A couple of years ago, my colleague Vince Molinaro wrote a great rant about the 10 worst types of leaders. You can read the full post here. When I came across it again, I had the inspiration to write a monthly series on how you and your team can survive under a terrible leader. This is the sixth post in that series.

The sixth type of terrible leader Vince describes is the insecure leader. These are the leaders whose lack of self-confidence affects everything they do. As Vince says “They don’t trust others. They hire weak talent. They are the control freaks in our lives. They play mind games with their employees.” They probably need proper therapy, but there’s not much you can do about that.

Of all the leaders I’ve had in my career so far, the two insecure leaders I worked for accounted for five of the worst years of my life. One reason for that is that insecure leaders are entirely unpredictable. If you catch them in a moment when they are feeling confident, they can be friendly, capable, and supportive. But the moment something triggers their insecurity, watch out! That’s when they get defensive, vindictive, and petty. It’s not going to be fun, but here’s what you can do.

It’s Not Me, It’s You

If you’re working for an insecure boss, you’re going to get yelled at, set straight, and micromanaged. Your first reaction might be to see this as a reflection of your lack of ability. When you question yourself and wonder what you could possibly be doing wrong, don’t exclude the possibility that the only thing you’re doing wrong is threatening your boss with your strong performance. Having the right mindset and staying centered in your own self-esteem is critical. Let me say that again, never let a boss rock your belief in yourself.

Keep Him Whole

Triggering your boss’ insecurity is only going to create misery for both of you. Instead, find ways to let your boss feel that he is in control. Where you have success, make him a part of it. “Thanks so much for the discussion last week; it really got my ideas flowing.” Where you think change is necessary, use language that shows you respect your boss’ power and position. “We need to change how we interact with the marketing team. How are you thinking about our relationship with them?” “What do you see as the biggest opportunities to change things for the better?”

Find Other Outlets

If you’re stuck with an insecure boss, you’re not going to be able to go to her with all your whiz bang ideas for how to make things better. Insecure bosses tend to like the status quo because at least they know they can keep their heads above water in the present scheme. But shutting off your brain for a couple of years isn’t the answer. Instead, find sponsors in the organization who will include you in other forums and projects.

Build Your Own Reputation

I hate to say it, but building these relationships isn’t just about flexing your brain every once in a while. Your insecure boss might be downplaying your strength to his boss and in talent reviews. That’s why it’s important for you to have your own relationships with key stakeholders. Be careful though, your participation outside the team will feel threatening to your boss so you need to keep your boss in the loop.

In the end, the best leverage you have over an insecure boss is to make yourself indispensable to the organization. If you do that, your boss will know she’s safer with you than without you—and that matters to someone who is insecure. As long as you’re willing to share the spotlight and reflect some of your success on her, your job will be unpleasant but secure.

I have to empathize that working for an insecure leaders is almost as bad as it gets. You’re trying to maintain your own self-esteem in the face of continual attempts to undermine it. At the same time, you’re trying to feed the insatiable beast that is your boss’ fragile ego. I’m not sure this situation can be tolerated over the long haul, but these techniques should calm things down and make you insecure boss bearable for a while.


See other posts in the series

Working for an incompetent leader

Working for a wimpy leader

Working for a lazy leader

Working for a childish leader

Working for a selfish leader

Further Reading

How to Disagree with your Boss

Standing up to Powerful Bullies

When your Team Needs a New Leader

4 Responses to How to work for an insecure leader

  1. James H

    I had a boss like this in the graphic design field. It’s an extremely toxic situation which made me feel horrible. I delivered some of THE biggest jobs a designer could be given, because it was what I was asked to do. While trying to do good work for the company and my boss, my boss was relentless in trying to make me look poor, picking up on tiny mistakes, speaking out loud, turning other workers against me, favoritism, isolation tactics, crushing my concentration to a pulp… I suspect very strongly he had his own pressures behind close doors with his boss. I eventually felt trapped, manipulated, stranded in an environment rife with office politics, fearful of survival, fearful of reporting to HR. Meanwhile trying to keep a strong mentality in trying to focus on my work but after a good years work I get a horrid end of year review, punished for any successes I had. With a performance review looming, I got my head down working hard, all the while my boss had been busy office politicking and brown nosing. After completing and delivering a few more top quality big jobs and avoiding being dismissed for petty typo’s along the way, I was eventually fired for something I didn’t do, nothing to do with my work itself. Harassment of a female colleague myvmanager was having sex with, PA to the Director. Corporation corruption and an insecure manager at its finest. A horrible time in my career. I’d wish that upon no person. Get out while you can before it’s too late!

  2. Kaitlynn

    “Control freaks in our lives”, “they don’t trust others”, “they hire weak talent”, “they play mind games with their employees”, “they probably need proper therapy, but there’s not much you can do about that”….I don’t know if I can disagree with this any more then I already do.

    I’m currently working for a boss who has low self-esteem, but none of this describes her at all, and she doesn’t yell either. My boss is how she is, and I’ll do anything I can to help her. Low self-esteem can be caused by anything, and for my boss it’s a few things, she’s not thrilled about how she looks, since we’re a not for profit organization we rely heavily on grants, and we aren’t getting the money we need from them, and also recently we’ve had to cut back pay and hours in order to make ends meet budget wise.

    My boss is just making the best she can with what she has been given, she rarely does anything for herself, it goes like this: clients and their families, employees, then her, and while that may not seem like she’s at the very end of the totem pole, she is, she always wants to do things for others before she does anything for herself, she gives more then she takes.

    She’s modest, I gave her a donation out of my pay cheque last month, she was hesitant to take it (even though we needed, and still need the money), but she took it after I explained my reasoning behind it, and of course she said “you don’t get paid a lot as it is”, I told her that it didn’t matter to me, that she had put so much of her time, love, energy, and own personal money, into making her organization awesome, and that it was about time that something was done for her.

    I might not get paid a lot, but my boss doesn’t get paid at all, that’s another reason for her low self-esteem, she is emotionally invested in the organization that she won’t stop working hard for it (even though she doesn’t get paid), I’ve told her that if I could I would give her half my pay cheque, because I just want to help her out.

    In case you’re wondering, I did take Social Service Work in college, and have always put the feelings of others before my own, and the needs of others before my own as well, that’s why my boss and I get along so well.

    So in short (lol, not really, since I basically wrote a novel), I don’t agree with the quotes I opened with, especially not in the case of my boss, if you knew her, you would see what I see, a sweet, caring, compassionate, selfless, hard working woman, who is a force to reckoned with, but she’s a stressed out force, that needs a little cheering up from time to time, and if I am able to do that, or just be there when she needs to talk, then I’m happy to do so.

  3. Mary

    If I smile I am judging or being condescending, if I have no expression I am not paying attention, if I am too attentive then I am also being too condescending. If I ask a question I am challenging, If I am silent I have not heard or am hiding something. If I stand on the left of her rather than her right I am not paying attention. If I do not yield to her path of movement I am in her way. If I tell her something I was keeping something from her and should have told her earlier. If I begin an activity without her direction I am undermining her authority, if she can’t find something than I have moved it. If she can’t understand something than I have confused it or broken it. If I have a suggestion she must own it and then change it.
    It has been almost two years now. I have learned a lot of how to cope in such a situation but sometimes it is just way too much effort. The business is closing soon I wonder why?

  4. Concerned

    This is the second time in a row that I am dealing with an insecure boss. The first was an unyielding, sociopath who micromanaged me and despite my being a yes person to her, I was fired in the most horrific way. I now work for another insecure person. This time around the boss is fully incompetent, nice person, but the worst decision maker who is slowly destroying the company. This is a boss who is afraid and sees me a a threat. I am vying for an upgrade and realize that more than anything, I have to stroke my boss’ ego in order to get a job that I actually deserve, can do well and would benefit the company to have. I realize that I have to reassure my boss that he is great and that promoting me would, once again, prove what a great leader that person is.

Leave a Reply

Your email address will not be published. Required fields are marked *