7 Claude Prompts That Make You a Better CEO
The first five posts got work off your plate. This one is about the work only you can do: thinking, deciding and leading. Used well, Claude doesn’t make you think less. It makes you think harder.
One warning before you start. Like most AI, Claude can lean agreeable when you ask “what do you think?” Ask it directly to push back, and it will.
1. Run a pre-mortem
Find out how the plan dies before you bet the business on it.
I'm about to [decision, e.g., hire a second manager / sign a 5-year lease / launch a new service]. Here's the plan: [paste].
Imagine it's one year from now and this failed badly. Write the story of what went wrong, with the 7 most likely causes. Rank them by likelihood and damage, and give me an early warning sign and a prevention step for each.
2. Write the decision memo before you decide
If you can’t write it down clearly, you haven’t decided. You’ve just reacted.
Help me make this decision: [decision]. Ask me questions until you understand the options, the stakes and what I care about most. Then write a one-page decision memo: the decision in one sentence, each option with its pros, cons and costs, what I'd have to believe for each option to be right, your recommendation, and what would change your mind.
3. Red-team your own plan
Everyone around you has a reason to tell you it’s a great idea. Get one opinion that doesn’t.
Here's my plan for [goal]: [paste]. Be my toughest critic and don't soften it. Find the weakest assumptions, the risks I'm underrating and the places where I'm fooling myself. Then tell me the one change that would make this plan meaningfully stronger.
4. Run a weekly CEO review
Fifteen minutes every Friday beats a two-day retreat once a year. Run it in the same Project each week and paste last week’s priorities so Claude can hold you to them.
Here's my week: [paste your calendar, wins, misses and open loops, or just brain-dump it]. Last week's top 3 priorities were: [paste].
Run my weekly CEO review. Tell me what moved the business forward, what was busywork I should delegate or drop, which decisions I'm avoiding, and how I did on last week's priorities. End with the 3 things that matter most next week.
5. Sort everything on your plate
Most owners are busy. Fewer are busy with the right things.
Here's everything on my plate: [paste the full list]. Sort it into four groups: only I can do it, someone else could do it with a little training, it can be automated, and it shouldn't be done at all. Rank the first group by impact on revenue and the team, and suggest an owner for each item in the second.
6. Set your next 90 days
Three priorities you finish beat ten you start.
Here's where the business is today: [revenue, team, biggest problems, biggest opportunities]. Help me set 3 priorities for the next 90 days. For each, define what done looks like with a number, the owner, the first step this week, and what I'll stop doing to make room. Push back if I try to pick more than 3.
7. Write the update people actually read
Your team, partners and investors want the truth, fast.
Turn these notes into a monthly update for [my team / my partners / our investors]: [paste wins, numbers, challenges and asks]. Lead with the headline. Give the 3 to 5 numbers that matter, with last month for comparison. Be honest about what isn't working, and end with what I need from them. Keep it under 400 words.
That’s the series
AI won’t run your company for you. But an owner who uses it to think clearly, decide faster and see around corners will outrun one who doesn’t.
Missed the start? Go back to post one for the 5-part prompt formula, then pick one prompt from each post to try this month. Keep the ones that work.
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“Without counsel purposes are disappointed: but in the multitude of counsellors they are established.” (Proverbs 15:22, KJV)
