Stop Endlessly Coaching Your Team

Your job as a leader is to help others to become leaders themselves.

In my experience as an executive coach working with leaders from all over the world, 90% of your on-the-ground leadership happens inside of conversations.

You set goals, people go to work, and stuff goes wrong. Sometimes you correct a problem one time and that’s it. The team gets it and they fix the problem for good.

Sometimes the problem keeps happening. When it does, it DRIVES YOU CRAZY!!! There’s new problems all the time, so the old problems that stick around can be infuriating.

Most of the time, as a leader, you do a crappy job at these conversations, partially because of frustration and partially because you’ve never really practiced them.

So I’m going to break down step by step the exact process I’ve taught people to use when they talk to their distracted co-founder, their smart but underperforming coder, and even their kind but fumbling assistant.

Not only will this framework help you be more calm, but it will greatly increase the likelihood of not having to have as many of the same conversations over and over again.

You are going to need to start by learning how to talk to people.

How to Prepare for a Why Does This Keep Happening Conversation

You’re likely going to have your own thoughts and feelings about an issue or person before you talk to them. As a leader, it’s important that you address and put aside your personal feelings before entering into a conversation so that you can successfully hear the other person and move forward together. Do the following to get yourself clear and prepared:

1. Let go of being right – If you’re a human being, you are probably pretty sure you’re right about what’s wrong and how to fix it. Especially if there are issues with the other person. The team member may be lazy, inattentive, out of integrity, or at least some version of hopeless. I know you want to be right about them and that’s OK. In order to prepare, you need to start by trying to let that go. Assume that you don’t have all the information and don’t know exactly what’s going on. Then, assume you are at least as responsible, if not more than they are. If you struggle with this, make sure you do the next step.

2. Process your emotions – There are bunches of ways to do this. You can write things out, bang on pillows, or you can simply have a venting session. The idea is that you express or write down ALL of the thoughts, feelings, and bodily sensations that come up when you think about this person or situation. Get them all out without filtering, in a safe place. Write an angry email (don’t address it or send it) or talk to a trusted advisor. Coaches are especially helpful for something like this.

3. Just the facts, ma’am – Once you get the feelings out, next write down just the facts of the situation. Like the things a camera could record. Word for word what they said. Moment by moment what happened. Try to notice any judgments or assessments. Descriptors like slow, dumb, incompetent, and late are all assessments/judgments. Try to be as clean as possible. If you notice more feelings come up, go back to Step 2 and get them out. That’s OK to do.

4. Get clear on your side – Try to look at what you could have done differently and what you can be responsible for. If it was 100% on you, why might that be the case? It’s probably not all your fault, but it probably isn’t 100% theirs either. Your ability to point to your mistakes will open up a safe space to admit common problems. Remember, taking responsibility is part of your job as a leader.

How to Structure Coaching Conversations

Once you’ve prepared and are clear on your end, you’re ready to actually talk to the other person. Here is a framework for the conversation that will help you to sit down with them most effectively and move in a direction you both want to go. These steps are best done in order. No matter how much you want to get your perspective across first, I’ll urge you to listen before sharing. (Note: This sample conversation comes after previous conversations addressing the same problem. Don’t get hung up on that. The structure can be used at any time.)

1. Set the context – Be simple, direct, and state the outcome you want. Get on their side and look at the problem together.

  • “Hey I wanted to talk with you. I notice that we keep having the same problem crop up again and again. I don’t really want that to keep happening and I imagine you might also feel like I’m nagging you. I want to talk about it so we can see what the breakdown is and find a way forward.”

2. Identify the problem – Refer back to the ‘just the facts’ process. Explain what you understand is happening. Take time to pause and see if you missed anything.

  • “So here’s what I’m noticing. When I ask you about the sales numbers you express enthusiasm and yet we have missed our target 5 times in the last 90 days. I just want to check in. Do I have that right? Was I unclear on the targets at any point? Or are we on the same page that the targets were clear and we haven’t been hitting them?”

  • “I also want to be clear that we’ve talked about this 3 times. I’m sure I could have been better in those conversations but I just want to make sure that I’m not confused that we’ve tried to address this in the past.”

3. Find out what’s missing for them – Get their take on why this keeps happening, listen to their experience, reflect what they say, and acknowledge that it makes sense. Do this even if it doesn’t make sense from your perspective. Try to get into the world view from which it does make sense.

  • “So I want to understand here. It sounds like sometimes you feel the targets are unrealistic and that I haven’t heard you when you’ve said that. Do I have that right? Ok, yeah I get that, that makes sense. It’s a hard conversation to have when we feel targets are off. I get that.”

4. Share your experience – After checking in with them, share your experience and take responsibility for your part in it. Refer back to your responsibility list or anything the team member brought up. Be honest. Be vulnerable. Don’t be a jerk. Share your feelings without putting blame on them.

  • “Are you open to hearing my experience? Great. Well, I struggle to know how to talk to you about this. You’re always so optimistic, which I really love, but it feels like we’re not on the same page about the numbers. I find myself often feeling wary before we talk and frustrated afterwards. I can see now that I haven’t taken the time to make sure you get why the numbers are what they are. I’ve also hid my frustration, which isn’t really fair to either of us. I’m sorry about those things. And I want to be able to have frank discussions about our numbers with you.”

5. Discover solutions together – After getting their buy-in, look at the problem together and come up with possible solutions or ways forward.

  • “Ok, how might we move forward in a better way? I really want our relationship to work and having the same conversation, again and again isn’t much fun for either of us. What solutions do you think we could employ?”

  • “Great, I think a mid-week check-in is a great idea. That way we can get ahead of the numbers before we’re too far behind.”

  • “I’d also like to create a set structure for how we deal with not hitting the numbers. I’d like to look at the numbers on Friday and then go through a few questions like, what impacted your numbers this week? What isn’t working? What can we try to improve things?”

6. Create agreement, recap, and acknowledge – Finally, once you’ve got some concrete steps, agree to what you’re going to work on and when, recap the discussion, and acknowledge them. Don’t skip the last part. Show them you appreciate who they are for the company and that you have their back (so long as you actually do).

  • “Great, so we’re going to do these two meetings and the questions I recommended and we’re going to start next week. Are you still a yes to those two? Great!”

  • “It also sounds like we were missing each other when we talked. You secretly thought the targets were unrealistic and I wasn’t being honest about my frustration. We each saw what was missing and we’ve come to some agreement on how to move forward.”

  • I just want to close by thanking you for your candor. I know these conversations can be tough and I appreciate you being so honest with me.”

7. Follow up and inspect what you expect – Once the conversation is over, follow up with a brief write-up and, most importantly, DO WHAT YOU SAID YOU’D DO. If you want to not have the conversation again, stick to your commitments and check-in that they hold up their end too.


That’s it. Simple and direct. If you begin to prepare yourself for conversations with your team — especially conversations that have you emotionally charged — and take time to set context, listen, find what’s missing, and discover solutions together, you’ll start seeing incredible progress from your people. It’s a practice you can start today.