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Coaching

Before You Coach Anyone, Ask This One Question

By Phillip Gagnon · September 17, 2026 · 3 min read

I was talking with a managing broker last spring who was frustrated. She had a solid agent, decent numbers, but the agent seemed disengaged, going through the motions. The broker kept pushing harder on production goals. More calls, more open houses, more pipeline. The agent kept nodding and doing nothing. Sound familiar?

Here is what nobody had ever asked that agent: What does winning actually look like for you?

The Map You Are Using Might Not Be Theirs

We assume success in real estate means more closings, more GCI, a bigger team someday. And for some agents, absolutely, that is the scoreboard. But I have sat across from agents who define success as being home every night for dinner with their kids. Others want to fund a sabbatical in two years. Some want to replace a spouse's income so the family can breathe. That is not a lesser ambition. That is a deeply personal mission - and if you are coaching to your definition of success instead of theirs, you are pushing a rope.

The golden rule I keep coming back to: make the message about them, never about you. That rule does not stop at recruiting. It runs straight through every coaching conversation you will ever have.

How to Actually Have the Conversation

Block thirty minutes. No agenda beyond one question: If we are sitting here two years from now and you feel genuinely successful, what does that look like? Then be quiet. Let them talk. You are listening for the number behind the number - the reason that gives the goal its fuel. A $200,000 GCI target means nothing until you know it represents a paid-off parent's medical debt or a first investment property. When you find that, you have found the engine.

From there, work backward together. What does this year need to look like? This quarter? This month? Now you are building a plan that belongs to them, not a quota you handed down from a spreadsheet.

Write It Down and Keep the Promise

This is where most brokers drop the ball. The conversation happens once, it feels great, and then life takes over. I tell every broker I work with: date your agents. Regular one-on-ones, consistent check-ins, and - critically - circle back to what they told you mattered. Reference it by name. 'You told me in January that hitting this number meant your daughter's tuition was covered. How are we tracking?' That is not micromanaging. That is proof you were listening.

Retention is not a retention program. It is a hundred small moments where an agent feels seen, chosen, and supported toward their version of the finish line.

The Coaching Shift That Changes Everything

Stop coaching to production. Start coaching to purpose. When an agent's goal is anchored to something real in their life, the discipline follows naturally. In our data, intentional coaching lifts agent production around 30 percent - but only when the agent is bought in. And buy-in starts with being asked, not told.

Here is your do-this-now list:

1. Schedule a 'success definition' conversation with every agent on your roster this month. Not a performance review - a listening session.

2. Write down what each agent tells you. Keep it somewhere you will actually see it before your next one-on-one.

3. Build their 90-day plan around their why, not your production board. Let their goal drive the activity targets.

4. At every subsequent check-in, reference what they told you. Show them you remembered. That single habit builds more loyalty than any commission split ever will.

Until next time, keep nurturing those connections.

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