Step 1: How did they get into short term rental property management?

I would want to find someone who started out either working for another full service management company and then went out on their own or who got their start with their own short term rentals. There should be some passion in their voice for hospitality.

Step 2: What does their team look like?

At the very least I would be looking for someone who has at least two options for cleaning, a laundromat they’re partnered with for linens, and a trusted handyman. If they don’t have solid understanding of the financials, I’d make sure their bookkeeper / accountant did.

Step 3: What is the current scale and operating region of their business?

This is THE MOST IMPORTANT question. I would be looking for someone who rents between ten and fifty homes. Once they get to ten they will have some systems in place. Beyond fifty, unless they are running a really tight operation, the personality of running a local business will start to wear off. Guest communication will wander towards impersonal and owner communication will become bumpy at best. More important than their listing count, I would be really focused on their operating radius. Are they hyper focused on one market, or are their listings scattered across multiple markets. Focusing on one market has an incredible amount of advantages. Cleaner gets sick? Just slide in another. Guest having trouble with a lock? Good thing it’s only fifteen minutes away. This list goes on and on. Look for someone close by and laser focused on a SINGLE MARKETPLACE.

Step 4: Ask ONE technical question

The problem with asking too many technical questions is that you aren’t going to know if the answer is good or not. For example, asking a potential property manager about their minimum night stay strategy won’t be that effective because you’re hiring them because you don’t know how to build out an effective minimum night strategy. Choose an operations system that you can research, get really clear on what the best way to handle this sort of operational challenge is, and focus on that one topic. A few examples below.

- What is your nightly minimum strategy and WHY?

- What is your system for a guest that wants to check in early / check out late?

- Do you screen guests? If so, how?

- What is your system for handling all the financials and how do you make that transparent to your clients ?

Step 5: How does their feedback look?

Last but not least, how do their testimonials and guest reviews look? Anyone managing a few properties should have a significant amount of reviews to show through AirBnb / VRBO etc. In addition, I would be looking for at least 25% of their clients to have written them reviews on their google business site or personal letters. I’m not calling references, it’s too staged. They should be able to produce these testimonials on the spot. If they don’t have them, I’m looking elsewhere.