The B2B Podcast Index
Maxwell Leadership Executive Podcast

#402: Questions I Ask Myself to Become a Leader People Remember

Maxwell Leadership Executive Podcast · 2026-06-25 · 24 min

Substance score

25 / 100

Five dimensions, 20 points each

Insight Density5 / 20
Originality4 / 20
Guest Caliber6 / 20
Specificity & Evidence4 / 20
Conversational Craft6 / 20

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

5 / 20

The episode is a list of eight generic self-reflection questions about leadership legacy, padded with platitudes and repetition; almost nothing here would surprise a smart operator.

First question of these 8 questions that I wanted to present was, do the people, um, grow under your leadership?
do I create clarity or confusion?

Originality

4 / 20

Entirely built on Maxwell's recycled 5 Levels of Leadership and well-worn transformational-vs-transactional tropes, with no contrarian or first-principles thinking.

we built everything off of the 5 Levels of Leadership
would people describe you as transformational or transactional?

Guest Caliber

6 / 20

No external guests; two in-house Maxwell facilitators/coaches speak in general terms about having run P&Ls but offer no demonstration of operating at scale.

Perry and I both have run P&Ls before and run organizations
I'm Perry Holley, a Maxwell Leadership facilitator and coach

Specificity & Evidence

4 / 20

Almost no named companies, metrics, or dollar figures; the few anecdotes (son in trouble, a delayed deal, IBM culture) are vague and lack concrete data.

my son got in a little trouble and I was the last to know
I get told that a deal's not gonna happen

Conversational Craft

6 / 20

Friendly co-host banter with mutual agreement and self-praise rather than probing questions or pushback; questions are mostly setups for the next platitude.

I love this question because you could have people perform and trained
I agree with that 100%

Conversation analysis

Computed from the transcript - who did the talking, and the verbal tics along the way.

Filler words

so38right18like15kind of5uh4actually4you know3um2I mean1basically1

Episode notes

Get the learning guide from today's episode here! In this episode, Chris Goede and Perry Holley explore eight key questions leaders should ask themselves to build a memorable leadership legacy. They discuss how true leadership involves developing others, creating clarity, and fostering an environment where team members feel safe to share the truth. They also examine the importance of building future leaders, being transformational rather than transactional, and ensuring every interaction leaves people stronger. Throughout the conversation, they share practical strategies and thought-provoking examples to help leaders reflect on their influence and grow into leaders who leave a lasting, positive impact.

Full transcript

24 min

Transcribed and scored by The B2B Podcast Index.

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. And I'm Chris Goede, Executive Vice President with Maxwell Leadership. Welcome and thank you for joining I want to remind you to go to maxwellleadership.com/executivepodcast. There we got a button for you. If your team is looking for some leadership coaching, training, consulting, man, we'd love for you to fill out that form and we'll follow back up with you. Well, today's topic is one that— I'm going to set it up with— this is a question that we often will ask at times when we go into a room, and it's phrased a little bit differently, but I love it. Questions I ask myself to become a leader that people remember. Now, oftentimes we will ask people a question, who's the greatest leader you've ever worked with, you've served for? Maybe it was in your family, because we want them thinking about the attributes of these, this, the greatest leader, right? And when you think about those attributes, man, as a leader, I know that I go, I start internalizing that going, am I that leader? Am I representing that to my team? Because that's my leadership. That's going to be my leadership legacy. And I love this word legacy. And oftentimes people think, hey, legacy is what you leave for people. And I want to encourage you to think about it a little bit different. It's what you leave in people that is really your legacy that is going to live beyond. And so for us, when we built everything off of the 5 Levels of Leadership, This is where a leader has done levels 2, 3, and 4 for so long that they now— people look at them as a level 5 leader. And what we mean by that is level 1 influence is you have a title, so you're leading people and people are following you because they have to. Level 2 is that people are following you because they want to. That's where you've connected with them, built relationships with them. Level 3 is you guys have produced together, you've won together, and you have influence with them because of that. Level 4 is when you begin to develop other leaders, you begin to pour into them personally and professionally. And when you have done that for so long and so well, then people look at you at level 5. Matter of fact, I think if you right now go back to the question, who's the greatest leader? And you think about that person, you can actually see that lived out. So I love this. We're going to talk about what does this look like and the questions you should be asking yourself so that you can get there. Definitely a level 5 lesson. We don't do many of those. No. Something that you cannot call yourself. You can't earn it. Somebody has to award it to you. Level 1's awarded to you by an organization, probably. Level 5 is awarded to you by the people. And not everybody's going to be a Level 5, but you can aspire to it. And that's what I want to encourage you about today with some of these questions. And one thing I think that maybe everyone listening right now, think about a leader that really made an impact on you, somebody that you do remember. Maybe I should have put remember for a good reason. I remember a couple for bad reasons. Yeah, that's right. Well, there's probably many of those. Our leadership, those that are listening, may be watching, uh, you're, you're molded by that. Yeah, right, right. And, and either you shy away from it, or maybe you even have some tendencies to it, and it was a negative side impact for you. So think about the, the leaders in your life that you remember. I've— of all the leaders I've had in the many years I've been doing this, I'll probably have a handful, less than 5, that really stand out to me. And I've been thinking about what did they do to do that. First question of these 8 questions that I wanted to present was, do the people, um, grow under your leadership? Are people growing? This is probably one of the most important leadership questions, and it really speaks to Level 4. If you've done Level— what maybe we should say that Level 2 is relationship, Level 3 results, and Level 4 is reproducing leadership. So it's really growing others to do that. But asking the question, do they really grow into your leadership? Yeah, this is a great— I love this question because you could have people perform and trained, but I think what you're getting at under grow under my leadership, are they developed as a leader? And do you think about that? And so we're in the organizational development business. And so we know as an organization, Perry and I both have run P&Ls before and run organizations, and we know we can measure that. We can measure the results of the organization, but oftentimes it's hard to really measure how many people you've developed.? Or how many people on your team are you developing them? And so here's some things to be thinking about under this that you can be asking yourself. Are people becoming more confident around me? Are they more capable? Are they better decision makers, better communicators? One of the things that— are they better thinkers? We often talk about, hey, are you helping your team think differently, think better? And If your people, if you have team members that have worked for you for a little while and they depart and you don't see a big difference in them as a person or development, then you've really just managed them over those years that they've been with you. You have not led them. You have not helped increase your influence, by the way, but it's really through true leadership. Do you think there's a difference in developing them as leaders versus developing them outside of a leadership capacity. I mean, we always talk about are you developing the next generation of leaders, but not everybody wants that. Not everybody wants to be, but we believe everybody's a leader based on influence that they have. So I'm just thinking is certain people I think are going to be in the leadership pipeline here. I'm going to do a little more hands-on with that, but everybody needs to be developed, an IDP type of a development plan. I agree with that 100%. By the way, The research is showing that people, to differentiate yourself in the, what I would call even turnover or hiring process, is they want an IDP. They want an intentional development plan for them in the interview process. They wanna know that you're thinking about them. I love this question though, cuz you go, hey, I'm leading 12 people, which is, by the way, too many direct reports. That's another podcast that we'll do. But you got that and then they got teams and there's a couple thousand people, whatever, whatever the dynamic looks like. There's a difference between adding value to people so they develop versus intentionally developing people. I think everybody on your team, you should add value to so that they develop. But I think there are certain ones on the team that there's an intentional development process by the leader back into them. And I think that's the diff— all of them need to be trained, okay? Because that's the IQ side of it., but I think there's a little bit of difference there between the two. Yeah, good. That's what I was thinking. Yeah. Question number 2 that I would ask if I want to be a leader that people remember is, do I create clarity or confusion? And this one can be a little tough because some organizational problems can actually lead to clarity problems that go on. But I think about the greatest leaders in my life, that they were very clear. Their expectations were not vague. They were clear on what they expected me to do. Their communication was very consistent. I think if you're not going to be remembered, you have inconsistencies in how you speak and communicate. Priorities didn't shift from these leaders that I had, and the decisions they made, they felt certain, whether they're right or wrong, but they were certain. There was no uncertainty or inconsistency in their decisions. Yeah, I think one of the greatest things a leader can do is communicate in a way that is simple, that is able to be understood by the masses. And so I think they help people when you do that, understand, you know, what matters most, what does success look like, what are the priorities, why those decisions actually matter that you're having to make. People can handle organizations that go through difficult times, right? But they can't handle when there's not certainty or when there's not clarity in the certain situations. Because all of us are going to go through hard times in our leadership organizationally, personally, professionally. But man, really work hard on trying to simplify the message as much as you possibly can. Good. Number 3. Number 3. Do people feel safe telling me the truth? This is back to that psychological capital. And this is interesting. You may feel like they feel safe, but I think insecure leaders, I would say that they actually feel like everyone is comfortable telling them the truth, but that's really not the case. And I think one of the things that you can do in that is making sure that you are asking good questions to get them to that. I was just having a conversation yesterday, and I'll share the story because I think it's relevant to this. And I tend to lead, and I like to have fun and sometimes have high energy. And when I'm facilitating, sometimes I go, hey, I got two languages, right? I got English and sarcasm because I like the good. Well, one of my team members, brought this up to me. And it's the first time that we've had this conversation about when I lead with that sarcasm, she wasn't at a place where she felt comfortable telling me the truth, that she then doubts what she's doing because I'm leading with sarcasm. And so, man, we broke down a lot of different walls because not only should I not be leading with sarcasm, that's another podcast, but also what I discovered was she wasn't safe telling me how she truly felt until yesterday in our meeting. And so I wanted to unpack that as well to figure out why was that? What was the underlying pin of why she didn't feel that way? So sometimes leaders, man, put your pride and ego aside and ask some tough questions to see if they really feel safe telling you the truth. Well, this one was very real to me because this was many, many years ago, but the way I first discovered this was my son got in a little trouble and I was the last to know. And when it all got settled and working out, I went to him and said, "Why would you not come to me? Maybe I could help." Yeah, on the front end. The question then transferred into a work situation. We're toward the end of the quarter and I was a sales executive. And at the last minute, I get told that a deal's not gonna happen. I said, "How long have you known this?" He said, "Well, you know, 5 weeks or so ago." "Why would you not tell me?" And then you start, the question you need to be asking yourself, do people tell you hard things? Do people bring you bad news? Do people tell you difficult things? If they're not, They just disagree respectfully, or they only surface problems late. They don't come to you. They don't trust you. The word I'm thinking, what really changed me was the word consistency. Consistency in how I speak, the words I use, the emotions I use in my actions, that I'm predictable. And that if you know you can bring Perry bad news and he can handle it, he's not gonna shame you, yell at you, cuss you. He's not. There will be consequences for sure. Sure. However, it's okay to bring Perry tough stuff. And I have to say, for a long time that was not true. And let me tell you, senior leader, your title enters the room way before you do. And even though you, and this may be a little bit in your situation, you would never once in your life, I could not even fathom you playing your title. I don't think you think about your title. It's not even a thought in your head. However, everybody around here knows that you're the executive vice president of this and that. They just act differently. They do. But by your consistency and how you treat them, you tend to teach them that it is psychologically safe here. What you say matters. And you can tell me hard things. I'm not gonna punish you for it to do that. And so I remember leaders who, they didn't avoid the hard conversation. They allowed me to enter into it as well as they did too. Yeah, yeah, that's good. Number 4, do I protect my team or do I protect myself? This question will reveal a lot about your character as a leader. And generally it happens when pressure rises, when things are a little terse and things getting hard and the pressure's on in the business. Do you think kind of lean towards self-preservation or toward your leadership responsibility? Isn't that oftentimes you hear the leaders when it's going well, it's like, yeah, I, and when things go bad, well, the team, right? No. Yeah, this is, for me, this is a big deal. And I think some of the most memorable leaders that I've had that modeled this for me took responsibility publicly when really it wasn't even their fault. It was my fault on their team. And they never addressed it with me publicly. It was always conversations that we had privately. And he always advocated for the team. And so to this day, when I think about great leaders, it's a leader like that that stood next to Me stood next to our team during times like that, took the weight, took the responsibility, and it was all about that leader taking the responsibility versus that leader propping himself up in any way or deflecting that. And I think that that is an attribute of a leader that you need to make sure that you're living that out. Number 5 question for yourself is, am I building future leaders? This is all level 4 right here, conversation and language for us. This is the difference between someone that is basically taking people and getting the job done through the people versus taking the people, getting the job done, but then also developing them. And hopefully you could even step out. What's the phrase you talk about often where leaders say, man, I hope it exists without me better than it is? I want you to speak to that. But that's where we're going is if leaders, you had to step away, you weren't Able, something came up with your family and you were out for an entire week. What happens to the team? Who's stepping up? Where are the leaders? And if you go, man, I don't know, it would be a complete mess. Well, we have some work to do around this question. Well, I had a guy that was— the whole idea was, are you the kind of leader that wants to see things work without you? Yeah. Or the kind of leader that wants to see things work, you need to see it work because of you? And I had that leader. Yeah, I had that leader tell me, uh, I was out on vacation and the place fell apart while I was gone. Well, is that okay? He goes, well, they really need me here. What? Okay, so what if this whole idea about, I think about the leaders that really stood out in my mind, they were very intentional about developing a team that worked well without them. And I came up in the IBM culture and it was not that unusual for an executive to be asked to step away to go handle a special project or a special problem or to go to another city for 3 months to start up a new venture. Your team has left and have you done the work? So, well, I think what do they do? How do you become this leader that sees things work well without you is that you delegate meaningful responsibility. You challenge people to handle things while you're there to see if they can handle things while you're there. But when you're not, you kind of teach and mentor decision-making, which means that you need to not make all the decisions. You need to make them make the decisions and then coach them in their thinking about that. And again, coaching instead of controlling is that instead of getting you to do what I want you to do, can I coach you into choosing the right things to do? Helping me setting the priorities, what if I coached you into you setting the priorities to do that? Giving them room to lead, stepping back, and you can watch from a distance. But we just did a podcast a few weeks ago on failure and about John's new book on how to get a return on failure. And so sometimes stepping back and letting them fail is the greatest teaching that we can do. Yeah. And allowing them to get the experiences they need to be able to lead in the future. I just think so many times in my early years I stepped in, I just wanted— and I did it from a really good place, and most of you are doing it from a really good heart. I want to help them, I want to see them succeed, but they're, they're lost when you leave. When you leave, they can't, they can't do anything. So yeah, you have challenged me in that area quite a bit because I do see it as a positive, right? Well, they don't need anything else on their plate. Well, let me go ahead and do it. Well, and what I realized was that then when there were times that I had to step away from the business because I quote unquote wanted to be the good leader and take that responsibility versus developing and equipping them to do that, then when I wasn't there, it didn't get done. And so I love that little piece that you put in there. Number 6, the 6th question, do people leave interactions with me Stronger or smaller? I love this statement of when you walk into a room, do people leave the room and go, well, man, that individual was the smartest person in the room? Or do they leave the room and they go, they feel a little bit smarter because they were in the room. And so this is huge. This is where I think every interaction that you have with a team member can add confidence to them, not remove it. This is also where you can challenge people in a way, but yet do it the right way and not lose influence. We talk a lot about, as you move up the levels of influence, how do you produce and have feedback and have really good conversations without decreasing your influence? This is a way to go about doing that, is having those types of conversations where people leave feeling stronger, more confident, even though they may have received some tough feedback. So you're correcting without humiliating them, you're coaching them without belittling them, and you're pushing them without completely crushing them. You're always making people feel something. Are you aware of what you're making people feel? And could you make them feel something on purpose and say, I don't want anyone to leave my presence feeling small or insignificant or that they are not enough? I'll speak personally, was I struggled a lot of times in early years of thinking that I didn't have what it takes. Why? Like imposter syndrome. Why am I here? And then to have a leader that makes you double down on that, yeah, you don't have it. I want you to leave my presence knowing that you have what it takes and I'm here to help you. That's all there is to it. Question 7, would people describe you as transformational or transactional? Those leaders that I remember were transformational. Transactional leaders focus mainly on the task of doing the work, the metrics, the compliance, the output, the results, all important, but the transformational leaders, still care about, while they still care about results, they also develop people along the way. So I think we talk so much, this is why these 5 levels of leadership is such a strong model for you to embrace, is that I need to have that level 2 relationship with you, but I'm going to have to ask you to work hard at level 3 for results. And I can't forget level 2, the relationship, while we're doing the hard part of results at level 3. And I think a lot of leaders kind of, forget this, they move on to level 3. And I think about the law of connection that you have to touch a heart before you ask for a hand is that we continue to ask for the hand, ask for the hand, you're not touching the heart, which is level 2 stuff. So this idea of can I be more transformational by transforming you in the work of doing this work and not just the work itself. I think transactional leaders, all the work that we've done in research and organizations, I think you would agree with this, transactional leaders often will see higher turnover inside their organizations because we have to produce, we have to get things done. But if you go about it and it's just about the assignment and you're not changing the way that they think, the way that they lead, the way that they will believe in themselves, because you have to lend that to them, right? You have to lend that stuff as a leader. That's when that transformation happens. Well, the 8th question is, if I left tomorrow, What would people remember most about being led by me? That's a good homework question. That is a great homework question because every leader's gonna leave, by the way. Like I know most of you and maybe even us sitting here today in the studio go, well, if I left Maxwell Leadership, this place wouldn't exist, or I'm never leaving Maxwell Leadership. Okay, that's unrealistic, right? Because every leader's gonna leave. And so The leader is going to leave that you're currently working for. They're going to get promoted to a different department. They're going to get another opportunity that's best for their family. What's the imprint, right, that that leader left on you? What's the imprint that you are leaving on other people on your team? Because that's what stays for years. That's the difference. And that's why it's a Level 5 lesson is you need to decide this today and then work toward it every day. You can make the decision and then manage it every day. Will they feel that they felt with you, they felt fear with you, they felt micromanaged, or they felt the power of your ego or all your inconsistencies? Or will they say they felt growth and trust and encouraged? I felt like I had courage when I was around you. I felt like there was opportunity. I felt integrity. Are those— you make the decision and then behave accordingly. Well, as we wrap up, here's the deal. This is not something that just happens overnight. This is something that takes time. It, uh, has to have a lot of consistency behind it. And let me say this, it's gotta have a lot of authenticity behind it. And every person that you influence, which we all influence people, they need to be influenced differently. And so you need to find and navigate that way, um, to be able to influence them and add value to them as you think about even some of these questions that we, uh, posed to you today. Remember your leadership imprint, your legacy. It's what you leave in them, right? So it's not about the results. It's not about the transactional piece. It's about the lives that you've changed along the way. So as we leave you, I'm gonna add one other bonus question. We've already talked about who's the greatest leader you've ever had the privilege to serve under, serve with, serve for in your family. And then the sub-question to that is, Are you living out those attributes in your leadership to other people? So hopefully those 8 questions, take them, write them down, ask your team about them, and be transparent in order to become transformational and not stay transactional. Fantastic. Well, thank you, Chris. As a reminder, if you'd like the learner's guide to have those 8 questions there for you, you can get that as well as learn about our other offerings or other podcasts in our podcast family. You can do all that at maxwellleadership.com. Maxwellleadership.com/executivepodcast. You can also leave a question or a comment for us there. We love hearing from you. Very grateful you spend this time with us today. That's all from the Maxwell Leadership Executive Podcast.

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