Difficult Conversations with a Colleague and Friend

How do you raise a sensitive issue about their inappropriate behaviour of a colleague who’s also a friend without feeling like you’ve put them on the spot and without losing their trust and friendship? I answer this dilemma in the post, so read on..

Do I? Don’t I?

Many people think that raising these sensitive issues are problematic and should be avoided, but I say not raising them is even more problematic. Here’s how to do it in a way that doesn’t jeopardise the friendship but at the same time keeps things on a professional level.

“Todd, I want to talk to you about something you said relating to how I manage the team, you said it when we were sitting at the bar together with the rest team at the end of the final away day, remember?”

“It left me feeling uncomfortable and concerned and I wanted to raise it while it’s still fresh in our minds, you ok to do that?”

“I’ve been putting it off because I wasn’t really sure how to raise it with you given we’ve got such a good friendship and I’ve been wanting to find a way of raising it that, on the one hand, didn’t jeopardise our friendship but on the other made sure that my professionalism and accountability doesn’t come into question.”

“So I want you to know that I’m raising this issue because it’s important to me. Do you have any concerns about me raising it in this way?”

“I thought I’d start by recalling the conversation as I heard it, and then get your reaction to that. There’s a chance that you recall it differently and if so I’d be curious to know how you see it.”

“I also want to share why what I heard you say is a concern to me and what I’d like to do to rectify the situation”

“Does that sound ok to you?”

You’ll notice in this conversation starter, that I’m constantly checking in with my colleague, I’m breaking it down into small steps and gaining agreement along the way, I’m also reassuring my colleague that it’s not an easy thing for me to raise this with him but I acknowledge that it’s important for the two of us that I do.

Key Strategies

  1. Advocate and inquire. Don’t just ramble on headlong into an uninterrupted monologue, break the conversation up by checking in and getting agreement with your colleague as you go along.
  2. Share the dilemma that you were faced with when deciding to raise the issue with them and reassure them that it wasn’t an easy decision to make to raise it with them, nevertheless you felt it was important for the benefit of your friendship and working relationship.

Approaching these conversations with a mutual learning mindset will help you raise the issue and create an environment that makes it safe and comfortable to do so.

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