By Lyssa deHart and Jake Mannino
Published on June 30, 2026
There's a tension most leaders who are also trained as coaches eventually come up against, and it doesn't get talked about enough.
You've been trained to be curious, to ask open-ended questions, and be empathetic. And then you've got someone on your team who's leaving little piles of — let's just say — wreckage everywhere they go. And, often, they think everything is fine, they're hitting it out of the park. But, you're getting calls.
So what do you do?
You can't coach someone into competence they don't have yet. And you can't keep asking open-ended questions to someone who doesn't have insight, understand the expectations, or who keeps making the same mistake over and again, after you've already had a, or a few, conversations about it. At some point, the conversation is going to require more.
And, how you do that matters. A lot.
First — know who you're actually dealing with
Not everyone who's struggling is struggling for the same reason. There's a framework I heard years ago, a General was talking at a Military dinner, and it's perfect. He said, "there are four kinds of people:
Smart and lazy. They've got the ability, they're just not using it. Sad waste, but they're not causing active harm.
Smart and industrious. Everyone wants these people. They're doing the work and doing it well.
Not smart and lazy. You know what you've got. Nothing great happens, but nothing catastrophic happens either.
And then — and this is the one that creates a lot of sleepless nights — not smart and industrious. That's a tough one. You've probably seen this a few times in your life; they are high activity and consistently have bad outcomes. They're doing a lot, and most of it is not good.
Now, think which type of person is this one on your team? Because this changes lots about the conversation you need to be having, and the sorts of decisions you need to be noodling through.
Maybe they need more training. Maybe they're a genuinely good person who's in the wrong seat. Maybe they've made one mistake and need awareness. Or maybe this is a pattern and you need to be considering a full exit stage left — and that's a different conversation entirely.
One mistake versus a pattern
Here's the thing, mistakes happen. And, sometimes a mistake is a mistake. If we are in a small tribe of people, (i.e. a team) and someone brings back poisonous berries once — okay, you make sure they have the training they need to pick the good berries, you retrain them. You want to make sure they know what they're looking for. You give them another shot, but you also make sure to watch what berries they are bringing back to the tribe.
But if they bring back poisonous berries again, or maybe they keep making this mistake? That's a pattern. And the pattern doesn't just affect that one person — it affects the whole tribe. The rest of the team is watching. They're asking themselves why this keeps happening, why is this one person allowed to spend time picking berries and then bringing back the wrong ones, they are definitely losing trust in the bad berry picker. But honestly, they're watching you to see if you'll address it, and if your pattern is to keep sending the berry picker out to do it wrong, they are losing trust in you as well.
In a coaching conversation once, a client shared something their grand-dad said, If you are heading in the wrong direction, stop walking. It applies here too—if you're picking poisonous berries, stop picking.
Not addressing a problem on a team is its own message, it's not a good one, and people listen closely for this sort of message.
Before you have the conversation — regulate yourself first
This part doesn't show up enough in leadership books, and it should.
When a customer calls you and says your employee really messed up — again — you're going to feel something. Anger. Frustration. Maybe some anxiety about the conversation you now have to have. That's human and the feelings are real.
But you can't walk into a feedback conversation still running on that energy, you're going to need to get yourself regulated first. Process the emotion, get to the facts, before you reach out.
And then — this is equally important — give them time to regulate, too. Timing matters crucially in complicated or problematic conversations.
"We need to talk." Those words. Nobody hears those, and says to themselves, "This is going to be great!" "I'm probably getting a promotion!" Instead, like the Bat Mobile, our defenses go up immediately, and you haven't even started having the conversation yet.
Instead: Hey, I got some feedback from a customer that I need to share with you and discuss. Can we meet at 2pm? That's probably enough. You've flagged something is coming. You've given them context. You've given them time to downshift before they walk into the room. If they need more information, you can decide if you want to risk the conversation on the fly, or if you want to control the speed of the conversation. They were unhappy with xyz, we can discuss it further at 2pm. A lot of people allow the conversation to control them, but you can control the conversation with your timing, your tone, and your goal for the outcome.
Personally, two hours is probably a minimum amount of time. If you can, within 24 hours is good. Most people don't think fast enough to sort through something hard on the spot, and if they're going to blow up, it's usually because they haven't had time to even figure out what they're feeling yet and they get defensive. Given a bit of time, they can move through the instant anger or concern and get to a mindset that, fingers crossed, is more useful.
In the conversation itself
Go in with a clear goal of what you want. What are you actually there to accomplish, what do you hope for the conversation?
If it's a first offense — awareness and a change in behavior- we need to discuss the berries you picked; those are poisonous, and the ones you are looking for look like this. Do you see the difference? Good, then pick more of this type, not that one. That's it. You want them to understand what happened, understand the expectations, and leave with a concrete path forward.
If it's a pattern that keeps rewinding and playing over and over — you might be there for something a bit more uncomfortable. To assess whether this is even the right role. To figure out whether you're helping them correct course or helping them find a better seat somewhere else.
Know the difference before you walk in.
And when you're in the conversation, be specific. Not "you need to do better." That means nothing. What specific behavior, in what specific situation, created what specific problem? This is what the customer said. These are the words. And, keep it clear about a behavior, not about them as a person. Most people don't intend to say something problematic or do something problematic. Intent is important, but impact matters equally, if not more.
Two or three examples is enough. You don't need twelve. One clear, specific thing is often all it takes for someone to actually hear you. Especially if you stay calm and focused on your goal for the conversation.
Working with a leader who came to a session worried about a conversation about a direct report not getting the quarterly bonus- He's the pushback guy; the conversation is going to be horrible. What is your goal for this conversation? I want him to get bonuses. I want him to be successful. But, he didn't do the things we discussed in December that needed to be accomplished for his end of quarter goals. What changes if you go in with your goal of wanting him to be successful versus going in defensive of potential pushback?
It's an interesting question. In this situation the leader shifted his energy, went in with the energy of an ally. He ended up having several conversations with his direct report, but it never went sideways. They got clarity about the expectations and wrote up the new goals. The leader was able to stay in the role of, help me help you.
The goal isn't to feel good — but it should be honest
Sometimes both people leave hard conversations feeling deflated. That's okay, you can acknowledge it going in: this might be a tough conversation, and we might both leave here not feeling great about it, but I want us to work together to sort out how to resolve this situation. That's not being weak — that's honest, and also primes both of you toward working to a resolution. This sort of candor can actually lower both of your temperatures before you even start.
What you're really going for is clarity, alignment and a shared understanding of what happened, what's expected going forward, and what an action plan looks like — it's ideal when you can build this together.
And document it. Not just to cover yourself legally, though yes, that too. But because without documentation, the conversation might as well not have happened. There's no record, the behavior continues, and eventually you're managing something that could have been addressed months ago. You're also not doing any favors to your team, yourself, or your organization. How many of us have seen bad behavior from someone, and they still get promotions and move to different teams, taking that bad behavior with them.
For coaches working with leaders in this situation
If a leader comes to you needing to discuss this — the sleepless nights, the frustration, the "I don't know how to handle this" — your job isn't to tell them what to do. But instead, support them to get clear on these elements, so they can sleep and then have a conversation.
What is their goal for this conversation? Who is this person, actually — do they need more training, are they in the wrong role, or is there a pattern here that's affecting the whole team? How are you doing, emotionally, mentally, physically going into this conversation — are you regulated enough to be useful? And have you thought about how to give this person a heads up, versus blindsiding them?
Those questions alone can illuminate a lot.
Because here's the thing — not many people enjoy hard conversations. We don't like bringing them up, we don't like having them. And most leaders would like to avoid the hard conversation because they are people, like everyone else. Not because they're bad leaders, but because it's genuinely not a lot of fun. It takes something, courage, hutzpah, grit to sit across from someone and say: what you're doing isn't working, and I need it to change.
But avoiding it doesn't make the problem smaller. It just makes the eventual conversation harder. And in the meantime… The rest of the team is watching.
By Lyssa deHart, LICSW, MCC, BCC and Jake Mannino PCC, MBA for NEXGEN Executive Coaching Academy
NEXGEN Executive Coaching Academy was founded in 2026 by Lyssa deHart (LICSW, MCC) and Jake Mannino (MBA, PCC) to address a specific gap in the professional coaching education market: the absence of programs that combine ICF-credentialed coach training with practical business-building skills.
According to the World Economic Forum, over 85 million jobs may be displaced by automation by 2025 — accelerating demand for human-centered skills like executive coaching.
NEXGEN's programs are designed specifically for accomplished working professionals who want to become credentialed ICF executive coaches and build sustainable coaching businesses — without leaving their current careers to do it.
Disclaimer: This article was originally published on LinkedIn on June 30, 2026.
Original LinkedIn article: https://www.linkedin.com/pulse/you-cant-coach-what-dont-know-theyre-8thvc/?trackingId=G2y8OBlAkXFWYakXp1DgQQ%3D%3D
