Leading difficult conversations in the workplace


Take a moment and think back to the last difficult conversation you had with someone at work. Are your hands getting clammy? Is there a slight knot in your stomach?

If you’re like most people, the mere thought of initiating or participating in a difficult conversation is enough to make you uncomfortable. No matter how hard you might try to avoid them, difficult conversations are bound to happen at some point during your career.

Whether you own your own business, manage a team, or are just starting out in your career, knowing how to effectively lead a tough conversation can dramatically influence the outcome of the meeting. While it may not be easy to ask for a raise, discuss poor performance, or simply deliver bad news, there are some important best practices you can utilize to prepare yourself and hopefully make it just a little bit easier.

Executive coach Barbara Rapaport, president of Real-time Perspectives, has broken down a difficult conversation into four parts: results, relating strategy, discussion and reactions.


Before a difficult conversation is even initiated you should take a moment to determine what your desired results for the conversation are. What are you trying to accomplish? Why is that result important? Additionally, it is important to identify a minimum and maximum evidence of success. How will you know that the conversation went well? Thinking through what you hope to accomplish is the best way to begin framing a hard conversation.

Relating strategy

After determining your goals it is important to think through the way you conduct the conversation. There are three components to your relating strategy that will set the tone of the discussion:

1. Formal vs. Informal: Do you have a formal relationship with this person, or informal? Does the topic at hand warrant a more formal tone than usual?

2. Ask vs. Tell: Are you looking for feedback from someone? Is this an open discussion, or do you need to communicate a decision that has already been made?

3. Show vs. Conceal Emotions: Is it appropriate to show an emotional response, or should you remain neutral?

Thinking through these different elements will help you shape the tone of discussion and feel emotionally prepared when you begin.


Now we’re down to the details. Actually having the conversation might still be uncomfortable, but sticking to the following agenda will ensure you stay on task and communicate everything you intended to.

1. Invitation: Set up a specific time to talk to the individual. Don’t just barge into someone’s office — make sure the meeting works within their schedule and communicate the purpose of the meeting ahead of time.

2. Opening: Getting the conversation going can sometimes feel awkward. Simply start with a statement like “Thank you for agreeing to meet with me today. I’d like to discuss XYZ. Is now still a good time to do so?” Remind them what you’d like to discuss and why.

3. Key Points: Discuss the key points of your position and be sure to allow for respectful dialogue with the other individual.

4. Close: Summarize what you heard in the conversation, so both parties leave the meeting on the same page.

5. Follow-Up: Thank the individual for their time and input. Other action items depend on what was decided during the discussion.


Prior to your discussion, anticipate some potential objections and determine how you could handle them effectively. Was it merely a misunderstanding? Does the party who “objects” express a legitimate concern? Or will the party who “objects” express complete disinterest in the topic you wish to discuss? Additionally, anticipating your own real-time reactions to the feedback you may receive will help you feel prepared for multiple outcomes and control a potentially emotionally reactive response.

Though difficult conversations are never fun, taking the time to prepare for them can improve your confidence and possibly even the outcome of the discussion. Simply re-framing the term “difficult” into “productive” can help you approach an uncomfortable discussion in a new light.

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