23 Questions

1. How many sales like mine have you actually closed, not just sales overall?

Why it matters: "I've sold a lot of homes" tells you nothing. An agent who mostly works with relocating employees and an agent who mostly works with families dividing a household in a divorce have built completely different skill sets, even if both call themselves full service. You want to know if this person has stood where you're standing.

Buyer's version: Same question, aimed at your situation instead. Has this agent helped someone buy under the same kind of pressure you're under?

Red flags: A vague number. A pivot to total sales volume instead of your specific situation. Any version of "every deal is different anyway" offered as a reason not to answer.

2. Walk me through what the first two weeks would actually look like.

Why it matters: This is the question that separates an agent with a real process from an agent running on momentum. You should hear a sequence: what gets done, in what order, by when. Not a promise that they'll "take care of everything."

Red flags: An answer built entirely out of marketing language. No ability to name a concrete first step without checking a script.

3. What happens if I need to pause, slow down, or change my mind partway through?

Why it matters: Life transitions don't move in a straight line. A custody arrangement shifts. A doctor's appointment changes the whole week. A sibling has second thoughts about selling Mom's house. You need to know now, before you're in it, whether this person will make you feel guilty for being a person, or whether they'll adjust alongside you.

Red flags: Any pressure, guilt, or a version of "well, we did sign a contract." A good agent has handled this before and answers calmly, with specifics.

4. How do you get paid, and what am I actually agreeing to if I sign with you today?

Why it matters: You deserve a plain answer to a plain question. Commission structure, listing agreement terms, cancellation terms, all of it should be explainable without a law degree in the room.

Red flags: Vague answers. Rushing past the paperwork. Any discomfort when you ask to take the agreement home and read it before you sign. Wanting to understand what you're signing isn't a delay tactic. It's the job working correctly.

5. Who else touches my sale, and can I know their names?

Why it matters: Plenty of agents work with a team: a transaction coordinator, a showing assistant, a photographer they trust. That's fine. What's not fine is finding out three weeks in that the person you liked in the interview isn't the person actually handling your file.

Red flags: Deflecting the question. "Don't worry, we've got a great team," with no names or roles attached.

6. What's the hardest sale you've handled this year, and what did you actually do about it?

Why it matters: Anyone can tell you their best story. This one asks for the honest story. Listen to how they describe a hard deal. Do they own their part in what went wrong, or does the market, the other agent, or the client get blamed? That tells you how they'll talk about your sale if it gets hard.

Red flags: Can't think of one. Blames everyone else involved. Tells it like a disaster instead of something they worked through.

7. If turning down this listing, or telling me to wait, would cost you the commission, would you do it?

Why it matters: This is the best trust question on this list. It asks the agent to imagine a moment where their interest and yours don't line up, and tell you, honestly, what they'd do about it.

Red flags: A too-fast "of course," with no example behind it. Real discomfort, or a change of subject. You're listening for someone who's actually thought about this, not someone reciting the line they know you want to hear.

8. How do you handle it when the two of us disagree on price, timing, or repairs?

Why it matters: Disagreement is normal in a divorce sale, not a sign anything's gone wrong. You need an agent with an actual process for keeping both people informed fairly, not one who quietly sides with whoever's easier to deal with.

Red flags: "I just talk to whoever answers the phone first." Any hint they'd take sides, even a small one.

9. Have you worked alongside divorce attorneys or mediators before?

Why it matters: A divorce sale often runs on legal deadlines, court approvals, or a mediator's schedule. An agent who's done this knows how to keep the sale moving without stepping on legal ground that isn't theirs to touch.

Red flags: No experience with this and no interest in learning the process. Resistance to looping in your attorney on communication.

10. How do you protect my financial privacy from my ex during this process?

Why it matters: Financial details get sensitive fast in a divorce. You have a right to know what this agent will and won't share, and with whom, without checking with you first.

Red flags: A casual attitude about handing financial details to "the other side" without asking you.

11. What's your plan if the legal timeline and the real estate timeline don't match up?

Why it matters: Court dates and listing calendars rarely move at the same speed. You want an agent who expects that friction and has worked through it before, not one who gets frustrated when a sale can't move as fast as they'd like.

Red flags: Impatience. Pressure to "just get it done" regardless of where things stand legally.

12. Have you handled a probate sale before, and do you understand what makes it different?

Why it matters: Probate sales can involve court confirmation, executor authority, multiple heirs, and disclosure rules that vary by state. This isn't the moment for an agent's first probate deal to be yours.

Red flags: Confusing probate with a standard sale. No familiarity with your state's court requirements.

13. How do you handle it when the heirs don't all agree?

Why it matters: It's common, not shameful, for siblings or family to disagree about price, timing, or what to keep. You need someone who can hold space for that without playing favorites or rushing anyone toward a decision.

Red flags: Frustration at "too many decision makers." Trying to align everyone through pressure instead of patience.

14. What do I actually do with the belongings still in the house, and do you have people you trust for that?

Why it matters: Clearing out a family home is often the hardest part, and it's rarely a real estate question at all. A good agent either has real referrals (estate sale companies, donation pickup, junk removal) or is honest that it's outside their lane, instead of leaving you to sort it out alone.

Red flags: No resources, no referrals, no acknowledgment that this part is hard.

15. If I'm not ready to make decisions about the house yet, what are my actual options?

Why it matters: Grief doesn't run on a real estate calendar. You may need weeks or months before you're ready to list, and that's allowed. You want to know your real options, renting it out for a while, doing nothing for now, a slower timeline, without pressure to act before you're ready.

Red flags: Urgency that has nothing to do with the market and everything to do with the agent's calendar. Any suggestion that waiting is a mistake, without a real reason behind it.

16. Before we talk about listing my house, can we talk about what I actually want next?

Why it matters: Downsizing isn't one plan. It might mean a smaller house, a condo, a move near family, or something else entirely. A good agent asks about your life before your listing photos. Where you want to live is only half the question. How you want to live is the real one.

Red flags: Jumping straight to listing strategy without asking what your next chapter is supposed to look like.

17. Do you understand the tax and timing considerations of a home I've owned a long time?

Why it matters: Long-time owners can run into capital gains questions, and timing a sale against other retirement decisions matters. Your agent doesn't need to be your accountant, but they should know enough to tell you when to bring one in.

Red flags: No mention of taxes at all. Confident answers about tax law that should really be coming from a CPA, not an agent.

18. Can you help me sequence selling this house and buying the next one, so I'm not caught between two mortgages?

Why it matters: Timing between a sale and a purchase is one of the most stressful parts of downsizing. You want real options laid out, a contingent offer, a rent-back agreement, a bridge financing referral, not just "it'll work out."

Red flags: No concrete strategy offered. Dismissiveness about the real risk of being caught between two homes.

19. What happens to my proceeds and my timeline if the market shifts while my house is listed?

Why it matters: Retirement plans often depend on the number this house actually sells for. You deserve an honest answer about pricing strategy and what happens if conditions change mid-sale, not just reassurance.

Red flags: Overconfidence about price with no explanation of how they arrived at it. No plan for adjusting if the market moves.

20. How do you handle sellers who aren't local for most of the process?

Why it matters: A long-distance sale needs more structure, not less: video walkthroughs, clear written updates, someone trustworthy handling anything that has to happen in person. You want to know this is a normal part of how they work, not an inconvenience to them.

Buyer's version: Same question, aimed at purchasing sight unseen or nearly so. How do they handle buyers who can't be there for every showing?

Red flags: Treating a long-distance client as a hassle. No real plan for the things you can't be there for.

21. If my moving date changes because of my job, how flexible can you actually be?

Why it matters: Job-driven moves sometimes come with a hard date and sometimes come with a date that shifts without warning. You need an honest answer about how much flexibility is realistic on both sides, not just reassurance.

Red flags: Promising flexibility that isn't realistic. Offering none at all.

22. How do you help me figure out what I actually need to price and time this sale correctly?

Why it matters: It's easy to plan for the family you'll have in five years and lose sight of what your current house needs to sell for, on your actual timeline, to make the next move work. A good agent asks real questions about where you're headed instead of jumping straight to a number.

Red flags: No real conversation about your next steps before talking numbers.

23. What happens if we're timing this sale around a due date, a school year, or another hard deadline?

Why it matters: Family moves often carry a real deadline. You need to know the agent takes that seriously and can build a realistic plan working backward from the date that actually matters to you, rather than treating every deadline as equally soft.

Red flags: Casual dismissal of your timeline. No concrete plan built around the date that matters.