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Five Tips to Improve Your Coaching Conversations

As a leader, you're responsible for coaching and growing your team, helping them be successful. To do this, you need to set the tone and example of the behaviors you want the team to have.

No matter how good of a team you have or how good of a leader you are, you will have to have a conversation about performance. Whether it's delivery, professional skills, or technology skills, you will have a moment where you need someone to change their behaviors.

Having these types of conversations can be scary, no matter how much experience in leadership you might have. However, when done correctly, these moments can greatly impact the other person, helping them grow tremendously.

On the other hand, poor coaching will do the absolute opposite. The other person can become confused or angry. They could even shut down and disengage altogether, making coaching them that much harder.

So what does good coaching look like? I can't guarantee that these steps will solve all your woes; however, I do guarantee that following these tips will increase the odds of the other person listening and at least consider your feedback. Remember, you want to do this coaching because some behavior has caught your attention, and you want to correct it. If the other person doesn't listen or want to engage, then you literally can't make this happen.

Step 1: Be Timely

The sooner you can have this conversation, the more effective it will be. Remember, the point of feedback is to let the other person know how they're doing and correct if needed. They can't do this if the behavior happened three weeks ago because there's no correlation at that point.

Imagine if you had a test suite that only told you about failing tests a week after the build started. There's no way you could make the right decisions, so why would we think that's the case for behavior?

If I've noticed a pattern and feel that it's time to coach, I will get that feedback to them that week, if not the next day.

Step 2: Be Specific

When giving this feedback, the behavior may be obvious to you but not even a thought for the other person. Because we can't control what the other person is thinking, we need to set the context for the feedback so they know what you're talking about.

Let's take my son, for example. He's particular about his food, so when he says that "dinner was awesome," that makes me feel great as I'm happy he enjoyed dinner. But I have no clue what he actually liked or why he thought that. Was it the food? The way it was served? The fact that we had a picnic? No idea, so I'd respond with, "What made it stand out to you?". When he mentions that he liked the pizza, I go "Ah! He enjoyed the food, nice!"

Providing this specific context is crucial for the other person because it lets them kow what caught your attention and drastically reduces the confusion in the conversation. For those who like more concrete details, sharing links to chats, emails, or other artifacts with the behavior can be helpful because you can use it as the foundation for the conversation.

Step 3: Explain Why

There's a reason that you're having this conversation. There's something that's important to you, and, in your opinion, it wasn't important to the other person. We've got to explain why it's important and why you're commenting on it.

I never want to remove someone's autonomy as I like to set the direction and let the team blaze a path, with me guiding to make sure we don't get lost in the wilderness. However, for someone to have autonomy, they need to understand the goals and the reasoning behind it.

If they don't have this knowledge, then it's that much harder for them to make the right decisions. Ensuring they know the why is a leader's responsibility.

Step 4: Seek To Understand

You're working with a team of professionals. A professional makes the right decisions based on their knowledge and experience. If the person is making mistakes, we need to understand why they made the choice that they did.

For example, let's say I'm coaching someone who's consistently missing meetings. I'm frustrated that they're unresponsive and that they don't care. The issue here is that it's okay for me to feel frustrated, but I can't make the judgment that they don't care. I don't know that, and it causes more problems than it solves. I won't vent my feelings to the other person because even though it'd make me feel better, it doesn't help the situation.

A better approach would be to understand why they're missing meetings. Is it something outside of work? Could it be that they don't know why they need to attend? What if they didn't receive an invite? In any of the above cases, there was a solid reason why they didn't attend, and I wouldn't have known that if I had not opened the conversation.

Don't assume malice or apathy when something happens. We are humans first, which means we're going to make mistakes.

Step 5: Working Together

The entire point of coaching is to help the person improve, and we also don't want to take away their autonomy. To make this happen, we need to work with the other person to come up with ideas that can help improve the situation. It's not any one person's responsibility, but it's your responsibility to brainstorm with them and help guide them down the correct path.

The key here is to have an open mind and really consider all ideas. One of my favorite leadership books, First, Break All The Rules, talks about how great leaders work with their people to have their strengths shine and to make their weaknesses a non-issue.

In the missing meeting example, I found out that the issue was that they didn't know why they needed to attend the meeting, so they didn't attend, in order to focus on their development work. Working together, I changed invites to include the reason for attending and encouraged them to chat with me so we could figure it out if they didn't know why they needed to be there.

Case Study - Bringing It Together

In this example, let's explore where we would need to do some coaching.

While reviewing a pull request from Bruce, you see a comment from Alvin, a member of your team, where they were particularly critical of the work. Reading through the pull request, you see Alvin has left more harsh comments about Bruce's work.

Talking with Bruce, they mention that they don't work well with Alvin as it seems like he's always critical of Bruce.

Based on this scenario, we know that Alvin has left some harsh words for Bruce, which makes them less likely to work together. If Alvin keeps this behavior up with other people, this will impact others wanting to work with him, reducing his effectiveness.

After collecting your thoughts, you reach out to Alvin to see if he's got a few minutes to chat about Bruce's pull request.

"Hey Alvin, I noticed you left some pretty harsh comments that in Bruce's pull request. For example, saying that 'this code is convoluted, rewrite it'. Even if that was the case, it's not clear why you think that. I'm more concerned with how the messaging came across because we work with others to accomplish our tasks, and that communication style can make people not want to work with us.

I don't believe you intend to alienate others, so can you walk me through your thought process here and why you thought this was the right approach?"

In this example, we've already hit four out of the five tips. Our feedback was timely and specific to the problem. We included why it caught our attention and started with an open-ended question for the conversation about the behavior.

In the follow-up conversation, Alvin mentions that he was having a rough day, particularly outside of work, and that he wasn't entirely focused on his tone. Given that this is the first time Alvin has done this, we want to focus on fixing the issue before it becomes a pattern.

"I understand that it can be hard to focus on your tone when you're having a rough time, however, we can't speak to others this way. I don't want this to become a pattern, so what are some things that we could do instead when we're not in the right mental head space for code reviews?"

At this point, we've acknowledged what was said and reaffirmed expectations. Using another open-ended question, we can start brainstorming things that we could do to help improve Alvin's tone. Since we're opening the conversation, Alvin is also giving feedback on what might work for him and what wouldn't work.

Wrapping Up

Giving critical feedback to someone is not the easiest thing to do, however, it can have the most impact for them. To help frame the conversation, our coaching should:

  • Be Timely
  • Be Specific
  • Explain the Why
  • Seeking to Understand
  • Be Collaborative