Helping Hospitality and Tourism Businesses Reduce Guest Hesitation

Most independent hospitality businesses don’t struggle because people stop wanting to travel.
They struggle because guests hesitate.

A guest arrives, pauses just short of the front desk, and checks their phone instead of asking a question.
A traveler opens a few tabs, likes all the options, and tells themselves they’ll decide later.
A couple stands outside a restaurant, reads the menu twice, looks down the street, and keeps walking.

That pause adds up.

When interest is there but bookings stall, hesitation is usually what’s in the way.

What I focus on is making decisions feel clearer and easier — before booking, at arrival, and when guests decide what to do next — using simple systems and practical AI that support how hospitality actually works.

When hesitation sticks around, even well-run businesses slow down.

What This Work Is Built On

Trust as Strategy

Guests don’t act when they’re convinced. They act when things feel safe. Trust shows up in clear information, consistent signals, and fewer moments of second-guessing as people choose, arrive, and settle in.

Systems Over Hustle

Good hospitality doesn’t come from doing more. It comes from fewer things breaking. Simple rhythms and repeatable workflows make days calmer, arrivals smoother, and the same issues stop showing up again and again.

AI as Infrastructure, Not Gimmick

AI works best when it takes pressure off. Used well, it helps responses arrive faster, messages sound more human, and personalization stay consistent — without draining your team.

Start Here

If this resonates, subscribe and read along.

Each week, I share one clear insight that helps you see where hesitation shows up in your guest journey, what’s causing it, and what to fix first — so you can stop guessing and focus on what actually moves decisions.

Who’s Behind It

Hi. I’m Kay Walten.
Founder of Smart Pineapple.

I’ve spent more than 35 years in hospitality, running boutique vacation rentals, building an early online reservation platform, and working alongside hotels, restaurants, and destinations that feel overshadowed by bigger brands and bigger budgets.

After seeing the same hesitation show up across different places, seasons, and business models, I stopped believing this was an effort problem. Most of the time, it’s a clarity problem.

That’s the work I do here.

Kay Walten’s and Smart Pineapple’s Affiliations