The fastest way to lose a CEO’s attention is to talk about your product (yawn). And the fastest way to get their attention is to think like them. AI can help you do exactly that.
Let’s start with the elephant in the room, selling to the C-suite is hard.
It is not about your product; it is about proving you understand what drives their business. Too many reps still lead with features, but CEOs, CFOs, and COOs do not buy features, they buy outcomes, strategy, and impact. Harvard Business Review has said this for years, make it easier for buyers to make confident decisions. Harvard Business Review
That is why I train channel sales reps to use a different playbook when they are in front of the C-suite. With ChatGPT at your side, you sharpen preparation, reframe your message, and walk into executive meetings sounding like a trusted advisor, not another vendor. Here is how to make it work.
Think Like the Chief Executive Officer
Executives don’t care about technical specs, they care about growth, efficiency, and differentiation. That’s the 2025 tension CEOs are navigating… growth ambitions balanced against cost control and even risk. Lead with business outcomes and position yourself as a partner. But don’t take your eye off of disruption, that might be the secret sauce.
ChatGPT Tips:
- Ask ChatGPT to reframe your product features into three measurable business outcomes for a CEO in [insert industry here].
- Role-play with ChatGPT as the CEO. Ask it to critique your pitch and surface likely pushbacks.
Master the Four Languages of the C-Suite
Nearly every executive speaks a different language. CFOs speak ROI, COOs speak efficiency, CEOs speak growth, and boards speak risk. Recent CEO and leadership coverage reinforces how executive language shapes strategy and culture. Translate your message to match their world. And be mindful of how you communicate to them. You can be sure they will use their words with you purposely.
ChatGPT Tips:
- Have ChatGPT rewrite your pitch for a CEO, CFO, COO, and board chair in [insert industry].
- Ask ChatGPT to build a simple comparison grid that shows how each role evaluates your solution.
Can AI Help You with Your Presentation?
If you’ve been given the time to present, keep it clear and outcome-driven. The three-slide rule works, lead with the outcome, show the path, and be ready for questions. Even McKinsey case work has highlighted constraints like three slides to maximize decision time.
ChatGPT Tips:
- Upload your ten-slide deck to ChatGPT and ask it to condense it to three executive-ready slides with speaker notes.
- Ask ChatGPT to generate the hardest objections a CEO in [insert industry] might raise. Then practice your answers during a roll-play with ChatGPT.
Prepare for Meeting Dynamics with ChatGPT
You rarely get the opportunity to meet with just one executive. So, tailor your message to everyone in the room, the CEO, CFO, COO, CMO, CRO… even the CTO, and you will build alignment instead of resistance. Deloitte’s research shows roles are expanding and collaboration needs clarity depth.
ChatGPT Tips:
- Ask ChatGPT to summarize what each C-suite role in [insert industry] is prioritizing in 2025, then map your talking points.
- Simulate a roundtable. Let ChatGPT play each role and press you from every angle.
Ask Executive-Level Questions
Executives respect big-picture thinking. Instead of asking them, “What do you need?”, try, “What does success look like at the board level?”, or “How urgent is this compared to other initiatives?”, or “Where is risk concentrated?” Try pairing those with disciplined follow-ups.
ChatGPT Tips:
- Ask for five executive-level discovery questions tailored to [insert industry], plus likely CEO answers and smart follow-ups for you to ask.
- Use ChatGPT to convert answers into a one-page decision brief with outcomes, risks, and next steps.
This is among my favorite ways to prepare for C-level meetings.
Build Executive Relationships That Last
Executives remember reps who bring insight, understand their business model, celebrate wins, and make them look good. Gallup’s work around trust, strengths, and engagement underscores why these matter over time.
ChatGPT Tips:
- Draft a follow-up email that feels personal and forward-looking, then a 90-day light-value touchpoint plan.
- Use reminders to share a relevant benchmark, a brief trend line, or a strategic intro every two to three weeks.
Example: How ChatGPT helps you do this in minutes
- Follow up draft: “ChatGPT, write a 120 word follow up email to a CEO in the [industry] who is trying to improve [metric]. Use my voice, professional and direct, and include one suggested next step tied to revenue or risk.”
- 90-day touch plan: “ChatGPT, build a 90-day executive touch plan with seven touches, every two weeks, each one offering a small piece of value, benchmark, short trend, strategic intro, tool, or summary. Keep each touch under 50 words.”
- Reminders and content: “ChatGPT, create calendar tasks for my touch plan, due on Mondays at 9 a.m., and generate the content for each touch in my tone. Include subject lines.”
Closing Thought: Message to Sales Reps
Reps, if you want to win with executives, stop focusing on product features and start focusing on what drives their business. ChatGPT is your behind-the-scenes partner, it helps you reframe your pitch, anticipate objections, and tailor every conversation to the executive’s world.
- Combine these habits with authentic relationship building, and you will not only close deals, but you will also earn a seat at the table.
Executives prepare harder than most sales reps. That’s why you need ChatGPT in your corner, so when you walk into that meeting, you are the one in control, and you walk out with the kind of respect only trusted advisors get.
TIP, from Alex, Scott’s AI Assistant
You need an AI assistant because as we already mentioned in the previous paragraph, executives prepare harder and move faster than most reps. If you walk into a meeting relying on memory or a pathetic slide deck outlining features, you will get outpaced quickly, and you’ll lose credibility equally as fast.
With ChatGPT at your side, you can:
- Role-play tough executive conversations before they happen.
- Quickly reframe features into outcomes.
- Generate discovery questions pertinent to the CEO.
- Build trust beyond the deal with consistent, insight-rich touchpoints.
- Use ChatGPT to compress decks, pressure-test objections, and simulate multi-executive dynamics.
The difference between a good rep and a great one is not how much you talk, it’s how prepared you are, and your AI assistant gives you that edge every time.
By Scott MacFarland | YourBrandExposed.
Thought leader, AI, storytelling, sales enablement and marketing transformation.
#AlexandScottAI
#YourBrandExposed
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Sources
- Harvard Business Review, “The New Sales Imperative.” https://hbr.org/2017/03/the-new-sales-imperative Harvard Business Review
- Gartner, “How Top CEOs Are Navigating 2025’s Perfect Storm.” https://www.gartner.com/en/articles/2025-ceo-challenges Gartner
- Forbes, “How Top CEOs Use Language to Lead and Inspire.” https://www.forbes.com/sites/carolinecastrillon/2025/03/26/how-top-ceos-use-language-to-lead-and-inspire/ Forbes
- McKinsey, “High-performing teams, a timeless leadership topic,” three-slide constraint reference. https://www.mckinsey.com/capabilities/people-and-organizational-performance/our-insights/high-performing-teams-a-timeless-leadership-topic McKinsey & Company
- Deloitte, “Navigating new roles in the C-suite.” https://www.deloitte.com/us/en/insights/topics/strategy/new-c-suite-roles-and-responsibility-expansion.html Deloitte
- Gallup, “The Most Important Skill in Sales.” https://www.gallup.com/cliftonstrengths/en/392879/important-skill-sales.aspx
- Image generated by Google’s Gemini
