What I Learned Teaching AI to Have Hard Conversations

A few months ago, I started building something I had been thinking about for a long time.

For almost two decades, I have walked managers and leaders through the most uncomfortable conversations of their professional lives. Performance feedback that needed to land. Terminations that needed to happen with dignity. Investigations into things people did not want to talk about. The pattern is always the same. Smart, capable leaders freeze in front of a conversation they know they need to have, and the conversation drifts for weeks or months while the cost compounds.

So I built an AI skill. A small, focused tool that takes a manager who is stuck and walks them through structured prep for the conversation they have been avoiding. Outcome they want. Simple true thing to say. What they are afraid of. What it costs if they do not have it. The same framework I have been teaching one manager at a time for years, now available in five minutes on a Tuesday afternoon.

I expected it to be useful. I did not expect what it would teach me about the work.

What the AI revealed

When you build a tool to do something humans usually do badly, you have to get very specific about what "doing it well" actually means. Vague gets exposed. Filler gets exposed. The places where I had been letting my own intuition cover for fuzzy thinking got exposed.

The first thing the AI made obvious is how much of the framework I teach is actually about emotion management, not strategy. The "what are you afraid of" question is not really a strategy question. It is a way of pulling the manager's emotional state into the open so it stops driving the conversation invisibly. Once you have to encode that in software, you realize how much of expert coaching is just creating space for someone to admit something they were hiding from themselves.

The second thing it revealed is how often managers describe a "performance problem" that is actually something else. When the AI asks "what specifically has this person done or not done that you want to address," a meaningful percentage of the time the manager realizes they cannot answer. They have a feeling. They have a frustration. They do not have a specific behavior. That is not a performance conversation. That is a manager who has not done the diagnostic work yet.

The third thing, and this is the one that still surprises me, is how often the AI catches the manager themselves in avoidance. Someone will start prepping for a conversation about a direct report and, partway through, realize they have been documenting the issue for six months without ever once raising it directly with the person. The tool was not designed to catch that. But the structure of the prep forces the question: have you actually told this person what you are seeing? And the honest answer is often no.

The thing I did not expect

The AI caught me too. Twice.

Once when I was prepping to give difficult feedback to a contractor I had been working with. I ran my own draft through the tool. The "what are you afraid of" question stopped me cold. I was afraid she would feel hurt. I was afraid I would lose someone I liked working with. I had been softening my feedback for weeks because of those two fears and pretending I was being thoughtful.

Once when I was about to skip a hard conversation entirely because "it would resolve itself." The cost-of-not-having-it question forced me to actually think it through. It would not have resolved itself. It would have gotten worse.

I have been teaching this material for years. I still got caught by my own tool. That is what convinced me this is not just a coaching aid. It is a structural correction to a thing humans are biologically wired to do badly: avoid short-term discomfort at the cost of much larger long-term pain.

What this means for HR and people leaders

I think we are at the start of a real shift in what HR work can look like.

For most of my career, the expertise I built up was bottlenecked by my own calendar. I could coach one manager at a time. I could deliver one training to one room. The deep, judgment-based work of helping leaders through hard moments has always been one-to-one because there was no other way to do it.

That is not true anymore. The combination of large language models and well-designed prompts means that experienced HR practitioners can now externalize a portion of our judgment into tools that scale. Not the whole job. Not the parts that require relationship and reading the room and knowing when to push and when to wait. But meaningful slices of it, especially the prep and structure work that most managers skip because there is nobody available to walk them through it at 9pm the night before the meeting.

This is not the AI-replaces-HR story. I am not interested in that story and I do not think it is true. The relationship and judgment work is going to stay deeply human. But the part of my job that is essentially a structured framework I am walking someone through? That part is becoming software, and the people who build it will be the ones who actually understand the underlying work.

That is the bet I am making. That the next generation of HR consultants and people leaders will not just deliver expertise. They will build it.

What I am working on next

I’ve created The Performance Play- a small library of AI skills aimed at the specific moments managers and HR partners get stuck. The hard-conversation prep tool is the first one. Next is a tool for catching manager avoidance before it turns into a six-month documentation cycle. A realtime reaction handler, skill vs will identifier, PIP builder and termination conversations builder round out the bunch.

The goal is not to replace the conversation I would have with a client. The goal is to make that conversation more useful when we do have it, because the manager has already done the structural work and we can focus on the parts that require real judgment.

If you are an HR consultant, a People leader, or a founder running people operations without a head of HR, I would love to hear what gets you stuck most often.

Performance problems do not come from bad people. They come from unclear systems. And it turns out, the same is true of avoidance.

Want early access to the skills I am building? Reach out or book a 30-minute consultation. I am sharing them with a small group of HR leaders and founders first.