Unlocking Self-Coaching with AI: How the Tool Guided Me Through a Business Challenge

In an age of rapid change, mastering self-leadership and self-management has become essential. It is an essential skill for any leader. One of the most valuable tools in my own journey of self-leadership has been self-coaching. Practicing self-coaching regularly helps me stay accountable, navigate challenges, and make strategic decisions that align with my goals. Traditionally, people have relied on professional coaches or mentors for guidance, but with the right questions and frameworks, I’ve found much of that insight can come from within. My training and experience as a professional team coach has certainly helped, giving me tips and tricks I can apply to coach myself—many of the same ideas I use with clients and teams work just as effectively for self-coaching.

Now, with the rise of AI tools, there’s remarkable potential for technology in self-coaching. Could AI become an effective tool for self-leadership? Can it ask the right questions, encourage meaningful reflection, and help me unlock insights much like a self-coaching session would? To find out, I conducted a little experiment. In this article, I’ll walk you through a coaching session I did with ChatGPT, exploring a real business challenge and seeing just how effective AI-driven self-coaching can be. And at the end of the article you get free access to the tool I created and used! So, let’s do it!

The Experiment

To explore the potential of AI as a self-coach, I decided to try an experiment: using ChatGPT to tackle a business challenge of mine. My goal was to see whether AI could guide me through a structured, reflective process, helping me uncover insights and take practical steps forward, with the hypothesis that AI can be a great tool for that.

I'm currently working on an idea involving assessments—let’s keep it vague for now, to avoid revealing all the details. Using a customized GPT I created with the help of ChatGPT itself, I conducted a coaching session that I’ve transcribed below. I’ll walk you through that session step by step, highlighting the questions ChatGPT asked, the insights that emerged, and how the AI guided me toward potential solutions. Along the way, I’ll share the twists and turns of the conversation and how it stacks up against a human coaching experience.

I’ve slightly edited my responses, as my spelling tends to look like a tangled fishing line when it’s not a top priority. Interestingly, ChatGPT handled my typos and half-finished sentences remarkably well.

(I also removed parts of the conversation that aren’t ready for the public just yet.)

The Session

ChatGPT:
What do you want to discuss today?

Before we dive in, let’s outline how we’ll work together. I'll guide you using the GROW model:

1. Goal – We’ll clarify what you want to achieve.
2. Reality – We’ll explore where you currently stand regarding this goal.
3. Options – We’ll consider possible paths you could take.
4. Will – We’ll focus on your commitment and next steps.

As your coach, I’m here to help you unlock your own insights. I’ll be asking questions to spark new perspectives rather than giving advice. How does that approach sound to you, and what would you like to focus on today?

ChatGPT:
Great! So, let's start with the Goal. What would you like to achieve or explore through our conversation today?

ChatGPT:
Got it. So, your goal is to effectively sell your new services, even without a strong background in marketing.

To make this goal more focused, what specifically would success look like for you? For example, is it about reaching a certain number of clients, mastering a particular marketing skill, or something else?

ChatGPT:
It sounds like your goal is to build awareness and generate interest in your product as you launch the MVP.

Before we dive into options, let's clarify the Reality. Who are the people you ideally want to reach? What types of people or businesses would benefit most from your service?

ChatGPT:
It sounds like you’re honing in on leaders in technical fields, specifically agile teams within English-speaking IT organizations—an audience that aligns well with both your background and the focus of your MVP.

To get a clearer view, what do you think these agile team leaders value most when considering new services? What challenges are they facing that your service could help solve?

Part of the coaching session deleted here for brevity (and secrecy).

To summarize, this part of the session led to the idea of hosting a webinar.

The Session Continues...

ChatGPT:
That’s a powerful approach. By centering on actionable strategies to strengthen psychological safety, you’re offering immediate, practical value. Emphasizing that your tool supports the crucial "next step"—an accurate assessment and an actionable plan—positions it as the key to making real progress, after they’ve set their vision.

How might you demonstrate the assessment and action-planning process in a way that lets them experience its simplicity and impact firsthand during the webinar?

ChatGPT:
Yes, showing real examples from the assessment and report—especially with insights from beta testers—could be incredibly effective. It lets potential users visualize how the tool would apply to their teams and shows tangible outcomes.

As you prepare these examples, what key points or “aha moments” do you hope they’ll see that might make them think, "I need this for my team"?

ChatGPT:
Those are powerful questions that cut right to the heart of why leaders need this kind of tool. By prompting them to consider how psychological safety impacts honesty and openness, you're setting up the perfect "aha moment"—that traditional methods of gauging team sentiment might fall short when psychological safety is lacking.

How could you build these questions into the webinar, perhaps as interactive moments, to engage leaders and let them reflect on their own teams?

ChatGPT:
Exactly—those challenging rhetorical questions can stir reflection and make the need for a tool like yours crystal clear.

What do you envision as a powerful closing message to leave them thinking about your solution?

ChatGPT:
How about a message that ties back to their goals as leaders? Something like:

"You want a team that’s not just performing but thriving—where every voice is heard and valued. This tool can help you bridge the gap between where your team is and where it could be. Start by understanding what they truly think, and take action to build a team dynamic that supports openness, trust, and growth."

Does this resonate, or is there a specific idea you’d want to include in that final message?

ChatGPT:
I’m so glad it resonates! Building on that foundation, you could add a call-to-action, inviting them to take the next step with a free or discounted trial, positioning it as their chance to start building that thriving, open team right away.

How does that feel as a closing strategy?

ChatGPT:
That’s an excellent touch! The QR code makes it easy and immediate for them to take action right from the webinar. Offering a free or heavily discounted assessment right then creates a seamless path from awareness to engagement.

What steps do you need to take next to get this webinar ready?

ChatGPT:
That sounds like a solid plan—perfect timing to gain momentum! Getting the beta ready will give you those real examples for the webinar, and continuing those conversations can help set up a collaborative launch.

What’s one key action you can commit to this week to move both the beta and webinar planning forward?

ChatGPT:
Great focus! Getting the pre-beta ready will give you valuable insights and examples, making your webinar that much stronger.

What’s your timeline for finalizing this, and what support or resources would make this step easier for you?

ChatGPT:
Perfect. That’s a clear, achievable timeline to work toward.

To stay on track, what’s one specific task you’ll tackle first to make sure you’re ready by next week’s end?

ChatGPT:
Touché! One clear goal is all you need to drive focus and progress. End of next week, ready for pre-beta testers—it’s solid.

What will success look like to you when you hit that goal?

ChatGPT:
Absolutely! Looking forward to hearing how it all progresses in the next session. You're building something impactful here—can't wait to see it take shape. Good luck with the pre-beta launch!

Conclusion

This experiment demonstrates that AI can indeed be a powerful tool in self-coaching and self-leadership. Hypothesis proven. Through a simple, tailored AI tool like the one I created, individuals can engage in meaningful self-reflection, explore their goals, and define actionable steps—all essential components of effective self-leadership. The structured prompts and reflective guidance AI offers encourage accountability, clarity, and insight, mirroring many of the benefits of a traditional self-coaching session.

My hypothesis was that self-coaching could be done effectively with AI’s assistance, and this experiment confirmed that. While AI may lack the nuanced empathy of a human coach, it still asks the right questions, stimulates valuable introspection, and encourages accountability—qualities that are invaluable in self-coaching. For anyone committed to developing self-leadership, this tiny tool shows that AI can be a valuable ally on the journey.

A Challenge

I wouldn’t be the coach I am if I wasn’t, as usual, challenging you in the end:

• How well do you truly know your own motivations, strengths, and blind spots?
• How often do you challenge yourself to step back and reflect on where you’re headed—and why?
• What could be a next step in increasing your self-leadership skills?

Try it Yourself

If you have a paid ChatGPT account and want to try self-coaching with AI, just enter your name in the box below, and you’ll receive an automatic email with the link to this basic self-coaching GPT. No strings attached.

Last updated Nov 20, 2024