Questions to Ask Before Hiring a Real Estate Coach

By Jeff Levine, CEO, Levine Coaching Company. Published July 25, 2026. Updated September 13, 2026.

There are 1,438,569 Realtors in this country as of June 2026. The median one closed 9 sides last year and made $59,200 before expenses, against a median business expense line of $9,530. If you have been in the business two years or less, the median is 2 sides and $8,000. Sixteen years in, the median is $88,500.

That spread is why the coaching business exists. It is also why you need to be careful about who you hand your money to.

I bring nearly 30 years of real estate industry experience. More than ten thousand transactions, over three billion dollars in closed volume. I have hired coaches, I have been a coach, and I have watched a lot of agents pay for something that did nothing for them. The difference almost always comes down to what they asked before they signed.

Here are the five questions. Ask them out loud, on a call, and listen to how fast the answer comes.

1. Do you actively sell real estate?

Not did you. Do you.

The market you are working today is not the market from five years ago and it is definitely not the market from 2021. In Florida right now we are sitting around 4.7 months of supply, the statewide median price is near $425,000, and homes are taking a median of about 84 days to sell. In Palm Beach, Broward and Miami Dade it is past 90. Insurance runs north of $8,000 a year on average. Condo buildings three stories and up have to fully fund reserves as of January 1, 2026, and that has pushed special assessments into five figures on a lot of older coastal product.

A coach who stopped writing contracts in 2019 has never had to explain a $40,000 assessment to a buyer. They will teach you scripts that worked in a market where you could list anything and have six offers by Sunday.

Here is a number worth sitting with. The 2025 ICF Global Coaching Study counted 122,974 professional coaches worldwide, and the average one earns $49,283 a year. That is less than the median Realtor. Before you pay somebody to teach you how to make money in this business, find out whether they are currently making it.

A good answer sounds like: a current listing, a current problem, and a deal they are working on this week.

2. How many times have you failed?

Almost nobody asks this one, and it is the most useful question on the list.

Anyone can put a highlight reel on a website. What you want to know is whether this person has been broke, whether they have lost a team, whether they have had a year where the phone did not ring. The lessons worth paying for come out of those years, not out of the record ones.

So ask it directly. How many times have you failed, and what did you do to move forward after that?

If a coach cannot name a specific failure, one of two things is true. Either they have not been in long enough, or they are not going to be honest with you when you fail. Neither one helps you. Be a little suspicious of anyone whose story has no scars in it.

A good answer sounds like: a specific year, a specific number, and what they changed because of it.

3. Are you teaching me your business model or helping me build mine?

This is where most coaching goes wrong.

Plenty of coaches sell one system. It is usually the system that worked for them, in their market, with their personality, in whatever year it worked. Then they hand it to a thousand agents and tell them to run it. Some of those agents happen to match the model and do great. The rest quietly quit and assume they are the problem.

You are not the problem. The fit is. An agent who does well on the phone and an agent who does well face to face need different businesses. A listing agent in Boca and a buyer's agent in Fort Lauderdale need different businesses. Somebody with 400 past clients in a database and somebody with 12 need completely different plans for the next ninety days.

The NAR data backs this up. Agents with real tenure pull 49 percent of their business from repeat clients and another 32 percent from referrals. Agents in their first two years get essentially none from either. Those are two different businesses that happen to share a license.

A good answer sounds like: questions about you. Your numbers, your market, your strengths, what you actually like doing. If the first call is all them talking, you already have your answer.

4. Can you guarantee my success?

The right answer is no.

If somebody guarantees you closings, walk. A coach does not do the work for you. I cannot make your calls, I cannot sit in your listing appointments, and I cannot make you open your CRM on a Tuesday morning when you do not feel like it.

Coaching is a force multiplier. It makes the work you are already doing produce more, and it stops you from spending another year on things that were never going to pay. Multiply zero effort by anything and you still have zero.

What a coach can reasonably commit to is process. Showing up. Telling you the truth. Holding a number in front of you every week whether you want to see it or not.

A good answer sounds like: no, followed by exactly what they will hold you to.

5. What does it cost, and what am I actually getting for it?

You should not have to sit through a forty five minute discovery call to find out a price. If somebody will not give you the number until they have warmed you up, that tells you how the rest of the relationship is going to go.

Ask for the number, the length of the commitment, how often you actually talk to the person whose name is on the door, and whether you are getting that person or an employee. All four matter. A cheap program where you never speak to the coach is not cheap, it is just small.

I publish my prices for that reason. They are all here: what real estate coaching costs and why I only take twenty clients.

A good answer sounds like: a number, said immediately, without a flinch.

The short version

• Do you actively sell real estate? Looking for a current deal, not a resume.
• How many times have you failed? Looking for a specific year and what changed.
• Whose business model is this? Looking for questions about you.
• Can you guarantee results? Looking for no, plus what they will hold you to.
• What does it cost? Looking for a straight number.

Ask all five. A coach worth hiring will like that you asked.

Let's talk

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

Jeff Levine is a Broker Associate and Team Leader of Lux Places Group at RE/MAX Services in Boca Raton, Florida, and the Founder and CEO of Levine Coaching Company. He brings nearly 30 years of real estate industry experience, more than ten thousand transactions and over three billion dollars in closed volume. He is the 2026 Vice President and 2027 President Elect of Florida Realtors, a Past President of Broward, Palm Beaches & St. Lucie Realtors, a licensed Florida real estate instructor, and holds the CIPS, ABR, CRS, SRES and PSA designations.

Sources: National Association of Realtors 2026 Member Profile; 2025 ICF Global Coaching Study; Florida Realtors market data.

Published by Levine Coaching Company.