Repeat Office Offenders: How Good Leaders Handle Next Level Difficult Conversations

You had a first meeting with a problem employee. You felt as though you made yourself clear. The other person responded in a positive manner and at the conclusion of the meeting, you felt as though you were both on the same page.

And then you witness the same employee repeating the same bad behavior.

Moments like this challenge leadership and authority. If one employee doesn’t listen to you, will others follow? Will your superiors lose their faith in you as a leader?

For women leaders, who sometimes still have an uphill battle in establishing authority, this problem can be even worse. To combat this, women leaders need to respond quickly and effectively.

Effective response requires understanding the best time to respond, having a plan in place and executing that plan. The following tips will help you prepare for next level difficult conversations.

Timing: When is the Best Time to Regroup and Have the Next Meeting?

How long should you wait to intervene? Your initial instinct might be to “give it some time” as that person might just be adjusting to a new behavioral routine. However, you need to ignore that impulse – the best time to intervene is right away. Delaying it could result in the employee falling further into bad routines and will undermine the seriousness of the conversation when you do have it. A lack of response might show co-workers that negative behavior goes unaddressed. And the negative employees might be creating a toxic work place. Here are keys to identifying when to act:

  • the first time you see an employee repeat a behavior that was addressed
  • seeing other employees adopting the bad behavior, and
  • when the office culture is being affected by negative behavior.

The key here is: Don’t hesitate; act.

Get Right Into It

It’s only natural to start off meetings with some small talk. In many meetings, it’s not only okay to do, it is expected. However, for a difficult conversation, especially one you’re having a second time, it is important to get right into the primary issue. Your counterpart may try to defuse the situation with small talk. Here are a few points for jumping right into the conversation:

  • avoid small talk by taking control of the conversation right away
  • have a clear agenda of items to discuss, and
  • script the conversation and how you are going to start it.

Don’t Fall for the Common Traps

During a difficult conversation, the other person might begin to feel threatened and respond accordingly. Some tactics your employee might try to use are:

  • anger
  • distraught crying
  • sarcasm
  • silence
  • becoming overly defensive

Have control over you own emotions in these situations. Don’t get pulled into an emotional conflict – even if the other person is insulting your work or making personal insults.

Remember to be firm in your position but willing to listen and keep emotion out of it. If the person receiving feedback uses passive aggressive language, push past it to get to the heart of the situation by saying “We need to discuss how the impact of how [issue] affects the company.” If the other person goes silent, say “I’m not sure how to interpret your silence.” Whatever the emotion being displayed is, you must remain calm, cool and collected.

Ensure Your Meaning is Understood

Similar to avoiding small talk, you’ll want to ensure that the employee is aware that this is a serious meeting. It’s likely that you’ve had meetings with this employee before, so you want to convey that this meeting isn’t one of those “little talks.” The following are all important in conveying the importance of the issue you’re discussing:

  • tone
  • demeanor
  • body language

An important tip at this point is to consider what, if any, role HR should play. It will depend on the individual situation, but you might want to consider documentation depending on the potential course of the conversation and steps afterward.

The Most Difficult Conversation: When It’s Time to Terminate

The most difficult conversation any manager can have is the one that ends in termination of the employee. It can be emotional, challenging and make you feel as though you failed as a leader. Again though, it is always important to leave emotion out of it. Chances are this will be at least the third conversation with the employee, if not even more. It will be different than any of those conversations because there should be less of a dialogue. Here are the key strategies to use during a termination meeting:

  • You’ll want to ‘script’ the conversation even more so than any of the others.
  • Use documentation from previous conversations as part of the script.
  • Plan each segment of the conversation ahead of time.
  • Allow a certain amount of time for each segment.
  • Maintain an even, serious tone throughout.
  • Decide ahead of time how the meeting will end and move toward that end.

While termination is sometimes a necessary final step, the majority of difficult conversations won’t end this way. Sometimes you only need to address someone once on an issue, but the repeat offenders can be a tricky balance. To prevent termination and coach a difficult employee into a productive member of the team, you need well-planned intervention and coaching techniques.


  1. Enjoyed the article: Repeat Office Offenders: How Good Leaders Handle Next Level Difficult Conversations.The only thing I see missing from this article is the self-evaluation of the person who is having the difficult talk with the employee. I have seen some leaders who do not evaluate themselves and their purpose when they are meeting with difficult employees. Sometimes the issues with going forward is not just on the problem employee. Sometimes the person’s perception of that employee is keeping the difficult situations going because of personalities or that difficult employee reminds the person of someone in the past that caused them distress. It becomes, “my way or the highway” syndrome. A whole unit was turned upside down because the leader, who had excellent skills, carried this kind of baggage. After two or three employees were fired, the company finally looked at the leader. Instead of someone really working with those employees to help them get to the next level and someone working with the leader, who was also fired, the company just went out to fill all positions again. Therefore, no one really resolved the real problem.

  2. I went through a situation with an employee recently and compared my strategy to yours and found we matched. For me the hardest part was feeling I had somehow failed as a leader for this staff member, but in the end realized we both were in better places because she needed to put herself in a position for which she was qualified and I needed someone truly qualified for the position.

  3. Hi Melody, thanks for your response. I understand how one might question their leadership in situations like those but it sounds like you might the right call, which is at the heart of great leadership. I’m glad that you found the strategies matched. Thanks for commenting on the real-world applications of these types of strategies.

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