AI-Powered GPT Enhances Real-Time CEO Group Coaching

From Static Sessions to Dynamic Engagement: How a Custom GPT Elevated CEO Group Coaching

Introduction

A business coach leading a CEO peer group wanted to experiment with integrating real-time AI support into their coaching sessions. The idea: instead of limiting AI to behind-the-scenes research or content creation, why not bring a custom GPT directly into the room, offering instant insights, brainstorming prompts, and strategic analysis in real time?

This approach represented a bold shift — using AI not just as a tool for the coach, but as a live, interactive resource for the entire CEO group.

The Challenge

Traditional peer advisory groups rely heavily on facilitator expertise and peer-to-peer input, but:

• Discussions can stall when no one has relevant experience with a particular challenge.
• The range of ideas is limited to the personal experiences of attendees.
• Some CEOs dominate discussions, while others hesitate to speak up, limiting the diversity of solutions.

The coach needed a way to broaden the conversation, introduce new perspectives instantly, and level the playing field — all without undermining the value of peer insights.

The Turning Point

The coach decided to create a custom GPT specifically tailored to the types of challenges and opportunities CEOs in the group typically discuss — from talent retention to AI adoption to scaling strategies.

During sessions, the coach could:

• Prompt the GPT in real time to generate alternative solutions when discussions slowed.
• Ask the GPT to play devil’s advocate, challenging groupthink or overly safe assumptions.
• Use AI to summarize key points from evolving discussions — ensuring quieter voices were captured and recognized.
• Demonstrate live AI coaching techniques, helping CEOs see how AI can support their own decision-making.

This real-time integration of AI into group coaching became a live experiment in blending human expertise with machine insight.

The AI Solution

The custom GPT delivered:

• Real-Time Idea Generation – Instantly providing alternative strategies and solutions when discussions hit a wall.
• Scenario Exploration – Generating “what-if” scenarios and prompting the group to consider overlooked angles.
• Live Summaries and Documentation – Capturing and organizing group insights for follow-up.
• AI Literacy Coaching – Demonstrating how CEOs can use AI as a leadership tool in their own organizations.

Remarkable Progress

The AI-powered approach delivered:

• 4 Hours Saved – Time saved across session prep, in-session documentation, and post-session follow-up.
• Broader Solution Sets – The group considered wider ranges of strategies, thanks to AI injecting new perspectives.
• Stronger Engagement – Participants became more curious and actively explored how AI could benefit their own leadership.
• Richer Takeaways – Sessions resulted in more comprehensive summaries, blending human and AI insights.

“AI broadens the conversation, deepens the insights, and helps CEOs see how AI can work for them, too.”

A Defining Moment

The defining moment came when a typically quiet CEO spoke up, inspired by an AI-generated suggestion.

“Seeing AI deliver instant, thoughtful ideas gave everyone — even the more reserved members — a reason to speak up and contribute their own spin.”

Impact and Inspiration

This AI-enhanced coaching experiment is already reshaping the coach’s approach:

• A New Coaching Model – Real-time AI support is now a core offering, not just a side experiment.
• Client Education Opportunity – CEOs leave sessions not only with business strategies, but with practical experience using AI to support leadership thinking.
• Scalable Process – The same custom GPT can be adapted for other peer groups or 1:1 coaching clients, creating a replicable, value-added service.

Protagonist’s Own Words

“This was a new experiment, but it’s already clear — using AI in real-time coaching isn’t just a gimmick. It broadens the conversation, deepens the insights, and helps CEOs see how AI can work for them, too.”

Conclusion

This case highlights how custom GPTs can enhance not just productivity, but live facilitation and collaborative problem-solving. For coaches working with leadership teams, AI becomes a silent co-facilitator, offering instant ideas, challenging assumptions, and capturing insights — all while modeling the future of AI-augmented leadership.

Call to Action

Want to integrate AI into your own coaching or advisory work? Learn how Simpleacademy.ai’s training helps you build custom GPTs, bring AI into live sessions, and turn coaching into an interactive, AI-enhanced experience that clients value and remember.