The necessity to initiate a difficult conversation is not limited to those in management, and while conversations surrounding terminations and disciplinary action are arguably the most difficult to handle with poise, there are other issues that you will need to address throughout your career. Regardless of your job title, whether you are an hourly employee or a regional manager, what can make a hard conversation even more difficult is going into it unprepared. By utilizing the following steps, you can turn those hard conversations into productive discussions.


  • Determine the purpose of your conversation. Even though your grievances may be many, your message should be singular. Larger issues that are impacting your ability to be productive while at work should be prioritized, while small annoyances should be tackled at a later time. If you bring too many issues into the conversation, the likelihood of the recipient becoming defensive and overwhelmed, rather than open and accepting of constructive feedback, increases tremendously. 
  • Recognize and deal with your feelings. When you need to have a particularly difficult conversation at work, chances are that there are strong emotions involved. Are you angry? Frustrated? Upset? Disappointed? Anxious? Whatever feelings are driving your need to have the conversation, identify them before the conversation takes place in order to help you keep them in check.
  • Practice what you are going to say. Write out what you would like to say, read it and edit it. This process can be lengthy, but is worth the additional time and effort. While you are editing your script, make sure that you are honing in on what you truly want to convey and not leading with your emotions. Lack of planning what you are going to say may cause you to default to expressing emotion over facts, turning your productive conversation into a personal attack.
  • Schedule an open time and neutral place. The time and place that you decide to meet is crucial to the success of these conversations. Ideally, everyone involved will be able to carve out some time in their schedule to talk, and you can offer some potential locations that are both neutral and private.


  • Open the conversation. Although they likely have an idea of why you wanted to talk with them, start the conversation by stating why you scheduled the meeting and ask them what their thoughts and feelings are on the subject.

Example: I would like to talk with you about ______, but first I wanted to get your thoughts.

They likely have been noticing the same issues that you have, and this is a good way to make them feel like they are a part of a conversation.

  • Acknowledge their thoughts. Even if you completely disagree, acknowledge their perspective. Show them that while your opinions may differ, you are open to hearing what they have to say and want to reach a mutually beneficial resolution.  
  • Give direct and specific feedback. As you acknowledge their thoughts, don’t shy away from giving direct and specific feedback (in a tactful manner). Again, refer to what you wrote down so that you can keep the conversation on track. The more specific details that you give the better, don’t generalize. Words like “always” and “never” are not productive and will generate feelings of blame and resentment.
  • Offer potential solutions. Make sure that after feedback is given, you offer potential solutions to the issue or issues you discussed. Brainstorm ideas before you go into the meeting, just make sure that you aren’t the only one who will benefit from your potential solutions.
  • Try to reach a resolution. While not guaranteed, with an open mind and tactful conversation, you stand a good chance of finding some middle ground and reaching a resolution by the end of a hard conversation. Remember, a good resolution is one that no one is completely happy with because they met the other person in the middle.

Follow up:

  • Often times, that initial hard conversation is only the tip of the iceberg- the real work begins when the conversation concludes. At the end of your conversation, decide when you are going to check back in to see how things are progressing. Make sure that you stick to this timeline and don’t be afraid to revisit the same conversation periodically. Also, make sure that if you are not seeing resolution or follow up from the other person that you get HR involved to mediate future conversations.