Written by Cari Borden

Let’s just say it: Coaching up can feel like trying to teach your cat to fetch, frustrating, risky, and highly likely to end in hissing.
But here’s the truth most people won’t tell you: Coaching up isn’t rebellion. It’s leadership.
The kind of leadership that requires a steel spine, EQ levels of a Jedi, and a strategy tighter than your boss’s Outlook calendar.
🎯 The Spicy Reality:
What do you do when:
- Your boss interrupts every meeting like it’s a TED Talk?
- They keep promoting “collaboration” but operate like a solo act?
- Or worse—they ask for feedback and then proceed to gaslight you out of your own opinion?
It’s tempting to stay silent. To keep the peace.
But silence only reinforces behavior, and guess who suffers? You. And everyone watching.
🔍 The Decision Framework: Should You Coach Up?
Before you go all “bold truth teller,” hit pause and run a quick internal scan:
Ask yourself:
- Is this a one-time offense or a pattern?
- Is this about personal preference—or professional impact?
- Do I feel safe saying something?
- Can I tie this feedback to outcomes, not egos?
💡 How to Say It Without Setting the Office on Fire
Use IRR + SMART to keep it bold, not reckless:
- Identify: “I noticed we’ve had a few moments lately where the team seems confused about direction.”
- Recognize: “It’s starting to slow us down and create tension.”
- Resolve: “Could we clarify priorities together and maybe define the top 3 focus areas as a team?”
That’s SMART: Specific, Measurable, Actionable, Respectful, and Tactful.
That’s leadership. Even when it’s upward.
🚩 Caution Zone: When NOT to Coach Up
- When it’s fueled by anger, not insight
- When you’re in a public setting
- When they’ve clearly shown feedback isn’t welcome
- When it puts your safety or job security at risk
Sometimes, the smartest thing you can do is document, observe, and outgrow the role.
🎁 Want to Know Your Style Before You Coach Theirs?
Take my free Leadership Style Quiz and see what kind of coach you really are.
Because knowing your approach can make or break how that conversation lands.
👉 Leadership Style Assessment
📣 Final Call to Action:
If you’re ready to stop tiptoeing and start leading—even when the org chart says you shouldn’t—
I’ve got your back.
Let’s build your coaching strategy together. Whether it’s prepping the convo or surviving the aftermath, I’m one click away.
🎯 Find me on Fiverr – Coaching Up Without the Burnout
✨ Like. Share. Lead boldly.
Leave a comment