Many successful organizations accomplish this regularly. But it’s no surprise that it’s a challenge for many others. In fact, some organizations are quite far from achieving their mission-critical goals. That typically creates stress, or worse, as managers try to assess what is amiss and how to fix it, leading to difficult conversations. No surprise: Most of us struggle when we must respond to workplace drama. It’s not a naturally pleasant interaction. But it does not have to be acrimonious or unproductive. Avoiding 10 common mistakes below will save you from some angst and extra effort.

Difficult Conversations: Mistakes to Avoid

• Putting off or never having the conversation. When you become a manager, you say yes to more responsibility. You also say yes to navigating difficult conversations—about performance or behavior problems, misaligned expectations, and personality conflicts. As an individual contributor, you may have purposely steered clear of such talks. Those days are over. There’s just no avoiding the fact that avoidance is a lousy management technique.
• Softening or burying your message. Once you decide to initiate a difficult conversation, one you plan or one initiated by someone else, it may be tempting to offset difficult truths with praise or good news. This is just another form of avoidance and can backfire. There’s a real chance your message won’t get across or will be misinterpreted. And that sets the stage for an even more difficult conversation in the future. Straightforward, calm, and open-minded is usually a better approach.
• Losing sight of the conversation’s purpose. No one wants to get through a challenging, emotionally draining talk only to wonder what just happened and why. You can avoid this result by identifying what you want to get out of the conversation. Your goal might be to learn more about someone else’s point of view, to express a view of your own, to deliver bad news, to arrive at a solution to a sticky problem, or something else. Whatever your purpose, if you’re clear about it ahead of time, you can steer the conversation toward your goal.
• Backpedaling to avoid more conflict. Sometimes in difficult conversations you discover something that changes everything. Let’s say a team member has been slacking off, and when you ask what’s going on, they reveal that their spouse just filed for divorce. In such instances, adjusting your approach to accommodate the new information is completely appropriate. Other times, however, when a conversation gets uncomfortable, managers find themselves giving someone an undeserved second chance or making concessions that could hurt their team or organization. This may feel good in the moment, but will probably be counterproductive long term.
• Ignoring or suppressing feelings central to the conversation. There’s an old saying that it’s best to check your emotions at the door. But is this realistic? And what if those emotions are central to a workplace problem? It’s true that you don’t want to be an emotional wreck during difficult conversations. But ignoring what you and others are feeling can lead you away from the truth—and away from the messages and solutions you should be exploring most. You can calmly describe what you’re feeling without blaming or attacking others. For example: “It’s upsetting to me when you ask for my input and then ignore it,” versus “It’s rude of you to ignore my input.”
• Seeking validation of assumptions instead of deeper understanding. We often head into difficult conversations with intentions and beliefs. This is a typical human response. It can also become dangerous if you get so attached to these assumptions that you focus on proving that you are right, instead of understanding the situation. Is it really true that one of your team members is “just lazy,” or that your boss has it in for you? There’s usually a lot more going on than meets the eye—within others as well as yourself.
• Exaggerating. “They never listen to me.” “The entire project was a disaster.” “My manager always makes me feel like a failure.” When a situation gets tense or emotional, you might find yourself falling back on sweeping generalizations and exaggerations—in part because people tend to overemphasize negative events. Doing so might feel good in the moment, but exaggerations are inaccurate and unfair, and typically tend to escalate conflicts. It’s best to stay focused on specific situations and facts.
• Failing to account for cultural or other types of differences. Could a team member’s unwillingness to give you feedback be based on different cultural values about responding to authority? Is it possible that complaints about a team member’s formality in conversation stem from an unreasonable intolerance? Is a generational disconnect the real culprit behind frequent disagreements between a younger and older colleague? As a manager, it’s your job to cultivate an awareness of differences that could be based on race, ethnicity, gender, or age—and then factor in these differences before jumping to conclusions.
• Filling in uncomfortable silences. It’s easy to talk yourself into a corner when you’re nervous. If there’s a pause after you ask a tough question, or an awkward moment, wait it out rather than ramble. Take a deep breath and see if the other person fills the silence. Listen. You might be surprised by what you learn.
• Proper preparation. You prepare for interviews with job candidates, for team meetings, and weekly status updates. Why wouldn’t you properly prepare for a conversation that will be tougher than any of these? Equally important: Don’t take your preparation too far. You’re getting ready for a conversation, not a performance. There will always be elements—weird tangents, unexpected admissions, emotional outbursts—beyond your control. Be accepting of these wildcards because they often indicate how others really think and feel. If the situation gets too intense, you can suggest taking a break.

How to Initiate a Difficult Conversation You’ve Been Putting Off

Why do it?

Challenging situations—from underperforming team members to angry colleagues, to tough news that needs to be shared—often get even more difficult when you avoid them. Besides, the reality of a difficult conversation is rarely as unpleasant as the worst-case scenarios you envisioned. Won’t it be a relief to let go of all the dread, stress, and worry that’s been occupying your mind?

How to do it:

• Define—and write down—specific goals for the conversation. The main pitfall to avoid is walking in not knowing what you want to get out of the conversation. Start by asking yourself these key questions:
  • What is the single most important reason this conversation is necessary?
  • How can this conversation benefit me, the other person, and my team and/or organization?
  • Is what I want to get out of this conversation realistic?
• Craft a direct and measured opening for the conversation. Oftentimes, the most daunting part of a difficult conversation is the beginning, so put some prep time into what you’ll say first. It can be tempting to start off by easing tension, but if you don’t approach the conversation in a direct way, you run the risk of confusing the other person or making them feel manipulated. Once you’ve crafted it, practice your opener aloud in front of a mirror, or with a friend or mentor.
• Ask the person or people involved if they can chat, or send a meeting request. In approaching the other person or people involved, it’s usually best to avoid mysterious requests, which can create anxiety (especially in team members). Try a simple, straightforward approach. For example, if a team member hasn’t been responding promptly to customer emails, you could send this message: “Samir, do you have 30 minutes today or tomorrow to talk about a concern of mine regarding handling customer emails?”
• Have the conversation—and follow up. For the conversation itself, remember that it’s a dialogue, not a monologue—what the other person has to say is important. End the conversation by recapping any action steps and thanking the person. Then, even if the conversation goes remarkably well, schedule reminders in your calendar to check in with the other person. And do it. If you’ve taken the initiative to have a difficult conversation, make sure it was not an exercise in futility.

Following Up After a Difficult Conversation

When emotions are running high, it’s easy for a team member to misinterpret the things you say or focus only on certain parts of the conversation. And no matter how carefully you prepare your feedback, it can be tough to articulate your message clearly during a difficult conversation. Sharing the main points in writing afterward can help clarify for your team member (and serve as a record for you) what needs to happen next.

How to do it:

• Determine the conversation’s objective and key messages ahead of time. You’re much more likely to be able to communicate clearly and stick to your main points if you’ve mapped out what you want to say.
• Immediately after the conversation, write down what was said and agreed upon. Because the conversation probably won’t go exactly as you planned or may have been initiated by someone else, it’s wise to write down exactly what happened. Documenting the conversation will help you share the key points with your team member and will be a written record in case you face a similar situation again, or need to escalate an issue to your manager or HR.
• Within 24 hours of your conversation, share the key points with your team member. Include in your conversation recap:
  • A thank you to your team member for having the conversation with you.
  • The main messages you conveyed in the conversation.
  • The main messages you heard your team member convey in the conversation.
  • Specific actions that you are committing to doing going forward.
  • Specific expectations that you have of your team member going forward.
  • A restatement of any deadlines or deliverables you agreed upon.
• End your recap with an invitation for your team member to give input and ask questions. Just because you’re sending a recap doesn’t mean the conversation is over. You want to give your team member the opportunity to question any points they remember differently, add details you missed, or clarify their own perspective (they may not have communicated clearly in the moment). Then, of course, move forward with and follow up on action items.

Role-Play a Difficult Conversation With a Mentor or Trusted Friend

Why do it?

Role-playing is a low-stakes way to practice what you want to say so you have a better chance of getting your message across—even when emotions are running high. Saying the words out loud can reveal what feels natural to you, what feels forced, and where you may stumble. Practicing with someone can help you anticipate and work through the other person’s reactions—and learn how you come across as you speak, listen, and respond. In the end, you’ll feel less anxious and more confident that your upcoming difficult conversation will also be a productive one.

How to do it:

• Think through what you want to say—and how the other person might react. As part of your planning, answer these questions:
  • What’s my most important reason for having this conversation? What outcome do I want?
  • What good outcome do I want for the other person?
  • What are the main points I want to make in the conversation? What questions do I want to ask?
  • What reactions (positive and negative) is the person likely to have? How might I respond?
• Ask a mentor or friend to role-play the conversation with you. Be sure to ask someone who is not close to the particular situation you want to role-play.
  
  You could say: “I need to have a difficult conversation with my teammate, and I’m trying to plan what I’m going to say. Would you be willing to sit down with me later this week to role-play some scenarios?” If your difficult conversation is scheduled over video, plan to role-play over video as well so your partner can give you feedback about how you come across on camera.
• Role-play the conversation a few times and ask your partner to respond with various emotional reactions. As you role-play, practice using language that is clear and specific, and shows that you’re listening to your partner’s reactions.
  
  For example:
  • “I noticed ___. The impact of that is ___.”
  • “What are some ideas for how we can improve this going forward?”
  • “I hear you saying ___. Do I have that right?”
  Note your emotional reactions to your partner’s statements and what triggers them. Being aware of these triggers during the actual conversation may help you stay calm.
• After role-playing, ask your partner for feedback on how you came across as you spoke, listened, and responded. As with any time you ask for feedback, the more specific you can be, the better.
  
  For example:
  • “Any tips for how to improve my eye contact, body language, and tone of voice?”
  • “How did I do when it came to listening?”
  • “Is there anything you suggest I say differently?”

Navigating a Difficult Conversation

In summary, if you need to initiate a difficult conversation, it’s important not to delay it because of trepidation. When having a difficult conversation, be careful not to overly soften your message because you don’t want to hurt the feelings of the team member with whom you are speaking. Be cautious and thoughtful with the words you choose so you don’t inadvertently exaggerate. Also be careful not to fill uncomfortable silences, which could lead you to say something unintended.