How to
Ryan Harnedy
May 2016

10 Questions to Ask Security Software Vendors Before You Buy

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It’s time. You and your company have joined the 86% of IT pros looking to augment their antivirus with another layer of endpoint protection.

However, as you venture into the world of endpoint security you may find yourself caught up in the dangers of any new product hunt: a jungle of buzzwords, product spec quicksand, and tribes of salespeople hungry for a fresh kill.

If you want to plot a course through these dangers and return to your team with a treasure-trove of protection you’re going to need some guidance.

To help make you look great in front of your boss we here at Barkly put together 10 questions from our Endpoint Security Buyer’s Guide to ask security vendors. Having this simple list in hand can help you get the information you need so you can pick the right tool and get back to work.


1) What specific endpoint problem are you solving?

There’s more than one way to skin a cat. Many vendors represent different approaches to making endpoints more secure — whether that’s through behavioral analysis, sandboxing, patch management, etc (learn more about each of those in our IT Pro's Guide to Endpoint Protection). Each has been developed to address particular security problems. Find out what those are for your vendor and make sure they match up with the problems you’re hoping to solve.

2) Do you offer a free trial?

A free trial is a great way to for you to test out any new tool. It’s also a sign the vendor is confident enough in their product that they’re willing to let you try before you buy.

3) What would pricing look like for my organization?

This one sounds obvious, but it’s amazing how few people really consider what the total cost of new software will really entail until after they’ve evaluated it. Pricing structures can often be confusing. Some software can also require mandatory services that drive up the initial cost. For those reasons, it’s never a bad idea to get perfectly clear up front around how much you’re going to pay.

4) Who do I go to if I have questions?

Chances are, you’re going to have questions as you familiarize yourself with any new tool. It’s important to know exactly who you can reach out to when you do.

5) How long will installation and setup take?

You also need to know what sort of time commitment getting a new piece of security software running will require. A product that takes 10 minutes to install and catches 80% of threats might be more efficient than a product that catches 90% of threats but takes a month to install, configure, and get up and running. Getting an idea of the time and resources required will help you make sure you’re dedicating the right amount of effort to the right project.

6) What does implementation and success look like for an organization like mine?

How have other companies your size or in your industry effectively deployed the solution? Did they have dedicated staff to install and manage it? If so, what kind of experience or training did they need to do so effectively? What did their day-to-day look like as they were getting the solution up and running, and what does it look like now that they’re (presumably) seeing results?

7) What does the renewal or cancellation process look like?

Not only is a simple and up-front renewal and cancellation policy a sure sign of confidence, it will also make your life easier down the road. Only companies with good reasons to be afraid of you leaving will make it hard for you to cancel.

8) What happens if we suffer a breach?

Even the most robust security software can’t guarantee you 100% success. A good security vendor will understand that and will have a clear game plan for how you should respond to and deal with a cyber attack or data breach.

9) What security measures do you have in place?

The chain of security is only as strong as its weakest link. When you partner with a vendor you’re adding their link to your chain, and you want to make sure it’s a strong link. Asking about your vendor’s security strategy will help assure you they take your security as seriously as you do.

10) Can I see your references?

The best way to get an idea of what it’s really like to install, manage, and use a new piece of software is to hear about it from someone who has done it. A new vendor’s references will give you a good idea of a their product’s strengths and weaknesses, as well as the time and resources required to install and manage it. In addition, being willing to share references shows a vendor’s confidence in the power and usability of their software.

If you found this list of questions helpful you should also check out our Endpoint Security Buyer's Guide. It's full of additional checklists and tips to help you cut through the noise and pick the right tools for you. 

Photo by Jared Cherup

Ryan Harnedy

Ryan Harnedy

Ryan writes about how to make cybersecurity make sense to end users and keep employees safe from ransomware, malware, and phishing attacks. He enjoys decoding buzzwords and sharing security tips that users might actually follow.


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