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Difficult Conversations

You know how it works. Tom treats deadlines as if they are non-essential and expects bonus points if he ever hits one. Pam trash-talks co-workers to anyone who will sit still for five minutes. Jordan either comes late, leaves early, or takes an extra hour for lunch every day. You know it’s time for a difficult conversation, but you just can’t face it. If you’re a leader, however, you’re going to need to get used to managing difficult conversations once in a while. They’re part of the job. To lead well, you must be able to sit across from another human being and successfully deliver news they don’t want to hear.


Difficult conversations can be on many topics but are often related to performance, career conversations, or more personal aspects of behavior like attitude or demeanor. Elizabeth Freedman, principal at executive coaching firm Bates Communications, says the most challenging conversations with employees are the ones that go beyond simple fact-based discussions to touch on topics more sensitive or personal in nature; and ones that were left to fester over time. They’re often related to performance, lack of advancement, letting people go, aspects of behavior that are more nuanced like demeanor, hygiene, or attitude. She adds, “Sometimes it is not about what you are saying but the fact that you didn’t say something in a timely way, that you have let an issue become more pronounced. When you don’t nip things in the bud, the discussion is much harder.”


Executive coach Bruce Mayhew says there are three conversations that tend to come up most often: Annual performance reviews where there is a disconnect between what the employee expects and what management is sharing. An employee missing deliverables or submitting work that is not up to expected standards/quality. An employee not exhibiting the values and policies of their workplace. This often impacts respect for their co-workers, customers, and suppliers.


How a manager handles difficult conversations can have a huge impact on their relationship with their team. A poorly handled conversation can erode trust and negatively impact morale and productivity, and that means your team isn’t reaching their goals.


Preparation before the conversation makes the chances for a successful meeting much higher:

  • Get the facts. Pull up any key metrics/dates/incidents related to your conversation ahead of time and review the details. Check any relevant company policies or rules that pertain to the situation. You may need to bring HR into the situation.

  • Consider their perspective. Try to see what they think and feel.

  • Acknowledge and handle any emotions. You probably have associated some emotions with this situation. Are you angry? Disappointed? Worried? Bringing them into the conversation will only make things worse.

  • Consider possible solutions. What are you hoping to achieve from this conversation? What might be a win-win solution?

  • Create an objective statement. Break the sentence down into three parts by answering these questions: What seems to be happening? How is it impacting the team? What would you like to achieve?

When setting up a difficult conversation:

  • Schedule plenty of time for the conversation.

  • Don’t book a highly visible meeting space. Assure privacy.

  • Remove distractions. Choose a time and place where there will be few interruptions.

  • Don’t delay; talk about it when it is fresh.

Here are some simple questions to help launch the conversation:

  • How’s everything going?

  • How are you feeling about joining the team?

  • I have an idea of what we need to accomplish, but do you have any suggestions on how we can meet that goal?

  • Can I have a second of your time to talk about some feedback we’ve received about your behavior?

You don’t want your employees to feel like they’re in trouble. Otherwise, they’ll have the mentality that they’re on an inevitable path to termination and lose motivation for their job.


Make your conversation an open dialogue with proven facts and data to support your case.

Always end the meeting on a positive note. Your employee should leave thinking they can do better. You want them to feel accountable for metrics and committed to meeting their goals.

  • Focus on facts and real examples. Stay away from words like always and never.

  • Truly be present. Put your phone away.

  • Know your triggers. Be careful of yours and theirs and refuse to respond.

  • Show you care. Think about how you can convey to the person that you care about them and what happens to them.

  • Recognize the emotional impact. Even bad news like downsizing can be done respectfully. Recognize that this is bad news and will have a significant impact on the person.

  • Be clear and honest. If there is hope that the situation can change if they make progress toward the goals, make sure they know that. If there is no option for that, don’t give false hope.

It’s almost always a good idea to make notes before the meeting to keep you on track, and always take notes during the meeting. Be sure to jot down what was discussed, and any next steps you’ve landed on together. Make sure the conversation isn’t wasted.


Elizabeth Freedman reminds us that “the reaction you get in the room is not necessarily the full picture of what the person is thinking and experiencing. Not everyone reacts visibly. Some people shut down or are not ready to process the information in the moment. It may take days or weeks to process the information. There are physical signs that things are going badly: flushed cheeks, stiff sitting position, sweaty palms, restlessness, refusal to make eye contact. Sometimes it’s good to stop and ask the employee how they are doing, and even see if the appointment needs to stop today and come back in 24 to 36 hours. Just make sure you finish the conversation.”


Following up after a difficult conversation:

Follow-up is not to rehash the conversation, but to acknowledge the mutual accountability and actions related to the next steps discussed in the room. But it’s also important to follow up to check in on the employee. Be very thoughtful and caring.

  • Following up should start the next day. Take a face-to-face moment to tell your employee that you appreciated the conversation you had.

  • Offer your employee the chance to ask any follow-up questions or, if needed, continue the discussion. Make sure they feel like they got to share their side.

  • Check in regularly on any action items you set in the meeting. Don’t badger them with daily follow-ups—every few days or once a week is fine.

  • Celebrate positive progress promptly. This keeps them focused and motivated. Don’t let their hard work go unnoticed. If you see progress begin to falter, steer them back on track with a quick review of your meeting notes and action items.

Some miscellaneous tips may help you:

  • ·Don't sugarcoat the message, but be kind.

  • Create a feedback culture. Difficult conversations, whether at home or at work, tend to be avoided because confrontation is not fun. But if we build a culture of feedback, then we can open the door for otherwise challenging conversations to become normative.

  • Focus on betterment of the team. Be collaborative and show how this is necessary for everyone.

  • Remember that emotions are contagious. More important than the words you choose is how you deliver them. Your energy is everything. So if you're angry or judgmental, your employee will feel that and not hear you. Mind your emotions.

  • Have conversations more often. It's never easy to share difficult information, but if you've developed a rapport with your direct report, it can make the conversation easier. Set regular one-on-one conversations with each of your team members so communication on a regular basis is less awkward.

  • Unless it’s a quick chat, you should almost always find a witness to be present. This is even more necessary when it comes to dealing with policy violations, behavioral issues or anything that may require discipline. Your HR representative can be used as a third-party witness. If that person is unavailable, consider using another manager of the team or an HR liaison. Never involve another employee. Your third party should be briefed on the situation to ensure that you’re both clear about each other’s roles and responsibilities during the meeting.

  • Be consistent. Hold all your employees accountable to the same performance expectations. Have the same dialogue with anyone who is slipping. You don’t want to make it seem like you’re favoring one over another.

  • Keep it confidential. You want to be as judicial as possible when addressing conflicts between employees. Any employees who aren’t involved shouldn’t be aware of the situation. If employees come to you “confidentially,” make sure they understand you cannot guarantee 100 percent confidentiality. Depending on what they disclose, you may have a responsibility to act or speak to others. Use your employees’ complaints, first-hand accounts from any witnesses, and the facts to determine what actually occurred. Take a step back and understand there’s more than one side to every story. Tell your employees you’ve received feedback regarding their offensive behavior. Leave it general to protect everyone involved. There are always three sides to these situations: the employee who complained, the employee who was complained about, and the truth.

You can’t avoid difficult conversations, but the success of your leadership will often hinge on how you handle them. You can do better and help others better in difficult times.

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