The Question You Answer Five Times a Day
A Workflow for Eliminating Repeat Guest Questions
Time required: 15 minutes to identify, 1 hour to fix
Who runs it: Owner, manager, host, or property operator
Property types: Hotels, B&Bs, vacation rentals, short-term rentals, boutique properties
The Core Idea
Every repeat question lands in the first 15 minutes—the arrival window where guests are still deciding whether this place was ready for them.
Every repeat question is friction. Every question guests have to ask is a signal something isn’t clear.
This workflow finds your most frequent question and eliminates it. Then you do it again next month.
One question. One fix. Verified. Repeated.
What this is not: More tools, software, or longer guest messages. This is about removing the questions that never should have existed.
If You’re Running This With a Team
Frame it as: “You’re absorbing friction that guests shouldn’t be creating.”
Part 1: Gather the List
If you have on-site staff: Ask them: “What question do guests ask you most often—something you answer at least once a shift?” Write down every answer.
If you manage remotely: Pull up your guest messages from the last 30 days. Scan for questions that repeat across OTA threads, your PMS inbox, and texts.
If you’re solo: Keep a tally for one week. Every repeat question gets a mark.
Part 2: Score and Pick
For each question, score three factors:
Add the scores. Pick the highest-scoring question you can fix this week.
If two tie, pick the one that happens at arrival. Arrival friction costs trust.
Part 3: Diagnose the Gap
Before you fix it, understand why the question exists.
The physical test: Stand where a guest would stand when they’d ask this question. Is the answer visible? If managing remotely, walk through your messages in order.
Common failures:
Part 4: Design the Fix
Access Questions
“How do I get in?” / “What’s the code?” / “Which entrance?”
Fix: Pre-arrival message with photo + code, timed for arrival. Mark the door if it’s not obvious.
Test: Can they get in at 11pm, in the dark, without messaging you?
Orientation Questions
“What’s the WiFi?” / “How do I work the TV?” / “Where’s the ice machine?”
Fix: Information at the point of use, not the point of entry.
Test: Can they find it without searching, scrolling, or opening an app?
Logistics Questions
“What time is checkout?” / “Do I need to do anything before I leave?”
Fix: Confirmation message AND check-in message. Bolded. Near the top.
Test: Can you find checkout time in under 5 seconds?
Parking Questions
“Where do I park?” / “Is it free?” / “How many spots?”
Fix: Pre-arrival message with photo of the exact spot or lot.
Test: Can they park without circling or messaging you?
Area Questions
“Where should we eat?” / “Is the trail open?”
Fix: Three curated picks with one line each. Keep it current or remove it.
Test: Is every recommendation open this week?
Part 5: Implement
Signage: Fewer than 10 words. At the decision point, not after. Readable from 6 feet.
Messages: Key info in the first 3 lines. Check every channel—guests may only see one.
Placement: Point of use beats point of entry. If they have to search, it’s wrong.
One fix this week.
Part 6: Verify
One week later:
If you have staff: “Is anyone still getting asked [the question]?”
If remote: Search your messages. How many times did it come up?
If solo: Run your tally again. Compare.
Part 7: Repeat Monthly
Attach this to something you already do—listing review, staff meeting, property walk.
The monthly question:
“What question am I answering most often right now?”
One question. One fix. Verified. Repeated.
What About Questions You Can’t Fix?
Some frequent questions have no cheap fix. “Why is the WiFi slow?” “Why is parking so far?”
You can’t eliminate them. You can prevent them from becoming complaints.
Acknowledge proactively: Name it before they experience it. - “Fair warning: WiFi is solid for streaming but not ideal for video calls.”
Reframe the tradeoff: Help them see what they’re getting. - “No elevator—but original hardwood and 12-foot ceilings in a building from 1920.”
Offer a workaround: Give them an option. - “Need fast internet? There’s a coworking space 10 minutes away.”
Proactive acknowledgment doesn’t fix the problem. It prevents the question from becoming a complaint.
Quick Reference: Fix Matrix
The One Thing
What question do guests ask most often?
Write it down. Fix the top one this week. Verify it worked.
Then ask again next month.
Questions or want help running this? Message me.
Part of the Smart Pineapple operational series, building on arrival readiness and the 90-second reset. Guests who don’t have to ask questions arrive calmer. Operators who don’t answer repeat questions have capacity for what matters.
The scoring matrix is clever but what really stood out was framing these as signals of unclear design rather than just operational load. Ran a small B&B for a bit and the pre-arrival photo trick for parking would've saved so many panicked calls. Most operators never think to test their own instructions at nighttime which is usually when things actully break down.