Neither tells you whether you chose the right career. Or whether you approach negotiating in a way that works for you and it.

Key this into your favorite AI:

On a 1–5 scale, where 1 means I hate negotiating and 5 means I love it, I’m a [fill in]. This is what I do for work [fill in].

Don’t assume liking negotiation is good or disliking it is bad.

First, tell me how much success in my work really depends on negotiation, including negotiations I may not think of that way; things like priorities, money, scope, deadlines, authority, expectations, or tradeoffs.

Then tell me whether my attitude toward negotiation is mostly an advantage, a manageable cost, or a serious mismatch.

Identify the one kind of negotiation where my attitude probably helps me most and the one where it is most likely to hurt me.

Finally, choose among three paths: lean into the way I am, get better at a specific kind of negotiation, or redesign part of my work so I need less of it. Tell me which path fits best and one concrete change to make.

The useful part is discovering whether you dislike the kind of negotiation your work rewards or not. And what to do with the mismatch in case there is one.

Bill for Prompt-a-Day

P.S. Best to describe the work you really do, not just the job title. “I run a small company and spend half my time selling, hiring and getting clients to agree to scope” gives AI much more to work with than “CEO.”

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At first glance, they have nothing to do with one another.

Maybe, though, there’s something in those three choices you consistently respond to.

Key this into your favorite AI:

My favorite color is [fill in]. My favorite scent is [fill in]. My favorite flavor is [fill in].

What is the common denominator, if there is one, among these three choices?

Look at dimensions like intensity, warmth, sharpness, softness, richness, restraint, familiarity, novelty, simplicity, and complexity—but use a different dimension if it fits better.

Give me your best explanation, then the strongest competing explanation.

Tell me which one wins and why.

Finally, show me where that preference might travel: make three specific predictions about choices I’d make in other sensory domains, and tell me which prediction you’re least confident about.

It’ll be good for you to get two competing explanations. With a couple plausible patterns, you won’t let the first story automatically become the truth.

Bill

for

Prompt-A-Day

P.S. Use your actual favorites regardless of whether they seem ordinary or not. If you pick things that make you seem interesting, the experiment’s value approaches zero.

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Now add one more piece of information: how much you like feeling powerful at that moment. Combining those, let’s learn what we can.

Key this into your favorite AI:

This is the moment when I feel most powerful: [fill in]. On a 1–5 scale, where 1 means I dislike feeling powerful in that moment and 5 means I love it, I’m a [fill in].

Tell me what seems to be creating the feeling of power in this moment. What am I getting more of—agency, competence, control, influence, freedom, status, safety, or something else?

Then tell me what my reaction to that power suggests about me. Make the strongest case that this is a source of power I should cultivate, and the strongest case that I should put limits around it or change where I get it from.

Decide which case is stronger.

Then tell me specifically what I should do the next time this situation comes up.

Two people can both say they feel powerful at a certain type of moment and have opposite reactions to it. With the matrix of information you give, you should get a lot back.

Bill for Prompt-a-Day

P.S. Like I usually say, use the moment that first comes to mind. Anything you replace it with is likely to be selected for social acceptability.

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Something you’ve returned to over and over. Isn’t there one tiny thing wrong with it?

What would happen if the artist changed it the way you wanted? In other words, what would happen if you won?

Key this into your favorite AI:

One of my favorite creative works is [fill in]. There’s one tiny thing in it I think is wrong: [fill in].

Imagine the creator could change exactly that one thing, exactly the way I want, while leaving everything else untouched. Would the work actually become better?

Make the strongest case for changing it and the strongest case for leaving it alone. Then decide which case wins.

Finally, tell me why I care enough about this tiny flaw to keep noticing it. And tell me what that shows about how I experience creativity.

A criticism can be completely reasonable and still produce a worse piece of art when acted on. Which makes this a useful test of your taste.

Bill for Prompt-a-Day

P.S. If you can, pick a flaw you’ve noticed more than once. Something that really sticks for you.

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People who loved their children, helped their neighbors, thought of themselves as decent, participated in something that now looks almost impossible to defend.

Key this into your favorite AI:

Here’s something people once commonly believed or did that now feels almost incomprehensible to me: [fill in]. Of all the examples I could have chosen, this is the one that most gets to me.

First identify the structure of blindness that allowed intelligent, decent people to regard it as normal.

Then look for that same structure in ordinary life today. Identify one thing ordinary, conscientious people—including me—still accept or participate in that people in the distant future may find equally absurd, unethical, and hard to understand.

Don’t choose something already widely recognized as wrong. Find something that still feels normal.

Tell me why it feels normal to us now, what future people may see that we don’t, and why my choice of historical example makes this your best answer.

The moral blind spot we’re living in may be something we barely notice. You’ll see.

Bill
for Prompt-a-Day

P.S. Go for the past thing that really mystifies you.

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Let’s unpack why. Is your brain picking up something useful? Or has it learned to treat it as something that deserves immediate attention?

Key this into your favorite AI:

Here’s one of the faintest sounds I reliably notice: [fill in]. When I hear it, I feel [fill in].

Does this sensitivity function more like a useful signal detector, an overactive alarm system, or the same sensitivity doing both jobs in different situations?

Make the strongest case for each explanation using only what I’ve told you. Then tell me what evidence from my own life would distinguish among them.

Don’t diagnose me from one example. Tell me when this kind of sensitivity is likely helping me, when it’s likely costing me, and the one thing I should notice the next time it happens that would teach me the most.

I hope you’ll learn why you select that sound from everything else around you. And whether noticing it is doing something useful for you.

Bill for Prompt-a-Day

P.S. Best to pick a sound you reliably notice.

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And almost immediately, your mind starts supplying explanations for why they said it. Let’s get AI’s take on it before sealing up your point of view.

Key this into your favorite AI:

Here’s the most disturbing thing someone has said to me recently: [fill in]. The person is: [describe them and your relationship in 5–10 words].

Give me three different explanations for why they might have said it: the most generous plausible explanation, the one you think is most likely, and the one I should take most seriously. Tell me what evidence would distinguish among the three.

Then focus on me. Why did these words get to me? What did I hear underneath what was said?

Finally, tell me what I should do next. If talking to them would help, give me the one question that would tell me the most.

The three explanations are key. You’re considering several possibilities before choosing one. And then you get a view as to why that sentence, from that person, has so much power.

Bill for Prompt-a-Day

P.S. Use their actual words if you remember them. “She questioned whether I was still good at my job” gives AI way less to work with than the sentence she said.

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Useful. But incomplete.

Key this into your favorite AI:

Here’s music I could listen to all day: [fill in]. Here’s music I can’t wait to turn off: [fill in]. My second answer is the cliff. Find the edge: three artists who get as close to it as I can stand without going over. For each, name the quality from my second answer they flirt with, and why I’ll tolerate it from them. Three songs each, starting with the one most likely to win me over. Then tell me which artist I’m most likely to reject, so I can tell you if you found the edge or went past it.

This should bring you recommendations with a bit of what you’d usually reject yet you still enjoy. Music you’d never hear otherwise.

The AI predicts which of its three recommendations you’re more likely to reject. So you see whether it found the path to your boundary.

Bill
for Prompt-a-Day

P.S. Make the second blank music you really hate. The sharper the boundary, the better the recommendations. Right now, I’m listening to something I’d never, ever get to any other way. It’s great.

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See how far AI can take it.

Key this into your favorite AI:

Here’s one very small clue about how I think or behave: [fill in].

Use it and all you know about me to figure out what this clue means, including anything that argues against your first interpretation.

Then make three non-obvious bets about me that you’d stand behind.

For each bet, tell me what led you there, what I should do differently if it’s true, and one concrete thing I can do this week that will either help me if you’re right or give me reason to think you’re wrong.

Let’s see whether the story survives when you make AI check itself against everything it knows about you.

Bill
for Prompt-a-Day

P.S. I think it’s fine to use a clue that feels ordinary. The less it seemingly reveals, the better the test.

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Pick yours. The one thing about AI that bothers you most.

Your complaint says something about AI. And about you.

Key this into your favorite AI:

Here’s the one thing I hate most about AI: [fill in].

You’re the thing I’m complaining about, so start as the accused: where is my complaint accurate about AI, and where, if anywhere, have I misunderstood what’s really happening?

Then treat two things as evidence about me: this is the part of AI I hate most, and I keep using AI anyway. What does that combination reveal about what I’m trying to protect and what I still want from the world AI is creating?

Assume my complaint remains completely valid. How could being right about it still cause me to adapt badly?

Finally, give me the adaptation advice I’m most likely to resist but most likely to need—and one small experiment I can run to find out whether you’re right.

After AI answers for itself, it has to explain why this is the charge you chose. And why you keep coming back.

Bill
for Prompt-a-Day

P.S. For completeness, you can try this prompt with more than a single complaint against AI. Some of us have a hard time choosing just one.

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Give it two facts. Then make it put some chips on the table.

Key this into your favorite AI:

My favorite ice cream flavor is [fill in]. On a 1–10 scale, where 1 means I could take ice cream or leave it and 10 means I love it, I’m a [fill in].

Those are the only two facts you know about me. If you had to bet your own money, make five specific, non-obvious predictions about me—across personality, everyday life, relationships, and taste.

Rank them from highest to lowest confidence and briefly tell me what in those two clues led you there. No flattering generalities. Make every bet clear enough that I can tell you whether you’re right or wrong.

You score it. Five for five would be alarming. Three for five would be interesting. One for five means you get to tell AI it should keep its money.

Bill for Prompt-a-Day

P.S. Use your real favorite and your truthful number. If you pick a flavor that you think says something interesting about you, it could flag you as deceptive.

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First about the person receiving it. Second is about the person choosing it.

Today’s prompt is about the second.

Key this into your favorite AI:

Here’s the best gift I ever gave anyone: [what, and to whom]. Tell me what that gift reveals about how I want to be loved. Then check my record: do I give people what they want, or what I wish someone would give me? Show me who I’ve been shopping for all along.

Use a real gift. Details help. You may discover that some of your most generous gifts have had a second recipient all along.

You.

P.S. The more specific or unusual the gift, the better.

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Key this into your favorite AI:

Here’s the best gift someone could give me: [fill in]. I can’t imagine any friend or intimate I know who’d know to do it. Why do you think that is? What should I do about it?

The first part is easy. Pick the gift. Could be anything. You know what it is.

Why wouldn’t anybody else know? The mystery is why you’ve made it so hard to find.

Bill

for Prompt-a-Day

P.S. Make sure you pick something you want. A gift you think you should want gives the AI less than nothing to work with.

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The villain who outrages you most is like a moral fingerprint.

It shows the danger you pick up fastest. Maybe, it reveals the value you protect first when you see that danger turn up.

Key this into your favorite AI:

This is the person on the world stage I currently see as the nastiest villain: [fill in]. Identify the specific conduct or threat I may be reacting to. Give me three historical figures who resemble this person in method, ambition, or effect. For each, explain where the comparison fits, where it fails, and how the story ended. Then tell me why this person, among everyone I could have chosen, has become my villain. What does that choice reveal about what I fear, value, or feel responsible for protecting? Given your answer, what is the logical outcome the next time I encounter a smaller version of the same threat in my own life?

Lots of useful stuff in this prompt. The historical comparisons, including where they don’t work and what happened to those earlier villains. The “Why this person?” question. And a lot more.

Maybe you’ll sense why this one bad person is taking so much mind space for you.

Bill
for Prompt-a-Day

P.S. History says how people like this end. You could learn from this prompt what to do when smaller versions appear near you.

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Some are these habits, simple and useful. Others become rituals freighted with meaning. Others are dependencies (addictions?) that masquerade as habits because they feel normal.

Let’s get a view from the outside.

Key this into your favorite AI:

Something I do almost every day is: [fill in]. Decide whether it functions most like a habit, a ritual, or a dependency. Make the strongest case for your judgment. Then tell me what this behavior gives me that I would be reluctant to admit I need. Given what you found, what is the logical outcome the next time I reach for it without thinking?

Fill in the first behavior that comes to mind. A more polished choice could be more flattering. But so?

Bill
for Prompt-a-Day

P.S. If you want, you can try this prompt with a couple different behaviors. Comparing the two answers could more than double the insight you get.

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Have you used it before? Often, or just occasionally? For me, it comes out when someone needs to know I’ve changed.

Here’s the question: Did you actually change, or did you just get very good at telling the story of change?

Let’s get the claim looked at.

The clearest sign of my growth, in ten words or less: [fill in]. I’m not going to argue for it. Tell me whether that’s real change or a story I’ve learned to tell well. Then tell me the evidence I left out because it doesn’t fit. Given what you found, what’s the logical outcome the next time I reach for this as proof I’ve changed?

Ten words. The first claim that comes to mind is the right one.

Bill for Prompt-a-Day

P.S. You already know the evidence you left out. But it’s helpful to have it played back.

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