System Questions for Due Diligence

When you are planning an important software system, even in the early stages — and especially in the stages before you talk with consultants and vendors, you should ask some serious questions about what you are trying to do.  Do you really have a good vision of the endpoint of your endeavors, what the system will do, what it will look like, and how all the pieces will fit together?

Perhaps the most important facet of your due diligence is the clarity and coherence of your vision.  Now, this doesn’t have to be thought through 100% ahead of time.  The vision can evolve, but it is important that there be a kernel that grows and becomes more cogent as the planning develops.

As you progress through the planning stages there are a number of questions you should answer as part of the evolution of your vision and your system due diligence.  Here are some of those questions, broken into the general categories of Planning, Technology, Quality, and System Viability & Longevity:


Productive vs. Wasteful Planning Are your preliminary requirements gathering and planning sessions correctly focused, or are you wasting time?
Complete Project Scoping Have you really identified all the tasks required, their costs, and business impacts?
Community Knowledge Do the managers, planners, and designers really know what is going on?  Can they really speak for the needs of all who will be affected?
Collateral Issues Planning What about system configuration, training, knowledge transfer, maintenance, and future enhancements?  These collateral issues and extended planning concerns deserve attention up front, even if they are not fully resolved.


Right Technology for the Job Is the technology being considered really the best choice?  Have you really examined the alternatives?
Features, Capabilities, Scalability Are you getting the features, capabilities, and scalability you need now and will need in the future?
Security and Change Control Security and change control.  How have these been addressed?  What are the risks in the cloud and software-as-a-service?
Data Migration, Synchronization Loading, migrating, and connecting with data:  This challenge is easily underweighted, sometimes by a significant amount.  Have you really factored in all you will be up against here?
Legacy System Risks Interfacing with legacy systems.  Is the original knowledge and documentation still in-house, or are you facing the task of deciphering a lot of cryptic pieces?


Works for All Users, Customers Will the system serve all the users?  How about the customers?  Who will make sure?
“Industrial Strength” How will you know you are getting high quality, “industrial strength” custom work?  Glitzy websites and brochures, and touting special methodologies and best practices are not always indicative of quality.
Risks of Upgrades Will your staff and your business be downgraded by a software upgrade?

System Viability & Longevity

“Own” the System Will your organization really “own” the system, or will you remain dependent on the vendor?  What are your organizational goals for maintaining the system in-house or outsourcing?
Vendor, Platform Risks What happens if your vendor goes out of business or the platform you bought is discontinued?  Can you build “defensively”?
System Longevity Will your new system last for years, even decades?  A premium price tag won’t guarantee it.

Of course these are not the only issues that will demand attention in a software project, but this list is a starting point.

Please contact us with any of your ideas about due diligence for major software projects.

Copyright © 2011 Patrick D. Russell

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