The Two Questions That Turn Every 1:1 Into Real Coaching Instead of Status Theater

Your calendar says “1:1,” but the last several have played out the same way: your direct report recites a project update while you nod along, and then you both move to the next agenda item. Nothing wrong gets said in a meeting like that. Nothing real gets drawn out of it either — and the difference between those two outcomes is entirely a question of what you asked, or didn’t.

C.H.E.W. with Me

New here? What is CHEW? — a 30-second practice that grows into a day woven with God’s love.

C – Clarity: The 1:1 That’s Actually Just a Status Report

The purpose sitting underneath your direct report’s update never comes up, because you never ask a question built to reach it. A calendar invite labeled “1:1” doesn’t automatically produce coaching or growth — it just produces two people in a room, unless one of them asks something different than “how’s it going.”

H – Hear: The Well Doesn’t Give Up Water on Its Own

“The purpose in a man’s heart is like deep water, but a man of understanding will draw it out.” (Proverbs 20:5)

Solomon pictures a person’s real purpose — their motives, their hopes, what’s actually driving them — as deep water sitting in a well. The Hebrew word behind “draw it out,” dalah, is the same word used elsewhere for drawing water with an actual bucket: it takes real effort and the right tool, not a passive stance beside the well hoping water surfaces on its own. “Understanding” here — tebunah — isn’t raw intelligence; it’s the discernment that comes from actively engaging, asking the question built to reach what’s underneath the surface report.

A leader who only collects status updates has never once lowered a bucket to find out what’s really underneath.

There’s a second layer here worth naming: the water doesn’t come up faster because the well is shallow. It’s deep by design — people don’t hand over their real purpose to just anyone who asks. The trust that makes someone willing to answer honestly is built over multiple 1:1s, not manufactured in a single clever question. The two questions below are a starting tool, not a trick that works once and stops working.

E – Exchange: The Bucket You Haven’t Been Lowering

Trade the passive 1:1 that waits for depth to surface on its own, for two specific questions built to draw it out on purpose, asked consistently enough that your team learns you actually mean it.

Because God’s love is patient enough to keep drawing out what’s underneath the surface of your heart instead of settling for the report on top, how does that change your next 1:1?

W – Walk: Ask the Two Questions — and Use the Tool

Before your next 1:1 this week, ask these two questions, in this order, and let the silence after each one run longer than feels comfortable.

PRACTICAL TOOL — The Two-Question 1:1 Script (this week’s featured Team tool):

1. Purpose: “What’s the real win you’re actually going for here — not the deliverable, the thing underneath it?”
2. Obstacle: “What’s getting in the way of that, that we haven’t said out loud yet?”
3. If they go quiet: “Take your time — I’d rather hear the real answer thirty seconds late than the safe one right now.”
4. Close: Name back what you heard in one sentence before moving to any action items.

Closing question: Which of your direct reports has never once been asked what’s actually underneath their update?