The Listing Agent: Friend or Foe?


10 minute read

April 12, 2023

I sold a house last weekend which I can only describe as a “feel-good deal.”

When I told this to a colleague on Monday, he said, “All deals are ‘feel-good deals,’ David.  A deal is the point.”

I suppose that’s one way of looking at it.  All offers and subsequent negotiations that end with a completed transaction should be viewed favourably, since a “deal” is the end goal.

But what I meant by “feel-good” in this regard was that we bought an exceptional house for a great price, after losing out on the house the first time around, after almost losing out a second time, and by beating out another buyer who was represented by an agent that went about the process all wrong.

For those that think real estate is going to be bought and sold by A.I. one day, I challenge you to read the following story and tell me that relationships in this business aren’t what get deals done.

Relationships can get deals done but a lack of a relationship (and in this case, a buyer and buyer agent who rub the seller and listing agent the wrong way) can ensure deals aren’t consummated.

Clients of mine were looking for a North Toronto home and they had some very specific criteria.

Having purchased a home several years ago that they outgrew rather quickly, they wanted to ensure that this house had enough space for today, tomorrow, and for well, well down the line.

There was a certain aesthetic they were going for, as well as layout.  There were several boxes to check in their search, but nothing on their list was unreasonable.

All told, they were very savvy buyers who knew what they wanted but didn’t know when or where they would find it.

They were open to several areas and that usually helps provide more options, but at this particular time, there just weren’t any “homeruns” out there.

I mean, there was one, in my mind.  But it was sold conditionally.

This house came onto the market and promptly sold right away.  Sold conditionally, but sold nonetheless.

We had viewed a few homes in a multitude of areas but nothing really “fit.”

It was a classic case of The Three Little Bears.

One house was too small.

The next house was too big.

The next house was too renovated.

The next house wasn’t renovated enough.

I found myself saying, “Don’t worry, guys.  There will be a lot more inventory after Easter, and we still have two months before the market dies down for summer.”

But there’s no guarantee of this anticipated bounty of listings, of course.  We’re all expecting it, but those expectations are based on hope.

On Thursday of last week, I received an email about that one house, that had been sold conditionally, saying that the condition had not been satisfied and that sale had fallen through.

Imagine that?

How rare is it to see a conditional sale fall through in Toronto?  Let alone on a $3,500,000 house.

I remember back in 2005, I was in my second year in real estate.  I showed a house in Bloor West Village and got all excited because my clients wanted to make an offer, but that excitement was very short-lived, as the property was updated as “sold conditionally” when I got back to the office to draft the paperwork.

Exactly one week later, my Blackberry buzzed, and it was the listing agent for that property.

I had actually fantasized about this moment.  It was surreal.  I answered the phone and she said what I was dreaming she might say: “The sale fell through.  The property is now available again.”

And my clients bought it that evening.

It was the largest sale I had completed at that point.

Stories like this are rare, however.  Conditional sales on residential real estate rarely fall through, and since so few actually sell conditionally, it makes for an even smaller percentage that these events would transpire in 2023.

But that one house in North Toronto was now “BOM” or back on market, as we say.  And my clients asked me to show it to them at 9:00am on Good Friday.




Due respect to those that took a day off from work, whether it was to observe a religious occasion, or whether it was merely to rest and recharge.  But one day in this business can be an eternity…

On Thursday night, I got a message from the listing agent: “Offer Registered.”


Except, not great, because that ‘great’ was sarcastic, unlike the great that I thought might happen on Good Friday.

I’ve been selling real estate for almost twenty years now, so far be it for me to say that I often just know when a house is right for clients.  Sometimes it’s too early in their search, sometimes they don’t know it themselves, and sometimes they come to know it after it’s too late.  But I knew this house was perfect and I was hoping it wouldn’t sell yet again before we even saw it.

At 8:45am that morning, the listing agent told me that the offer had not turned into a sale, and that there was nothing on the table at the moment.

So I went to see the house with my clients and both their kids, and I let them tour freely while I watched and observed.

I don’t “sell” properties to clients.  I don’t cheerlead.  I don’t pump.

I prefer that buyers come around in their own time, in their own way, and I’ll provide my opinion when I’m asked for it.

This was a 32 x 140 foot lot, and the developer went to the committee of adjustment to allow for a wider and taller house than every other on the street.

The house was massive.  The lot was deep.  The ceilings were enormous.  The square footage was plentiful.  And above all, the style was great.

We had seen some houses that were so over-decorated and over-renovated that people seemed to be paying $700,000 premiums for “new.”

If you painted a kitchen cabinet in liquid gold at a cost of $50,000, does that make the house “worth” $50,000 more?

My clients were savvy and they were of reasonable taste.  They wanted a house that stressed functionality over finishes.  They wanted a house with a layout that suited their lifestyles and kept their family unit in tact.

I knew this house was perfect, but I let them slowly come to that conclusion, providing input when asked, and blunt assessments as I always do.

We were in the house for ninety minutes, and when we finished, they said they would have a conversation and get back to me, but that they were likely going to make an offer.

I left and went to the office to down a much-needed coffee and prepare for my 12:00pm appointment, but in between, I called the listing agent.

“The Listing Agent.”

It sounds like a B- series streaming on Netflix, made in Spain, dubbed in English, with a title that’s translated from Spanish and thus makes no sense.

In our industry, “the listing agent” can take on a certain connotation.  Often, agents will view the listing agent as an adversary.  Often, buyer agents will believe that every negotiation is distributive, which means that every gain for one side results in a loss for the other.

But in this business, it pays to know the listing agent.  And when you are the listing agent, it pays to know the buyer agent.

More than ever before, I’m making calls to, and receiving calls from, other agents who say, “Oh, thank God I’m speaking to you.  The shit I’ve dealt with to this point, wow, you wouldn’t believe…”

Agents want to work with like-minded individuals who are professional in nature, who are courteous, who are honest, and who have the same goal in the end: to get a deal done.

The term “playing games” gets thrown around a lot; so much so, that it’s overused and has lost meaning.

But there are times when agents will actually mess around, to the detriment of the negotiation, and it seems as though their primary objective isn’t buying or selling a house, but rather getting one over on the other side.

I called the listing agent for the North Toronto property and we talked a little shop.

How is the market?  How are the kids?  Why are you working on Good Friday?

It’s not forced small talk but rather genuine interest and concern.

I’ve done several deals with this agent and they have all been smooth.  So just as I was happy to see his name on the listing, he was happy to see mine come up on his call display.

“My clients are interested in the house,” I told him.  “What’s going on right now?”

This is where some agents will either refuse to engage in a conversation or simply feel the need to spin an unnecessary web of lies that serve no real purpose.

But he’s a pro.  He knows I can get this house sold for him; a house that’s already been sold once, and fallen through on a condition.

“We had an offer last night,” he told me.  “But it didn’t go anywhere.”

“Where did it go wrong?” I asked him.

Again, this is where some agents clam up, but he knew he could engage me and pique my interest.

“Just the wrong people on the other side,” he said.  “You know when you’ve got an agent that’s fucking around and a buyer that’s focused on all the wrong things,” he said.  “Like, we know where we need to be to get a deal done, so let’s get there together,” he said.

I told him, “Straight up: we like the house.  We could make an unconditional offer, with your clients’ preferred closing date, and it would be about $100,000 under list.”

He said, “You’d get a sign-back for sure, man.  We don’t need to take a hundred-grand under list.”

I knew that.

It was a great house.  On a better day, it could sell over list, and I’m sure they had their full $3,500,000 list price on paper when they sold the house conditionally, but once a sale falls through, a seller loses momentum and loses leverage.

“I don’t want to deal with this other agent,” he told me.  “I would much rather work with you.”

I told him, “My people are already in the neighbourhood; kids already in the school.  Our backup listing would move quickly; no issues with meeting your closing date.”

He then said, “That’s the fucked up part with that offer, right?” and he began to vent.  “Like, we had a deal.  We agreed on a price and everything, and we were going back and forth with a few terms and conditions, but we had a deal.  Then at ten minutes to midnight, they re-submit at the price but they moved the closing date six weeks!”

I hate that.

“I hate that,” I told him.  “I know exactly what they were doing.”

“They were just negotiating to negotiate,” he said.  “Like, they couldn’t bring themselves to buy this awesome house and move on without getting something needless in return after we’d already agreed.”

I knew the type.

“I know the type,” I said.  “I bet their first offer had conditions, and they took one out every time they signed back.”

“Fuck yes, they did!” he told me.  “Exactly what they did.”

“Not from the area, or anywhere close?” I asked.

“Exactly.  Just no clue.”

There are many different types of negotiation just as there are different styles and strategies.

One of my most hated types of negotiation is when a buyer puts multiple conditions in their offer – none of which they actually want, so that with every successive sign-back, they can remove a condition and muse, “I’m removing a condition, so I’m giving you something you need.  So give me something I need and come down on price.”

By that logic, a buyer could put one-hundred conditions in their offer, remove one condition on each of one-hundred successive sign backs, and eventually get the property for zero.

You might think that this is a good strategy, but not when listing agents have seen it before, been annoyed by it before, and can see it coming a mile away.

“These people were just brutal to deal with,” the listing agent told me.  “At midnight, after their last stunt, my sellers just said ‘forget it’ and went to bed.”

Price isn’t everything in a negotiation, especially when you’re dealing with a family home.

“My sellers want their kids to finish the school year and not be rushed to move out the day after the one kid graduates,” he said.  “So closing a week into July is reasonable.”

I agreed.

“The buyers really didn’t seem to care when they closed, but when we agreed on a price, they suddenly wanted to close in Mid-may.  Like, what’s that about?”

It’s about stupidity if I’m being honest.  It’s about greed.  It’s about bargaining toward a process instead of an end result.  Buyers like that lose sight of the end goal.

I finally said to the listing agent, “Where did this fall apart on price?”

He laughed and said, “I don’t want to answer that.  I mean, I can’t.  Ya know?”

He can, for the record.  We’re both pushing toward an end goal, but we have to be comfortable enough with one another and there’s a certain level of trust required.

“My guys want this house.  We can give you what you want.  But you have to name it.”

So he told me.

“We would be fine to drop $75,000 on the price if we got our closing date, no conditions, and no bullshit.”

I then asked, “If I bring you an offer for $3,425,000, no conditions, your closing, and a nice deposit, can you get that signed?”

He said, “Yes.”

That’s trust, right there.

That’s an established relationship shining through.

I told my clients and they were totally on board.

I was in the middle of drafting the offer when the listing agent called me and said, “The buyers from last night have re-submitted.”


But before I could express the feelings behind that beautiful acronym, he said, “Just get me your offer.  My clients don’t want to deal with these buyers or their agent anymore.”

We submitted our offer with a one-hour irrevocable.

And within forty minutes, the offer was sent back to us, signed and accepted.

My clients were able to purchase this gorgeous home, in part, because the listing agent I was dealing with was somebody I knew and trusted, and was somebody with whom I played fairly and treated with respect.

While we were competing for the property, the other buyer never had a chance.  That buyer misread the room.  That buyer messed around and messed around, and ultimately the sellers said, “Go away.”

The best part about this was that after I told my clients we had bought the house, the listing agent called me back and said, “That other agent is all hurt now, saying it was unfair, saying that they didn’t get a fair chance to buy the property, telling me he’d bring $100,000 over the list price.”

Who knows if that’s true.

If it is, then good for my clients.

If it’s not, then it just goes to show that the other agent still hasn’t learned how to deal with people.

Over the last month, I have spent dozens of hours on the phone calling agents that I know, asking what properties they might have coming to market, or if any of their colleagues have pocket listings or exclusives.  With inventory at an all-time low, you have to shake the trees out there, and it’s these phone calls that keep your name top-of-mind with the other agents that actually do business.

There are 72,000 agents licensed in the GTA.  I don’t have the stats to say “one percent does ninety-nine percent” of the business out there, but the agents that you know and trust are the agents that know and trust you.

A lot of deals are being consummated out there today because of working relationships, just as a lot of deals never get off the ground because two agents never get on the same page.

A “feel-good deal” this time around, indeed…

Written By David Fleming

David Fleming is the author of Toronto Realty Blog, founded in 2007. He combined his passion for writing and real estate to create a space for honest information and two-way communication in a complex and dynamic market. David is a licensed Broker and the Broker of Record for Bosley – Toronto Realty Group

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  1. KB

    at 2:32 pm

    I understand the idea here, but if I were selling and my agent had me take a deal when there was even a chance of a deal at *175 thousand dollars more* on the table, I would fire them. Would the seller agent have done this if it was their own house and their own money on the line? 175k can buy a lot of annoyance over paperwork.

    You just can’t tell someone to take an offer that is 75k lower than one offer and 175k lower than another one because you “like the other agent”…

    1. Jennifer

      at 5:46 pm

      where are you getting these numbers from? Their offer was lower on list, but I dont think he disclosed the others’ price.

      1. Toad

        at 6:29 am

        He said they offered 75k lower than list but the other potential buyer was now going to offer 100k higher than list. A 175k swing.

        1. Jennifer

          at 12:35 pm

          oh…but that was after the fact. sellers did not know that at the time…

    2. Different David

      at 10:57 am

      It sounds like the seller was getting frustrated and instructed their agent to give up on that potential buyer.

  2. JL

    at 11:40 pm

    David – in this (and a few other recent stories), you show a shift towards revealing details to agents for the sake of getting deals done and moving the process along (or praising agents for doing that), but in many earlier posts you always pushed back when readers suggested you provide that kind of direction to those “what are you looking for?” or “if I give you X, should I bother sending an offer?” type inquiries. The position was always – its not my job to educate on pricing, submit an offer and then I’ll tell you what we think, etc. Understanding that in these latest stories the agent-to-agent relationship is what you’re highlighting as the difference, I do hope the industry could work towards making the more transparent approach more of the standard rather than the exception.

  3. Ace Goodheart

    at 10:23 am

    I once bought a house where the seller had a condition in the APS. We walked in on the conditional sale, and my Agent said “they are still doing showings” to which I replied “then I want to see this house”.

    The condition was to be waived by the seller, not the buyer (weird, but that is what the APS said).

    So we were able to determine the conditional sale price, and what we did is just offer more (basically, gave the seller what they actually wanted) in a kind of “side agreement” which could not be made official until the condition in the existing APS expired.

    The seller then just let the condition expire, the APS died on the table, and we made our offer, which the seller accepted.

    It is true that without co-operation between the two Agents, this could never have happened as our offer was basically a “gentleman’s agreement” which was not in writing and had no legal force or effect (the house was, at the time we made our agreement, already sold to someone else).

    I agree that “goofball behaviour” on behalf of Agents is not really helpful in these transactions, and you “catch more flies with sugar than you do with salt”.

  4. Vancouver Keith

    at 2:20 pm

    In Europe for a very long time, they had the guild system, a precursor to professional associations and unions. You apprenticed in the shoemaker or silversmith guild, and worked and learned for a number of years before you were unleashed on the public to practice your craft on your own for money.

    In Switzerland, most people don’t go to university the way they do here. It’s an apprenticeship/co op model. If you want to be a banker, you work in a bank four days per week and go to school one day. If you decide banking isn’t for you, you find another industry and go to work and learn there.

    The model of becoming a real estate agent or stockbroker here is laughable in comparison. A minimal amount of training, then you’re licensed to work alongside people who have been in the industry for decades. The sad thing is that in Europe the co op model of employment training ensures quality workers and good wages. In North America we have millions of jobs that don’t pay a living wage.

  5. Appraiser

    at 2:34 pm

    “Canadian Rents Surged in March, With Two “Immigration Hot Spots” Outpacing All Other Markets”

    “…rent growth was the steepest in Scarborough and Brampton. In March, rates in those “immigration hot spots” climbed 34.9% and 29.1%, reaching averages of $2,527 and $2,518, respectively, making them the fastest-growing rental markets in all of Canada.”

  6. Joss Covenoho

    at 8:19 pm

    Well, this brokerage has reported the shock of my lawsuit against listing brokerages, you should read their other posts. It is illegal for the listing brokerage to refuse the valid offers of their listing brokers, and I am trying in court to ensure that it is also illegal for listing brokers to refuse the valid offers of cooperating brokerages, because MLS does not permit this… the listing agreement is extended to you and should not exploit you. The fact that you ask if listing brokerages can be trusted alarming… No.. they act as blocks…forgetting that they are required to ”cooperate” when they use MLS. If they don’t want to cooperate, they must use an Exclusive listing and waste all of their own time and money.

    Joss Covenoho

  7. DAF

    at 11:29 pm


Pick5 is a weekly series comparing and analyzing five residential properties based on price, style, location, and neighbourhood.

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