How to Manage Up: Leadership Development in Action

Let’s be honest—working for a new or inexperienced boss can be tough. You want to be supportive, but when every project feels half-baked and you’re constantly resisting the urge to roll your eyes, it’s hard to stay motivated.

One viewer recently asked:

“Jenn – My new boss is nice, but new to leadership—and honestly, their ideas aren’t great. Every project they hand me feels poorly thought through. I don’t want to seem difficult, but it’s hard not to roll my eyes at every detail. How should I handle this?”

Oof. Sticky situation.

Boss dynamics are always challenging, especially when you find yourself more experienced than the person leading you. It’s frustrating to receive vague or poorly scoped assignments, and even more so when you’re trying to be a team player.

But here’s the thing: pushing back isn’t the problem. It’s how you push back that makes all the difference.

Start with “Yes” (Then Shape the Outcome)

When your boss hands you a less-than-perfect delegation, try responding with something like:

“You got it! I can already feel my wheels turning on this one. Can I set up time with you in a few days to share my initial draft thinking and any insights that pop up once I dig in?”

This kind of early check-in does three powerful things:

• Builds trust by showing you’re supportive and proactive.
• Creates space to share your expertise and prevent rework.
• Opens a window into your boss’s thinking—maybe there’s context they forgot to share.

Of course, this approach isn’t universal. If a request is unsafe, unethical, or likely to cause defects or burnout, a different conversation is needed. “Starting with yes” doesn’t mean saying yes to everything.

Managing Up Is a Skill

There’s a whole world of advice out there on “managing up,” and for good reason. Leadership development is relevant for anyone navigating difficult team dynamics (not just executives). It’s all about communication, clarity, and mutual success — and these skills take practice.

When your boss is still learning, your ability to guide, clarify, and collaborate becomes even more valuable. When done well, you are no longer simply executing tasks, you are helping shape how the work gets done.

So next time you get a confusing assignment, take a breath, start with curiosity, and use your voice to co-create a better outcome.

Til next time—happy improving!

 

This post is a summary based on the transcript of a recent episode of Go Ask Jenn. You can watch the entire video here.