How to Have a Difficult Conversation with Your Boss or Co-Worker

Have you ever wanted or needed to speak with your superior at work regarding a sensitive subject? Maybe you took offense to something that they said or did. Has a fellow team member offended you? Do you feel that someone else on the team is failing to pull their weight?
I think that we have all been there? Even my nineteen-year-old nephew, who was working part-time at one of the Countries most-well-known big box stores, dealt with co-workers who failed to pull their weight. He often shared with our family that some of them, many almost twice his age, sat down most of their shifts and bullied him and other younger workers into doing most of the work. He did not know how to handle the situation and when one of them “put their hand on him” he decided that it was best to quit immediately.
Do you think that he made the best decision? As you can imagine, there are many varying opinions about this situation. It is imperative to handle difficult situations in a manner that preserves relationships when possible and also preserves your employment if the person you need to talk to is on your job.
Today’s post will offer some pointers on how to approach difficult conversations with your boss or a co-worker. And although the focus here is on difficult conversations in the workplace, you will likely find these techniques helpful when you have to have a difficult conversation with a family member, your significant other, or maybe even a friend. Here are my recommended steps to follow when you need to have a difficult conversation with someone: 1) Think before you speak; 2) Make a plan; 3) Know and consider the facts; 4) Be open to a different perspective; 5) Don’t make personal attacks; 6) Maintain your composure; 7) Address the issue; 8) Let it go.
• Think before you speak. I have met many people who pride themselves on speaking their minds. I’m sure the phrase, “Whatever I think, I say,” or “Holding anger in can kill you, so when people make me made, I let them know what I think.” I used to be one of those people. Thank goodness, I have grown and realize that there is a right way and a wrong way to address differences of opinion. I have found that if we would just slow down and think about the fact the we are interacting with another human being could change things for the better from the outset. You see, from the moment that you approach a person, your actions either cause them to become defensive, or to become receptive. As we all know, once a person takes a defensive stance, it is difficult to reason with them. So, if your objective is to have them hear what you have to say, I challenge you to create an environment that will enable the other person to receive what you are saying. Don’t approach the other person in an aggressive manner and don’t place fault. Let them know that you just want them and you to get a better understanding of each other.
I know how difficult it can be to not immediately react. I have faced with such situations several times during my career. During one instance, a co-worker intentionally dismissed me in from of some other co-workers when I approached her with a question. Yes, my blood pressure rose off the charts. I quickly thought before I responded and went to my manager’s office to inform her of the situation. When she saw how upset I was, she directed me to remain in her office and calm down. She also advised me that I should wait a couple of days before addressing the other person regarding the matter. I followed her advice and things ultimately worked out well.

• Make a plan. I find it helpful to make a plan. I am not referring to some elaborate undertaking. I mean, decide when will be the best time to approach the person who you need to speak with. You want to approach them at the time when they are the least distracted. You should also approach them when you can have privacy to speak with each other. If they are a morning person, it is likely that approaching them early in day is ideal. Then, make notes for yourself of the points of discussion. It is important to get everything “on the table” and not create a back-and-forth exchange. You will be able to use your notes to keep the conversation on track. These types of conversations can sometimes become emotional and you often walk away and you later realize that you did not address each point that you had in your mind to discuss.
• Have Your Facts Together and Consider Them Carefully and Completely. One way to lose your credibility quickly is to fail to gather, understand, and consider the facts associated with the situation that you would like to address. It makes you look disorganized and undependable…especially if you try to correct someone else’s behavior and it is later realized that your decision to act was not a fully-informed one. Many factors can contribute the why someone acts in a certain manner. They may all not be immediately evident so it is important that before you react, you conduct your due diligence to gather as many of the facts as you possibly can. Knowing as many of the facts related to the situation as possible will enable you to avoid making assumptions. You know what the old adage says about when we assume. You might even become aware of something that will cause you to either understand the other person’s actions better or even decide to approach the situation differently. You will also emerge more favorably because you exhibited emotional intelligence.
For example, if your objective is to address an offense by your superior, you need to remain cognizant that you will be speaking with your superior. I would recommend approaching him/her by telling them that you felt uncomfortable with the interaction between the two of you on a given day, regarding a particular situation. Be prepared to provide specific details regarding the interaction. Be careful to not present an accusatory demeanor, but in an effort to provide context to the conversation. Even if your conversation is with a colleague, it is a good idea to approach the conversation in a similar manner. They are your colleague and everyone does everything. Remember, human interaction is about preserving relationships when possible.
If your objective is to ask for a salary increase, make certain to gather supporting documentation that will justify the pay increase. For instance, if you have improved a work process or created a new work process you need to be able to explain, or you may have updated a process manual, improved time to resolution for clients. These are examples of performance that is substantial and could justify an increase in pay.
• Be Open to a Different Perspective. Don’t think that what/how you think is the only correct way. It amazes me, and not in a good way, when I witness or interact with someone who carries themselves as if other people bring absolutely no value to the table, and that the other person has no right to have a different point of view from theirs. It is very important that we respect each other’s right to our respective opinions. Remember, that you could have unknowingly done or said something that equally offended the other person. So, their actions could have been in response to their feelings of hurt that were brought on by your behavior towards them. All I’m encouraging you to do is keep an open, objective mind and be ready to accept constructive criticism just as you want the other person to.

• Don’t make personal attacks. Remember, once again, that you are interacting with another human being. Also, your objective should be to address the person’s behavior, not the person. If you personally attack them, you will have essentially done the same thing to them that you feel they did to you. Also, surprisingly, if you intentionally hurt the other person, you won’t feel as good as you might think. If you have one shred of decency, your conscience will do a number on you because you will know that you could have handled the situation differently for a better outcome. Also, if the other person is your superior, and you verbally attack them, you could quickly find yourself out of a job.

• Maintain your composure. The worst thing that you could do, while discussing the issue, is let your emotions get the best of you and allow yourself to act out of anger. I suggest that if you feel yourself losing your cool, it is best to end the conversation and walk away. If you need to, revisit the issue a little later.

• Address to issue. Do not drag your feet on having the conversation. If you don’t have that all-important conversation, you will continue to feel strongly about it and, you may not notice, but you will begin to interact differently with the other person. Your work relationship will suffer and could deteriorate to the point of no return. As we all know, we spend too much time at work, with our co-workers, to not enjoy the atmosphere. The sooner you address the issue, the better.

• Let it go. One you and the other person have engaged in a honest, respectful conversation regarding the issue(s) of concern, let the issue go. Even if you have a difference of opinion later, don’t bring this issue up. Consider the matter resolved and move forward with healthy interactions in the future.

If you have a difficult conversation on the horizon in the workplace, I hope that these recommendations will help you navigate the situation successfully. If you try them, drop me an email to let me know what you think. Here’s to health workplace communications!

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