From my associate, Grant Tate.
“How are you using A.I. in your executive coaching business?” Tom asked.
“I’m experimenting,” I said, “but there’s so much more I could do.”
We were talking in a live video session with the Chaotic Confluence community — an online group of coaches and professionals exploring how A.I. is changing our work.
Tom leaned forward. “I can see A.I. revolutionizing the business. You’ve probably heard about bots doing therapy sessions by voice or video.”
“Sure,” I said. “Of course, we don’t do therapy, and no one wants robotic coaching. But A.I. can definitely help us in otherways.”
“Like taking notes or drafting follow-up emails?” Tom offered. “That alone would save me hours.”
“Exactly. But it can go much further. Imagine creating a virtual model of your client — a digital twin that mirrors their personality, goals, and learning style. With that, A..I could help design a coaching process uniquely tailored to that person.”
Tom raised an eyebrow. “Really? Tell me more.”
“With clever design, that model becomes predictive — it can simulate how a client might respond or what motivates them. A.I. tools can draw on assessments, your notes, client forms, and even public information from the web. For most executives or entrepreneurs, there’s a surprising amount of data out there. Public interviews, company websites, LinkedIn profiles — all of it helps fill in the picture.”
“Wait — public records?”
“Yes,” I said. “Most people promote themselves online. If you Google a client before your first session, you’re already gathering data. A.I. just does it faster and more comprehensively.”
Tom nodded. “Makes sense. But I still rely on my interviews and notes. That’s where the real insight comes from.”
“Exactly. You’d combine that personal material with the public data. Each time you add something — new notes, a client update — A.I. learns more and refines the model. It’s like having an assistant who remembers everything.”
Tom squinted a bit, uneasy. “That sounds powerful, but…coaching must be private. How do we make sure client information stays secure?”
“Ah,” I said. “Now we’re getting to the heart of it.”
Setting Boundaries with A.I.
“First,” I said, “every coach using A.I. needs a clear set of ethics and guidelines. Clients should know if you’re using A.I. to generate exercises, summaries, or feedback. They deserve to know what data you’re collecting — and how you’ll protect it.”
“Fair,” Tom said. “And the tools we use?”
“Exactly. Be sure your A.I. platform doesn’t use your data to train future models. For example, the free and basic paid versions of ChatGPT allow that unless you opt out. The team version, though, gives you more control. The key is to read the fine print. Know how your prompts and outputs are stored or shared.”
Tom jotted a note. “So if I’m cautious, I should anonymize client data?”
“Yes. Replace names with pseudonyms. Many A.I. tools let you delete individual chats when you’re done — use that feature. And if you want to continue a thread but stay secure, copy your notes elsewhere, delete the chat, and start fresh.”
He laughed. “A little clunky, but I get it.”
“True. But it’s worth the peace of mind. And remember — A.I. systems with memory features can retain what you’ve deleted, so if A.I. makes a mistake or ‘hallucinates,’ correct it. You can literally tell it, ‘Forget this,’ or ‘That fact was wrong — here’s the right one.’
Treat it like a diligent intern with a perfect memory and a short attention span.”
Tom grinned. “That’s a good image. And you’re right — we already manage confidentiality in other ways: phone, Zoom, email. A.I. is just another channel that requires discipline.”
“Exactly,” I said. “In-person meetings in a secure space are still the most private, but A.I. lets us reach people across the globe. Our reach expands —but so must our integrity.”
Tom leaned back, thoughtful. “So A.I. isn’t replacing what we do — it’s amplifying it.”
“Precisely,” I said. “A.I. can extend our insight, but trust remains the bridge between technology and transformation.”
Final Reflection
A.I. doesn’t make coaching less human. It challenges us to be more intentional about the human side — empathy, ethics, and authenticity.
The technology may be new, but the responsibility is timeless.
Close your eyes for a moment and create a picture of your company where 70% of the leaders are resilient and empowered to be adaptable and innovative. Then, create a picture of the competitive advantage the entire organization creates by working in this way. Is that a place you would like to lead and work for? That is what Strategic Coaching can deliver.
Many leaders, especially in government and large institutions, struggle with underperforming employees who drain productivity, morale, and resources. My colleague and I experienced this last week: an organization director, overwhelmed with frustration, has multiple cases of long-term underperformance but feels constrained by bureaucracy, fear of legal retaliation, and a workplace culture that resists decisive action.
I have often observed that upper-middle managers will remain too deeply rooted in their specific departments or functional responsibilities. This results in a limited, vertical perspective. To be viewed as promotable, aspiring executives must develop a horizontal perspective that aligns with the organization’s broader objectives, demonstrating an understanding of enterprise-level dynamics essential for executive roles. This broadened view fosters a deeper understanding of interdependencies, enabling leaders to make balanced, informed decisions and collaborate effectively across functions.
Has anyone ever heard these comments: “Do I have time for one more thing to do?” Or “Coaching helps a little, but I’m not sure it’s worth it.” And, “I’m pretty good at what I do.” The biggie is, “Nobody else understands my business the way I do.”
I’ve been working with generative AI since ChatGPT was released in 2022, primarily exploring how to use the system in the practice of consulting and coaching.
For years I have been a great fan and follower of Stephen Covey. The Seven Habits of Highly Successful People* was first published in 1989 and has been published numerous times since. It has been my bible in book form, cassette tapes, and now CDs. Repetition, we know, is one of the best ways to learn – and with a career that requires a lot of travel, listening and learning are natural ways to pass the time.