How to Have a Difficult Conversation With an Employee
Most leaders put off the hard conversation because they care about the person. The kindest thing you can do is have it early, privately and clearly, so they have a real chance to fix it.
Have the conversation soon, in private, and start by saying why it matters. Describe the specific behavior and its effect rather than judging the person, ask for their side and really listen, agree together on what changes and by when, and schedule a follow-up. Being clear is kind; leaving someone to guess is not.
I have never met a good leader who enjoys difficult conversations. Most of us delay them for the same reason: we care about the person and we do not want to hurt them. So we wait for the right moment, hint at the problem, hope it fixes itself, and in the meantime the issue grows and the rest of the team watches to see whether anything will be done.
Over time I have come to believe that the delay is the unkind part. When you avoid a hard conversation, you take away someone’s chance to improve while it is still easy. You also make the eventual conversation much harder, because now it includes months of frustration they did not know about.
Why is being direct the kind thing to do?
Because people cannot fix what they do not know about. Most employees who are struggling would rather hear it plainly from someone who wants them to succeed than find out later in a review, or worse, never find out at all. Clarity is a form of respect. It tells someone you believe they can handle the truth and do something with it.
Direct does not mean harsh. You can be completely clear and completely kind at the same time. The goal is not to win the conversation. It is to help the person succeed, and everything about how you prepare should point in that direction.
How do you prepare?
Prepare in four steps
- Get specific. Write down the behavior you have seen and when. “You were late to three of the last five team meetings” is fair. “You do not seem committed” is a judgment.
- Know the impact. Be ready to explain why it matters to the team, the customer or the patient.
- Decide what good looks like. Know what you are asking for so you can say it simply.
- Check your own part. Ask whether expectations were clear and whether they had what they needed. Sometimes the problem started with us.
How do you have the conversation?
Do it soon and do it in private. Start by telling the person why you are meeting and that you want them to succeed, and mean it. Then describe the specific behavior and its impact, briefly, without piling on extra examples or softening it so much that the point disappears.
Next, ask for their side, and listen as though you might learn something, because you often will. A person who is always late might be dealing with a childcare change. A person whose work has slipped might be overwhelmed, unclear on priorities or struggling with something outside of work. You do not have to accept every reason as an excuse, but understanding it helps you find a solution that actually works.
Finally, agree together on what will change and by when, and put a follow-up on the calendar before you leave the room. End by restating your confidence in them. People tend to rise to the expectation you show them.
Phrases for a hard conversation
- “I want to talk about something because I care about how you are doing here.”
- “Here is what I have noticed, and here is why it matters.”
- “Help me understand what is going on from your side.”
- “What would help you turn this around?”
- “Let’s check back in on the fifteenth and see how it is going.”
- “I believe you can do this, and I want to help.”
What if the conversation goes badly?
Sometimes people get defensive, upset or quiet. That is a normal human reaction to hearing something hard, and it does not mean the conversation failed. Stay calm, acknowledge how they feel, and give them space. It is fine to say, “I can tell this is hard to hear. Let’s take a day and talk again tomorrow.” The follow-up conversation is often the one where real progress happens.
Follow through, in both directions
When the follow-up comes, notice improvement out loud. If someone made the change you asked for, tell them you saw it and that you appreciate it. That recognition is what turns a hard conversation into a turning point instead of a bad memory. If nothing has changed, have the next conversation just as clearly, with clearer consequences. Fairness means holding the standard and giving people every honest chance to meet it.
For more on giving feedback people can use, see Truth Over Praise and Nobody Has Told You The Truth In A While. Hard conversations are one of the leadership skills we practice in You Are Capable of More: Leadership, my interactive leadership workshop.
Have the hard conversation early and privately. Be specific about the behavior and its impact, listen to their side, agree on what changes and by when, and follow up, including noticing out loud when they get it right.
Frequently asked questions
How do you start a difficult conversation with an employee?
How do you have a hard conversation without hurting morale?
When should you have a difficult conversation with an employee?
What if an employee gets defensive?
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