Category Archives: New Software

How to Install New Vacation Rental Software in 30 Days

Changing Priorities
Changing Priorities

Alight, you have chosen your new software package, your staff is on board, and you are ready to go. So let’s talk about priorities.

The number one thing that will drag out a software installation, is not making it the top priority for your company. (Read that again.)

I have seen this happen time and time again. What should be a 30 day project (or less) is stretched out to 3-4 months or more because the vacation rental company treats their software installation like a “if we have the time” kind of project. And they usually don’t have the time. (The longest installation that I was involved with took nearly 2 years because the company put it at the bottom of their list of things to do.)

I get it, you have a business to run. Guests to call back, staff to help, issues to deal with, owners to keep happy, e-mail to respond to, lunch to eat (if you’re lucky). Not to mention a new software system to learn, a website to design, data to enter, choices to make, and a never ending project list. There aren’t enough hours in the day. Maybe if you had a larger staff you could make it a priority, but being a small company it just isn’t possible, right? Or is it?

I’ve seen small (3 person) vacation rental companies get completely up and running, staff trained, new website designed and launched, and all data entered into cloud based vacation rental software in under 30 days. They did it because they made it their #1 priority. Everything else came second.

They didn’t ignore the rest of their business. They just made sure that they got done whatever it was they needed to on their installation that day first, before they tackled anything else. They also put in a few extra hours here and there if it called for it. And they were happy they did it because it was all behind them before they knew it.

There’s an old saying that goes “What’s urgent isn’t always important, and what’s important isn’t always urgent.” Use this as a guide when approaching your software installation. There are a ton of things competing for your attention every day, but they aren’t all important, and they aren’t all urgent. Some of them, in fact most of them, can wait. At least for a few hours. What is important are the things that are going to help you reach your goals.

I recommend to clients that they make their software installation the focus of the first couple hours of their day. Come in, get your coffee, and get to work on the installation. Come in a little early if you need to. Don’t listen to voicemail, don’t check e-mail, or Facebook, or read the paper, or talk around the water cooler. That can all come later. Focus on your installation.

Watch videos, enter data, and follow up with your vendor, whatever needs to be done that day. (A good software vendor will provide you with at least a loose outline of steps that you need to take to complete the installation. If they don’t, or you need help in this area, contact me via the Contact tab and I can help you.)

Once you’ve completed your installation tasks for the day, then move on to e-mail, phone calls, voicemail, staff meetings, etc.

Now, there are some things like reservation inquiries and angry owners that can’t always be put off. But you can develop a plan to deal with these if/when they pop up.

  • Designate one member of your staff to follow up with inquiries while the rest of you focus on the installation. You made need to rotate who this person is on a daily/weekly basis.
  • If you get an e-mail or a call from an angry guest or owner and it just can’t wait, step away and deal with it and then come back to the installation. If it can wait, tell them that you need a bit of time to look into what is going on and that you will get back to them by the end of the day. Then get back to your installation tasks.

The truth is, we accomplish what we prioritize. So make sure that you are prioritizing the right things and your installation will run a lot more smoothly and be completed in a much shorter timeframe.

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3 Factors in Choosing the Right Vacation Rental Software

Searching for Software
Searching for Software

You have written out your business goals, created your feature set list of “must haves-like to haves-nice to haves”, done your research on trends and technology, and talked with your staff about their needs. Now you are finally ready to start shopping around. (Earlier posts in this series cover developing business goals and feature lists, click here to read them.)

#1 Awareness

Before you reach out to any software companies, look online and ask around to find out the various offerings and reputations of each one. Many of the software companies post detailed information about their feature sets, along with demo videos, and testimonials on their websites and social media pages.

It also helps to talk with their current customers and hear what their experience has been. But, make sure to consider the source when you are getting feedback. If someone is adamant about how great or awful a particular vendor is, are they also someone who always grumbles or offers praise regardless of the situation? Or do they tend to offer fair and balanced assessments. Don’t ignore their input, just be sure to put it in context.

Once you feel like you have a good lay of the land, reach out to those companies that you think are going to be the best fit for you. At this point, don’t worry about pricing.

#2 Be Realistic

Keeping in mind that no software is going to do everything that you could possibly want right out of the box, measure the offerings against your goals and feature list. If a software package will give you the tools to achieve all or most of your goals, has all of your “must haves”, a few of your “like to haves”, and has a great reputation for customer service, then they’ll be a good fit for you.

On the flipside you don’t want to purchase software that only has a few of your “must haves”, lots of “nice to haves”, and doesn’t really help you achieve your goals, but it’s well within your budget.

#3 Nuts and Bolts

Once you have your short list of software vendors, you can then shorten the list even further by considering things like pricing, timeframe, data import tools, training resources, and cancellation/refund policy.

Let’s look at each of these briefly;

Pricing – This should not be your sole deciding factor. That said, you don’t want to choose something that you have to go into debt to purchase.

One thing to keep in mind is that purchasing software around the end of the Quarter or year (end of March, end of June, end of September, and end of Dec) can sometimes net you a significant discount. Many sales people are trying to make their quarterly/annual goals and may be willing to give you a price break in order to get your business. Or instead of lowering the price they may be willing to throw in additional services at no cost.

But be careful, this can backfire on you. If your salesperson is having a great quarter or year and doesn’t need your business to make their sales goals, not only will you not receive the discount that you’re hoping for but you could lose your window of opportunity for a timely installation. Tread very carefully with this one.

Timeframe – How quickly can they start working with you? Are they backlogged for two months or can they get started with you right away? What is the average amount of time that a company of your size takes to get installed?

Keep in mind that a backlog is not necessarily a bad thing. It can indicate that quite a few companies see the software as the best option to have. Where it can prove difficult is when their time frame doesn’t align with your timeframe.

Understand too, that how quickly or not an installation takes is largely dependent on you. Getting a feel for timeframe from the software vendor can help serve as a guide for budgeting your time and give you a realistic expectation.

Data Import – Can they do it? What can they import? Does it cost extra or come as part of the package? How much will you manually have to enter on your own? The answers to these questions will impact your installation timeline.

Training Resources – Do they offer videos? Live classes? On-site training? Are they extra or do they come standard? Do they break out training in smaller chunks to get you running or do they throw too much at you all at once?

One of the nice things I have found about video training is that you can refer back to it as often as you need to. You can pause, rewind, fast forward, etc. to suit your learning style. Video training is not the be-all-end-all, but it is a very valuable tool.

The way that I recommend to approach training is to focus on getting started, rather than learning everything there is to know. Learn what you need to in order to get up and running. Then go back and become an expert.

Cancellation & Refund – No one likes to get here but it inevitably happens once in a while. Different companies offer different things, so you’ll need to ask about this specifically.

One thing to keep in mind is that software companies incur costs and expend resources in helping you get installed. Like any good business they need to make sure that they cover their costs or they won’t be in business long. So just because a company doesn’t offer you a full refund, doesn’t mean they just want your money. They need to stay in business too so they can continue to support their customers.

Making a Decision

Now you can make the best choice for your business based on all of the variables. And most importantly, don’t ignore your gut. If it’s telling you to go with ABC Company even though on paper they may not be the best fit, don’t ignore that. Likewise, if your gut is telling you that something is wrong with XYZ Company even though they have everything you could possibly want, then it’s probably too good to be true. You may need to take more time, do more research, or talk to more people that use the product. That’s ok. Better to make a wise decision, even if it takes a little longer, than an impulsive one.

If you would like help in choosing new software, navigating a software installation, or getting back on track with an existing one, contact me through Contact tab on this website. I have managed and assisted with dozens of software installations and can help you make yours successful.

Next – Priorities

The Most Important Component in Vacation Rental Software Installation: Your Staff


The most important component that will determine the success or failure of a new software installation is getting your staff on board with the project. This is so critical to success that I felt it deserved its own post. I have seen software installations literally come apart at the seams because the staff refused to going along with it. Unfortunately it forced the business owners to throw in the towel and they often didn’t recoup all of their investment. The good news is that this can be avoided with a little bit of planning and communication beforehand.

Heads Up

First, let your staff know that you are thinking about switching to new software as soon as you have made the decision to start looking. If nothing else, it gives them time to get used to the idea. Explain to them why you believe it is the right move for your company (be specific) and invite their feedback, questions, and concerns. If you wait to tell them until you have already chosen new software, you may have missed blind spots that they could have helped you see that would have changed your mind.

Heads Together

Second, invite them into the process of evaluating how new software can help you reach your business goals. They are the experts at their job and can help you create your list of “must haves”. This also gives them some ownership in the process, which makes them more invested in its success.

The instances where I’ve seen software installations come completely unraveled are where the staff resented the fact that they were not consulted about the change in the first place. So they complained about every little thing and made mountains out of mole hills until the owners threw up their hands in defeat. This could have been avoided by inviting them into the process from the beginning.

It’s A Team Effort

Third, as you look at the various options that are out there, have your staff (ideally your department heads/team leads) evaluate the software with you. But do your salesperson a favor and designate a single point of contact that compiles everyone’s questions/concerns and sends it to them once or twice a week.

Don’t overwhelm them by having everyone in the company bombard them with questions and comments.

Once you have decided on a particular software package, explain to your staff why you chose that particular option and help them see how their feedback made it happen.

Dealing with Stragglers

Even after all of the above you may still have an employee or two that refuses to get on board. Maybe you went with a different option than what they wanted, maybe they’re afraid for their job, or are just resistant to change in general. Whatever the reason, try and understand specifically what they are concerned about. Then, ask for their help in making this a success. Software installation is a huge project and everyone involved is critical to its success.

If that doesn’t work, you may have to put your foot down and explain that while you understand and appreciate their concerns, you believe this is the best move for the business. At the end of the day a company is not a democracy. You’re the boss and you have to decide what’s best for the business. People are counting on you to lead them.

This person may no longer be in the right role, or a good fit for your company. They might be better suited for a different team or it may be time to part ways. Whatever the case, you may have to make some hard decisions. It’s an unfortunate part of leadership that never becomes easy.

The good news is that by involving your staff and communicating regularly, it will greatly reduce the chances of these kinds of situations considerably.

Next – How to Find the Right Software

Buying New Software – 4 Steps to Ensuring Success

Setting Goals

Switching vacation rental software can be a daunting task.

Who has the best options?
Which offering is most cost effective?
What will you have to give up and what will you gain?
How disruptive will it be?

Before you undertake the task of switching software, there are a few things that you can do up front to make the job easier down the road. You will also want to give yourself plenty of time to prepare for the switch. I recommend budgeting at least a year for the entire process. That covers everything from looking at the different offerings to the actual installation of the software.

But before you start looking at what is out there, you’ll want to decide a few things first.

#1 Determine what your business goals are for the next 2, 5, and 10 years.

What are your goals as a company for each of those time segments? To increase your revenue? Stronger relationships with your owners? Growing your inventory? Enhancing your guest services? Reducing operating costs?

Knowing what you want to accomplish in the short, mid, and long term, will inform your decisions about the kind of software and services that you should purchase.

I recommend picking no more than 2-3 goals per time segment to drive towards. You can always update or adjust your goals if you find that your priorities have changed. Your long term goals in particular will change as time goes on, but they provide a clear direction for you to move in.

Write out exactly what these look like for you. What does “increasing your revenue” look like? By how much? What is the percentage or amount growth required to take your business to the next level? What are the specific steps that you need to get there?

What specifically does “enhancing your guest services” look like? What tools do you need to do it? What would you like to do that you can’t currently do?

If you don’t know the answers right away, that’s perfectly ok. Spend some time brainstorming, researching, and getting input from your partners and staff. The point isn’t to have the perfect list that will never change, but to have specifics that will guide the direction you move in. Those items may change depending on various things that are completely out of your control. That’s ok.

#2 Develop a comprehensive list of “must haves”, “like to haves”, and “nice to haves”.

No software package is going to do everything you could ever possibly want it to. There are going to be trade-offs and different ways of doing things within each option.

To get as close to the ideal for your business as possible, you need to know what matters most and what you can live without.

Instead of focusing on everything that your current software has that you don’t want to give up, focus instead on those business goals you wrote down. What do you need to achieve those goals? What do you need to continue to perform operationally while you move towards those goals? Define “need” as “can’t possibly live without”. It’s not that you could live without it and just prefer not to, you have to have that particular feature/report/widget in order to do what you need to do. This list should be as short and concise as possible. Remember, these are needs not wants.

Next come your “like to haves”. These are things that you could live without if you had to, but it could be fairly painful. They don’t directly tie into the achievement of your goals and operational requirements, but they support the things that do. Or they make your life a heck of a lot easier.

Finally there are your “nice to haves”. These are things that would be cool to have but your business isn’t any better or worse off with or without them.

Make sure to involve your staff in this process and have them come up with their own lists based on their roles within the business and the goals you developed. This will not only give you a stronger pictures of your business needs, but will also help them have a sense of ownership in the decision as well. This can make things quite a bit smoother down the line and shouldn’t be underestimated.

You will then combine all of the lists into one master list of “must haves”, “like to haves” and “need to haves”. Be brutal in your assessment of what is a “must have” and what is a “like to have” or “nice to have”. As painful and frustrating as this process can be, it will make things much easier in determining whether a product is a good fit for you or not.

#3 Data clean up

This is never fun, but you will be glad that you did it. Any software that you purchase should be able to import some of your data. At the very least things like Units, Contacts, and Owners.

If you have been using your current software for any length of time, there is probably quite a bit of junk in there. Duplicate entries, fields you used for things other than what they were designed for, etc.

As soon as you know you want to start shopping for new software, start on a data cleanup project. Determine what you want to bring over to the new software (it may or may not be importable, but it can always be manually entered) and what you don’t care about. Don’t fall into the trap of “I need to have everything”. If you host your current software, then you can always refer back to it if you find that there is data you need. If you are using cloud based software, export as much of your data as you can by running reports, exporting them to Excel or PDF, and saving them to a local drive to refer to later. (Make sure to save them to more than one drive in case your machine crashes. Burning the data to a cd is always a good idea.)

Then go about cleaning the data up. You may be able to pay your nephew a few bucks an hour to do this, or buy your staff pizza if they put in extra hours for data clean up. However you do it, you will never regret getting started sooner rather than later, and it probably won’t take as long as you think. A few hours each Saturday for a month will probably take care of it.

#4 What is it that you don’t currently know?

We’ve all had the experience of buying something only to find out about a different offering that, had we only known, we would have gone with. “I wouldn’t have bought the iPhone 5 if I had known the iPhone 6 was coming out in 3 months!” Right?

What is it that is just past the horizon that you are currently unaware of? Do your research and try to find out. Maybe there isn’t anything. Maybe you are totally up on all of the trends and new offerings in the marketplace and have a keen grasp on where things are headed. But make sure.

Read articles, talk to people, and attend webinars. Invest a few hours a week in your education on this. It can save you a bunch of anxiety and regret down the road if you know you are purchasing something that won’t soon be outdated. HomeAway, TripAdvisor, Tnooz, and PhocusWright are just a few of the companies that regularly report on new trends and technologies. I also write a blog post every Friday around news, trends and findings in the travel and tech industries that will help you.

No matter the size of your company, how long you have been in business, or how tech savvy you may be, give yourself plenty of time to choose and install new software. Make sure that you have taken the time to clarify exactly what you need to get where you want to be.

Next – Selling it to Your Staff