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Tough Conversations


C: Welcome to  Slingshot25’s Shotcast, a series of bite-sized podcasts that will feel like an espresso shot to your brain. I’m Courtney.

J: And I’m Jackie.

C: Something we’ve been thinking about. We say it a lot on here, like change will get you into a mess and leadership will get you out. And one of the areas that there’s a straight up overlap between change and leadership is tough conversations. Because when things change and we’ve made decisions that are going to impact people, and they’re going to lose things, all of the sudden it becomes whack-a-mole for tough conversations. They’re popping up and we don’t want to talk about them. We don’t know the answer and we’re scared of what people are going to think. And, oh by the way, we’re insanely vulnerable because I don’t know the answer to the question so let’s just avoid it.

J: Well that’s news to me. I thought people love tough conversations.

C: They love whack-a-mole.

J: Oh, maybe that’s where I confuse them, everyone loves a good whack-a-mole game. 

C: So, when you think about it. Change really sets us up in this place of just wanting to avoid almost every conversation. Because we know our people want answers, and we don’t have them. We know people are losing things and we’re uncomfortable addressing that. And, oh and by the way, change triggers emotion and let’s just avoid that completely. Altogether, it’s just a great recipe for tough conversations and our desire to avoid them. So, Jackie, will you talk us through a little bit about people being avoidant of those conversations and what people should think about it?

J: Let’s do it. So you’ve already mentioned a really important word there, Courtney, and that is the word emotion. There’s really, if you really think about it, the only difference between a tough conversation and any other kind of conversation is emotion. So let’s just start from there. That’s actually the thing that keeps us sort of dancing around tough conversations. We’re afraid that things are going to go ugly. Someone’s going to get mad. Someone’s going to cry. Someone’s going to be upset in some fashion. 

C: Let me interrupt you for a second. I’ve been thinking about this a lot lately. I’ve been talking about loss management. If people didn’t lose anything, we wouldn’t need change management. 

J: That’s right, same thing right yeah we like to sort of classify in terms of our challenge with tough conversations is there is an aversion to tough conversations. An aversion meaning…I don’t really like it. I would just as soon be doing something else thank you very much. So there’s an aversion to having tough conversations.  We just pretend we aren’t going to address that and we just go on our way and usually what we’re doing at the time we’re avoiding them… is strategy. Of course, we’re joking that is not a great strategy. So no one leaves here, no one turns off stop right now and think that’s the end. 

It doesn’t take a genius to figure out that the most problematic one is avoidance. Simply not having the conversation is the much bigger problem. And so that leaves us with aversion. And here’s what I will tell you about aversion to tough conversations –  it’s completely normal. Like I often will make a joke if you wake up in the morning and realize that you are so excited to have a tough conversation loaded with emotions, that might be the day you realize you’re a sociopath. We’re not really designed to put strain and threat inside our relationships with others. And it’s really human beings who are wired to do just the opposite. So these tough conversations – we all just need to realize it’s okay that I don’t really enjoy doing these things, and it makes them make me nervous, they make me sweat a little bit, and and they make me you know get a little bit tongue tied. All of that is a normal reaction to having a tough conversation.

C: I think the other thing to remember is that when things are changing we don’t have the answers, we tend to jump to a conclusion out of fear. Or maybe our histories that whatever’s happening is going to be bad. And it’s very difficult to engage in a conversation with people because we don’t want to ask them questions and have them you know show us their emotions. Or we don’t want to ask them questions and what if I ask them if they’re doing okay, or if I ask them what do they need. What if they ask me for something I can’t give them? There’s a million scenarios where every time I try to be empathetic or check in with my people, it triggers a lot of fear about not being able to serve everyone’s whim, not just not knowing. 

J: Yeah absolutely. And so our advice, you can in a nutshell, there’s a lot to unpack here around tough conversations. Stay in or lean into, as Sheryl Sandberg would say, lean into a headspace of curiosity and empathy. And I’ll add one more; I’ll add humility into the mix. Because if you all remember the definition of humility is not thinking less of yourself it’s thinking of yourself less so the approach that we teach to tough conversations is just to get out of your head. Just get out of your own head and lean into that curiosity and that empathy. Keep yourself focused on the other person. You are in service to the other person at this moment. And to keep wondering, what might they be thinking and feeling? I don’t have to own it, I don’t have to necessarily solve all of that. Because, frankly, this isn’t about me. And if you can stay in that moment of sort of a deep sense of curiosity and empathy and humility and then believing in the resilience of another human being. That’s probably the best sort of mental approach that you can take to a tough conversation.

C: I’m going to talk a second about the tough conversations course that you’ve mentioned a couple of times. Part of the learning experience is that people do experiments to practice empathy. And time and again, the feedback from the leaders who were brave enough to practice. They said  they didn’t need me to solve their problem. What I think people really just wanted was to be heard. and in that full circle moment you don’t have to be afraid of being able to answer the question, just be there for people and then surprise yourself about that enough. 

So, yes we do have a Tough Conversations class it’s called Tough Conversations that Move People Forward, and we’re very excited about what we are able to teach in that class. This is this is a skill that avoidances doesn’t have to be the only option and we can teach you how to have these conversations of being productive and showing up for your people.  

That’s all for this episode, but we always have much more to say. If you want to talk more, drop us a line at

Until next time. 

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