27 September 2023

Good counsel: How to keep your CEO on the right track

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Dawn Burke* explains how to counsel a powerful boss who is making questionable choices.

Photo: Felix Mittermeier

CEOs are only human. They have a tough job with high stress.

Naturally, there are going to be times where their judgement will lapse, even to the point where they may do “terrible” things.

But how do you, HR pro, manage that?

A few days ago, I read a fascinating article in Vanity Fair called “‘I’m a Terrible Person’: Behind The Epic Meltdown That Ended Travis Kalanick”.

It was a behind-the-scenes look at the week leading up to the ultimate demise of famed ex-Uber CEO, Travis Kalanick.

In particular, it shared his inner circle’s point of view on what happened, how they tried to help, and how the team handled Kalanick’s on-his-knees statement, “I am a Terrible Person”.

For those who don’t know, Kalanick, the visionary behind Uber, doggedly changed the face of personal transportation, ultimately breaking up the monopoly that was the taxi industry.

Unfortunately, his widely publicised “bad-boy” antics led Uber, for lack of a better term, “astray”.

To Uber’s credit, they did dismiss Kalanick (they really had no choice), relentlessly focused on correcting any toxicity, and for the most part, they are back on track. Bravo.

This article fascinated me because it shared how the lieutenants around him handled an untenable situation.

Even though most of us have never dealt with such a high-profile CEO or company, many of us can relate to having to council powerful bosses who are making questionable choices.

What can we do to council people in power, even well-intended ones, who have lapsed in judgement or who truly may be a “terrible” person?

It’s not easy.

In my experience, here are a few things to contemplate:

If a boss makes a statement like “I am a terrible person”, believe them:

Don’t simply shine over comments like that: dig in deeper, ask questions, get a better understanding of what they mean.

Although your boss may not really be a terrible person, they may be engaging in terrible things.

These are red flag statements HR pros need to get a better understanding of.

A professional acquaintance once told me in a moment of vulnerability: “Dawn, deep down, I’m really a huge a**hole.”

My immediate response was to soothe them with statements like, “No you’re not”, “Give yourself more credit”, and the like.

I learned later, this person in several situations treated people very poorly, lacked empathy and was a jerk in professional situations.

Although not a terrible person, this person was, indeed, a huge a**hole.

Had I taken their comments more seriously, I may have been able to block and tackle some bad situations.

Understand your “accountability” relationship with the CEO early: In your HR leadership role, it is part of your job to create common-sense accountability processes to ensure all are treated fairly.

Some processes could include coaching and counselling employees whose behaviours may be off-point, including your CEO.

For a variety of reasons, this can be extremely difficult, or in the very least uncomfortable.

To be the most effective, establish this part of your role with the CEO very early.

Openly discuss the importance of this check and balance, how it will benefit them, and establish some communication ground rules — together.

This builds rapport and trust.

This may seem a little formal on the front end but will save you a world of pain when you do have to “hold a mirror” up to a CEO who may be going down a road to nowhere later on.

When you do have to have a difficult conversation with your boss, practise beforehand: This is a great tip to use before you have difficult conversations with anyone, but even more so when it is your boss and/or the CEO.

This is not a time to mince words or drag on.

Be short, sweet, to the point, and have some credible data with you.

Also, if you’ve established your accountability relationship early, hopefully you’ve built enough trust that these conversations, although uncomfortable, are welcomed.

Don’t be a wuss: Don’t wait until your CEO has put themselves in a crisis situation before you say something.

There is nothing worse than tippy-toeing around having crucial conversations with the CEO for your entire career and then one day doing a truth-telling explosion.

Trust me, this doesn’t go over well.

However, this doesn’t give you free rein to continuously be your CEO’s nagging mum.

Let your CEO fall: Sometimes powerful people just don’t listen.

If you’ve done all you can, if you counselled them, provided data, recommended solutions, offered help and you’re boss still isn’t getting it, then let them fall.

This is especially true if your boss lands squarely in the high-ego, low-empathy category.

No amount of trust-building or heartfelt helping will solve their problem.

Engage with the CEO or leader who has issues.

Do what you can, and if the end is near, make sure you don’t become collateral damage.

* Dawn Burke is founder of and advisor for Dawn Burke HR. Her website is DawnHBurke.com.

This article first appeared at fistfuloftalent.com.

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