How to Keep Your Connecticut Real Estate Deal from Falling Apart: Align Before You Look or List
Or: How to Keep Your Deal from Dying on the Car Ride Home
Last week, I wrote about Alex and Beth.
They didn't lose one deal. They lost deal after deal because they weren't aligned on how decisions got made.
Beth felt it quickly. Alex needed time and numbers. Neither was wrong.
But they never dealt with that difference. Under pressure, hesitation took over. Eventually, they stopped looking altogether.
Real estate deals fall apart for a lot of reasons. Inspections. Appraisals. Financing. Sellers changing their minds. Buyers getting cold feet.
You can't always control all of that.
What you can control is how aligned the decision-makers are before pressure shows up — who's involved, how decisions get made, and where the blind spots are.
The Alignment Conversation (Before You Tour or List)
This isn't a checklist you run once and forget.
You might cover it in one sit-down. You might come back to it. What matters is that it happens early.
Identify the Real Decision Makers
There are formal decision makers — the people signing documents and holding legal authority.
And there are informal decision makers — the people whose opinions can materially affect confidence and outcomes.
Informal decision makers can include:
parents or in-laws
adult children
a friend "who knows real estate"
a trusted advisor or coworker
To identify these people, ask yourselves:
If we went under contract tomorrow, whose reaction would matter?
Who would we call or text immediately?
Who would we worry might object later?
If you really think about it, the list usually isn't long — and it's rarely surprising.
Resourcse:
A simple worksheet to list formal and informal decision makers and decide how and when they'll be involved.
Understand How Each Person Decides
Once you know who matters, the next step is understanding how decisions get made.
Some people are data-driven. They need numbers, scenarios, and time. Some people decide by feel. They know quickly when something feels right — or wrong.
Most people use both approaches. But under pressure, people lean harder into whichever comes more naturally.
Talk through questions like:
In past big decisions, what helped you feel ready to move forward?
What tends to slow you down or create doubt?
When you're stressed or excited, what do you sometimes miss?
The output here isn't agreement.
It's a shared understanding of how each person moves from uncertainty to commitment — and where hesitation is likely to show up.
Set the Boundaries Before Emotion Takes Over
This is why boundaries need to be set early.
For Buyers
Get specific:
Must-have (3-5 items, max) vs nice-to-have
Monthly payment comfort range
A clear walk-away number or escalation rule
Resource:
This helps turn vague preferences into real decision criteria before emotions take over.
For Sellers
Alignment here matters just as much:
Do all owners agree it's time to sell? If not, what needs to happen to get there?
Where are you going when the home sells? Buying? Renting? Already handled? Not applicable (rental or probate)?
What matters most in an offer — price, timing, certainty, or terms?
How quickly do you actually need to sell?
Are you open to making repairs?
Resource:
Because listing a home without agreement usually doesn't end well.
Decide How Outside Input Will Be Used
Informal decision makers don't derail deals because they're malicious.
They derail deals because they're brought in too late.
The principle is simple: Include them when there's still time to adjust the plan, not after you're already committed.
That can look like:
sharing and discussing listings you're considering
having them drive by the property, if practical
sending photos or video from showings or a video call during a showing
inviting them to a small number of representative showings
Just as important are the ground rules.
Be clear about:
what feedback is helpful (blind spots, questions, concerns)
what's not helpful (late-stage second-guessing without specifics)
This isn't about shutting people out. It's about setting expectations.
I know what this looks like from the other side.
A couple months ago, my daughter moved to Boston. She sent me listings, videos from showings, questions about budgeting and lease terms. We talked through neighborhoods, public transportation, parking, apartment layouts.
One place looked cute but had ancient windows—probably lead paint, definitely drafty in winter. I told her it was her call, but that might be one to skip. She and her roommate passed on it. They're happy they did.
She found a great apartment in a good neighborhood. They love it.
I wasn't on the lease. I wasn't paying rent. But I was involved. I saw the options. I understood her thought process. That's what informal decision makers need—not control, just enough involvement to feel confident the person they care about is making a sound decision.
That same principle applies even more when the stakes are higher and the number of decision makers is larger.
What This Looks Like When It Actually Works
Jessica was acting as Administrator for a family member's estate in Milford, CT.
Along with her day job and personal life, she had to review, document and report to the court the status of the relative's estate. This included a house.
There were 20 heirs. With their spouses, that's a lot of formal and informal decision makers.
Most of the estate was straightforward—sell the stock, secure the valuables, pay the bills.
The wild card was the house. It needed work.
We spent an hour or so walking through and documenting the condition. I helped Jessica understand what would add value and what would be a waste of time and money.
Jessica then worked with the other heirs to get general consensus on repairs, sale price, and marketing strategy. They had a contractor fix some electrical issues, repair a leaky porch roof, and fix the bathroom flooring.
Once everyone was on board with the plan, we listed the house for $420k.
It sold in a few days for full asking price.
Had we not gotten that alignment early—with 20+ people who each had opinions, concerns, and legal standing—things could have gone very differently. Delays. Disagreements. Court involvement. Instead, we had a plan, everyone knew the plan, and when the time came to execute, nobody hesitated.
That's what alignment buys you: speed, clarity, and confidence when it matters most.
When Misalignment Shows Up Mid-Process
Even with preparation, things can surface.
Common scenarios:
your mother walks the property after you're under contract and says "I don't feel safe here"
your spouse who said yes to the offer suddenly can't sleep and wants out
your brother-in-law who "knows contractors" shows up at the inspection and declares the house a money pit
When that happens:
pause before reacting
talk to your agent - experience dealing with this matters
figure out what the objection is really about (the house, the money, the timing, the risk, or readiness)
then decide whether to fix the alignment — or walk away from this house
Walking away from a house is frustrating.
Dragging unresolved misalignment forward is worse.
Where a Good Agent Helps
This is where a good agent earns their keep.
Not just finding houses or writing offers — but:
surfacing who's really involved
noticing hesitation before deadlines
facilitating hard conversations without family baggage
helping plan when and how informal decision makers are looped in
If you'd rather not referee all of this yourself, this is work I do with clients across Connecticut.
Closing
Pressure doesn't create problems.
It reveals whatever wasn't settled early.
Alignment isn't extra. It's practical preparation.
Whether you're moving this year or years from now, these conversations are worth starting before you're sitting in the car, replaying a showing, and wondering why something suddenly doesn't feel right.
