Coaching Up: The Conversation Nobody Warned You About

Written by Cari Borden

You’re a great leader. You coach your team, you give feedback, you build trust. But what happens when the person who needs the coaching… is your boss?

Welcome to the tightrope act nobody trains you for, coaching up. It’s the silent skill set of emotionally intelligent professionals everywhere, and it might be the most critical leadership move you ever make.

🎭 Why This Matters:

You’ve seen the ripple effects of poor leadership from above
You know what it’s like to work around behaviors instead of addressing them
And you’re wondering: Is it even possible to coach someone who has more power than you?

Short answer: Yes.
Longer answer: Not without a strategy.

📚 What to Expect in This Series:

Over the next few posts, we’re breaking it down:

How to Coach Up Without Getting Shut Down – Knowing when, how, and if to say something
Managing Up: Coaching Without Overstepping (or Getting Fired) – Tact, timing, and surviving the conversation
When the Student Becomes the Coach: The Art of Coaching Up – Turning awkward into authentic and impactful

🔑 Final Thought:

Leadership is not a one-way street. The most effective teams lead in all directions, down, across, and yes, up. This series is for the brave few who are ready to lead, even when the conversation gets uncomfortable.

📣 Call to Action:

Think your boss could use a little coaching, but don’t want to start a corporate war? Stick around. Better yet, subscribe or reach out on Fiverr for a 1:1 strategy. Because coaching up shouldn’t feel like climbing Everest barefoot.