How to Successfully Engage in Difficult Conversations

A common struggle for new leaders comes in the form of the dreaded “difficult conversation.” While difficult conversations can come in a number of forms, there are two common types that develop as the result of being in a leadership role.

  • Delivering information that is difficult for the other person to receive, and
  • Receiving information that is difficult to hear

Delivering Difficult Information

Prior to becoming a leader, few people have to confront poor performance, inappropriate behaviors, poor workplace hygiene, or any number of other touchy and difficult to address topics. Now, in a leadership role, new leaders find themselves forced to confront these issues at least occasionally. The sensitivity of speaking with another person about correcting or changing their behaviors combined with lack of experience handling this type of conversation makes it very uncomfortable for most new leaders.

Here are five tips to make the conversation less difficult…

Make it a conversation.

When you have news to deliver to someone, it’s tempting to just deliver the news without engaging the person. While some situations call more for information delivery than they do for conversation, delivery over conversation is the exception rather than the rule in most leadership situations. Making it a conversation means that you need to ask questions and listen to the answers at least as much as you offer your observations. Do as much as you can to engage the person in a collaborative, problem solving discussion. Check out this resource for powerful tips on coaching and mentoring those around you.

Have the conversation in private.

Do everything within your control to avoid creating embarrassment or “loss of face” for a member of your team. Lots of negative emotional energy is generated in people when they experience either of these two situations. This negative emotional energy will completely block their ability to receive and act on any helpful correction or improvements you offer. In fact, these feelings could create resentment and anger that leads them to justify their previous behaviors and hold on to them more tightly.

“In private” applies to how and when you invite them to the conversation and when you actually have the conversation as much as it does to where you hold the conversation. A public invitation to a private conversation about a difficult subject can create a sense of embarrassment and feeling of disrespect as much as having the actual conversation in public can.

Focus on behaviors and business impact more than on interpretations and feelings.

From a leadership perspective, the point of a “difficult conversation” is to improve the business or the team in some way. While it might involve some discussion about what to correct or change in a person’s behaviors, it’s not really about correcting or changing the person. It’s about improving the business.

Improving the business can include a number of measures or factors: sales numbers, safety statistics, team effectiveness, production quotas, project timelines, and others. When you need to have a difficult conversation with a member of your team, look for a way to connect your conversation to one of these external drivers rather than to who they are as a person. They will likely see your comments as personal no matter how hard you try to make the conversation about business impact. Do everything in your control to keep the conversation about the behaviors and the business rather than on the person and your interpretations of them or their motivations.

Here’s a post that offers more tips on this idea: The Difference Between Passive, Aggressive, and Assertive Communication.

Make the conversation about the future.

Beware of talking too much about the past. What has already happened cannot be changed, and too much time discussing it often starts to feel like an attack rather than a conversation. It’s okay to learn from the past, but you don’t want to live there. As soon as you have set the stage for discussing how things could be better in the future, quit talking about the past.

Make the conversation about improvement more than correction.

This idea is tightly connected to the idea of keeping the conversation on the future. Your goal in having a difficult conversation with someone on your team is to improve the current state and future outcomes more than it is to correct a problem.

If that statement sounds like a matter of word choice rather than substance, it’s not.

It is about word choice, and it is about more than just word choice. It is about how the message is received by the other person. Few people want to be corrected. Many people like to make improvements. To the best of your ability, drive the conversation in the direction of how you do want to see things rather than how you don’t want to see things in the future. For example…

The next time this situation happens, what I would like to see is _____.

Is better than…

Don’t do _____.

Yes, there are exceptions to this “rule.” And, it works more than it doesn’t.

Receiving Difficult Information

When you move into a leadership position, people on your team will have perspectives about your behaviors as well. If you want to build a high performing team, you need to be prepared to hear what they have to say even if — maybe especially if — it hurts a bit to hear it.

To do this well, you need to get yourself in the right frame of mind to respond as positively and proactively as possible. (By that, I mean not defensively or in a way that sounds like you’re justifying your actions.) In my next post, I’ll share some specific tips for receiving feedback from others in a way that preserves and protects your relationship.

Until then, here’s a post by Kevin Eikenberry that will help you receive feedback from others well: How to Be More Open to Change.

About the Author:

Guy Harris is a Certified Human Behavior Specialist, a Master Trainer in the DISC Model of Human Behavior, and a Conflict Resolution Subject Matter Expert.

As a consultant, trainer, and coach, Guy has worked with large and small clients, businesses, not-for-profit organizations, and individuals from Boston to Brisbane and from Ottawa to Orlando. His past clients include: Sun Chemical Co., Ivy Tech Community College, The Good Samaritan Society, Redbox, Purdue University, Delta Career Education, The American Farm Bureau Association, Butler University, Alpha Chi Omega Sorority, Panda Express, and many others.

Guy is the co-author of From Bud to Boss: Secrets to a Successful Transition to Remarkable Leadership, Sell Naked on the Phone, and The Behavior Bucks System. He has been a contributing author, content developer and editor on other books and training materials including: Presenting With Style; Leadership @ Work, Leadership Brief and To The Point, and Leadership: It’s an Inside Job.

Originally published at on July 9, 2015.

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