Leadership Insights for Difficult Conversations

As a leader, you will need to have difficult conversations. The critical part of difficult conversations is to give them enough time of planning that allows you to prepare what you need to say. Also, you want to make sure you don’t take too much time and avoid them either. Today, I share with you three aspects of the conversation that you must consider before having a difficult conversation. I also give you insight into what often gets in the way of having effective conversations about a difficult topic. We look at one challenge you will face as you prepare to let someone go. This behind the scenes look at difficult conversations will allow you to show up as a strong leader.

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Leadership Insights: The Transcript

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Disclaimer: This transcript was created using YouTube’s translator tool and that may mean that some of the words, grammar, and typos come from a misinterpretation of the video.

As a leader, we’re forced to have difficult conversations that we don’t wanna have. We’re forced the have them because we must coordinate actions and resources around the company. Sometimes that’s inside the company, outside the company, customers, vendors, strategic partners, you name it. Difficult conversations are a part of the job. When you face a difficult conversation, how do you prepare for that moment?

Well, as a leader, you’ve got to plan for the words that you’re going to say, for sure. You’ve got to understand the point that you’re trying to get across. Maybe it’s the questions that you’re asking because you’re curious about why something’s not finished already. Why you’re not getting the results. Or why one person’s not really committed to the work the way you think they should be. There’s a plethora of different reasons why you’re gonna have this difficult conversation. And your first job is to think about the words that you’re going to have. Now a second is to really think about the emotion that you’re bringing to that moment.

What is that emotion that is necessary to connect with the person? The better way to do it is to be intentional. But thirdly, you wanna think about when you’re going to have it. What’s the right timing of this? How do you make sure that that person’s in the mood to receive this bad news? All of those things are key factors in difficult decisions. And that’s something that you can get used to doing. For example, letting someone go on the team, very difficult. And I just had a conversation with a client around this about, how do you know it’s time to let someone go? And so that is something that is not external.

It’s not about the words, it’s not about the emotion, it’s not about even the timing. It’s about how you feel about that moment. About how have you been the leader that you really want to be and need to be to rise up? And be the leader that is necessary for that person. Have you given them the support, the coaching? Have you been empathetic enough? There’s a lot of questions that probably run through your mind. And you probably have some doubt around this. In fact, this client that I talking to said, “It was a nagging doubt.”

I share this with you because this is Behind the Scenes. We all deal with these aspects of hard conversations. What do you do with it? Well, when I talked to this leader about you know why they were not ready to let them go, but they felt that they should? It came down to one thing. It felt like they needed to actually slow down a little bit and actually coach this person up one more time. Be much more explicit about what’s expected of them in this role. About really how they were gonna show up. Not in a rude way, not in an authoritarian way. But how do you connect with that person to get them to either step into the role and commit, or get them to say, “Maybe this isn’t right for me, “maybe I need to move on”?

Because when you give it that one last shot you know that you’ve given everything, not flippantly, but you’ve intentionally shown up for that moment, for that person, and that difficult conversation, you know that you’ve done everything you can. And eventually, if they don’t rise up, you can let them go. If they do rise up, then you’ve you know kind of repaired a relationship and maybe you’ve even rebuilt trust, it’s really important.

I share this with you today because it’s something we all face as leaders. There’s many series of conversations we have internally that we have to deal with and struggle with. But here’s my sage advice for you, in all the experience that I’ve had, check-in with yourself. Maybe sometimes you check in with a third party that knows you to say, “I wanna have a conversation “so I get really clear about what I missed inside this.” Don’t try to blame someone else. But really figure out how you need to show up for that moment.

Give it everything you’ve got so that you know looking back that you didn’t question anything. You were there, you did it. Not everyone’s going to accept and own that role. Not everyone’s going to take a difficult conversation the way you want them to. But when you do everything you can, you show up and use the right words, right emotion, and at the right timing, you know that you actually care for that employee, that experience, and that conversation.

This is something that happens a lot with leaders. I share this with you because I work a lot with leaders in those defining moments of their own courage and confidence. What are you going through? What difficult conversation are you avoiding? If you can use this, great. If you have any questions, make sure you reach out to me, [email protected], that’s my email address. I’d love to serve you, I’d love to connect with you. This is a Behind the Scenes for Growth Think Tank. As always, lead with courage. We’ll see you next time.

Disclaimer: This transcript was created using YouTube’s translator tool and that may mean that some of the words, grammar, and typos come from a misinterpretation of the video.


Leadership Insights for Difficult Conversations



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