How to survive mixed up management

Dear OMFG,

Your letter reminded me of Mary McGregor’s 1976 prog-pop song Torn Between Two Lovers. If we retitle it Torn Between Two Bosses it can become the unofficial anthem of every banker who has ever been caught in exactly your kind of squeeze.

“Lovin’ both of you is breaking all the rules,” she sang. While your situation is decidedly less romantic (at least I hope so!), the bind is the same. You’re being asked to show allegiance and loyalty to two different parties who want different things from you. Pretending otherwise won’t make the problem go away.

Let’s be honest about how these things actually get resolved in our business, which is to say: they often don’t.

Your instinct is probably to get everyone in a room and hash it out. Noble idea. You can absolutely suggest it, but the reality is that investment banking is full of smart, aggressive, highly paid, uber-ambitious people who, for all their alpha qualities, are remarkably allergic to direct confrontation unless their own P&L is on the line.

Your boss and his overlord don’t have a strong personal incentive to sit down and align on what you should be doing. It doesn’t hit their comp. It doesn’t affect their year-end. For them, the ambiguity is fine — you’re the one losing sleep over it, not them.

While a pow-wow is worth proposing, don’t count on it producing the clean resolution you want. More likely you’ll be expected to mediate and manage the competing demands yourself and make it look easy.

Which brings us to the real question: if you must pick a lane, which one?

I can’t tell you that in the abstract because I don’t know the personalities and the specific texture of your office. But I can tell you how to think about it.

Forget, for a moment, who’s more powerful or who “sponsored” you in. Those matter (sort of), but they’re not the deciding factor. The deciding factor is: which role gives you the better medium-to-long-term story? Which one puts you closer to revenue? Which one has a clearer promotion path? Which will make you more valuable in a few years’ time — either at this firm or the next one?

Sponsors are wonderful right up until they resign, get pushed out, or lose a political fight, and then you’re left with whatever franchise you’ve built for yourself. Build the franchise that travels.

A few practical pieces of advice.

First, don’t frame this to anyone as picking sides. That’s a losing narrative. Your job is to keep as many people happy for as long as possible.

Second, try to position whatever you do as responding to the business’s needs as you understand them. Keep your boss close and informed; if you’re drifting toward what the higher-ups want, she shouldn’t learn it from someone else.

And finally, document your conversations — not in a paranoid way, and not to create a litigation file, but rather to have a clear answer if or when someone eventually asks why you spent six months doing X instead of Y.

You won’t get everyone on the same page. Your job is to make a defensible bet on where the value is and then execute.

To paraphrase Wayne Gretzky, go where the puck is going to be, not where it is.

For real,

Craig