Leadership Insecurity is “Catching”

Have a boss that’s insecure[1]?  You’ve likely got it too. 

Elisha is a senior leader who has a great mistrust for her CEO.  She says he’s fickle with his approval, oscillates between extreme micromanagement and total hands-off approaches, and recently discredited a 360 assessment she undertook when he realized his ratings were all low while all her peers and direct reports rated her highly.

Unfortunately, much like COVID, insecurity is highly contagious. And while Elisha doesn’t have the same “symptoms” per se, her case of insecurity has worsened: 

  • She tries to avoid her boss with a head’s down approach, thinking that if she does work that is beyond reproach, she’ll be ok;
  • She gossips about her boss with her leader peers and then feels angrier;
  • She convinces herself to tolerate her situation because she is very well paid.

Here’s the rub.  No amount of working hard (from a distance), tip-toeing around, trying to build the boss up, or talking oneself into not caring will work sustainably.  Just the opposite will occur. Everyone, including the boss, will become more insecure and mistrustful. 

So what’s a leader to do?

At this point, you might conclude that my “cure” for an insecure boss is to quit. We are living in the time of The Great Resignation after all. 

But insecure bosses are everywhere. I am one myself at times. 

In the face of an insecure leader, most leadership advisors focus on outer game tactics like being diplomatic, finding ways to make your boss look good, making yourself indispensable, or quitting while you are still standing.  

And aspects of these points have their place. But they don’t actually solve the insecurity problem.


Because on their own they only cover up the problem. They don’t actually solve anything.

So we come back to our original question: What’s a leader to do?

I wish I had a simple, one step answer for you, but I would be lying to you trying to make this all seem way easier than it really is.

Since telling the truth– no matter how cumbersome– is one of my top values, I’m going to lay out the reality: the answer lies in five steps.

  • Gain deep clarity— I’m not talking about a fleeting aha. I’m talking about major, mindshifting clarity
  • Cultivate real self-acceptance— the kind that reorganizes your priorities and how you see yourself and your organization
  • Find your true source of courage— secret: it’s not “feel the fear and do it anyway.”
  • Figure out how and where you need to to give yourself permission
  • And get the right support to guide you. Because all the tactics and knowledge in the world will only get you 20% of the way there.

Now back to Elisha. I know her quite well.  She’s a highly creative person with a really clear vision for the life, leadership and impact she wants to have. I have every confidence that she will find a more sustainable recipe for her thriving.  She’s working these steps. She’s making progress.  And until she finds her path to thriving, I will keep providing loving pressure by holding up a mirror with her vision flashing back to her.  She’ll be able to see it clearly again when she is ready. I can’t wait!

Perhaps you’ve caught some insecurity from your insecure boss and you’re feeling unsure what to do.  Fortunately for you, you don’t have to sort this out alone.

Schedule a complementary Thrive Session today. You’ll have my full presence for 45 minutes (or Julie Ann’s). Together, we can explore how you can accept yourself exactly where you are so you can fast track your way back to Thriving. You deserve this. To your thriving! 

[1] In a recent LinkedIn poll, author and keynote speaker Liane Davey asked, “What is the worst character trait in a manager?” Her large following returned a clear answer: INSECURE.  It was voted more than any other response (ahead of angry, indecisive, or conflict-avoidant).  

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