Complicated Conversations: 5 Keys to Navigating Tricky Communication 

It can be hard to believe when you are embroiled in a heated or awkward discussion, but those difficult conversations are often highly meaningful. They offer you an opportunity to clear confusion, right wrongs, build trust, fix mistakes, and strengthen everything from relationships to performance. 

Yet, too many people—and leaders specifically—avoid difficult conversations. Even the strongest leaders and best communicators have trouble addressing specific topics in face-to-face situations. One thing we can say with certainty, ignoring the problem almost never works. Things don’t have a way of working out on their own. It’s absolutely critical for you to step up when issues are damaging morale, teamwork, productivity or the bottom line—even when it might anger or upset the other person. 

To make the best out of a tricky situation, follow this advice: 

Process before you do anything else 

Understand the reasons for the conversation. Why must it take place now? For example, is an employee’s frequent mistakes costing the company time and money? Or is a teammate’s attitude during meetings affecting collaboration? Think about what could happen—the worst-case scenario—if you don’t address the issue quickly. Understanding the severity of the issue will help you push through the challenge. 

Then reflect on your actions so far. If you have brought the issue to them before, they shouldn’t be shocked, but if you have ignored it up until this point, expect some confusion. If you have condoned similar behavior in the past, expect them to be angry. If you have led them to believe everything is hunky-dory, they may even be hurt. Understand the role you have played up until this point. Then imagine how the other person will react and prepare yourself.

Establish goals for the conversation 

Before you meet with the person, outline what you hope will happen as a result of the conversation. What are your expectations or goals for the person? Be prepared to clearly describe the issue, but more than that, you must spell out in no uncertain terms what you expect the person to do going forward. And what will happen if the person fails to do so. 

Don’t forget to establish goals for yourself. You will need to monitor the issue going forward—and step in if the other person doesn’t live up to expectations. For leaders, that could mean disciplinary action. Make sure you follow through, otherwise, the behavior likely won’t change. Worse, when other people see it go unchecked, it could spread. 

Have positive intentions 

These conversations should have one goal: to make things better for all involved people. If your intent is to criticize, put somebody “in his/her place,” or get payback, revisit your reasons for the conversation. The discussion should be about moving the two of you in a more positive direction.

Remain respectful, keep your attitude and temper in check, and focus on solving the problem, rather than criticizing and pointing fingers. 

Listen as much—or more—than you talk 

Don’t assume people’s actions are intentional or even that they know they are doing anything wrong. Instead, get some clarity first by asking questions, and listen carefully. You may learn something you didn’t know before that could change your point of view.

Then present the issue as clearly as possible, and invite the person to respond, sharing their own views of the situation. It’s important that the conversation is two-way and that you both have an opportunity to share your perspective. If you do all the talking, and don’t give the other person a chance to respond, it will feel like a lecture or scolding, and likely, much won’t change. 

Lastly, and this is important, if as you’re talking the other person says something that angers you, pause, and be thoughtful in your response. It’s really easy to lose control in the heat of the moment, but if you do it could exacerbate and deepen the conflict between the two of you. 

End with a plan 

Once you have both had an opportunity to talk through the issue, agree on the next steps. Decide together, how you will move forward and who is responsible for what. Then end with some optimism. Say something like “I really appreciate you talking with me today. I believe you will make these changes, and I am confident we will not need to have this conversation again.” It can go a long way toward showing the person you are ready to put the issue you behind you. 

Looking for guidance on handling your trickiest leadership challenges? We’d love to help! Contact us today to schedule your first consultation. 


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