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Empathy is your most important skill as a manager.

You are not managing resources and you’re not managing work; you are managing people. And people are complicated. People need more than just to be managed in order to be successful (and to make you successful as their leader). They need to be led, coached, appreciated, and nurtured.

As a leader, your job is to enforce the rules — but it is also to know when you bend or even break the rules for the right reasons. Things are going to happen to the people on your team, and it is your job to know how to react in the right way.

Today, we’re talking about the awkward, uncomfortable, oft-avoided difficult conversations you sometimes have to have as a manager, and how to do them with empathy.

The five difficult conversations we’ll be tackling:

  • When someone is having performance issues
  • When someone on your team has a personal issue at home
  • When someone’s project get cancelled
  • When someone on your team needs to improve their personality or hygiene
  • When someone disagrees with the company strategy

Handling each of these scenarios requires empathy of different kinds, and a willingness to acknowledge the humanity of every single person on your team. Let’s dive in and get uncomfortable!



When someone is having performance issues

How do you tell someone they’re doing a bad job?

Well, the answer to that question varies depending on the person. Have they always done a good job in the past and this is a new development? Or are you acknowledging that they haven’t been doing a good job for a long time?

If the person has been doing well but seems to have taken a turn for the worse recently, then the first thing to do is to acknowledge that their performance has changed. The change is what should be addressed, not just the work. Invite the person to meet with you, and make them aware that you’ve noticed a change in their work. Can they offer any insight into what’s going on?

If they are someone who has usually done really well, they will probably have noticed the change themselves and will have an idea of what’s going on or what is at the root of their change in attitude or productivity.

From there, you can troubleshoot solutions. If they’re going through a personal issue that’s distracting them, maybe they can take a day off or find ways to lighten their load for a while. If they’re feeling disengaged from the project, you should talk to them more about that. Why is their interest waning? Have their goals changed? Has a new process made a part of their job much harder to do? Find ways to realign their day-to-day work with their goals to help them get back on track.

If, on the other hand, the person has never been good at their job, then you need to talk to them about their performance.

To have that conversation, start by looking at the facts. And the facts are that this person isn’t performing up to speed, whether that means missed deadlines, shoddy work, or failure to make key parts of their role happen. Be clear here; use real examples and numbers so that there is no doubt. This was the expectation, this was the result we received, and these things don’t add up.

When you lay out clearly how this person has not met the standards required for the job, then you can begin to address the “why” behind it.

Start by asking the person why. Give them lots of room to explain; don’t assume that you know the reason. Be open to hearing what they think is going wrong. It could be they are missing skills, or it could be that they didn’t fully understand what was expected of them in this role when they were hired. The reasons are wide-ranging and it is only by understanding where they are coming from that you can make real decisions about what to do next.

You can end the conversation by asking what they want to do about it. Make it clear what is expected of them in this role. Is that something they want to do? Are they able to do it? If not, talk about what should happen next (leaving the team, switching roles, taking a course to get new skills…all depending on what makes sense for your team).

And a final note here: always keep the conversation about the work, not the people. Never tell them how their bad work is affecting you personally or making your life harder; instead, always keep it focused on the facts and things they have control over. Don’t give people a reason to be mad at you rather than making changes to themselves.


When someone on your team has a personal issue at home

What do you do when a person on your team goes through a breakup? What about if their pet dies?

Most companies don’t have policies in place for pet bereavement or employee breakups, but a lot of the time, people going through these kinds of personal crises can be in more pain and less focused on their work than if they were coming into the office with the flu.

And yet, as employees, most of us feel like we have to come into the office in the midst of these personal issues. And I don’t know about you, but I do not do my best work when I’m going through something big at home and trying to pretend everything is normal at work.

So as a manager, you have an opportunity here. When you know someone on your team is going through something, take an opportunity to do the right thing for them. Invite them to your office or send them an email, letting them know you are aware they are going through a hard time and that you are here for them. And if you can (and it feels appropriate), give them time off.

Just being available — listening to them talk, sharing your own similar stories, or giving a person space to acknowledge they are going through a hard time and might need a slight shift at work for a while — is one of the most powerful things you can do as a manager to show your team that you truly care about them.

Make it absolutely clear that you understand where they are coming from, and that you aren’t assessing their personal feelings or issues as part of their job performance. Never forget, you are managing humans — not resources — and sometimes the humans on your team will need a little extra humanity from you.

Most people will bounce back from a personal crisis, so any productivity you lose for a week or two will come back. And will be more long-lasting, since people are more likely to stay on a team where they feel appreciated and cared about.


When someone’s project gets cancelled

One way to tell everyone that a project has been cancelled is to get everyone in a room and make a big announcement. But anyone who has been in that kind of meeting will tell you: that sucks.

It’s much more valuable to sit down with the key people involved in a project one-on-one to let them know what happened and what is happening next. To each person on your team, this is a big personal change, so it is worth treating it that way.

Give people space to be disappointed; try to see it from their perspective and give them space for their feelings. Something they may have been really excited about or already spent hours working on is just going away — and that feeling is not good. So listen to people complaints and doubts, and be prepared to give them a plan for what to do next.

If they ask a question, answer it as honestly as possible. If you don’t know the answer, say so. Let them know you’ll check with your own manager and get back to them — and then actually do that.

Then give people context for what this change means for them. What will they do next? Do they need to be worried about losing their job? Will their work be able to be used somewhere else later? The more prepared you can make people for what a situation means to them, the faster they’ll absorb it and the more effectively they’ll be able to move on.


When someone on your team needs to improve their attitude or hygiene

Have you ever worked with someone who smelled really bad, or who walked around like they had a raincloud over their head all the time?

Sometimes, people’s personal choices can really negatively impact the people around them and actually hurt team morale.

It’s easy to identify and talk to someone who is being aggressively negative or hurtful with the people around them. But what about subtle things that are holding someone back by making them an outcast from the team?

Well, the first thing not to do is pull them into your office and say, “Everyone’s been complaining to me about your ____.” You don’t want to make them feel like everyone hates them or is talking about them behind their back.

Instead, you want to let the person know you care about them and that you want to offer them advice to help them be more successful. You can say, “I really appreciate how much time you spend at the office, and I know you’re in a hurry to get here in the morning. But it is important that you dress for the job and shower before you come to the office. Your personal hygiene is affecting the way people think about you and taking away from your awesome work, and I want you to get credit for all the great work you do.”

You can trade out “attitude” or any number of personal issues in that brief message above for “hygiene” and present your team member with caring advice that is related to their work and success, not what you or anyone else thinks of them personally.


When someone disagrees with the company strategy

Part of being a great manager is keeping everyone on the same page. But that can be a challenge, since there are so many times at work where there are lots of ways to get to the right answer, and everyone may not agree on what the best approach is.

The first thing to remember when someone approaches you with concerns about company strategy is that this person’s opinion matters. They think it is important, or else they wouldn’t have brought it to you, so you have to take it seriously.

So your first approach should be to make sure this person has enough information and the right information. You might not have done a good enough job explaining the strategy, or they might not have context that you assumed they had. Offer them more information and let them ask questions.

Use questions to help the person come to a conclusion that leads them to the right answer. What do we need to do to make your plan work? What information don’t we know that would impact this decision? Help them think through the problems in their idea on their own and let them come around to the right answers; that will help it stick more and mean more.

You don’t want to let them walk out feeling unresolved, or else they’ll still have their nagging doubts hurting their productivity and engagement.

Other times, someone might bring an objection or concern to you that you think is totally valid. But it’s important not to say, “Yeah I think this idea totally sucks too!”.

You need to get the party line before you totally agree or disagree with an objector on your team, and then stick to it. Your team only functions when people are working together in a unified direction.

Your job as a leader is to make the company strategy happen, which means you have to align yourself with it, even if you’re not totally convinced. And if you’re not convinced, it’s your job to get the context you need to get on board, and then to translate that down to the people on your team.

So don’t agree with any objectors overtly, even if you think they have a good point. Instead, validate their good points, and let them know you hear them. If they raise an objection you don’t have a good answer for, tell them, “I don’t have all the answers. Why don’t I go talk to my boss about it and I’ll circle back with you. Neither of us has enough information to make a total decision about this.”

That way, if their point really is valid, you get the chance to pass it up your manager and improve the strategy. Otherwise, your manager will be able to help you understand why that point doesn’t work and how you should communicate it to their team.


Difficult situations happen all the time at work, and ignoring them only makes them worse. As a leader it is your job to face the challenges with the people on your team head on, and to approach them with empathy, compassion, and a goal of bringing everyone together on the same page.

What’s the last difficult conversation you had at work? How did you handle it, or wish it was handled? Share your thoughts in the comments!


Tags: empathy, leadership, management, relationships, team, trust,

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