I guess the title can be taken both ways: listings that an agent loses through cancellation/expiration and listings that lose the agent money.
Both have the same result: the agent loses time, money, focus and momentum on a listing that not only generates no income, but most likely no referrals either.
But boy can one learn from them.
As a newer agent last summer, eager to get more listings, I called several expired/cancelled listings to set appointments.
Mistake number one: I called someone who had cancelled not one but two listings with two firms in the past 6 months.
Mistake number two: I heard the client admit there were personality issues with the 2nd agent and assumed I could work with him better, even when I saw the defensive letter from agent # 1 justifying and listing the marketing budget they had done on his behalf.
Mistake number three: He brought his price down a small amount (so it was at the very top of where it should be marketed) but announced he would not ever lower it again.
Mistake number four: 5 weeks into the listing, when three Open Houses yielded only one buyer party (and several of his friends he sent through to "test" me), four showings all said it there were better values and his two main competitors had lowered their prices, I went to see the client. I had data, absorption rates, statistics, floor plans and photos of the competition, marketing packages, etc. His response - I am not lowering the price - if you don't believe in MY price, I will fire you know because you will never get me a price if you don't believe in it yourself. At that point, he took charge of the arguement, I demurred. I was put in the position of being the one on the defensive now...my lack of experience showed. I spoke of the market and the buyers believing in the value of this house over another house, kept me and "his price" out of the equation.
I should have said fine - fire me. No matter how nice the house, how nice the finishes, the landscaping, etc.
Because no surprise, his house sat like a stale cookie on a plate while the competitors who lowered their prices sold - one for far less even than the new price. And no surprise, he cancelled the listing as soon as the contract's 180 days before cancelling was up....In the meantime, I would call him with market updates, marketing ideas and he would say why are you calling me with this - my price is my price...and take it as a personal affront that I suggested HIS house had less value than he thought. And he would call on a random Sunday at noon and say - what time is my open house today, I don't see it in the paper and I want one - today or I am cancelling my listing. I don't care if you have other Opens, I want mine open.
And all I felt was relief that this negative person was out of my life. The failure was not losing the listing, the failure was not seeing before hand the outcome.
Biggest mistake was not realizing that for him - it wasn't about selling his house, it was about "validating" his point of view. It was about ego more than equity.
So I am curious, what "red flags" do other agents use when going on listing appointments. When do you refuse to take a listing - price? expectations? or can a personality do it for you as well?
Other stories?

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