You’ve checked your facts. You’ve decided that a conversation really is needed. You’ve figured out when and where you’re going to meet, and you’ve even thought about how you’re going to invite the employee to talk.

Now comes the part we’ve been preparing for: actually having the conversation.

This is often the moment when even experienced leaders start second-guessing themselves. How do I start? What if they get defensive? What if they disagree with me? What if I say the wrong thing?

The good news is that a courageous conversation doesn’t need to be lengthy or complicated. In fact, the best ones usually aren’t. Your job is to be clear about the concern, listen to the employee’s perspective, work toward a solution, and make sure you both understand what needs to happen next.

Here’s how.

Start with the issue — not a compliment

If you’re relatively new to courageous conversations, practice the first few sentences before you meet. You don’t need a script to read from, but you do want to know how you’re going to begin. Practice with a trusted colleague, in front of a mirror, or even by recording yourself on your phone. Listen to your words and tone and pay attention to your facial expression and body language.

When the conversation begins, get to the point fairly quickly. You might say, “Thanks for taking a few minutes to chat with me. I have a concern I’d like to discuss with you.” Then explain what you’ve observed.

For example: “I’ve noticed that you’ve been texting during client time and also during some of our team meetings. I’ve seen this happening several times recently.”

Notice what’s missing from that opening? A compliment.

For years, leaders have been taught to use the “feedback sandwich”: say something positive, give the critical feedback, and then finish with another positive comment. The intention is good. We want to soften the message and protect the relationship. Unfortunately, it can also make the message confusing.

As Brené Brown puts it, clear is kind. If you have feedback to give, give it clearly and graciously. Your employees should absolutely hear from you when they’re doing good work—but those positive comments should happen regularly and genuinely, not because you need something nice to put on either side of a concern.

Describe what you saw, not what you think it means

Once you’ve opened the conversation, describe your concern in specific, factual terms. Focus on behaviour you have observed or information you have verified. This is where language really matters. 

“You’ve been texting during client appointments” describes behaviour.

“You seem unmotivated” is an interpretation.

“The report was submitted two days after the deadline” describes what happened.

“You have a poor attitude about deadlines” is a judgement.

Words such as unprofessional, lazy, disrespectful, unmotivated or bad attitude are likely to create defensiveness because we’re no longer talking about what happened. We’re making a judgement about the person. 

Stick with what you know.

Then explain why it matters. What effect does the behaviour have on clients, coworkers, service quality, the team or the organization? People are more likely to understand the importance of changing something when they understand its impact.

Be clear about what needs to change

Feedback shouldn’t leave someone wondering, Okay…so what am I supposed to do differently? That’s the constructive part of constructive critical feedback.

If an employee doesn’t know how to do something properly, your role may be to provide training, clarify a policy, demonstrate a skill or arrange some coaching. That’s a skill or knowledge issue, and you need to help address it. 

But sometimes the employee already knows exactly what’s expected and simply isn’t doing it. That’s different.

If everyone knows that phones aren’t to be used while working with clients, you don’t need to spend ten minutes rereading the policy. You can simply clarify the expectation: “I need you to stop texting during client time and meetings and stay focused on the people you’re working with. I expect that change immediately and on an ongoing basis.”

Clear doesn’t mean harsh. It simply means the other person shouldn’t have to leave the room trying to figure out what you meant.

Then stop talking

This may be one of the hardest parts for leaders. Once you’ve explained the concern and clarified your expectation, ask something like, “What are your thoughts?”

And then listen. Don’t interrupt. Don’t immediately correct their version of events. Don’t spend the time they’re talking preparing your rebuttal. You may learn something important.

Perhaps the employee tells you their mother is dealing with an urgent situation and has been contacting them repeatedly. Maybe there’s a family issue you knew nothing about. Maybe there’s a legitimate need for some temporary flexibility or accommodation. Or maybe the employee simply disagrees with you. Either way, you need to hear their perspective before deciding what comes next.

Help them find the solution — don’t automatically solve it for them

Leaders in nonprofit and human service organizations are often very good at helping people. It’s part of why many of us ended up in this work in the first place. That can make it very tempting to hear a problem and immediately ask, “How can I help?”

Sometimes help is absolutely appropriate. If someone needs training, resources or legitimate accommodation, that’s part of your responsibility as a leader. But not every problem belongs to you. Instead, try questions such as, “How will you manage this going forward?” “What strategies could you use?” or “What would better look like in this situation?” 

Those questions keep responsibility where it belongs while still communicating that you’re interested in the employee’s success. You’re not taking the problem away from them. You’re helping them think through how they will solve it.

Don’t get pulled into an argument

Sometimes an employee won’t agree with your feedback.

“Everybody does it.”

“I don’t think this is a problem.”

“I have a right to answer a quick text.”

This is where courageous conversations can turn into debates. Don’t take the bait. You can acknowledge the person’s disagreement without surrendering your responsibility as the leader. You might say, “I understand that you disagree. Let me clarify what I’m expecting.” Then state the expectation again.

Or simply: “I’m not going to argue with you about this. I believe you understand the policy, and I expect you to follow it going forward.”

Restating your expectation once isn’t arguing. Restating it six different ways while trying to convince the employee that you’re right, probably is. If a conversation that should take five or ten minutes is stretching much longer, ask yourself whether you’ve slipped into debate mode. Your goal isn’t to win. Your goal is clarity.

Finish with an agreement

In many courageous conversations, you and the employee will be able to identify a reasonable solution together. Before you finish, summarize what you’ve agreed to.

“Let me make sure we’re on the same page. We’ve agreed that…”

Clarify who will do what and, where appropriate, by when. If the change needs to happen immediately and continue going forward, say that.

You don’t necessarily need another meeting. In many situations, you’ll know fairly quickly whether the issue has been resolved because you’ll see the change—or you won’t. Then end the conversation like a human being.

You might say, “I appreciate your willingness to talk about this. I know you can make this change. Thanks.”

Done. A courageous conversation doesn’t need a dramatic ending.

What about documentation?

This is an area where organizational policies differ, so start by checking your HR policies, collective agreement if applicable, or talking with your HR professional.

Remember that the kind of feedback conversation we’re discussing here isn’t formal discipline. Automatically placing documentation about it in an employee’s personnel file can blur that distinction and make an ordinary coaching or feedback conversation feel like a formal warning.

If your organization’s policies don’t require formal documentation, you may still want a brief confidential note for your own supervisory records. Record the date, time and place, who was present, the issue discussed, expectations that were communicated, what was agreed to, and any follow-up that’s needed. A few sentences are usually enough.

The purpose isn’t to build a case against someone. It’s simply to create an accurate record that you can refer to later if necessary.

What we tolerate tends to continue

Susan Scott, author of Fierce Conversations, makes an important point about leadership: “As a leader, you get what you tolerate.”

We sometimes think we’re being kind when we overlook behaviour that needs to be addressed. But silence sends a message too. If nobody tells an employee there’s a problem, why would we expect them to change it?

This is one of the reasons courageous conversations matter so much. They give people information they need. They clarify expectations. They prevent small problems from quietly becoming bigger ones. And when they’re handled well, they can actually strengthen rather than damage working relationships.

Most of us want to know where we stand. In fact, one of the nicest things an employee can say about a leader may simply be:

“I always know where I stand with you.”

That’s what courageous leadership can look like.

Paula’s Leadership Challenge

The next time you need to give someone constructive critical feedback, resist two temptations: don’t sandwich the message between compliments, and don’t over explain it.

Describe what you’ve observed. Explain why it matters. Clarify what needs to change.

Then ask:

“What are your thoughts?”

And listen.  Sometimes the most courageous part of a courageous conversation is saying clearly what needs to be said—and then giving the other person room to respond.