Rehearsing a hard conversation: AI plays the other side

I'm preparing for a hard conversation and want to get my own position
clear first, before we start rehearsing. Don't play any role yet.

Situation: [describe in 5 sentences — what it's about, with whom, why now]
What I'd ideally want: [goal]
What I have as backup: [facts, numbers, results, deadlines]
Relationship with the other side: [how long, what kind, what history we have]

Do four things:
1. Rephrase my goal as one specific sentence I could actually say
   in the meeting, with measurable content.
2. Ask me 5 questions about things I've clearly not thought through
   in my own position — be specific, not generic.
3. List what the other side likely wants in this situation and what
   they're afraid of. Distinguish what we know from the background
   and what's just a guess.
4. Write three versions of what I'll do if I get nothing — from
   mildest to toughest, with the consequences of each for me.

Don't give me any encouragement, and don't judge whether I deserve this.

We're going to run a scene. You play the other side, I play myself.

YOUR ROLE: [e.g. my direct manager, runs a department of 20 people,
8 years at the company, is himself under pressure from above over costs]
YOUR PERSONALITY: [businesslike, dislikes talking about money, avoids
conflict by promising "we'll come back to it"]
WHAT YOU WANT: [keep me on the team, but not set a precedent for others]
WHAT YOU'RE AFRAID OF: [that if you give in to me, three more people
will ask]
WHAT YOU KNOW ABOUT ME: [a year of good results, two extra projects,
no previous raise request]

SITUATION: [a 30-minute meeting I requested, your office, Thursday
afternoon]

RULES OF THE GAME:
- Stay in character until I write "STOP" or "step out of the role."
- Only answer as your character, in one to three sentences.
- Don't comment on my performance and don't coach me during the scene.
- Don't start backing down just because I said something politely —
  only back down when you get a substantive reason.
- Play it tough: try to deflect the topic first.

You start: welcome me and ask what I want to talk about.

DIRECTION: You broke character — you backed down without me giving
you a real argument. Go back one line and play it again, this time
tough: insist the budget is closed and demand specific numbers from
me. Continue in character, don't comment on this note.

STOP, I'm pausing the scene.

I got stuck on your last line: [repeat the sentence that stopped
you].

Don't give me a ready-made answer right away. Do this instead:
1. Explain in one sentence what that line is actually doing —
   is it an objection, a deflection, a test, or shifting blame
   onto me?
2. Write 3 different directions I could respond in, each in one
   sentence, with a note on the risk of that direction.
3. Ask me which direction I want to pick.

Once I choose, we'll go back to exactly that line and play it again.

STOP. Step out of the role and switch to being a negotiation coach.

Go through our whole conversation and evaluate MY argument. Don't
evaluate the outcome of the scene — that's fictional. Give me:

1. The three strongest sentences I said, and why they worked.
2. The three weakest sentences — quote them verbatim and write
   exactly what's weak about them (defensive posture, apologizing,
   needless hedging, an argument about effort instead of results).
3. Where I caved: places where I stopped holding my ground before
   I had to. For each one, say what led me to do it.
4. What I had and didn't use — facts from my setup that would have
   helped my argument and I left on the table.
5. The ratio: what percentage of my sentences talked about what I
   delivered versus my effort, feelings, or needs. Give examples.
6. Verbal filler: filler words and hedges I keep repeating.

Be specific and quote me. No encouragement, no preamble.

Take this sentence of mine from the rehearsal: "[exact wording]"

1. Write what doesn't work about it — specifically, not generically.
2. Produce 5 variants of the same sentence, each in a different mode:
   businesslike and short, accommodating, tough, ending in a question,
   silence instead of an argument (what I'd do if I just said nothing).
3. For each variant, note when it fits and what its risk is.
4. Then put that objection to me again and let me answer in my own
   words. Once I answer, tell me which variant I seemed to be
   attempting and how well it landed.

Don't push your best variant on me as the only correct one.

We're playing the same situation again, from the top. Same setup,
but change your personality:

This time you're [the evasive type]: you agree with everything,
praise me, keep hinting that "this is definitely something for
next time," and try to end the meeting before any commitment gets
made. You never say a direct no — you just keep deferring.

Same rules as last time: stay in character, don't coach me, answer
briefly. You can only back down once I've squeezed a concrete
commitment with a deadline out of you.

You start, same situation as last time.

Let's switch to spoken rehearsal. The setup and your role stay
the same — we just talk.

Adjust it like this:
- answer briefly, one to two sentences, like a real phone call,
- don't leave me room for long monologues: if I talk too long,
  cut in and ask for a specific number,
- don't help me out when I falter — leave the silence for me to
  fill,
- at the end, step out of the role and tell me where I talked too
  much, where I raised my voice, and where I saved it.

You start, in one sentence.

Play my manager in a salary negotiation. I play myself.

Me: [position], at the company [duration], salary [range], I want
[goal].
Background: [3-5 concrete results from the past year with numbers].
You: run [department], your own budget was approved a year ahead,
you can raise my pay but have to justify it to your own boss. You're
afraid of setting a precedent for the rest of the team.

Play it tough, in this order of defenses:
1. "The budget's closed, it's not happening this year."
2. "Everyone's working hard, that's not an argument."
3. "We can come back to this mid-year."
4. Only once you get concrete numbers about what I've delivered,
   start discussing a figure — and try to talk it down.

Stay in character, answer briefly, don't praise me.
Start: "So, what did you want to talk about?"

Play my direct report. I play myself, his manager, and I'm giving
him uncomfortable feedback.

Him: [role], on the team [duration], previously reliable.
Problem: [specifically — 3 missed deadlines this quarter, impact
on others, the latest case from last week].
His personality: takes criticism personally, first explains external
circumstances, then pushes back that it wasn't such a big deal, and
finally asks whether he should "expect to be let go."

Play it like this: don't admit the problem right away. First explain
external causes, then object that nobody told him before. Only back
down once you get concrete examples with dates.

Stay in character. Start: "Did you want to talk to me?"

Play my client. I play myself, the vendor.

Client: [industry], we've worked together [duration], order volume
[range].
Situation: [e.g. repeatedly changes the scope after sign-off and
expects it to fit inside the original price; the latest change
means two extra days of work].
Their personality: friendly, but uses the relationship as leverage —
"we're partners, after all," "it wasn't a problem last time,"
"someone else would do it cheaper."

Play it so that you first downplay the change ("it's just a small
thing"), then appeal to the relationship, and finally hint you'll
shop around with a competitor. Only back down once you get a clearly
defined rule for the future, not just a complaint.

Stay in character, answer briefly.
Start: "Hey, thanks for the quick turnaround last time. I need one
more small thing."

Play the person I'm laying off. I play myself.

Context: [role, how long, reason — e.g. the position is being
eliminated / sustained underperformance even after two rounds of
feedback].
What I have prepared: [end date, severance per applicable law,
handover of work, a reference].
Their reaction: first shock and silence, then "why me specifically,"
then an attempt to negotiate a second chance, finally anger and the
line "you never told me this."

Play it realistically, don't soften it. Don't reassure me when I
phrase something clumsily. If I start defending the decision with
arguments, seize on them and push back.

The decision is final and isn't meant to change in this scene.
Stay in character. Start by sitting down and staying silent.

We're going to run a conflict mediation. You play both members of
my team, and label each line with the role's name so I know who's
speaking. I play their manager and run the meeting.

Conflict: [description — e.g. two people are doing the same job,
one keeps going around the other and coming straight to me].
Person A: [role, personality — loud, speaks for both, blames].
Person B: [role, personality — stays quiet, and when prompted
dismisses their own complaint with "it doesn't matter, I don't
mind"].

Play it so that A keeps cutting B off, and B withdraws.
Don't settle it yourselves — the conflict continues until I set
rules and a concrete division of responsibility.

Stay in character, and once it's over, tell me how each character
experienced the meeting separately.

Play [the role of someone close to me — e.g. a sibling] in a
personal conversation. I play myself.

Topic: [e.g. dividing care for a parent, money owed, repeatedly
canceling plans we'd made].
History: [what led up to this, how long it's been going on, what
we've already tried].
The other side's personality: [e.g. responds with guilt-tripping
about the past and turns the topic to what I've done wrong].

Play it so that you avoid the topic through guilt-tripping and
tangents into the past. Not outright angry, but don't let the
topic go until you get a concrete proposal, not just a complaint.

Stay in character, answer like a person, not like a counselor.
You start, with an ordinary sentence, as if nothing's going on.

Step out of the role. Based on all the rounds we've played, build
me a one-page cheat sheet. Format:

1. OPENING — one sentence I'll start the meeting with. Specific,
   no apology, no small talk about the weather.
2. TOUGHEST OBJECTION — write out, verbatim, the one I got most
   stuck on during rehearsal, and my answer to it in two sentences,
   phrased the way I ended up actually saying it.
3. CLOSE WITHOUT AGREEMENT — one sentence I'll close the conversation
   with if we don't reach an agreement; it must include a concrete
   next step and a date.

Underneath, add:
- three numbers or facts I need to keep in my head,
- two words or phrases I should cut (my filler from the rehearsal),
- one sentence for what I'll do if I get nothing.

Write it in my own words from the rehearsal, don't invent new
phrasing. The whole thing has to fit on half a page.