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Executive Leadership Podcast #193: A Leaders Approach to the Difficult Conversation

June 23, 2022
Executive Leadership Podcast #193: A Leaders Approach to the Difficult Conversation

Many leaders are delaying or avoiding the straight talk or difficult conversations they need to have with people above them, below them, and beside them in the organization. Here are five steps to ensure your next difficult conversation is effective, healthy, and productive.

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Perry Holley:    Welcome to the Maxwell Executive Leadership podcast, where our goal is to help you increase your reputation as a leader, increase your ability to influence others, and increase your ability to fully engage your team to deliver remarkable results. Hi, I’m Perry Holley, I’m Maxwell Leadership Facilitator and Coach.

Chris Goede:     I’m Chris Goede, Executive Vice President with Maxwell Leadership. Welcome, and thank you for joining. Please take a second and visit If you’ll click on this session, this podcast session, you’ll be able to see a form there. If you’re interested in downloading the learner guide, if you have a question or a thought, or maybe even if you’re just interested in learning a little bit more about how we may be able to help the leadership culture inside your organization, you can submit that form there.

Well today’s topic is titled A Leader’s Approach to Difficult Conversations. We’ve been talking about confrontation the last couple of sessions. I encourage you, if you haven’t heard the last two, go and listen to them. We give you some tips and some commandments on how to have that. I think this is really a common theme of leaders that we deal with.

When people talk about, “Hey, what are some of the competencies that we need to improve on and work on communication happens to come at the very top?” They talk about having difficult conversations. This is one that we want to make sure you’re not delaying, that you’re not avoiding, that you have them when you need to have them, and that you make sure that this is something that you focus on in the moment.

Mark Cole, our CEO, talks about the fact that, “Hey, if you’re having a quarterly meeting with one on one or it’s confrontation or maybe it’s even your annual review,” which I hope you’re doing this more than just on an annual basis, “if you go into a team member and you have to have a tough conversation and they’re surprised by that conversation, it’s your fault as a leader.” And so, we need to make sure that you have the right approach and the right rhythm to being able to do that.

Perry, kick us off. I’m looking forward to the conversation today.

Perry Holley:    Yeah, thank you. We’ve been asked a lot lately, I’m always surprised people say, “Hey, can you help us with how to have a difficult conversation?”

Chris Goede:     Yeah.

Perry Holley:    I think that if we were just honest, most of us, maybe struggle’s too strong a word, but it’s a little bit apprehensive and it’s not fun. It is the harder part of leadership, but it is part of being a Level 3 production-driven leader is, you got to have hard conversations with people sometimes. I think it’s a skillset and timing and how to step up to it in a timely way, and it really can put you in a much better place if you have them, than it will if you skip them. So, I’m looking forward to walking through it with you.

Chris Goede:

You talk about coaching and conversations around this. I started smiling and thinking about even some of the conversations you’ve been brought in as a coach when these conversations are happening. They almost ask you to walk alongside them and to be a mediator in those difficult conversations, which is great. There’s a third party, and you can help coach them through that, both during and after. Yes, this is something that happens often.

Well, one thing we’ve talked about when it comes to this is the risk a leader has when you don’t have these conversations or you delay them. We talk about people are watching you all the time. We talk a lot about, at Level 3 in The 5 Levels of Leadership, to where this is your credibility as a leader.

Yes, at Level 1 you’ve been given a title, an opportunity to lead. Level 2, you are connecting and building relationships with people, but at Level 3, this is where your credibility is built, and it’s the production, and there’s a lot around this. I think that it will undermine your effectiveness at Level 3 as a leader unless you can handle these difficult conversations the right way. You’ll obviously eventually lose credibility. Your team members already see what’s happening or see certain situations that need to be addressed, and so as leaders, we want to encourage you to do it, but do it the right way.

Perry Holley:    Yeah, boy, that’s a really great point, that people know what’s going on. By you not stepping up just sets a whole dominoes. It’s going to be a mess if not.

The approach that I want to share here has really helped me personally because I’m a very, and you are too, we’re very relational people. We look at the five levels. We are very strong at level two, that building relationship and making connection with people. I really struggled in the early days of my leadership journey in confronting others, for fear that I would be hurting feelings or causing others relational challenges. That went against my personal values, but I realized it was hurting my entire leadership, my organization, if I didn’t.

The first step for me was really to establish kind of the… I’ll just call it the correct mindset. John teaches that… We mentioned him many times here that there’s three questions that every follower is asking about you. Those are, “Can you help me? Do you care about me? Can I trust you?” We talk about that frequently.

Before I have a difficult conversation, I use those three questions to put my mind in the right position about, why do I need to move forward? And move forward quickly with this was, I’m trying to help this person. I care about this person, and I want this person to trust me. If I can keep those things foremost in my mind, it really… If I don’t have that idea, I might be trying to win or prove that I’m right or put you in your place or push somebody down. None of those are going to be helpful at all. But if I say, “I really want to help you. I care about you. I want you to trust me.” Then it makes the focus on the other person and really push me in a great place to start this conversation on the right foot.

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Chris Goede:     Yeah. If the individual knows that those three statements that you made and the questions are true, no doubt about it, it goes so much more smoothly in that conversation. You need to understand leaders that I just gave you a quick example of saying, “Hey, the levels of 5 Levels of Leadership, by the way, level one, is that title level, two is really the connection with the individual where they want to follow you. They want to be a part of what you’re doing. That’s the foundation of leading somebody.

I think if you do that right, if you set that right, then what ends up happening is when you have to have those tough conversations, they’re going to know your heart. They’re going to know where you’re coming from. They’re going to trust you, by the way, and trust is a currency to all leadership. That has to be there before you can have these types of conversation. When you do that, and you go about building your influence the right way with the right motive, when you have to have those conversations, they will go a lot better and you will be positioned in a way to where they will receive it and know the motive behind why you’re having that conversation.

I think it’s critical, just to make sure that we back up and say, “Yes. You got to have these conversations. There’s no doubt about it.” But the work that you need to do before these conversations even become relevant as that person’s leader and influence is so important.

Perry Holley:    That is exactly right. I think if you’ve been operating as a level one leader, which is I’m the boss, then your influence is only as deep as your title. But if you’ve done that hard work of five levels and growing your influence with those above you, below you, beside you, your conversation, difficult or otherwise will be much easier, I think.

You hardly ever think about that is, “I’m having trouble with conversations with people because of my low influence with them.” That’s something we can fix and work on that.

Chris Goede:     That’s right.

Perry Holley:    After mindset, the second thing I start to look at for me, and again, I just confess, this was a struggle area for me was, I want to focus on the outcome. I remind myself, I’m not trying to be right or win, and I might even actually write down what is my desired outcome for this conversation? What would a win be for me and for the other person? Why are we doing this? What do I hope at the end of the conversation? What do I want people to think, say, and do based on what we’ve talked about?

Once I got the right mindset, help, care and trust, and I’ve got the clear outcome, I’m well on my way to having a pretty solid conversation. It could be difficult, but it’s got meaning to me.

Chris Goede:     I like what you said. Let me back up just a minute. I like what you said about the being right. I think it’s so dangerous. If we’re going into these conversations, thinking we are 100% right and trying to prove that we are right, that’s a dangerous place to start the conversation from, because I think it’s just going to have a bad outcome.

Sometimes we use the statement of, “Hey, let’s not try to be right but rather let’s focus on doing right.” So many of us… While we might be right, they also might be right, and so doing the right thing is going about this the right way.

That’s a lot of rights, if you’re writing these down, that was spelled differently. The last three words that I said.

But anyway, if your desired outcome in mind… If you have a desired outcome in mind and you want to be right, I’m going to challenge you to let that go. You got to get that story out of your head and you really have to be curious, going into these conversations. You really have to want to understand their perspective in order for it to be a very healthy confrontation, a healthy conversation.

Perry Holley:    Yeah. Well, if you win and they lose, you lose.

Chris Goede:     That’s right.

Perry Holley:    You’re going to disengage them. You’re going to push people away. You’re going to cause all kinds of other… I’m not saying it’s not going to… It’s going to be hard, but they don’t have to feel like they lost. It could feel like you cared about me and your influence is high with people. They actually don’t want to disappoint you.

Chris Goede:     Yeah. That’s right.

Perry Holley:    Really a great thing. After I got my mindset and I’ve got my outcome to find, another place I would go is to do some kind of thinking through, reflecting on what kind of emotion this conversation might elicit from the person I’m speaking with.

Now, I can’t control their emotion, but if I put myself in their position and consider the possibilities, I think I feel better prepared that I won’t risk being surprised. I think the worst thing I can do is go into a conversation thinking that’s no big deal and the other person falls apart, and now I fall apart. I want to think through what could be the emotion that’s going to come from this and can I be prepared for that? And even put myself in their shoes.

Chris Goede:     Yeah. I think you’re spot on about that. What I think we’re talking about is this, how empathy plays a role in these conversations. That has to be part of your strategy. When you enter with that mindset, when you enter with the empathy of having these conversations, then your tone, your demeanor, your body language, everything changes.

We talk about how leadership is contagious and your behavior is contagious. Your tone, your demeanor, your body will absolutely communicate one thing to them. It goes back to the three questions that you posed, that you definitely want to help them, that you care about them and that they can trust you, that’ll be contagious. I think what ends up happening is that gets reciprocated, reciprocated back to you in that conversation, and so it’s very important to go into that confrontation with that type of posture.

Perry Holley:    Yeah. Love it. Well, I think about my mind’s the outcome, the emotion, probably the final thing that I’m want to consider when I’m going into this kind of a conversation is, what kind of resistance might I encounter? What will be the other person’s reaction to the topic? Are they going to…

I’m going to give a warning here as well, if you’re talking to someone that you have a relationship with at home, in the community, at work, you kind of have a movie, a story running in your head about them as a, “Oh, Chris, he always does this. Oh, Chris, he always…”

I’m telling myself this story. I’m thinking, will they deflect? Will they make excuses? Will they try to blame someone else? I kind of already have an idea because of my relationship with that person. I want to be careful about running the story. I want to be open to what’s really going on and what’s really happening there, but I also want them to take responsibility in the conversation.

I spent a few minutes just considering what direction they might go, so that I can be prepared to comment as appropriate. If I’m sensing deflection or blaming or making excuses, I want to be able to have a response for that.

Chris Goede:     Yeah. I love that. I love thinking through that. The key point here that I think Perry’s making, I want to make sure that we’re aware of is to, you can have a plan and you can prepare, and you can have a plan, but don’t script the conversation, right?

Think through it, have a plan, but then let it be very organic and do it in a way that’s very honoring of the other individual. Remember we’re going after the behavior, not the individual.

As I wrap up, one of the things Perry, I’m proud of you. You didn’t mention that there was five points here. All five.

Perry Holley:    Surprise.

Chris Goede:     Yeah, you kind of got me. I was like, “Well, how many are we going over?” But there’s five of them. The mindset, the outcome, the emotion, the empathy, and then resistance as the last one.

I love what Perry said is, don’t frame things up in your mind. It doesn’t need to be more difficult than it is. I think it’s okay to understand that you can be candid and be respectful in these types of conversations. Foster dialogue, when you’re having it. This is not a one way conversation.

I just go back to this thing where… Make sure you understand the confrontation style and index of those that are on your team. We talk about the importance of understanding how people are wired, their learned behaviors and their values. Well, part of how they’re wired is their confrontation style and their index.

We use an assessment with leaders for that. If you’re interested in that, Perry, you’ll kind of wrap us up with, again, the location where you can download or submit that form, or you can request, and we’ll send you some more information about that. Because I think that’s really important because it’s going to be different for everybody.

If Perry and I were having a conversation, it’s going to… confrontation’s going to be different than if myself and Jake were doing it, or Devon or anybody on our team. We got to be aware of that going in. And to Perry’s point, you got to have a plan. You got to think through it, just don’t script it and then follow that script because it’ll be obvious that you’re not listening to anything that they’re having to tell you.

Perry Holley:    Right. Fantastic. Chris, thank you. As Chris mentioned, if you’d like to leave us a comment or a question or learn more about our offerings, you can do all of that at You can also download a learner guide, would have this information in it today. We hope you’ll do that. We always love hearing from you. We’re always grateful, you’d spend this time with us. That’s all today from the Maxwell Executive Leadership podcast.

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