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How to Lead a Difficult One-on-One

Today’s post is a guest post from Nigel Green. He studied at Harvard Business School and spent nearly a decade in upper management with large healthcare companies.

According to a study by Psychometrics in Canada, nearly a third of employees deal with conflict on a regular basis.

And the cost of these internal politics is staggering. Another survey showed that 35% of people leave their jobs voluntarily because of internal politics.

Issues often start small. Most of us hear that small internal voice saying, “You need to deal with this.”

But we put off dealing with it because we’re afraid of the difficult one-on-one. And as a result, the small issue snowballs into something toxic.

If you’re having a conversation in your head about someone on your team, then it’s time to have the conversation with them. Here’s how to have the hard conversations. Follow this advice, and you can diffuse that tension before it starts costing your team.

1. Get in a Positive Mindset.

We’re calling these “difficult conversations” — and for a reason. Emotions can run high. You probably feel some amount of frustration. But it’s important to check your frustration at the door.

Instead, frame the conversation as an opportunity for improvement. If you tell yourself this conversation is a necessary step toward a positive outcome, then you’re more likely to get that result.

2. Get Clear on the Problem.

Before you go into the conversation, make sure you can state the issue in two or three succinct sentences. Cite specific observations as examples. This gives you the confidence and clarity to direct the conversation. It also safeguards you from our natural tendency to ramble and say something we don’t mean.

3. Make the Right Kind of Assumptions

As managers, we often think we know the backstory behind the issue. Get rid of those assumptions.

Instead, assume you are missing key information. Assume your teammate has only the best of intentions.

This attitude helps you listen to your employee’s perspective. When you do, you’ll probably discover new information that gives you fresh insight on the situation.

4. Ask Questions that Start with “What” and “How.”

Compare these two questions:

Why didn’t you finish your quarterly report on time?

…versus…

What happened with your report this quarter? Did I see it was submitted late?

The first question feels like an accusation. The second opens up a conversation.

Ask questions that start with “What” and “How.” Avoid questions that start with “Why” and “Who.”

The “What” and “How” questions establish a neutral tone and help you assume those best intentions. It allows space to transform the situation from a top-down reprimand into a coaching moment.

5. Let Your Employee Do the Talking

Here are two common mistakes managers make in these difficult conversations:

• We create a mental script of the conversation ahead of time.
• Then, we dominate the conversation.

There are two key questions that can help you avoid this.

First, after you’ve asked questions and described (simple and direct terms) the reason for your talk, ask, “Does this feedback sound fair?”

Second, ask your employee to describe to you how things will be different moving forward.

This gets your employee talking and keeps you listening. It helps you both stay focused on the goal of the conversation — basically, to understand and resolve the issue at hand.

6. Separate the person from the problem.

Before you end the conversation, affirm that while the result wasn’t good, your employee is.

In difficult conversations, always separate the person from the problem.

Emotions are a natural part of the workplace, but as managers, we have to be clear that we’re not reviewing our people’s worth, just their performance on the job.


No one enjoys difficult conversations. But low employee morale and high turnover are much, much worse. Use these simple tips to address issues and resolve them positively.

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