Tough TalkDecember 16, 2021

How to Have Difficult Conversations Without Damaging Relationships By
December 16, 2021

Tough Talk

How to Have Difficult Conversations Without Damaging Relationships

CIT-June-July-2020-Col4-Studer,Quint-Author-110x140Quint Studer is the author of Wall Street Journal bestseller “The Busy Leader’s Handbook” and a lifelong businessman, entrepreneur and student of leadership. He has worked with individuals at all levels and across a variety of industries to help them become better leaders and create high-performing organizations. To learn more, please visit, and

No one enjoys conflict and confrontation. We all want to be liked and accepted, and very few of us enjoy hurting people’s feelings. Unfortunately, leaders must be able to handle conflict or we’re not doing our job. We need to be able to hold tough and productive conversations with others, and address conflicts inside the organization.

The goal with tough conversations is twofold. One, you want to solve a problem; two, you want to do it without damaging your relationship with the other person. Remember that an organization is simply a network of strong, collaborative, mutually beneficial adult relationships. The better the relationships, the better the company. It benefits all leaders to master the art of resolving conflict while preserving great relationships.

The good news is that tough conversations can actually strengthen relationships and help both parties grow personally and professionally if you handle them the right way.

Before you go into a tough conversation, ask yourself these three questions:

  1. Am I being fair and consistent? It’s important that you don’t have one set of rules for one person and a different set for another.
  2. Am I too focused on being “right?” Just because you may disagree with someone doesn’t mean they are wrong. People have different experiences and points of view.
  3. Do I need to call in a witness, document the conversation, or consider other legalities? If you’re not sure, consult an HR rep or employment attorney.

Read on for some tips for having difficult conversations:

Stay focused on preserving the relationship. It is possible to convey difficult messages while still treating the person with dignity, respect and empathy. This conversation is just one moment in time. If you damage the relationship, you shut down future opportunities for collaboration and innovation. Keeping this in mind should help you stay civil, focused and sensitive to how you say what needs saying.

Consider that you might be wrong. Go in with an open mind. You may not know all the variables causing the person to do the things they’re doing. Often, we hear something totally unexpected that shifts our perspective. We can always be wrong. Knowing this and being willing to admit it is a sign that you’re a strong leader. It will also help you be a better listener.

Before you call the meeting, get clear on what you want to say. Be sure you can express up front what the problem is, how it’s impacting others and what must change. Stick to these points and don’t go off topic. Be prepared with hard metrics if you can: “You missed the sales goals by 37% last quarter” or “You’ve been absent 13 days in the past 6 months.” Productive conversations are grounded in facts, not observations.

Schedule a time to discuss the issue and give the person a fair warning beforehand. Otherwise, it gets blurted out in the moment and results in unfavorable outcomes. For example, say, “Chris, I’d like to chat with you about what happened with the Jones account earlier this week. Can we meet tomorrow morning at 8?” This gives the person a chance to gather their thoughts and prepare emotionally for the meeting.

Meet on neutral ground. It’s usually best not to call the person into your office. This shifts the balance of power to your side and puts the other person on the defensive. It’s better to meet in a conference room or a restaurant. This sends the signal that this is a solutions-centered discussion, not a dressing down from an authority figure.

Seek to be collaborative, not authoritarian. You want the other person to work with you to make things better. Outcomes are so much better when the person feels a sense of ownership for the solution. Ask positive questions like — “How are you feeling about our partnership?” “What factors do you think led to this issue?” Don’t exhibit a “my way or the highway” attitude. It’s good to listen to the other person’s perspective and to compromise when you can. It shows the person you respect and value them. Might doesn’t always mean right, and the loudest voice shouldn’t always win.

When you ask questions, give the person time to gather their thoughts. Don’t just talk to assert your point of view or fill up silence. This comes across as you steamrolling over the other person. This is especially important when you’re dealing with an introvert who needs time to think before they speak.

Listen actively. It’s all too easy to spend your time calculating your response and not really listening. Try to stay focused on understanding what the person is saying, both verbally and nonverbally. Summarize what they are saying and confirm that what you think they said is actually what they meant. Trying to understand where someone is coming from is a way of showing empathy. It helps them accept what you have to say, even if it isn’t what they wanted to hear. When people don’t feel heard or listened to, it damages relationships.

Keep things civil. Never yell, insult, threaten or bully the person. This should go without saying, but we’re all human and emotions can get out of control. If things start to escalate, end the meeting and reschedule when you’re both calmer. A single episode of bad behavior can tear down a relationship that took years to build. The person may appear to comply in the future, but there will be an underlying resentment that affects performance and outcomes. It’s OK to take a break or come back later if you need to calm down.

End with an action item. Ideally, you and the person will both have a task to do going forward. This way you can schedule a follow-up conversation to see if things have changed for the better.

Most people will never enjoy tough conversations, but one can get more comfortable with them. People often find they are the catalyst for growth. They get people unstuck and moving in a positive direction. When one thinks of tough conversations this way, they may feel more inspired to get better and better at having them.   I&FMM 

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