These are the prompts that show up most often when owners and senior leaders sit down with AI in their actual workflow. They lean heavier on judgment than the operations or sales libraries — these are the ones where AI helps you think, not just produce output.
Best practice: load a Claude Project (or equivalent) with your business context — your operating model, your numbers, your key customer profile, your recent strategic conversations — then run these prompts inside that context. The depth of the answers improves dramatically.
Everything below is yours to copy, edit, and improve.
Strategy and decisions
What it’s for: Sharpening a strategic decision before you commit — without handing the call to the model.
I'm weighing a strategic decision. Help me frame it cleanly.
The decision:
[paste decision statement in 1-2 sentences]
What I know:
[paste relevant context -- market, business state, financial picture, team]
Options I'm considering:
[paste options]
Output:
- A 1-paragraph reframe of the decision (sometimes the decision is the wrong frame)
- For each option: expected value if it works, downside if it doesn't, reversibility, time-to-know
- The 1-2 pieces of information that would materially change my view
- A read on which option I'm probably underweighting (and why)
Don't pick for me. Sharpen the frame.What it’s for: Surfacing how a decision could fail before you’ve made it, so you can build in early warnings.
We're about to commit to [decision]. Run a pre-mortem.
Context:
[paste decision details, expected outcomes, key assumptions]
Imagine it's 12 months from now and this decision has clearly failed. Walk backward:
- What's the most likely way it failed?
- What's the second most likely way it failed?
- What signal would we have seen in months 1-3 if we were paying attention?
- What's the early warning indicator we should track?
- What's one thing we could do *now* to mitigate the most likely failure mode?
Be specific. Don't give me generic risk categories.Board and investor communication
What it’s for: A tight first draft of a board memo that leads with the headline and answers the obvious questions up front.
Draft a board memo on [topic].
Context for the memo:
[paste relevant business context, what's happened, what's coming]
Memo requirements:
- 1.5 pages
- Direct, specific, no padding
- Lead with the headline
- 3-4 supporting points with data
- 1 specific ask of the board (decision, input, awareness)
- Anticipate the 2 most likely board questions and address them preemptively
Tone: confident but not promotional. Honest about what's uncertain.What it’s for: The narrative section of a quarterly investor update — candid, specific, no corporate speak.
Draft the narrative section for our quarterly investor update.
This quarter's data:
[paste financial results, key metrics, major events]
Last quarter's narrative for context:
[paste prior narrative if available]
Requirements:
- 400-500 words
- Lead with the quarter's most important news
- Address any miss directly (don't bury)
- Show clear-eyed view of next quarter
- End with the one thing investors should hold us accountable to
Tone: confident, candid, specific. Avoid corporate speak. Read it back to yourself -- would I write this if my best mentor were reading it?People and culture
What it’s for: An all-hands message that’s clear and human without burying the point.
Draft an all-hands message on [topic].
Context:
[paste what's happened, why we're communicating, what we want the team to understand]
Audience: [describe team size, mix of roles]
Requirements:
- 250-400 words
- Direct, clear, doesn't assume people read between the lines
- Acknowledges the human side (anxiety, uncertainty) without making the message about that
- Specific about what we're doing and why
- Specific about what we're asking of the team
- Specific about when they'll hear more
Tone: leader-to-team, not corporate-to-employees. Don't soften so much that the message gets lost.What it’s for: Prepping for a hard feedback conversation so it lands clearly and supportively.
I have a difficult feedback conversation coming up with [role/person]. Help me prep.
The situation:
[paste what's happened, what I've observed, what's at stake]
What I want to communicate:
[paste your intent]
Help me organize:
- The opening (specific, doesn't bury the lede)
- The 2-3 specific observations (with examples)
- The impact (on the business, the team, them)
- The ask (what I want them to do differently)
- The support (how I'll help)
- The follow-up (how we'll know in 30 days)
Tone: candid, direct, supportive. Avoid "feedback sandwich." Avoid hedging that obscures the message.Synthesis and thinking
What it’s for: Turning messy leadership-meeting notes into clear decisions, open questions, and unresolved tensions.
I just came out of a 90-minute leadership meeting. Synthesize the notes.
Notes:
[paste raw notes -- could be messy, fragmentary, multiple voices]
Output:
- 3-5 decisions made (specific, with owners and dates if mentioned)
- 3-5 open questions / things to follow up on
- 1 tension that wasn't resolved (sometimes the meeting glossed over the harder thing)
- 1 thing I should think about more on my own
If the notes don't support an item, say so -- don't fabricate.What it’s for: Reading a long document fast and knowing exactly what deserves your attention.
Read the following carefully and tell me what I should pay attention to:
[paste long document -- could be a report, a competitor's announcement, a customer letter, a board pre-read]
Output:
- The 3 things that matter most for our business
- 1 thing that's easy to miss but matters
- 1 thing that's emphasized but probably matters less than it appears
- 2 specific questions I should be asking that the document doesn't answer
- A 1-paragraph summary I could use to brief my team
Be specific. Cite passages.Personal effectiveness
What it’s for: Checking whether your calendar actually reflects your stated priorities for the week.
Here's my calendar and stated priorities for the week:
Calendar:
[paste meetings and time blocks]
Stated priorities (what I said matters most):
[paste 3-5 priorities]
Tell me:
- Where my calendar matches my priorities (and where it doesn't)
- The single biggest mismatch
- 1-2 specific changes I could make this week to align better
- Anything in my calendar that probably isn't worth my time
Don't lecture. Be specific to my situation.What it’s for: An honest quarterly self-reflection that helps you see yourself clearly instead of flattering you.
I'm doing a quarterly reflection. Help me organize my thinking.
What I committed to at start of quarter:
[paste prior quarter goals or intentions]
What actually happened:
[paste rough summary of the quarter]
Output:
- What I delivered vs. what I committed to (clear comparison)
- 1 thing I underestimated
- 1 thing I overestimated
- 1 pattern I'm seeing in myself I should pay attention to
- 1 thing to commit to differently next quarter
- 1 thing I'm proud of (don't skip this -- it matters)
Tone: honest, observational. Help me see myself clearly, not flatter me.A note on the deepest use
The most senior leaders we work with use AI in two distinct ways.
The first is mostly what’s in this library: clear-purpose prompts that produce clear-purpose outputs. Faster, sharper, more leveraged.
The second is harder to put in a library — a thinking partner. You have a conversation with the AI about a question you don’t yet have framed. You argue. You push back. You explore. The skill is in the conversation, not the prompt. We can’t write that into a template, but we can tell you it’s where the most senior people are getting the most leverage.
If you want help building that capability across your senior team, that’s a real thing we do. A short intro call is the right place to start.