How to Tackle Uncomfortable Conversations at Work - Business Results
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How to Tackle Uncomfortable Conversations at Work

How to Tackle Uncomfortable Conversations at Work

An employee consistently shows up late for work. Another uses inappropriate language during meetings. A third is fine in their work environment, but lately is making errors resulting in other problems. Though their problems are different, they have one thing in common – their manager needs to have an honest, but possibly tough, conversation with them.

According to one Harris Poll, 69% of managers are uncomfortable communicating with their employees. Another 37% are uncomfortable giving direct feedback if they anticipate they will get back a negative response. However, when conflict or problematic behavior arises, it needs to be addressed and corrected. One part of being an effective manager is being able to have those conversations with employees, regardless of how difficult they are. For managers who avoid conflict, this can be a nightmare.

The manager who avoids addressing a conflict, is tacitly approving (whether they approve or not) and are allowing whatever the problem is to fester and worsen until disaster strikes, or that tough conversation finally becomes unavoidable. They may make excuses for poor behavior, turn a blind eye, or allow their employees to walk over them, simply to avoid talking. This is because to them, hard conversations cause stress. To avoid the stress, they engage in avoidant behavior. While avoiding a stressor might be their short-term individual preference, it doesn’t help the business, nor does it help the employee to perform at a higher level. It only leads to more serious consequences and additional stress for all involved.

While you can’t avoid conflict, you can make the experience less challenging to get through. Here are some tips strong managers use to have difficult conversations with their employees:

Before the Meeting

  • Don’t Wait! When you ignore a problem, you signal to your employee that their behavior is acceptable. When there is a problem, schedule a talk with them in the days following the incident.
  • When you schedule the meeting, have a shared agenda with key points and a clear plan of what will be discussed. This allows both of you to arrive prepared, and ensures the employee doesn’t feel cornered. The meeting should ideally be in-person, as tone and subtle body language can often be lost over video-conference. If you must meet virtually, make sure cameras are on, and be sure to check in often and clarify meaning. Obviously, only the persons involved in the incident should be included, but HR may also need to be involved depending on the severity of the situation. Practice what you need to say, and the tone in which you will say it, but be mindful that you will most likely not be reading a “script” in the moment. Human conversations twist and turn, and you cannot predict what someone else will say. HR or another supervisor should always be in a meeting where negative information is being given, this person should be a silent witness, so you do not get into a “he said/she said” situation.
  • Reframe & Breathe. If you dread a future conversation, thinking it is difficult and will go poorly, you are more likely to have a negative outcome. To reduce your anxiety, try to reframe the meeting. You aren’t giving negative feedback; you are providing constructive criticism to help your employee grow. Treat the meeting as a normal conversation between manager and employee. Take deep, slow breaths leading up to the meeting, to further stop the anxiety spiral.


During the Meeting

  • Body Language. Your nonverbal communication should indicate friendliness, confidence, and interest in what they are saying. Smile, make eye contact, and keep your body pointed towards them. This shows your employee that you aren’t a threat to them, and that you care about what they are saying. If possible, both of you should be sitting, preferably with little separation, and your posture should be relaxed but upright. Putting yourselves on an equal level makes it a conversation, not an interrogation, while confident posture reminds them that you are still the boss. Avoid crossing your arms and legs, facing toward the door, pinching your face, or rolling your eyes.
  • Keep a calm, measured tone of voice. Be firm, but not aggressive. When you are speaking, slow your rate of speech and manage your pauses. This allows you to keep emotions in check, and give yourself a chance to think before you speak. Avoid passive-aggressive language.
  • Be Empathetic. You and your employees are humans, not robots. Your employee may be feeling embarrassed, hurt, or even angry. You are there to help them move on from this, by acknowledging their feelings and perspective, while focusing on the facts. Don’t forget that they may be experiencing an issue outside of work, which is affecting their work life. They may not be aware of the impact of their behavior, or even know that it is a problem.
  • A Simple Formula. In your meeting, outline the incident, the impact of the behavior, what needs to change going forwards, and the consequences that will occur if it doesn’t. Be certain to link the behavior to its impact on the work output, rather than harping on the behavior. Avoid making it personal. Try saying something like, “This may not have been your intention, but X behavior results in Y outcome” or “Doing X, gives the impression that Y”. Don’t lecture about how wrong they were, simply make your point, listen to their side, and then make sure you are both on the same page as to how to move forward.
  • Ask Questions. Open-ended questions avoid yes-or-no answers, which can shut down a conversation. Your language should be non-judgmental, and solely focused on finding new information. An open question encourages employees to share information in a comfortable way.
  • Corrective Action. A clear request for change should always reinforce the benefit to the employee. You are showing that you are invested in retaining them, rather than firing them; you are legitimately concerned for their wellbeing and professional development. If the corrective action is predetermined by your business, outline them clearly. Avoid showing up to the meeting with a bunch of punitive tasks and to-dos. Don’t add drama with threats or power plays. Your employee will only feel resentment, and is unlikely to learn anything from the experience. If there is no standardized path forward, work together as a team on an appropriate course of action. By discussing a plan with your employee, you give them a sense of control over their situation, and they are more likely to be receptive to change. Keep in mind that the path forward may not be the exact one in your mind – offer ideas and be open to their suggestions. Your plan should follow what was discussed in the meeting, involve clear expectations and goals, and note what will happen if goals are not met.


After the Meeting

  • After the meeting, go over what happened with yourself. Review your notes, and ask yourself what went well. What could you improve upon? By asking yourself why you reacted emotionally to some things, you can disarm those triggers in the future. You’ll be even more prepared for the next conversation.
  • Follow Up. Strong management involves leading by example. Take responsibility for the solution you created together in the follow-up. Check in with your employee occasionally, to see how they are meeting their goals, but avoid micromanaging. Ask them if they have any thoughts from the last conversation, and if they have anything on their mind. Talk to them as a person.
  • Continue Fostering Openness. If you practice what you preach, they will follow. Creating a culture of feedback opens the door for easier discussions in the future. Feedback becomes seen not as an attack, but as an opportunity for growth.
  • Remember to document all of the conversations you have with employees; you won’t remember all the details later and you may need it later. Remember, if it is not documented, it did not happen!


Finally, while tough conversations are inevitable in life, you have control over how painless they are. By being a strong manager, you can work towards the best solution for your team like a true leader. Conflict doesn’t always have to be a fight – sometimes it is a puzzle you work on together.