How to Have a Difficult Conversation with your Supervisor

If you are like most people, you may have opportunities to initiate difficult conversations on a regular basis, but it probably doesn’t really feel like an “opportunity,” does it?

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 they are 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 will want to find your voice.

Here are links to other resources and training available to help you prepare for a difficult conversation:

Conducting a Difficult Conversation

There are four basic steps:

  • 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 is important to be clear on the message you want to deliver and what you hope to gain from your effort. From these questions, you can move on and ask yourself the following:

  • 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?
  • How might your supervisor react? How would you then react?

Try a role-play with someone you trust. Start 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 they 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. 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 example:

“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?”

The example opens a discussion on your feelings and perception of an event.

During the discussion, you will perform two major activities: Communicate your ideas in a calm and logical manner and really listen (not just hearing) to what the other person is saying. You will want to demonstrate that you are also accountable. If you believe you have played no part in the problem, you are probably not being realistic.

If an outline helps you stay on track during your discussion, feel free to use it. However, do not read from the page. You will want to make eye-contact and engage with your supervisor.


As with any meeting or involved discussion, you should summarize agreements, disagreements and action items. 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 during the initiation phase, that you have a working relationship based on a shared goal(s). Example:

“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?”

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.