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Published by Lucy Fuggle | Jul 4, 2016 | | 2 MIN READ

20 questions to ask during a booking software demo

When you're looking for an online booking solution for your tours or activities, the chance to have a free demo of the software can be a real asset to your decision making process.

After all, you need a system that streamlines your booking and payment process, provides an experience that's worth a five star review, and keeps you on top of your business wherever you are. This isn't a small decision!

Here at TrekkSoft, we've spent years providing demos to customers in over 125 countries, and many of these calls have been a first touch point for thousands of our customers. Based on this insight, here's our advice to help you ask the right questions and make the best choice for your business.

What to look for before you arrange a demo

You can ask most of the leading software providers for a free demo and request a time slot that suits you and your time zone. When researching software options there are a few things you should look for, and the same goes for a demo. Make sure to check...

  • If the call (by phone or Skype) will be free and with no expectations
  • If you can see how the software in action, including the features important to you
  • If you'll get personalised advice on your short-term and long-term business goals
  • Whether you can ask unlimited questions about how the software will fit and enhance your business

Once you've arranged a few demos with quality software providers, treat each call as a chance to interview the company and find out if they really are right for you.

To help you out, here are twenty of the best questions to ask during your demo.


The best questions to ask during a booking software demo

Check their credibility

1. How many years have you been active in the industry? Where are you based?

2. What wider industry experience does your team have that helps you understand my job?

3. Can you tell me about some of the businesses you work with in my area? And what do you know about my local tourism industry?

4. How many people are on your team? Has this number grown in the past year?


Understand the benefits for you

5. Will your software actually give me a return on investment? Do you offer reporting or analytics that will let me track my growth?

6. Why am I better off with your software than my existing solution?

7. Can I manage my business on my smartphone or tablet when I'm out the office? 

8. Can I improve my website or build a new one? Will it stay mobile-optimised?

9. Can I sync my bookings with my own calendar on Google Calendar or Office 365?

10. Will I be able to distribute on the channels that are important to me? Can I manage these in one place and see all my bookings in real-time?

11. Will I be able to process and manage rentals online, whether now or in the future?

12. Do you offer a resource manager to prevent overbooking of my guides and equipment?


Get to know their payment process

13. Do you offer your own payment gateway? Or can I keep my existing payment service provider, such as PayPal?

14. Will my checkout process be 100% secure? And is it flexible enough to deal with custom bookings?

15. Will customers stay on my site to pay, or be redirected elsewhere?

16. Can I create and distribute voucher and gift codes with your software?


Know whether you'll get the support you need

17. How long will it take me to get set up and ready for online bookings? And what's the timeframe for onboarding? 

18. How much technical knowledge do I need to use the software?

19. How much tech support will I be entitled to? And is your support documentation online?

20. If I need tech support outside your office hours, will I be able to get it?


What you should ask yourself during and after the demo

A big part of your decision making is personal connection. It's worth asking...

  • Do you get on well with the person on the other end of the phone?
  • Do you feel that they understand the industry, your business, and your job?

The representative you speak to is only one individual, but they can usually give you a feel for the company as a whole. Pay attention to these first impressions.

Here at TrekkSoft, we see our free consultations as a great first touch point with our customers. Right from the start, we love seeing you grow with our software.


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Lucy Fuggle
Published by Lucy Fuggle
Lucy spent three years building TrekkSoft’s content strategy and inbound marketing approach. She now helps companies to find their voice, kick-start projects, and bring in processes that actually work for them. Lucy writes and shares her solo adventures on

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