My Most Difficult Conversation at Work » Mind Tools Blog
The Most Difficult Conversation I've Ever Had at Work

My Most Difficult Conversation at Work

November 20, 2017

© GettyImages/Grafissimo

“You know what, Simon? I think they should fire you for what you’ve done.”

As conversational gambits go, it was a showstopper. It certainly stopped me in my tracks. I began to panic. I couldn’t talk. I tried to breathe normally. This was going to be a more difficult conversation than I thought.

Introducing Ralph…

It was difficult because of who was saying it. This was Ralph. Ralph was an author of some distinction. He was a big name in his field. He had written several successful and lucrative books for the publishing company I was working for, and he had influence. Influence with my boss, among others. And he knew it.

Ralph had wanted some cartoons included in his newest book. But I knew that including cartoons was a “no-no.” None of the other books in the series had them, and they would have been expensive.

I had told him all this a month previously. Yet he continued to insist that we were going to have them. Not only that, he was having his cartoonist friend draw them up, and he’d be billing my company for the work.

How Not to Have a Difficult Conversation

Now, I’m what you might call a “conflict avoider.” (It’s a nicer term than “coward,” anyway.) I will do everything I can to avoid even minor conflicts at work, and I’ll go several blocks out of my way to duck a full-on row. Ironically, that was part of the reason we’d got to the stage at which Ralph wanted to see me thrown out of the building.

I’d been trying to get out of what I knew would be a difficult conversation with him for so long that I’d managed, through my inaction, to force matters to a head. By the time I’d raised the problem with my manager and got her to confirm that there would be no cartoons, they were already in existence and the cartoonist wanted paying. 

My initial explanation for the mess we now found ourselves in was rambling and disorganized. I tried to break the news while attempting to downplay my responsibility for it. As understanding slowly dawned, however, Ralph’s responses became increasingly blunt. No, he didn’t see why a few drawings couldn’t be added to this one book. No, he wasn’t paying for them. No, he wasn’t accepting my apology. And no, he didn’t understand why I should be continuing in gainful employment.

Aha! A Solution Is at Hand

After what seemed like an hour (but was probably no more than 10 minutes) he finally sneered at me, “Well, what do you suggest then?”

I actually did have a solution to suggest. As Ralph had raged on about my incompetence, thinking aloud about tearing up the contracts he had signed to write further books with my company, enlightenment struck me. He had signed contracts for another couple of books. And one of them was in a series for which the cartoons would be ideal. My salvation could be at hand…

It took an anguished plea to my manager and some flexibility from another editor, but the cartoons did eventually find a home. I’d placated Ralph, and I got to keep my job.

The Consequences of My Inaction

There was a price to pay, however, and some lessons that I needed to learn. I found myself working on lower-profile titles, for a start, and got sent on an assertiveness training course. This seemed like a punishment, but actually it has since turned out to be the biggest positive to come from the whole situation. It enabled me to learn the skills that I needed to handle difficult conversations with even tougher opponents.

But there’s one lesson I didn’t need to go on a course to learn: no matter how difficult a conversation looks to start with, finding reasons not to have it won’t make it get any easier.


What’s the most difficult conversation you’ve had at work? Did you try to avoid it? Or, do you deal with it head-on? Share your story with us in the comments section, below.

4 thoughts on “My Most Difficult Conversation at Work

  1. Anhwar Ashad wrote:

    If things get difficult, it is still important to show positive attitude to make the situation easy and positive as well. Life coaching is also hard but you can learn how to do it in almentor.

    1. Midgie Thompson wrote:

      Great point about keeping a positive attitude throughout the conversation as it may help keep the conversation going smoothly.

  2. james mock wrote:

    just getting along with others and not letting other people in my buisness i worked with many drug addicts people smoking weed on the job and people who had criminal records

    1. Midgie Thompson wrote:

      Having difficult conversations can be tough at the best of times, however having them with people who are under the influence of mind-altering substances (that includes alcohol or any other drug) is even harder. Can HR help and support you to deal with these people who have a mental illness?

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