[Issue #044] I Want You To Be Brave

Over the last couple of weeks, I’ve found myself saying the same thing to several leaders I coach:

“I want you to be brave.”

We weren’t talking about making a big investment or launching something new. We were talking about having a conversation.

A conversation with someone they lead, work with, or partner with. Something wasn’t working, and they knew they needed to address it. But the thought of actually bringing it up was uncomfortable.

You could see it in their eyes. They understood why it mattered. They wanted things to get better. They were also processing what might happen once they opened their mouths.

Maybe you know that feeling.

You’re worried they won’t like you. You’re worried they’ll quit. Or you’re worried they’ll say, “Well, I’m not going to change,” and then you’ll have to figure out what to do next.

So you tell yourself it isn’t that big a deal. You can work around it. Maybe it’ll get better.

Sometimes we can get pretty creative when we’re looking for reasons to postpone a conversation.

The trouble is, while we’re postponing it, the problem keeps going. We carry the frustration. Other people pick up the slack. And the person who needs to improve may not even understand what’s wrong.

We want to be good bosses. We care about people. But caring about someone also means being willing to tell them something they need to hear.

That takes courage.

Before you have that conversation, though, there are three things I want you to check. They’ll help you understand what actually needs to be addressed, and whether part of the solution begins with you.

1. Have you made success clear?

It’s amazing how often accountability gets difficult because we haven’t clearly defined what we’re holding someone accountable to.

We say, “I need you to be friendlier with customers.”

That sounds clear enough. Until you realize that what you mean by “friendly” and what they mean by “friendly” might be two different things.

You’re picturing someone looking up when a customer walks in, smiling, saying hello, and asking how they can help.

Your employee is thinking, “I answered their question. I wasn’t rude. What’s the problem?”

Before you assume they’re ignoring your expectations, ask yourself: Have I actually explained them?

You can begin with a question:

“When someone walks into our office, what do you think a good greeting would look like?”

Listen to the answer. You might discover that they understood something different from what you intended.

If that’s the case, own your part.

“I can see how you got there. I haven’t made this clear enough. Here’s what I need you to do going forward.”

Then describe something specific enough that both of you can recognize whether it’s happening. You can even have them demonstrate it so you know you’re picturing the same thing.

This applies well beyond greeting customers. It applies to deadlines, project updates, quality standards, and what decisions someone should make without checking with you.

Your frustration may be telling you that someone needs correction. It may also be telling you that you need to bring more clarity.

Before you walk into the conversation, know which one you’re dealing with.

2. Do they have what they need to succeed?

Once the expectation is clear, the next question is whether the person can actually meet your expectations under the conditions of the job.

Do they have the skills? The understanding? The judgment? Enough time? The right resources?

Someone might know how to complete a task when they can focus on it, but struggle when they’re juggling competing priorities and getting interrupted all day.

Someone else might be ready to make routine decisions but still need help working through unfamiliar situations.

Those differences matter.

If we treat every performance problem as a lack of effort, we can end up telling someone to try harder when what they need is training, clearer priorities, or help making a decision. (if they need help making a decision see the magic of a 1:3:1 that I wrote about in TLC #040)

“I need you to do better” doesn’t give them much to work with.

Instead, ask:

“What’s getting in the way of doing this consistently?”

Then listen long enough to learn something.

You may discover a misunderstanding you can clear up, a skill you can help them develop, or a workload that needs adjusting. You may also discover that the demands of the position aren’t a good fit for the person.

And yes, sometimes you’ll find that someone understands the expectation, can meet it, and isn’t following through. That needs to be addressed directly (and not in a text).

But you’ll have a much more useful conversation if you’ve taken the time to understand the problem first.

3. Are you coaching them before problems pile up?

Some leaders only sit down for an intentional conversation with an employee when something’s gone wrong.

The rest of the time, they’re talking more informally throughout the day. They discuss projects, answer questions, and solve whatever needs attention but in a more casual way.

Then they say, “Hey, can we talk?” and the employee immediately wonders what they did wrong.

You can understand why.

Regular coaching conversations give you a chance to talk about what’s working, where someone is getting stuck, and what they need to focus on next.

They also let you catch misunderstandings while they’re still small.

You don’t need to turn every meeting into a major event but you do need to make time to pay closer attention.

You might say:

“Here’s what we agreed success would look like, and here’s what I’m seeing. How are you seeing it? What’s getting in the way?”

From there, work toward a clear agreement about what needs to happen next, what support you’ll provide, and when you’ll check back.

That last part matters. A good conversation can feel productive in the moment and still change very little if nobody leaves knowing what happens next.

These meetings take intentionality. When everyone’s busy, it’s easy to keep moving and assume things are fine.

But those smaller coaching conversations can help prevent that awkward moment three months later where you show up with a list of frustrations and the employee is hearing them for the first time.

As you’ve been reading, you may have thought of a conversation you’ve been putting off. One that you really need to have.

Before another week slips by, take a few minutes and ask yourself:

Have I made success clear? Does this person have what they need to succeed? Have I been coaching them along the way?

If you’ve missed something, that gives you a place to begin.

And if you’ve done those things and the problem continues, it may be time to address it in a more serious tone..

You can care about the person and be clear about what needs to change. You can listen to their perspective and still hold the expectation.

You may feel uncomfortable doing it. Courage means being willing to act while that discomfort is still there. Just remember that the goal is to walk away from the conversation with a win for both of you.

I want you to be brave.

Think of the conversation. Prepare for it. Put it on the calendar.

Until next time,

Keep learning.
Keep growing.
And God bless,

Michael

Half a Bubble Out (HaBO)
Business Consulting | Leadership Coaching