Most Guest Problems Start Before Arrival
Fix One Message. Change the Whole Stay.
Most guest problems don’t start when someone parks in the wrong spot or leaves the trash outside the wrong door.
They start three days earlier, when your first arrival message hits their inbox and gives them instructions but not orientation.
You think you sent clarity.
They think you sent rules.
The gap between those two things?
That’s where most of your problems live.
And yes, across STRs, boutique hotels, cabins, and lodges…
I’m seeing the same pattern everywhere.
Before we get into the workflow, here’s the truth operators forget:
You’re guiding the stay before they ever walk through the door. Once guests understand how things work, everything runs easier for them and for you.
This workflow shows you how to rewrite one message and reduce most of the friction that normally shows up on arrival day.
Let’s get into it.
Why This Matters (and When It Actually Helps)
This workflow pays off most during:
Holiday weekends
Guests are distracted, traveling with family, making decisions in parking lots.Peak season
You’re juggling turnovers. They’re juggling logistics.Event weekends (concerts, football, festivals)
Everyone is in a hurry, everyone is tired.Late check-ins
Guests skim, misread, and assume.Self check-in / reduced staffing
No human touchpoint to course-correct early mistakes.
Across property types, here’s how it shows up:
STRs / Vacation Rentals
Parking confusion
Noise misunderstandings with neighbors
Guests using the wrong entry
Misreading house quirks
Boutique Hotels
Guests expecting apartment-style freedom
Early/late arrivals misaligned with staffing
Misunderstanding building layout
Noise complaints due to thin walls or older construction
Cabins, Lodges, Rural Properties
Guests arriving after dark and missing signage
Poor cell reception causing stress
Roads, access points, and safety norms unclear
All of these problems trace back to orientation, not behavior.
So let’s fix the moment where orientation starts.
STEP 1 — Identify Your First Message
This is the message that shapes how guests interpret everything that follows.
Usually it’s:
Sent 3–5 days before arrival
Contains instructions like door codes, parking, access, or property quirks
The first real “human” message after booking confirmation
If your booking platform didn’t send it automatically, but you did?
That’s your framing message.
This is the message we’re fixing.
STEP 2 — Spot the Trust Leak
Read your current version.
Does it sound like:
A list of rules with no explanation
A memo from a property manager
Instructions written for compliance, not understanding
Zero sense of place
No hint that help is available
When the tone is missing, guests fill in the blanks.
And they rarely fill them in your favor.
Here’s what that looks like:
Before — Trust Leak
“Parking is in Spot 12. Do not park in any numbered spots. Towing enforced.”
Guest interpretation:
“This host is rigid. One wrong move and I’m in trouble.”
After — Trust Frame
“You’re in Spot 12 — second row on the left as you enter.
The numbered spots belong to long-term residents, so we keep those clear to maintain good neighbor relationships.
If parking feels confusing when you arrive, just text me. I’m close by.”
Guest interpretation:
“This host understands the space. I know what to do. And I can ask for help.”
Same info.
Very different outcome.
STEP 3 — Use the 4-Part Trust Frame
This is the rewrite formula that drops friction instantly.
1. Welcome with Intention
Not hype. Not “We’re so excited!”
Calm orientation.
Example:
“You’re staying in a restored 1920s brownstone. Original floors, high ceilings, beautiful space, but sound carries more than in modern buildings.”
2. Context of Place
What kind of environment is this?
Not a sales pitch — clarity.
Example:
“This is a four-unit building. You’re above a couple who works night shifts, so mornings are their quiet hours.”
3. Explain Expectations (Don’t Enforce Them)
Give the why, not just the what.
Example:
“We ask guests to use the gravel lot because the paved spaces are for retail tenants who open early. It keeps things running smoothly for everyone.”
4. Reassurance
Guests behave better when they know help exists.
Example:
“If anything feels unclear — parking, the door code, the thermostat — text me anytime.”
This frame moves guests from:
‘Don’t break rules’ → ‘I get how this place works.’
STEP 4 — Use AI to Strengthen Your Message
AI is great at tasks.
You’re great at judgment.
Here’s the split:
✅ Where AI Helps
Drafting clean versions
Smoothing tone
Translating while keeping meaning
Keeping things consistent
⚠️ Where AI Hurts
Removing warmth
Removing context
Replacing your voice with generic hospitality-speak
Defaulting to enforcement language
Try this prompt:
Write your rough draft by hand or voice memo.
Drop it into ChatGPT:
Rewrite this message in a calm, explanatory tone.
Keep every piece of “why” context.
Remove anything that sounds like rule enforcement.
Preserve warmth and clarity.
STEP 5 — Rewrite One Message This Week
Don’t overhaul your whole communication stack.
Just fix this one message.
The Action
Choose your first framing message.
Rewrite it using the 4-Part Trust Frame.
The Metric
Before you rewrite:
Count how many “Where is…?” “How do I…?” “Your instructions weren’t clear.” messages arrive in the first 24 hours of each stay.
After rewriting, count again for the next 5 bookings.
If confusion drops?
Your message is doing its job.
If it doesn’t?
You may need to give guests a little more information or make the message feel less like a rule sheet.
STEP 6 — Refresh Before Big Moments
Revisit your first message:
Before holidays
Before peaks
After 3+ friction stays
After adding any new rule (which is a red flag in itself)
Ask:
Does this still explain why things work the way they do?
My “Dos Centavos”
Guests don’t need more instructions.
They need a sense of place.
Rewrite one message.
Transform the stay.
If You Want to Help Me Make This Even Better
I’m spending the next few weeks talking with a small number of operators about guest communication, automation, and where things keep breaking down.
I’m shaping a course concept and want it grounded in real operator experience, not theory.
If you’d be open to chatting, hit reply or send me a message.
No pitch. Just listening.