Managing Tough Conversations: Here’s How to Have “That Talk” You Don’t Want to Have

Editor’s note: This post was originally published on 10/17/17 and has been updated for accuracy and comprehension.

Nobody enjoys having those tough conversations.

You don’t want to be the “bad guy,” and you certainly don’t want to be the one who needs a “talking to.”

But, in your life and in your work, there are times that will require you to manage conversations that aren’t easy to have.

Let’s look at three ways in which your ability to guide communication well will benefit you and the person with whom you’re talking.

1. Counter excuses with data

There’s a clear difference between a reason and an excuse.

When someone is constantly coming to with you excuses about their behavior, it’s time to have one of those difficult conversations.

Gathering data is the best way to bring the situation to light.

Let’s use the example of an employee who is frequently late.

Start keeping a log with dates and times about when this person arrives.

They probably don’t realize how frequently it’s happening, but approaching them with evidence is hard to refute. A pattern of arriving late can’t always be chalked up to “traffic”!

Another great advantage of using data to get to the root of an issue is that it can be done without involving emotion, which is the factor that can make some situations sticky.

2. Disagreeing using “Yes, and” statements

Check out a statement like this one:

Yes, I hear that you feel strongly about that – thank you for helping me to understand your position. And, I’d like to share a different perspective. It’s one that I feel is important for us to discuss.”

The best way to manage a tough conversation is to avoid using words that have negative connotations: but, if, or however.

Saying “Yes” and following it up with a word like “but” negates the positive statement. It can make people feel as if you’re patronizing them and that’s the last thing you want!

Using “Yes, and” statements will let the person you’re talking to know that their voice is heard and considered.


Managing tough conversations ensures that ALL voices are heard and the solution is a true collaboration. #improvtips

3. Agreeing the right way

Do you think there’s a wrong way to agree? Maybe not. But there is a more productive way.

The first part of the equation is aligning your vision.

You and the person you’re working with have to agree to an end goal. Once you get there, you’re able to start the next step: brainstorming.

It’s much easier to generate ideas when you know that you have the same vision for the outcome.

Now you’ve got an end in mind and you’ve got great ideas churning around in your heads.

The next thing to do is to create a timeline together to help you stay on track.

Your timeline should include regularly scheduled meetings so that you’re always on the same page and holds you both accountable to hold up your end.

Case studies

Let’s look at the stories of two leaders who had to have some hard conversations with their employees.

The right language is key

John is a manager of a small sales-consulting firm.

Due to the size of the company, all the employees know each other well, which can be difficult for someone in John’s position when an internal conflict between two associates comes up.

Thomas is a regional sales reps with the responsibility to report weekly updates to John.

Thomas is frequently late turning in his reports.

John was faced with a choice. He could say something like, “Thomas, you’re late again!” which will put Thomas on the defensive and possibly prevent him from hearing what comes next.

Instead, John approached Thomas with language that opened up a conversation:

“Thomas, you and I seem to place different values on deadlines. I’d like to explain why they’re important to me, and then I’d like to hear how you’re looking at them.”

By engaging Thomas in this way, John was able to find out when Thomas was faced with deciding to make a sale or fill out a report, Thomas felt his focus should be on the sale.

Armed with this insight into Thomas’ thinking, John was able to suggest a compromise that allowed Thomas the opportunity to pursue a sale in the way he wanted, while still reporting to John in a timely manner.

Being empathetic

Betty Thompson was no stranger to managing tough conversations in her role as Chief Personnel Officer for a defense and intelligence contracting agency.

Telling someone their position has become irrelevant is always rough, no matter how many times you’ve had to do it.

That’s the situation Betty found herself in.

An employee who had been with the company a long time and who had been successful needed to be eliminated because his job was no longer integral to the company.

Betty took a different approach than Tabatha. She chose to initiate a series of conversations with the employee over a six-month period.

She gave him a chance to share how he thought things were going from his end.

After he spoke, she gave him her perspective.

They kept the conversations going, and by their final conversation, the employee agreed that there was a problem and chose to leave the company on his own.

Betty and the employee were able to leave the situation with a hug and a new perspective for the employee, who understood that Betty cared.

The key for Betty was to approach the topic with compassion and not frustration.  

The results of managing tough conversations

There are some great benefits that come as a result of correctly managing tough conversations. These should motivate you and the other party to have “the talk” as often as necessary.

  • Understanding different perspectives. Each side of a situation gets to share their “side” and feel that they’re being heard. Sometimes disagreements come from a simple misunderstanding. Seeing a scenario through someone else’s eyes is an invaluable skill to have – in work and in life.
  • Everyone becomes a part of the solution. When each person takes ownership, everyone is free to be a part of the solution. Each individual adds their unique perspective.
  • Getting to know coworkers on a deeper level. The collaboration that comes from handling difficult conversations well forges connections between you and the people you work with.

Success = good communication

Your company will benefit from learning how to talk to coworkers, supervisors and everyone in between in a way that doesn’t negate their feelings or viewpoint.

Thriving organizations know how to manage the tough conversations and come out stronger on the other side.

Can you think of an encounter in which these strategies would have been helpful for you? Think of a situation that you’re facing right now in which you can put these strategies to work.

This article is 100% written by a human named Karen Hough. She is the Founder & CEO of ImprovEdge, in the top 4% of women-owned businesses in the US, a 3-time Amazon bestselling author, Yale grad, wife and mom of three.