Before You Have That Difficult Conversation: Get Ready First

Paula MacLeanMonday Leadership MinuteLeave a Comment

You know you need to talk with an employee about something.

Maybe they’re missing deadlines. Maybe something happened with a client or coworker. Maybe you’ve noticed a pattern in their performance that needs to change.

You’ve decided you’re going to address it. Good.

But here’s where leaders sometimes get themselves into trouble: we finally work up the courage to have the conversation and then jump into it without getting ready.

A little preparation can make an enormous difference. And no, preparation does not mean lying awake at three in the morning rehearsing every terrible way the conversation could possibly go. That’s not preparation. That’s worrying.

Instead, let’s walk through three practical steps that can help you go into the conversation feeling calmer, clearer and much better prepared.

First, is this actually a conversation you need to have?

This sounds obvious, but it’s worth taking a few minutes to make sure you know what you’re dealing with. Start with the facts. Sometimes information reaches us second hand—or thirdhand. Someone tells us what another employee apparently said or did, and before long we have a fairly convincing story. 

But that’s exactly what it is at this point: a story. Every person who passes along information filters it through their own perceptions and experiences. What you’ve heard might be completely accurate. It might be partially accurate. Or it might be a misunderstanding. So before you talk with the employee, ask yourself:

What do I actually know?

Verify the facts wherever possible. Then ask another important question:

Is a conversation the appropriate response?

Most day-to-day performance and workplace issues can—and should—be addressed through timely feedback and conversation. But some incidents are more serious. A quick five-minute chat isn’t necessarily the right response to every workplace issue.

If you’re unsure, talk with your manager or HR professional before proceeding. And if you work in a unionized environment, make sure you understand and follow your collective agreement.

Don’t wait forever

You’ve probably heard of the “24-hour rule”: when there’s a problem, deal with it within 24 hours. Nice idea. Real life doesn’t always cooperate. You may need time to verify information. The employee may not be working tomorrow. You may need to consult HR or your manager before deciding what to do. 

The important principle isn’t really 24 hours. It’s don’t keep putting it off. Give yourself a deadline. “I will address this by Tuesday afternoon.”

Putting a date on it helps prevent Tuesday from becoming Wednesday, Wednesday from becoming Friday, and Friday from becoming maybe this will magically disappear.

Step two: Plan the logistics

Once you’ve decided a conversation is appropriate, work out the practical details.

How will you meet?  Whenever possible, have the conversation in person. A virtual meeting can also work, particularly for remote teams. Email and text? Almost never. Too much gets lost. You can’t hear tone, see facial expressions or adjust your approach based on how the other person is responding. This is a conversation. Treat it like one.

Where will you meet?

Privacy matters. Choose a place where both of you can talk comfortably without being overheard. The local coffee shop might feel anonymous, but it isn’t private. Neither is the hallway, lunchroom, parking lot or the corner of a shared office. Find a room with a door that closes.

When will you meet?

Choose a time that works with the employee’s schedule, even if that means moving something in yours. And remember, this doesn’t need to become a 90-minute summit. Many feedback conversations take five or ten minutes. Fifteen minutes is often plenty.

When possible, I also prefer having these conversations toward the end of someone’s workday rather than first thing in the morning. If the employee is upset or needs time to think about what you’ve discussed, they don’t necessarily have to carry those emotions through an entire workday.

Who should be there?

For ordinary feedback, usually just two people: the leader and the employee. If you’re working within a collective agreement, check its requirements. There may be circumstances where representation is required. There may also be situations where either you or the employee would benefit from another appropriate person being present because of safety, sensitivity, power dynamics or other circumstances. If you’re unsure, consult with HR or your manager beforehand. The goal isn’t to make the meeting feel intimidating. It’s to create an environment where everyone feels safe and the conversation can remain professional.

Step three: Plan the invitation

This is such a small thing—and yet it’s where many leaders begin feeling nervous.  How exactly do you ask the employee to meet? Think about the difference between:

“I need to meet with you.” And “When you have a few minutes, I’d like to chat with you.”

Same basic request. Very different feeling. Your language should fit the seriousness of the situation. There’s no reason to make a relatively minor concern sound ominous. You can also reduce uncertainty by giving the employee some practical information:

“Could we chat around three this afternoon? It should only take about ten minutes.”

And make the invitation privately. Calling across the room after a staff meeting, “Bob, I need to see you in my office later,” doesn’t just make Bob wonder what’s going on. Now everybody else is wondering too.

“What’s this about?”

Be ready for that question. It’s perfectly reasonable for an employee to ask. Depending on the situation, you might say:

“I have a concern I want to share with you and get your perspective on. It’s not a big deal, but I’d like us to talk about it.”

Or perhaps:

“I’d prefer to talk about it when we meet this afternoon.”

And sometimes there’s an even easier solution:

“If now works for you, we can talk about it now.”

The important thing is to think about this ahead of time so you’re not caught off guard.

Preparation is not the same as scripting

You don’t need to memorize a speech. In fact, please don’t. A courageous conversation needs to feel like a conversation, not a performance. What you can practice is how you’ll begin. Say the first few sentences out loud. Practice in front of a mirror. Try it with a trusted colleague. Or make a quick selfie video and watch yourself back. Pay attention not only to your words, but to your facial expression, body language and tone. It may feel slightly ridiculous. Do it anyway. Practice makes something unfamiliar begin to feel familiar.

Uncomfortable doesn’t necessarily mean unsafe

There’s an important distinction here. Our bodies don’t always distinguish immediately between danger and discomfort. Both can create that internal message telling us:

Get out of here. Avoid this.

Sometimes that response protects us from genuine danger. But sometimes we’re simply doing something unfamiliar. That’s worth remembering when you’re about to have a conversation you’ve been dreading.  Ask yourself:

Is this actually unsafe—or am I simply uncomfortable?

If you’ve checked your facts, chosen the right approach, planned the conversation and thought carefully about how you’ll begin, you may still feel nervous. That’s okay. You don’t need to eliminate the discomfort before you act.

One final question

Before you walk into the room, ask yourself:  

What would a great result look like?

Maybe the employee understands the concern and agrees to make a change. Maybe you discover information you didn’t know. Maybe you solve a problem together. Maybe the conversation isn’t entirely comfortable, but you leave with greater clarity and agreed-upon next steps. Then ask:

What do I need to do to help create that result?

That question shifts your attention away from everything that might go wrong and toward what you actually want to accomplish. And that’s a much better place from which to begin a courageous conversation. 

Paula’s Leadership Challenge

Think about one conversation you’ve been putting off. Don’t have it today. Prepare for it today.

Check your facts. Decide whether a conversation is the right approach. Choose when and where you’ll meet. Practice how you’ll invite the person and how you’ll begin. Then put the conversation in your calendar. Because courage is important. But courage plus preparation is a whole lot better.

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