Dear Listing Agents: Will You Bite The Hand That Feeds You?

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11 minute read

May 29, 2025

Nine Inch Nails is probably one of the most underrated bands of our generation.  Perhaps one of the most misunderstood as well.

When I was in high school, one of the prevailing looks, or cliques was that all-black “goth” vibe that had kids dying their hair black, wearing black nail polish, and even black trench coats which was an odd piece of clothing for a 15-year-old from Leaside on a hot summer day.

I remember after society tried to make sense of the Columbine shooting in 1999, people blamed, among other things, Marilyn Manson and his music, as well as Nine Inch Nails, simply because they liked to dress in black, as did their fans.

I’ll be honest; the guys I knew in high school who did dress in all black were fans of Nine Inch Nails, but I’ll leave history (and the Internet…) to disprove the myths of the link between 1990’s heavy metal music and violence…

In any event, Nine Inch Nails sort of gets wrapped up in this “heavy metal” genre but my god are they ever more than that.

You might not know “Trent Reznor” and “Atticus Ross” as household names, but everybody saw The Social Network, better known as “The Facebook Movie,” and all the music from the movie was scored by Reznor and Ross.  They also did the music for Gone Girl and The Girl With The Dragon Tattoo, among others that you’ve probably seen.

My favorite song by Nine Inch Nails is “The Hand That Feeds.”

What I love about the song is that it’s so hard to define the type of music therein.

It has elements of rock, pop, funk, and electronic.  Certain segments of the song feel like dance music.

🎵 Just how deep do you believe
Will you bite the hand that feeds? 🎵

Like any song, piece of poetry, or even religious text, the words are open to interpretation.  Like your horoscope.  Or a fortune cookie.

🎵 Are you brave enough to see?
Do you wanna change it? 🎵

This is how I see a lot of the Toronto real estate market right now, and while it’s hard to explain what’s going on out there, the regular readers know that I often use analogies to get my points across…

🎵 So naive
I keep holding on to what I want to believe
I can see
But I keep holding on and on and on and on 🎵

I can’t possibly tell you how much this music feels like the May, 2025 real estate market here in Toronto.

🎵 Will you bite the hand that feeds? 🎵

We have discussed the following themes ad nausem throughout 2025 thus far:

1) Sellers over-valuing properties.
2) Listing agents not educating sellers.
3) Listing agents not knowing how to work in a balanced or buyer’s market.

But there’s a new theme that I wanted to explore today, one that is borne of all three of the above themes:

4) Listing agents who bite the hand that feeds.

We could call this “looking a gift horse in the mouth” if we wanted to.

We could also say that this is like “refusing the olive branch.”

It’s “slapping away the extended hand.”

However you want to describe this; whatever your analogy might be, it’s one of the largest problems in the real estate market right now it’s a major reason why more transactions aren’t getting done.

Simply put, many listing agents refuse to work with, listen to, or even respect the buyer agent who comes to them with an offer, and I’m talking about a situation where the listing agent is out of his or her depth.

At best, this stems from inexperience.

At worst, this stems from ego and greed.

But combine inexperience, ego, greed, arrogance, frustration, unrealistic expectations, and at times – desperation, and there’s no way to expect a positive result.

Let me regale you with a story which a colleague of mine recently shared.

We’ll call her “Kim.”

Kim’s clients are looking at houses in the west end, casting the net wide enough to capture Bloor West Village, Roncesvalles, High Park, The Junction, and maybe even Dufferin Grove too.

There are a lot of options out there in their price range right now, which is up to $1,200,000, and they’re noticing that a ton of houses are failing to sell on their offer nights and subsequently being re-listed.

Kim’s clients saw one particular property that they liked, which was listed for $1,048,000, but was an odd house, with an odd layout, and one that the buyer pool might not flock to.

The property was listed with an offer date, of course, but Kim’s clients decided to take a wait-and-see approach, since so many houses were failing to sell on their offer nights.

Offer night came along and there were only two offers registered, so with the listing agent calling Kim incessantly, saying, “This house is going to under-sell,” Kim called her clients and encouraged them to consider an offer at a price that made sense for them.

They decided to offer $1,166,000 on the house, knowing full well that the “value” was probably higher and the seller likely expected more, but with only two competing offers, they feel like they were in the game.

The listing agent, who we’ll call “Realtor Kenny,” did his job and made it sounds like the three offers were all very competitive and that Kim would need to get her clients to come up in price, but Kim’s buyers held firm at $1,166,000.

Realtor Kenny called Kim at one point and said, “Can your clients come to $1,200,000?”

Kim said, “No, they’re firm at $1,166,000.”

Realtor Kenny seemed to think Kim was a priest at one point, as he began to confess to Kim.

“These sellers are really hard,” Realtor Kenny told Kim.  “They seriously thought they were getting, like, $1.3 Million, and I don’t know what they’re going to do,” he told Kim.

Kim just sat back and let Realtor Kenny talk.

“I don’t know what to do,” Realtor Kenny said at one point.  “This market is so fucked,” he added.

This isn’t uncommon in today’s market.  Listing agents are having a tough time, and some of them are sharing with colleagues.  But what is uncommon is for a listing agent to share this in the middle of an offer review, not to mention sharing it with one of the buyer agents who has an offer on his listing!

Realtor Kenny called Kim back a half-hour later and said, “I don’t know what’s going to happen.  The sellers might not accept any of the offers.”  But the interesting thing was, during this call, Realtor Kenny didn’t ask Kim to improve her offer.

Realtor Kenny just seemed to be venting.

An hour later, Kim got the call from Realtor Kenny that she felt was coming all along; he said, “Sorry, Kim, but we’ve accepted another offer.”

Kim said, “That’s fine, I understand,” and then asked what we all ask: “Can you tell me how much the other offer was for?”

Here’s where things get interesting.

Realtor Kenny said, “I can’t tell you just yet, since the other offer is conditional.”

Huh, really?

The seller accepted a conditional offer over an unconditional offer?

Well, depending on the price, that might make sense.  It’s a risk, but hopefully a calculated one.

As a reflex action, Kim said, “Oh, wow, they accepted a conditional offer?  That’s so strange!”

Surprisingly, Realtor Kenny responded with, “Well, I mean, it was just over $1,200,000.”

Amazing.

It’s amazing because Realtor Kenny just finished saying, “I can’t tell you just yet,” and then told Kim thirty seconds later.

Perhaps Realtor Kenny was being defensive?  Perhaps he felt like Kim was calling his strategy into question and he felt the need to tell her that the accepted offer was $34,000 higher than hers?

Regardless, the property was marked “Sold Conditionally” on MLS and noted conditions on financing and home inspection.

Fast-forward to the Thursday before the Victoria Day long weekend, and Kim checked her phone to see four missed calls from Realtor Kenny.

She’s been in the business a long time.  She knew what this meant.

Kim called Realtor Kenny and he sounded panicked!

He also started to butter Kim a little bit and she knew that he was going to work an angle.

“This deal is falling through,” Realtor Kenny told Kim.

She asked him, “It’s fallen through, past tense?  Or it is falling through, as in, currently?”

Realtor Kenny said, “It hasn’t fallen through yet but they let us know that they’re not moving forward.  They want to extend their condition for fifteen business days; some bullshit about their lawyer not being in town, and their financial planner not being able to give them the go-ahead…”

Kim was stunned.

Conditional sales rarely fall through in today’s market, and this most certainly surprised Realtor Kenny!  Kim could hear the panic in his voice.

“Do you think your people would come back to the table?” Realtor Kenny asked Kim.

Now, here’s where we need to pause for a moment and ask a very important question:

Who is doing whom the favour?

You could argue that Realtor Kenny is doing Kim the favour by giving her a second chance at a property that her clients wanted.

But you could also argue that Kim, if she were to get her buyers back on paper, would be doing Realtor Kenny the favour by helping to bail him out of a bad situation.

Feel free to decide how you wish.

However, in a situation like this where the offer date has passed, the original deal fell through, and the property is going to be offered up for sale again, I would argue that Realtor Kenny had lost any and all leverage that he possessed one week prior.  In fact, once a conditional sale falls through, the buyer pool often sees the property as stigmatized.

Kim told Realtor Kenny that she would check with her buyers to see if they were still interested, but added, “We saw two properties last night and we were literally just talking about making an offer on one of them.”

Realtor Kenny said, “Please, Kim.  I need your help here.  Check in with them and let me know.”

Kim said that she would.

But then, rather amazingly, Realtor Kenny said, “And see if they can come up to $1,200,000, okay?”

Wait.

What?

Kim’s clients had offered $1,166,000 on the offer night.  They were beaten by a higher offer.  That offer was conditional.  Now, that offer had fallen through.

Kim didn’t quite understand.

“Um, Kenny,” she said, “If my clients were going to $1,200,000, they would have done so on offer night.”

Realtor Kenny said, “Yeah, well, I need to get my sellers the same price as before.  Okay, yeah, just check with them, okay?”

He sounded panicked.  But of course he was!  Whether he had advised his sellers to accept a conditional sale, or whether it was their idea, it didn’t matter.  They were already hurt because they “only” got $1,200,000 or thereabouts for their home, which they overvalued, and now they were most likely pressuring Kenny to secure a firm sale.

Kim told Kenny, “I can call them and ask if they would put $1,166,000 back on paper.  Would you like me to do that, or not?”

Good for Kim.

Tell me that Realtor Kenny was “just doing his job,” but was also risking biting the hand that feeds.  He needed Kim; not the other way around.  Kim’s clients, as mentioned, were literally just about to submit an offer on another home.  Sure, they might want to take another shot at this house, but there was no need for them to raise their bid.

Realtor Kenny told Kim, “See what you can do,” and Kim said that she would speak to her clients that evening.

The panic was real, however.  Realtor Kenny was blowing up Kim’s phone.

Can u get an offer tnight?  He texted her.

Any updates plz n thx, came the second text.

This went on and on for hours.

Kim called Realtor Kenny back and before she could say anything, he blurted out, “Will they do $1.2 Million?”

She said, “Hi Kenny, first of all, no, but secondly…”

That’s when Realtor Kenny cut Kim off and said, “Well, that’s what the house is worth!  I don’t understand what the problem is here.  We already sold it for this price once, we can do it again.”

Realtor Kenny was not in a position to be lecturing Kim, and yet that’s exactly what he was doing.

But then he actually started bargaining with Kim and said, “I mean, I could probably get them down to $1,190,000, but you’d have to throw in $7,500 of your commission.”

Wow!

The balls on this guy!

I mean, say what you want about Realtors and how they’re overpaid, how $7,500 is nothing, yadda, yadda, yadda, but that’s not the point.

This wasn’t just “biting the hand that feeds anymore.”  Considering that Realtor Kenny was asking Kim to do him a favour and help him out of this jam, he was now “looking a gift horse in the mouth.”

Kim finally connected with her clients and they were unsure about resubmitting an offer.  They wanted to know that, if they did, they were in the driver’s seat.

Kim called Realtor Kenny back later that night and asked him the million-dollar question:

“Did the sale fall through?   Is it official?”

Amazingly, that was the moment when Realtor Kenny felt the need to come clean and say, “Well, the thing is, we actually have until tomorrow at 6pm.”

You’ve got to be kidding me.

Yes, Realtor Kenny was panicking and scrambling, but he wasn’t going to win any favours with Kim by lying about the condition expiry, or at best, misleading Kim.

“If you have until tomorrow night, then why are you asking me about this now?” Kim asked Realtor Kenny.

Again, Realtor Kenny was doing his job; he was mitigating.  But at what cost to his working relationship with Kim on a potential deal?

“I need to figure this out as soon as possible,” Realtor Kenny said.  “My clients are killing me right now and they want certainty.”

Certainty.

That was about the moment when, if it hadn’t been clear enough already, Kim realized that Realtor Kenny was going to do anything and everything to salvage his relationship with the sellers, even if it put Kim at a disadvantage.

Kim said, “Kenny, I realize you have a tough seller on your hands.  I sympathize with your situation.  But I have a buyer – not a seller, a buyer in an area where it’s a buyer’s market.  You have called me about a deal that is still very much alive, misled me about the condition, and asked me to improve an offer that I don’t even think I can get back on paper!”

Kim was exasperated.

But then Realtor Kenny came up with, as Matthew McConaughey said in Wolf Of Wall Street, a “bright idea; a special idea.”

He said, “Kim, why don’t you submit an offer tonight that’s conditional on my sellers being released from the other agreement!”

Really?

Perhaps Kim could also lie down in the parking lot so you could run her over with your truck?

Just consider this from Kim’s perspective: her clients were interested in two other houses, both sitting on the market without offer dates, and Realtor Kenny wanted Kim to have Kim’s buyers tie themselves into a conditional agreement, wait another 24 hours or more, and take the leverage out of their hands?

Kim told Realtor Kenny, “You’d love my offer, wouldn’t you?”

Realtor Kenny said, “Yes, of course!  Even conditional!”

Kim said, “Yep.  Then you can go to the first buyer of the home and tell them you have a second offer.  That would surely give them a reason to firm up, wouldn’t it?”

Realtor Kenny went quiet.

He stuttered a little bit, just enough to make Kim think that this wasn’t actually his master plan, but it didn’t matter, since the presence of a second offer might actually serve to light a fire under the first buyers.  After all, buyers are always more interested in a property when somebody else wants it too.

Kim spoke to her buyers later that evening and was very clear about the conversations that she’d had with Realtor Kenny.  The buyers had no intention of increasing their bid price, and they most certainly had no intention of making an offer conditional on the seller being released from another Agreement of Purchase & Sale.

The next morning, Kim submitted an offer on their behalf for a different property and it was accepted, as is.

That evening, Realtor Kenny sent Kim a text message and said, Deal fell thru.  Door is wide open.  Plz let’s do a deal!

Kim didn’t respond.

Realtor Kenny called her the next morning and she informed him that her clients had purchased something else.

He was shocked.

But why?

What did he expect to happen?

Tell me that you think this guy was a mad genius all along and this was just part of his strategy, but I vehemently disagree.  He was just an agent with no plan and no clue.  He felt that the market owed him something.  He had completely lost the ability to be impartial and to see the situation through anybody else’s eyes.

He made the bizarre assumption that Kim’s clients would come up in price to match the price of a buyer who ended up walking from the deal.

He lied about the condition expiry.

He asked Kim to throw in commission as though it was her fault the prices wouldn’t “match.”

And he then expected Kim to put her clients at a disadvantage and submit a conditional offer when they had absolutely no reason to do so.

He was waiting for other market participants to rescue him from his own doing, and all the while, alienating the people who he could have actually worked with.

I have so many stories like this right now, I can’t even count them.  Listing agents have no idea how to work in this market and it’s showing with every interaction.

Say what you want about any agent’s business acumen, demeanour, or strategy, but biting the hand that feeds is never going to work in this market.

These listing agents.  Seriously…

🎵 So naive
I keep holding on to what I want to believe
I can see
But I keep holding on and on and on and on 🎵

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

Find Out More About David Read More Posts

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6 Comments

  1. Serge

    at 7:28 am

    That dog eats dog out there…
    And think how many people (I knew) considered being a realtor a simple way to prosperity…

  2. phycological terms

    at 8:24 am

    Kenny seems to be suffering from what most real estate agents suffer from. Its called cognitive dissonance with a sprinkle of Self-serving bias, Overconfidence bias and Sunk cost fallacy.

  3. Milk Man

    at 6:13 pm

    Apologies in advance for the silly question, but how can agents be this myopic? I don’t fully understand?
    Please tell me that Realtor Kenny is a fresh-faced noob who couldn’t appreciate the repercussions of his actions? Otherwise, if “experienced” agents are pulling this kind of self-centred, short-sighted crap, then the industry clearly needs to fix itself. And I’m not even talking about top-down regulation. There needs to be some personal accountability here, right?

    1. Nobody

      at 2:05 pm

      The problem is that the market has been going up since 93 with only a few blips in 01, 08, and 17. Condos were flattish until circa 2010. Single family has been a sellers’ market from 2000 until 23.

      You can have 25 years of experience and NEVER have dealt with failed offers, conditional offers, or an over supplied market.

      Unless a realtor has experience in other geographies, with other industries, or has some experience from the 80s and 90s, a Toronto agent has literally no experience of this type of market.

      Experience as a Toronto Seller’s agent has been like a bartender at a Leafs game – just taking orders as fast as possible for $20 cans of beer.

      Up until VERY recently any conditional offer would be laughed off and in most situations still are in the price range of this story. People need experience in stressful situations to manage them well. Stocktraders need to experience losses and the psychology around them to successfully navigate complex situations. Mock trading competitions can help but the best training is with (small amounts) of real money.

      As agents are all independent there’s no training infrastructure or a minor league system where first you work in Kingston or Windsor before getting called up to Toronto. Rental listings sort of act like this, as do condos, but lack the real drama and complexities of selling owner occupied houses for less than the owner paid/needs for their next purchase.

      The personal accountability comes from a down market and screwing up. Some people get better and are more productive in future deals, others leave the industry. Agent quality in 3 years will be so much better because industry will be so much smaller.

      1. Derek

        at 11:11 pm

        My two cents is that the problem is not the up up up since the 90s but the sub-periods of parabolic UP UP UP therein. The speculative exuberance periods. This ain’t Manhattan lol. Every new high on the parabolic graph wasn’t actually the new normal economic reality that the too poor to buy people should learn to live with.

  4. Marina

    at 9:05 am

    I think people really struggle to understand the concept of advantage in the market. It’s like when in a seller’s market a buyer says “well if they want my business they will agree to my price”. That’s a pretty big if there.
    Somehow when you are at the table, it’s easier to assume that everyone wants what you have. But it happens literally EVERYWHERE.
    A good friend went through a breakup earlier this year, where the lady was like “if you want me, this is how I am and this is how you have to change”. Cue the surprise Pikachu face when he said “pass”. She couldn’t believe he opted out.
    Another friend had a promotion fall through, one she very much deserved. And when she put in her notice because she got a much better offer at a competitor, the employer again couldn’t believe it.
    I think we would all be better off if all of us realized none of us are that special. Nobody will be setting themselves on fire to keep us warm.

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

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