The Anti-Mentor

A bad boss shapes our leadership style more than we realize.

Who’s the worst boss you ever had?

Your answer to this question matters. It influences your leadership style in more ways than you think.

For myself, I can answer that question, “Who’s the worst boss you ever had?” almost immediately.

He’s someone I’d worked for coming out of college, after I’d started my first company. You’ve likely met a variant of him before: One of those leaders who looks you steadily in the eye, and with complete conviction and charisma, articulates a beautiful vision of the future the two of you could create together.

Back then, I nodded my head, convinced.

He then turned around… and he didn’t follow through on what he’d promised. He played favorites. His mood temperamental, at best. Ask a question, make a suggestion, offer a new idea – and he appeared irritated that you dared to speak up.

He wasn’t a bad person (he was a lovely person, in fact.) But having him as a boss showed me exactly the kind of boss I didn’t want to become. I took his template of leadership and whittled my own – a relief carving in opposition to his.

This worst boss of mine is what some would call an “anti-mentor.” Far from the person who you aspire to be like, they are who you avoid emulating, at all costs.

To this day, my “anti-mentor” influences my actions as a leader. For instance, I go to great lengths to be immaculate with my word. I’ve witnessed firsthand how destructive it is to say one thing and do another, as a leader. I strive to be unabashedly fair and consistent, because I’ve noticed how much instability and low motivation an unpredictable leader injects in a team. And, to this day, I’m highly conscious of creating an environment that encourages people to share divergent opinions. I’d seen what happens when the leader expects honest feedback to come to him – he never hears it.

When I reflect on my own leadership style, I realize that the bad bosses I’ve had influenced me more than any good boss I’ve had. Seeing what you don’t want to be like is more powerful than what you dowant to be. The push is greater than the pull.

Psychologist Frank Oser calls this “negative morality” – learning from mistakes is markedly more powerful than learning from successes. However, you don’t necessarily need to experience the mistakes yourself to feel its impact. In the book The Moral Advantage, William Damon explains how the people he interviewed often cited the “anti-mentor” for shaping their values more than any other positive example or role model.

In this sense, an “anti-mentor” is a gift. My experience with my worst boss was a clarifying force. It helped me understand what I valued as a leader and as a person. Resistance shapes you. When know what you’re against, you more firmly know what you’re for.

At the same time, “anti-mentors” have unintended, adverse consequences when you model your leadership style in reaction to them. You can easily – and unknowingly – overcompensate. For example, my worst boss was never sensitive about extenuating life situations of his employees. If someone’s kid was sick, if something tough was going on in life, it was, “Well, that’s too bad. Can you get this done ASAP?” As a result, with my own team, I’m exceptionally generous about the time someone can take off. Sure, that’s good in the right doses… But I think in the past, I’ve been too liberal with it. There are people I’ve worked with who’ve taken advantage of my overly generous tendencies, and left our team worse off.

Most commonly, I talk to many leaders who have a problem being too nice because of their “anti-mentor.” Their former boss was as asshole and they are scarred by that experience. But inadvertently, now as a leader themselves, they lean the other way too far. They can’t bring up hard conversations with their staff. They have difficulty firing people who needed to have been let go months ago.

Whether or not you’re positively or negatively influenced by your “anti-mentor,” the critical thing is to realize that you are influenced by this person, to begin with.

Ask yourself: Who is the worst boss I’ve ever had? Then reflect. In what ways are you consciously or unconsciously reacting to your experience with this person? Are those reactions to this person – your “anti-mentor” – helping your team? Or, are they hurting?

Your worst boss is with you in more ways than you think.


Claire is the CEO of Know Your Team – software that helps you become a better manager. Her company was spun-out of Basecamp back in 2014. If you were interested, you can read more of Claire’s writing on leadership on the Know Your Team blog.

4 thoughts on “The Anti-Mentor

  1. So true. It definitely affected me while I was there, but I will say anti-mentors make you aware of what doesn’t work and sometimes that’s as important and knowing what type of leader you want to be.

  2. I agree with most of what is said, but I disagree that you are shaped more by what you don’t like than what you do like. I (wonderfully) have a little trouble digging up a bad boss, but I can easily dig up in my mind a number of incredible bosses. When I think back on the kindness, generosity, and understanding I received from my wonderful bosses, it encourages me to be that way to my own subordinates.

    I would argue it’s probably whatever is more impactful that affects you — sure it could the negative boss. The anti-mentor. But it could also be the most incredible boss you’ve ever had, the most inspiring mentor you’ve ever worked with.

    I think the most important message in this article is to ask yourself “you _are_ influenced” by someone. We are all influenced and it’s important to realize that.
    Further, for everyone we are watching and learning from, understand someone else is watching and learning from us.

    We are all role models for someone, whether we want to be or not. Remembering that helps me take the time to figure out the right thing to do (and apologize when I’ve done the wrong thing!)

    1. There is no edit button, so I just wanted to clarify, I realize the author didn’t explicitly say we learn more from negative experiences than positive.

      I think it’s somehow implied. I also get that — I learn more from my mistakes that my success. In fact, I tend to attribute my success to just me being awesome. When I make a mistake, I am more likely to introspect and figure out what I did wrong, what can I do to fix it.

    2. Speaking of remembering your favorite bosses, I only remember my favorite teachers from high school and not the ones I disliked. I think this argument could go either way. In my experience, fewer teachers and mentors have stood out more for the reason they were so great. On the other hand, if most of the bosses in your career were great, anything less than good would surely stand out.

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