It's the third week of June, and the person you hired for the season is doing fine. Friendly, quick, eager to get it right. Then the phone rings during check-in, and the caller wants to know if the dog's allowed, where to leave the car, and whether the last boat still goes out at four. Your new hire covers the receiver and glances around the room for someone who's done a few summers here.
That little pause is the whole problem. The answers exist. They're just in the heads of the people who've worked here long enough to know them cold, and those people are busy, or off, or three tables deep in the dining room.
Closing that gap before July doesn't mean turning anyone into a script reader. The trick is to write down what you already say out loud fifty times a week, put it somewhere a week-one hire can reach in a second, and let a bit of AI do the finding. Done right, the new voice on the phone sounds like it's been here for years.
Start with the questions you already answer
You don't need to imagine what guests will ask. You already know, because you've answered the same handful of questions every day since you opened. Parking. Dogs. Check-in time. Whether the kitchen's still serving. What the tide's doing. How far to the beach.
Spend one slow morning listing them. Better yet, ask the people who work the phone to jot down every question they field for three days. You'll end up with forty or fifty, and maybe a dozen that come up again and again.
Those repeat questions are your answer sheet. Write each one with the answer a veteran would give, in the words you'd actually use:
- Parking: where, how many spots, what to do when the lot's full.
- Dogs: yes or no, which rooms, any fee, leashed on the porch.
- Hours today: not the sign in the window, the real hours for this week.
- Getting here: the turn people miss, the lot that fills early, the walk from town.
- The thing only locals know: tide times for the flats, where the sunset's best, which night the band plays.
Keep the answers short and plain. A new hire reading one back should sound like a person, not a policy manual.
Build one answer sheet the AI can search
Here's where a little AI earns its keep. Take that list of questions and answers and load it into an assistant, which is just a chat tool set up to pull from your document instead of making things up. Your hire types "can they bring the dog," and it hands back your exact answer, not a guess it found on the internet.
The point isn't fancy. It's speed and sameness. A ten-summer veteran and a week-one hire give the same reply, because they're both reading from the same sheet. Set it up so it only answers from what you loaded, and it won't invent a pet policy you never wrote.
- Put every question and answer in one plain document. One question, one answer, a blank line between.
- Load it into an assistant that reads from your file. Plenty of these exist now, often for under a hundred a month.
- Test it with your own tricky questions before you hand it to anyone.
- Set it on the device at the desk, and on the phones your crew carries around.
Once it's running, it runs quiet in the background, which is about the best you can ask of any tool during a busy season.
Keep it current as the season shifts
A sheet that's right in June and wrong in September is worse than no sheet, because now the new voice sounds confident and mistaken. Coastal hours don't sit still. The kitchen closes earlier after Labor Day, the four o'clock boat becomes a three o'clock, and the shoulder-season quiet changes what's even open on a Tuesday.
Give one person the job of updating the sheet, and give them a rhythm. Every Sunday night, or every time the hours change, whichever comes first. It's a five-minute edit, not a project.
- Update hours and last-call times the day they change, not the week after.
- Add the questions that stumped someone this week. Every new one makes the next hire sharper.
- Cut anything that's no longer true: old specials, a closed room, the boat that isn't running.
Specials are the part that goes stale fastest, so keep the daily catch or the weekend menu in its own short note the kitchen updates, rather than burying it in the main sheet where nobody remembers to fix it.
Know where a human still has to take over
An answer sheet is great at questions with one right answer. It's no good at judgment, and you shouldn't ask it to be. The caller who's upset, the guest who wants to move a booking around a storm, the family asking you to bend a rule for a good reason: those need a person.
Teach your hires the line, and it's a simple one. If the question has a fact for an answer, use the sheet. If it needs a decision, a favor, or a soft touch, take a name and number and get the right person on it.
- Hand it off: complaints, refunds, special requests, anything involving money or an exception.
- Handle it: hours, directions, policies, the tide, the small stuff that fills the day.
Nobody minds hearing "let me have the owner call you right back." What loses trust is a confident wrong answer, and that's exactly what the sheet is there to prevent.
Worth doing this week
You don't need the whole thing built by Friday. A few small steps get you most of the way there:
- Ask whoever works the phone to write down every question they get for three days.
- Pick the fifteen that repeat, and write the answer you'd want a guest to actually hear.
- Put them in one document and load it into an assistant that answers only from your file.
- Test it with the questions that usually trip people up, then set it on the desk.
- Name one person to keep it current, and pick the night they sit down and do it.
Do that much, and the person who started in June answers like they've weathered ten summers here. If wiring it up yourself isn't how you want to spend a June week, that's the kind of setup we put in place for Massachusetts businesses.