Train Your Employees, Please Your Guests

Hal Conick
7/7/2025

When Rachele Hobbs first started working at Hobbs Realty, a North Carolina property rental business founded by her husband in 1977, it was a family business with no formalized training. A few people worked together in an office; everyone knew how to do every job.

One day in 1999, after Hobbs had become CEO, she realized that the company was growing but had no departments or formalized training. At that moment, the lack of training wasn’t an issue—there were only four of them in the office, with new hires typically coming one at a time. But as the staff continued to grow, Hobbs knew that management needed to do more to ensure the success of new hires and the future of the business.

“I wondered, ‘Where’s the opportunity for growth? Where is the opportunity for to professionalize ourselves?,’” Hobbs says. “That put us on the journey of implementing staff training.”

The training process evolved slowly, Hobbs says. At first, the company formed departments and defined each job role, figuring out each role’s essential tasks. Hobbs also thought deeply about the company’s culture and values, like working hard for guests and finding solutions to issues guests face.

Slowly, Hobbs implemented the training process. Success didn’t come overnight—in fact, Hobbs says that it took four years to build a solid onboarding process and truly define the company’s core values. But 25 years later, now with a staff of 25 people, Hobbs says that the company has seen great value in training. Many of the people who started as new hires have moved up to higher positions within the company, staying for years.

“It’s very important to systemize your onboarding because people matter and they need to feel that they matter,” Hobbs says. “From the moment they open that door and arrive, they need to be greeted just like a guest or an owner. They need to be drawn into your culture.”

While Hobbs figured out the benefits of training, many vacation rental managers haven’t. Doug Kennedy, founder and president of Kennedy Training Network, estimates that only 20% of vacation rental managers have a strong focus on training. “There’s definitely a big gap,” says Kennedy, who has trained hotel and vacation rental management companies across the country.

While it’s hard to quantify the effect of training with statistics or metrics, Kennedy says that vacation rental companies he works with go from converting 40% to 60% of their interactions with potential guests after implementing a training process. They also see clear cultural improvements.

“If they look at the big picture of what’s really happening on the landscape, they do see shifts,” Kennedy says. “Staff are saying the right things, and you hear the guests responding to it.”

Here's how vacation rental managers can improve their training and hiring practices, helping to please guests and ensure employees are the smiling, welcoming faces of the business.

Culture First

One of the reasons Margot Schmorak, CEO and co-founder of short-term rental platform Hostfully, started a business is because she felt that company culture was lacking at many of her past jobs. Employees, herself included, often felt underutilized and unactualized in their jobs, she noticed. She wanted to create a better environment.

At Hostfully, Schmorak sees the basis of training as building a culture where employees can feel heard and know that their work matters. She wants people to be willing to ask questions, make mistakes, and even disagree with what she says. That starts with how she behaves at work.

“Before staffing and training, have to take a hard look at yourself,” Schmorak says. “Whatever behaviors you do as a leader are just going to be magnified as the organization grows.”

It’s also up to leaders of the company to communicate well with staff, as employees who don’t feel cared for by the company won’t be able to care for guests or customers.

“The internal culture is the foundation for a healthy business. I don’t see who could be successful without that,” Schmorak says. “If you want to be at your best, you have to feel emotionally full. When there are times when you need to work harder, deal with being more tired, or deal with more crises, isn’t it just better to have a full bucket?”

For Hobbs, culture comes from the company’s core values, which drives the training. “You need to be able to feel confident that when your people answer the phone, what they say is based on the company’s care values,” Hobbs says. “To do that, you have to show, express, and train them on those values.”

Develop an Onboarding System

As the training process evolved at Hobbs Realty, it turned into 90 days of onboarding.

Depending on the position, Hobbs says that this could mean that a new employee will focus on learning software, receive extensive one-on-one coaching, or learn the nitty-gritty of their daily tasks. They’ll also meet with others across the company to learn about other roles.

“We do a lot of cross-training now,” Hobbs says. “We’ve learned that if you hire someone to do field maintenance, you also train them in greeting people, having conversations, and communicating well. They will not only grow personally and professionally, but they’ll also grow your company forward.”

Hobbs Realty is a small enough company that everyone receives training for roles across the company, Hobbs says, but the hospitality side is especially important. Maintenance people are often the only employees whom guests will see during a stay, Hobbs says, so they’re often the unheralded stars who improve greatly from training. When it’s possible, Hobbs even trains vendors on how to greet guests, have conversations, and respond to inquiries.

As a bigger company, one where all employees work remotely, Schmorak says that she still meets with each new hire. But she also allows them to drive their own onboarding process.

When new employees are onboarded, they receive a document of what’s expected from them in their position, people they will meet with, and a checklist of what tasks they should be doing as they learn their roles. Onboarding in this way allows new employees to take ownership of training, Schmorak says, while giving the company a glimpse into their work habits.

“We need people who take the initiative,” Schomorak says. “We built a bunch of little traps in the onboarding document. There was one in the middle of the document that said, ‘Make sure you update your information on the company directory.’ A week later, I would check to see if they had done it. If they hadn't done it, I would look and see, did they miss other details?”

Mentoring and coaching also play a big role in Hostfully’s onboarding process. New employees go through tests and courses, learning everything they can about the product while shadowing other people in the first days of work. After learning a bit, they’ll start slowly by responding to emails and chat inquiries with supervision, getting feedback on where they’re doing well and how they could improve. “Coaching is really powerful,” Schmorak says.

Flipping the Vibe with Heartfelt Hospitality

In the very recent past, Kennedy says that guests would have far more touch points with hotel and vacation rental employees. Before automation, guests may have had 15 to 20 touch points, like booking, checking in, checking out, and seeing employees at a front desk.

Now, if they book online and key into the property with a code, they may interact with zero people. This leads to something Kennedy has often heard from vacation rental managers: Guests are getting angrier.

The more likely prospect, he says, is that when guests are reaching out, they’re doing so because they’re frustrated or angry due to a problem with their stay. “The touch points are dealing with friction—complaints, problems, and challenges,” Kennedy says. “A lot of people think guests are getting more difficult, but the easy ones are being dealt with by automation.”

This is why Kennedy believes that training employees to create positive hospitality encounters is essential for vacation rental managers. “We call it ‘flipping the vibe,’” Kennedy says.

Rather than simply sending an automated email when a guest books, Kenny suggests training employees to call the guest, introduce themselves, and create a positive touch point between the guest and the company.

And rather than using scripts, Kennedy suggests training employees to flip the vibe using sample dialogue. Sample dialogue helps show how conversations should go versus how they must go. People want to talk to humans, Kennedy says, not robots—and scripts sound inherently robotic.

For example, when guests call to ask a question about rates or parking on the property, Kennedy says that the agent can answer their question, and then dig deeper. “Now that I’ve answered your question, can I ask if you’ve made a reservation?” Whether the guest has or hasn’t booked their stay, the agent can then answer any further questions, appease any concerns, or solve any problems the guest may have. From what Kennedy has seen in working with clients, this practice both increases bookings and decreases the chance of cancelations.

“We call it heartfelt hospitality,” Kennedy says. “We use their name, we say ‘you’re welcome’ instead of ‘no problem,’ we show empathy before we apologize. Hospitality is the vibe you put out, and hospitality is the way you make a mutual, shared feeling. It's a change of energy.”

On these calls, Kennedy says that he also trains staff to find the story of the guest. Is this trip a last hurrah before a child goes to college? A family skiing trip? A trip to remember a deceased relative? Behind every vacation, Kennedy says that there’s a story, and training employees to find that story can help them serve guests as humans, not simply another random name. Finding the guest’s story can help create small, positive moments, which helps improve the guest’s current stay and their chance of booking again.

These conversations are also where agents can be trained to cross-sell products, such as personal chefs or local experiences. Often, they learn about these opportunities in pre-stay emails—Kennedy says that alerting them to the ideas early creates a higher chance of piquing their interest and making a sale.

Treating guests this way is a mindset change for many people, Hobbs says, as it’s about having empathy and flexibility. In their training manual, Hobbs says that they call it “going the extra smile,” one of their core values.  

“At 10 p.m., somebody may call and need something,” Hobbs says. “I may want to go to bed at 9:30 p.m., but somebody on the team is going to have to step up. Being flexible is very important. It’s hard to train, but it’s always something that we have to emphasize.”

As Kennedy mentioned, this can be most difficult when guests are upset. But Hobbs says that they also train employees for when guests are upset: Take a deep breath, listen, take notes, then repeat to the guest what they heard.

“You’re going to make them feel absolutely that they are your focus,” Hobbs says. People typically calm down once they feel like they’ve been heard, Hobbs says, and while employees won’t take abuse, they absolutely will listen to someone who is upset and let them know how they can help.

“We find that in what we do, 99% of our guests can be de-escalated quickly with empathy and knowing someone is going to manage the situation,” Hobbs says. “Now, I may not be able to get their air conditioning fixed in 30 minutes, but I am going to be involved in their situation and do everything I can.”

When to Hire More Employees

Companies can’t wait until there are bottlenecks to hire more people, Schmorak says.

At Hostfully, they plan on hiring by looking at metrics and key performance indicators like the number of cases, new projects coming, and the ratio of employees to customers. These numbers, while imperfect, can alert the company as to when they may need to hire to avoid overworking current employees. “Planning is what will make a break your business,” Schmorak says.

Rather than planning from the top down, Schmorak suggests asking people across the company what they need to thrive. Will there be new homes coming in? How many more? What kind of customer support might they need? What kind of sales staff and maintenance staff? “There are all these questions that we’re asking about the future, usually 12-18 months in advance,” she says.

With training for customer support in mind, Kennedy says that it’s important to look at the number of people who serve each property. Companies often tell him that they could never call every person who books online, as they have too many homes. But he says that if a company has 500 homes, they have the revenue from 500 homes and should give attention to serving each property.

When it comes to hiring new people, Kennedy looks to a metric the hotel industry has used for 35 years: average revenue per booking. This is the total revenue from the previous year divided by the total number of bookings.

If a company has enough staff to follow up with potential guests who aren’t quite ready to book—or follow up with guests who just booked—Kennedy says that more guests will book and fewer will cancel. This alone will push up the average revenue per booking, which will cover more money for any extant staff and new hires.

“You, as a rental manager, should have average revenue per booking posted by every phone and by every computer terminal and anywhere people are dealing with guests,” Kennedy says.

Being able to plan hires will also make it easier to time their onboarding, Hobbs says. For Hobbs Realty, she says that they’re fortunate when they can hire someone in November, getting to spend more time training new people before the peak season starts in spring.

“And training them then is so important,” Hobbs says. “If I don’t capture in interest those people in the first two to three weeks that they’re here, I haven’t captured them.”

First Steps Toward Better Training

Perhaps one of the most important things a leader can do when refining hiring and training is to put themselves in the shoes of employees. Schmorak also says that she and other leaders at Hostfully will take days to work in an employee’s role to get a first-hand view of their job. This can help rid the company of annoyances, like wonky software or inefficient processes.

Likewise, at Hobbs Realty, Hobbs ensures that she has worked every job and that employees know that she’s always willing to step into a job when needed. “I'm here to support them in any way I can,” Hobbs says.

Leaders must model their values and show team members the way, Hobbs says. This means leaders giving employees grace, she says, but also leaders giving themselves grace and allowing the training process to evolve over time.

“The grace we give each other daily is worth much more than the anger or disappointment that we can feel when people don't live up to our expectations,” Hobbs says. “One thing that I am so proud of with my team is how much grace they give each other. It's not forced—it’s a natural evolution of the culture that we have built together.”

For Kennedy, there’s no better step toward better training new employees than to simply getting started and experimenting. He suggests that vacation rental companies meet internally to talk about hospitality as a concept and to think about what staying at the company’s properties feels like as a guest.

“A lot of people who work in travel, they think travel is fun, glamorous, and exciting,” Kennedy says. “But really, it’s stressful. You have a lofty expectation for this magical time together, then you get stuck in traffic or the TSA line.”

Having internal conversations about the stories behind guests, how to relieve their travel stress, and sharing information about hospitality through internal channels can all be great ways to improve training and hospitality, Kennedy says.

“I call it rehumanizing the guest experience,” Kennedy says. “Let people know this is a business. The more guests we have, the more money we have, the more successful we are. And that’s good for everyone.”

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