Happy Monday!

I’m writing this from Seattle after what can only be described as a very full week…

I was here for a Rent Responsibly retreat… AND… just before that, I spent time in a hospital welcoming our newest grandchild into the world. ❤️

Big. Week.

And somewhere between navigating hospital hallways, airports, and STR advocacy sessions, I had the same thought more than once:

There are places where everyone else just knows how things work… and you don’t.

You don’t know where to stand.
What to say.
What’s expected.
What’s normal.

And even if everyone is perfectly nice… you still feel like you’re one wrong move away from an eye roll.

We’ve all been there.
(Or… someone we know has )

But here’s the thing…

We’ve created that exact same dynamic in our STR world.

We have our own little ecosystem:

• Unwritten rules
• “Obvious” expectations
• Systems that make total sense… once you know them

And for a guest walking into your property?

They’re the new kid.

So the real question is:

What are we doing to help them feel like a pro from the moment they walk in?

Here are a few of my favorite ways to make guests feel like an insider rather thank of an awkward goof ball:

1. Create quick wins early
An easy check-in. A welcome note. A small thoughtful touch.
Nothing builds confidence like getting something right in the first 10 minutes.

2. Normalize the “first time” experience
Say things like, “Most guests find this helpful…” or “Here’s how this works…”
You’re giving them permission to not know—and helping them feel smart anyway.

3. Anticipate the awkward moments
Parking. Trash. Noise. Check-out.
The things that cause the most friction are the ones that feel unclear.
Clarity removes stress (for them and your neighbors).

4. Spell it out (like you would for your mom)
If there’s a trick to the lock, the thermostat, the coffee maker… it’s not intuitive.
Clear, simple instructions = instant confidence.

5. Make it easy to ask for help
If they feel like reaching out is a burden, they won’t… until it’s a problem.
A simple, “Text me anytime—we’re happy to help” goes a long way.

Because at the end of the day…

Great STR operators don’t just provide a place to stay.
They make people feel like they belong there.

Like they “get it.”
Like they’re in the know.
Like they’re… dare I say… the cool kid.

And if you can do that?

You don’t just avoid problems.
You create better experiences, better reviews, and better relationships with your guests and your community.

PS: A very Happy Mother’s Day to all the moms in our community.
And a very special one to my amazing daughter-in-law celebrating her first.

Welcome to the club… you’re already a pro.