10 Key Questions to Answer Before Upgrading Enterprise Software

The evolution of software has made possible things we never dreamed. With software upgrades come new competencies and capabilities, better security, speed, power and often disruption. Whenever something new enters an existing ecosystem, it can upset the works.

The cadence of software upgrades in large organizations is typically guided by upgrade policies; the risk of disruption is greater in large organizations—which is the chief reason large companies lag up to two versions behind current software releases. They take a wait-and-see approach, observe how the early adopters fare with software upgrades and adopt as a late majority.

A proper upgrade process involves research, planning and execution. Use these top 10 principles to establish when and why to upgrade:

1. What’s driving the upgrade? Software upgrades addressing known security vulnerabilities are a priority in the enterprise. Usability issues that impact productivity should also be addressed quickly.

2. Who depends on the legacy software? Identifying departments that depend on legacy software allows IT to schedule an upgrade when it has the least impact on productivity.

3. Can the upgrade be scheduled according to our policy? Scheduling upgrades within the standard upgrade cycle minimizes distraction and duplication of effort. Change control policies formalize how products are introduced into the environment and minimize disruption to the enterprise and IT.

4. Is the organization ready for another upgrade? Just because an organization needs a software upgrade doesn’t mean it can sustain that upgrade. Upgrade and patch fatigue are very real. Consider the number of upgrades you’ve deployed in recent months when deciding whether to undertake another one.

5. What is the upgrade going to cost? Licensing costs are only one part of the total cost associated with software upgrades. Services, staff time, impact to other projects, tech support for associated systems and upgrades for systems that no longer work with the new platform must also be included in the total cost.

6. What is the ROI of the upgrade? Software updates that defeat security vulnerabilities are non-negotiable—security itself is the ROI. Non-security related upgrades, however, must demonstrate their value through increased productivity or improved efficiency and reduced costs.

7. How will the customer be impacted? Consider all the ways an upgrade could impact customers and make adjustments before the upgrade begins. Doing so ensures you mitigate any potential issues before they happen.

8. What could go wrong? Since your goal is to increase performance, not diminish it, draft contingency plans for each identified scenario to readily address performance and stability issues, should they arise.

9. What level of support does the vendor provide? Once you understand what could go wrong during the upgrade, look into the level of support the vendor provides. Identify gaps in coverage and source outside resources to fill in as needed.

10. What’s your recourse? No one wants to think about it, but sometimes upgrades do more harm than good. In the event something goes wrong and you need to revert to a previous software version, can you?

Download The Guide to Modern Endpoint Backup and Data Visibility to learn more about how a modern endpoint backup solution can simplify software upgrades.

Rachel Holdgrafer, Business Content Strategist, Code42

[Cloud Security Alliance Blog]