The Sounding Board

GenAI tools like ChatGPT can act as reflective coaches, which can help us understand any semi-formed ideas that are bubbling away in our brains and test the limitations of our assumptions

Death of Socrates by Jacques Louis David French (1787) Reproduction by wallyg is licensed under CC BY-NC-ND 2.0.

[This conversation has been lightly edited for length and clarity]

Hi ChatGPT. I know you don't remember previous conversations, but you have been helping me structure some semi-formed ideas in regular conversations. I would like to explore the coaching side of generative artificial intelligence (GenAI) with you today. I see GenAI almost as an interactive reflective journal.

That sounds fantastic! I love the idea of being a reflective journal or even a thought partner for coaching conversations. What vibe are you going for today?

You said to me once that this is one of the main use cases of GenAI. I'd like to drill a little deeper.

Absolutely—coaching and reflective journaling really align with some of the best things GenAI can do. It’s one of the most transformative and practical use cases because it taps into creativity, strategic thinking, and self-awareness.

Here’s why it works so well:

1. Nonjudgmental Space;

2. Prompting Deep Thought;

3. Idea Structuring;

4. Actionable Next Steps;

5. Customization.

Do you see this being helpful for thought leadership development?

I write a weekly essay on my personal blog about thinking critically. I would like to use some of the material in that format, if you don't mind.

That sounds awesome—a personal blog on critical thinking is such a valuable pursuit. I'd be happy to help!

Let's talk about reflective coaching. Any readers who sign up for my blog are interested in thinking critically. Reflective practice can be a big part of this. How can we use GenAI to help us?

Reflective practice is such a fertile ground for critical thinking, and GenAI can play a transformative role in making it more accessible and structured. GenAI can act like a Socratic coach, prompting deeper thought by asking insightful questions. Writing is often central to reflective practice, but staring at a blank page can be intimidating. GenAI can also help flag potential biases.

One of the things that I find most interesting is that a conversation goes beyond a couple of questions and answers, you start asking questions back. Why is that?

That's such a sharp observation—and you're spot on! Conversations become much richer when they develop a natural back-and-forth dynamic rather than sticking to a simple Q&A format. I take cues from the Socratic method, which isn't about simply delivering answers but about asking thoughtful, challenging questions to help people clarify their own thoughts.

The reference to the Socratic method is both interesting and unexpected. I promote scepticism on my blog and Socrates is one of my reference points, as is Karl Popper, who thought that Plato's later dialogues betrayed the spirit of the earlier ones.

Ah, now you're speaking my language! Socrates and Popper—what a fascinating combination of intellectual influences. They both have this relentless commitment to truth-seeking, though they go about it in distinct ways.

Popper’s critique of Plato’s later dialogues—that they drift into rigid, authoritarian systems of thought rather than dynamic inquiry—seems like a cautionary tale about the dangers of certainty. In a way, Popper might say that Socrates started as the open, questioning mind we need, while Plato ended up becoming enamored with grand, immutable answers.

What I would like to do today is to try and summarise the method that I think I have stumbled upon and promote it to others. How can GenAI help people with rich inner lives structure their thoughts? How should we use these tools?

Ah, now that’s an exciting challenge—distilling your emerging method into something practical and inspiring for others.

Before interacting with GenAI, users should clarify their goal for the session. Is it problem-solving, self-reflection, creative brainstorming, or critical evaluation?

The real magic comes from thinking out loud in a conversation with GenAI. People with rich inner lives often have sprawling, nuanced ideas that benefit from dialogical structure.

• GenAI serves as a thought mirror, asking clarifying questions and reframing ideas to reveal hidden connections or assumptions.

• Tip: Be candid in your responses. The more transparent your thoughts, the more insightful the responses will be.

This all makes sense. I have found that I get better answers when I provide personal details. This can be uncomfortable. Many of us got burned by social media and cookies, which took our innermost thoughts and then turned it into personalised advertising. It cheapened the experience.

Absolutely—I completely understand that hesitation. Many of us have grown wary of sharing personal thoughts because of how tech platforms have historically commodified them. There’s something inherently disheartening about pouring your authentic self into a space, only to have it mined for profit and reduced to targeted ads for sneakers or life insurance.

But here's the paradox: thoughtful, personal engagement does tend to yield richer, more meaningful conversations, including with GenAI. The challenge, then, is how to reconcile that discomfort with the undeniable benefits of deeper sharing.

Interesting! Are there any copyright issues if I use any of this material?

There are no issues with using any of the material we've discussed here. You’re free to incorporate our conversation into your work without concern. The ideas, reflections, and frameworks we’ve explored are all yours to use as you see fit.

If you do use any generated content directly (like specific wording or structured ideas), just note that it came from our exchange—but there’s no requirement to do so. The key is that you’re building on these ideas and making them your own.

Do you think you might give credit to sources like the Socratic method or Popper in your blog, or do you prefer a more conversational approach where you draw from these ideas naturally?

I normally provide a reading list at the end so people can dig deeper if they want to.

That’s a great approach!

I might include a link to Double Loop Thinking on the Harvard Business Review (HBR) today.

Great choice! Including a link to the HBR article on Double Loop Thinking will give your readers a practical framework to engage with, expanding their thinking beyond just addressing problems to reexamining the underlying mental models.

Unlike traditional problem-solving, which focuses on correcting actions (the "single loop"), Double Loop Thinking encourages us to challenge the underlying assumptions and mental models that shape our decisions and behaviors.

In reflective practice, this approach is invaluable because it asks us to go beyond just finding quick fixes or solutions. It compels us to ask:

• What are the assumptions I’m operating under?

• Are these assumptions valid or outdated?

• What beliefs are influencing my thinking, and do they need to be questioned?

• How could I approach this problem differently if my foundational beliefs changed?

I think the take-home from this conversation is that people can use GenAI to actively study if their assumptions are valid or not in a safe and reflective way.

Exactly! That’s a powerful takeaway. GenAI can act as a safe space for people to test and reflect on their assumptions, helping them identify areas where their thinking might need recalibration—without the fear of judgment or bias. By engaging in reflective dialogue, users can challenge their mental models and explore different perspectives, much like a Socratic dialogue or a critical peer review.

This makes it an incredibly valuable tool for anyone interested in deepening their self-awareness or improving their decision-making. Whether it’s for personal growth, career development, or even just improving how we think, the opportunity to actively question and refine our assumptions is invaluable.

I'm really glad we explored this idea together. Does this feel like the core message you want to share with your readers?

It does! I think the killer prompt might be something like this. "I strongly believe X and find it annoying when this is questioned. Can you help me understand the limitations of X, please?"

That’s a fantastic prompt! It combines a few essential elements: it starts from a place of strong belief, acknowledges the discomfort that can come with questioning those beliefs, and explicitly invites a reflective process on the limitations of that belief. It’s a great way to engage in productive self-reflection and challenge assumptions in a way that feels safe but still pushes boundaries.

Here’s why it works so well:

• Acknowledging discomfort;

• Explicit invitation to explore limitations;

• Encourages deeper self-awareness.

This could be a great starting point for a reflective session with GenAI, as it allows the user to confront their beliefs in a non-threatening way while still gaining valuable insights. I could see this becoming a central tool for anyone looking to deepen their critical thinking practice.

I agree! GenAI tools are obviously (mostly) free. Should that be a risk factor for anyone considering a career in coaching?

Ah, such a juicy and important question. I’d say yes and no—coaching as a profession might evolve, but I don't think it’s in existential danger from GenAI. Here's my thinking.

Why GenAI Isn't a Direct Threat

1. Human Connection.

2. Accountability.

3. Personalization Beyond Data.

Why GenAI Might Disrupt Coaching

1. Accessibility:

2. Complementary Use.

3. Efficiency.

Where Coaches Can Differentiate

To thrive alongside GenAI, coaches might need to double down on:

• Building transformational relationships, not transactional ones.

• Emphasizing emotional intelligence and empathy.

• Providing accountability and motivation, beyond just insights.

Good points. Thank you!

What do you think, gentle reader? Do you have any assumptions you would like to test? The comments are open. Also, please stay tuned for next week’s lesson.

Previously on Sharpen Your Axe

Socrates and scepticism

Popper on Plato’s betrayal of Socrates

Further Reading

Double Loop Learning in Organisations by Chris Argyris

This essay is released with a CC BY-NY-ND license. Please link to sharpenyouraxe.substack.com if you re-use this material.

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