How to have difficult conversations with your employees

As a general manager at several high-end hotels, I’ve had to conduct many difficult conversations with my reports. But there’s one conversation that’s more difficult than others—when an employee who has made positive contributions to the organization is, for whatever reason, underperforming. You don’t want to fire the person, and you don’t want to demotivate them. It’s a delicate balance, and it took me a while to learn to do it right.

The downsides of emphasizing weakness

Early in my career, I had a sales manager (call her Sally) whose team was underperforming. The team seemed to like her. The group was relatively conflict-free, but they weren’t meeting their numbers or executing on new management mandates. I figured I could coach Sally up.

So, I charged ahead and decided to take a transparent and direct approach. I sat Sally down in my office, outlined the problem, and what I thought she could do to solve it. And I got precisely nowhere. Sally felt I was being unfair and threatening the smooth functioning of her team.

I asked myself, what was I doing wrong? It turns out that while I was thinking about what I could do as a manager, I wasn’t thinking about who Sally was and what she was doing well. I actually knew little about her, which led me to focus on her weaknesses, not her strengths. I learned quickly that that is not good management.

Identifying employees’ hidden talents

A few years later, the operations manager of a hotel I led (call him Bill) showed flashes of talent. For example, he could articulate the issues our main restaurant confronted and knew what it needed to do to improve. But he couldn’t implement his solutions.

This time, I did my homework. I learned about Bill before I tried to coach him. I knew he wanted to do well and yearned for a director’s title. But I saw that he had reported to multiple bosses over his career (which, in itself, is not a great thing), and they had done little to help him advance. Not surprisingly, he began keeping his head down, doing what they asked him to do, but little more. Consequently, there was nothing in his history that argued for a promotion. And, after 10 years, he hadn’t gotten one.

I felt the hotel would be better with Bill than without him, and I knew that he had the potential to become a director.

Beginning the conversation the right way

This time, I decided to approach things differently. I started by inviting Bill to join me in casual lunches or quick cups of coffee at the hotel’s diner. (The boss’s office is an inherently scary place.) While we waited for our coffee or meal, I’d point out a host stand left unattended or music that was too intrusive. This helped him understand what I was looking for in a nonthreatening way. I let him do the talking. Then I started inviting his direct reports to join us to analyze areas of operational opportunity. This enhanced his authority in front of them and boosted his confidence.

I never told Bill why I was doing this. The first step in coaching, I had learned, is to make the person feel valued and safe. Over the next six months, Bill began to implement his ideas. His reports turned to him with their own. He got his promotion to a director position, and now he helps his reports by identifying their strengths and partnering with them in a mutual effort to improve their performance. He uses the same template I used with him.

What about Sally? When I did my homework on her, I discovered that several years before I arrived, the sales team had been in turmoil due to a meddling CEO. Sally had resolved conflicts and calmed the team, and she came to see that as her central strength. And it was. But I hadn’t focused on that, because I hadn’t spent enough time getting to know her to realize that. Instead, I hammered on what I perceived to be her weaknesses.

I met with Sally again in a more relaxed and casual setting. I asked questions, and more importantly I listened. We strategized about how to improve her team’s performance. And, over time, it did. This was the lesson I learned from Sally and applied with Bill: The best way to start this conversation is by being positive, recognizing the person’s strengths, and letting them know you value them.

The three-step process for conducting “the conversation”

I began to develop a systematic approach for conducting difficult conversations. If you’re a manager, and you don’t know where to start, following the three-step process below can help:

Begin on a human note. All work is personal, and knowing the details of a report’s history enables you to understand why he or she is underperforming. Make sure to treat it like a dialogue, not a lecture. I often begin by asking the person to tell me something they thought they did particularly well. After that, you can ask why it’s been difficult to repeat that success. Remember, your job as a manager is to assess their strengths so you can build the best leadership team for your business.
Stress action. Come into the conversation with specific ideas for what the employee can do based on her strengths. Sally had excellent soft skills; Bill had creativity and intuition. My job was to help Sally and Bill execute. Having specific ideas doesn’t mean reading from a script; it means you have possibilities in mind that you shuffle according to what you hear. That requires you to listen more than you talk.
Create awareness, get an agreement, then follow up. As with most leadership and coaching initiatives, start by creating awareness: What is the issue? Once there is mutual understanding, make sure you and the employee align yourselves on the plan. Because execution was a challenge for Bill, we surrounded him with people who were driven to cross tasks off their lists. That helped support his strategic strengths.

I’ve been on the other side of the desk for a “shape-up-or-ship-out” conversation, and I know it’s essential to end these exchanges on a positive note. Whatever sector you’re in, no matter how big your business, it’s still a small world. One day, the person sitting across from you could be your boss.