• What evidence can you provide that your product does what you say?

When selecting vendors, be results oriented. Get assurances that you’re going to get value out of the service you’re paying for. Hard data beats a promise every time. 

• Can you provide contact information for current users?

Buying software is just like buying anything else. Get references. (At least three is preferable.) Hearing the experiences of current users is invaluable, letting you know about the software itself, as well as the experience you can expect working with the company.

• What other products do you offer?

One way to see a better return on your investment is to bundle services with the same vendor, so find out what their offerings are. If they provide a software suite that accomplishes several of the tasks you need done, it could be more cost effective to go with that one solution than multiple vendors.

• How long does it typically take for a user to get started? 

It’s understandable to want to hit the ground running after adopting a new technology, but there’s always some amount of time required for training and full adoption. (Need help with your adoption rate? Here’s some advice.) Don’t expect this answer to be a day, but get a sense of how long it’ll take for you to start seeing value from this resource.

• How does your payment structure work, and what do I get for it?

Cost is obviously always going to be a main driver. Learn exactly what you’re paying for. For example, do you get a discount for many users or long-term agreements? Is there a trial period? Is installation, delivery, training, and maintenance included in the price? 

• Does your software solution offer data collection, results tracking, and reporting?

You need trackable metrics and data to determine if a solution is financially viable. Make sure the tool offers some means of measuring client outcomes and productivity tracking. 

• How can I get the greatest ROI out of your software?

Your bottom line is paramount, and asking this question will not only give you valuable insight into how best to utilize the vendor’s service, but it’ll also tell you how knowledgeable and forthcoming they are as a company.

• How customizable is your platform, and can we amend it to meet our needs?

There’s no use taking on a platform that won’t meet your needs and priorities. Unless the platform is a perfect fit as is—pro tip: this almost never happens—make sure it’s appropriately customizable to your business processes.

• Who are your main competitors? Why are you better?

If the vendor convinces you they’re the best, great. You’ve selected the latest tool for your stack. If they haven’t, you’ll come away with a lot of good alternatives to research.

• Are there cybersecurity issues surrounding your product, and if so, what have you done to address them?

Cybersecurity is more important than ever. If you’re dealing with sensitive material (yours or your clients’), make sure the company has adequately addressed how they’re going to keep your data safe.