What Questions Should I Ask a Real Estate Agent?

Honest Advice From Vinny Fracassi aka South Philly Vinny, a Philadelphia Realtor

Most real estate blogs answering this question give you the same recycled advice.

“How many homes have you sold?”

“How long have you been in the business?”

“Do you work weekends?”

Some of those questions matter. Some really don’t.

The truth is, most real estate transactions look smooth in the beginning. The real test of an agent happens once things get difficult.

Inspections go sideways. Appraisals come in low. Financing gets delayed. Negotiations get tense. Buyers get nervous. Sellers get emotional.

That’s where communication, problem solving, honesty, and experience actually matter.

As a Philadelphia realtor, I’ve handled everything from difficult negotiations and short sales to first-time buyers relocating from out of state. So instead of giving generic advice, I wanted to answer these questions honestly based on real experience.

1. What Are 2-3 Real Situations Where Another Agent Might’ve Handled It Poorly, But You Solved The Problem Well?

Holding a Developer Accountable

I represented buyers on a new construction home in Fishtown that was still being finished while it was listed for sale. In the agreement of sale, I specifically wrote in that the sellers had to complete certain items prior to closing. Both parties signed off on it.

As we got closer to settlement, the sellers failed to deliver on what they agreed to. The listing agent was someone with far more experience than me and ran a large real estate team. A lot of agents would’ve backed down or avoided confrontation. I didn’t.

We had multiple heated conversations because, at the end of the day, my job is to protect my clients and hold the other side accountable to the contract they signed. The sellers were underwater financially, which ultimately caused them to cut corners and not finish the work properly.

After pushing hard, we negotiated a seller credit for my buyers. It wasn’t perfect, but it gave them the ability to hire their own contractor and finish the remaining work the right way.

One thing I strongly believe is that real estate agents are paid to advocate for their clients, especially when things get uncomfortable. That’s part of the job.

Managing a Difficult Short Sale From Start to Finish

I listed a property in the Kingsessing neighborhood of West Philadelphia that ended up becoming a short sale. The sellers had renovated the property and placed a tenant inside, but financially, the deal no longer made sense for them.

We eventually received an offer and went under contract, but the transaction became extremely difficult. The buyer’s agent was largely absent throughout the process, which meant I was constantly communicating directly with the buyers regarding inspections, the appraisal, lender delays, extensions, and the short sale process itself.

It felt like every week there was another issue that needed to be solved.

In many ways, I was doing the work of both the listing agent and the buyer’s agent while only representing the seller side. A lot of agents would’ve become frustrated and let the transaction fall apart. Instead, I stayed involved every step of the way and kept pushing the deal forward until we successfully made it to the closing table.

Some transactions are smooth. Others require constant problem solving. This one definitely required problem solving.

Staying Patient When Other Agents Would’ve Walked Away

I worked with buyers who were relocating to Philadelphia from Texas. The first property we went under contract on was done sight unseen. They flew into Philly for the inspection, saw the property in person, hated it, and decided to terminate the contract.

They went back to Texas, came back to Philadelphia a second time, and we toured around 12 more properties. We went under contract again, but shortly after, they had another change of heart and terminated that contract as well.

At that point, many agents probably would’ve walked away from the relationship entirely.

Instead, we stayed the course.

The buyers flew back to Philly for a third trip, we toured another dozen properties, and finally found the right fit. This time, everything worked out and they successfully closed on the home.

What makes this story even better is what happened afterward. The property they purchased was tenant occupied, and I became friendly with the tenants who were moving out. Eventually, I helped those tenants buy their own home. A few years later, they hired me again to sell that property and help them purchase another one.

That original transaction ultimately turned into four separate deals.

One thing I’ve learned in real estate is that patience, consistency, and treating people the right way tends to pay off long term.

2. What Are the Biggest Mistakes Buyers and Sellers Make When Choosing an Agent?

Buyers

One of the biggest mistakes buyers make is choosing an agent who doesn’t actually listen to them.

Some agents think they know what the buyer should want instead of listening to what the buyer actually wants. There’s a big difference between guiding someone and completely ignoring their priorities.

At the end of the day, buyers are the ones who have to live in the home and make the monthly payment, not the agent.

Another major issue is communication. If an agent takes forever to respond during the home search process, that can become a serious problem, especially in a competitive market like Philadelphia where properties move quickly. A delayed response can absolutely cost a buyer an opportunity.

Sellers

One of the biggest mistakes sellers make is hiring the agent who tells them exactly what they want to hear.

Sometimes a seller wants a price that simply is not supported by the comparable sales, and instead of having an honest conversation, the agent agrees to it just to secure the listing.

That usually ends the same way. The property sits on the market, the listing becomes stale, price reductions start happening, and sellers end up frustrated.

I believe it’s better for an agent to be honest upfront rather than overpromise and underdeliver later.

Communication is another huge factor. Sellers should work with an agent who keeps them informed, responds in a timely manner, and stays actively involved throughout the process. A home sale can already be stressful enough. Poor communication only makes it worse.

3. What Questions Do I Wish More Clients Would Ask Before Hiring an Agent?

The number one question I wish more clients would ask me is: “Vinny, will you please represent me in this transaction?” Lol.

But in all seriousness, I wish more buyers and sellers would ask agents how they handle problems once a transaction starts going sideways.

Almost every real estate deal looks smooth in the beginning. The real test comes once inspections happen, appraisals come in low, financing gets delayed, negotiations get contentious, or unexpected issues pop up during the transaction.

That’s where communication, problem solving, negotiation skills, and experience actually matter.

Anybody can unlock a door and send listings from the MLS. What separates good agents from average ones is how they perform when things stop going according to plan.

I think consumers should spend less time focusing on social media followers, team size, or flashy marketing, and more time asking agents how they operate when a deal gets difficult. That’s usually where the difference between a smooth transaction and a disaster shows up.

4. What Questions Are Overrated or Don’t Actually Tell You if an Agent Is Good?

One question that I think is completely overrated is: “Do you work nights and weekends?”

Of course I do. Time is of the essence in real estate. Homes hit the market at all hours, offers have deadlines, inspections happen during the work week, and negotiations can change quickly. If an agent tells you they don’t work nights or weekends, honestly, run for the hills.

Another one is: “Is there anything wrong with this house?”

Over the years, I’ve gotten much better at spotting potential issues when walking through properties. I’ll absolutely point out things that catch my attention. But at the end of the day, that’s exactly why home inspections exist.

No agent, no matter how experienced, can fully diagnose a property during a 20-minute showing. Buyers should want honesty from their agent, not fake certainty.

I also think people put way too much emphasis on asking: “How long have you been in the business?”

Time in the business does not automatically equal skill, production, or competence.

If an agent has been licensed for 20 years but only closes a handful of transactions each year, does that automatically make them a better choice than an agent who’s been licensed for four years but handled 30 transactions last year? I don’t think so.

I think consumers should focus less on years in the business and more on things like communication, problem solving, negotiation skills, local market knowledge, and how actively an agent is working in today’s market.

5. How Do You Personally Handle Communication With Clients?

One of the first questions I ask every client is: “What is your preferred method of communication?”

Personally, I prefer email because it keeps things organized and documented. But not every client likes email. Some prefer texting. Some prefer phone calls. Others want a mix of all three.

At the end of the day, my job is to communicate in the way that works best for the client, not just what works best for me.

I take communication very seriously and make it a point to keep clients updated throughout the entire transaction. Whether it’s a showing update, inspection issue, appraisal update, financing delay, or just a quick check-in, I don’t like clients feeling left in the dark.

That said, sometimes a phone call is simply the best option. A five-minute conversation can solve problems much faster than going back and forth over long texts or emails all day.

In terms of response time, I typically respond to clients within an hour whenever possible. Even if I’m tied up with appointments, negotiations, inspections, or another client, I’ll usually send a quick acknowledgment letting them know I saw their message and will get back to them as soon as I can. I don’t like leaving people hanging.

I also tell clients that they can reach out to me whenever they have availability, whether that’s during the day, at night, or on weekends. Real estate doesn’t really operate on a perfect 9-to-5 schedule. Of course, that doesn’t always mean I can respond immediately at 1 AM, but I want clients to feel comfortable reaching out when they need something.

I also believe in setting realistic expectations upfront. If I’m going on vacation, attending an important event, or know my response time may be slightly delayed for any reason, I communicate that ahead of time so nobody feels ignored or surprised.

6. What Makes Your Approach Different From the Average Philly Realtor?

I think a lot of agents are good when everything is going smoothly. Where I separate myself is when a transaction becomes difficult.

Inspections go sideways. Appraisals come in low. Financing gets delayed. Negotiations get heated. Sellers get emotional. Buyers get nervous. That’s where I think communication, problem solving, and experience actually matter.

I also don’t believe my job is to pressure people into buying or selling a house just so I can collect a commission check. My job is to advise clients, protect them, communicate with them, and help them make smart decisions.

Another difference is that when clients hire me, they’re actually working with me. They’re not getting handed off to an assistant or bounced around a massive team after signing paperwork.

I’m also honest with clients, even when it’s not what they want to hear. If I think a property is overpriced, a deal doesn’t make sense, or expectations are unrealistic, I’m going to say it.

Communication is another big thing for me. I adapt to how each client prefers to communicate, whether that’s text, phone calls, or email, and I make it a point to keep people updated throughout the process. I don’t like clients feeling left in the dark.

Lastly, I’ve been doing this long enough to know that not every client-agent relationship is the right fit, and that’s okay. I’m not trying to work with every single person. I want to work with people who value honesty, communication, strategy, and having someone in their corner when things get tough.

7. What Types of Clients or Transactions Are You Especially Good At Handling?

I think I’m especially good at working with first-time home buyers.

For most people, buying a home is one of the biggest financial decisions they’ll ever make, and I do not take that responsibility lightly. A lot of first-time buyers are overwhelmed, nervous, and unsure of what to expect, which is completely normal.

I pride myself on being patient, answering questions thoroughly, and walking clients through the process step by step so they actually understand what’s happening instead of feeling lost the entire time.

On the seller side, I think I’m very good at analyzing offers and helping clients separate the strong deals from the weak ones.

Not every offer is as good as it looks on paper. Sometimes there are financing concerns, unrealistic contingencies, buyer agents overpromising, or terms that can create problems later in the transaction. I think I’ve gotten very good at identifying potential red flags early and helping sellers understand whether an offer is truly solid or not.

At the end of the day, I try to approach every transaction strategically instead of emotionally.

8. What’s Your Honest Opinion on Part-Time Agents, Mega Teams, Discount Brokers, and Agents Who Mainly Buy Leads Online?

Part-Time Agents

I think it’s absolutely possible to be a part-time real estate agent. That said, real estate does not sleep.

You can absolutely work a full-time job and still do real estate on nights and weekends. But you also need to be prepared for the reality of the business. Inspections get negotiated on Tuesday afternoons. Multiple offers come in on Thursday mornings. Problems happen during normal business hours.

So while it can be done successfully, clients should understand that availability and responsiveness matter a lot in this business.

Mega Teams

Mega teams can be great, and they can also not be great. I actually started my career on a large real estate team, and I’ll never deny how much it helped me early on.

The team provided leads, mentorship, administrative support, and camaraderie with other agents. It gave me a strong foundation and helped accelerate my career.

Over time, though, the team continued growing and I personally started feeling more like a number than an actual team member. The one-on-one mentorship and direct access to leadership slowly started disappearing, and I realized I wanted more control over my business and my client experience.

That’s ultimately why I went solo.

At the end of the day, some people thrive on teams and others don’t. It really depends on personality, business goals, and how entrepreneurial the agent wants to be.

Discount Brokers

In life, you usually get what you pay for.

If someone chooses to work with a discount broker, they should also expect the possibility of discounted service, reduced communication, or less involvement throughout the transaction.

That doesn’t mean every discount broker is bad. But consumers should understand that there is usually a reason why the service is being offered at a discount.

Agents Who Mainly Buy Online Leads

I have no issue with agents buying online leads.

At the end of the day, real estate agents are independent contractors running their own businesses. In business, sometimes you have to spend money to make money.

The important thing is understanding the true cost of those leads. For example, some platforms like Zillow can take a large percentage of an agent’s commission in exchange for the lead. That’s a major business expense.

At the same time, one online lead could turn into repeat business or multiple referrals down the road. In real estate, referrals are everything.

I think consumers should care less about where the lead came from and more about whether the agent is competent, communicative, and actually good at their job.

9. Give Me 1-2 Examples Where You Told a Client Something They Didn’t Want to Hear, But It Was the Right Advice

Example #1: Being Transparent About a Home Inspection Report

I listed a property for a seller in the West Oak Lane section of Philadelphia. We went under contract, the buyer completed a home inspection, and ultimately decided to terminate the deal.

The interesting part was that there really wasn’t anything major wrong with the house. Most of the inspection items were minor and fairly typical.

In Pennsylvania, though, if a buyer wants to terminate during inspections, they usually need to provide the inspection report, which they did. At that point, I advised my seller that we should make the inspection report available to future buyers.

He strongly disagreed with me.

His position was that the report was just one inspector’s opinion and that future buyers should conduct their own inspections instead of relying on someone else’s report. I understood where he was coming from, but I explained that withholding the report could actually hurt us in the long run.

My advice was that it’s better to be transparent upfront. If future buyers can review the report before making an offer, they can factor those items into their decision-making process from the beginning rather than backing out later.

Eventually, I convinced him to make the report available, which I believe was the right move both strategically and ethically.

Example #2: Telling Friends Their House Was Overpriced

I had sellers who were also friends of mine, and they wanted to list their property significantly higher than what the market data supported.

I told them upfront that if we listed the property at that price, we likely wouldn’t get much activity. Very few showings. Very few offers. Unfortunately, that’s exactly what happened.

Six months went by with almost no traction.

At that point, we had a more serious conversation. I presented comparable sales, market data, and explained why buyers simply were not responding to the pricing.

Naturally, the conversation became a little contentious because emotions get involved when it’s your own home, especially when friends are involved too.

Instead of continuing to argue opinions, I suggested bringing in an independent appraiser to determine the property’s market value objectively.

The appraisal ultimately came back roughly $33,000 lower than the list price they originally wanted.

Once they saw the appraisal, we adjusted the pricing accordingly, and shortly after that, the property started generating showings and offers.

One thing I’ve learned in real estate is that honesty is not always comfortable in the moment, but it usually leads to better outcomes long term.

10. What Should Someone Feel After the First Conversation With a Real Estate Agent if That Agent Is Actually Competent?

You should feel confident.

Confident that the agent understands the process, knows what they’re talking about, communicates clearly, and can actually get the job done.

Whether you’re buying a house, selling a house, investing in a property, purchasing land, or dealing with a more complicated situation, you should walk away from that first conversation feeling like the agent has a plan and knows how to guide you through the process.

That doesn’t mean they should pretend every transaction is going to be easy or problem-free. Real estate can absolutely get complicated at times.

But a competent agent should make you feel like no matter what challenges come up, they’ll be able to navigate them, communicate through them, and help you get to the finish line.

Final Thoughts

Choosing a real estate agent is a much bigger decision than most people realize.

The right agent can help protect your money, reduce stress, solve problems, negotiate effectively, and guide you through one of the biggest financial decisions of your life.

The wrong agent can create confusion, poor communication, bad advice, unnecessary stress, and costly mistakes.

My advice is simple: don’t just hire the agent with the biggest social media following, the flashiest marketing, or the highest promised price.

Hire the person you trust to communicate honestly, solve problems when things get difficult, and protect your best interests throughout the transaction.

If you’re thinking about buying, selling, or investing in Philadelphia real estate and want to have a conversation, feel free to reach out.

— Vinny Fracassi aka South Philly Vinny

South Philly Team