Annoyed? How To Make Difficult Conversations Suck Less

Difficult conversations suck.

No one likes them, and yet they are a part of life.

If you have ever or will ever interact with other humans, at some point you are going be involved in a difficult conversation.  Even though it is very tempting to avoid addressing issues, ignoring the situation doesn't help anyone.

So instead of sticking your head in the sand, let's figure out some easy steps you can take to feel more comfortable.



Today, we’re going to talk about difficult conversations.

You know the ones that start with “Could you come into my office? Close the door behind you, okay?”

I’ve had possibly thousands of these. I’ve definitely had hundreds. They’re never easy, nor should they be easy if you are a kind, considerate person who is worried about other people’s feelings.

But they are necessary, and that’s part of being an owner or a manager.

You need to put on your big boy, big girl pants and have the conversation. What I want to talk about today is how you can psych yourself up for these difficult conversations.

If you’re on the fence about firing someone, I encourage you to check out my free Reframing Firing course because that will help you flip your script on that and see it in a new way that will make you realize, “Oh my gosh! It’s not such a terrible thing to do to someone.” Sometimes you need to do it for them because they would be happier somewhere else.

But today we’re just going to talk about difficult conversations, where you need to address an under-performing employee or an under-performing vendor, whatever it is.


What I do to get ready for these situations is I map out what I want to make sure I cover – so that is my concern – I have some specific examples of when I noticed the behavior or where the behavior or the expectations aren’t being met, and I have really clear examples.

So when I say, “You know, you’ve demonstrated a bad attitude,” but they say, “When have I ever had a bad attitude?” I can say, “Well on Tuesday afternoon in the meeting…” I want to be able to have concrete, actual things to share with them so that they have an example of how they’ve exhibited that behavior.

I make sure I’m prepared, and I kind of script it out in my head. Some people actually physically write it out. I don’t need to do that at this point, but that might work for you. I basically just think about how I’m going to address it, and I do usually like to start with something warm and fuzzy – unless I’m pissed off and I want to be done with them. Then I’m just going right to the “You gotta improve or we gotta move on” thing.


Most of the time, I like to go into it and say, “Hey, you know, I just wanted to call you in here. I’ve noticed this over the past week or so, and I wanted to talk about it before it became a bigger deal, blah, blah, blah,” and then you share the concern. You bring it up, and it’s sort of a casual bringing up.

It’s sort of like your check in, which I talk about in a different blog and video, but it’s a way to say “I’ve noticed your behavior not being acceptable, and I need you to make a change about it.”

One of the best ways to start that conversation is “I’ve noticed…” and then they can respond to it.

Don’t get upset if they get all pissed off and they’re like “Waah, waah, waah”, whatever.

People are going to get their feelings hurt, and they’re going to be embarrassed and all sorts of things are going to come up, and they’re not going to handle it in the best way.

That’s just life. That’s the reality of it.

We can’t expect them to be like magnanimous and gracious all the time.

If they’re a complete jerkwad, well then you need to address that.

But for the most part, people are going to have a little flare up of emotion, and then they’re going to come down. In my case, they almost always cry. I don’t know why that is, but they do, so then I just hand them the box of Kleenex, and they can deal with it.

Then we can start talking about what the issue is because lots of times they’re not performing for a reason.

It might be that they’re not trained, they have some questions, or it might be that they’re in the middle of a divorce, and they haven’t told anyone. Whatever it is, you’re at least starting the dialog.

If they’re a jerk the whole time, you now know, here’s the deal. We need to start replacing this person because they’re not coming back from this. Now we’re moving into a performance improvement plan, and at the end of this, they’re likely not going to work here any more.

But if you don’t address it, you can’t have any idea how they’re going to react to it.

Again, if they’re momentarily flustered and startled, don’t judge them harshly for that. But if they maintain it for three minutes and more, then that’s probably just that they’re a weird duck and you should try to move on in your life.

Anyway, those are two ways I prepare myself for difficult conversations.

I also look at “How would I feel about it if I was in their shoes? Would I want to have a job that I’m not successful at? Would I want to have a boss who almost doesn’t like me because I can’t do the job? Do I want to be the co-worker nobody wants to be partnered with because I don’t get it?”


I wouldn’t want to be that person and I wouldn’t want to be in that situation.

So, if I liked them enough to hire them, I certainly like them enough to set them up for success.

It’s always going to be difficult, unfortunately, but just know that if you’re prepared and you’ve thought about what you’re going to say and you address it in a way that opens conversation and dialogue, you’re going to get much better results than never addressing it at all or waiting to address until you’re pissed off and you blow your top, because that doesn’t work well at all, either.

I hope this helps!

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