Choosing software to help you run your business is a big decision. There are a lot of options out there, and it is a bit overwhelming figuring out what questions you need to ask, what features you need and what is going to make your life easier and help improve your revenues. As you start your search, here are some questions to ask yourself:

Do you work day to day in your business? If you do, then you will be wearing lots of different hats, and you will want to make sure the software has an interface that you are comfortable with for the day-to-day activities like booking appointments or making a sale as well as the reporting options that you will need when you have your owner/manager hat on.

Do you want online software or desktop software? This is a matter of what you are comfortable with and if you want to be able to run your business from anywhere. Do you want to be able to go on holiday and still run your monthly billing? If so, then online might be the better choice for you, but if you live in a remote area with poor Internet connectivity, then maybe not.

Do you want to give your members control of their schedules? Have you ever found yourself in a situation where you finish training clients or teaching classes and realize that you have four emails, two voicemails and three texts from clients that need to change their schedules? If you can relate to this, then using online software with a member portal that allows you to set what your members are allowed to do will save you a lot of time.

Do you offer services like personal training, massage and group training that need to be tracked accurately to billing? The more services you offer, the more challenging it can be to ensure accurate tracking of sessions to billing. You may sell packages for training, do monthly memberships and bill your corporate group training contracts at the end of the month. Make sure that the software that you choose can handle the different ways that you have set up your business in as few mouse-clicks as possible. Be aware that the number of clicks to complete daily activities can add up, so think about that when you are assessing software.

Is your business primarily membership-based? Do you need the ability to check members in through a card scanner? Do you have 24-hour access? Can the software you are looking at help you with these, or will it have to be separate? When a member checks in, will you be notified if they have a valid membership or unpaid invoices? You want software that will handle all components of your business in one. As soon as you start having to work with multiple pieces of software, there is room for error.

Do you want to accept credit cards, and is it critical that this function is integrated with your software? Having your credit card processing integrated into your software ensures more accurate data entry. If you are using a separate terminal you or your staff will need to manually enter the data into your software. Some online software will have an integrated e-store for you to use when you sign up for integrated credit card processing.

Do you want to handle failed payments with your clients, or do you want a debt collection service? None of us like being a debt collector; however, you need to think about how big your business is, how close you are with your clients/members and how much you are willing to pay for this service. Typically, companies that offer this as part of their software handle all of your billing and charge you a higher percentage on all of your payment processing, regardless of whether or not the transaction fails. If you are not working day to day with your clients, this might be a good solution for you.

Now that you have determined your software needs, here are some questions to ask the software companies:

How long is the contract? What happens if I want to cancel? You want to know what you are signing up for, how to cancel it and what the consequences are. Usually companies will offer a monthly contract at a slightly higher price and an annual contract at a lower price.

How much is my setup/activation fee, and what is included with it? Are they going to work with you as much as you need to make sure the system is set up properly? Are there going to be extra fees or lack of response once you hit a certain number of hours?

How is your software sold? Very few companies offer an upfront purchase with no annual fees as this makes it impossible for them to service you. The normal way to purchase desktop software is by purchasing the software and having an annual license fee for upgrades and support. Online software is typically sold by monthly or annual subscriptions.

How many different modules do you offer, and what is the pricing for each module? Watch out here; some companies will advertise a great price, but once you sign up, you may realize that in order to sell products, you need to purchase another module that costs another $50 per month. Ask a lot of questions, and make sure you write down the answers.

How hard would it be to add or subtract modules? Once your business is growing, how difficult is it to add new modules to your account, how much will it cost, and how long will it take to get implemented? Find out how they will grow with you so that you don’t have to worry about that in the future. 

What are the hours of support? How can I contact you for support? Is this convenient for you? Is it email-only? Do they have Livechat? Phone? A help portal where you can log your own case? Make sure you understand how they will take care of you, and make sure you feel good about it. 

Do you have references that I can contact? The clients you call will have different business models, but listen to what they tell you. Nothing is perfect, but if they have had a problem, ask them what the response was and if they felt they were well-looked after by the software company. 

I hope that you feel ready to ask some questions and know that the answers you get will enable you to make an informed decision. Remember, a well-chosen software solution is the best assistant manager you will ever have!

Nikki Layton is the CEO of Volo Innovations (, an online billing and scheduling software with fully integrated member management. She is also the co-owner of Momentum Fitness, a personal training studio in Vancouver, British Columbia. You can follow her on Twitter ( and friend her on Facebook (