AI in Executive Coaching: What We’re Seeing, Testing, and Learning

By Brian Underhill, CEO, CoachSource

CoachSource does not have a financial or other interest in any of the tools shared within.

At CoachSource, we’ve always been curious about what’s next in leadership development. So it’s no surprise we’ve been actively exploring how artificial intelligence is showing up in the world of executive coaching—and what it could mean for coaches, clients, and organizations around the globe.

We’ve tested some of the earliest AI tools, watched others evolve in real time, and asked tough questions about where technology helps—and where it doesn’t.

Starting Early: PocketConfidante and the First AI Coach

Long before ChatGPT made AI part of everyday life, we experimented with PocketConfidante, one of the first known AI coaching tools. It offered reflective, guided conversations using early natural language processing.

The concept was powerful: Could you replicate a coach-like presence between sessions—or even without a coach at all? The technology wasn’t quite ready, but it opened the door to what came next.

A New Wave: LLMs and the Rise of Conversational AI

With the arrival of large language models (LLMs), AI tools have become far more natural, adaptive, and nuanced. We tested Coach Vicci, an AI assistant designed to help clients prepare for coaching sessions and reflect between them. It’s not trying to replace a human coach—but it can support the journey in thoughtful ways.

AI Tools We’re Watching

CoachM – A behavior-focused coaching platform using AI for nudges, goal-setting, and integration with live coaching
Rypple (reimagined) – The return of a well-known platform, now focused on performance and feedback, with AI capabilities designed to support real-time coaching and growth conversations at scale
Yoodli – An AI public speaking coach providing real-time feedback on filler words, pacing, tone, and clarity—valuable for executives refining their communication
Ovida – A training platform for coaches, using AI simulations to replicate live coaching sessions and provide immediate, structured feedback
Clarity – A mental wellness and journaling app that uses AI to guide users through reflection, emotional processing, and self-awareness—bridging personal well-being and self-coaching
Coach Clones – We’re seeing a rise in “digital replicas” of well-known coaches, trained on their voice, philosophy, and methods. CoachSource-affiliated coaches like MarshallBot, John Baldoni, and Philippe Grall have experimented with AI versions of themselves—raising fascinating possibilities around legacy, scale, and knowledge transfer
360 Report Drafting Tools – AI is now being used to analyze 360 interviews, stakeholder feedback, and written documentation, generating first-draft coaching reports and leadership summaries. These tools can save coaches hours of synthesis time while maintaining accuracy and thematic clarity—though human interpretation still remains essential.

The Upside—and the Cautions

There’s a lot to like: greater access, scalable insights, always-available reflection tools, and more consistent support between coaching sessions. But AI in coaching also raises critical questions:

• How is the data being used?
• Who has access to client reflections and insights?
• Can a machine truly understand context, values, or human emotion?
• Would top executives really use these tools?

Adoption among senior leaders remains mixed—some are intrigued, while others prefer human connection. Effectiveness may depend on positioning, privacy, and perceived value.

AI’s Limitations: Looking Back, Not Forward

CoachSource provides executive coaches primarily to senior leaders in large global organization where complexity, nuance, and ambiguity tend to be high.

As we explore the role of AI in executive coaching, it’s also important to acknowledge a core limitation: AI, by design, draws from existing data—it reflects the past more than it predicts the future. This means that while it can surface patterns, themes, and best practices from what has worked, it may struggle to respond wisely to new, ambiguous, or unprecedented leadership challenges—situations where creativity, foresight, and human judgment are essential.

Additionally, biases—both subtle and systemic—can still be embedded in AI tools, shaped by the data they were trained on. This presents risks when coaching senior leaders navigating complex organizational, cultural, or global dynamics. Leaders need insights that challenge assumptions, not reinforce them.

That’s why we see AI as a complement, not a compass. It can inform and augment a leader’s growth journey—but navigating uncharted waters still requires the wisdom, empathy, and contextual sensitivity that only a human executive coach brings (so far).

Where We Stand

We’re not just watching this trend—we’re engaging with it firsthand. We’re testing tools, listening to coaches and clients, and staying grounded in what makes coaching effective: human connection.

We see that AI may be a supplement, not a substitute to human coaching. It’s a way to enhance self-awareness, enable follow-through, and provide broader access to developmental support. But at the end of the day, transformational leadership still requires transformational relationships. Human-to-human.

CoachSource Still Uses Human Coaches

A joke I once shared with the late David Peterson: CoachSource still uses human coaches!

While we’re actively exploring AI, it’s important to emphasize that our work remains rooted in human connection. Across our global network, we partner with experienced, credentialed professionals who bring empathy, insight, and real-world leadership expertise to every engagement.

No algorithm can replace the depth of trust or the nuance of a coaching conversation. We believe technology can support coaching—but it doesn’t replace the human heart of it. Our approach is, and always will be, human-first.