Workplace Jiujitsu #1: Never Sidestep Your Manager

Trust breaks down when reporting lines are skipped. It's a pattern that I've seen over the last decade, especially in fast moving companies. The lesson: Never Sidestep Your Manager (Even When You Think You Should).

For example, startups love hiring bright, energetic grads straight out of college. They bring fresh ideas and are bold. But they are also inexperienced in the workplace and are barely learning how to work. Their enthusiasm can get ahead of them and this is where things can go wrong.

Let's look at a scenario using characters from The Office:

Ryan Howard: the excited new hire Michael Scott: the manager that gets jumped over David Wallace: the CFO

Ryan sees a broken process. It's inefficient, obvious, and fixable. He takes the initiative to pitch a solution directly to David. It's low hanging fruit. David gives it the green light.

Michael, Ryan's manager, learns about the change later when he's tasked to implement the solution. He sees the flaws. It's not practical. But David is already on board. Pushing back means pushing up hill.

Michael starts pulling back. He loses trust in Ryan. He's less invested in developing him. A year later when Ryan asks for a raise, he gets 3% for meeting expectations, not 10%.

Ryan lost career momentum. It wasn't because Ryan's idea was bad. It was because he sidestepped his manager and broke trust.

Trust moves through layers even in companies with a flat hierarchy. When you skip one, you might get hit with unexpected resistance.

It's not about ego. It's about structure. Your manager can be your biggest advocate. If they feel cut out, they may also become your biggest blocker.

When you have an idea, bring it to your manager first. It's not to ask for permission. It's to build trust. Share your thinking, ask for input, and see if they want to sponsor your initiative.

You might only get a few chances to drive change. Don't waste them by going alone.

If you’ve seen someone get ahead of themselves like this (or maybe it was you), I’d love to hear more about it.