226: How to Prepare for a Difficult Work Conversation

How to Prepare for a Difficult Work Conversation

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Here’s the bad news: You can’t change anyone but yourself.

Here’s the best news ever: You can’t change anyone but yourself.

I don’t know about you, but when I’m about to have a difficult conversation with someone, I tend to imagine all kinds of worst-case scenarios. As a result, I often avoided having those difficult conversations…which meant the situation and my feelings continued to fester.

Today, we’re going to talk about how you can prepare yourself for these difficult conversations to maximize your chances for success.

Reality is often much easier than the story we’ve made up in our heads – all the more reason to not put the conversation off.

When you are having a difficult conversation with someone, you are the only person in that equation that you have any control over. What you think, what you feel, what you say, and what you do.

So how can you show up for this difficult conversation in a way that serves you?

Thoughts about ourselves

Let’s start with the thoughts you have about yourself. For example, you might think:

“I’m not a good enough manager to lead this person.”

“I don’t know how to start this conversation.”

“I don’t know how to help this person.”

Here’s the brain science of what you are thinking: your brain scans the environment for evidence of what you’ve just thought about yourself. If you think you’re not a good enough manager, your brain will look for and present you with evidence that you, in fact, aren’t a good manager.

Your challenge is to notice these thoughts and decide whether you want to continue to think them. Does that thought serve you?

Here are some better-feeling thoughts you might choose instead:

“I have been successful in having difficult conversations before.”

“I’ll figure out a way to start the conversation.”

“I’ll try my best to help this person.” 

Now, your brain is scanning the environment for evidence that you will be able to start the conversation or help the person. Much better.

Thoughts about the other person.

This one is so insidious, because we often think the worst of the other person with no real evidence to back our beliefs up.

We might think:

“He isn’t even trying.”

“She refuses to listen.”

“He thinks he can get away with anything.”

If we think these thoughts, we go into the difficult conversation ready for a fight – we are expecting the worst of the other person. Everything that person says or does is colored by our belief that they aren’t a hard worker, they don’t listen, or they think the rules don’t apply to them.

Here are some better-feeling thoughts you could choose:

“He’s really good at _____.”

“I’ve seen excellent work from her in the past.”

“He may not understand the reason for the rules we have.”

Now you are able to go into that conversation expecting the other person to be open to feedback and wanting to do the best job possible.

Thoughts about the possible outcome.

The biggest hesitation I had about having difficult conversations with my employees is that I thought they would throw my problems back into my face. (I don’t know why I believed that; it had never once happened that way.)

Maybe you are thinking that it won’t make a difference to talk to this person…or that they will just try to undermine your authority.

You might think:

“Nothing will ever change, no matter what I say.”

“They will never admit to what they did.”

“They will just put the blame on someone else.”

Here are some better-feeling thoughts:

“I’m taking a small step towards improving things.”

“I will focus on solutions rather than placing blame.”

“My ultimate goal with this conversation is _____.”

Notice that the first set of thoughts were outward focused…remember, we can’t change anyone else, and it is incredibly disempowering to focus on what someone else is doing wrong.

The second set of thoughts are focused inward…the only part of the equation we can change.


Are you in the wrong job that chips away at you every day? The CareerSpring document and coaching program will help you find a job that uses your zone of genius, recognizes your value, and pays you what you’re worth.

If you’re ready to take your job search to the next level by working with a highly experienced professional with a track record of client success, schedule a complimentary consult to learn more:

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037: The Work Stuff No One Ever Tells You (with Becky Cutright)

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225: Solutions-Focused Questions to Ask Your Direct Reports