Start here, every time. Ask, how many homes have you closed in this specific area in the last twelve months. Not the whole Bay Area, your city, your zip code. I've worked the Peninsula and San Francisco long enough to know that a great agent in Sacramento isn't automatically the right fit for a listing in Pacifica. Ask for three recent closings you can look up yourself. If an agent hesitates or gets vague, that's information, and it's worth paying attention to before you sign anything.
I'm licensed under CA DRE# 01981755, and I still bring up my recent Daly City and South SF closings unprompted when I meet a new buyer or seller. That's not a sales pitch, it's just how I'd want any agent to introduce themselves to me if the roles were reversed. When someone is trusting you with the biggest transaction of their year, specifics matter far more than a polished bio.
How Will They Actually Communicate With You?
Ask this directly. If I text you on a Sunday with a question, when do I hear back. Get specifics, same day, next business day, whatever it is, and hold them to it. A lot of deals go sideways not because of bad advice, but because nobody heard from their agent for four days during a critical window, like an inspection contingency deadline or a counteroffer that needed a fast answer.
I tell people upfront, text me anytime, and I'll get back to you same day, usually within a couple hours. That's not a brag, it's just table stakes for doing this job well. If an agent can't commit to something similar during the interview, that pace usually gets worse once you're actually under contract with them, not better.
What's Their Plan If the First Offer Falls Through?
Any agent can look confident when things are going well. Ask what they actually do when an offer falls through, an inspection turns up something ugly, or a buyer gets cold feet. What happened the last time a deal you were working on almost died, and how did you save it, is a great question. The answer separates people who've actually been in the trenches from people who haven't.
I've had deals where a buyer's financing fell through two weeks before closing, and the fix wasn't luck, it was already having a backup plan in motion before the first plan officially failed. That kind of instinct only comes from experience, and it's worth asking any agent to prove they have it.
Are They Being Straight With You About Price?
Ask a potential listing agent to walk you through their number, not just tell you the number. Show me three comparable homes and explain the adjustments is fair game. If an agent's estimate is noticeably higher than everyone else's, ask why. Sometimes it's a real market read. Sometimes it's a tactic to win the listing, with the plan to quietly suggest a price cut a few weeks later once the home has sat too long.
What Happens If You Want to End the Relationship Early?
Ask to see the actual listing or buyer representation agreement before you sign, not after. Understand the term length and whether there's a cancellation clause. A good agent won't dodge this question or make you feel guilty for asking it. They'll simply show you the paperwork, because they're confident enough in their own service that they're not worried about you wanting out.
What About Their Marketing Plan, If You're Selling?
If the conversation is about listing your home rather than buying, add one more question to the list. Ask exactly how they plan to market it, professional photography, a specific launch day, where the listing gets syndicated beyond the MLS, and whether they've got a plan for the first weekend of showings. A vague answer here usually predicts a vague result once your home is actually live.
I walk every seller through a real, written plan before we ever put a sign in the yard, timeline, photography date, marketing channels, and what the first two weeks are supposed to look like. Ask to see something similar from anyone you're interviewing, and be wary of anyone who can't show you one.
How I'd Actually Run This Interview If I Were You
Treat it like a real interview, not a friendly chat. Write your five most important questions down beforehand so nerves or a good sales pitch don't knock you off track. Take notes during or right after each conversation, because after talking to two or three agents in the same week, the details blur together faster than people expect, and you want to be comparing facts, not vague impressions.
The Bottom Line on Hiring Well
None of these questions are meant to make the process feel adversarial. Most agents, including me, welcome them, because a client who asks good questions upfront tends to be a client who stays informed and confident all the way through closing. Think of the interview less as an interrogation and more as the start of the working relationship itself, since how someone handles being questioned closely tells you a lot about how they'll handle pressure later.
A Final Thought on Trusting Your Instincts
After you've asked every question on this list, give yourself a moment before deciding. The right agent relationship should feel like relief, not obligation, someone you'd genuinely want updating you throughout one of the biggest financial decisions of your life. If that feeling isn't there after the interview, it's worth continuing your search rather than settling.
If you want to talk through where you're at, no pressure and no pitch, I'm always happy to chat. Reach out anytime.