What Do You Owe a Difficult Boss?

This is a free preview of a paid episode. To hear more, visit moonshotmentor.substack.comI was having lunch on the patio at Kiwami with a long-time colleague — we'd served together on the board of the Coalition of Asian Pacifics in Entertainment — and we were debating whether to order the Kiwami tray or go à la carte. And then, I felt the energy around me shift. I didn’t turn my head, but I could see her outline in my peripheral vision. The boss who fired me. OMG, she was seated close enough to hear us order, and I was close enough I could smell her perfume. My first instinct: pretend she doesn't exist. Keep smiling. Keep chatting. Keep still. But the light-hearted parley about omakase was now nausea inducing and there was a buzzing in my ears.My boss, no, my ex-boss flagged a waiter and asked to move inside. I can't remember anything that happened after that. Here's what I know now that I didn't know then: what happened in my body had a name. My nervous system registered a perceived threat and responded accordingly — heart rate, shallow breath, the works. I was in a fight / flight / freeze / fawn moment — and caught between freezing and fawning. Why not do both when I’m under threat? What's interesting is that the threat wasn't real. I wasn't in danger. But my nervous system treated my ex-boss’ arrival as if something horrible was about to happen and I would be blind-sided all over again. Reader Question: Should I Reach Out to a Former (Not Awesome) Boss for a Job?I was reminded of this Kiwami experience recently when a reader sent me a question I suspect a lot of other people have too. He'd just learned that a former boss had landed a senior role at a new company. This was someone who had been skilled at managing up and promoting himself, but less focused on developing and advocating for his team. Now that this person was back in a leadership position, my reader found himself wondering: does it make sense to reach out? And if they ran into each other at some random place, what exactly should he do?We all know how important it is to maintain business relationships, but what do you do with the professional relationships that were genuinely complicated and triggered you into fight / flight / freeze / fawn mode? Thank you reader for such a powerful, timely question. The Tool: Friendly, Not FriendsEarlier in my career, when I was a “baby” network executive, some of the senior executives I worked with were … well, I just have to say it. They were mean girls. When I would walk on set, they literally turned their backs and formed a circle. It was the kind of thing that makes you feel like you're back in junior high.My first response was to shrink, you know a kind of freezing. I started showing up at the last minute so I wouldn't have to stand on the periphery. I avoided the spaces where they gathered. I got smaller and smaller until one day I realized: their behavior was changing mine. And I hated it.I love having authentic conversations with people. I love collaborating and solving problems together. I love being nice because I know you never know what’s going on behind the scenes with someone. So I made a different choice: treat the mean girls the way I'd treat any stranger.Friendly, but not friends. A few months later, the ringleader pulled me aside and said: I don't know how you did it, but you did it. Everyone likes you now.It was a little crazy to hear that because my goal wasn't to make everyone like me. I just didn't want other people changing my behavior or my values. I didn't like who I was becoming.. Should You Reach Out? My Honest Answer So back to my reader's question: should you reach out to the former boss who wasn't great to you, now that they've landed somewhere new?My honest answer: only you know. What I'd encourage you to do is get clear on which value you're honoring with your choice — whichever way you go. I'll be transparent though: if it were me today, I would not reach out because I now prioritize a flat hierarchy and working with people who are willing to have hard conversations in a grounded manner. But I also don't know what's happening behind the scenes in the reader’s life. Financial pressure, health insurance, a shrinking market — these are real considerations that can make pursuing every opportunity not just reasonable but necessary. There's no shame in that math.