Coaching Conversation

If you think about them as difficult conversations, you’ve just told your brain they will be. So reframe your thinking.

Start by thinking of it as an honest conversation. A direct conversation.

Better yet, think of it that will help the feedback recipient build their skills, ultimately grow their careers, and achieve your organization’s and your clients’ highest standards.

First Things First

Start by preparing thoroughly. Have a plan to lead with curiosity instead of judgment, and to focus on future performance rather than past failures. Decide to have a conversation that’s kind, but not necessarily “nice,” because those are different.

And here’s what I know after coaching agency leaders through hundreds of these conversations: the difficulty isn’t in the technique, it’s in your own resistance to having the conversation in the first place.

Let me be direct: most leaders I work with wait too long. They hope the problem will fix itself. They drop hints. They adjust workloads to compensate. And meanwhile, the underperforming employee doesn’t know there’s a problem, the rest of the team is getting frustrated, and the leader is building resentment.

Sound familiar?

Why These Conversations Feel So Hard

Here’s the thing: if you dread performance conversations, you’re not a poor leader. You’re human. Most of us became leaders because we ‘re good at our craft, and then got promoted into management, and then leadership.

But along the way were we trained or coached into how to give this feedback? Probably not. And in agency life, where relationships matter and we’re all under pressure together, it can feel especially hard to risk the connection.

But avoiding the conversation isn’t neutral. It’s a choice, and it has consequences. For the employee who might actually want to improve if they knew what was expected. For the high performers who are picking up the slack. And for you, because that avoiding-the-conversation energy drains you more than having the conversation would.

How to Prepare for the Conversation

Check your own energy going into this. (As an Energy Leadership Index Master Practitioner, this is where I focus a lot of my coaching work.) Are you going in feeling angry, disappointed, or frustrated? Those energy states are contagious and will shape the conversation. See if you can shift to curiosity: “I wonder what’s getting in their way” instead of “Why can’t they just do their job?”

Get clear on the specific behaviors and impacts. “You need to perform better” isn’t feedback, it’s frustration. Instead: “In the past three client meetings, you’ve arrived 10-15 minutes late, and the client mentioned it to me.” Specifics give people something to work with.

Know what outcome you’re aiming for. Is this a “here’s what needs to change” conversation, or a “we need to talk about whether this role is the right fit” conversation? Don’t surprise someone with a termination conversation they thought was going to be coaching.

The Conversation Itself

Start with direct context. Not small talk, not the “compliment sandwich.” Just: “I wanted to talk with you about your performance on the X account. I’ve noticed some concerns, and I want to understand what’s happening from your perspective.”

Ask before you tell. This is the part most leaders skip. “What’s your sense of how things are going with the X account?” You might learn something that completely reframes the situation. Maybe they’re unaware that they’re under-performing, or in denial about their performance, or struggling with something with which you can actually help.

Be specific about what needs to change. “I need you to hit your deadlines” is vague. “Going forward, I need first drafts delivered by Thursday at 5pm so the team has Friday to review before client presentations on Monday” is clear.

Get agreement on next steps. Don’t end the conversation without clarity on what happens next and how they’ll report progress to you. And don’t bother asking “Do you understand?”, because the answer will always be “Yes!”.  Don’t even ask “So we’re aligned that you’ll do X by Y date, and we’ll meet again on Z to review progress?” because the answer will always be “Yes!”

Instead, use questions to determine if they understand precisely what’s expected of them. Don’t fill in the gaps. Some silence indicates that their brain is working.

Once they answer, if you’re satisfied with it, ask them 1) How they’ll hold themselves accountable; 2) How they’ll report progress along the way; and 3) What they need from  you to succeed.

That last part is absolutely essential, because it signals your belief that they can improve to the level required, and that you’re there to help them get there.

And there’s nothing more inspiring than a leader who believes we can hit the heights.

What to Do If They Push Back

Some employees will get defensive. Some will cry. Some will make excuses. All of that is normal, and none of it means you did something wrong.

Your job isn’t to make them feel good about the feedback. Your job is to be clear, fair, and focused on their success. You can acknowledge emotion without backing off the substance: “I can see this is hard to hear. And these are the standards for this role. And I believe you can get there”

The Follow-Through Matters More Than the Conversation

Here’s where a lot of leaders fail: they have the hard conversation, feel relieved it’s over, and there’s no follow up.

To be clear, following-up doesn’t mean sending an email or a Slack message or a call about progress. I use the term follow-up to mean a brief meeting to check in on improvement and progress.

Set a specific check-in date, or, if needed, check-in dates. Review progress honestly. If things improve, acknowledge it. Make a big deal about everything they got right. This isn’t coddling: It’s encouraging more of the work improvement or desired behavioral change.

If they didn’t meet the standards, give more direct feedback on what must be done by the next check-in or deadline. This isn’t about being punitive, it’s about being consistent.

When It’s Time to Part Ways

Sometimes, despite the employees’ best efforts, these conversation don’t lead to improvement. And that’s okay. Not every role is right for every person. If you’ve been clear about expectations, given them a genuine chance to improve, and it’s still not working, the kindest thing you can do is help them transition out.

I’ve coached many leaders through terminations, and what I tell them is this: clarity is kindness. Letting someone languish in a role they’re not succeeding in isn’t compassionate, it’s avoidance.

If you’re struggling with how to have these conversations, or you find yourself in the same patterns with multiple team members, that’s often a signal that it’s worth investing in your leadership skills. Executive coaching can help you build the confidence and frameworks to handle these moments more effectively.

Ready to take the next step? Or simply want to learn if coaching might be right for you. Please schedule a complimentary consultation here.