Crucial Conversations QA

Uncomfortable Conversations with a Coworker

Dear Crucial Skills,

Over the past six months, I have had several confrontations with a coworker. I admit the reasons for the confrontations are mostly my fault. However, instead of approaching me and handling these situations with me, my coworker constantly complains about me to our boss.

I am frustrated that my coworker cannot talk to me about these issues without getting management involved. I want to explain to my coworker that we can talk about our differences directly, but I am afraid I will say or do the wrong thing again and will be back in my boss’s office explaining my behavior. I considered not having this conversation with my coworker, but the situation is growing uncomfortable and makes it very difficult to work together. Can you please share some advice on how to have this conversation with my coworker?


Dear Frustrated,

Many of us can identify with your frustration—and kudos for acknowledging your role in the problem. As you consider your options, it is important to realize that the stakes are high because you and your coworker are interdependent and your boss is now involved. And the same could be said if other coworkers were involved. In either case, someone is put in a position of choosing sides or trying to ignore the situation, and working together becomes more and more difficult.

The difficult and awkward situation you’ve shared here should motivate all of us to have our crucial confrontations or conversations early and with safety. When we don’t hold the conversations or we hold them badly, our relationships and results suffer, just as you are now experiencing.

As I have pondered your situation, I’ve struggled with what to focus on. Your problem is complex, of some duration, and serious, so I’ve been concerned my advice will miss something or oversimplify. With that said, I want to talk about a few steps you might consider.

First, don’t ever consider NOT having the conversation. While this option is tempting, avoiding the problem will not help. Issues will continue to fester and the relationship will continue to sour. So, what steps can you take to ensure the conversation goes well? Here are a few suggestions:

Analyze: I suggest you reflect on the conversations you’ve had with your coworker. Write them down verbatim, to the extent you can remember. When you’ve finished, go back and ask yourself: “What did I do that worked? What did I do that didn’t work? What was I thinking when I said or did that? What intentions or motives were present at the moment when things went wrong?” Such an analysis leads to the next step.

Prepare: Ask yourself a few questions: “What can I do differently next time to make things better? How can I better start the conversation? How can I make it safe for my coworker? How can I deal with the thoughts or emotions I had that were not helpful? What can I say or do differently?” Record your answers, then rehearse the conversation a few times. During this analysis, pinpoint the conversation you need to have.

I’d be willing to bet the conversation you need to hold now is not the conversation you had in the past. It seems like you need to have a conversation about not talking to one another. Plan how you’ll invite your coworker to engage in dialogue with you. Plan the words. Plan where you’ll meet, and plan to keep it private. Also, plan your apology—apologize for what you’ve done in the past and share your intention that you’d like to work this out so you can have a good working relationship moving forward.

Practice: We often practice sales pitches or informational presentations, but we don’t practice some of the conversations that matter most in our lives. After you’ve analyzed what you’ve done in the past and what you will do better in the future, and after you’ve outlined a plan for accomplishing your goals, find a friend—preferably someone who is not on your team at work. This friend should serve as a practice “coach.” Make sure your coach understands the situation and then ask him or her to role play with you various scenarios of the conversation.

What if your coworker says it really isn’t a big deal—but you know better? Practice. What if he or she gets emotional? What if you get emotional? What will you say or do? Practice. When you have practiced holding the conversation well, you will have increased motivation and ability to actually have a conversation that is vital.

Lastly, as a part of your practice, consider your options for if the conversation doesn’t work out as planned. What will you do? Will you ask to have another conversation? Will you ask a third party to mediate your conversation? Will you ask the boss to help? I don’t know what the details are, so I don’t know what your strategy should or will be. But I do know that anticipating and planning for the options can help you make good choices in the heat of a crucial conversation.

So, of the many bits of advice I could have offered, I suggested that you analyze, prepare, and practice. When you do this, you can increase your competence and your confidence.

Best wishes,