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Your people are your superpower for increasing direct bookings & guest loyalty

Doug Kennedy on how to increase sales by deploying the best technology and keeping people in the process

At a recent VRMA event, one of our long-term KTN clients introduced me to a new member, adding a resounding endorsement something like: “Doug’s company does an amazing job training and coaching our people on reservations sales and guest hospitality.”

I could tell by his expression the new member was not impressed, and he confirmed this by saying, “Oh, well we don’t have any people. We book everything online and contract out all operations.”

At that moment in my head, “Good Doug” and “Bad Doug” had a quick conversation. Bad Doug wanted to say “Good luck with that over the long term …” but Good Doug prevailed, and so I simply said, “Oh, yes, I have heard some companies operate that way.” By the way, the new member’s company was founded in late 2020, right when many pandemic-weary people were discovering vacation rentals as a “thing.”

Surely, there are those who will read this article and want to brag about the financial success they are having with this ‘peopleless’ model, and perhaps some will be able to sustain this over the long term. Yet more and more smart vacation rental managers have been realising that building a business built third-party distribution app creates a shaky foundation, and outsourcing key operations such as maintenance creates inconsistencies and delays.

The best in this business know there’s no booking like a direct booking and are doing all they can to “channel convert” those to book via third-party apps.

Now, this is not to suggest that distributing inventory on sites like Vrbo, Airbnb, and the ever-increasing number of new sites is a bad idea. Rather, the key is to use these channels to acquire new guests and then make your brand stick.

I have long said that those in the vacation rental lodging space should be fighting to educate the public on the difference between professionally managed experiences versus taking your chances renting from a random owner posting on a platform. 

Industry leaders should rally to this cause with just as much energy as they have rallied to fight unreasonable local regulations. Countless times when I’ve asked random, vacation-bound passengers on airplanes who they are renting from and heard, “We are staying with Airbnb.” I’m very tired of trying to explain just what a professional vacation rental company is and does differently.

So for those enlightened vacation rental leaders who are still reading 400 words into this article, the following are some actionable suggestions from our on-site KTN training that can be summed up by saying: “Continuously embrace the very best in technology, but deploy it in a way that keeps the people-parts in all processes.”


Post your phone number prominently on your website on both desktop and mobile versions.

Add copy right next to the number reading: “Book with our local area experts” or similar.

If you offer chat, add similar text to the chat box.

Include pictures of your staff on your website. For example, a group picture of your entire team. Or pictures of your key staff such as reservations, guest experience, housekeeping, and maintenance.

Similarly, display pictures of key staff inside the accommodations. For example, a picture of the entire maintenance team with some text saying “While we hope everything goes smoothly during your stay, we stand ready to respond.”

Include headshots on email signatures.

When you look at the percentage of online bookings that arrive each month, realize that those bookings don’t just show up on their own. Try the Doug Kennedy challenge: Pull 10 online bookings, then look up the guests’ phone numbers in your inbound phone service (e.g., Track, Navis, or Ring Central). You will likely see that most online bookers have called at least once before booking, especially if you rent large homes and condos with higher rates.



Update your after-hours greeting to say something like: “You have reached our local area reservations line after hours. Please leave a message indicating your preferred call-back time range and we commit to returning your call promptly.”

When chat conversations indicate a prospective guest who is early in their search, offer to call them directly right now.

Sign emails with a name, not a department.

Similarly, when replying to in-app messages (such as in Airbnb or Vrbo), sign them with a name, department, and company, such as: “If you have any other questions, my name is Doug, and I’m part of the in-house reservations team here at Brand X Rentals.”

Make it a daily task on the reservations team’s “to-do” list to go back into these platforms and to look at replies sent over the previous day or two, then look up to see if the guest booked and, if not, send a follow-up note such as, “Just wanted to reach out to see what we can do on our end to win a chance to host you here at Brand X Vacations.”

Listen to call recordings of your reservations team. Are they asking investigative questions to start conversations? Are they using a storytelling-selling approach?

Or are they simply asking inventory search questions and then emailing over a list of available properties? (Our experience shows that about 75 percent of vacation rental agents only provide the latter service, which we call “Providing website search support.”) If you do not have time to listen to your team or do not record calls, our KTN team provides mystery shopping as well as remote call scoring.

Remind your reservations team of this Doug Kennedy mantra: “It is NOT our job to help them find what’s available. It IS our job to help them decide. (Callers can do a self-service search of inventory on the very phone they called from.)

While you’re at it, remind the team that phone calls are NOT an interruption to their busy task of responding to emails, chat, and in-app messages. Ring, ring means cha-ching!

AdobeStock By Sergey Nivens

Guest Hospitality

With so much information being available via “self-service” online, today’s guests call much more infrequently after booking and/or while in-house. Therefore, each phone call is an opportunity to “humanize” your brand.

Make sure all staff not only say the company name when answering but restate it at the end while truly offering additional assistance such as: “Cathy, is there anything else I can do for you? (No.) Well then again my name is Douglas. I surely hope you enjoy your vacation with us here at Brand X Rentals.

Realize that your maintenance techs are very often the only human face of your brand. With most companies using remote, self-check-in, if guests see any of your staff in person, it is likely going to be a tech who is there to fix a problem. Provide logoed uniforms, jackets, and hats. Train them on the basics of guest hospitality.

When dispatching work orders, make sure they can easily find the guest’s name.

Train them to greet the guest by name, introduce themselves, and ask permission to enter. I cannot tell you how many times I have opened the door and had a tech walk right in.

Train them to empathise and apologise for the problem before they start resolving it. “I can imagine how frustrating it would be to have your drain clogged up like this, and I apologise for what you’ve experienced today. Let me get with our plumbing specialist, and we’ll get this resolved this afternoon.”

Make sure you have taught them never to say anything like this:

“This happens all the time.”

“We’ve been telling the owner to upgrade/fix this for some time now.”

Encourage them to truly connect with the guests and their “travel stories” while making small talk.

Train all staff to greet everyone they encounter with eye contact, a smile and an enthusiastic greeting whenever they are in uniform out in the field.

Even if the person is not your guest, they are promoting the brand to a possible future guest and/or a possible future owner.

Make sure anyone driving a logoed vehicle practices courteous driving habits and never slams the horn and lost, slow-driving tourists.

Douglas Kennedy is the owner of Kennedy Training Network, which provides reservations sales and guest service excellence training specific to the vacation rental industry. Services include traditional, on-site training, private webinars, and telephone mystery shopping. His articles have been published worldwide and he is the author of “So You REALLY Like Working With People? – Five Principles for Hospitality Excellence.” .

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