The Corporate Shrink

How to deal with an Eeyore employee?

By Kerry J. Sulkowicz
Featured on FastCompany

As head of human resources for a small public company, I will be supporting our recently hired CEO. What’s the biggest leadership challenge she will face, and how can I help? (issue 98, page 90)

I can see it now. When asked to name the single biggest challenge a new CEO will encounter, I’ll pick one and then get swamped with email saying some other challenge will be the biggest test. But in my work as an adviser to the boss, one theme emerges most frequently. The toughest part of the job for many CEOs, new and old, is the isolation and loneliness that comes from being alone at the top.

That may sound surprising to you, especially since CEOs often have entourages so big they rival P. Diddy’s. Remember, though, there’s a big difference between having a lot of people around and having a few confidants – or even one – with whom you can speak intimately. CEOs can’t open up in the same way they once might have with peers. Rather, they grapple with some of the most ambiguous, complex problems in business — often without objective and frank sounding boards.

Because people problems can be the thorniest of all, as head of HR you can help your CEO feel less alone by offering yourself up in this crucial role. But be patient. It takes time to develop this kind of trusting relationship with a new boss, and it may be necessary for her to look for confidants outside the organization.

We all have a need for intimacy. It’s hard enough to find it with people we consider our equals. The challenge for leaders at the very top is that they don’t have any. Some CEOs don’t like to admit how lonely they feel, but the ones who can articulate the emotional experience of being leaders – and seek help for dealing with it – tend to be more successful, especially in the long term.

One of my employees has an Eeyore complex: Everything is negative for her. She thinks she’s about to be fired any minute. Along with her low self-esteem, she collars colleagues in the hallway, complaining about her heavy workload. Encouragement and support don’t work. How do I motivate her?

Sounds like you have quite the gray cloud in your office. By saying this woman has an Eeyore complex, you make clear she’s causing annoyance and irritation through her stubbornness to remain downbeat. I understand your frustration: Employees like this make others feel helpless and, ultimately, angry.

So what should you do? Since encouragement and support haven’t worked, help other employees learn to be more empathetic. Appreciating her quirkiness, rather than calling her Eeyore, would be a good start. Then, try to find a way to turn her stubbornness from a weakness to a strength.

If that doesn’t work, it’s possible that your employee is clinically depressed or has a personality disorder, in which case suggesting she seek “professional help” (that wonderful euphemism for psychiatric treatment) could be a good idea. Skilled therapy, and possibly medication, could make her less gloomy to be around, and more of a pleasure to have on your team. However, if her demeanor is bringing down employee morale after repeated attempts to help, or if she won’t seek treatment, she may need to be dismissed.

Dr. Kerry J. Sulkowicz, a psychiatrist, psychoanalyst, and founder of The Boswell Group LLC, advises executives on leadership, management, and governance. Send him your questions about the psychology of business (