Coaching UP

It’s a common misconception that coaching is a "downward-only" skill—something leaders do for their direct reports to improve performance. But in reality, coaching is a communication framework, not a hierarchy.

When you apply coaching principles to your supervisor, you aren't "bossing the boss." Instead, you are using high-level inquiry and deep listening to clarify expectations, align priorities, and influence the environment you work in.

Here are some thoughts to help you master the art of "Coaching Up."

Why "Coaching Up" Works

Managing up through coaching isn’t about correcting your boss; it’s about creating clarity. Supervisors are often stretched thin, dealing with their own pressures and "blind spots." By using coaching questions, you help them distill their own thoughts, which in turn gives you the autonomy and direction you need to succeed.

Three Coaching Tools for “Coaching Up”

To coach your supervisor effectively, you need to shift from reporting to inquiring. Here are three ways to do it:

1. The "Priority Filter" (Clarifying Questions)

Instead of simply saying "yes" to every new request, use coaching questions to help your supervisor weigh the trade-offs. This prevents burnout and ensures alignment.

• The Shift: Move from "I’ll get it done" to "How does this new project rank against my other work in terms of our current goals?"

2. The "Perspective Shift" (Reflective Listening)

Often, a supervisor's frustration is rooted in a lack of information or a different perspective. Reflecting their concerns back to them helps them feel heard and allows you to bridge the gap.

• The Shift: "It sounds like your main concern with the project is the timeline. If we were to adjust the launch date by one week, what impact would that have on your stakeholders?"

3. The "Resource Unlock" (Empowerment Questions)

If you’re stuck, don’t just ask for a solution. Coach your boss to provide the support you need to solve it yourself.

• The Shift: Move from "What should I do?" to "What would 'great' look like for this deliverable, and what's one thing you can do to help me clear the current roadblock?"

The Golden Rule: Stay Curious, Not Critical

The secret to coaching up is intent. If your supervisor feels interrogated, they will shut down. If they feel supported and understood, they will lean in.

The Goal: You aren't trying to change who they are; you are trying to change the quality of the conversation between you.

By using coaching as a bridge, you transform the "boss-subordinate" dynamic into a collaborative partnership that benefits the entire organization.

Nemawashi & Coaching UP

"The Root Work: Using Nemawashi to Prepare and Persuade."

In gardening, Nemawashi literally means "rounding the roots"—the process of preparing a tree's root system for transplanting so it doesn’t suffer shock. In leadership, it’s the quiet, informal process of laying the groundwork for a new idea or change before the formal discussions even begin.

If you walk into a meeting and try to coach your boss toward a new idea without Nemawashi, it might feel like an ambush. But if you use Nemawashi to soften the soil, your coaching questions feel like a shared exploration. A supervisor’s instinct when presented with a sudden challenge is to be directive (the opposite of coaching). Nemawashi helps eliminate the "shock" of a new perspective.

Here are some steps to incorporate Nemawashi with the art of “Coaching Up”:

1. Plant the Seed: Casually mention the problem (not your solution yet) in passing.

2. Stakeholder Sweep: Talk with other leaders and team members to uncover their concerns about the problem. 

3. Upward Coaching: Now that the ground is soft, you use coaching questions to lead the boss to "discover" the value of your recommendation.

Here’s how this looks when it all comes together: 

Want leadership & coaching tips?!

Check out our YouTube channel, and while you’re there, be sure to subscribe!

“To Lead the People, Walk Behind Them” – Lao Tzu

I think this quote sums up the philosophy of today’s newsletter nicely.

You are the one doing the "root work" and asking the questions from behind the scenes to ensure the person at the front (your boss) succeeds—and by extension, so do you!

Reflection

This week, try replacing one "status update" in your 1-on-1 with a coaching question aimed at your supervisor. Notice how the energy of the room shifts when you stop seeking answers and start facilitating them.

Want to Enhance Your Coaching Skills?

Click Here to

BEGIN YOUR COACHING JOURNEY!

For a limited time, I’m offering a complimentary lesson -

Check it out below!

Making the World Better by Building Better Leaders

[email protected]

(850) 287-8879