July 10

Mastering Tough Conversations in the Workplace: A Step-by-Step Guide for Leaders

Handling tough conversations in the workplace is an essential skill for effective leadership. Whether you need to address performance issues or provide constructive feedback, mastering tough conversations can help you foster a more productive and positive work environment.

In this guide, we’ll explore five key steps to help you navigate these challenging discussions with confidence and care.

My Personal Experience with "The Tough Conversation"

Back when I started my career, back before I became this driven, type-A, and highly disciplined professional I am today, I was actually quite the slouch. Yes, it’s true, I was not exactly the type of employee you would have wanted on your team.

I mean, it was not surprising for me to run a little late to the office, stay a little longer at lunch, and while my work was good most of the time, there was the occasion now and then when, well, let’s just say my work was less than perfect.

Now in fairness, this was my first job out of college, and I was being paid less than any struggling college graduate would need to give up her second job. So given my low level position, and the fact that my work was not that critical to the success of the organization, my boss let my underperformance go most of the time.

Until that day. The day I had been asked to fill in for a higher level team member who was out on maternity leave. I had been told when I took some of her workload how important it was, and that I needed to ensure my work was not only done well, but that I would need to have it double-checked by another team member before considering the task complete.

Unfortunately, I took that last part as a suggestion rather than what it was meant to be – a rule! The result – I ended up making a pretty big mistake that left the CEO of our organization to make a major faux pas in front of about 200 of our top clients. Not a small mistake by any stretch of the imagination.

It was bad, and I was so sure I was going to get fired, that I cleaned out my desk. But instead, my boss called me into his office, and had the tough conversation that completely turned me around.

Here’s How This Tough Conversation Went

“Meridith, I am about to have a tough conversation with you, not because I am mad at you, but because I care about you. You’re a smart, competent woman with a bright future, and I know you can do better. What happened this week with our CEO was some of the worst work I have seen you do, and I know you are capable of better. 
Last week I asked you to take over some job responsibilities because I thought you were ready and up to the task. I still do, so I am not sure what went wrong. Why don’t you tell me?”

I sat there in silence, so he continued.

“Well, Meridith, why don’t you take the time, a day or so, and think about what went wrong, and decide if you think you are up to the task. Also, come back and share with me how you could have handled things differently and how you will handle things differently going forward. 
Again, I believe in you, I do think you are smart, capable, and more than up for the job. But unfortunately, whether you are or whether you aren't isn’t up to me – it’s up to you. So let’s meet back in my office in two days, and you can share with me what you want.”

That tough conversation was more than thirty years ago, and I still remember it. It was such a turning point for me, because he made me own what had happened and empowered me to turn things around.

So how did he do it?

Here are the five steps to mastering tough conversations in the workplace and give you the tools you need to follow to have the same impact on your employees.

5 Steps To Mastering Tough Conversations in the Workplace


First and foremost, show them that you care. Believe that you are not doing this to hurt them, but because you want to see them grow, develop, and get better. And because that’s your job as the leader.

Explain Why

The reason you have the tough conversation should not be all about you or the organization. You need to explain the why for the team member. My boss could have easily made our conversation about the CEO and how I embarrassed him, but he didn’t. Oh, he mentioned it, when he pointed out my challenges, but he focused on how he believed I could do better.

Be Clear

And direct, and in fact be ready with examples. If you are going to have a tough conversation, you need to ensure the team member you are talking with has no questions left about what they’ve done and why you are disappointed.

Create a Path

Tough conversations should result in a set of expectations of what you want and expect to see differently – behaviors and results. So lay those things out, and ask the team member to create a path. In other words, how and what they are going to do differently to achieve that goal.

Let It Go

Then accept the fact that your team member may turn it around, and they may not. But the toughest part of tough conversations is that you don’t control. You have to let them decide whether they want to improve or not

Having tough conversations is never easy. But helping our team members improve is not only our job as leaders, but ensures we are doing what is best for everyone involved.


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