Hire a free Chief Staff using AI to get more time, focus and success
- Jennifer Willey
- Jul 31
- 7 min read
It's time to unlock the Chief Strategy Officer living inside your computer and phone
Jennifer Willey | Jul 31, 2026
I spent an hour this week training and coaching a group of former professional athletes — women who retired from playing soccer, who went on to build soccer academies, the first yoga studio in East LA, and coaching businesses of every stripe — on how they could and should be using AI.
These disciplined women ran conditioning drills at dawn and know what it feels like to push through when every part of you wants to quit. They studied strategy on the field, but aren’t using AI as a strategic partner in their businesses.
They are all using it today to help with a variety of tasks. But that’s like hiring a world-class strategic consulting agency to help you write emails or build Powerpoints. What a missed opportunity!
That’s not a knock on them. It’s just proof that even people with elite discipline haven’t been shown what this tool can actually do. Discipline gives you work ethic, but doesn’t teach you how to use a chief of staff you’ve never had before. So let’s fix that, with real prompts you can copy right now.
Step 1: Let it interview you first
Most people open a GenAI chat and immediately ask for an answer. Flip that. Before you ask AI to solve anything, have it interview you, the way a good consultant would before ever pitching a strategy.
Try this, typed or said out loud in voice mode:
“You are my strategic growth advisor and coach, tasked with helping me be more successful and fulfilled at work and in life. Before you tell me anything, I want you to interview me. Ask me one question at a time about my business, my biggest challenges, my goals for the next year, and how much time I realistically have each week to work on this. Wait for my answer before asking the next question. Once you have a clear picture, summarize what you’ve learned back to me.”
This single prompt does something most people never get from AI: it forces the tool to actually understand your situation instead of guessing at it. And answering the questions out loud, one at a time, tends to surface things you didn’t know you thought. One woman on the call said this was the first time she’d ever been asked, point blank, what’s actually keeping her up at night about her business — by a chatbot, of all things.
Step 2: Build your chief of staff, on purpose
Once it knows you, give it the job:
“Based on everything you now know about my business, I want you to act as my chief of staff. Tell me specifically what you would do for me on a daily basis, a weekly basis, and a monthly basis to help me be more successful. Be concrete — not general advice, actual tasks.”
Participants got back things like their Chief of Staff can:
Give you a five-minute CEO briefing with:
The three outcomes that matter most today
Meetings requiring preparation
Decisions only you can make
People awaiting a response
Revenue opportunities at risk of going cold
One task to delegate
One task to postpone or eliminate
A content plan that turns one idea into a week of posts across every platform they use. Not “be more consistent on social media.” Actual assignments.
Protected time for critical projects or activities that will never show up in your calendar otherwise
Most importantly, it can distinguish what is genuinely important from what merely feels urgent.
Protect a daily revenue-generating action
Before administrative work or other efforts, it would remind you to complete one action connected to revenue:
Follow up with a past client or prospect
Ask for an introduction
Advance an active proposal
Request a testimonial, case study or referral
Prepare you for important conversations
Before any conversation, AI would provide:
The person’s background and your relationship history
Their likely needs, pressures and decision criteria
The outcome you want from the conversation
Five strong questions
Potential objections
The specific next step you should secure
Any promise you should avoid making in the moment
And it would turn voice notes or transcripts into decisions, follow-ups, CRM updates and next actions afterwards.
Capture your ideas without letting them hijack your day
Push it further by naming the exact seat you need filled. If your money feels chaotic, say “you are my CFO.” If marketing is the fire you can’t put out, say “you are my chief marketing officer, and I need you to think three steps ahead of me, not just execute what I ask for.” You can have as many of these “employees” as you need, and none of them will ask for a raise.
Step 3: When you’re overwhelmed with what it gives you, redirect it instead to make it easy to implement
Every business owner in our session felt the challenge of trying to navigate through the forty brilliant ideas they would get from AI after every prompt. We all laughed about the simultaneous feeling of being both thrilled and paralyzed. So what do we do? Plan to come back to it ‘when we have time.’ Then, we close the tab and never return.
The fix isn’t to ask smaller questions. It’s this:
“This is great, but it’s too much. Create a 90-day plan using only the recommendations that will have the biggest impact, knowing I have [X minutes] a day to actually work on this. Break it into one clear action per day.”
If even that feels like too much, go one layer deeper:
“Take just the first step of this plan and break it down into the smallest possible actions. What’s the very first thing I should do, today, that takes less than 15 minutes?”
You can also ask it to be honest about what shouldn’t be on your plate at all:
“Given my 90-day plan, which of these tasks would be better handed to a contractor, a freelancer, or a coach than done by me?”
If cost is the barrier, remember that certified women-owned businesses can access free coaching through SCORE — real experienced humans, not just AI, at no charge.
Step 4: Use a ‘diagnosis prompt’ on your actual problem
Whatever is genuinely stuck for you right now — retention, pricing, a conflict you’re avoiding — don’t ask AI to solve it yet. First, ask it to diagnose the problem:
“I’m struggling with [your specific problem]. Before you give me any solutions, ask me a series of questions to get to the real root of what’s going on. Don’t stop until you understand not just what’s happening, but why it’s happening and what I’ve already tried.”
Then, once you’ve actually answered honestly:
“Now give me five different strategies to solve this, based on the strongest research and best practices available. For each one, tell me the tradeoffs.”
Pick the one that actually fits how you want to run your business — you’re allowed to reject the ones that don’t feel like you — and go one level deeper:
“I like the [X] strategy. Give me ten specific, tactical ways to put it into practice this month.”
Step 5: Rehearse the conversation you’re dreading, out loud
Put your AI in voice mode and role-play the hard conversation before you have it for real — the client canceling because “it’s too expensive,” the price increase you’ve been sitting on for six months because your stomach drops just thinking about saying the number out loud.
“Let’s role-play this. You be the client, I’ll be me. I want honest, direct feedback afterward and suggestions on how to better respond— don’t sugarcoat how I did.”
I did this live on the call, playing a coach whose client just quit. My first attempt got feedback that I was coming across as judgmental and pressuring. My second attempt signaled that my original price was never justified. Two tries, two humbling notes, from a chatbot with zero interest in sparing my feelings.
The research backs up why this matters especially for women: we hold the line on pricing and push back in conflict less often than men do, largely because we’ve learned—correctly and unfortunately—that we pay a different social cost for it. It’s something I cover in my upcoming book, Fearless in 5: Confidence, Communication, Connection, Control and Courage, if you want to learn more.
Rehearsing the hard sentence in your car before you ever have to say it to a real person’s face is one of the most useful, low-stakes things you can do with 10 free minutes.
Pick one thing
Don’t try all five steps this week. Pick one. Have it interview you. Or build your chief of staff. Or rehearse the one conversation you’ve been avoiding since spring. And give yourself grace.
The most capable people I coach — disciplined, high-achieving, quietly exhausted — are not the ones with a perfectly built system. They’re the ones honest enough to admit they’re stretched thin, and willing to let a tool that never gets tired carry some of the weight. Athlete or not, that’s a skill worth building.
Share What Works!
Tell us in the comments below what is the most valuable AI prompt you use for strategy development. Let’s all help each other be stronger and faster together—so we can fear less and grow more.
That’s the flip. Fear less, delegate more. Accept the help that’s available.
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Note: In writing this article, I used AI to help me distill down the key lessons and advice resulting from a 75-minute workshop and coaching session I led for professional athletes-turned-entrepreneurs. Using that rough draft, I added my storytelling, additional insights and editing to bring this to you.
