How to have hard conversations as a leader

Jan 21, 2022

How do you have hard conversations? As a leader, how do you draw that line between compassion and expectations to help people see where they need to step up? 

It's challenging and can be difficult, especially if not done well. I think it comes down to reframing your mindset and going into the conversation knowing what your intent is. Also, just acknowledging that this is a hard conversation to have for both parties.  In this post, I'll share my top 5 recommendations to help you hold hard conversations that strengthen your relationships and your team.

Know what you want to accomplish with the conversation 

All of us want to be the best that we can be, have the best conversations, and always do our best work. The reality is that we don’t always hit the mark. Our intentions are always good and sometimes the situation doesn’t turn out as expected.  

It’s time to have hard conversations if we're not meeting expectations, we're not honoring agreements, we're dropping the ball, or if there’s a repeated pattern, and we're showing up looking like we just don't care.  

That’s when I go back to the purpose of the conversation. As a leader, I want my team members to be successful and be the best version of themselves. I want to help them, and sometimes that means helping them see something they need to change, even when it’s hard to say and hard to hear. 

Make it about solving the issue, not a value judgment about the person 

It’s so important to keep the conversation about the issue. It's never, “You're a bad person for making this mistake.” It can feel personal, because you're being talked to about something you need to improve, but needing to improve something does not make you a bad person. We all have things we could do better. 

As a leader, you must set the tone and expectations for the conversation, and it's not always easy to do. For me, it goes back to a lot of reading, blogs, and role-playing conversations in my head and practicing them aloud. I'm always thinking, how can I set this person up for success so that when they come out of this conversation, they understand my expectations, they understand where the issue came in, and why it's unacceptable? And, they feel like, “You know what? I can own this. I can do better”. I don't ever want anyone to come out thinking, "Well, I'm just incapable. I can't live up to that”.  

Remember who owns the outcome (hint: it isn’t you) 

The other piece is that, as a leader, you can't own the outcome. You can't take responsibility and accountability for acting on the resolution. That must go to the person you're talking to. That’s who must buy into the solutions, to make suggestions and own what they're going to do better.  

That's a mistake I've made before where I said, as a leader, I'm going to make this rule and I'm going to make sure you follow it by checking in and monitoring. That's not helpful and it's not setting somebody up for success, because that just means I took the accountability, and in doing that I really shortchanged the person by not giving them the opportunity to step up. 

Choose your timing 

When do you find a hard conversation that needs to happen? I generally choose to have those conversations when I see a pattern. A lot of times, if the same issue keeps coming up, there's a problem where somebody didn't get trained. They didn't understand the process. My assumption is that the person is capable, and clarity is needed around the process or, the process is so clunky that they can't do it.  

So I look for the pattern, and then I also look at the level of the issue or mistake. If you cross my company core values, we're going to have that conversation quickly and understand that our core values are part of our DNA. If it’s something that affected a customer, the conversation focuses on how critical is that impact, how quickly can we solve the problem, and when do we have a clear view of the whole scenario so that we can see where the ball dropped and how to prevent it from happening again. 

I also try hard to make sure the person I'm talking to knows that I care about them as a person, and I care about their success. And I recognize that it's uncomfortable for me to have these conversations, but if I don't have them because I’m uncomfortable or I don’t want to make someone else uncomfortable, that's not fair to anyone. 

That's where you get your growth, growth comes from being uncomfortable. 

Tressa McLaughlin

It also takes practice to get good at finding the right time frame. Don't have a hard conversation when you’re angry, and you can't see your way to the solution; and don't wait so long that it doesn't feel important anymore. 

Keep your mindset in the right place 

Mindset is about staying present with the intent of the conversation. If I find myself drifting out of that sweet spot of intent, I start asking more and better questions so I can clarify where we're going. 

I also start the conversation by calling out the uncomfortable feelings first. I find that when both participants can name the feeling, we have a better outcome.  I might say, I want to talk this through so that you and I come out on the other side feeling good about the resolution, then we can both identify and honor our parts and agree on how we'll move forward. That sets my mindset on what I'm intending to do.  

If it gets very subjective and there is blame shifting and finger pointing, I ask myself first and then verbalize the question: I understand that happened. How does that contribute to your ownership of X, your execution of Y? Keeping my own mind focused on finding a solution helps me pull the conversation back toward its purpose. 

Hard conversations shouldn’t always be leadership-to-employee. There is value when cross-teams and peers are adept at having hard conversations. I have seen great process improvements happen when we can roll up our sleeves and respectfully debate. And crucial conversations aren't always negative. Sometimes you throw an issue on the table that isn’t working and just hash it out until you get to a better point.  

The point of having these conversations is enacting change quicker, creating clarity for your team and having the right people affect change. It’s part of being a good teammate, being engaged and showing up! 

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