Why Guests Behave Badly
What’s really happening when ‘good guests’ cause problems.
The Pattern You’re Probably Seeing Now
It’s 11 PM on a Friday. Your phone buzzes.
A guest—polite, well-reviewed, seemingly reasonable—is asking where to park.
You sent the parking instructions three times: booking confirmation, pre-arrival email, pinned check-in message.
Or it’s a neighbor texting about noise. Again.
From guests who seemed great in every interaction.
Or it’s the smaller things that keep stacking up: trash left in the wrong place, checkout steps ignored, house rules that might as well be invisible.
Here’s the realization many operators are coming to:
These aren’t bad guests.
They’re good people operating with missing context.
I’m seeing this pattern across regions and property types.
And it has a cost.
What’s Actually Going On
Hospitality didn’t suddenly get harder because guests got worse.
It got harder because the systems shaping guest behavior changed.
Over the past few years, operators adopted real efficiency gains:
Automated guest messaging
Contactless check-in as the default
AI-powered pricing, messaging, and operations
Those systems help you scale.
But they also quietly removed something else:
Human orientation
Informal guidance
Context about “how this place works”
Guest behavior didn’t fundamentally change.
Your leverage over outcomes did.
When orientation disappears, friction doesn’t look dramatic at first.
It looks like:
More late-night texts
More “unfair” reviews
More neighbor complaints
More emotional energy spent fixing things that shouldn’t need fixing
That friction compounds every stay.
The Problem Isn’t What You Think
You don’t manage guest behavior.
You design the conditions that shape it.
When expectations are framed clearly and early, guests regulate themselves.
When they’re not, you pay the tax later:
Support tickets
Conflict resolution
Reputation management
Eventually, regulation
Orientation isn’t about being nice.
It’s about maintaining control of outcomes.
Where Automation Starts to Break Down
Automation and AI adoption across hospitality is accelerating fast:
Guest messaging
Dynamic pricing
Operations coordination
The upside is speed and consistency.
The hidden cost is tone.
When automation carries all communication, the cues that quietly teach guests how to behave disappear.
Same Info. Very Different Outcome.
Before (human-framed):
“Hey Sarah! Just a heads-up — our building is in a quiet residential neighborhood. Sound carries more than most guests expect after 9 PM, and neighbors have lived here for decades. If you’re planning an evening hangout, the rooftop works much better. We’re really looking forward to hosting you!”
After (automation-optimized):
“Check-in is at 3 PM. Quiet hours begin at 9 PM. Violations may result in additional fees.”
Same facts.
Very different downstream cost.
One message prevents issues.
The other manages consequences.
When Local Pushback Begins
This pattern doesn’t stop at individual properties.
When friction accumulates at scale, it becomes a public problem.
In parts of Europe, cities in Italy restricted hands-off self-check-in systems; Spain introduced a national short-term rental registry in 2025 to tighten oversight.
In the U.S., cities like Austin revisited STR rules, enforcement, and accountability — not just volume, but impact and behavior.
Globally, organizations tracking STR regulation report a steady rise in new laws and enforcement mechanisms.
Regulation doesn’t show up first.
It shows up after systems fail to shape behavior consistently.
When that happens, operators lose flexibility — and flexibility is leverage.
This Isn’t a Guest Problem
Guests aren’t ignoring instructions.
They’re navigating unfamiliar environments with incomplete context, under stress.
Rules without explanation feel arbitrary.
Instructions without tone feel punitive.
Policies without context feel bureaucratic.
That misunderstanding shows up later as:
Noise complaints
Parking issues
Reviews you feel you didn’t deserve
Strained relationships with neighbors
Not because guests don’t care —
but because the system didn’t help them succeed.
AI - Where it Helps, and It Hurts
Automation isn’t the villain.
But it isn’t neutral.
✅ Where AI Actually Helps
Access details
Directions and FAQs
Scheduling and reminders
This reduces error in high-volume situations.
⚠️ Where AI Gets in the Way
Fully automated pre-arrival messaging
Fully automated expectation-setting
Fully automated tone
What disappears isn’t information.
It’s self-regulation.
AI should carry logistics.
Humans should frame expectations.
One Small Fix That Pays Off
Don’t overhaul your operation.
Fix one message.
Start With Your First Pre-Arrival Email
This message quietly trained your guests how to behave. Whether you meant it to or not.
You’re not rewriting rules.
You’re restoring leverage.
Ask:
Does it explain what kind of place this is?
❌ “Check-in is between 3–6 PM.”
✅ “You’re staying in a 1920s brownstone with original hardwood floors — beautiful, but sound carries more than in newer buildings.”
Does it explain why behaviors matter here?
❌ “No parties allowed.”
✅ “This is a residential building where families have lived for decades. Quiet after 9 PM helps everyone enjoy the space.”
Does it sound like a welcome, not a warning?
❌ “Violations may result in additional charges.”
✅ “We want you to feel at home here. Understanding a few quirks of the space makes the stay smoother for everyone.”
Fix this once.
It pays you back every stay after.
Try This Prompt
Copy and paste this into your favorite AI, and add your own info.
I’m rewriting our pre-arrival message for [property type] guests.
The property is [describe the space and quirks].
It’s located in [describe neighborhood character].
Our typical guests are [describe guest profile].The main issues we see are:
[list 2–3 recurring problems]
Rewrite the message to welcome guests warmly, explain the personality of the space, give context for our three most important expectations, and make guests feel excited—not anxious—about their stay.
What This Changes
Behavior is an outcome, not a trait.
Orientation is a system, not a courtesy.
When guests understand where they are and why things work the way they do, friction drops, reviews stabilize, and trust compounds.
This isn’t an AI problem.
It’s a leverage problem.
Technology can support leverage.
It can’t replace it.
What patterns are you seeing with guest behavior and systems?
Let me know in the comments. I read every response.
I’m spending the next few weeks talking with operators about recent guest communication challenges, especially around automation and where things break down in real life. I’m exploring a course idea and want to pressure-test it against actual experiences, not assumptions.
If you’ve dealt with this recently and are open to a short conversation, hit reply, or message me, let me know. No pitch — just listening.