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Crucial Conversations for Mastering Dialogue

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,

You can learn more insights and skills like this in Crucial Conversations for Mastering Dialogue

11 thoughts on “Uncomfortable Conversations with a Coworker”

  1. Joel Hasenwinkel

    I am a crucial conversations convert and recognize that the journey for appropriate conversations will never end. In the article regarding the poor communications between co-workers, I was surprised that the role of the boss as a mentor was not addressed. At the very least, there should be a conversation with the boss to apologize for the conflict that has been created and to seek input. Bosses have much more insight than their team members may recognize. As a “boss”, I have a huge amount of respect for my team members that share their areas for opportunity and seek my guidance or assistance.

  2. D. Hilliard

    I am frustrated with Frustrated’s letter. I am currently in the position that he has put his coworker in – a hostle working environment. In my situation I reached out to my confrontational coworker only to be met with more aggression. I finally turned to management and then to our HR department for help. I hope that Frustrated realizes that you simply cannot bully your peers at work. Take responsibility for your actions…shame on you for being frustrated with your coworker for not wanting to talk with you…you created the mess. Kudos to Al for addressing the aggressor’s behavior rather than the victim.

  3. Grizzly Bear Mom

    As a boss I made a point of nipping conflict, tribal politics, and nasty competition in the bud because they waste energy that should be invested in delivering results to customers. For this reason I am surprised that you boss would listen to one sided stories, and not refer your co-worker back to you or call you into the office. If you are really in the wrong, accept responsibility, repent and redress the person. Tell your superivsor that you did so. Then work on BOTH relationships. It may be that your co-worker has undermined your relationship with your boss. I had a co-worker who continaully undermined my projects until I realized that I needed to be three months ahead of her thinking.

  4. Jim Anderson

    Great response Al! By your not making assumptions of Frustrated’s situation, you gave all of us more broadly applicable ideas. Each of us can be misunderstood by others and that can escalate if we don’t handle it well early… and handling conflict well is no small feat.

  5. Christina Medvescek

    I’m a vice president in a national nonprofit. I would like to suggest that in the Analysis and Preparation steps it’s important to clearly define what you want. I’ve found difficult conversations are easier if I’m clear in my own mind exactly what I want to have happen and why, because it allows me to be clearer and less confrontational with the other person. It also allows me to see when the other person is giving me what I want and to accept it. Sometimes, gaining this clarity helps me see that the conversation really isn’t about what I thought it was about.

    The key is to be specific. For example, if someone is hard to work with, what specifically do you want them to do or not to do? If you are trying to accomplish a goal that seems to be at cross purposes with the other person, what is the essence of your goal? (I.e., “I propose doing things in this fashion because I want to finish the job in the least amount of time.”)

    If you’re having trouble getting to the heart of what you want, ask yourself this question: If I get what I want, what will I have? For example, perhaps you want your coworker to talk to you first before she talks to your boss. If she does that, how will that make things better for you? (i.e., you’ll more control or more flexibility or the problem will be solved quicker, etc.) The answer to that second question brings you closer to what you really want, and helps you make your goal clearer to your coworker.

    If you’re familiar with I Messages, the Analysis and Preparation stages are an excellent time to write out a few relating to your specific problem.

    (Short review of I Messages: I feel [blank] when [description of the problem] because I want/need [blank].)

    Don’t be afraid to share your honest feelings. I’ve had great success when I admit I’m “scared” or “embarrassed” or “confused.” And be sure the want/need part is very specific.

    Best of luck! Chris

  6. Kim

    I agree with the last reply made on finding out what it is that you want, and what it will do for you once you figure it out, plus what do you want to see accomplished.
    I have somewhat of the same situation as frustrated; however, I’m the coworker that doesn’t get along with Team lead. After working for this company for almost 4 years, I decided that different actions needed to be taken, so I asked our manager a couple of times this year, if I could meet with him and discuss these situations.
    My situation with Team lead is (she leaves me out) of team ideas, or problems, basically (information) rather, learning, good bad. Rephrase that; for the most part, I am informed, but there are lots of things done under the table that can’t be seen only by the three and not the four of us. I can’t prove it, however, when I starting working for this company, my team lead and I got along very well, and I was the inside person, instead of the outside person( which is where I’m at now, therefore, I know that the “under table” stuff is going on.
    I was not trained correctly, and left a lot at times to my self to not know what I was doing, and my team lead made it difficult to go to her for help, so I had to learn a lot on my own, as well as be rained from someone that did not know much about the job as well.
    This left many days weeks, months very long for me, and I had no one to turn to. However, after bitterness washed away, and my job became easier, I decided that it was time to let my Manager know what had happened my first year working for this company.
    Some may say why bring up the past, well I say, when the past is still very much in the future, then it has a lot to do with it. Now, things are getting a little better, but the main thing everyone has to realize.
    The manager will never, address his team lead around you, or let you know in any way that they were wrong, they will always be on there side no matter what, that’s what makes it more difficult, so my advise is…get everything out now. Don’t wait, keep notes on everything, emails time dates etc. It has helped me to some degree, I may never know what our Manager said to my team lead, but I know by her actions now that she was addressed, as I said things are a little better…but there will always still be something.

    Best of Luck to us all.

  7. MissPriss

    Reading this brings back memories of my past, present, and future I am sure because every work environment has these issues weather it someone bringing the negative in from home, or they just have and antigonistic personality. I have been on both sides of this situation. I am very direct so people take me in the wrong way all the time even thought I am really sensative. We only let our co-workers see a small portion of who we are even though we think we know them because the massive amount of time that we spend in each other company. I think that we need to be tolerant of each other and not jump to conclusions about reactions to situations. Once it is broken Al is right you need to find a way to fix it or the manager has no hope of keeping the team together. It is shame that the manager has not stepped in if this has been going back and forth between these co-workers for over a year. I hope “frustrated” figures out to let go of the anger before they have the curcial conversation because that will be the only thing the other party heres. That can be the biggest set back in mending a broken relationship. Words only go so far if your actions say you still have a problem, then no amount of talking or intervention from managment will fix the frustrated feeling. Our emotions play a huge role on our actions and without getting over them nothing will get any better.

  8. Speedy

    Well. I’m in the same boat frustrated with a co-worker that is intelligent and very knowledgeable unfortunately He does not know how to multitask or prioritize the work load, to close his flaws he is extremely slow, I have approached him several times with ideas and creative schedule handling and at the end I fell that I’m carrying part of his work load. I understand if one fell sick or other situations but how long till He change ??? We don’t have a good relationship and at times is very hard to communicate he also feel s that what he does is right, definitely management need to get involve to mend the situation I can’t and already give up my current approach is a Team with a short leg.

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  10. Bruce Wilkinson

    It feels like the boss is a pivotal figure in this dialog. When a manager permits a triangulation to occur, it both rewards the complainer for not resolving the problem with the coworker and creates a barrier to constructive dialog between the employees. By acknowledging his majority contribution to the problem, Frustrated is signaling a desire to work things out. While it is understandable that the coworker is more comfortable discussing a coworker’s behavior with the boss, it is a manager’s responsibility to expect that all employees have the courage to engage in crucial conversations to the benefit of the team and getting work done. While we often make a cultural judgment that a victim has the moral high ground, both “professional victims” and “perennial perpetrators” are a liability to a productive workplace. I have seen the professional victim scenario play out frequently with less productive employees who play the victim and use a form of moral jujitsu on managers and assertively productive coworkers to avoid confronting a deficiency in productivity. There is no evidence of this in the situation above but some of the follow up comments remind me of instances where any attempt at prodding an employee or coworker to improve performance is interpreted as aggression and evokes a “victim” response. Just because Frustrated has the integrity to admit fault, it would be an unwarranted assumption that the coworker in this scenario is blameless. Since the manager has been involved in this case, he/she needs to create the opportunity for a transparent dialog to occur that allows Frustrated to own his fault in previous encounters, for game-playing, if any, on the part of the “victim” to be exposed, and also to create an expectation for how future communications will be conducted.

  11. Bruce Wilkinson

    I also want to seed a response to the coworker’s brushing off an attempt at a crucial conversation by claiming that “it’s no big deal.” It is always a big deal when a complaint is lodged with a boss or with HR. In a workplace, people have to work together–which means working things out–particularly things that are serious enough to involve an authority figure.

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