The Seller Everyone Warned Me About

Field Notes
Two agents told me she was difficult. Neither had ever explained to her what was happening with her own listing.

I had the label before I had the address.

She was an out-of-state owner with a condo in Alaska that had been listed and unlisted four times across five years. I was working probate, estate sales, and fixer-uppers then, so expired and canceled listings that fit that profile got a letter from me. A few weeks after I mailed hers, she called.

I did what I always do on a first call. I opened my planner to the seller questions and started working through them. A family friend had been living in the condo, covering the dues and utilities. After they moved out, it sat. Then I asked the question that usually opens everything up: why do you think it didn’t sell?

She answered before I finished asking. She never heard from her agent. She didn’t know what marketing was being done. She had no idea how many showings it had. The photos were dark, and the place looked worse online than it did in person.

I was pulling up the old MLS listings while she talked. Every word of it was true. The photos were bad. The presentation was bad. And judging by the history, so was the communication.

I asked whether I could go look at it. She said yes.

On the drive over I called the agents who had listed it before me. One said she was high maintenance and that he had been relieved when it expired. The other said she called for updates so often that he eventually stopped picking up, because he never had anything to tell her.

By the time I reached the condo, I had two versions of her.

Then I opened the door. The photos hadn’t lied. It was dark, it was dated, and it needed work. But after years of probate files and foreclosures, I didn’t see a disaster. I saw a condo in a desirable association that would suit a first-time buyer willing to earn some sweat equity, or an investor who wanted a long-term rental. It wasn’t unsellable. It had never been positioned.

I took my own photos on my iPhone and emailed them to her the next morning. Not listing photos. Reality photos — the property exactly as it sat that day.

That’s when the real issue surfaced. She wanted someone to come in, spend their own money fixing it, and then sell it. That wasn’t going to happen, and I told her so. If she couldn’t fund repairs, we sell it as it is. Not as we wish it looked. Not as it might look someday.

Then we went through a CMA together. I didn’t use remodeled condos as the comparables. I used fixer-uppers — properties that looked like hers, competing for her buyer.

She stopped arguing with the market.

It was the first time anyone had shown her what buyers were actually weighing her condo against.

The last hurdle was money. The condo was costing her every month in dues, utilities, and upkeep, and she was struggling to carry it. So we ran net sheets and pricing scenarios and treated it the way I would treat any conversation where the clock is the real opponent. The goal was never to maximize the number. The goal was to stop the bleeding.

She agreed to the condition comparisons. She agreed to the net sheets. She agreed about what waiting was going to cost her. She wasn’t unreasonable and she wasn’t difficult — she was one of the most honest sellers I have ever worked with. She wanted information, and for five years nobody had given her any.

It closed two days before Christmas. She left a review saying it was the best gift she got that year.

What the label was actually telling me

Very little about her. Quite a lot about what had been done to her.

When nobody explains, frustration fills the gap. When nobody communicates, anxiety fills it. When nobody builds a plan, the seller starts building one herself out of guesses — and then she calls every week to find out whether the guesses still hold.

That is what “difficult” usually is. A person carrying a problem nobody has explained to them.

One thing to do this week

Open your active listings. For each one, write down the date you last told that seller something they did not already know.

Not a check-in. Not “no news yet.” Information — a showing pattern, a competing listing that just came on, what the feedback is starting to say.

Any listing where that date is more than two weeks old is where your next difficult client is coming from.

Field Notes — one real moment from the field, one lesson, one thing to do.

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