2203 - Can AI Truly Replace the Human Coach? The Future of Coaching in the Age of Technology with Ted Whetstone

7 Jun 2025 · 21 min

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Podcast Summary: The Thoughtful Entrepreneur - Episode 2203

Episode Title Can AI Truly Replace the Human Coach? The Future of Coaching in the Age of Technology with Ted Whetstone

Episode Description In this episode, host Josh Elledge interviews Ted Whetstone, an executive coach and expert in transformational leadership. The conversation revolves around the nuances of coaching, the role of introspection and philosophical inquiry in leadership, and the intersection of technology and coaching, particularly the impact of AI.

Key Themes and Discussions

  1. Transformational Coaching
  2. Ted's Philosophy: Coaching should move beyond task management to inspiring real change in leaders.
  3. Core Approach: Emphasizes deep introspection, philosophical reflection, and a values-based approach to coaching.
  4. Target Audience: Focuses on C-suite leaders and executives managing organizations with revenues over $100M.
  1. The Role of Nature and Reflection
  2. Nature as Inspiration: Ted shares how nature walks help clarify his thinking and foster introspection.
  3. Philosophical Influences: Draws inspiration from historical thinkers like Darwin and Da Vinci, aiming to cultivate critical thinking in his clients.
  1. Empowering Leadership
  2. Facilitating Growth: True leadership is about empowering others rather than solving their problems.
  3. Asking Questions: Ted emphasizes the importance of asking empowering questions to inspire intrinsic motivation within teams.
  1. The Impact of AI on Coaching
  2. AI's Capabilities: Acknowledges that tools like ChatGPT can assist in cognitive processing but cannot replace the human connection essential for meaningful transformation.
  3. Human vs. AI Interaction: Highlights the nuances of human interaction that AI cannot replicate, particularly in recognizing emotional cues and blind spots.
  1. Leadership Challenges
  2. Overcoming Managerial Mindset: Discusses how leaders often fall into the trap of managing rather than inspiring, which can lead to feelings of overwhelm.
  3. Shifting from Management to Facilitation: Encourages leaders to invest time in developing their team's critical thinking and problem-solving skills.

Episode Highlights

  • Reflection and nature enhance leadership decision-making.
  • Great leaders ask questions that facilitate self-discovery rather than offering immediate solutions.
  • Motivation vs. Inspiration: The critical difference in driving team engagement.
  • The evolving role of AI in coaching and its limitations.

Conclusion Ted Whetstone emphasizes that transformational leadership isn't about having all the answers but creating an environment where others can discover their potential. His insights underscore the importance of introspection, empowering conversations, and recognizing the human element in coaching.

About Ted Whetstone

  • Background: Transformational executive coach focusing on high-level leaders.
  • Website: [Ted Whetstone's Website](http://www.tedwhetstone.com/)
  • LinkedIn: [Ted Whetstone on LinkedIn](https://www.linkedin.com/in/tedwhetstone/)

Listening Details

  • Host: Josh Elledge
  • Podcast: The Thoughtful Entrepreneur
  • Duration: 15-25 minutes

Additional Resources

  • If you're interested in becoming a guest, visit [Up My Influence - Podcast Guest Application](https://go.upmyinfluence.com/podcast-guest).

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This episode provides valuable insights for business leaders looking to enhance their leadership skills and navigate the complexities of modern coaching in the age of technology.

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Transcript

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0:05Hey there, thoughtful listener. Are you looking for introductions to partners, investors, influencers, influencers, influencers, and clients? Well, I've had private conversations with over 2 ,000 leaders asking them where their best business comes from. I've got a free video you can watch with no opt-in required where I'll share the exact steps necessary to be 100 % inbound in your industry over the next six to eight months with no spam, no ads, and no sales. What I teach has worked for me for over 15 years and has helped me create eight figures in revenue for my own companies. Just head to upmyinfluence.com and watch my free class on how to create endless high-ticket sales appointments.

0:51Also, don't forget, the thoughtful entrepreneur is always looking for great guests. Go to upmyinfluence.com and click on podcast. I'd love to have you.

1:05with us right now it is ted whetstone ted you're a transformational leadership expert you're an executive coach and speaker you are found on the web at ted whetstone.com to our friend that's listening right now just click in your app in your podcast app right now so you can follow along but ted it's great to have you morning josh nice to be with you yes Likewise. So, Ted, before we get into the work that you do, and I'm really excited to talk about high-impact leadership and, of course, your take on that. When no one else is around or the cameras are off, so to speak, what are you currently doing for fun?

1:43What are you geeking out on? What are you into lately? Wow. Okay. Well, so many things, of course. AI alone, you can geek out on, but that requires you to be in front of your computer. I also am an avid writer. I love to philosophize and write again in front of a computer. So when I'm not in front of a computer, I just look, I live on the coast right here in Santa Monica, California, and there is nothing greater than just appreciating the beauty of nature. So I love walks. I love to get to the beach and I'll pet every dog around. So nothing, nothing designed as much as just taking on life and stepping away from the desk.

2:22I love it. I love it. Were you always into, and this is just purely out of my own kind of awareness as well, it has really only been lately that I've really started diving into Stoicism and Buddhism, you know, kind of from a philosophical standpoint. point. Now, I've always loved the topic of critical thinking and have really been obsessing on it lately. Can you maybe share a little bit more about like what's intriguing you or getting your brain? Like, what do you what is your brain munching on lately? Well, so I'm fascinated with human behavior. I'm a physics person back in college, and I think I've always been inspired by the greats, whether it's Darwin, Da Vinci, Galileo, because they saw things differently.

3:12And so I look, I'm what I call a breakthrough thinker, and I get stuck. So I'm kind of fascinated, what is it about this species, as smart as we are, that we get in our own way? And so it really started, there was actually an NPR special called These Things I Think about 15 years ago. I thought, what do I think? And that began a journey of really taking a look at, you know, what are my unique thoughts? What do I think about the world? What I reflected on was back to my talks about, or my walks in nature. You know, nature is a big ecosystem. Everything's interactive. It just works together. Humans are the only ones that get in our way and like stop that from happening.

3:57And And so it's really, we've come to think of the world as we experience it. And my question is, where's the gap between how it really works and how we think it works? And how can we close that gap? And that's sort of what I've been geeking out on is you could call it philosophy. You could just call it thinking for yourself. But I don't think enough of us to do that and really ask ourselves, what do I think? Yeah, yeah. Well, Ted, it sounds like, and based on kind of browsing through your website, this sounds like yes it sounds like a fun it sounds like passion but it also sounds pretty close to what you end up doing in your work do you mind sharing a little bit about the work that you do with your clients what that looks like yeah no I appreciate it yes it does sound like the work I do because I've finally been able to craft my work as a function of who I am yeah whereas so many of us end up doing what we do because we're trying to get the money And that's the kind of leaders I focus on.

4:54So yes, of course, that led me to, look, I was a left brain management consultant for big companies forever. And at the end of the day, I was like, okay, we fixed process and profit and all these things. And what about the people? And it really hit me that too many companies do not engage the people aspect other than as a function. And boy, if you just, they say you have two ears and one mouth, use them in that proportion. Management does the opposite. And so I really became interested in working with people to, A, help them identify their own sense of purpose, clarity, creativity, right, within what they do.

5:32But then to really lead from, I always say leaders, people think leaders lead other people. I say leaders cause leaders. And suddenly clients' heads turn and they realize it's not about you being a big deal. It's about you empowering others to step up. And that shifts the game massively. So at some point, maybe the whole world will have that philosophy where we're here to empower others rather than us be the big deal. Yeah. Well, Ted, who do you work with and what does that look like? Yeah. So look, leadership happens at all kinds of levels. It so happens that leaders who are willing to invest in themselves can justify the kinds of fees that a management or a leadership coach can provide.

6:20But it tends to be leaders of, look, for me, it's about$100 million companies on up. It's either C-suite individuals and or people who have business units of that size, because one, they can afford a coach like me. And it's not that I'm expensive. It's the justification, right? The ROI is seven to 10 times on coaching. You can see that on any number of stats across the internets. But But what happens is once they get to a certain side, the complexity, the scale gets to the point where none of us can manage all this. And we have to learn how to work together. What is it? You want to go fast, go alone.

7:00You want to go far, go together. And that's a big leap for people to get to. And when you get to that scale, that's what's required. Do you work with individuals? Are you working with organizations? or are you working with individuals who are in organizations? Where do you find yourself? It's a great question. When I was new to the coaching business, I hadn't realized either. There is individual coaching, and that's what I do. I do one-to-one. It's a private setting. It's completely confidential. It's the only time, quite frankly, a leader has a safe space to say, hey, there's things I just don't know.

7:36I don't understand. I'm fearful, et cetera, right? There's a great coaching modality of coaching teams. I don't do that, but that's a very different approach and very powerful and important. I like the one-to-one for two reasons. One, the privacy and the impact. But of course, the other is to really the kinds of clients that I love to work with. They want to do something different in the world. They want to make an impact beyond making a paycheck. And it really takes the kind of conversations we're having to dig into that, that sometimes a team environment, you can't quite get to those levels of intimacy.

8:12Yeah. And Ted, you had mentioned, you know, how much you're geeking out on AI. And I probably spend, I'd say, on average, at least an hour to two hours a day actively using AI-enabled tools, primarily ChatGPT and everything out of that. And it has been a huge life upgrade. And obviously, one of the use cases, you know, for ChatGPT is I get a lot of coaching out of it. You know, big, complicated things that sometimes I just need to process out. Now, in your work as a coach, obviously, you're probably working with plenty of tech-savvy leaders as well. Where do you see the role of inhuman coaching where that's probably going to be a way more effective modality for the outcomes that we want to create there versus what can likely be done in, you know, with your chat GPT therapist?

9:13Yeah, no, it's a great question. In fact, you know, I think any of us sort of have to be concerned about what AI is going to do. I just, you know, finished getting some headshots using an AI type thing. And they're fantastic. And it's not about the money so much as the time saved and the flexibility and whatnot. So great. Right. The thing they can't do is get you to smile that one way. Right. That really captures your essence. Right. That someone who is, you know, directing you can pull out of you. And I think it's similar for coaching. You're absolutely right. You can ask questions and get very meaningful answers.

9:49The better the question, the better the answer. That's true for humans, but true for A.I. And so then the difference becomes, OK, well, why do we need the human? And there's probably two things with that. One of them, it's not about our knowledge anymore. In fact, AI knows well more than I do, right, across all kinds of training. So it's not the what. It's more about the, I wouldn't even say the how, but it's the thinking behind the knowledge. So it's not about information. You want information, it's great. If you want someone to read, you know, an old boss of mine and forgive the language here, he says, I don't mind you BSing me, but you're BSing yourself.

10:31And I think that's what AI can't detect is when we are saying the right things. And yet, yeah, it's not aligning with what we are seeing and experiencing the person. And that's their blind spot. That's what the human still can do better than anybody else. You know, even prompts that I've tried evoking, you know, because that's I think for anyone who is who is genuinely, you know, introspective, who is genuinely trying to become the best version of themselves. You know, they're going to welcome that, you know, where are my blind spots? You know, what am I missing? Yeah. And I'll be, you know, even those prompts that are kind of designed to evoke that it's, it's not real great.

11:19Right. And it's, it's, it's the, I think there's a lot of nuance that, you know, it's like, if someone is answering a question, you're talking with them and you're watching them over zoom, you know, you're going to see like, you know, like an experienced poker player is going to be able to read, you know, poker tells as an experienced coach. You'd be like, yeah, you said this, but that's not what your face said, you know? And so, you know, again, will we get there? I don't know. But, you know, certainly for right now, you know, in terms of like, if you want bang for the buck, I'm still pretty convinced that nothing beats a remarkable coach.

12:01Would you mind, Ted, I don't know if you want to opine on that anymore, if you want to talk about the fact of, you know, maybe some examples of additional challenges that you find that leaders often bear, and how do you help them overcome some of that weight, that gravity that they're feeling? Yep, yep. Well, two things. One, just a comment on the previous comment. If this were true, and look, Zoom, we've had Zoom since Skype, right? But it wasn't until COVID that we had to use it. And guess what? This is great. It's very good. You're in Florida. I'm in California. We're doing great together. It's not quite the same as getting together.

12:47And so you can get so far. But if you and I were going to do business together, we'd want to break bread and have drinks and really get to know each other. You know what I mean? So there's, and it's not, it feels like the nth degree, but I think you can saturate at just information and not depth of experience. And I think that that's the piece that we're forgetting now. It's the human experience portion, which gets to your second question. You know, I have, I had a leader that, you know, very effective, got promoted up. And he said, I'm just overwhelmed. My people keep coming to me with problems and I'm busy putting out fires.

13:23He's acting like a manager. And I talk about the difference between a manager and leader, sort of that same distinction I gave to you previously. And it's also that you want to go far, go together. Investing a little more time in helping that person who reports to you learn to develop their thinking process. And you do that by asking, once again, questions, not talking out your mouth. So the hardest thing for a leader to do is not to be the one talking. to be the one asking questions and then helping people, you know, how did you come to that? Or what makes you think that? And help uncover those underlying beliefs, right?

14:04Assumptions that we don't even realize we're operating by. And by doing that, that person starts to gain confidence in themselves. There's a difference between self-confidence and confidence. Confidence is knowing how to do something. Self-confidence is I've never done it, but I'm pretty good at figuring things out, I think I can get there. And the more we can get them to our people, the better. So that's the kind of thing that happens when the leader is struggling to be more effective and they think it's about them and they realize it's not anymore. And it's how well they can cause others to become more effective.

14:39And all of a sudden he says, geez, I don't have anyone knocking on my door. I'm wondering what I do with myself. I said, go, go, go, find something to make a big impact. I wanted to point this out. Ted, you're a great follow on LinkedIn, I should point out. You shared something, and I was hoping maybe I could get your take on this, because I agree with you. You shared a quote from Peter saying from the Fifth Discipline, you can't substitute external pressure for internal aspiration. And then you added, personally, I feel like managers motivate from the outside while leaders inspire from the inside.

15:15Um, how can we be, how can, how can we be more cognizant of that dynamic? Um, when oftentimes there's just stuff that needs to get done. And so it's easy, it's easier to motivate from the outside. Um, it might take a little bit more patience and grace to inspire from the inside. It's just going to have to be habit. You know, you know what I honestly do? Look at people, these things on the side of your head. if we had these, these are funny looking. To our audio listeners, Ted is pointing at his ears. Yeah. And I've got big ears and a bald head. And so that can be a cue when you talk to people say, oh, that's right.

16:02Let me just slow down for a microsecond to, before I just run off and execute that request, let me just ask a question or two. and inevitably that helps the person often clarify what it is they need to get done why and then you get to spend the time on what's really important versus we try to run off so i hear you it is the toughest thing is that time time time go go go and we need to train each other that when i'm asking a question is it is actually in search of future efficiency and effectiveness than trying to be obstinate in the moment. And when we have that understanding, we realize that that's an investment in not only our relationship, right?

16:48But it's an investment in kind of thinking like, do you think ants have a rule book that they follow? They just sort of see what needs to be done and they adjust individually to the collective need. I think as we start to develop the same in organizations, it becomes less of a Taylorism. Hey, you all do your individual tasks and it becomes, Hey, I've got some extra bandwidth, you know, where can I, where can I support? Um, again, theory practice, it's going to take those triggers. I like to look at ears and it'll give us those triggers to stop, think, and ask before we just run off and do, do, do.

17:27Yeah. Um, so your website, uh, Ted is tedwhetstone.com. Um, you have some great resources. You have a great blog. For a friend that's been listening to our conversation, where do they go from here? Yeah. So, I mean, honestly, the best place to go is you'd go to my website, Ted Whetstone. It's with an H. A whetstone is a sharpening stone. I like that. Yeah. And never a dull moment. The look, the best way to do is have there's a click right at the top of that website where you can just book a consultation call. And the reason is, A, do we get along? Is your challenge something that I can help you with?

18:05Or to your point, here's some resources. Don't hire me. Go to chat GPT for all that. There's no sense in wasting people's time. But that's the best way to A, create rapport. B, help someone figure out what it is they're really struggling with. Identify them the right resource. And exactly as you're doing, connect them to people. But my best marketing is people who say, hey, this TED guy, he's sincere. He's authentic. He knows some things. you know, not for me and my situation, but for what you just described to me, you ought to talk to him. So anybody, I love having a 45 minute call with anyone just as you've opened your door today.

18:39And I appreciate it. Yeah. Awesome. Ted whetstone.com. Ted, that's your brand, your transformational leadership expert and executive coach and speaker. Ted, thank you so much for joining us. Thank you. It's a pleasure to be here. Appreciate it, Josh.

18:58Thanks for listening to the Thoughtful Entrepreneur Show. If you are a thoughtful business owner or professional who would like to be on this daily program, please visit upmyinfluence.com and click on podcast. We believe that every person has a message that can positively impact the world. We love our community who listens and shares our program every day. Together, we are empowering one another as thoughtful leaders. And as I mentioned at the beginning of this program, if you're looking for introductions to partners, investors, influencers, and clients, I have had private conversations with over 2000 leaders asking them where their best business comes from.

19:40I've got a free video that you can watch right now with no opt-in or email required where I'm going to share the exact steps necessary to be 100 % inbound in your industry over the next six to eight months with no spam, no ads, and no sales. What I teach has worked for me for more than 15 years and has helped me create eight figures in revenue for my own companies. Just head to upmyinfluence.com and watch my free class on how to create endless high-ticket sales appointments. Make sure to hit subscribe so that tomorrow morning, that's right, seven days a week, you are going to be inspired and motivated to succeed.

20:22I promise to bring positivity and inspiration to you for around 15 minutes every single day. Thanks for listening and thank you for being a part of the Thoughtful Entrepreneur Movement.

From the publisher
How Transformational Leaders Inspire Real Growth with Executive Coach Ted Whetstone

In this episode of The Thoughtful Entrepreneur, host Josh Elledge speaks with Ted Whetstone, executive coach and transformational leadership expert. Ted shares how deep introspection, philosophical inquiry, and a values-based approach to coaching can empower today’s leaders to move from managing tasks to inspiring real change. If you’re a business leader looking to develop teams that think critically, grow independently, and lead with authenticity, this conversation offers valuable and actionable insights.

Transformational Coaching Rooted in Philosophy, Nature, and Reflection

Ted Whetstone isn’t your average executive coach. Drawing inspiration from the lives of breakthrough thinkers like Darwin and Da Vinci, Ted weaves his passion for writing and philosophical reflection into his leadership practice. Living in Santa Monica, he finds daily clarity in nature walks—balancing introspection with strategy. This connection to self-awareness and nature forms the bedrock of his coaching philosophy.

Professionally, Ted focuses on C-suite leaders and executives managing $100M+ organizations. His approach emphasizes individual one-on-one coaching to help leaders uncover blind spots and clarify thinking. He believes true leadership is about facilitating others’ growth, not solving problems for them. Through empowering questions and thoughtful engagement, Ted helps leaders inspire intrinsic motivation in their teams—transforming reactive managers into proactive visionaries.

He also highlights the evolving role of AI in coaching. While tools like ChatGPT can support cognitive processing, Ted emphasizes that no machine can replace the nuanced, human connection required for real transformation. His message? Use AI to assist, but never forget the power of presence.


About Ted Whetstone

Ted Whetstone is a transformational executive coach who specializes in working with high-level leaders across complex organizations. Drawing from decades of experience and a deep philosophical grounding, Ted empowers clients to cultivate introspection, overcome leadership plateaus, and drive meaningful impact within their teams and industries.

Links Mentioned in this Episode


Episode Highlights

  • How reflection and nature fuel better leadership decision-making
  • Why great leaders ask questions instead of offering solutions
  • The critical difference between motivation and inspiration
  • How to shift from management to facilitation in team development
  • The role and limits of AI in leadership coaching

Conclusion

Ted Whetstone reminds us that transformational leadership isn’t about having all the answers—it’s about creating the space where others can discover their own. From strategic introspection to empowering conversations, his approach helps leaders unlock sustainable growth within themselves and their teams. If you're looking to deepen your leadership impact, Ted’s insights provide a compelling starting point.

Apply to be a Guest on The Thoughtful Entrepreneur: https://go.upmyinfluence.com/podcast-guest


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