3 P's to Make Tough Conversations a Little Easier


Only 14% of HR managers think managers in their organizations are good at having tough conversations. It’s the #1 manager problem. Sometimes those tough conversations feel like a mountain standing between you and drawing great performance out of your team.

These three P’s will make your mountainous “alignment conversations” more surmountable.



Any tough conversation starts with a conversation with ourselves. This conversation—not the one with the other person—is the toughest conversation we will have. In it, we need to articulate the issue, determine our expected outcomes, and examine your emotions.

  1. Articulate the issue. Tough conversations shouldn’t be held out of frustration, but rather to accomplish a goal that relieves the frustration. What is the real problem that you are trying to solve? If you can’t succinctly articulate the specific aspects of the issue before starting a conversation, you certainly won’t be able to articulate your concerns during the conversation.

  2. Determine expected outcomes. Conversations aren’t helpful if they don’t begin with an end goal in mind. What needs to happen at the end of the conversation for you to feel that the conversation was successful? When it’s time to actually old the conversation, make sure that the other person understands and agrees with your goal. You might need to refine the goal in the moment, but it helps to know where you’re starting.

  3. Examine your emotions. Most people try to avoid tough conversations for fear of hurting the other person’s feelings. It’s important to take stock of and minimize your emotions so they don’t get in the way. Equally important is to not take responsibility for the other person’s emotions. You can’t control how the other person will feel, but you can anticipate and control your reaction to those emotions. 

In any tough “alignment” conversation, your goal is to help the other person take some ownership of the “issue.” Determine what will get the person’s attention focused on the right things. Also consider what your do if you can’t get his or her attention.


Plan in detail what you intend to say and do. Determine what questions you want to ask and specifically how you want to ask them. Anticipate how the other person will respond to each statement. You’ll be more prepared to respond and you may realize things you missed when thinking about your questions.

Begin tough conversations by using an “I” statement (“I have a problem”) rather than “you” statements (“you have been…”). “You” statements tend to make people defensive and less open to hearing what you have to say and truly collaborating to solve the problem. Make sure the other person knows you want their help and that you intend for the conversation to be collaborative.

It’s also important to plan an appropriate time and place for the conversation. Consider what distractions could hamper a productive conversation and plan accordingly. Generally, these conversations should take place in a private, one-on-one setting at a time when you can both give your full attention to the conversation.


You might begin by practicing the conversation silently, or aloud by yourself, but don’t neglect to practice with someone else. Recruit a trusted co-worker, friend, or family member to help you practice your responses to unanticipated reactions in real-time.

Practicing with a friend will also grant you the opportunity to practice active listening. Check to make you understand what the other person is saying or feeling. Listen to understand, not respond. Make a point to paraphrase back what the other person has said so that you are focused on what the person is saying, not how you are going to respond. It’s okay to finish listening and take a few seconds to think through your response.

Don’t worry if the first practice session doesn’t go well. Allow yourself as many “do overs” as needed so you feel confident and comfortable. If you aren’t comfortable, you can’t help the other person be comfortable which will stifle the flow of solutions for both of you.

Having a great coaching conversation is like building a muscle—the more you exercise the stronger you get. Preparing, planning, and practicing is the exercise required to scale the mountain preventing productive dialogue.

Tough conversations are tricky for anyone, but they’re especially challenging for new managers. Discover more important skills for new managers, including more tough conversation tips, in this e-book.


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