How to Have a Difficult Conversation with your Supervisor

If you are like most people, you have opportunities to initiate difficult conversations on a frequent basis, but they probably don’t really feel like “opportunities”, do they?

For purposes of this communication, we are using the term “difficult conversations” to convey a situation where both parties in the conversation need to stay in a relationship, the stakes are high, opinions vary and emotions may run strong. At work, situations may arise between you and your supervisor that call for you to initiate a difficult conversation. Your supervisor may be many things, but it is doubtful s/he is a mind-reader. So if something is not working for you at work that your supervisor can influence, and it matters to you that it is not working, you’ll want to find your voice.


Conducting a Difficult Conversation

There are four basic steps to conducting a difficult conversation:

  • Preparation
  • Initiation
  • Discussion
  • Conclusion

Please read on for tips and examples that will help you to have a successful conversation on a difficult matter.


In the book “Crucial Conversations”, the authors recommend asking yourself some basic questions to help you internalize your intent, such as “What do I want for me?”, “What do I want for my supervisor?”, “What do I want for our work relationship?” It’s important to be clear on the message you want to deliver and what you are hoping to gain from your effort. From these questions, you can move on and ask yourself even more questions:

  • What is the issue that needs to be addressed?
  • What are the facts of the situation? (Look at those facts as a neutral observer would describe them. Your perspective may change when you take a step back.)
  • What does resolution look like?
  • What are the possibilities of how your supervisor might react? And consequently, how would you then react?

Try a role-play with someone you trust. It improves performance. Start out by explaining the situation to your partner. Put on your neutral-observer hat and share your feelings without accusation or blame – pretend you are an objective news reporter and attempt to explain both sides. Then, have your partner be you and you play the role of your supervisor. Listen and react the way you think s/he would. Then, switch roles and be yourself and rehearse again. Chances are you will gain insights that will improve the way you navigate the real conversation.

When you have a good idea of what to say and how you want to convey your message, let your supervisor know you would like to discuss an issue and request a time to do so. In some situations you may want to elaborate briefly on the nature of the issue. Example:

“I’ve been reviewing my objectives for the year and have a few ideas that I’d like to discuss with you. Would Thursday be a good day for me to schedule something?”

Your supervisor may ask you to talk right then and there. If you do not feel ready, or you feel as if your supervisor is too rushed to be able to respond thoughtfully, state that you were expecting a little time to finish preparing your thoughts and that you’d prefer to discuss at a later date.


Open your one-on-one discussion with a statement to help remind you both that you have a working relationship based on a shared goal. This allows both parties to start the conversation from the same place. Examples:

“I know one of our top goals for this semester is to complete the categorization project. And to stay on track with that, I want to discuss X and Y.” [OR]

“I know change is continuous in our department and that we have a culture of valuing flexibility. There is a recent change, though, the one regarding X, that is causing me some concern and I’d like to talk with you sometime this week. When would be a good time?”


A methodology offered by the authors of “Crucial Conversations” is captured in the Acronym STATE:

Share your facts

Tell your story

Ask for their view

Talk tentatively

Encourage testing

The first three statements (Share, Tell, Ask) are what you do. The last two statements (Talk, Encourage) are how you do it. Take a look at the following two examples:

Example 1: “In the meeting on Monday, I heard you say xyz. When I heard it, I felt undermined because of abc. I’m wondering if you can understand my feelings?” Example 2: “In the meeting on Monday, you said xyz. When you said that, you undermined me because abc. Is there a reason why you undermined me?”

Example one opens a discussion on your feelings and perception of an event. Example two places blame and may evoke defensiveness, which is detrimental to having a productive discussion.

During the discussion, you’ll perform two major activities: Communicating your ideas in a calm and logical manner and really listening (not just hearing) to what the other person is saying. You’ll also want to demonstrate that you are accountable for the parts of the issue you may have caused. If you believe you’ve played no part in the problem, you are probably not being realistic.

If notes or an outline helps you stay on track during your discussion, feel free to use them. However, don’t read from the page. You’ll want to be making eye-contact and engaging with your supervisor, person to person.


As with any meeting or involved discussion, you should summarize agreements, disagreements and action items. And, depending upon the issue being discussed, there may be a need for a follow-up discussion. The conclusion is a good place to remind the person once again, as you did in the initiation, that you have a working relationship based on a shared goal(s). Examples:

“I am glad we had a chance to talk about X and Y. I know how important the categorization project is to the department. I feel like the questions and concerns I had about X have been resolved in that we decided to do ABC. You provided some new information about Y that I need to look into, and so I’d like to get back with you next week. How does that sound? Is there anything else you feel we should discuss regarding this topic?”

“Thanks for talking with me about the concerns I had regarding the change in process. Based on our conversation, It sounds as if the process is going to remain the same, and though I still have several concerns, I appreciate you hearing me out and I will do all I can to make it work as we both want the department to remain efficient and flexible. Would you like me to get back with you in a few weeks to let you know how it’s going? ”

Difficult Conversation Scenarios:

Few of us are naturals at successfully initiating and engaging in a difficult conversation. It takes practice and preparation. Below are work place scenarios that might warrant a difficult conversation along with suggestions on how to get started.

Receiving a disappointing performance evaluation

Scenario: “I just received my second performance evaluation since joining this department. I was scored as “meets” my first year and I understood that because I was new. But this year I was expecting “exceeds”. I have done everything my supervisor asked me to do. I’ve taken initiative, received many compliments from clients, and contributed overall to the team. I am very disappointed. And, to make matters worse, my co-worker, who does not do as much work as I do but has been around forever, received an “exceeds” rating. How do I get my manager to change my rating?”

Preparation: Does your supervisor know your accomplishments for the year or do you think s/he may not be aware? The answer to this will guide the approach to your discussion.

If the evaluation has captured your accomplishments and/or your supervisor’s feedback throughout the year indicates that s/he grasps your contributions, then the primary issue to address is how your supervisor defines “meets” and “exceeds.” What performance and behaviors illustrate “meets”? “Exceeds”? In this circumstance, it is unlikely that your supervisor will change the overall rating. But, even if the change you want does not occur, having a discussion now will position you much better for next year’s performance evaluation as you’ll have a clearer vision of what s/he sees as warranting an “exceeds.” This conversation also may shed some light on why your supervisor assesses your co-worker differently than you do.

On the other hand, if you aren’t confident that your supervisor is aware of some of your accomplishments, and that may be why you did not receive an “exceeds,” the discussion will focus much more on sharing that information. And, in this circumstance, there is a better chance that your supervisor might reconsider his/her scoring. At a minimum, you should include your additional accomplishments or comments in the employee response section of the appraisal.

Initiation: After setting up a time in advance to meet with your supervisor and letting him/her know that it is to discuss your evaluation, one approach to begin a discussion on what characterizes “exceeds” versus “meets” might be along the lines of: “Thanks for meeting with me. I know that we have already discussed my annual appraisal and I feel as if you have recognized a lot of what I have accomplished during the year. I want to be considered a top performer and contribute to the department and I know you would like that for me as well. I’ve learned a lot over this past year and challenged myself to do the best job that I could do. So when I saw that my overall evaluation score was “meets” rather than “exceeds,” I felt disappointed. I would like to better understand what I need to demonstrate in my position to be considered as “exceeding” expectations. Is that something that we can talk about now?”

A discussion to share accomplishments that you think your supervisor might not have considered when evaluating your performance could start off with something like: “Thanks for meeting with me. I’ve been giving further thought to my evaluation and while I realize that not every accomplishment or project can be addressed in the document, I wanted a chance to share some information with you about a few accomplishments I had during the year that I may not have made you aware of. To be honest, I put a lot of effort into my job this last year and felt disappointed that my overall score was “meets.” My hope is that by having this discussion, I will get a better idea of what you consider “exceeding” my job expectations as that is what I want to do for myself and for the department. I am also hoping that if I am presenting you with some new information during this discussion, we might be able to adjust the evaluation to reflect it. If this sounds acceptable to you, I’d like to start off by highlighting (Project X) and get some feedback from you about where my performance was strong and where it could have been stronger. How does that sound?”

Discussion: STATE: Share your facts; Tell your story; Ask for their view; Talk tentatively; Encourage testing.

For this scenario, be advised that it is generally not a good practice to bring up other employees and their evaluation scores during a conversation about you and your score. It puts a supervisor in an awkward position. Supervisors should not be discussing one employee’s performance with another employee. Additionally, it moves the conversation spotlight from being on you and your strengths to someone else. Finally, it can trigger defensiveness in a supervisor.

While you may be tempted to cover a long list of accomplishments, be selective for purposes of time. You can always choose to attach a document to the evaluation that provides information on your accomplishments and will be included along with the evaluation in your personnel file.

As you seek to understand what your supervisor considers to be “exceeds” versus “meets,” use a past project, task or objective with which you are both familiar and ask your supervisor to use real examples to illustrate what exceeded and what did not exceed expectations. Or, it may be easier to ask your supervisor to describe preferred performance in your role that would constitute “exceeding” expectations.

Conclusion: Examples of conclusions for this scenario: “I think I have a better idea of my focus in order to be considered as exceeding the expectations for my job. (Perhaps summarize what that focus looks like). Thank you for the information. Please know that I will welcome your feedback throughout the year and if you see improvement opportunities for me, please do let me know. My goal is that this time next year, my performance warrants an “exceeds”. Is there any additional training or learning that you would recommend?” {OR}

“Thank you for meeting with me. I’m glad I had a chance to tell you more specifics about my work. What I’m hearing from you is that the work I have done is fine and has contributed, and you see it as meeting the expectations for my position. Is that right? I would like to attach a short document to my evaluation noting some of the accomplishments I shared with you today. May I get that to you next week? Right now I am not certain that I understand what exactly I’ll do differently in order to exceed expectations, but I am going to think more about our conversation. Given that you know I want to contribute as much as I can to the department in this role, please give me feedback if I can be doing something better. May I check back with you in a few months to see how I’m doing?” {OR}

“Thanks so much for listening to my information and I am encouraged that you are willing to reconsider my overall score on the evaluation. Is there any additional information I can provide that would help you make your decision? When may I check back with you on status?”

Asking for a pay increase

Scenario: “I have worked in my department for four years. We’ve had a lot of turnover which has been good and bad. Good because I’ve learned a lot by covering other positions and bad because I now have significantly more work and no higher title or more salary. I know money is tight, but I want to ask my manager for a raise.”

Preparation: How does your department handle non-merit salary increases? Be aware that departments often have their own guidelines on salary management. For example, some departments only have certain times of the year when a supervisor can reclassify a person’s position to a higher level. And, the university has set times of year when employees are able to receive a merit increase (if approved by the legislature). In short, making a decision to give you more money is often beyond the control of your supervisor so do not expect to walk away from your conversation with a firm commitment to increase your pay; your supervisor will most likely need to get back with you.

Be ready to discuss specific tasks or projects that you have taken on during your tenure in this position in this department; focus in particular on the last 12 months. Realize that everyone takes on more and/or different tasks during their employment. What you want to be able to communicate effectively to your supervisor is that the scope of your responsibilities has become more complex or that the number of tasks you now own has increased by a large percentage.

This scenario focuses on asking for an increase in pay. Don’t assume that this would always involve getting a new job title. Similar scenarios might also focus on asking for a new title along with an increase in pay. Before you initiate a discussion, think through the specifics regarding your request from your supervisor.

Conduct a few internet searches to see what you can find for salaries for your position in central Texas. Determine the university’s salary range for your job. Consider the salary increases you have had during your tenure in the position. Additionally, take a look at your current Total Rewards Statement. You may or may not want to use this information in your discussion.

Finally, are you in good standing with your supervisor? Was your last evaluation favorable? Is the feedback you receive positive? Are you on any corrective action?

Initiation: After setting up a time in advance with your supervisor for your discussion, you might state something like: “Thank you for meeting with me today. I wanted a chance to talk with you about my position and some of the changes in responsibilities I’ve had in the past few years due to the resignations and new systems we’ve introduced. The first thing I want to say is that I am pleased I have been able to learn so much and been able to grow professionally in my knowledge base and skill sets. And while I am grateful to have taken on more complex tasks, and want to continue doing what I do, I also would like to see what could be done to move my compensation more in line with the job I am performing today. I’ve identified some of the more significant changes to my responsibilities since I was hired into this position and would be glad to give you a quick rundown. Does that sound like a good place for us to start our discussion?”

Discussion: STATE: Share your facts; Tell your story; Ask for their view; Talk tentatively; Encourage testing.

In the preparation stage, you probably acquainted yourself with salary data and may have a notion of the salary increase you believe would be appropriate or that you would like to have. Do let your supervisor warm up to the idea that you are requesting more money before you go into specifics. Alternatively, you may not even want to get into a specific amount of increase and leave it up to your supervisor to do what s/he can.

Conclusion: In a salary focused conversation, it is rare that a supervisor makes a final decision at the end of the initial conversation. An example of a conclusion for this scenario: “I’m glad we were able to have this discussion. As I said, I like what I am doing and want to keep doing it. My request is to receive some financial recognition of the additional responsibilities that I’ve taken on. Is there any other information that I could provide that would help you/you and your manager make a decision on my request? When should I expect to hear back from you?”

Being Micromanaged

Scenario: “About four months ago, I transferred to a new role in a new department. My supervisor was initially very hands-on in providing training and frequently met with me to see how my work was progressing. The feedback I received from him was mostly positive and I thought he was pleased with my progress. However, I now know the ropes but he still continues as if I am in training-mode; it feels like I am being micromanaged. I don’t like working this way and want to tell him.”

Preparation: Although it sounds as if you may be the only recent hire, have you observed whether your supervisor tends to micromanage others, or does it just seem to be you? If you are seeing this trait evident in other work relationships he has, you probably won’t see a behavior change in him quickly as this is obviously part of his management habit and habits take time to change. But, you might as well start the conversations now. When speaking with him, contain your examples of micromanaging to those you have directly experienced. You don’t need to be the spokesperson for the group and you don’t want to overwhelm your supervisor with input. Speak for yourself only.

If you don’t observe your supervisor micromanaging anyone but you, consider that it might be a dynamic between just the two of you. Avoid the temptation to ask others if they feel micromanaged, it’s not critical for you to know and it may be perceived as a negative toward the supervisor and/or team dynamics. Consider what specific performance feedback you have received from your supervisor. You state that you think he is pleased with your progress. What has he said or done that makes you think this? Sometimes supervisors will micromanage when they have doubts about an employee’s ability to do the job as it needs to be done. Be aware that in having a conversation with your supervisor about micromanaging, he may tell you something(s) you are doing that he does not like. Practice how you will react should this occur.

Prior to asking your supervisor to be less hands-on, you’ll be well served to establish the level of performer he considers you to be.

Initiation: After setting up a time in advance with your supervisor for discussion, one approach to kick off the meeting may be, “As I said when I asked if we could meet, I’ve been in my role about four months now and wanted to check in with you and see how you feel about the progress I’ve made. You have helped me to learn a lot about my role in the department and, as a result, I feel pretty self-sufficient. I want to contribute to the department and I want to take up less of your time as we move forward. Knowing where I need to focus and where you still need to assist versus where you no longer need to be involved in the day-to-day will be useful for us both. May we talk about that? (If so), I can start off with where I think I am ready to be independent and where I may still need further development. You can then let me know if you agree or have a different assessment. Does that work?”

Discussion: STATE: Share your facts; Tell your story; Ask for their view; Talk tentatively; Encourage testing.

The beginning of your discussion should be focused on receiving a clear picture of how your supervisor views your performance. If that picture is positive, then move toward clarifying when the two of you should expect to be working closely together and when you can expect to be on your own. In the areas where you are ready to be on your own, you might want to make a statement to emphasize your desire to not be micromanaged. For example, “I’m glad to hear that you’re ready for me to handle A, B and C independently. I look forward to this and I think it will allow me to learn even more in a different way – finding answers without having you right there to tell me will round out the training you’ve provided and build my confidence.”

However, if the picture of your performance indicates that your supervisor has some concerns, you are not at the right stage to be asking him to manage you less. Try to get examples to illustrate what you are doing now that is not effective in your supervisor’s opinion and what it would look like if you were being effective.

By the way, in this initial discussion, shy away from calling the problem “micromanagement” and instead just talk about how the two of you are working together without using a label. If the problem does persist and you have other discussions, then you may want to branch into expressing that you feel micromanaged.

Conclusion: If the discussion was primarily focused on improvement areas for you, a conclusion may go along the lines of: “I am glad we’ve talked. I didn’t realize I wasn’t handling A and B as you expected. From the examples we discussed, I have a clearer idea of what you are looking for; it sounds as if I need to do more X and less Y. Is that right? In the other parts of the job, it sounds as if you are satisfied with how I am coming along. Do I have that right? I am a little surprised and nervous right now with the feedback you provided; and I wish I had known earlier. I will think about this further and may have another question or two for you about A. And, please, if you see me doing anything off course, let me know. I want to do a good job.”

If the discussion illustrated that your supervisor thinks you are performing well and there are responsibilities where he feels you can be independent, you may close with something like, “I’m glad we had this discussion. It sounds as if starting tomorrow, I will be doing A, B, C and D pretty much on my own and you are tasking me with coming to you if I need assistance, rather than you outlining the steps for me to follow when you give me an assignment. But with E and F, you are going to want to stay involved for a while longer. Do I have that right? Maybe we can have another conversation in a month or so to see where I am on E and F? Thanks for meeting with me and giving me this input. And thank you for the time you’ve taken to train me.”

Working with a weak co-worker

Scenario: “My co-worker is not pulling his weight on the job and I don’t think our supervisor notices. There are three of us providing similar services but only two of us doing any actual work. I’ve made it clear to my co-worker that he needs to be more responsive to customers and not disappear when the big jobs come in, but he says I have no right to imply that he is not working hard enough. The next time it happens, I’m going to tell our supervisor and ask him to do something.”

Preparation: Are you sure your co-worker is not doing any work? Challenge yourself to look at the situation objectively. Does your other co-worker also believe that there is an imbalance of workload between the three of you? Your frustration with the situation may be prompting you to exaggerate the problem. Perhaps it’s not that your co-worker does no work; maybe he is choosing to only do one or two types of work and avoid other types? You’ll want to identify the correct problem in order to achieve a successful outcome.

Judging from the scenario, “I’ve made it clear to my co-worker” and “not disappear” and “working hard enough,” it does not sound as if you engaged your co-worker in a discussion about the problem. It sounds as if you may have told the employee what the problem was and how it was his fault. You might want to try giving your co-worker feedback using the STATE process before going to your supervisor.

Think of four to six examples of times over the last 90-days when you perceived that the co-worker did not carry his share of the load. Be prepared to share these examples in a factual, calm manner with your supervisor (or with the employee himself if you decide to try a discussion).

Your objective in the discussion with your supervisor needs to be focused on the impact to the business. Avoid language that sounds as if you are having a personal problem with the co-worker. Keep your emotions in check and do not let frustration with the situation take control of your message.

Realize that you will probably be doing the majority of the talking in this discussion. Your role is to present the issue that is impacting the running of the department or area and provide examples. Your supervisor, because s/he will not talk in detail about one employee to another employee as it breaches confidentiality, will probably ask clarifying questions and listen. It may be that your supervisor is aware of the problem already and in the process of taking steps; however, again, it’s doubtful that your supervisor would share this with you or should share this with you.

Initiation: After setting up a time in advance with your supervisor for your discussion, make it clear you are focused on the effectiveness of the team’s work output, such as: “Over the last few months, I’ve gone back and forth with myself if I should talk with you regarding a concern I have with the way our team is working together. I don’t want you to perceive me as being negative or being unsupportive of my co-workers. However, an incident happened last week that made me realize that I needed to speak with you. I know you want us to achieve our department objectives and I am seeing something that may get in the way of us providing excellent customer service. Specifically, some of our customer orders are not being completed as timely and effectively as they could be because, during significant chunks of each day, only two of the three of us assigned to xyz appear to be fully engaged. The two who are engaged is me and NAME. I have a few examples and observations that have occurred since MONTH that illustrate my concerns. May I share them with you?”

Discussion: STATE: Share your facts; Tell your story; Ask for their view; Talk tentatively; Encourage testing.

Let your supervisor know that you have attempted to speak with the employee regarding the work load and your concerns but it did not bring about positive change. This shows you have taken initiative to try to resolve the situation. If you feel as if you might not have handled the conversation with the employee particularly well, go ahead and own up to it now with your supervisor. It’s best that he hears it from you. Chances are if the supervisor talks to the employee about the issues, the employee will be sure to let the supervisor know that you didn’t do such a good job in expressing yourself.

Don’t let your supervisor get the impression that you and the other “hard working” employee spend a lot of time discussing the (perceived) problem employee. You don’t want to be perceived as making a problem worse by becoming unproductive yourself.

With each example you share, be explicit about a negative business impact it has. If you want to have some notes to refer to during this conversation, feel free to do so. If you are concerned you may end up appearing overly frustrated or angry about the situation, the notes may help ground you.

Conclusion: Unlike most discussions, this time you probably won’t know what next steps the supervisor will take. Be comfortable leaving it in his or her hands to address as they think best. A conclusion might look like, “Thank you for listening to my concerns regarding our team’s workload and the importance of all of us working toward the department’s objectives. Do you have other questions for me? Based on the examples I’ve shared with you, is there anything that you’d like me to do differently on the team? “

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