My experiences in helping others find the right software for them.
These are general questions that I like to ask when someone comes to me and ask what software can help me do X. Generally, they may have done a little bit of research ahead of time. They will typically have the expertise in the field where I don't. I'm able to provide value by asking the questions they don't know to ask given their inexperience in the selection process. Sometimes a customer will come to me and say I want software X. I make sure to play the role of devil's advocate to ensure they have their homework. I've compiled this list based on my experience working with small to medium sized businesses (SMB). My experience has often been in the manufacturing market which lends itself to having a lot of different applications and services to fulfill their wide range of needs. This is intended to be a non-specific starting point for the selection process, inevitably some of the questions won't be applicable as a result.
By simple software I mean software that is used from something that isn't very critical and typically by just one person. My main concern is that the people know how the data is being saved, it doesn't save locally and doesn't require local admin rights. It's frustrating when a software vendor deploys software to save to the local disk, demands admin rights and walks away. Backups aren't optional the use of an admin account is akin to putting a sign on your back that says "Hack me!"
- What is the problem the software is attempting to solve?
- What is their tolerance of downtime?
- What is the sensitivity of the data stored in the application/service?
- Is an NDA required?
- Have they provided references that you've been able to speak to?
- Have you Googled the name of the software?
- Are there results of independent sources discussing the software?
- Vendor lock-in is always a concern. It's important that the software/service has a strong user base.
- What competitor offerings have you checked out?
- Is there a trial period for the software?
- Everyone test drives cars despite the fact that you are only going to learn about the most glaring problems in a 15 minute drive.
- Is there a contract?
- If so, what are grounds for either party to terminate the contract?
- How is the software licensed (users, devices, etc)
- How are payments made (monthly, yearly, etc)?
- Do they offer credits for downtime?
- What has their up time been?
- Where is the data hosted?
- If specialty hardware is needed is this covered with a warranty with the service?
- If so, how quickly will hardware be replaced.
- What are the details surrounding support? Phone based, hours that we can call, unlimited support, etc?
- Do they have any specific certifications?
- How are backups/restores handled?
- Do you have a bug bounty program?
- What is the protocol should the "admin" of the account be terminated? How can we regain control of the account?
- Is the software commodity software?
- Some software markets aren't that exciting and have limits of how much each offering can stand out. Example: Visitor management software, it logs your visitors and is replacing a pen and paper list.
- Ask the sales person "Who do they consider to be their primary competition?"
- This is my favorite question because it either validates that I’m looking at the right competition or they tell me about some company I hadn’t heard of. I hate it when the sales person says something along the lines that we don’t have competition.
- Do they offer single sign on with Office 365?
- Does it integrate with Active Directory.
- What are the system requirements on our side?
- If we need to migrate our data out of the system what are the details surrounding that operation?
- Do they have APIs for customers to access?
- Do they have any software integrations?
- Do they have community forums and or feature request site?
- Is a primary function of the software to save money?