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Questions to Ask Before Hiring a Real Estate Coach

Jul 25, 2026
 

The Questions to Ask Before You Hire a Real Estate Coach

By Jeff Levine, CEO, Levine Coaching Company

Hiring a coach might be the best decision you make for your real estate business. It might also be a waste of money and a year of your time. The difference usually comes down to whether you asked the right questions before you signed anything.

I have been on both sides of this. I have sold real estate, and I coach agents for a living. So let me save you some heartache and walk you through the questions I would want answered before I handed anyone my money and my trust.

Do you actively sell real estate?

Start here. Before anything else, ask the person straight out whether they are still in the business, actually listing, actually negotiating, actually sitting across the table from buyers and sellers.

This matters more than people realize. The market you are navigating today is not the market from five or ten years ago. Rates move, inventory shifts, buyers behave differently, and the scripts that worked in one cycle fall flat in the next. You want to hire someone who knows exactly what you are going through each and every day, not someone coaching from a highlight reel of how things used to be.

If a coach has not done a deal in years, ask yourself how they would know what is actually working right now.

How many times have you failed?

Here is one almost nobody asks, and it is the one that tells you the most.

Every real estate coach, and every salesperson for that matter, will happily tell you about all their successes. The closings, the awards, the production numbers, the story of taking a business from nothing to everything. That is the easy part. Anyone can hand you a highlight reel.

My question is different. How many times have you failed? And just as important, what did you do to move forward after that?

The answer tells you whether you are talking to someone who actually understands the grind, or just someone who is good at marketing. The failures are where the real lessons live. A coach who can walk you through what went wrong and how they climbed out of it is a coach who can help you when you hit the wall. And you will hit the wall. That is the job.

Be a little suspicious of anyone whose story has no scars in it.

Are you going to teach me how to run my business, or help me run mine?

This one is subtle, but it may be the most important of all.

There is a real difference between a coach who is going to teach you how to run their business, and a coach who is going to help you understand how you should run yours. Some coaches sell a system: one script, one funnel, one way of doing things, and your job is to fit yourself into it. That works for some people. For a lot of agents, it is like wearing someone else's shoes.

You are not a clone of your coach. Your market, your strengths, your personality, your goals, and the life you are trying to build are yours. A good coach helps you build a business that fits you and holds up when they are not in the room. Make sure the person across from you is interested in your business, not just in getting you to copy theirs.

Can you guarantee my success?

Ask it. And pay close attention to how they answer.

By the way, the answer to that question is no. Any coach who guarantees your success is either lying to you or does not understand the business. Nobody can promise you results, because a coach does not do the work for you. They do not make your calls, follow up with your leads, or show up on the days you would rather not.

The only person who can guarantee your success is you.

The right coach gives you the strategy, the accountability, the perspective, and the honest feedback to get there faster and with fewer scars than doing it alone. But the effort is always yours. If someone tells you otherwise, keep your checkbook closed.

The bottom line

A great coach is a force multiplier. The wrong one is an expensive detour. Ask whether they still sell. Ask what they have failed at. Ask whether they will help you build your business. And understand from day one that no one can guarantee your results but you.

If you are an agent weighing whether coaching is your next move, I would rather you ask me these questions than not ask them at all. That is exactly the kind of conversation I want to have.

Let's talk. If you are serious about growing your business and you want a coach who will be straight with you, book a call with me or send me a message. Come with your questions, and I will give you honest answers.

Jeff Levine, CEO, Levine Coaching Company

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