How to manage up without people pleasing

Picture this scenario: a leader, I’ll call her Rachel, sat in a meeting nodding along as her boss outlined a major shift in priorities. Again. The third shift in the past six months.

Deep down, she knew what he was asking wasn’t realistic. But in the moment, her people-pleaser instinct kicked in. She said yes—even though she knew it was the wrong thing to do.

As soon as the meeting ended, regret set in.

"Why did I do that? I knew it wasn’t the right call."

Rachel swore to herself then and there: never again would she agree to something she knew wasn’t in the best interest of her team just to avoid conflict.

But she also didn’t want to go back to her boss combative. She knew she needed a different approach—one that would open the door for negotiation and co-creation, rather than a power struggle.

How Rachel Took Back Her Power

Before going back to her boss, Rachel did something different.

She paused. She took a few deep breaths to ground herself instead of reacting.

She listened, resisting the urge to go into defense mode, and let her boss share his reasoning.

She acknowledged and validated his intentions before stating her concerns.

Then, instead of trying to convince him why he was wrong, she made him part of the solution:

"I see that you're trying to accelerate progress by testing new concepts—I appreciate the value behind these ideas. From where I stand, the team is focused on the initiative we agreed upon six weeks ago and is already two-thirds of the way there. How can we align on an approach that balances both innovation and building a strong foundation?"

This shifted the conversation from who’s right and who’s wrong to what’s possible given our constraints?

Her boss actually listened. The conversation became collaborative, and together, they co-created a realistic solution.

Why Managing Up Feels So Hard (And Why You’re Not Alone)

The truth is, most of us are never formally taught how to manage up.

According to a Harvard Business Review study, 91% of employees say managing up is a key leadership skill—but only 32% have received any training on how to do it.

So if you’ve ever felt frustrated or intimidated by managing up—you’re not alone.

But this skill is learnable.

And as leadership expert Marshall Goldsmith writes:

"What got you here won’t get you there."

To grow in your career, it’s not just about how well you manage your team—it’s about how well you influence with empathy.

How to Manage Up Without Losing Yourself

Managing up isn’t about being a “yes person,” but it’s also not about pushing back in frustration. It’s about leading with intention.

Here’s how you can do it:

Catch Yourself in the “Yes” Moment → Instead of committing on the spot, say:
"Let me think through what this means for our bottom line and the team and get back to you."

Regret Saying Yes? Go Back & Reset the Conversation → Offer a co-creative way forward. Example:
"After reflecting on our discussion, I’d love to revisit how we implement this. I want to make sure we balance speed with our goals for the year. Can we talk through a version that works best for both priorities?"

Shift from Proving to Partnering → Ask: "What’s the most important outcome for you here?" This question moves the conversation away from debating details and toward a shared goal.

Align Your Message with Their Priorities → Instead of saying "This disrupts our process," Rachel framed her response around what he cared about:
"I want to keep the momentum going while also ensuring we don’t slow down later due to instability. Here’s a way we can balance both."

Manage Up with Boundaries, Not Frustration → She set a boundary without making it personal by focusing on what would work. If your boss pushes for something unrealistic, try:
"I can absolutely work toward this goal. Given our current bandwidth, we’d need to adjust either the scope or timeline. How would you like to proceed?"

Here’s my invitation to you this week:

Notice where you’re saying yes when you mean no.
Notice where you’re convincing instead of co-creating.
Notice where you hold back when your fierce leadership is needed.

Because true leadership is about being brave and grounded in integrity—especially in challenging situations.

xo
Ramona

#Leadership #ManagingUp #CareerGrowth #ExecutivePresence