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Most CEOs know something’s not working — but they can’t always articulate what they need, or who they need in the seat.
Enter Artificial Intelligence.
Lately, we’ve noticed more CEOs coming to us with excellent summaries of their business situation — often generated with AI. Honestly? We love it. A clear brief = faster, better match to the right interim leader.
The worst place to be as a CEO is knowing something is off… but not being able to name it.
AI helps you find the language.
A proven interim executive helps you fix the problem.
This guide (written with the assistance of AI!) gives you the exact ChatGPT prompts you need to help clarify:
- your situation
- your problems
- the outcomes you want
- whether you need an interim, fractional, or full-time leader
Why CEOs Should Use AI to Prepare for Executive Hiring
AI excels at helping you:
- organize messy thinking
- surface patterns
- turn intuition into structured language
AI does not understand:
- your proprietary context
- board and investor dynamics
- cultural and political landmines
- real-world tradeoffs
Think of AI as a clarity tool, not a strategy owner. That clarity protects you from:
- hiring the wrong role
- defaulting to a permanent hire too early
- confusing advice with execution
We are able to help you faster when you can say:
✅ “Our EBITDA trend looks like X.”
✅ “Critical risks include ABC.”
✅ “Success = accomplishing XYZ in 120 days.”
Instead of:
❌ “We need a CFO. Or maybe a COO.”
❌ “We need someone strategic but also hands-on, but also operational, but also finance.”
Use these prompts to diagnose what you really need — and define success before you hire.
A Quick Word of Caution Before You Use These Prompts
AI is powerful—but only when used with intention and boundaries.
The prompts below are designed to help you think more clearly, not to expose sensitive proprietary information or outsource judgment. Never paste confidential contracts, pricing models, customer data, or proprietary IP into any AI tool. We cover that and other important information in our companion article, Using AI Safely: A C-Suite Guide to Protecting Your Business While Driving Results.
AI Prompts to Clarify What You Actually Need
1. Diagnose the Business (Root Causes, Not Symptoms)
Prompt:
Act as a strategic advisor. Ask me questions to diagnose the state of my company across:
- financial performance
- operations
- leadership & culture
- technology & data
- customer pipeline & growth
- cash runway & capital needs
- risk & urgency
Continue until you have a clear, concise picture of my biggest risks and priorities.
Why this matters: Most failed executive hires don’t fail because the executive was weak. They fail because the problem was never clearly defined.
2. Decide Whether You Need Interim, Fractional, or Full-Time Leadership
Prompt:
Based on my answers, tell me whether I need:
- an interim executive
- a fractional executive
- a full-time hire
- advisory support only
Refine the responses with this prompt: Recommend the right experience level, scope, timeline, and outcomes. Do not default to a permanent hire — justify the recommendation.
Why this matters: This step protects you from overhiring too soon, underhiring during critical moments, and making résumé-driven decisions instead of focusing on outcome-driven leadership.
3. Define Success Before You Hire
Prompt:
Create a 90–180 day success plan for this role, including:
- 3–5 measurable priorities
- KPIs and timelines
- biggest risks + mitigation plan
- what strong leadership looks like at this stage
- first-week and first-30-day actions
If AI struggles here, that’s a signal—not a failure. It likely means priorities are still competing or the situation is evolving. That’s normal.
Why this matters: AI helps crystallize intent. It does not replace executive judgment.
Pressure-Test Executives Like an Operator
Prompts:
- Generate situational interview questions tailored to my company’s challenges.
- Focus on execution speed, crisis handling, accountability, and stakeholder alignment.
- Avoid generic leadership questions.
Why this matters: Precision beats volume. AI can generate hundreds of interview questions. That’s not the goal. The goal is to generate a list of questions that help you separate operators from talkers.
You’ve Used AI to Name the Problem. Now Solve It.
If you want opinions, call a consultant.
If you want résumés, call a recruiter.
If you want results, call us at 847.849.2800 or contact us to start the conversation about how one of our rock-star RED Team interim CEOs, COOs, CFOs, or another C-suite executive can make a difference at your organization.
AI helps you get clear; we bring leaders who create momentum.
Let’s get your company moving.
