DGS 144: 3 Magic Questions To Close More Property Management Deals

When you’re competing for a sale or deal to close, to get a property management contract, or to get a referral partner, whatever it is you’re trying to do, you need to take things to a deeper level than your competition.

Property management growth expert and founder/CEO of DoorGrow, Jason Hull talks about three magic questions to ask during a sales conversation. When you ask these questions, potential clients will know that you care and want to help them, and you’re going to close more deals far more easily.

You’ll Learn…

[01:50] Pendulum Principle: There are two extremes when it comes to salespeople.

[02:21] Middle Ground: Find the middle to be much more effective and productive.

[04:16] Question #1: Why now, what’s changed? Client identifies, explains pain point.

[06:54] Question #2: What’s the biggest challenge with your rental property right now?

[08:42] Question #3: What result would you hope to see to know this was a success?

[11:02] Default vs. Creative Future Close: Depends on what challenges clients want.

[15:39] Primary Goal: Most people seek safety and certainty as their higher priority.


“You have to figure out where the middle is. The middle is the greatest place of power. It’s where you should be. It’s the point of truth.”

“Sales and deals happen at the speed of trust.”

“A business exists to solve a problem. If they don’t have a problem for you to solve, they don’t need you. There’s no point.”

“You are selling safety and certainty, not property management.”


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All right, we are live. Welcome, DoorGrow hackers, to the DoorGrowShow. If you are a property management entrepreneur that wants to add doors, make a difference, increase revenue, help others impact lives, you are interested in growing your business and life, and you are open to doing things a bit differently, then you are a DoorGrow hacker.

DoorGrow hackers love the opportunities, daily variety, unique challenges, and freedom that property management brings. Many in real estate think you’re crazy for doing it. You think they’re crazy for not because you realize that property management is the ultimate high-trust gateway to real estate deals, relationships, and residual income.

At DoorGrow, we are on a mission to transform property management business and their owners. We want to transform the industry, eliminate the BS, build awareness, change perception, expand the market, and help the best property management entrepreneurs win. I’m your host, property management growth expert, Jason Hull, the founder and CEO of DoorGrow. Now, let’s get into the show.

In today’s episode, we are going to be talking about three magic questions. I was doing my coaching call today, and yes it’s a Tuesday. It’s a day early because I’m going on vacation tomorrow. We did our group call a day early and one of my clients, he was talking about sales, and had some questions related to sales, and was having some challenges going into the conversation and being confident.

I talked about a principle called the Pendulum Principle which basically—a quick version of it, we could do a future episode on this maybe—if you recognize that there are two extremes. On one extreme you could be hyper-confident, maybe pushy as a salesperson, and a little bit too much. Then on the other side you could be a little bit not aggressive enough, too docile, not ask for the sale, and not try to close them that sort of thing.

You have to figure out where the middle is. The middle is the greatest place of power. It’s where you should be. It’s the point of truth. You need to figure out where you are and he was on the side of being a little bit too maybe nice, friendly, but not aggressive enough. He recognized it so I said, take the step into what feels like the complete opposite, being a little bit too aggressive, because if you aim for that, you’ll actually hit middle and you’ll be much more effective and productive.

We talked about how it doesn’t have to be mean, or you don’t have to be pushy or aggressive to go for the close. One of the things that he then got into were these three magic questions. I’m going to share these and we can talk about some other cool stuff related to sales maybe in a future episode. These are three magic questions that I find to be very powerful that I use during a sales conversation to take things a bit deeper.

If you want to beat out your competition, when you’re competing for a sale or a deal to close a client, to get a property management contract, to get a referral partner, whatever it is you’re trying to do, you need to be able to take things to a deeper level than your competition.

Things need to get a little bit more intimate, a little bit more relationship-oriented. There needs to be a little bit more connection because that’s where trust exists. Sales and deals happen at the speed of trust, I often say. Here are three questions that I use in order to deepen the conversation and take things to a more real or more raw level.

Question number one that you should ask that I brought up is, why now? If somebody comes to you and they’re like, hey, I’ve been looking to getting a property manager. I’ve had this property for many years, or hey, I got one of your mailers and it’s from a year or two ago. A really great question to ask in the sales process.

For example, if you’ve been listening to my podcast for many years now, and then you get on a sales conversation, you’re like, hey, now I’m interested. A great question to ask is, why now? Why now? What’s changed is kind of the additional part of that. Why now, what’s changed?

You’ve been looking at doing this for a while, or you’ve obviously had this property for a lengthy amount of time. What’s changed recently that’s caused you to be interested in property management? Or why now are you looking at getting a property manager? What’s changed? Help me understand that.

That’s where really deep stuff tends to come out. I’ve heard crazy why now responses from potential clients. I’ve heard things. I had one potential client say, I’m dying, I have this health issue, and I need to get this business healthy and ready quickly for other people to take ownership of it.

I’ve had people say that they just recently got divorced, so now they’re looking to make a move, change things, and improve the business. You never know what’s going to come out, but when you give them the opportunity to tell you, well, hey, something must have happened recently because things have changed. Why now?

Even just saying, why is now the time for you to do this? They shift into trying to explain, well, this is why it’s important to do this now. Just understanding that is going to reveal some pain. In sales, to close deals, you need to know what pain or discomfort they want to move away from and what pleasure they want to move towards? Where’s paradise for them?

If you know those two things, that’s really the crux of all you need to know in order to close the deal. Can I then help move them away from that pain? Can I help them move them towards that paradise that they want, that pleasure that they want? If I can do those two things, then all I have to do is future pace them and paint this roadmap for the future in which they can do that.

The next question I love to ask that is relevant to uncovering the pain is the biggest challenge. What is your biggest challenge in dealing with this rental property that you’re experiencing right now? I would usually ask, what is the biggest challenge you’re experiencing in your property management business right now?

Cool, I can help you with that. I’ve heard it before. I’ve dealt with hundreds and hundreds of property management businesses, gotten to see on the inside. It’s rare that I ever hear a problem that’s new. You probably have heard of all the same things in property management, all the similar problems. You’re probably not going to hear anything too new from an investor, so can you solve that problem? Yeah, you probably can. That’s why a business exists to solve a problem. If they don’t have a problem for you to solve, they don’t need you. There’s no point.

If I have somebody come to me and I say, well, what’s the biggest challenge in your business? And they say, well, honestly, our business is really great right now and I don’t have any problems. I say, cool. I’m totally open to that. I don’t know how I can help you then.

Then I might ask a follow-up question, well, why are we talking? How do you think I might be able to help you? Well, I was thinking maybe you could do this and help me do this. Okay, cool. Maybe I can, depending on what they say. You need to figure out what the challenge is, the pain, or the problem. What’s the biggest challenge you’re dealing with right now with this rental property with your tenant, or with your investment portfolio? That’s a really powerful question to ask.

The third question that can be incredibly powerful is what I call the crystal ball question. This is a question that is helpful for creating a potential future and future pacing a client that includes you. The crystal ball question usually looks something like this, usually, you’re going to use the one-year timeframe. Maybe you even use three or five years, depending.

The crystal ball question would look like this, hey, Mr. Owner, let me ask you a question. Just thinking about the future, if we were to work together a year from now, looking back on this moment, if you signed up with us a year from now looking back, what would have had to have happened for you to realize this was a great decision? Or what result would you be hoping to see to know that this was a success?

Then they start to use their imagination, which is powerful. They start to imagine a future. They’re imagining they signed up with you because you brought that into the conversation, and they’re imagining this potential future timeline a year from now that exists with some great result. There’s enough time to get to a result. They’re imagining that you were a contributor to that, and so they’re creating all of this in their head.

The brain’s super powerful. It’s an amazing supercomputer at doing this kind of thing, so they’re going to imagine this and then they’re going to tell you what this is, what this looks like. Which is basically saying—you’re just asking—how do we know that we can help you? What does winning look like if we were to work together? What does that look like?

They might say, we’re getting all of our rent collected, finally. We’ve got great tenants in place. The properties are all updated. Everything’s going great, blah, blah, blah, blah, blah. You can then say, that sounds awesome. I’m confident we can help you do that. Let me share some stories or examples that are similar to that we’ve already done so you can see this can be a reality for you. We’ve created this reality for other clients.

I usually call that close the default future close versus the creative future close. The default future, this is what you’re going to continue to get more of—more challenging tenants, more situations like you’ve dealt with. You mentioned these things that are challenging.

If you do not work with us, this is probably what will happen or maybe they’ve had bad experiences with another property manager because there’s a lot of sucky property managers out there. If they mentioned a bad experience when you’re asking these questions like, why now, and what’s your biggest challenge. You say, hey, well, you can continue to go down that path and choose another bad property manager and another bad one, or you could work with us, and here’s how this would work out differently.

First of all, we’re not going to do custom reports for you and we’re not going to let you micromanage us, so we’re not going to do things the way these other companies worked with you because you’re trying to run them from the back seat. We are going to be in control and in the driver’s seat in helping take care of this property, and that will allow you to trust us more. We’re going to take ownership of this and we’re going to be really good at this. This is what we do for clients that are in your situation.

They’re going to go, cool, and they’ll say, but I want this. You’ll say, we are not going to do that custom report for you and here’s why. We’re not going to do that for you and here’s why. Or there’s a fee for this, or there’s a fee for that.

Once you explain why they’re going to go, oh, this person is on top of stuff. They know what they’re doing. I can finally relinquish control and give up all that safety and certainty I’m trying to force to create in them. They’re going to just provide it for me. I can trust them, and I can lean into their frame that they’re going to do a great job and provide good service.

If you know why now, their biggest challenge, and the crystal ball, you’ve asked those questions, you’ve got those answers, if you know that, you should have a pretty deep conversation with them and really understand how you can best help them. If you connect that to other tactics I have like the golden bridge formula and other things to create trust beforehand, you ask really great qualifying questions, this should be very easy for you to create a relationship with these people, if you want it.

Anyway, that’s my tip for today is to ask those three big questions. Start asking, well, why now? Very easy to ask. Why are you doing this now? Why didn’t you do this a year ago? You’ve had this property for a while, why are you doing it now instead of later this year? Why is now the time to do this? Why now? You’ll get really interesting answers.

Ask what’s the biggest challenge that you’re dealing with right now because that’s going to help you understand their current immediate pain. Maybe there isn’t anything really major or really immediate, but help them that you could go deeper and say, well, what challenges have you dealt with that you don’t want to deal with in the future?

Then the future pacing question is a crystal ball question. Looking forward, if I had a crystal ball or you had it and you could see a year from now and you would sign up with us. We’re working together and we’ve done a really great job, what would that look like to you? Where would you be a year from now? What would your life look like? How would that be different with us having been a part of it?

Hopefully that’s helpful to all of you listening. I hope that you find those questions as useful as I’ve found them to be in the sales process. These were born just out of a real desire to care and take care of my clients, to really understand what they were going through, and figure out how can I help them, what do they need, and can I help them.

When you start to ask really good questions like that, they will know that you care, especially if you’re coming from a space of wanting to help them and you’re going to close more deals far more easily. Because a lot of companies are spending way too much time trying to sell property management and they don’t give a […] about property management. They don’t care about you or your business, they care about what they need, they care about their pain, their challenges, what they want, and outcomes they want.

If you can help them see that you can help them get out of the pain and get the things that they want, they’re going to want to work with you, they’re going to want to sign up with you, they’re going to feel safe with you, and trust you. Remember, their primary goal usually is safety and certainty. That’s more important than the four reasons, which I talked about in a previous episode of fulfillment, freedom, contribution, and support. They want safety and certainty.

After that, then they would like those things. But for most people, safety and certainty is a higher priority. That’s why they want and get a property manager. You are selling safety and certainty, not property management. Just make sure you get that.

That’s it. Hopefully this has been helpful, and until next time, to our mutual growth. I’m Jason Hull of DoorGrow. Reach out if you would like some help growing and scaling your property management business.

Quickly, just got off the phone with a past client, he was like, are people losing properties like doors due to sales right now? I said yes, everywhere, but not the clients that are in my mastermind, which you should join. The clients that are in my mastermind, one of our clients has added over 200 doors since joining in November. That would be impossible by spending money, doing advertising, doing SEO, doing pay per click, doing content marketing, doing social media marketing.

We would get you doing things that actually work that are far more effective and it costs him nothing. It actually took him less time to get those doors on than it would take if you spent a whole bunch of money on cold lead marketing because then those cold leads take more time than warm leads and you get less results.

If you would like some great results and you would like to start adding doors, scaling your business, getting out of the day-to-day operations, having more fulfillment, more freedom, more fun in your business, reach out. I love helping clients get that. That’s what I live for. That’s what I get to do every day. I love doing it, and we would love to help you grow your property management business. All right. Bye, everyone.

About Jason Hull

Jason's mission is "to inspire others to love true principles." This means he enjoys digging up gold nuggets of wisdom & sharing them with property managers to help them improve their business. He founded OpenPotion, DoorGrow, & GatherKudos.