The business environment is always changing, and to excel, every leader needs to make ongoing “leadershifts” — changes that positively enhance personal and organizational growth.

Shifting from Pleasing to Challenging People is the Relational Shift. Great leaders challenge their teams to do better all the time.

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Perry Holley:

Welcome to the Maxwell Leadership Executive 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, a Maxwell Leadership Facilitator and Coach.

Chris Goede:

And I’m Chris Goede, Executive Vice President of Maxwell Leadership. Welcome, and thank you for joining. Right now, we’re in the middle of a series off of John’s Leadershift book. I did say shift, I-F-T. If you know John, I got a great story about this where I think he was on Good Morning America or something when the book came out and they had this massive sign that said Leader Shift, okay, I-F-T. He, on set, went over and stood in front of the F and held a book up and then I think Mark Cole took a picture and so it looks like… Well, I’m not going to tell you here on our podcast. Man, thank you so much for joining.

I want to encourage you as you listen to this, man, share this with your team. We have a lot of our coaches and our facilitators that have teams all around the world that will listen to this. We try to keep it around 20 minutes. Our producer, Jake, tries to keep us under 20 minutes, and then they take maybe the first five minutes of their team meeting and say, “What was your number one takeaway from the Leadership podcast?” You just begin to share that, so use this as a resource. It is a value add for your team.

If you have a question or a comment or maybe something you want us to cover for your team, we’d love to do that. Please visit, and you can leave that message there. Well, today’s topic is an intervention for Perry and I. This comes from my team, our team, and they asked us to talk about this, why leaders make the shift from pleasing to challenging people? There’s no doubt about it that if you’re wiring, as we’ve talked about before, is more of a level two in the five levels of leadership, the way that you would connect and relate to people versus a level three wiring, which, by the way, we all kind of go one or the other, where you are task focused, right?

You’re getting after it, KPIs, and… Well, like Perry and I like to say, you leave people in your wake and don’t care about them. This is a challenge for us on the relational side of things, of making this shift. I’m guessing this is where this is coming from, but I don’t want to make any assumptions here.

Perry Holley:

No, you’re right. I knew you knew it wouldn’t be an intervention because you know I needed this maybe worse than you. This is a shift many, many leaders will need to make, and it is that, Chris mentioned, we’re highly relational people. We like people. We mix it up with people and, from that, opens a door for me to be a pleaser, to do things that would be pleasing to others and to make you feel good about yourself and be very big. I’m big about encouraging others, but I’m not good or wasn’t good at challenging others. I heard John read this statement. He said, “You cannot lead people if you need people.” What does that mean?

Chris Goede:

Yeah, yeah. Well, listen, pleasing people is not the same thing as leading people. If you feel like you need people, you’re going to bend towards the pleasing side of them versus the leading them. I’ve also heard him say this statement. I think why we have so many statements from John on this is he’s had to work through this as well. He would tell you, if he sat down right here with us, which we need to have him on this conversation one time, this is something he’s learned a lot of lessons from.

He tells a story from his earlier years where he said that you could define leadership as make people happy and they will follow you. What he finally realized in all of his wisdom, now being 75 years old, was that he wasn’t really even leading people by doing that, by pleasing people. He was trying to make them and himself feel good. He was in the friendship business, not the leading business.

Now there’s a right way to do this. We’re not saying not to be friends and not to connect with people. As you think about this, you’re not just in the business of pleasing them, you’re in the business of leading them. I’m looking forward to kind of jumping through a couple of these shifts that we’re going to talk about and how to do this today.

Perry Holley:

What I often get asked is can you be a boss and still be a friend? I’ve probably done a podcast on that somewhere along the way about where’s the line? I’ve had CEOs tell me, “I don’t want to have relationship with my people because then I won’t be able to lead them right. Or they’ll take advantage of me or I don’t want to have that too close a relationship.” Here I am on the other side, I’m dying to have that relationship, am able to lead that.

I think what I’m learning is you’ve got to do the right thing for your people instead of what feels right for you. A couple things to make a shift. Number one was change your expectations towards leadership. You have to stop trying to be everybody’s buddy. That sounds obvious probably to a lot of people, but to me, I really was trying to be everybody’s friend. Instead, I need to ask myself what’s best for the organization? What’s best for other people within the organization? Then, what’s best for me? Not trying to be such a buddy-buddy, but really what’s best for the organization?

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Chris Goede:

Well, and I love the order that you just gave those to us, right? Because, at the end of the day, we are in a career, hopefully you’re in a calling that you feel is more than a career. I think it’s so important to say, what is the best thing for this team, for this individual, for you that would serve the organization the best? Then, I love what you said here, the second point, which is what’s best for other people within the organization, which leads me directly into the second part here.

Number two of how to make this shift, which is value people as much as you value yourself. Now, if you’re truly valuing people, you would give them, like yourself, you would give them your best effort. You would want the best for them. You would serve them. You would empower them. You would motivate them. Deep down inside, I think if we were all being honest, some of the greatest development times that we’ve ever had is where people were honest with us, where they did give us feedback that maybe wasn’t pleasing, but became from a leadership conversation.

By doing that, they valued you because of what they saw in you that you were able to learn from them. I think if you’d want that for yourself and the development for yourself, other people want that as well. They just don’t want to be your friends, so value them as much as you value yourself.

Perry Holley:

Oh, I love that. Another one, number three would work to establish expectations up front. For me, I can either set expectations and what are expectations of performance of our standard operating procedures, about how we do things, standards for outcomes that I’m looking for, do that up front and really have an understanding with people which really sets the tone, a business tone, that we’re here for purpose while we’re going to be friends and we can be friendly in that we have expectations.

Or, as I tended to do it early in my leadership career, was not setting expectations, letting things kind of unfold, having unstated expectations. Then, we have a big disconnect on the back end. I was just teaching that this morning with the group I was with, that if you don’t have expectations, people don’t know what… Are you setting expectations so they know what they’re supposed to be doing?

I was being so friendly. I didn’t want to put anything on you. I was trying to please someone and I didn’t think about it in those terms. I just thought, oh, I don’t want to put it on you, and then realized why we’re not getting where we’re going is I don’t have clear expectations with people because it seemed too harsh or something to me. I thought, no, I need to be clear what is I’m expecting of people.

Chris Goede:

It reminds me of, I think it’s Liz Wiseman who says, “Do the hard easy versus the easy hard,” right? Maybe if it’s hard for you to set proper expectations, I promise you the connection with the individual on the back end will be a lot easier if you sit down on the front end and set the proper expectations up front. I love that.


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Chris Goede:

Well, number four, ask yourself the hard questions before any potential difficult conversations you may need to have, and you may need to work at having hard conversations. We just did a podcast recently on difficult conversations. As a pleaser, I needed to learn to focus on the problem, not the person. This is a conversation about the problem, not necessarily the person and so where my motive may have been to make everybody happy, but to resolve the issue while maintaining the relationship sometimes is a little bit challenging there.

Perry Holley:

Yeah. That kind of leads up to number five, which is if a tough conversation is required, do it right. I know we just did a podcast a few weeks ago, so you can see that on how to have a difficult conversation. Really, for me, again, being a pleaser at heart is that I don’t want to, I don’t know, hurt somebody’s feelings or say something harsh, but that’s got to have the wrong motive. I didn’t have the right reason behind it.

Why am I having the difficult conversation? Think about those three questions. We always talk about John’s three questions every follower wants to know about you. Can you help me? Do you care about me? Can I trust you? Thinking if that’s my motive at the start was I’m trying to help you, I care about you, you can trust me, I’m doing this for you, then my difficult conversation’s going to be done the right way. I’m not doing it to try to win, be right, push you down or be overbearing or, in my pleaser style, not have the conversation at all because we’ll just let it go. It’ll probably be okay. It won’t be okay.

Chris Goede:

It won’t be okay.

Perry Holley:

No. I mean what’s my motive? Can I do it correctly and do it with the other person in mind? My motive is pure. I want you to win and I want you to improve, but we have something we have to talk about.

Chris Goede:

Love that. As we talk about number six here, going from this shift of pleasing to challenging people, man, understand this, what we call, the 25-50-25 Principle. This is where good leaders always challenge people to rise to the occasion, to become their best, to make sure we’re in alignment with where the vision of the organization is.

I was just on a meeting this morning where we were re-casting the vision for a certain project to make sure that we can get everybody rowing in the right direction, as you mentioned. What you’re going to find is that not everybody’s going to be rowing in the right direction or want to row in that direction. This is where this 25-50-25 comes in where 25% will support your efforts in where you’re going and what you’re doing.

50%, they’ll be undecided, they’re there. They’re collecting a paycheck. They’re along for the ride. Then, 25% are going to resist it and they’re going to push back. The challenge here in the shift that you’re working on of going from pleasing to challenging and leading people the proper way is that your job is to help that middle group, the one that are undecided, to move them to the first 25%.

I think any movement that you can create out of that will be beneficial to the values, the vision of where you’re taking the team. A lot of people, what do they do? They go right after the bottom 25%. They’re resisting. I got to get them on the boat, but you’ve… The middle 50. We talk about leadership being contagious. I think you got to understand it’s contagious both in the top 25% and in the bottom 25%. You, as a leader, got to go after that middle 50% to get them in that top 25% of [inaudible 00:13:03].

Perry Holley:

I think I speak for pleasers everywhere when I find it incredibly hard to believe there’s 25% of the people that don’t obviously see my amazing leadership. I don’t know. I don’t know who these people are.

Chris Goede:

Vision that you have, yeah.

Perry Holley:

I have no idea who these people are. Number seven and finally, before I let you wrap it up, is one of my favorites about balancing care and candor. We’ve taught this for years, that if you are a very relational person, you probably err on the side of care. We care. We care. We care. Not a lot of candor, straight talk. If you’re probably a more task based person, more analytical type, not relational, is not your strength, then you’re probably more candor. Candor, not a lot of care.

John says, “We want to balance those two because if you’re all care and no candor, it’s very dysfunctional. It’s not all rainbows and lollipops here. We’ve got hard things to do. If you’re all candor and no care, it causes distance between people because nobody wants to be punched in the face all the time.” If I’m thinking about how do I balance care and candor, it’s been a great learning for me to say, “I need to have the kind hard truth with people. I need to be able to say things, but I can still be myself. I don’t need to be pleasing, but I can be caring. I want to do that.”

Chris Goede:

Yeah. Listen, if you care for people, then they deserve to hear, in the right way, your candid feedback. As I close, two things coming to mind. Number one, Perry and I talk a lot about the five levels of leadership and we love that methodology. In there, we talk about level two being the connection, the relational, really the foundation to influence and we believe the success to your leadership.

If you do that the right way, whether it’s something you have to work a little bit harder on if you’re not wired that way or it comes naturally, if you do that the right way, when it comes time for you to have to lead in a crisis, in a challenge situation, people are going to buy into you as their leader before they buy into where they’re going, which will allow you to have those challenging conversations.

Know that. Know that if you go about it the right way, that while it may be hard for you because you think it’s challenging, they’re going to be grateful for those conversations. They’re going to completely trust you because trust is a currency to all leadership, and you need to understand that.

The other thing is that I just want to share with you as I close is that this is something that Perry and I have kind of laughed a little bit about as we’ve briefly given you some thoughts about this, to where we have talked about us being pleasing people but having to challenge, some of the greatest lessons that I’ve ever learned in my entire career, this even goes back to thinking about my high school football coach, was those that challenged me more than just telling me what I wanted to hear.

Perry Holley:

Boy, that is truth right there.

Chris Goede:

That is the truth, and I know it is because I didn’t like my offensive line coach very much at the time, but man, did I learn a lot of life lessons and a lot of football lessons from him, if that’s the truth, why would we not want that for everybody on our team? The right way, do it the right way like Perry talked about a little bit ago. Have that mindset to say, “Man, I value them so much that I want to add value to where they’re at.”

I cannot let this opportunity go by without talking to them about X, Y, and Z, without challenging them to do something a little bit more, achieve something a little bit greater, do something a little bit differently. If you got to have that self-talk, have that self-talk. Trust the fact that you’ve built the relationship the right way. There’s enough currency in the bank that when you have to pull some of it out and you challenge them, that it won’t phase the relationship. You can still be friends. You can still have that relationship, but yet lead them very effectively.

Perry Holley:

Almost quit a job once because the executive I worked for just… I couldn’t feel like I could do anything right. He kept challenging me. I shared with my wife. She said, “It sounds like he’s trying to make you better.” I went, “D’oh, he’s trying to make me better.” I had never worked for anyone who really took-

Chris Goede:

You took it personally. Right? You thought it was about you and… Yeah.

Perry Holley:

Yeah. He was actually trying to grow me and move me to my potential. He announced his retirement six months later. I went from quitting to crying, thinking, what am I going to do? I never had anybody invest in me this way. He was a nice guy and all, but he didn’t take it. He wouldn’t let me just make my way through. He pushed me a bit to do this, so yeah. Now I think back about all the leaders I’ve had, he’s got a great place in my mind.

Well, thank you, Chris. If you’d like to get the learner guide for this episode or learn more about our offerings, you can do all that at You can also leave a question or a comment for us there. We always love hearing from you, and we’re always grateful that you would spend this time with us each week. That’s all today from the Maxwell Leadership Executive Podcast.

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