in it.
First, tell me in one line what you can see here.
Then give me five observations about me that I probably wouldn't make about myself. For each one, quote the part that made you say it.
Skip anything you can't quote. If there isn't much to comment on, say so.Copy this into ChatGPT or Claude and fill in the brackets.
"Use only what's in it" stops it padding the answer out with everything else it thinks it knows about you. Asking what it can see is helpful, especially when it’s pulling from chat history, so you know what it's pulling from. And making it provide direct quotes is what keeps each answer tied to your material. If it can't point to a line, you're getting something that would be true of anybody.
If the answers are still vague, it doesn't have enough to work with. Add material or ask a more specific question: provide ten meeting transcripts instead of two, or ask "how I handle disagreement" rather than "how I communicate."
One caution. Models are agreeable by default, and they take your side 49% more often than another person would. You don't have to go fishing for a compliment to get one, which is why the flattering reads are the ones to push back on first.
More you can ask
You only have to paste the material once. After that you can keep swapping the question or get more specific.
About how you work
"What do I keep saying I'm going to do?" Everything you meant to get to is sitting in there in writing, which is harder to skim past than it is in your head.
"What question do I keep circling without asking outright?" This is the one I run on meeting notes.
"What do you think I'm avoiding?" The most pointed one, and the one most likely to be overconfident.
"What do I sound like when I'm stressed?" Needs a source with some range in it, so chats or a journal rather than meeting notes.
"Which of these projects do I sound most excited about?" Run it before you decide what to drop.
About how you come across
"What would you warn someone about before they worked with me?" Asking sideways like this gets you further than asking for feedback straight out.
"What do you remember about me?" More of an audit than a reflection, and the entries it gets wrong are usually the interesting part. This one needs memory turned on, and it ignores whatever you pasted.
Have it guess your personality type
Run yourself through DISC, Myers-Briggs, or the Big Five, except with your own material instead of a questionnaire.
Based only on [what's in here / what you know about me], where would you put me on [DISC / Myers-Briggs /
the Big Five]? Quote the parts that made you land there, and tell me which letters you're least sure about.Just for fun
"Roast me." Exactly what it sounds like. Save it for last, because it changes the tone of everything after it.
"Guess something about me I've never told you." It's guessing here, so treat the answer as entertainment.
"What am I underrating about myself?" You're fishing for a compliment and it knows it, and sometimes it lands on something you'd stopped noticing.
These don't need to lead anywhere. Sometimes you just want to know what it'll say.
THE 30-SECOND VERSION
Have AI tell you what it can see before it answers, especially when it's working from your chat history instead of something you pasted.
Pick one source and go back as far as it goes. A month of meeting notes beats "everything you know about me."
Ask for five observations you wouldn't make about yourself, and make it quote the material for each one.
Have it guess your personality type from the material rather than a quiz.
Models agree with you more than people do, so the flattering reads are the ones to push back on.