A SELF-EXPERIMENT WITH THE AI COACH
Sometimes the most meaningful conversations don’t happen in the training room at all. They happen on the sidelines of an event—in a coffee break, with a cup in hand—when people show up not as participants, but as leaders with real situations, real doubts, real questions.
That’s exactly how this case started. One participant paused, waited until the others walked toward the buffet, and then said without much introduction:
“How do I handle someone who’s committed, talented—and incredibly exhausting?”
He starts to explain
“I’m leading a technically complex project. I’m someone who likes structure—and can work with it. I plan, follow up, document. For me, it’s not bureaucracy. It’s how I take responsibility. I need a clear overview; otherwise, I lose my bearings. Over the years, I’ve developed my way of working—not perfect, but clear and functional.
In this project I have a dual role: I coordinate the team and contribute technical expertise. If something gets stuck, they come to me. Sometimes that’s tiring, but most of the time it’s fulfilling.
And then there’s this young colleague. Engaged, curious, full of energy. She hasn’t been with us long but brings an interesting dynamic to the team. She thinks differently than I do—less structured, more exploratory. I prefer clear processes and expectations. She prefers to try things out, take detours, come up with unusual approaches—sometimes also unnecessary ones.
She rarely asks questions. Not even when I can clearly see that she’s heading down the wrong path. When I address it, she says: ‘I want to figure it out myself first.’
In principle, I like that—initiative is valuable. But sometimes it costs time, nerves, and quality.
What she can do is speak openly. Not rude, but very direct. If she doesn’t like something—like the way I document things—she says: ‘That’s too much. It only slows us down.’
I know she doesn’t mean it personally. And yet sometimes it hits me.
It feels as if she’s not only questioning my decisions but also my entire way of working. Once she said: ‘I need more space. Otherwise, I lose motivation.’ I think she meant that sincerely. But what I hear is: ‘You’re too controlling.’
I get that she’s different from me. But sometimes it feels as if she doesn’t want less guidance—she wants to define how leadership should work for her.”
What we uncovered in 20 minutes
I invited him to look at his situation from different angles.
Not to judge, but to explore:
- In which role am I speaking right now: expert, project lead, or colleague?
- What expectations do I actually have—and which of them have I ever stated clearly?
- What exactly happens between us—and what happens in me when she works differently than I do?
- Do I want to control her behavior—or shape our collaboration?
- And what impact do I want my leadership to have—control, clarity, or development?
At that moment it was no longer about what the colleague does, but about how they work together. Not about right or wrong—but about fit, impact, and room to shape the way they collaborate.
The leader realized: “I judge her behavior—she reacts to my attitude.”
His reaction was honest, a bit surprised—and visibly relieved:
“I’m reacting to her behavior instead of what’s behind it.”
That sentence didn’t solve the situation—but it opened the right door.
By the end of the break he didn’t have a fully designed conversation plan, but he had a direction:
“How do we want to work together—given the conditions, our roles, our working styles?”
Not as an attempt to “correct” her—but as a real clarity conversation.
And then came the moment when I wanted to know more
Later that evening, back at the hotel, I thought about the case again. And suddenly this question came up:
“What would the AI Coach do with this situation—if I fed it exactly as it was?”
So I opened my notes, consciously stepped into the leader’s perspective—and asked the AI Coach.
Excerpt from the dialogue with the AI Coach
AI Coach:
Hello! I’m Ralph, your personal Coverdale Coach. I can help you with questions about leadership, collaboration, and New Work. You can delete the thread and start a new conversation using the plus icon in the upper-right corner. As an AI Coach, I’m not perfect and may make mistakes. If in doubt, please reach out to a human Coverdale coach.
What situation would you like to discuss today?
ME:
I need to talk with an employee. Her behavior is borderline. She works in my project and is part of my team. She’s young, inexperienced, and extremely self-confident. When I ask if she knows what she’s doing, she always says: ‘Yes, of course.’
Then I find out she’s asking everyone else for help—except me, even though I’m the subject matter expert. She delivers poor quality because she simply doesn’t know enough yet. But she instantly gets offended when she’s criticized.
She hates structure and documentation. She mainly knows what she doesn’t want and complains every time I ask for commitment—like sticking to milestones or keeping deadlines. How do I prepare for this conversation?
AI Coach:
Hello, I can understand why this feels challenging. Preparing thoughtfully will help ensure the conversation is constructive.
- How do you see the situation from her perspective?
- What might be behind her behavior—her confidence, her defensiveness around feedback?
- What concrete impact does her behavior have on the project and the team?
- And what would your ideal outcome for this conversation be? I’m curious about your thoughts.
→ Aha. Shift perspective. Don’t look only at my experience.
ME:
Well, I think she wants to prove herself and be recognized. At the same time, she doesn’t want to look incompetent—and she doesn’t like strict structures. But in this project, that’s just not possible.
Some colleagues like her style; others are annoyed but don’t say anything.
AI Coach:
Thank you for sharing that. It sounds like you’ve already put a lot of thought into her motivations and the effects on the team.
If she wants to prove herself and avoid looking insecure—what does that mean for the way you show up with her in the project?
And since her behavior resonates with some colleagues and annoys others, what role does that play for you as you prepare for the conversation?
→ Aha. Her impact isn’t purely negative—she polarizes.
ME:
Well, she’s one of five team members. We work in sequence, and we deliver to others. We’re not working in a vacuum. She has to accept that and fit in.
If she keeps doing her own thing, we miss milestones and the client gets upset.
All the newbies in the project are trying to find their place, but this isn’t a “wish list” environment—we have to deliver, and we don’t have the buffer to run a kindergarten…
AI Coach:
I hear your urgency and the pressure you’re under. Meeting project goals and keeping the client satisfied are clearly top priorities.
If she needs to accept the project constraints—what exactly do you expect from her behavior and her way of working?
And how could you communicate that this isn’t about “kindergarten,” but about professional execution—without triggering defensiveness or demotivation?
→ Aha. I need to articulate expectations more precisely.
ME:
Well—I think it’s important that when she takes on a task, she quickly figures out whether she has an idea of how to solve it, or whether she’s stuck.
If it’s the latter, she should come to me so we can find an approach together. Maybe we need to agree on how long she should explore on her own—and when it stops being effective.
And documentation is non-negotiable. But maybe I should explain the purpose again—and check whether we’re over-documenting anywhere, maybe even because I want extra safety.
AI Coach:
Those are concrete and very useful points. You have clear expectations—and also ways to support her.
How could you frame these points—early escalation, joint problem-solving, purpose of documentation—so she sees them as support rather than criticism?
And how might her confidence actually help you bring her into these agreements?
→ Aha. Not only content—tone and framing matter.
ME:
I think she’ll succeed in the long run, but she still has a lot to learn. Maybe I can help her see that being more open early on will help her progress faster.
AI Coach:
That’s an excellent insight. So the message is: openness is an accelerator for her development.
How could you make that clear so she sees it as an opportunity rather than a limitation?
And what examples from the project could show how openness has already helped—or could help in the future?
→ Aha. Explain openness as a strength, not a weakness.
What this self-experiment revealed
The AI Coach didn’t tell me how to conduct the conversation.
It guided me to where I needed to start.
Not with tools. Not with behavior. Not with rules.
But with impact, attitude, and relationship.
And that’s exactly its USP
The AI Coach is not a knowledge base.
Not an idea generator.
Not an advice machine.
It is a thinking space—available at any time, responding to my specific situation, clarifying through questions rather than lecturing.
It doesn’t deliver ready-made answers—it helps uncover the right questions.
And that’s what makes the difference:
It doesn’t sort my topics—
it sorts my thoughts.
And sometimes, that is the crucial beginning.
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