Why Do Good People Keep Bad Company?

My struggle to understand how harmful leaders retain talent

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The Stoic philosopher, Seneca. Despite his wise teachings, he thought he could change Emperor Nero. It didn’t work out.

Most of us have had a friend who dated or married a jerk.

They suffer for months or years, but bear it without making a change. Mutual friends whisper about how awful their partner is and how we might somehow conspire to free them from misery. Then our friend enters the room accompanied by their dark cloud—a perma-expression of defeat and weariness. We return home pondering: Why do they stick it out?

I have several friends in such a position, but it’s not a romantic relationship I worry over; it’s their manager or CEO.

These friends are people with whom I have worked closely in amazing companies with strong leaders. They know what a safe, positive, inspiring workplace looks like. Yet they stay in jobs with leaders who openly denigrate them and rip away the agency and meaning that work once gave them.

I have spent many hours wondering why they take this abuse. This post is an exploration—with a few stories, of course...

Working for The Man Monster

Without giving too much away¹, various friends and acquaintances I have worked with are currently employed by a CEO known in the industry as “The Monster.”

He was hired by a leading Private Equity firm that took over a company I know well. Upon arrival, he proceeded to make lots of changes. This included: Personally reviews every expense report in the company, fires women as they were delivering children in the maternity ward, fails to pay earned income and bonuses, cut healthcare coverage without warning, declares certain words to be firing offenses, promotes his political beliefs through company-wide email, and directly tells employees things like, “You are insignificant.”

The Monster proudly lets his asshole flag fly and there is nothing you can do about it.

Well, you can quit, of course. Many have, but many have stayed. This breaks my heart and my brain.

And there are so many monsters out there…

A few years ago, the #MeToo movement helped shed light on the darkness that lurked in the open of many companies of all sizes. But it didn’t stop this form of predatory behavior. And it did nothing to address the countless other shades of asshole that leaders can display.

From the stories I hear and my knowledge of human nature, it seems to be getting worse.

Companies are under intense economic pressure due to the end of the “good times.” The fear generated by their private and public investors turns into knee-jerk actions that lack heart. Many are led by people who have never been forced to build operational discipline skills or employee motivation knowledge. So they follow the herd, taking inspiration from their peers and (in)famous leaders. Many have copied their models for regular RIFs and return-to-work policies that drive people out.

As just one example, my friend at a newly IPO’ed tech firm received a fresh policy memo from her HR department: Managers were now free to fire any employee, for any reason, at any time. And the standard months-long exit package was reduced to two weeks of severance.