Potential CEO Lacks Humility? Ask Madeleine

Dear Madeleine,

I am the founder and CEO of a specialty investment services company, which I started—for fun—after retiring from my first career in investment banking. My executive team is amazing. Since we are so specialized and the field is super technical, I have had to find the best and the brightest.

My problem is that I am ready to retire—for real—sometime soon. The guy who is slated to succeed me is a genius but, unfortunately, a jerk. He is perfectly capable of not being a jerk: he is downright warm and charming with clients, but he is horrible to the people he works with. He is extremely smart, has never failed at anything, and has no humility.

I trust him implicitly when it comes to strategy, advising clients, and making decisions. But I am afraid if he becomes CEO, people will quit in droves and the whole company will fold.

I don’t want to see all my hard work go down the drain. How do I approach this with him?

Ready to Go

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Dear Ready to Go,

Head on, my friend! That is the only way. Tell the truth, lay out the crossroads choice that Junior has before him, make some demands, and hold the line.

Is there no one else you can trust to take your place? That is my first question. If the answer is an unequivocal no, you are going to have to bite the bullet and demand to see some change—and soon. And there must be consequences for your successor if you don’t see the changes you need to see.

I do think many people who end up in the investment banking industry are accustomed to having bosses who are whip smart but not very—shall we say—nice. This is based on my own experience working in the field and the many anecdotes I have heard over the decades. It is universally acknowledged that investment banking is a little like trench warfare.

Given that, I wonder what worries you so much about Junior taking over. What does he do, exactly, that you think will cause people to quit in droves? I suspect you have plenty of examples. Use them. You must be specific if you are going to give him feedback and demand change—and even more specific about the exact changes you need to see, so that you can track and measure the changes. You will want to come up with a list of do’s, don’ts, and non-negotiable never ever agains.

The good news is you know he knows how to act like a decent human being because you have seen him do it with clients. He just needs to figure out how to keep it up with his peers and employees.

If you have any stated company values, you might be able to use those to point to the ways Junior is not a role model for them. You could also give examples of his good behaviors with clients that are aligned with the company values that he might use to replace some of his not-so-nice behaviors with colleagues.

Another thought is to share this article with him: Level Five Leadership: The Triumph of Humility and Fierce Resolve. It is based on Jim Collins’ research about the leaders of companies who stand the test of time. An oldie but goodie, it outlines the long-term advantages of humility as an unbeatable leadership trait.

You might also share something Ken Blanchard has often said about humility: “Humility isn’t thinking less of yourself, it is thinking of yourself less.” People can learn to be more humane, kind and considerate to others. It isn’t easy and it takes practice, but it is doable.

Will this be the first time Junior has heard feedback about what a jerk he is to the people he works with? It may come as a surprise to him. But if he is as smart as you think he is, hopefully he will see the value of making an effort. If you give the feedback and ask for clear concrete evidence that he can change his ways, and you are met with a blank stare or a straight-up unwillingness to even try, you may want to consider closing down the business or selling it to a competitor that has a decent leader who knows how to treat people. I think if Junior knows you are seriously considering both options, he might be motivated to head off those possibilities.

Humility is a tricky character trait to develop. If a person doesn’t come wired with humility, it is usually acquired through facing excruciating life circumstances such as catastrophic failure of some kind. So Junior is going to have to either fail as a leader, or be imaginative enough to see the dire consequences of possible failure. You, in your quest to help him, will need fierce resolve. Don’t take the path of least resistance if you want to retire with no worries.

You obviously think there is some hope for Junior, or you wouldn’t have written. The question is: will you be persuasive enough to get him to rise to the challenge? Leverage everything you know about him, what is interesting to him, and how much he enjoys winning to get him to see the benefits. Your restful retirement depends on it.

Good luck with your last leadership test.

Love, Madeleine

About Madeleine

Madeleine Homan Blanchard is a master certified coach, author, speaker, and cofounder of Blanchard Coaching Services. Madeleine’s Advice for the Well Intentioned Manager is a regular Saturday feature for a very select group: well intentioned managers. Leadership is hard—and the more you care, the harder it gets. Join us here each week for insight, resources, and conversation.

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