The first step is knowing that your team member is stuck. The second is deciding what to do about it. The good news is that there are plenty of ways you could respond. You could tell them to just get it done. You could feel frustrated that it’s still not finished. You could take it off their plate completely. None of those are great options.

The first is nagging. The second is just frustration - yours, not theirs. The third creates dependency and, depending on what it is, can actually make things worse - for them, for the relationship and for how they're perceived.

So what does good coaching actually look like when someone is stuck? This week's video walks through a a real example - a roleplay of a manager coaching a team member who's dreading telling a client that they won't hit a deadline. Watch and read below for practical tips.

Pause and Consider What's Really Going On

Before you tell them what to do, it's worth asking: exactly what is making this hard for them?

Avoidance usually isn't laziness. It's almost always discomfort - fear of the reaction, uncertainty about what to say, or a sense that doing nothing is safer than doing something wrong. In this week's video, where the team member needs to tell a client that a product deadline is going to be missed, they know they need to. They just haven't.

That's not necessarily a performance problem - it's a coaching opportunity.

The most useful thing you can do is help them think through it - not do it for them.

Act: How to Coach Someone Through What They're Avoiding

Start by talking about it without judgment. In the roleplay, I (as the manager) open with: "I know each of us has things we put off. Sometimes you can make yourself do it. Other times it helps to have someone sit with you and talk through it." That's it. It's not a lecture or pressure, but a reminder that this happens to all of us.

Help them see it from the other person's perspective. One of the most powerful things a manager can do is help someone get out of their own head. Ask: if you were on the other side of this, what would you want? What would it feel like if the situation were reversed and you heard nothing? That shift in perspective often does more than any script.

Work through the "how" together - don't just hand them a solution. Giving someone a script can feel easier (and be what your team member hopes you'll give them), but it isn't coaching. Walking through the conversation with them, including what could happen, and then figuring out what they actually have authority to offer - that's coaching. There's a big difference between "here's what to say" and "let's think through this together."

Let them own it. The instinct when a team member is struggling is to step in and take it over. And sometimes that's right. But for conversations that belong to them - a client they manage, a conflict they're in the middle of - stepping in on their behalf often signals to everyone involved that something's more wrong than it is, and that they can't handle it. Instead, help them get ready. Then let them go do it. You can always be there if needed.

Do a quick gut check on what's needed before the conversation happens. Especially when bad news is involved: do they know what they can realistically promise? Do they know what concessions they can offer? Have they thought about what the goal is and what steps could best help get there? Five minutes of prep can be the difference between a shaky call and a confident one.

Takeaways as a Leader

The goal of coaching a team member through something they're avoiding isn't to make it easy. It's to make it doable - and to help them build the confidence to handle it themselves next time.

When you meet with your team member and work through the thing they've been dreading, you're not just solving a one-time problem. You're teaching them a framework for how to handle discomfort. That's the kind of manager people remember - and appreciate for their entire career.

And while you may already know this, your team member might not - those tough conversations often go better than expected. But instead of just telling them that, you helped make it happen.

Managing a team and looking for practical tools for exactly these moments? Our course Manager 101 is built for the real situations managers face - not just theory.

In HR and seeing the need for effective leadership development across your organization? We help organizations build this kind of coaching culture at scale. Reach out here.