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Work: talking to employees

How to have a difficult conversation with an employee

The conversations managers put off the longest are rarely complicated on substance. The hard part is saying something plainly to a person you work with every day. Pick a situation and rehearse it before it happens for real.

Conversations to practice

What helps in any difficult conversation with an employee

  • Facts, not judgments

    “You started after nine three times this month” works better than “you are unreliable”. A fact is hard to argue with, a judgment is easy.

  • A question before the solution

    The other person often has a reason you do not know about. One question about their view saves a lot of misunderstanding.

  • A clear ending

    The employee leaves knowing what changes, from when, and when you will check in again.

Frequently asked questions

How do I start a difficult conversation with an employee?

With the reason for the meeting, in one or two sentences. A long warm-up and compliments before bad news make people wait for the “but” and miss everything else.

What if the employee gets defensive or blames others?

Listen, do not interrupt and do not get into comparisons with other people. Then return to the specific behavior and its impact. Defensiveness usually eases once the person feels heard.

Should someone else be in the room?

For conversations about ending employment, companies often invite someone from HR. For feedback, one-to-one is usually better. Check the rules at your company.

How can I practice without involving my team?

The AI plays an employee with their own history, emotions and reasons that come out only during the conversation. You can repeat it several times, try a different opening and compare the reports.

See also

Rehearse it before you book the room.

Pick a situation, talk to an AI employee and see in the report where the conversation went well and where it got stuck.