Skip to content

Maxwell Executive Leadership Podcast #127: Making the Relational Shift: From Pleasing to Challenging

March 11, 2021
Maxwell Executive Leadership Podcast #127: Making the Relational Shift: From Pleasing to Challenging

Some leaders find themselves caught in a pattern of pleasing others versus leading others. Pleasing does not equal leading. To lead, you must challenge others to a higher level of performance. Today, Chris and Perry discuss ways you can move past the tendency to be a pleaser, and challenge each person on your team to take your business to the next level.

Want to enhance your organization’s leadership culture? Learn more about our 5 Levels of Leadership private workshops HERE – Offered virtually and on-site to meet your organization’s health guidelines.

Download our Learning Guide for this podcast!

Read the Transcript:

Perry Holley:    Welcome to the John 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 Holly, at John Maxwell, facilitator and coach.

Chris Goede:     And I’m Chris Goede, Vice President of the John Maxwell company. Welcome, and thank you for joining. As a quick reminder, before we get started. If you want to download the learner’s guide that Perry’s created for us, you want to learn a little bit more about some of the virtual content that we’re delivering for teams, or we even, there’s a link for a weekly blog that ties to some of the podcast topics complimented, that Perry writes. If that interests you at all, please visit There’s also an opportunity for you to leave a question or a comment-

Perry Holley:    Please do.

Chris Goede:     And we would love … Yeah, we absolutely love to do that. A matter of fact, just this week, we received a couple of comments from some previous podcasts. We’re able to get them some additional information. We would love to serve you in that way. Well, we’re in the middle of a series where we took a book that John wrote called Leadershifts, and we focus on the culture of your organization, the culture of your team, and of which the environment you work in and what that feels like, what that looks like. What’s the communication. And so Perry wrote four lessons to where we took for the shifts. And we’re really talking about how do we do these well, what does this look like in order to improve the leadership culture? I always give Perry a hard time about these topics and these titles, and there’s no doubt about it that he and I are wired similarly, and he observes my leadership and he’s part of team meetings and is getting more and more involved in what we’re doing. And I’m like, Oh, this might be at me directly.

And today’s topic is making the relational shift from pleasing to challenging. And the reason I said it might be about me and Perry and I have a similar bent. So I can say this is that we both tend to be on the people pleaser side, right? We both want that level to connect and relate and that can’t always be, and we need to make sure that we have a great balance. Was it about me Perry or where were we going? What was the topic around this that you said, man, we got to talk about this ?

Perry Holley:    We’re moving from podcast to intervention right now so please sit down. This may take a minute. No, this one hits a little close to home for me. And as I mentioned in the last podcast, the subjects I picked for this series are the ones I hear the most on our coaching calls that we do. We do a lot of that and these come up quite a bit. And then I had to cringe because this was a big one for me. And then now you’ve confessed for you to. I am a natural born people pleaser. My right path is networker. I’m looking to engage with people and I’m finding ways to make people happy with being around me and that sort of thing.

When I first became a first-line manager in the early years of my progression after being a sales guy and becoming a first-line sales manager, I had these 11, I’ll never forget these 11 people that I took it as my mission to make them happy. But pleasing does not equal leading. Do I want them to be happy? Of course I do, but that’s not why I’m here. Do I want to please you? Of course I do, but that’s not why I’m here. It’s not my job. I know you, and I share that as you, as you said, the level two of the five levels, that relationship bent, but have you ever struggled with the pleasing gene?

Chris Goede:     Yeah. There’s no doubt about it. And there’s a couple of things that come to mind. Number one, as I’ve learned, the longer that I’ve led, it’s exhausting at times.

Perry Holley:    It is.

To be a Successful Leader, You Need Feedback on Your Leadership.

We’re excited to announce our new and improved Organizational Effectiveness Survey (OES). The OES gathers feedback from employees to give leaders and management the knowledge and action plans needed to develop a more effective and productive work environment. Our new version measures 4 areas of your business: Leadership, People, Strategy, and Performance. 

Chris Goede:     Right. Like let’s just be honest, although that’s a natural bent for me, that’s not a natural reception of everybody else, if that’s the right way to say that. And so I find myself at times and having the past of spinning my wheels and it just draining a lot of my good energy that the rest of my team members needed from me, but yet I spent too much energy on the other side of that. The other thing is I’ve learned that we talk a lot about with organizations around their turnover and retention and everybody deals with it a little bit differently. And I’m always so fascinated because people that are in the people pleasing business … Let me relate it back to the five levels of leadership.

We talk about the fact that in retention of people, you’ve got to go through this process of influence where we see a high turnover is people go from level one to level three and it’s like, hey, I’m the leader, I’m in charge. Now we’re going to start producing like crazy. And I’m going to run you over. And that department, that leader tends to have a pretty high turnover in-

Perry Holley:    By skipping level two.

Chris Goede:     By skipping level two. The area that we need to be aware of as if we’re pleasing people and we get stuck at level two is we just sit around and we like to say, just sing kumbaya together. And we never get to the production level.

Perry Holley:    We hang out at level two.

Chris Goede:     We hang out at level two, because we want to please everybody. We want to have all collaboration and not only do we want to have alignment, we want to have agreement with everybody in the room. And so, yes, it’s something that I’ve struggled with, but it’s a danger zone for those. And it’s been a danger zone for me. And I know you can tell war stories and not only in your personal leadership energy, but also for the team and your credibility as a leader.

Perry Holley:    Yeah. I figured you’ll come in one day and said, what happened to Perry? We all liked him so much. Yeah, you got fired. He wasn’t producing results, but everybody loved him.

Chris Goede:     That’s right. Yeah.

Perry Holley:    When I think of the question, whether am I pleasing or leading it often comes down to ask the question, am I really trying to just make myself feel good in the position of a leader? And I had to learn to kind of separate, what’s good for me from what’s good for the people and what’s good for the organization. And really it is a shift in your mind that I’m not here to make myself feel good as a leader. And like everybody patting me on the back, I’m here to make a difference and lead us to the place and get everybody working at their strengths to take us where we need to go. It sounds easy enough, doesn’t it?

Chris Goede:     Yeah. I was having dinner with a leader that I respect recently and we were talking about culture and someone that’s in their people management side of their business, we were talking about one of the areas of growth this individual needs in their leadership is they do an incredible job of listening, but they don’t do an incredible job of then coaching and empowering and challenging some of the things that they’re hearing to align with the culture of the organization. And we got down to this topic of saying they listen because they want to please the other individual, they don’t want to rock the boat. They don’t want to cause any … And yet what’s happening is although that’s easiest for them.

They’re not necessarily getting the best out of the organization. They’re not getting the best out of the people, they’re just listening and maybe being empathetic, which is great, but then not taking it to the next step. They’re just doing it because they want to be liked, they want to please by saying, oh, I totally understand. I totally understand. And you need to do that. And have empathy, but you got to make sure that you’re also then helping instruct, empower and coach at times that may not be comfortable to share may not be pleasing to them or to your leadership.

Perry Holley:    When John says, moving from pleasing to challenging, how do you view challenging?

Chris Goede:     Yeah. I think the challenging is that, they understand that you heard them, but then if there’s anything that you feel like contradicts what they’re saying versus your perception of it, the situation, or maybe even the organization or the people or you, or your leader, that you have a conversation about that. Because oftentimes I’ve found myself in the past wanting to please you in a conversation. And I just agree.

Perry Holley:    Yeah. And not challenging-

Chris Goede:     And not challenging because I’m agreeing, they leave my office and they’re like, oh, well I am … that’s right. That’s the way .

Perry Holley:    We must begin at an agreement.

Chris Goede:     We’re in agreement. Yeah. So John also says, “To get the best out of people, leaders must ask for the best from the people.”

Perry Holley:    Right.

Chris Goede:     Versus just listening in to them. And so I think as we talk about this challenging part, and I just mentioned it briefly, but I want to make sure that you as people inside of organizations, we’re talking about cultures and shaping leadership cultures, your motivations ought to be the people and then you. And that means you being third. You’re going to be uncomfortable and not pleasing everybody in every situation.

Perry Holley:    As you’re talking, I’m thinking of the word consensus pops into my head, is that I think for years, I thought consensus, if I could get the consensus of the team I was leading and that’s, I think true for a lot of people pleasers like me and I guess you. That sounds like a good thing. Can’t we just all agree and that’s not why I’m here. What I found, if I could channel my inner level three, which is difficult. I mean, I’m really good at level two, relationships, level three, results and driving the team that I think we’re leadership credibility is born is at level three. I struggled with it a little bit. What I’ve found is instead of going for consensus, I need to share a vision, make sure everybody knows where we’re going. What are we trying to accomplish?

Maybe set some expectations, not maybe. Set some expectations for how we are going to get there. What is it I expect? Challenge others on getting there, find out how they use in their strengths. What do they need? Raising the bar, that change agent attitude of, we can do it a little bit better. Can we do it a little bit better? Show the way you mentioned this quite a bit about, am I demonstrating? Am I modeling the way? Am I out in front? And then ask for commitment? John says a lot about that, if you don’t ask for the commitment, you’ll end up with some uncommitted people and you really want to have this commitment. When I think of these things about vision and expectations, and challenge, and raising the bar, and showing the way, and asking for a commitment. That’s not a pleasing person’s easy walk right there. That is actually leadership.

Chris Goede:     No, but if you do it with a proper intent behind it, ultimately it can come across as pleasing. I think if there’s a balance that you’ve got to get to as a leader to be able to understand this. I liked the last one you were talking about, about ask for the commitment. Because I think that’s probably of the lists that you’re like, oh, how do I ask that of them or for them? But I think that’s important when we’re talking about employee engagement and we are having conversations with people to go ahead and ask for their commitment, whatever the situation may be. It may not be that, that’s something they want them to do. It may be something that you need them to do again, that is contradictory to the pleasing side of things, but we need to lead them.Perry Holley:    Yeah. Give me an example. I know you’ve got a team that you lead and you got a lot of things going a lot of different burners. You’re juggling things. How do you, do you just say, can I have your commitment or do you use those words? How do you sense whether you have commitment or not?

Chris Goede:     Yeah, I don’t use necessarily the word commitment, but I will say things like, “Hey, can I count on you for this?” Or, “Hey, will you take this journey with us?” Or, “Hey, are you willing to step up and lead the team?” I’ll use words like that versus saying, “Hey, can I have your commitment in that?” But I use the words in saying that I want to empower them. I want to let them know that, I need them to lead in this area. I need them to step up. And I think when you do that, because I know when I received that, it fuels me, empowers me. It gets me excited to be a part of that versus me just saying, “Hey, I need your commitment.” There’s ways in your own language and how you communicate. I want you to think about that of saying, how would you ask for commitment in your own language, your own leadership style, because you don’t want it to be awkward and you don’t want it to come across as-

Perry Holley:    Please sign here.

Chris Goede:     Yeah, please sign here. Like you’re doing a new or used car transaction.

Perry Holley:    Are there things you hear that … are there triggers or signs that you don’t have commitment that you look for, are you… I mean, are you with me or can I count on you? But what do you see back that makes you concerned?

Chris Goede:     Yeah. Body language is big. Questions about what we just talked about, the way they ask the questions, the questions that they’re asking lets me believe or see into that. And here’s what I think is important. Not everybody is going to accept that commitment.

Perry Holley:    What?

Chris Goede:     Yeah. I don’t understand it either. But I mean, I’m this incredible leader everybody should. But it’s okay if they’re not, maybe that’s not the right journey for them. But as a leader, you need to understand that. And I would almost challenge you as leaders to say, if you get into a situation with a team member or somebody you have influence with, and you’re needing to ask for their commitment and they don’t necessarily buy in, I’m going to challenge you that you didn’t know them well enough in the first place.

Because you shouldn’t be surprised by that. You should, as a leader, see further than they see and you should know as much about them as you possibly can. And so you shouldn’t be surprised if you ask somebody to take a commitment that they say no to you, because you probably should have known ahead of time that maybe it wasn’t the best fit for them. Maybe you shouldn’t even have asked the question, but I think it’s okay. I want to make sure I’m very clear on this. It’s okay, because you don’t want them just pleasing you by saying yes and not doing it.

It’s okay to allow that pushback. And for them not to have a commitment in that journey and maybe that’s a different journey. Maybe it’s a different opportunity inside the team. Maybe as you begin to have conversations, it’s not the right team fit for them. And you got to be comfortable with all those uncomfortable conversations. And half of you that are listening to this, you’re like, oh, I love those conversations. And then the other half are like, well, I’m more on the level two, the people pleasing side. And it’s a little bit harder for you.

Perry Holley:    Right. But I like having, if you team pretty well, you’ll know that there’s generally I’m thinking right now, specifically of a team I led where I knew there was one person that was always going to back push back, but I learned that they had a different perspective and that I should listen to that and then make my decision and move forward and ask them not, here’s where we’re going, are you in or out? And that’s okay. There’s things, I don’t know everything. . What am I not seeing? I like knowing … There’s some people that always agree and go along, but I like the little bit, having the permission to dissent if you dissent and helped me be better. But at the end, I need to make that decision. I’m not trying to here to please you again, I’m here to challenge us to go to the next level.

Let me share a couple of tactics that we’ve used to help. And I know that we do some coaching a lot, to move beyond pleasing to leading, maybe if you’re listening today, you can find a couple of action items. A number one for me is just valuing my people as much as I value myself. That moves me away from pleasing and toward serving, empowering and motivating, but really putting the value on them. Just like I’m saying, I know some people are going to push back. I value them and value their input and they may show me something that I don’t know. I’m not just here to make myself feel good. I want to value you and your relevance and my need of you on the team.

Chris Goede:     Well, I really love the fact that you just changed the focus, even from the leader, about pleasing the leader. And it’s really about the team. And I think ultimately if you can get to that collective language, the more often that you share that, I think the more successful you’ll be at that. There’s also this thing, John talks about the disappointment gap and he talks about its difference between the expectations that were set and communicated in reality. And the number one, I almost, probably two times to number two, the competence that we’re asked to come in and help with is really around communication. And I think as a pleaser, you got to make sure that you’re setting the proper expectations up front, like what you’re expecting from them in the conversation and the communication and not telling them, what they’re going to get into return. Obviously I was like, hey, here’s the expectation I want to communicate, this is what I expect from you. And-

Perry Holley:    I just had a question, I think it’s … Okay. I just had a conversation yesterday and I asked the team, do you set expectations for your team? And I get this really awkward silence about what does that even mean. What kind of expectations do you ask for? How do you do that?

Chris Goede:     Yeah, here’s a couple of areas that I think I want to challenge them with these expectations. The personal performance, hey, here’s my expectation, communicate this. Perry, this is my expectation of you personally. I want you to perform this. This is my expectations of your personal growth. That’s an expectation that we have on the John Maxwell Company, you are going to have a personal growth plan. Another one is, I’m going to empower you. I’m going to communicate say, “Hey, listen, this is something that we’re going after as a team, I want you to take this. I need you to lead this.” And I’m going to empower you to be able to do that. And by doing that, I want you to take ownership of it. And I’ll deflect at times, do teammates come and say, hey, where are we at with this? I don’t know, talk to Perry about it, because he’s leading that.


Perry Holley: Oh, you did that this morning. I saw you do that with, somebody asked a question, you said, go ask that person-

Chris Goede:     Oh, I did.

Perry Holley:    And then come back and report to the whole team. That was really good. Wow, thank you. This is real time, live stuff. Keep talking about the good stuff. Don’t talk about the bad stuff.

Chris Goede:     And then finally, I just communicate that, hey, I’m going to hold you accountable to it. I’m being held accountable by Mark Cole for running this business. And I’m going to hold you accountable for running this. And I think if you have those conversations, they don’t have to be those exact five items that we just shared with you. But there’s got to be a system that you have. When you’re in the people pleasing side of things, develop a system or process that allows you to build some learned behaviors to be able to have some of these conversations.

Perry Holley:    The first tactic was value the people more than you value yourself, value their contribution more than you value your own comfort. The second one you just gave really good, communicating expectations. A third one that I’ve used that I had to really step up too, was stepping up to the difficult conversation, the crucial conversation, the difficult conversation is not a natural place that a pleaser likes to go. We don’t really … I don’t really mind being in conflict, but I don’t really want to initiate conflict. It’s not a natural bent for me. And a tough conversation seems like a way for conflict to occur. Maybe I’ll just avoid that. But it goes back to, what I said earlier. Am I really trying to protect my own comfort? Or do I care enough about someone else to tell them the truth?

John gave a great, this was one of those throwaway lines I almost missed, but I go back to it time and time again, especially when I, as a pleaser, have to deal with a tough situation. And John said, “You’ve got to balance care with candor.” And if you’re moving from level two to level three, in the five levels from relationship to really getting driving results, that’s going to naturally call out the challenger in you. And it’s going to really squash my inner pleaser as painful as that sounds. But if I can balance care and candor, it’s going to allow me to challenge the team to meet the expectations, but I’m going to do it in a way that shows that I care about you, but I need to have this tough talk with you.

Chris Goede:     Those that have listened to our episodes in the past, they’ll remember this phrase, this intent versus perception gap that we talk about. And when you go from pleasing to challenging, I think this is incredible language for you to be able to use, to feel comfortable having that conversation. And that is, hey, I know your intent was not to this, but the perception that I have right now as your leader or the perception the team has, can we talk about this? Make that statement as an opening to the conversation that will allow you to then naturally challenge them. And to your point, sometimes it’ll allow you to have good candid conversations while doing it in a way that shows care to them because of the language and the words that you have chosen. Because so many times we get hung up on words that were said, or the tone behind what it was said as leaders. And so just know that you can challenge in a way that still shows care and appreciation for those that-

Perry Holley:    We assign intent. I mean, I don’t know sign it based on something. And then now we’ve got a problem.

Chris Goede:     Yeah. You know, John taught this principle about this, he he’s always gotten numbers tied to all kinds of things. We all talk about the 10-8-10. There’s one that he taught that is the 25-50-25 principle. And this is fascinating because as a leader and as a people pleaser, I go about this a little bit differently, or I did before I understood this principle. And obviously John is right. And so I default back to that, but when you’re leading change, you’re leading teams, you’re leading through disruption, maybe pandemics, whatever it might be like-

Perry Holley:    There’s an example for you.

Chris Goede:     All of that, that is real as leaders, we’re going to feel resistance. And as people pleasers, we don’t like that, we get uncomfortable with that. And so here’s what John says. John says that 25% of the people will be with you. I’m like, yes, there’s 25%. Then we have 50% of the people that they’re kind of undecided. They’re just along for the ride. They can go either way, they’re there. But then the 25% of the people that will be against you. Now, that’s where I get angst and a little bit of heartburn. I’m like, I have got to go figure out-

Perry Holley:    I need a 100%.

Chris Goede:     How to get to 25%, at least to the undecided right in the middle. And here’s what he says, “Instead of trying to gain consensus and, or please everyone I’ve learned to accept this and focus on enlisting the 25% who are with me to influence the 50% who are undecided and to completely ignore” … I was like, I was like free from this, ignore the 25% who are resisting. And I naturally, as a leader, want to go, I got to figure out how to get those 25% on board. And what he’s saying is that’s wasted energy.

You better go after the 50 meaning, have your top 25% that believe helped bring the 50 up because what will naturally happen if you don’t do that is the 25% that are against you. They’re going to try to persuade the 50% to be with them. And you don’t want to grow that bottom number. But at the end of the day, you’re never going to have a 100% consensus. And that’s relieving for me as a people pleaser.

Perry Holley:    And you and me both. It’s funny. And we do, the energy was what I was thinking when you said that it was, oh, how much energy do I expend trying to get the resistors to come be either moderates or believers when I should just be working on the influencers and the influence, the influence … my influencers, they influence the others. And we can get along a lot of progress that way. Well, that’s great stuff, Chris, why don’t you wrap it up for us?

Chris Goede:     Yeah. As I wrap up this lesson that we’re talking about, and you can tell Perry and I are, this is real for us. We’re passionate about it. This one’s a little bit longer than some of the others. Because we live this out. And so there’s lots of stories. As John says, you’ll just be grateful things we didn’t share, but we did share lots of them. But I think you got to ask yourself, here’s a couple of things. You got to ask yourself, this question, do you want or desire to lead more than you want to please or like? This comes directly from our core CEO who John challenges and has mentored for years. John would ask Mark this question, because Mark is a natural bent towards level two as well. And so then in turn, Mark would begin to figure that out and wrestle it.

And he began to ask us. And so that was the first thing that came to my mind. The other thing was I was listening to a podcast from Craig Rochelle, the other day. And he made this statement. And so I went back, found it, and I want to give it to you as well. He said, “Become a leader who people like to follow, not a leader that everyone likes.” And I was like, ooh, yeah, I get it. There’s a big difference between one that is popular and one that is respected as a leader. And I think if you can begin to understand as maybe to go from a pleaser to a challenger, it’s really about respect and that not everybody is going to like you. And I think the other thing too is, as you think about this culture that you’re building in your organization, your team and your leadership, if you are on the side of a people pleaser, what I want you to understand is you have change in your pocket to challenge them.

They’re going to know your heart. They’re going to know your intent. They’re going to trust you. And you need to trust in the fact that you have led them well and connected with them at level two and create enough change in your pocket to have to challenge them when you do that. Because remember, as a leader, you’re getting a paycheck every week, every other week, once a month, whatever it is. And going back to what we talked about, you got to have your organization’s best interest in everything that you’re doing. And I think you have permission to challenge your people because if you’ve led them so well and you had to change in their pocket, they’re going to know where it’s coming from.

Perry Holley:    Relational capital.

Chris Goede:     Relational capital as you say.

Perry Holley:    I love that. Okay, Chris, thank you. Great stuff. If you would want to know more about these five levels or the 360° Leader, get that limiter guide. You can do that at We also love it if you leave us a message, a note or ask for more information, we’re glad to provide that for you. We’re always grateful that you would spend this time with us. That’s all today from the John Maxwell Executive Leadership podcast.

Be the first to comment on "Maxwell Executive Leadership Podcast #127: Making the Relational Shift: From Pleasing to Challenging"

Leave a Reply

Your email address will not be published. Required fields are marked *