What to Look for When Choosing a Portland Real Estate Agent

I've closed over 80 transactions, and the thing I've learned is that successful deals have less to do with perfect pricing strategy and more to do with relationships — specifically, the relationship between the two agents working either side of the transaction.

Think about what's actually happening. You've got a buyer and a seller who probably don't know each other, negotiating one of the biggest financial decisions of their lives, entirely through two intermediaries. Every offer, counteroffer, inspection response, repair request, and timeline conversation flows through the agents. When both agents are collaborative and focused on getting to a good outcome, deals move — even through tough negotiations, even when things get complicated. When that dynamic is missing, an already stressful process gets significantly harder.

That's why who you hire matters more than most people realize going in.

Read the reviews — but read for how they handle difficulty

Five stars is a starting point. What tells you more is the actual text. Look for reviews where a client describes a moment something went wrong and their agent handled it well — where they felt informed, advocated for, and told the truth even when the news wasn't great.

"She was so nice and easy to work with" is good, but it doesn't tell you how someone performs when an inspection comes back ugly or the other side pushes back hard. The real estate agent reviews that tell a real story are worth far more than the ones that just hand out a gold star.

Also check recency. A strong review history that stops two years ago is worth noting. You want someone who's actively working and actively earning good feedback right now.

Look at their recent transaction activity

How many homes has this agent closed in the last year? In what neighborhoods? At what price points? You can often find this on Zillow or Realtor.com — most agent profiles show recent sales. You're not necessarily looking for the highest volume, but you are looking for relevance. If you're buying in Sellwood or looking in the $600k range in Beaverton, you want an agent who has worked in those areas at that price point recently.

Volume also signals how present someone is in the market. Low transaction activity isn't automatically a dealbreaker, but it does mean they may not have the current feel that comes from being in it week after week — knowing what's moving, what's sitting, and what offers are actually winning right now.

Ask how they communicate — and watch how they answer

This is one of the most revealing questions you can ask in a first conversation. An agent who says "I send a weekly update every Friday and I'm always reachable by text" is giving you a real, specific answer. An agent who just says "I'm very communicative" is not giving you much.

How your agent communicates with you determines how informed and calm you feel throughout the process. How they communicate with the other agent affects how smoothly the deal moves. You want someone who's clear, timely, and professional — not just with you, but with everyone involved.

Ask them to walk you through a transaction that got complicated

Every agent who's been doing this for more than a year has at least one. What you're listening for isn't a perfect outcome — sometimes deals fall apart and that's nobody's fault. You're listening for how they handled it. Did they stay calm? Keep their client informed? Work through the problem collaboratively, or let things get adversarial?

An agent who can tell you a real story with real texture, and reflect honestly on what happened, has done the work. Someone who can't think of a complicated transaction — or gives you a very polished, vague answer — may not have been through enough yet to know how they perform under pressure.

Ask how they approach working with the agent on the other side

Most people never think to ask this, and I think it's the most important question on the list.

What you want to hear is something that reflects a collaborative mindset — building rapport with the other agent, keeping communication open, looking for solutions that work for both sides. That philosophy is what gets deals done. It's not about rolling over; you're still advocating hard for your client. But there's a real difference between advocating firmly and creating unnecessary friction, and a good agent knows it.

If you get a lot of "I fight hard for my clients" language with zero acknowledgment of relationship-building, pay attention to that. The us-versus-them mentality can actually work against you, because at the end of the day, you need the other side to say yes — and they're less likely to do that when they feel like they're being put on the defensive.

The agents who are right for you will hold up under all five of these. They'll have real answers, not rehearsed ones, and honestly, they'll probably be glad you asked.