October 25, 2022

6 Must Ask Questions When Evaluating Real Estate Software Vendors

Ashley Walsh
Ashley Walsh

Buying new software for your real estate business is a big decision and one that you need to make sure you are entirely prepared for when evaluating real estate software vendors. While you want to ensure you are getting good features that solve your key problems, there are many intangibles that can cost you in the long run if you don’t do your homework. 

Uncover Hidden Costs

Less obvious costs such as time to customize and implement, data migration, onboarding, training etc. should be factored in to determine your Total Cost of Ownership (or TCO) so there are no surprises down the road. More importantly, when putting in your time and effort to move to new software, you want to have confidence that it’s going to be a long-term partnership that can scale with your business to avoid the dreaded switching costs again.

Be Prepared

The best way to ensure you evaluate each potential vendor equally is to compile your list of questions in advance before taking any demos. Coming prepared to obtain answers to critical questions from the start will signal to the vendor that you are prepared and give you confidence that you’ve covered all your bases before you sign any agreements.

Ask Smart Questions

The following questions will cover the key areas real estate professionals should evaluate when selecting a software vendor for their team or brokerage.

What is the average time to adoption?

If you’re implementing any business-critical real estate software such as a CRM, transaction manager, e-signature or back office tool it’s likely that you will need to customize the software for your brokerage or team and that you’ll have historical data to import. 

It’s normal for these customizations to take time to setup, but time is money and It’s helpful to align expectations so you have a smooth transition without surprises.

What type of training and support do you offer?

This is vital because you and your team need to know what level of help you can expect from the software vendor if something goes wrong or if you have a question that needs addressing. Technical support can vary widely by the vendor. On the low end, you may only have self-service access to help articles. Better companies will typically layer chat and email support onto their knowledge base, while best in class companies will include features like dedicated account management, phone support, or 24-7 support. To take this question a step further, you could also inquire about average response time.

When was your last feature released and what was it?

When you invest in software, the last thing you want to do is outgrow it too quickly and be back on the hunt. The real estate industry, unfortunately, has many technology platforms that have become stagnant and haven’t kept pace with new innovations. If your sales rep is stalling or deflecting this question, it’s a sign you shouldn't ignore.

Do you have references for customers like me that I can contact?

This is a great question for peace of mind, but can also really help you get the most from the software. Talking with a peer in the real estate industry can uncover best practices or creative tips, and tricks that it may have taken you months to discover on your own.

Who are your main competitors and why are you better?

What is your cancellation policy?

This may seem like a no-brainer, but it’s always good to understand what your options are before you sign up. If a company does not allow for early cancellation of long-term contracts, a good follow-up question would be to ask what percentage of their customers renew. This will help you understand the longevity of relationships the prospective vendor has.

If I leave, what happens to my data?

Many agents don’t consider that certain systems become the storage device for critical data such as client contact information, transaction history, and important legal documents. For compliance reasons, much of this real estate data must available for several years so it’s important that it’s stored in a safe, accessible place.

Some vendors make it easy to get data into their systems, but there is little incentive to make it easy to get that data back out. Ideally, you can have that data exported, or pay a more nominal fee to the vendor to host it for you indefinitely.


Now that you’re equipped with the knowledge necessary to make smart real estate software decisions, you can go into your next sales meeting with confidence. Unsure whether it’s time to change software vendors? It’s never a bad time to do an annual software audit.

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