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Learn the invaluable trick great leaders use to manage difficult conversations

Difficult conversations are unavoidable, but it's sometimes tough to know where to begin.

5 min read


In the lifetime of any manager, there will be many difficult conversations. Whatever the reason — performance, behavior or bad news — it can be hard to know where to start in having that difficult talk with someone. Worse, when a situation arises, there isn’t always time to plan a strategy on how you’re going to tackle it. Prepare yourself now by practicing the trick great leaders use to manage emotions and get to finding a way forward in many potentially stressful settings. It might surprise you to learn that the number one strategy for starting a difficult conversation isn’t talking at all; it’s listening. By modeling the open conversations you expect, you can lead the way to more positive outcomes and relationships. Before you begin, use this template to determine what you need to cover before entering into a difficult conversation. Make notes:

Where:  An appropriate location. Make sure you have:

  • A spot away from and out of earshot/sight other team members
  • The ability to speak frankly together, and be heard
  • Neutral space, if possible and feasible (i.e. neither of your offices, perhaps a coffee shop)

When: As soon as possible after an incident has occurred. While it takes courage, the sooner you can have the conversation, the sooner those involved can move on to healing. When you initiate the conversation, set a time limit along with laying out what you want to discuss.

What: Be specific about the issue. What exactly has gone wrong or in what area are you requesting improvement? Note as well how you feel about the situation, what you expect as an outcome from your meeting, and going forward.

Now that you have a plan ready, prepare to listen. Your notes will help you stay on message resist the urge to ramble. Start with an open-ended question like “Tell me about what happened today in the staff meeting with George.” Then use the following three-step process to frame your discussion and leverage listening to get through even the most difficult conversation.

  1. Mirror the conversation

Periodically take the opportunity to repeat back or paraphrase the other person’s statements back to them, without any of your own judgement or assessment, to verify that you are understanding their position correctly. For example, “So you’re saying that George arrived at the meeting in a bad mood and prepared to shoot down your idea, is that right? The back and forth that escalated after was more about his state of mind than your response to his criticism, is that correct?” Try to stick with relaying back exactly what was said if at all possible, unless you can truly paraphrase without reverting to your own position — merely mirror to confirm that you understand their perspective.

  1. Ask questions

Continue to ask questions and keep the conversation going. Try to make them as open-ended as possible, like “I didn’t know that, can you tell me more?” or “That’s interesting, please tell me a bit about why you think that’s so.” Try to learn as much about the other person’s point of view as possible.

  1. Validate what is being said

As you learn more and continue to ask questions, validate what you are being told, such as “I understand you feel George was going to dislike the idea because it requires some of his budget, and you didn’t feel supported by others who had told you before it was an idea worth exploring.” Remember that this is about the other person’s perceptions, not yours. When validating, it is especially important to stay neutral. By using active listening, you will find it easier to verbalize empathy with the other person, while still having your opportunity to talk and to clearly and positively convey your feedback and expected outcomes. When people feel heard and validated, and have had a chance to verbalize their side of a difficult situation, it’s much easier to move forward with repairing relationships, improving performance and changing behaviors. All this may seem a bit daunting, but planning and practice can make all the difference when broaching a difficult subject. Consider how you are going to build your listening skills to be better prepared for the next difficult conversation in your future. The more you are prepared to actively listen, the better your outcomes can be.

Joel Garfinkle is the author of nine books, including “Difficult Conversations: Practical Tactics for Crucial Communication.” He is recognized as one of the top 50 coaches in the U.S., having worked with many of the world’s leading companies, including Oracle, Google, Amazon, Deloitte, The Ritz-Carlton, Gap and Starbucks. As an executive coach, he recently successful worked with a vice pPresident who had to have three difficult conversations with employees in his group due to poor performance. Sign up to his Fulfillment@Work newsletter (10,000+ subscribes) and you’ll receive the free e-book “41 Proven Strategies to Get Promoted Now!”

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