Box of Crayons Blog


What to Do When Your Boss is Crazy

I’ve had one, you’ve had one, we’ve all had one… at some point in your career you’ve encountered a boss who is perhaps a little bit nuts. Or evil. Or nuts and evil. It can sometimes make work feel like you are walking on egg shells. And, that can be hard to deal with. Little wonder the saying “you join an organization but you leave a boss” is so common in the workplace.

Take heart. There are ways to deal with that insane superior of yours. In this video I share three tips for helping you stay centred, calm and “in your own lane” including:

  1. The most counterintuitive move you can make.
  2. The Drama Triangle and the three key roles.
  3. And, why it is critical that if you are going to suffer, you need to suffer with intent.

Watch the video, or download it as a free podcast on iTunes and see below for key takeaways and extended notes.

Or you can listen to this podcast online.


If not now, then eventually you will find yourself working for (or with) someone who is crazy. In order to keep your own sanity, here are some things I’ve learning in my journey with a crazy boss. Number 1: Discover why one of the best things you can do is to begin with a foundation of empathy. Standing on someone else’s shoes is a good way to understand their struggles. Number 2: Understand your own role. What actions (or reactions) of yours feed the cycle of negativity. What adjustments can you make in your own actions to be the best version of yourself, and hopefully support a more harmonious relationship? Lastly, Number 3: If it just isn’t going to work, you need to get out. What’s your plan, and what can you learn along the way to make sure your next move is your best move.

Don’t forget to rate this podcast on iTunes.

Full Transcript

So you’ve probably heard the saying that you join an organization but you leave a boss. And I know that when you think back on your career so far or the career you’re having right now, you may be thinking to yourself, “I’ve had some fantastic bosses. Bosses that have supported me, coached me, stretched me, pushed me, provoked me,” done all the things that help you expand and increase your impact and your capacity as a human being. Fantastic.

But you’ve probably already had a nutcase boss because we’ve all had those bosses that make you want to pull your hair out. I think back on the time I’ve spent working, and you know, I’ve been my own boss for many years now at Box of Crayons and, quite frankly, I’m not a very good boss to myself even, but when I think back to when I used to work in organizations, I had one boss called Red Dot. You know that moment in a movie when somebody trains a laser rifle on somebody’s head and this little, red dot appeared? That was her management style.

We were in a tough time, working through some change processes, and when Red Dot would happen, the rest of us would kind of back away as fast as possible to avoid the evisceration that was just about to happen. I had another boss whose nickname was Napoleon. He was short. He was a bit of a megalomaniac. He wasn’t a terribly good boss.

So we’ve all had those bosses that make you go, “Why am I even showing up for work?” And the question is what do you do when your boss is crazy? Well, look, it’s tough. I know that. But I’ve got three that I’m going to suggest to you that just might make it a little easier for you.

And the first is, and this will sound almost counterintuitive, is actually to be compassionate about that other person. Because as I say, everybody’s fighting their own battle and your boss, as crazy as she might be, or as crazy as he might be, she or he is probably up against something and they’re struggling with it. And one of the processes that I use that might be useful for you is to understand what would it be like to stand in their shoes, sit in their seat for a moment and go, “What is going on from their point of view?”

You know, you see the world from your point of view. That happens naturally. It’s really powerful to step across the desk and actually start going, “If I was her, how would I be seeing things? How would I be seeing the situation? How would I be seeing that person who’s you and getting to a bigger understanding of that?” What I notice when that happens is, A, I feel immediately more empathy for that person, like, you know, “Wow, you’re up against more than I imagined.” I once heard somebody say their job is always a lot easier when it’s their job. “As soon as I got it, it became way more difficult much more quickly.” So that’s the first point for you, is feel compassion for this person. See if you can actually sit in their chair, stand in their shoes for a brief moment, and get a sense of what’s going on for them, because that will help you understand perhaps some of their erratic behaviour.

The second tactic that I would share with you is to understand your role in all of this. And to do this, I often teach a model called the Drama Triangle. Its basis is in transactional analysis, but it was developed by Stephen Karpman to have a really simple way of understanding a dysfunctional dynamic. And we can’t go too deeply into it now, but I want to share the three key roles. The three key roles are persecutor, victim, and rescuer. So you can guess what those roles look like. Persecutor, that’s probably Red Dot or maybe Napoleon. You know, the kind of finger-waggling, blaming, shouting, or kind of micromanaging perhaps. The victim role, you know what that looks like. The, “Oh, it’s so hard. It’s so difficult. It’s not my fault.” It’s always somebody else’s fault. And the rescuer is the leap in, fix it, solve it, “Let’s avoid the conflict.”

And when we’re working with a crazy boss, sometimes it’s easy to think that the issue is all about them rather than it’s an issue about you and their relationship together. So let me ask you this question: when you bring that crazy boss to mind, what’s the role they play in the Drama Triangle? And now you see that; what’s the role you’re playing in the Drama Triangle? Because both of you are in the Drama Triangle right now. So the key insight here is to understand what your role is in the Drama Triangle and see how you can get yourself out of the Drama Triangle so you play that role less often. So this is all about going, “It’s not just about them, you’re in this as well. How are you going to manage your reaction so you keep showing up as the best version of yourself?”

The third tip that I would share with you around how do you manage the boss is to say this. Look, you probably need an exit plan, so start thinking about what your possibilities are. Can you leave this job? Can you leave this role? Can you leave this organization? And so, build the exit plan. But of course, you may not have that exit plan or you may need to wait for a little while. So then, the case is how do you extract the learning and the stories from what’s happening now? Because if you’re going to suffer, make sure you suffer with intent.

So as you go through this process, what are you learning about you? What are you learning about leadership? What are you noticing about things to do differently when you’re with your next boss or the way you show up and manage the next team that you’re working with?

So extract the learning and extract the stories because people love stories. That’s how people learn, by telling stories, by seeing the story that they’re in. So this is an opportunity, even as it’s a struggle, for you to actually say, “What am I learning here? What am I taking away from here?”

I mean, when I think back to one of these bosses I was telling you about before, Red Dot, every Friday afternoon I would sit down for twenty minutes or so in a meeting room or sometimes down in the cafeteria, and I would say, “Okay, what’s happening between her and me in the Drama Triangle at the moment? What am I learning from that? Okay, what experiences am I picking up from here? What is this telling me about me?” And even though it was a pretty tough six or seven months working for her, what I found is it actually gave me a great—a much more clear sense of self and a much clearer sense of what good leadership and great leadership can look like for the next roles that I stepped into.

So the key takeaways. If you haven’t had a crazy boss yet, your time will come. Believe me. They’re out there. But rather than giving up and despairing, the three tips would be this.

First of all, feel some compassion for them. Stand in their shoes so you have a sense of what are the battles they’re against. Secondly, understand the Drama Triangle and understand what role you’re playing in all of this. It’s not just about them, it’s about you and how you can manage your own behaviour. And thirdly, as long as you’re there, extract the learning, extract the stories, and that’s the way that you can use a crazy boss to help you do less good work and more great work.

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