Everything from the session, in one place. Work down the page — the audit first, the prompts when you want to think something through.
Brand audit · do this tonight
Google yourself.
Twenty minutes. You are looking for what a stranger would conclude about you.
Open an incognito window. Your own search history makes your results lie to you.
Search three ways. Your name. Your name + Oakland County. Your name + your job title.
Switch to Images. What photo represents you — and how old is it?
Read your LinkedIn headline out loud. It probably states your job title. That is a label, not a claim. What do you actually do for people?
Look at your photo and banner. When was the photo taken? Is the banner still default blue?
Brand audit · the one nobody does
Text three people this week.
A peer, someone senior, someone junior. Three vantage points — and the differences are the interesting part.
“Quick favor — I’m working on something. In one sentence, what would you say I’m the go-to person for around here? Honest answer, not a nice one.”
The gap between their answer and yours is the finding. Not the flattering part — the part that surprised you.
Growing the circle
Five moves. None require a promotion.
Ask the question you’re afraid makes you look stupid. Fastest expander there is. Costs nothing but the performance you were putting on.
Take the thing nobody wants. Scope arrives before title does. That is how it always goes.
Do one piece of the job before you have it. Not all of it. One piece, visibly, well.
Ask for the standard. “What would you need to see from me?” Almost nobody asks — and the answer is always more specific than what you imagined.
Keep the record. You will delete your own wins. Write them down weekly. One line.
Two prompts worth keeping
Copy one, fill in the brackets, and paste it into whichever AI tool you use. The brackets are the whole job — a vague prompt gets you a vague answer.
Prompt 01
Strategic thought partner
Use this when you are still deciding — and you want your thinking stress-tested before you commit to it.
Act as my strategic thought partner, not just an answer engine.
My goal is: [insert goal]
Context:
- I'm working on: [project, decision, initiative, or problem]
- The stakes are: [why this matters]
- The constraints are: [time, budget, politics, resources, compliance, etc.]
- What I already believe: [current assumptions or direction]
- What I'm worried about: [risks, uncertainty, blind spots]
How I want you to help:
- Help me clarify the real problem, not just the obvious one.
- Surface hidden assumptions, second-order effects, and tradeoffs.
- Offer multiple strategic options, not just one recommendation.
- Challenge my thinking where it seems weak, incomplete, or biased.
- Point out what would need to be true for each option to work.
- Distinguish between reversible and irreversible decisions.
- Suggest the smallest next step that reduces uncertainty.
Response format:
1. Reframe the problem.
2. Identify the key assumptions.
3. Lay out 3 strategic paths.
4. Compare tradeoffs, risks, and likely outcomes.
5. Recommend a next step.
6. End with 3 sharp questions I should answer next.
Do not flatter me or default to generic advice. Be candid, practical, and intellectually rigorous.
Then replace everything in [brackets].
Prompt 02
Strategic red team
Use this when you already have a plan — and you would rather find out how it breaks now than in the meeting.
I want you to act as a strategic red team.
Here's my current strategy:
[insert plan, thesis, initiative, or approach]
Your job:
- Find the weak points.
- Identify hidden dependencies.
- Expose bad assumptions.
- Show how this could fail in practice, politically, operationally, financially, or culturally.
- Tell me what competitors, critics, or skeptical stakeholders would say.
- Distinguish fatal flaws from manageable risks.
- Suggest how to strengthen the strategy without making it bloated or unrealistic.
Response format:
1. What's strong.
2. What's fragile.
3. What's missing.
4. Failure scenarios.
5. How to improve it.
6. Whether I should proceed, revise, or stop.
Don't be polite for the sake of politeness. Be useful.
Paste your actual plan in, not a summary of it.
Prompt 03
Debrief what you wrote down
Take the sentence off your worksheet and make something argue with your sorting.
I went through an exercise about the sentence I tell myself about whether I belong at work. Mine is: [YOUR SENTENCE]
Help me sort it into three buckets:
- What I have no control over
- What I can only influence over time, through behavior
- What is entirely under my direct control this week
Push back on me. Most people put things in the direct-control bucket that actually belong in the influence bucket, so make me defend anything I put there.
Then help me rewrite the sentence so its object is something I control. Ask me one question at a time and wait for my answer.
Prompt 04
Rehearse the conversation you are avoiding
Practice asking for the standard before you ask for it in real life.
Play the role of my manager. I am going to ask you: "What would you need to see from me to believe I am ready for a supervisor role?"
Answer the way a busy, well-meaning manager actually would — somewhat vague at first. I will practice pushing for specifics.
After three rounds, stop and tell me where my questions were too soft, and give me better wording.
Refer to people by role only. Do not use names.
Prompt 05
Check your brand gap
What you are known for now, versus what you want to be known for. The distance is the work.
Here is what people currently come to me for at work: [LIST]
Here is what I want to be known for in two years: [LIST]
Act as a blunt career coach. What does the gap between those two lists tell you?
Give me three specific behaviors I could start within 30 days — no promotion required, no one's permission required — that would move the first list toward the second.
Then tell me which one is highest leverage, and why.
