To upgrade or not to upgrade that is the question | cullen4congress

To upgrade or not to upgrade… that is the question for enterprise software users

Updating a major software application can be challenging. Many factors come into play, including budget issues, downtime, upskilling staff, and dealing with software and automation dependencies. If you are trying to decide whether or not to update your business software or to replace legacy software that no longer has a strong value, this post is for you.

The drawbacks of technical debt

The « technical debt » is the cost for an organization not to control some technical insufficiency. Sitting year after year with outdated software that doesn’t meet your business needs can have long-term effects that include insufficient security, unpatched product issues, and lack of features found in more contemporary applications. It can create more work for your resources, stagnate your team’s skill set over time, and lower overall morale among staff. And it is very expensive.

InformationWeek estimates that US IT wastes $85 billion a year on bad technology instead of buying or developing better software. And this doesn’t take into account other teams in your company that might be contracting separately with vendors for a more robust option.1

Gartner predicts that by 2025, 40% of IT budgets will be spent on maintaining technical debt.2

So ask yourself: are you not satisfied with your current software? How long has it been since it was updated? Are your users getting the most out of the product? Before you decide to move from one app to another, you might want to count your answers to a few other questions:

  • If it’s been a while since you upgraded, have you looked at its latest features to see if they fill the gaps in your expectations? For example, does the newer version include automation or use AI to make your team’s work easier? If the software is still missing, have you talked to your software vendor about what’s on the product roadmap and if you can be a part of that decision-making process (i.e., would they allow you to sit on an advisory board or sponsor new features with your development team)?
  • Are you already using different products that essentially do the same thing to accommodate other teams/departments/etc.? If so, can your existing software deliver the same desired functionality after upgrading or replacing it with something better on the market?
  • How expensive is it to maintain your current software (eg, hardware, resources, vendor costs, etc.) and would it be reduced by upgrading, relocating, or replacing it with another product? Does your provider provide installation flexibility (ie, on-premises installation, public cloud installation, private cloud offering, etc.)? Do they have service offerings that make it cost effective to use your staff for operational support rather than doing it completely in-house?
  • If your users have difficulty using the software, it is because you are really a user. unfriendly Or do users require any additional training or guidance? That is, would your experience with any other software really be different under the same circumstances? Does your provider offer a robust training program and assistance with SOPs and best practice development to further enable your users?

Develop a software upgrade project scope

Once you’ve compiled your responses to the above, discuss some of your top picks. Use a trusted vendor to do some of this heavy lifting by giving them your needs/criteria to meet. Then select your most ideal scenario and at least one other alternative that is less expensive and/or resource intensive. This will give you a backup plan if the ideal scenario does not gain the necessary buy-in.

Break down the scope of your project to include both IN-SCOPE and OUT-OF-SCOPE. This will keep you from trying to account for everything. Be sure to include the basics, such as:

  • Project goals (eg, access to contemporary software with enhanced features and security, more efficient workflows)
  • Project deliverables (eg, latest software version in production environment; staff training; revised SOPs)
  • List of resources (eg, internal team, vendor(s), infrastructure)
  • Chronology

Creating a Cost Benefit Analysis

With your project scope in hand, start building your cost-benefit analysis. This analysis may include the following elements:


  • Direct labor costs, including vendor service fees
  • Direct costs of hardware or other materials, including the potential costs of a public cloud space or a private cloud offering
  • Impact on daily activities, such as interruptions/downtime
  • potential risks


  • Long-term cost reduction, such as maintenance of old technology, compensation of resources with personnel placed by the provider, efficiency gains, etc.
  • Increases in production response times or sales revenue
  • General infrastructure and security improvements
  • Competitive advantage like top-of-the-line software, best-in-class service team, etc.
  • Intangible benefits such as employee satisfaction.

Develop stakeholder buy-in

Compile a list of your company’s internal stakeholders, such as end-user management, technology owners within IT, and leaders of your information governance team. Please include good notes about the value the software provides to them individually, along with your most likely concerns regarding an upgrade. Please reach out to the key stakeholders on this list and make sure their input falls within the scope of your project.

Prepare to overcome common objections, such as preferences for less popular software applications. Address these objections with leading questions to help identify how your solution will address their overall concerns.

Better software update result

While change isn’t always easy, it’s usually a good thing when it comes to technology. By evaluating what you need with a trusted provider and breaking down costs versus benefits, you’ll have the tools you need to make this decision, gain buy-in from your stakeholders, and take the next steps.

1Information Week, 2022. CIOs: Stop Spending on Bad Tech

2ComputerWeekly, 2022. What are the drivers for application modernization?