How to Choose the Right Real Estate Agent Before You Regret It
Updated: 5 days ago
Choosing the right real estate agent comes down to more than who has the most signs, the biggest social media following, or the highest sales numbers. You want someone with the experience to recognize risk, the judgment to give honest advice, and the communication skills to stay steady when a transaction gets difficult.
That matters anywhere, but it matters especially in the Richmond real estate market, where buyers and sellers may be dealing with everything from older homes and hidden repair concerns to fast-moving negotiations and major pricing decisions.
The Short Answer
The right real estate agent is someone you trust to tell you the truth—even when the truth could cost that agent a commission. Look for sound judgment, specific experience, a clear communication plan, local knowledge, and proof that the agent can solve problems when the easy plan stops working.
Key Takeaways
Interview more than one agent and ask for specific examples—not just promises.
Buyers need an agent willing to slow down or recommend walking away when the risk is too high.
Sellers need a strategy connecting price, presentation, and marketing.
Communication matters most when inspections, appraisals, or negotiations become difficult.
Choose the person whose judgment you trust when the answer is not the one you hoped to hear.
Prefer to watch?
In this episode of Beyond the For Sale Sign, I walk through the questions buyers and sellers should ask before choosing a real estate agent—and what the answers can tell you about the person you may be trusting with one of your biggest financial decisions.
A friend’s recommendation, a familiar name, or a yard sign you see all over town can be a perfectly good place to start. But it should not be the end of the decision.
Almost any licensed agent can schedule a showing, put a home in the MLS, and help move paperwork toward closing. The bigger question is what happens when the house has a problem, the pricing conversation gets uncomfortable, or the transaction starts to wobble.
That is when the agent you chose really matters.
Will your agent tell you what you need to hear?
If you are buying a home, there is one question I would ask right up front:
“Will you tell me not to buy a house if you believe it is the wrong one?”
The answer should be yes.
Some of the prettiest homes deserve the closest look. A renovated or flipped house may have fresh paint, new flooring, an updated kitchen, and beautiful staging. But none of that tells you what is happening behind the walls or underneath the house.
There could still be aging cast-iron drain lines, aluminum wiring, drainage problems, or other expensive concerns hiding beneath those cosmetic improvements.
After more than 35 years in real estate, I would rather lose a sale today than have a client call me years later and say, “I wish someone had warned me.”
A good agent should be willing to slow things down, ask more questions, and risk losing the transaction when the situation calls for it.
Experience should change the advice you receive
The number of years someone has been in real estate matters only if those years help the client make a better decision.
Before I worked in residential resale, I spent years in new construction and learned how homes come together—from the foundation through the roof. I have also attended close to 2,000 home inspections.
That does not make me a home inspector. It has, however, taught me to recognize patterns. I know where problems often show up, which questions deserve more investigation, and when a polished surface should not be the end of the conversation.
When you interview an agent, ask for examples. How did that person’s experience help a client avoid a costly mistake, negotiate a better outcome, or catch a problem before it became a crisis?
You are not just looking for a résumé. You are looking for judgment.
Sellers need a strategy, not a promise
If you are selling, do not stop after asking how the agent will market your home. Ask this instead:
“Can you show me where your strategy made a difference?”
We have worked with sellers whose homes had already been listed with another agent and did not sell. Getting those homes sold took more than putting them back into the MLS.
We had to take a fresh look at the price, presentation, photography, video, and overall marketing plan.
No single piece deserves all the credit. Pricing matters. Presentation matters. Marketing matters. The right strategy brings all three together.
Be careful with an agent who simply promises the highest price or tells you everything you want to hear. A strong listing agent should be able to explain the thinking behind the recommendations—even when that conversation is uncomfortable.
Learn how Two Dog Realty helps Richmond-area sellers prepare, price, and market a home.
Communication matters most when things get difficult
It is easy to communicate when everything is going smoothly. You learn much more about an agent when the inspection finds problems, the appraisal comes in low, or a negotiation starts getting emotional.
Some transactions do not fall apart because the people are impossibly far apart. They fall apart because communication stops. Positions harden, frustration takes over, and everyone becomes more interested in winning the argument than solving the problem.
In one recent transaction, the buyers made request after request until our sellers were ready to walk away. Heather kept everyone talking, helped keep emotions from taking over, and brought the conversation back to workable solutions.
The transaction moved forward and closed.
That work is not visible on a yard sign or a property-search website. But it is often where an experienced real estate agent truly earns the fee.
Before choosing an agent, ask who will communicate with you, how often you should expect updates, and what happens when a negotiation becomes strained.
Seven questions to ask before choosing a real estate agent
Will you tell me not to buy—or not to accept an offer—if you believe it is the wrong decision?
Can you give me an example of how your experience helped a client avoid a costly problem?
Who will communicate with me, how often, and by what method?
Tell me about a difficult transaction you helped keep together.
If I am selling, how will pricing, presentation, and marketing work together?
If I am buying, how will you help me evaluate condition, location, price, and long-term fit?
What will you do when the honest advice is not what I want to hear?
Listen carefully to the answers. Specific examples tell you much more than polished promises.
What Richmond-area buyers and sellers should listen for
Real estate is local, and the advice should be local too. An agent working in Richmond, Chesterfield, Henrico, Hanover, or the surrounding communities should be able to explain how the age and style of the home, neighborhood conditions, buyer competition, inspection concerns, and current market activity affect your decision.
You do not need someone who pretends to know everything on the spot. You need someone who knows which questions to ask, where to get a reliable answer, and when to bring in the right professional.
That combination of local knowledge, experience, and humility is a much better sign than a rehearsed sales pitch.
Frequently asked questions
How do I choose the right real estate agent?
Interview more than one agent and look beyond sales numbers. Ask about experience, communication, local knowledge, problem-solving, and whether the agent is willing to give advice that could cost them the sale.
What questions should I ask a real estate agent before hiring them?
Ask who will communicate with you, how often you will receive updates, how the agent has helped clients avoid costly mistakes, and what the agent does when inspections, appraisals, or negotiations become difficult.
Should I choose the agent who suggests the highest listing price?
Not automatically. Ask the agent to support the recommended price with current local evidence and explain how price, condition, presentation, and marketing will work together.
Is it okay to interview more than one Realtor?
Yes. Comparing two or more agents can help you understand different approaches and decide whose experience, judgment, and communication style fit you best.
Does an experienced real estate agent really make a difference?
Experience matters when it improves the advice you receive. The useful question is not simply how long an agent has worked in real estate, but how that experience has helped clients recognize risk, negotiate well, and solve problems.
What should Richmond-area buyers look for in an agent?
Look for someone who understands the Richmond-area market, can help you evaluate a home's condition and long-term fit, and knows when to slow down, investigate further, or recommend walking away.
What should Richmond-area sellers look for in a listing agent?
Look for a clear strategy that connects pricing, preparation, presentation, photography, video, marketing, communication, and negotiation—not just a promise to put the home in the MLS.
About Curt Reichstetter and Two Dog Realty
Curt Reichstetter is a Richmond, Virginia–area real estate broker, co-owner of Two Dog Realty, and 2026 President of Virginia REALTORS®. Curt and Heather Reichstetter help buyers and sellers throughout Richmond and the surrounding communities with honest advice, careful preparation, and steady guidance from the first conversation through closing.
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Curt Reichstetter
Two Dog Realty
804-370-1210
curt@curtsellsrva.com
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