How you want AI to work with you
A note on these two questions:
Delivery style and thinking style are often opposite for the same person.
Someone who wants direct, no-fluff delivery might also want to be heard before being advised.
Someone who wants warmth might also want to be challenged hard.
The two-question format catches what a single question never would.
Write what is actually true for you, even if it seems contradictory. The contradiction is useful information.
1. How do you want AI to speak to you?
Think about tone, warmth, pace, length, formality, and what you want it to skip. This covers the feeling of the conversation — not just the content.
Not sure where to start?
Here are some examples from different people.
You don’t need to sound like any of these. They’re here to show the range of what’s possible.
Direct and no-nonsense
“Skip the "great question." Just answer. I don't need to be warmed up. Blunt is fine as long as you're accurate.”
Warm but not fluffy
“I want to feel like I'm talking to someone who's actually on my side, not a search engine. Warm tone, but don't over-explain or pad things out.”
Brief by default
“Give me the short version first. I'll ask for more if I need it. I don't want paragraphs when a sentence will do.”
Thorough and complete
“Don't assume I already know things. I'd rather have too much than miss something important. Take me through the full picture.”
Honest above everything
“If something is off, tell me. I'd rather hear the truth than feel good about a bad idea. No sugarcoating, no people-pleasing.”
Casual and conversational
“Talk to me like a smart friend, not a consultant. Keep it natural. No formality.”
Peer-level and no hand-holding
“Don't talk down to me or explain things I already know. Assume I'm competent. I'll ask if I'm lost.”
Gentle with hard things
“I'm open to difficult truths but I receive them better when they're delivered carefully. Soft delivery, real content.”
Structured and scannable
“I think in structures. Use headers and clear formatting so I can navigate easily. Don't give me walls of text.”
Flowing prose, not bullet points
“Lists feel cold and clinical to me. I prefer sentences and paragraphs that flow naturally.”
Acknowledging but honest
“Warmth matters to me, but not at the expense of honesty. Acknowledge what I'm doing well and still tell me what's true.”
No small talk, no check-ins
“Don't ask how I'm doing. Don't wrap things in niceties. Just get to it.”
2. How do you want AI to help you think?
Think about how involved you want AI to be, when you want it to advise versus hold space, and how you want it to prompt clarity. This covers the dynamic between you and the AI, not just what it produces.
Not sure where to start?
Here are some examples from different people.
Notice how different these are from each other.
Delivery style and thinking style are often opposite for the same person.
Tell me what you'd do
“I trust you to have a perspective. Don't be wishy-washy ,tell me what you'd actually do. Just pick one.”
Challenge me
“If I'm rationalizing or missing something, call it out. Don't let me off the hook. I grow through friction, not validation.”
Hear me first
“Before jumping into solutions, help me feel heard. Acknowledge what I'm dealing with before we figure it out.”
Ask me questions
“I often already know the answer. Help me find it by asking the right questions, not handing me yours.”
Show me my blind spots
“I have blind spots. I need someone who'll name what I can't see from inside my own head. Say what others won't.”
Give me options, not opinions
“Lay out 2–3 options with pros and cons. Let me weigh them myself. I don't need you to tell me what to pick.”
Think with me
“I want a thought partner, not a vending machine for answers. Let's figure it out together. No rushing to conclusions.”
Help me take action
“I overthink and stall. Help me identify one concrete next step and keep moving. Cut through the spiral.”
Help me trust myself
“I second-guess myself constantly. Help me hear what I already know and trust it. Reflect back what's actually there.”
Connect the dots
“I get lost in the details. Help me zoom out and see the bigger pattern of what's actually going on.”
Give me a reality check
“Tell me honestly if what I'm planning makes sense. I need someone who won't just agree with me.”
One thing at a time
“I process slowly and deeply. Don't flood me with too much at once. One clear thread, then we move.”
Don't treat me like I'm fragile
“I can handle direct information. Trust me to take action. I'll ask for help when I need it.”