Going Over Your Boss's Head Is Sometimes the Only Way Forward

This is a simple question I sometimes get from people who work at fairly large companies and are scheming to launch a new business inside their organization, rather than start up on their own. The pattern goes like this: “There’s something I want to do. But my boss has zero understanding of new initiatives like this. The company doesn’t even have a system for pushing through a request to change departments on your own initiative. Am I stuck?” This is a common one.

Let me pass on one simple technique. “Go to your boss’s boss.”

This is what’s known as “going over someone’s head.” You’ll be disliked. You’ll get scolded. People might say it goes against organizational discipline. I understand that way of thinking exists (screw it, though).

But here, play dumb.

There are a few practical techniques.

<Bump into them “by chance” and chat> Keep track of when and where your boss’s boss tends to be alone. If that person smokes, the smoking area is a golden opportunity. They’re sure to stop there at certain times. Act like you bumped into them by chance, walk in with them, and start talking. Then slip your pitch in “accidentally” along the way. Something like “I’d love to get your opinion” works. If they’re not a smoker, a break room works too, or a meeting room after a meeting. Everyone’s human, so there’s always some time when they want to relax alone somewhere. Catch them there.

Say you want to get past Section Chief A and talk to Department Head B. One option is to get help from a different section chief, C. First, bring Section Chief C on board with the idea. Then you can either have Section Chief C pass it on to Department Head B, or, if you get a chance to talk with Section Chief C, combine it with the “bump into them by chance” method described above. Something like: “While I was talking with C, B happened to walk by, so I had them listen too. Oops.” A similar move: if you happen to have a personal friend who’s a department head, say D, you could get D to help you too.

This is a fairly bold technique, but you just “accidentally” send it. Follow up with something like “oh, sorry, I sent that by mistake,” and then, “well, since I already sent it, let me explain what it’s about.” From there, you’re on your own.

Now, even after you reach Department Head B, the same thing might happen. You might not get understanding, and instead get told, “you should say that to Section Chief A.” In fact, that’s what usually happens. In that case,

go even higher.

Do the same thing. Keep going endlessly: section chief, department head, division head, general manager, executive director, vice president, president. This is like Othello: once you succeed in winning over just one person, everything can flip at once.

Act before you complain. Play dumb and push forward.

What if you go all the way to the president and it still doesn’t work? That’s when it’s time to quit the company.

By the way, I learned this method from Mr. A, whom I regard as my mentor from my time at a certain company. Mr. A held a department-head-level position at a listed company, so socially speaking he was a fairly respectable person. But his actual behavior was nowhere near that of a respectable salaryman (details omitted). I imitated Mr. A and used this method myself several times. Sometimes it worked out well, and sometimes it ended in disappointment. And then I went to America. From experience, this approach earns you some resentment. When that happens, play dumb, apologize, and forget about it. Don’t forget the resolve to see all of that through.

Originally published in Japanese at https://clazytech.com/2021/08/481/. Translated with LLM assistance and reviewed before publication.