Selling the Impossible: How to Win Expired Listings and Become a Referral Machine

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It might be one of the best feelings you’ll ever have in real estate: the feeling you get after you sell a home that one, two, or several other agents couldn’t sell.

Jennifer Hastings, a top agent in Traverse City, Michigan, practically built her business around that feeling. After relocating to a new state, Jennifer took a unique approach to land clients from expired listings. Her first expired sale was a home that five other agents had failed to sell, and a different sale involved a home that eight others couldn’t sell.

In this week’s episode of The Walkthrough, Jennifer shares her system for reaching out to the homeowners of expired listings and explains how learning to sell “impossible” homes has turned her business into a referral machine. And don’t miss the story behind the sale of the home that failed to sell eight times — it involves a northern Michigan snowstorm and an open house with snowmobiles, hot chocolate fountains, and more!

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Links and Show Notes

Full Transcript

(SPEAKER: Matt McGee, Host)

Have you ever gone on a listing appointment and suddenly felt like you were in the middle of an episode of “Mission Impossible?”

Hello, top agent. The home you’re standing in is an eight-year-old ultra-modern in a neighborhood filled with 75-year-old Cape Cods. It’s beautiful, but it stands out like a sore thumb. The homeowner thinks the home is worth $100,000 more than the comps support and has rejected suggestions of new paint and carpeting. Your mission, should you choose to accept it, is to sell this home that four other real estate agents in your market have failed to sell.

Man: This recording will self-destruct in five seconds.

Matt: No, no, no. Nothing’s gonna self-destruct in five seconds. In fact, we’re gonna spend the next 30 to 35 minutes or so talking to an agent who has earned a reputation in her market as the agent who can sell homes that other agents couldn’t. Along the way, you’ll get some great ideas and advice for reaching out to expired listings, and you’ll hear how selling homes that others found impossible to sell helped turn her business into a referral machine.

This is “The Walkthrough.”


Hi, everyone. How are you? I am Tom Cruise. What, what? No? Still just Matt McGee here. I’m as disappointed as you that it’s not Tom Cruise. I’m the Editor of HomeLight’s Agent Resource Center. Welcome to “The Walkthrough.” This is the show where you’ll learn what’s working right now from the best real estate agents and industry experts in the country. At HomeLight, we believe in real estate agents and we’re on a journey to find out how great agents grow their business, stand out from the crowd, and become irreplaceable.

If you want to get involved in the show, you can leave a voicemail or send me a text. The number is 415-322-3328. You can send an email to walkthrough [at], or find me in our Facebook listener community. Just go to Facebook search HomeLight Walkthrough and it will come right up.

Last month, Jeanne Dominguez used that voicemail line I just mentioned to send in this question.

Jeanne: I recently moved to a new market, moved across the country, and my question is how can I grow my database when we’re faced with COVID-19? I’m in California and we are not allowed to have open houses, no door knocking, no public events. So I’m trying to grow my database in a new market. It’s been very difficult. So I’m wondering if any of your listeners or experts that you have on have suggestions for a Realtor to grow their database?

Matt: Jeanne, thank you so much. I think this episode might help because my guest today was faced with that same dilemma, minus the COVID-19, about five years ago.

Jennifer Hastings had spent years flipping homes in Maryland, then moved to Traverse City, Michigan, and decided to get her real estate license. She didn’t have a big database, didn’t have a sphere of influence to help her get started. Despite that, Jennifer did $5 million in volume her first year in a market where the median price was about $200K. She says between 50% and 75% of that came from expireds.

Today, Jennifer is the managing broker of Key Realty in Traverse City. She’s also team leader of the Blue Lakes Real Estate Group. Thanks to her ability to sell homes that other agents couldn’t sell, her business is now almost 100% referrals. How did that happen? Well, when three, five, or even eight other agents can’t sell a house and then you sell it, you make friends and clients for life. And they are constantly telling people about Jennifer and her team.

One more thing you should know about Jennifer, she has a competitive spirit. Before getting into real estate, Jennifer owned a Tae Kwon Do studio and trained athletes that made our national and Olympic teams.

As you listen today, you’ll hear Jennifer talk about her system for reaching out to expired listings, how selling these impossible homes has helped her business become almost all referral-based now, and the amazing story behind how she sold one home that eight other agents failed to sell. It involves a snowstorm, snowmobiles, hot chocolate fountains, and more. Incredible story.

All of this happened out of necessity. Jennifer didn’t know many people when she got to Traverse City so she decided to reach out to the owners of expired listings and that’s where our conversation begins.


Matt: You earned a reputation as an agent who can sell difficult homes, homes that other agents have failed to sell. How did that happen?

Jennifer: It happened by taking a very concerted effort to approach expired listings. I decided that it was an area that needed attention. At the time that I was looking into it, we had a lot of expired listings and I enjoyed trying to problem solve and figure out why they expired, what went wrong, and how myself and my team could turn it around and get the home sold or the property sold for the client.

Matt: And was this right at the very beginning of your real estate career?

Jennifer: I would say it was very close. I moved to Traverse City in 2012. I did not have a sphere of influence already in place. I was not a local, I had not grown up — we’re a very small, tight-knit community so without a sphere of influence, I thought I was gonna be in trouble, and needed to figure out a way to begin to create business, and expireds interested me. I thought it was exciting.

Matt: What did you do, what was like the first couple steps when you say, “All right, I’m going to go down this path”?

Jennifer: Lucky for me, I had a mentor who talked me into getting my license when I arrived in Traverse City because of my passion for real estate and my previous background in doing house flipping. So I spent a lot of time talking with him about how expireds were typically approached. And a lot of the times I found that agents would immediately pick up the telephone and call that person the day that their house expired. And I thought, well, that’s not too cool because you know, usually they’re angry, they’re frustrated and they’re not feeling really positive about Realtors at the moment. You just failed them. You didn’t sell the property and they’re probably a little irritated.

So I decided to take a little bit of a different approach and I’ve never made a telephone call to anybody cold. For me, it’s not my style. It’s not my comfort, never to do cold calling. But what I did do was I put together a letter and a very sincere letter that basically after I analyzed the property and in my mind kind of had an idea of what went wrong, I kind of tried to present a letter that gave them a solution and gave them some hope.

And, you know, it took a little while for that message to work and I kept kind of tweaking it and tweaking it and then the next thing I knew, my phone started ringing and the people would ask me questions, we’d have great conversations. And maybe not even great conversations, but at least I was having conversations. And then it just started happening. I’d go out, I see the property, we’d talk about it and list it and sell it.

Matt: I think you’re absolutely right, by the way. I think probably calling the day that the home expires, that’s not the right time to reach out to the homeowner. How long do you wait? Are you waiting a couple of days, a couple of weeks before you send your letter?

Jennifer: I found to let people just kind of sit for about a week. That was my initial timeframe that I would start approaching, but I’ve also gone back and I have found properties that, you know, expired nine months ago. I would reach out to them and find out surprisingly like, well, nobody reached out to them and at that point, they were extremely grateful to have a conversation with me.

But I think to allow somebody, you know, a week to try to figure out, you know, this is their home. They feel like, you know, “What happened, what’s wrong with our house? We love it. Why doesn’t everybody else love it?” And it’s very personal. So when you start calling them and you start telling them how great you are and what’s wrong with their house and why it doesn’t sell, they’re not really ready to hear that.

Matt: Tell me what is in this letter? What are you saying? Are we talking soft touch? Are we talking hard sell? What’s the approach?

Jennifer: Oh, it’s really a very soft touch. And really, again, I don’t just blindly send out the letter. I spend a lot of time looking at the property. Not just on the MLS, but I’ll go find it in Zillow or and really look at what were the deficiencies with the listing. Yep, granted, sometimes it’s price. A lot of times, it’s price, but sometimes it’s just really poor pictures. A lot of the times it’s a home that never got any visuals done that made you think that you would even want to see the property. No video, no drone video. And our team is really big with using drone video, interior, exterior, and allowing people to just kind of sit back and look at their computers and take a tour of this home. If it’s a really complicated property, maybe a lakefront property, then we create what are called lifestyle videos.

Let me go backwards again and say, so I really study and try to figure out why it failed to sell the first time. Did it hit the market that it should be hitting? Did it hit the consumer or did it miss the right consumers? And so I will use a soft touch letter with some of the areas that I thought were deficient and use the example of why I didn’t bring one of my clients to see it, and that helps them understand.

Matt: I think that’s a brilliant approach, especially to come at it with that, “All right, if I had a buyer, this is why I would not have come to see your house, why I would not have written an offer.” Does it take just one letter to these homeowners? Do you follow up after that?

Jennifer: I do. It’s taken me up to three well-crafted letters to get a phone call. It’s exciting when you send out a batch, and you get a couple of phone calls after that first one, but I have sent as many as three and I spread them out. Again, giving the person an opportunity to get online and find out who you are and make sure that you’re valid and legitimate, and that you have some sort of positive credibility behind you and giving them an opportunity to just kind of sit on the letter and maybe at this time they’re getting calls from other people.

And that’s another thing that I do. I highly recommend that they re-interview as many agents as possible to find that person that really understands their property. So I don’t just say, you know, “Hey, use us, we can do this for you.”

Matt: Right. Yeah, I love that. I think that’s fantastic. And you just mentioned the idea that once you send this letter, the homeowner’s gonna do some research on you. And you say specifically on your website that, you know, your team has a reputation for selling difficult homes. I’m gonna ask you more about that a little later in the conversation, but first, let me just make sure that I’m unpacking this outreach that you do to the homeowner of the expired listing. What is the call to action in the letter? Are you saying, “Give us a call if you want more information or let’s set up an appointment”?

Jennifer: It’s more along the lines of, “I would love to talk to you more in detail about this. We would love to help you … solution. If you’re still considering selling it, we would love the opportunity to toss our hat in the ring and meet with you and describe how we do listings.” Really big on making sure that people understand that I don’t consider our team, we’re not listing agents because anybody can list. We are selling agents. So if we’re gonna list it, we’re gonna sell it.

And if I don’t think that we can get it sold at the right price because, you know, you still find those people who are like, “No, my house is definitely worth this amount,” then I’m gonna wish them luck and let them figure it out. I’m not just gonna take the listing.

Matt: You mentioned a few moments ago, too, you mentioned that sometimes the home wasn’t marketed to the right buyer. Tell me what you mean by that.

Jennifer: If you really look at expired listings, they tell a story and they’re usually complicated properties. Particularly here in Grand Traverse County, Leelanau, up North Michigan, they’re complicated. There’s something that’s off that doesn’t attract a person looking for a cookie-cutter home, or even a person looking for a straightforward lakefront home. You have to find what that niche is.

One of the properties that we recently sold, people thought it was a commune. Well, it wasn’t a commune, but it was an intentional community and it’s very rare that you find a home in an intentional community like this. So there are only eight homeowners in this community called Telford Farms. They each have their own individual home, but collectively they shared in 80 acres. Thirty of which were vineyards and another 10 acres were preserved by the conservation.

So when it already had the reputation of being a commune, like who really wants that? But marketing it and letting people understand that it was an intentional community where everybody takes ownership for all of the property with the exception of your personal home, it was a wonderful idea.

I mean, they have amazing gardens and they have barns and pottery barns and farm animals that everybody can choose to collectively be involved with. So once we figured out who the audience was, and during COVID, trust me, there was quite an audience. People in large cities were looking for just that, to get away and kind of figure out how they can stay away from the big cities and live safely.

So it was about creating a really positive lifestyle video of what this community was all about. We actually had the owners do the video for us. They were very well-spoken, great to watch on film and they did a beautiful presentation for us. So the house sold very easily.

Matt: Let’s go back to the beginning. Tell me about your success. What percent of your business came from expireds in the first year and what has it been since then?

Jennifer: In the beginning, at least 50% of my business, maybe higher, came from expired listings. And then what happened was those people started to tell their friends to contact me. “They were able to sell my home. Nobody else could do it. You’ve got to use them,” and that’s how the referrals started. Basically 100% referral business [now].

Matt: Tell me about the very first expired listing that you had. I guess, what was the aha moment that, “This is something that works, and this is something I want to keep doing”?

Jennifer: Well, the aha moment is when the phone rings after you’ve sent out letters, and the fact that you can then get your foot in the door and have an opportunity to then start talking about what it is you can do. And, you know, there were some properties that I’ve gone to, and in conversations, the owner has said, you know, “Look, I’m not budging on price.” And if I honestly don’t believe that my team and I can get it done, I’m not going to take it.

And there have been times where I’ve stood up. I’ve said, “Thank you for your time. I really appreciate it. We can’t do it.” And then they’ve always asked me to sit back down and it’s worked out.

So my aha moment, my very first one, I want to say that my very first one was a very unique home in a very small village called Brethren, Michigan. I had not even ever heard of it, and way, way, way out in a very rural area. And they had a beautiful home that they had purchased. It was on 10 acres, had an indoor swimming pool. And the family was using it, but they were also doing a short-term rental there. Many people had tried to sell it. So I finally met with them, looked at the property. Actually, we never met, it was all done long-distance. Zoom before zooming was cool.

So I went out and I looked at the property and it was great. I mean, there were some issues with the pool that needed to have some maintenance done to it. There were things that I told them needed to change in order to get the listing ready and they thoroughly believed in the process. So we were able to create, again, a very cool video showing how the house could be used.

There was, you know, snowmobile trails right around the back of the property. There were decks everywhere. So we just created a really cool video, sent it out, got the price right. And it was a small price reduction, but it was enough. And, you know, it was an investor’s dream, to be honest with you.

It doesn’t mean that we didn’t send out marketing to the everyday person looking maybe to live way out in the wilderness and be off the grid a little bit who would enjoy this for their regular home, but that was secondary marketing that we did. So I think it was on the market maybe 15 days and we just got a rush of people looking at it and got it under contract.

Matt: How many other agents, or how many other times has it been listed?

Jennifer: That one was probably about five other agents over the course of about three years. Our biggest was eight agents who couldn’t sell a particular property.

Matt: Is that the one that you got the listing and you’re having the open house and there’s this big, huge snowstorm?

Jennifer: That’s it.

Matt: Tell that story. That’s a really great story.

Jennifer: Well, first of all, this client was absolutely amazing. She received one of my letters. She told me that she sat on it for an additional five days thinking about it because she thought, you know, “This is bull. Why does she think she can sell it? Eight people have tried.” She had also never heard of us.

And I received a phone call one Sunday morning and very gruff voice and she was no-nonsense. Told me that she had had enough of Realtors, but she got my letter and was interested to know what I was going to do that would be so different. And I said, “Well, when can I see the property?” And she said, “When do you want to see it?” And I said, “Right now.” So with that, she was blown away that I would get in the car and went ahead over immediately. And I did.

And there was this very tough woman. We’re now very good friends. We laugh about it all the time because she was just so determined to be angry. And so we sat down at the kitchen table after looking at her property. Her property had 30 acres and in a beautiful county and it overlooked the bay. And it had a small ranch home on it.

And initially, when it was listed, somebody told her that it was in excess of a million dollars. It was really an overinflated price. And I think the reason they thought it may have been worth that much because they thought that the land could be sectioned off by a builder and then homes built on that 30 acres. But in fact, that wasn’t the case. The county had assessed it to be an agricultural property so it was limited on how it could be broken up.

So it failed, it failed, it failed, it failed, it failed. And then I’m the one that had to come to her and bring her the really bad news. And this is the one that was hundreds of thousand dollars less and explaining to her why. And she somehow miraculously agreed that somebody had finally gotten it right and she was willing to go with that.

So we immediately got everything together, got the videos, got the photos, moved very quickly on it, prepared for an open house. And then the night before the open house, we had well over a foot of snow. And, you know, we were all in a panic and I called some of my best lenders and title companies and said, “Here’s my situation. What can you guys do to help?”

I happened to have a very dear friend who is a great chef here in town. Called him last minute and we basically just blasted all social media, telling everybody, “Come with your cross country skis, we’re going to have snowmobile tours of the 30 acres, bring snowshoes.” My chef friend, Eric Natolo [SP], he got out there, put up hot chocolate fountains, made these little grab and go cake pops. We had hot apple cider, we had fire pits all along the property. We had the house opened up and people could tour it and it was amazing. It was one of the most fun open houses I have ever done and it pulled the most people and we received three full-price offers. It was a blast.

Matt: Again, what we’ve talked about earlier with you sell this home and now you have a friend for life, you have a referral source for life, and you just knocked their socks off with this experience.

Jennifer: This particular client, like I said, we are friends, very close today. I then sold her her next home and she introduced me to three of her friends that we have now closed transactions for.

Matt: A lot of agents prefer, you know, the smooth, easy deals, the homes that are easy to sell, homes that appeal to a wide variety of buyers. What is it about these kinds of homes, the difficult transaction that gets you fired up?

Jennifer: I think you just said it, it’s the difficult transaction. It’s fun and I love to put up anybody’s home, but you know, particularly right now, if there is a home out there that is under $500,000, it’s gonna sell in a matter of minutes and you don’t even have the opportunity to get super creative.

We listed up two houses in two different communities two Thursdays ago. We didn’t allow any showings because we didn’t want to complicate our clients’ lives because they’re working from home. So we held off and had open house on Sunday…excuse me, Saturday. No exaggeration, about 20 people through these open houses. And of course, you know, everybody’s got to come in masked and gloved and two people through at a time, they go out the back door, we spray, the next two come in. So there were little lines.

And, you know, they each received about nine offers and I thought, “Wow, that’s done.” And it was the location and it was the price and it was wonderful. These are great clients. And don’t misunderstand me, we love every type of business that we can do, but it doesn’t really challenge you. And, you know, right now putting up a home in the market, anybody can put a sign in the yard and if it’s under a certain price point, it’s gonna sell.

Matt: I mentioned early in the show that you have a background in training Olympic athletes. Is there a sort of a competitive aspect to this as well that you enjoy these homes?

Jennifer: Well, I think so. I try not to look at certainly my peers as competitors. I know a lot of people do, but I look at it more as, you know, we’re all out here working together and we need each other, but I am very competitive. I grew up playing sports and training athletes certainly makes you competitive. You’re a coach. You’re competitive. And so, yeah, I think my competitive spirit certainly ignites when I have the opportunity to do an expired listing particularly when it’s been done by a couple of different Realtors and unsuccessfully done.

Matt: You even use this in your marketing and we kind of hinted at this a little earlier in the conversation, if somebody visits your website, you go right there and it says, and I’m quoting right now, “Our team quickly garnered a phenomenal reputation for being able to sell the impossible.” Do you ever worry that you are inviting trouble with that? Like you’re like inviting difficult homes and difficult clients into your business?

Jennifer: No, I really don’t. I don’t really think that there is such a person as a difficult client. I think it’s inability to communicate well with these people. And I think the communication is an art and it’s something that a lot of Realtors don’t spend a lot of time with. Because I read all the time where people were complaining about difficult clients, whether they’re buyers or they are sellers and I think it’s because you didn’t set the groundwork. You didn’t lay out the expectations.

Not only does the seller have expectations of me and my team, but I have expectations of my seller. If we’re gonna have your home cleaned and ready to go for showings, my expectations are that you’re going to keep it that way and I need you to keep it that way. If it’s in the middle of winter, my expectations are you will continue to care for your property by making sure the driveway is shoveled and that people can safely enter your home.

So I think it’s all about how you communicate with people and that kind of sets the tone. So when I get called, you know, I told her about the one experience where she was very gruff and she was no joke and it was plain that she had been at her wit’s end with Realtors and didn’t know where to turn. And rightfully so. I mean, if eight people tried to sell your home, I think you’d be really frustrated too.

And again, there was nothing wrong with the home, there was nothing really wrong with the property. She was just failed by the industry. People didn’t really look into her property to understand what could and couldn’t be done with the vacant land. They didn’t pay attention to what the township zonings were and they let her down that way. They failed, she didn’t, and she had every right to be angry.

But it was the communication that we had and it took some time to build her trust. About a week. And when the offers started coming and they made sense to her, the trust was gained and therefore she introduced me to her friends who I have now done business with. So communication is super important.

Matt: If we have listeners that are thinking, “Maybe I’ll give expired listings a try and see if I can find some homes that other agents couldn’t sell,” what would be the advice that you would give to them?

Jennifer: Study the property, understand it, figure out why you think it didn’t sell. Craft a letter that is sincere, that is honest and that is unique to that person. Don’t send out bulk mails where it’s the same letter because it’s not the same house. Let them see that you’ve spent some time looking at it. Make the letter personal to their home.

The other little benefit I can tell you is hand-write your envelopes. If you’re gonna print out your letters, that’s fine if you don’t want to handwrite a letter. Sometimes I’ll just handwrite a letter or a little note. It’s a card and like here’s a quick synopsis of things, but if you’re going to print out a letter, then handwrite the envelope. People are more inclined to open up a handwritten one than a typed one because when they see your logo and they see it’s a real estate agency or a brokerage or a Realtor connecting with them, it’s gonna end up in the waste bin. The more personal you can make it, the better.

Don’t reach out and just start telling them everything that was done wrong. Talk to them about, you know, how cool their house is and find the positive things in the house and then be ready to offer solutions, real solutions.

(Speaker: Matt McGee, Host)

Jennifer had one more tip she wanted to pass along. If you’re going to contact expireds, crosscheck what you see in your MLS with your local tax records. She says sometimes a home might be listed as expired in the MLS but if you look at the tax records, it’s actually been sold. So that’s a great tip there. It’s also a perfect segue into our takeaways segment. So here’s what stood out to me from today’s conversation.

Takeaway number one, Jennifer went after expired listings out of necessity. She didn’t have any contacts in Traverse City when she got her license so expireds made sense because, hey, these were homeowners that already tried to sell and probably would want to try again.

Takeaway number two, rather than cold calling, Jennifer sent out personal letters to the homeowners. Not a hard sales pitch, but more soft touch. She analyzes the home, figures out what were the problems with how it was listed and marketed, and then offers her solutions in the letter.

Takeaway number three, don’t do all of this as soon as the listing expires. The homeowner probably isn’t very fond of real estate agents at that moment. Jennifer would wait at least a week, she says, before sending out that letter. And she also says be patient because sometimes it took as many as three letters before she’d hear back from the homeowner.

Takeaway number four, when you’re selling difficult properties, or I mean any property really, but especially homes that have already failed to sell, think about who the ideal audience is for that home, who might want to buy this house and then build your marketing around that audience.

Takeaway number five, sometimes with homes like this, you have to pull out all the stops. Think about that open house Jennifer did after more than a foot of snow fell the night before. They did snowmobile tours, hot chocolate fountains, fire pits, and more and she got the house sold that day.

Great stuff. Thank you so much, Jennifer.

Listeners, if you have questions or feedback, you can leave a voicemail or send me a text. It’s 415-322-3328. You can send an email to walkthrough [at], or just find me in our Facebook listener community. Go to Facebook, search HomeLight Walkthrough and it will come right up. Join the other…it’s almost 600 listeners in that group right now.

That’s all for this week. Thanks so much to Jennifer Hastings for joining me. Thanks to Jeanne Dominguez for the great question that she sent via voicemail and thank you for listening. My name is Matt McGee, and this is “The Walkthrough.” At HomeLight, we believe in real estate agents. We’re on a journey to find out how great agents grow their business, stand out from the crowd, and become irreplaceable.

Next week is our final show of 2020 so don’t miss that one. In the meantime, go out and safely sell some homes. I’ll talk to you again next week, everyone. Bye-bye.

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