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Time for a Difficult Workplace Conversation? Four Steps to Make It Easier


By Jean Kelley

No matter what your profession or level in your company, at some point, you’re going to have to initiate a “difficult conversation” with a boss, co-worker or colleague. This could be between you and one person, or between you and an entire group. It’s a conversation in which each party has an opinion and perspective, and they’re all very different.

So what makes these conversations so difficult? Often, they’re emotionally charged, and because of this, people have a tendency to react rather than respond. Or maybe someone feels verbally attacked and his fight or flight response kicks in, which escalates the conversation and immediately makes it complex. Examples of difficult work conversations include:

  • Talking to a co-worker about a problem he has that’s impacting your work
  • Giving the boss feedback when he’s doing something you don’t like or that’s de-motivating you
  • Critiquing a colleague
  • Talking to a team member who’s not keeping up his end of the bargain
  • Confronting a co-worker or colleague about blatantly “bad” behavior, such as stealing sales or discrimination
  • Pointing out someone’s shortcomings that are affecting the project or team

The list is virtually endless. Regardless of the topic or circumstances, these conversations are hard to initiate, especially when the stakes are high or you’re confronting someone you genuinely like. But the discussion must take place if you want to achieve any sort of happiness and satisfaction at work.

Unfortunately, most people avoid these conversations completely. They tell themselves the situation will improve or the other person will change his behaviors, but that simply doesn’t happen. Other times, people face the prospect of a difficult conversation head on, but then approach it the wrong way, escalating the situation to a standoff.

A better option is to learn the skills needed to have these difficult conversations and facilitate the dialogue with grace and tact. Realize that having these discussions is indeed your job. It’s not your boss’s responsibility to intervene and solve all your problems. That’s called triangulation.

If you constantly go to your boss to smooth over your problems and professional relationships, you’ll never be viewed as a leader in your company. Additionally, by your boss having the conversation for you, the situation will usually get worse. So go to your boss for help with the skills needed to have a difficult conversation, but then engage in the conversation on your own. Always remember that if there’s something bugging you at work, it’s your problem, so take care of it.

Chances are that a difficult conversation is looming in your future. To make the most of it and ensure it goes as smoothly as possible, keep the following suggestions in mind.

Decide To Do It

Having the difficult conversation is for you, not the other person. You initiate it so you can lighten your own load and ease your mind or frustrations. Yes, you know the other person might get defensive, but that’s OK. You have something to say, so you must say it.

Unfortunately, when a situation arises, people tend to fall into one of two categories: silence or violence (verbal). Most people become silent. They understate the problem, avoid it, or make excuses for it so they don’t have to address it. Other people come from an angry place and become controlling, coercing and blaming.

But to be successful in business and in life, you have to acknowledge that it’s time to have a difficult conversation with someone―and then commit to doing it. No backing out, no making excuses, and no yelling. So make the decision and stick with it.

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