Difficult conversations are a fact of leadership

If you supervise people, at some point you’ll need to have a tough conversation with someone on your staff.  Done poorly, these discussions can be disastrous.  Done right, you can address the issue, convey the necessary information and maybe even improve the relationship.

What separates difficult conversations that go well from those that don’t? Planning, self-awareness and empathy.

Here’s how I recommend leaders approach difficult conversations.

Clarify your goal

Well before a conversation occurs, you need to know what you hope to get out of it.  What is the purpose of the meeting, and what must you walk away with?  Whether you are seeking a change in behavior, an apology or something else, articulate it and write it on a pad of paper you’ll take into the meeting.  You can be cryptic with your notes if necessary, but you must be clear on the goal if you are to achieve it.

Check your own story at the door

Let’s say Joe has shown up to a weekly meeting 30 minutes late for more than a month.  Not only are you annoyed, but you see that Joe’s regular tardiness is disrupting the team, and hurting progress. When he does arrive, he’s unfocused and doesn’t contribute like he used to.  What’s the deal?

Many of us might let our emotions get the better of us here.  Going into a meeting to address this issue, we might harbor a number of assumptions that color our handling of the situation.  Is Joe disrespectful?  Does he think the meeting is unimportant?  Is he unable to manage his calendar, and might this mean he shouldn’t be trusted with other details?

Notice how this thinking can spiral out of control.  In truth, we know only this: Joe has been late.

Suppose that instead of blowing off the meeting, Joe has been taking his wife for treatment of a newly diagnosed cancer.  His tardiness might still need to be addressed — in a compassionate way, perhaps, like moving the meeting — but his story requires very different handling than the one you might spin by speculating.

Walk in with an open mind, focused only on the facts.  If you ask the right questions, you’ll get the story.  More on that in a moment.

Understand your triggers

Does it bother you when someone doesn’t make eye contact with you?  Do you make assumptions about people when this happens?  That’s a trigger — something that sparks an emotional response and a set of assumptions that might have nothing to do with the intent.

You need to recognize your triggers and the assumptions they prompt you to make because these can easily derail  otherwise constructive communication.  Consider that in some cultures, making eye contact can be a sign of disrespect.  If you know this, while also understanding that poor eye contact is a trigger for you, you are far less likely to let this behavior get in your way.

Similarly, keep in mind anyone you’re talking with has their own triggers.  As you’re talking, if you notice an unexpected change in behavior, you might have hit a trigger.  Pay attention and do your best to understand and mitigate the issue.

Recognize the other perspective

What matters to the person you’re talking with?  You often won’t know, and again, you need to be careful not to spin a story beyond the facts that you have.  Yet, you might have some facts that are useful.

Scour your memory for indicators there might be a personal crisis of some kind, that your subordinate really prizes feeling valued or respected, or anything else that seems important.  You’re not likely to have all the answers, but what you do know will allow you to approach the conversation from a position of empathy.

Remember Joe, who has been late to meetings lately?  To approach his conversation with empathy, you can invite him to tell the story, and help you understand what matters to him.

Hey, Joe. I’ve noticed you’ve been late to our weekly meetings.  I don’t know what’s going on.  Help me understand, and if it’s important that we deal with it, we can.

Expand the pool of meaning

When you invite Joe to add his perspective to what you know, you expand the pool of meaning.  The more you know about what’s really happening, the emotions at play, the driving factors, the more likely you can come to a solution that works for everyone.

How do you approach difficult conversations?

There are many ways to get this right (and wrong).  Please share your experience in the comments!

Last updated December 17, 2018