How to Survive Working for an Oversharing Leader

Are you working for a C.E.Bro?

You could feel the collective cringe around the office. He had that look in his eyes again. The “I want to share something with you” look. Everyone followed orders and gathered around the bean bags and ping pong table. The story began.

“3 years ago, I took a $50,000 loan to keep this company afloat.”

I was pretty sure it was $40,000 the last time he told this story. Interest rates were out of control in his imagination.

“Can you even imagine the amount of pressure that puts on a person? I fought constantly with my wife. My relationship with my brother broke down because of money. We held off on having children until well into our 30's.”

Nobody wanted to make eye contact with each other. Our C.E.Bro continued his story.

“So the next time you have to work a weekend to get a client presentation just right, remember that we’re all making sacrifices here. We’re a family and that’s what families do for each other- they make sacrifices.”

It was 9:13 am.

Having had our morning dose of vulnerability and authenticity, we trudged back to our desks as most families do after an unpleasant journey: hungry, irritable, and confused.

Does this sound familiar?

If the above experience rings a bell, you may have worked for a C.E.Bro in your own life. What’s a C.E.Bro? Well, I’m glad you asked.

The C.E.Bro is a narcissist with an Audible subscription. They’ve read every self-help book that’s been written in the last 10 years (or listened to it at 2.5X speed while doing fasted cardio). They can rattle off David Goggins and James Clear quotes at the drop of a hat, and say the word ‘purpose’ at least 3 times before their first matcha tea of the day.

C.E.Bros have watched this Steve Jobs video about the secrets of life about 437 times, and they’re convinced that they’re on a mission to change the world with their digital marketing agency, Shopify store, productivity app, or something equally unoriginal.

Somewhere along the way, they got convinced that sharing their vulnerability makes them authentic leaders and helps to earn the trust of their employees. So they went to the opposite extreme of their stoic grandfathers’ generation. The strong, silent type that Tony Soprano looked up to has been replaced by the vulnerable, over-sharing man bun that considers every insecurity of theirs as a burden for their captive audience to bear.

And there is no better captive audience than a room full of people whose livelihood depends on you.

Hang on, being vulnerable is bad now?

I know you might be thinking, “But Ali, isn’t showing your vulnerability as a leader a good thing?” I apologize for making you sound like you’re from the Brady Bunch.

The answer is, it depends.

Does sharing your vulnerability help others find strength? Does it help others feel less alone in their struggles and inspired to carry on despite feeling afraid? If so, then there might well be a case for you to share your personal struggles as a leader. And even then, only if your stories have an uplifting ending, so they give the audience hope, rather than making them feel like they’ve now got another family member’s troubles to carry through life.

In his book ‘Steal the Show’, public speaking coach Michael Porter talks about the nuances of when to listen, when to share, what to share, and with whom to share, as a leader:

“It’s important to listen actively, to be curious about others, and to have a sense of proportion about how much you talk about yourself. We don’t need to know the details of Sam’s late-night rendezvous or how Susie feels like she isn’t worthy of the promotion she received. The former is inappropriate and something that Sam should keep private. The latter is self-destructive and should be discussed only with trusted mentors and advisors in order to overcome it; Susie could lose credibility with her subordinates if she discusses it with them.”

Your subordinates are your responsibility — not your therapists.

Where most leaders go wrong with oversharing

Organizational communication experts Lisa Rosh and Lunn Offerman wrote an excellent article on this subject in the Harvard Business Review, where they categorized the hundreds of leaders they had seen struggle with oversharing into the following:

Oblivious leaders

These leaders don’t have a realistic view of themselves, so when they share their opinions or reveal personal information, they come across as tone-deaf, or even worse, dishonest.

E.g. CEO Sandra shares a heart-rendering account of being bullied by her first manager, only for her employees to roll their eyes because they’re the ones usually being bullied by her.


Bumblers may know themselves a bit better than Oblivious Leaders, however, they’re really bad at picking up social cues such as their colleagues’ body language and facial impressions. So their ‘authentic’ disclosures end up falling flat.

Rosh and Offerman give an example of a senior American management consultant who was asked to coach an underperforming team in his firm’s Asia-Pacific office. He shared stories of his own failures in the hope of gaining their trust but failed to realize that he was losing the room- his Asian colleagues thought he was weak AF and incompetent. Brutal.

Open Books

Open Books just can’t stop talking indiscreetly about themselves, or about others. They have zero filters. And while this trait may come across as warm and accessible at first, it soon becomes a bit too much. People find it hard to trust you when you just can’t shut the f*ck up.

E.g. management consultant Jeremy lost his job because he detailed all his previous failed projects to a prospective client in the hope of disarming them and earning their trust. Unfortunately, he found that the Eminem 8-Mile final battle approach doesn’t quite work in management consulting.

You’ve just described my boss. What do I do next?

Find a new job.

And if that’s a little tricky right now because the world is ending, then here are some tips from my own experience, as well as from people much smarter than me, for when you get cornered by an oversharing boss.

Do NOT fall for the reciprocation trap

You might think you need to share your own personal stories because your boss is being vulnerable to you. Don’t do it. I’ve been in the leadership team at a couple of marketing agencies- those stories come up, and HR is usually in the room. Enough said.

Don’t joke around too much with your boss either- especially at their expense. That’s how I lost my last job.

Be straightforward

Julie de Azevedo Hanks, a psychotherapist and author of The Assertiveness Guide for Women says that it’s possible to let your boss know that you don’t want to know more about their personal life without being rude. She suggests using phrases like “I feel honored that you trust me, but I’m not sure I should know this much”.

Of course, you’ve got to follow up swiftly with a change of subject.

Redirect the conversation

Change the subject back to something work-related as soon as possible, and try engaging their brain with a specific question, rather than a generic comment.

Say your boss has just told you that his wife hates their baby- you could say:

“I’m so honored that you trust me enough to tell me that. However, I can’t help but feel that I shouldn’t know this much about your personal life.”

Then smile.

And then say something like “Can I ask you to review the outline of my presentation to the board next week?”. Or whatever it is that you do for a paycheck that got you into this position in the first place.

Closing thoughts

If you work for a man bun wearing, vulnerability wielding oversharer of a leader, do not despair. You‘re not alone. And you’re not a bad person for wanting your time at work to just be about work and not people’s life stories.

If you do find yourself trapped in an oversharing situation with your boss, however, try practicing the authenticity jiu-jitsu moves outlined in this article. They may just help you survive. And then when you launch your own business, you could tell your employees the story of how you survived a nightmare boss.

No, but seriously, please don’t.

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