Dealing with attorneys is part of the job when you own rental property. Whether it’s an eviction, a zoning dispute with a neighbor, or a tenant taking legal action against you, you’re going to end up in a room with a lawyer at some point. And after running my property management company in Philadelphia for years, I’ve learned there’s one small, surefire way to tell if you have a good attorney or a bad one.
Here it is: a good attorney asks the other side for something. A bad attorney never does.
Why This One Signal Tells You Everything
My property management company engages with quite a few attorneys in any given month — for evictions, disputes, all kinds of things. And what I’ve noticed is that the attorneys who never ask for anything from the opposing side are almost always the bad ones.
Think about it. Any legal action is really just a negotiation. You’re trying to advantage your side. Step one of any negotiation is asking for what you want. So when you have an attorney — yours or the opposing side’s — who is bullying, aggressive, unreasonable, and never simply says, “Here’s what would resolve this,” that attorney is not actually working toward their client’s objective.
What they’re often doing is running up billable hours. The longer the conflict drags on, the more they get paid. A conversation that could be over in five minutes can turn into a legal action that lasts years. I’ve seen it happen over and over.
What a Good Attorney Actually Sounds Like
Good attorneys are relaxed. They’re friendly in the way they talk. Not because they’re pushovers — they’ll ask the hard questions and ask for hard things. But they do it with confidence and a reasonable tone, and they do it early. That’s the key.
Almost immediately, a good attorney will say something like: “Hey, we want to fix this, and here’s how we’d fix it. Mr. Property Management Owner, this is how this goes away.” Or in your case as a landlord: “Mr. Rental Property Owner, this is how this goes away.”
They just ask. Right away. No drama, no theatrics, no six months of aggressive letters. Just a clear ask.
The Attorney Addicted to Drama
On the flip side, if your attorney has not asked the other side for anything to date, you have a problem. You may have an attorney who is:
- Addicted to drama
- Addicted to the feeling of intimidating another human being
- Addicted to conflict itself
- Simply running up their bill
None of that meets your objective. It’s the opposite of meeting your objective. An attorney who escalates instead of resolves is going to cost you way more than they’ll ever save you.
How to Handle It: Give Your Attorney a Directive
If you sense your attorney is escalating instead of resolving, give them a clear directive. Tell them: “I want you to reach out to the other side. I want you to make an offer,” or, “I want you to ask them what they want to resolve this.”
If your attorney refuses to do that, walk away. Find a new attorney. It really is that simple. An attorney who won’t ask on your behalf is not invested in getting you a result.
And if the opposing attorney is the one refusing to ask for anything, you can push back directly: “Hey, this would be a lot easier if you just told me what your side is looking for, instead of dragging this out.”
This Is Business, Not Personal
Here’s the mindset shift that matters most. You might feel wronged by the other party. That happens all the time — it happens to us at our property management company. But rental property is an investment, and you have to make investment decisions.
Like the Godfather says: it’s just business. You’re not making emotional decisions. You’re making business decisions. And your job as a rental property investor is to put more money in your pocket, which often means reducing your liability and getting conflicts resolved quickly instead of dragging them out.
An attorney who escalates is directly working against that goal. An attorney who asks early, asks reasonably, and gets to a resolution is worth their weight in gold.
The Bottom Line
Next time you’re evaluating an attorney — whether you’re hiring one or dealing with one on the other side — watch for the ask. Do they reach out and say what they want? Do they do it early? Do they do it in a reasonable tone?
If yes, you’re probably in good hands. If no, get away from that attorney as fast as you can.
Just a humble Philadelphia property management company owner doing my best to answer your rental property investing questions. As always, happy rental property investing.
