CEO Doesn’t See Flaws in His Executive Team? Ask Madeleine

Dear Madeleine,

I am an HR generalist working at a REIT (Real Estate Investment Trust). Our CEO started the company about eight years ago, and I have been his right hand since the beginning. He is a genius in many ways—high IQ, a deep intuitive understanding of the real estate markets, a complete whiz with spreadsheets and how money works. He has a dazzling intellect and charismatic personality.

When I first started working with my CEO, I thought he had a flair for hiring. He spots talent and goes to a lot of trouble to pursue people and persuade them to come and work with us. He now has an executive team that he has hand-picked over time, and he depends on them.

The problem is that he falls in love with these people and can’t see any of their flaws. He refuses to hear anything negative about anyone he’s hired (although he can be ruthless with everyone else).

We have a chief financial officer who started out amazing, but is now wildly inconsistent. She comes in looking like a million bucks, prepared, and brilliant one day, and disheveled and semi-coherent the next. I suspect a serious substance abuse problem or possibly a mental health issue. Our industry is highly regulated and having our books in order is critical. I believe our CFO’s erratic behavior is going to cause some real headaches in the future.

Our chief revenue officer clearly has something shady going on. He disappears for days at a time and his direct reports must either wait for him to show up to make pricing decisions or make decisions on their own. They are often frustrated because they are held accountable for closing deals, and, in many cases, they can’t move forward without him. This is now impacting our numbers—and when troubleshooting conversations happen, the fact that our CRO is AWOL most of the time never seems to come up. His direct reports come to me to ask if I know where he is, and I never do. I swear he has another full-time job.

Our head of IT has multiple personalities. He is amazing at what he does, but all of his people are terrified of him. I am also afraid of him. You never know who you are going to get—sometimes he is perfectly normal and other times he is downright mean. It is only a matter of time before someone files a hostile work environment claim.

There’s more, but you get the idea.

I have tried to raise these issues with the CEO. I have shared my observations in writing and set meetings with him to brainstorm how to approach these problems. He is now skipping our regular one-on-one people review meetings, not opening my emails, and essentially ignoring me.

I truly care about my boss. We built this company together and he has always trusted my input. I know he doesn’t want to hear what I am saying, but I am afraid at this point that he actually may be risking everything he has worked so hard to build.

How can I get through to him? I feel like a train is coming at us and he refuses to get off the tracks.

My warnings are falling on—

Deaf Ears


Dear Deaf Ears,

Well, this sure sounds frustrating. The Curse of Cassandra, familiar to anyone who is paying attention, describes the frustration experienced by someone seeing disaster ahead and not being able to influence those who need to heed the warning to listen.

I think many are also familiar with the personality profile of your CEO. I have worked with many executives like this.

At the risk of offending you, I am hearing that you have a fantasy that you should simply be able to walk into your CEO’s office and dump all these problems on his desk for him to deal with. Part of what is happening is that he doesn’t want to see what is in front of his nose because he already has too much going on. I suspect he also doesn’t want to face the unpleasantness of having to hold people accountable—especially if he is still operating under his initial impression of them, which no doubt didn’t include the reality that everyone, no matter how great, has flaws and frailties.

You have been with your guy from the beginning, and yet you call yourself an HR generalist. I wonder why you aren’t CHRO? Are you not a member of the executive team? If you’ve been there since the beginning, do you not have equity in the business? If not, why not? You didn’t ask me about this, but it might be part of the problem. If you haven’t earned the CEO’s respect after all the work you have done together, it might explain why he is ghosting you at this point.

I’m really not trying to make you feel bad, just trying to get to what is really going on here. If what I’m saying resonates with you, and you can spot the pattern of letting your CEO overlook your contribution, it may be time to cut your losses and find a new environment where your experience and smarts are appreciated and properly rewarded.

If I am way off on this, please forgive me, and let’s try another angle.

I wish I had a dollar for every time I’ve heard a senior executive say “Don’t bring me problems without some ideas for solutions.” I would be able to pay for a two-week vacation in the Caribbean. This leads me to suggest that you send your boss an email with the subject line: Some Problems I See and What I Think We Should Do About Them. Volunteer to do most of what you think needs to be done; e.g., the hard conversations that go something like “This is what I am seeing; what is going on here?” And if he doesn’t respond to that, it may be time to decide that someone must be an adult—and tackle the bad behavior yourself.

The question is: how much power do you have? If key employees are having problems, especially problems that are going to impact the organization, aren’t they in your wheelhouse? Are you not taking responsibility for what is going on because these people don’t technically report to you?

  • If the CFO is acting strange, what is getting in the way of your sitting down with her and pointing out what you see and how it concerns you? Wouldn’t you say something if you smelled alcohol on an employee?
  • If the CRO is AWOL and his people are coming to you, what keeps you from calling him and saying, “Where on earth are you and what the heck is going on?”
  • If your CIO is awful, especially to you, where are your boundaries? As the head of HR and the employee with the longest tenure, it seems perfectly reasonable to me that you would say “You are acting kind of scary, and I request that you cut it out—and, for that matter, that you do not behave this way with anyone else in the company.”

Are you afraid these people will all go running to the CEO to have him provide cover? If that’s the case, it is time for you to leave him at the mercy of the train.

It sounds like you have given up all of your power. This has probably happened slowly over time. You have had your common sense and authority overridden for so long, you have gotten used it.

Oh. Oops. We’re back here again.

This is not the answer you wanted. I’m sorry. But somehow you have lost your power to influence your CEO. Either you have lost his respect (and because he is obviously loathe to confront anyone, he has not shared that with you), or perhaps he is waiting to see what you will do. Maybe he thinks it is your job to confront these people.

If your CEO won’t give you the time of day, you have to confront that. If you make yourself impossible to avoid, you will probably get a straight answer. Then at least you’ll know.

You have some big decisions to make. They aren’t fun or easy ones. But at least you are smart enough to get off the train tracks yourself. So, if all of your efforts fail, please do that.

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.

Got a question for Madeleine? Email Madeleine and look for your response soon. Please be advised that although she will do her best, Madeleine cannot respond to each letter personally. Letters will be edited for clarity and length.

About the Author

Madeleine Homan Blanchard

Madeleine Homan Blanchard is a Master Certified Coach and cofounder of Blanchard Coaching Services. She is coauthor of Blanchard’s Coaching Essentials training program, and several books including Leverage Your Best, Ditch the Rest, Coaching in Organizations, and Coaching for Leadership.

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