I had lunch the other day with a friend of mine who is in charge of managing a very famous, very iconic brand. The brand needs some shaking up, and he got the call. He’s very good at what he does, and so far, so good with the changes.
Great.
But then, as he was talking, he alluded to some resistance he was running into with new initiatives, and how he was on his own journey of discovery trying to figure out where “the system” was worthy of his accommodation, and where he should blow through it.
To get a sense of what he might be talking about, I tried imagining him—sitting there in his t-shirt and jeans—ruling a roost his predecessor had filled with suits. What issues was he facing? I asked myself.
Even over a sushi lunch, it wasn’t difficult picturing him in charge. But then, it wasn’t difficult picturing some of his staff responding to his brash style with inaction, either.
But why the resistance? Why wouldn’t they admit, “His willingness to break convention to achieve results intimidates me into inaction,” and then move on? Probably, I realized, for the same reason Rip van Winkle wouldn’t go run a marathon immediately upon awaking after his 20 year snooze.
Alright, so what would the staff do if not follow him? This one was easy: I could almost hear them whispering to coworkers, crying to HR, or complaining to managers, “He’s so arrogant!” In response, I could imagine one of two responses, depending on the person: “You’re right,” or, “Oh, I think he’s great—we need a leader to breathe new life into this place!”
That’s when I realized that my friend had two problems: first, adjusting his style to help people stretch and get ready to start moving, and second, correctly interpreting the critical feedback he was bound to get. The way in which people were likely going to communicate their concerns would be to project their own fears and inadequacies. Rather than say, “I’m afraid if I invent a new process for this, I might get it wrong,” they’d blame him for breaking the old process. “It’s your fault my back aches… I was doing just fine before you woke me up!” That sort of thing. Not helpful. He would then likely get advice from peers, bosses, and coaches that would sound like this:
“To win people over, embrace excellence, not arrogance.”
That’s when I realized why he had made the comment to me about running into resistance: the advice he was probably getting about how to fix this resistance issue—whether it came from subordinates, peers, coaches, bosses, or even other business coaches—if it sounded like what I thought it might sound like—was inactionable. He was looking for a second opinion.
Because when you get right down to it, when you’ve got someone who is good at his job, who knows it, who is willing to use power to move things along, who is not tolerant of convention born from thoughtless routine, and who pushes others to break the mold, that person will be interpreted as both arrogant and excellent… and everyone in the place knows as much one day one. So telling him to monitor the arrogance would only serve to remind him that some people are resentful about his changes. Which he obviously already knows.
So we need to move beyond the question, “Is my friend arrogant or excellent?” This was our starting point. The correct answer is, “Stop wasting my time. The answer is both, we already know that, let’s go.”
The question that counts is, “Does his style inspire followership in the current setting?”
A great contributor—arrogant, excellent, humble, or otherwise—in a position of authority races too far out in front of the pack and leaves everyone else behind. We call these people know-it-alls and we don’t like them. We isolate the humble ones, tolerate the excellent ones, and make life difficult for the arrogant ones. But under no circumstances do we willingly embrace this person as a leader unless they are thrust unwillingly upon us.
An administrator in a position of authority—someone who enjoys bossing people around but lacks a sense of vision beyond his or her own gratification, fails to generate followership because he rubs people the wrong way. We call this person an a-hole and do everything we can to make his life difficult.
One who inspires followership alters his approach enough to engage others in new thinking. You can be excellent and do this. You can also be arrogant and do this. At the heart the ability to inspire followership is an ability to make others feel capable of rising beyond themselves… this ability is not always related to how you think about yourself.
All this thinking was happening quickly, in the space of just a few bites of edamame. As I mixed wasabi into my soy sauce, in my mind I started taking the idea to the extreme: could I think of someone so outrageously arrogant that the negatives of the arrogance eclipsed the person’s excellence? Someone who lost followers strictly through arrogance? I needed a foundation for any advice I might decide to give my friend!
Being in Chicago, six names immediately came to mind as test cases:
- Oprah. A woman so powerful the city closed down Michigan Avenue to throw her an anniversary party.
- Mayer Daley. Hizzoner.
- President Obama. Ambitious first term senator stops Inevitability to become president.
- Hugh Hefner. (This may be a surprise to you, but Playboy’s editorial headquarters are here in the city, just a few blocks from where I was having lunch, and as we were talking iconic brands, it fit in the moment.) Hef’s a man with such a healthy ego that his personal brand has lasted half a century.
- Michael Jordan. Was just inducted into the Hall of Fame. During the ceremony, he quipped there’s no “I” in “team,” but “There is an “I” in “win.”
- Trump. (They just finished building his namesake tower here.) He redefined “brazen” for a whole new generation… twice.
The conclusion of my down-and-dirty analysis was this: being a pompous, know-it-all jerk will indeed bite you in the butt. BUT (and it’s a big but) sometimes, especially in times of change, there is no line between excellence and arrogance. To be successful, you may just have to risk going there.
Here’s the analysis:
- Oprah. Oprah unquestioningly inspires many people to do much good. The way she does it sometimes may appear just a little bit self-serving. Now, I think most will see the good deeds and think, “excellence.” Some might see her name plastered everywhere and think, “arrogance.” Me? I see a woman who is constantly leveraging previous accomplishments to achieve new, bigger ones… and who at times is very likely trapped by her celebrity, by her sex, and by the color of her skin. (Does anyone else forget that she’s black?) So, excellence or arrogance? Who the hell knows—and who the hell cares. Oprah is a one-woman lead car in a very long, very powerful, very overdue parade. With that kind of responsibility on your shoulders, you become what you need to be to ensure success, and you do as much self-congratulating as is necessary to keep the airtime filled with positive messages. Because if you ever relent, the naysayers will be there in a heartbeat to tear you down, and then it’s not just you who fails, but everyone else who put their cars in your parade.
- Mayor Daley. If Daley has a problem, it’s forgetting to disassociate the names “Daley” and “Chicago” sometimes. But that’s not arrogance, that’s entitlement, and that’s not the subject of this analysis.
- President Obama. Frankly, he’d better be arrogant… and he’d better be good enough to back it up. He’s the president of a nation of 300 million people and the leader of the free world; when he speaks for the people, he’d better (1) damn well believe that he deserves the right to speak on our behalf, and (2) have something well-reasoned and intelligent to say.
- Hef. The man has been successfully challenging established cultural norms about sex that, after half a century, still bite back. Now, personally, I think humanity has had an undeclared war on sex going on since about the Middle Ages, and that America’s cultural norms on the subject—an uptight mash-up of hypocritical Victorianism and sophomoric titillation—are laughable. But my personal opinions aside, it’s hard to see how others’ opinions of the man wouldn’t range clear across the spectrum, from excellent to arrogant to scoundrel to bastard. Equally unclear is whether he could have led a successful assault on outmoded mores by confining himself to a more limited position in that spectrum, as Dr. Ruth, Larry Flint, and others have done.
- Donald Trump. Trump has turned his arrogance into the foundation for his celebrity, and has turned his celebrity into a cash register. I’m personally not a fan. I think his brand of celebrity erodes society rather than builds it up. But at the end of the day, his arrogance and the noise it creates don’t mean squat. When he gets sued, it’s because he stuck it someone financially. So there you go.
In the end, I told my buddy nothing about any of this. I think what I might have said was something along the lines of, “It’s got to be frustrating, getting the resistance, knowing that some of it’s worthwhile and some of it’s bullpuckey. Just remember to move at a pace the organization can follow.” Then I think I pointed at the last gyoza as a sign he should take it. If he’s reading this, I’d want him to do three things:
- You do have an issue when it comes to resistance. Take that seriously.
- You will get tagged as being arrogant, and sometimes, people will be right.
- Take an interest in people and go out of your way to help them. Don’t just set the example; ask questions, circle back and see how they’re doing, get them help as needed. Do this, and you can be arrogant until the end of time and no one will care, because your demonstrated interest in others will help them rise above themselves. These activities are the leadership equivalents of helping Rip van Winkle stretch and train for that marathon—they might hate you for it, but they’ll also always appreciate that it was you who got them across the finish line.
Enjoy this blog? Listen to my new podcast, Beyond Social. |

I'm Jason. I make people shine. My mission is to help 1 million people tell their stories better. 
{ 1 trackback }
{ 1 comment… read it below or add one }
Hello again Jason. I really love this article, and can really identify with some of the stuff it brings up. There have been times in my career I’ve felt that I had to choose between being liked and being seen as competent, and I believe it’s more important to be competent. I work in Student Affairs at Penn State and there is definitely a feeling in our work culture that it’s not nice somehow to toot your own horn too much. It’s okay to be good, as long as you don’t act like you know it. That, too, is BS. Do you know the difference between being called a genius and being called an arrogant bastard? If you really know your stuff, but are humble, people call you a genius. If it’s clear that you are aware of how good you are, then people will call you an arrogant bastard. I’ve decided to not dwell too much in my life and career on what other people think of me, but to also act in ways that always focus on making things better for my organization and my people. As long as that comes through, then I believe people will respect me and even some who initially think I am arrogant will soften their views a little bit, by at least saying things like “he’s a little arrogant, but he’s good at what he does, and he means well.” It’s a middle ground I’m happy with.
Thanks again for another engaging piece.