All or Nothing: How Far Should Legacy Upgrades Go?

Most enterprises looking to tackle the challenge of modernization initially want to upgrade everything. But that isn’t always appropriate or feasible. At some point, you are going to have to draw a line in the sand. 

It’s an important decision. Defining the scope of your legacy system upgrade is one of the most crucial steps in the entire process, Cast Software’s Thomas Hjelm says. The problem is many people assume the process is relatively simple and straightforward, so they don’t worry about scope definition. Naturally, this lack of clarity can lead to severe problems further down the line.  

Whatever you do, don’t go into your update efforts without a clear plan. Here’s a 4 step plan on how you can get your modernization efforts off to the best start possible by clearly defining the scope of the upgrade work. 

Start by Defining What Your Legacy System Is

The first step is to define exactly what constitutes your legacy system. This might seem obvious, but it isn’t. 

Praxent managing partner Kevin Hurwitz compares legacy systems to the human body in their complexity. That’s because they are typically the result of hundreds of applications and features that have been created and introduced over the years by dozens of different employees. Not appreciating the size of your legacy system is one of the biggest mistakes that executives make, Hurwitz says. 

With that in mind, you should be prepared for your modernization to be much larger than you initially imagined. Legacy systems can certainly be complicated, consultant Manish Mehndiratta says. “In some cases, upgrades of each application will envelop the data and processing of their earlier versions, which eliminates the legacy challenge. In other cases, whole apps will be discarded in favor of more efficient and cost-effective options.” 

When it comes to actually defining your legacy system, Mehndiratta recommends looking at your entire technology stack and separating each application into the following three buckets: 

  • Emerging. These are your most up-to-date apps and are often completely new. When they aren’t, then the foundational platforms have also been upgraded. These don’t require modernization.
  • Under evaluation. These are apps that are still in use and still work relatively well. However, they may have features such as old code that will mean they will need to be looked at in the future if not right away.
  • Declining. These are your most outdated applications and the ones you need to focus on. They are no longer supported or won’t be very soon. 

The team at RTS Labs recommends breaking everything down into its individual parts. Start by separating applications from your company’s overarching infrastructure. Then, work out the networking, structure and storage needs of each application. You should also consider which applications are suitable for the cloud and in what way. 

Taking your legacy infrastructure as a whole can be intimidating, but taking it application-by-application is much more manageable and can help to inform what really needs modernizing.

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Focus on the Important Things First

Once you have defined exactly what your legacy system consists of, you’ll probably come to the conclusion that it can’t all be done at once. If that’s the case, then it’s essential to focus the scope of your modernization strategy on your most important applications. 

Cybersecurity expert Kayne McGladrey recommends identifying the elements of your business that separate you from your competitors. These are the elements that you want to improve on first and the ones that you should spend the most time on. 

“If accounting, cybersecurity, legal affairs, or marketing is not core to your organizational identity, then plan to migrate away from your legacy systems and processes in those areas,” McGladrey tells “Organizations can then focus their limited time and resources on improving what they do well, and what customers value most about those organizations.”

It doesn’t just have to be the applications that are linked to your USP. Any application that improves the customer experience should be considered a must for modernization, PwC’s Leon Cooper and Milan Vyas write. That’s one of the main reasons behind your modernization process, after all: to deliver more value to the customer.

Remember, you don’t need to do everything at once. If you focus on mission-critical applications first, you can move on to less important applications at a later date. With this in mind, Mark Rhyman, co-CEO and chief business development officer at Big Bang ERP, advises businesses to differentiate their “nice-to-haves versus must-haves.” 

Must-haves need to be included in your legacy upgrades. Nice-to-haves don’t. 

Let the Company’s Team and Culture Guide You

How far you go with legacy upgrades should also be determined by your company, its culture and its employees, notes Avanade VP Michelle Mercado. “Some companies have the incentive and resources to rip off the bandaid and shift quickly; others need to carefully roll out metered changes in order to move forward without significant setbacks.”

The right upgrade strategy will be different for every business, notes Chris Rickard, co-founder at custom software company inoutput. For some, particularly smaller companies, it may be possible and preferable to make upgrades all at once. For most, however, a gradual approach will be the most sensible. 

“This is usually the more common approach, especially when there are lots of users involved, as you can stagger user training, and iron out any issues with implementation before switching to your new system,” Rickard says. When this is the case, the scope of your initial legacy upgrades don’t have to be as large.

The decision of whether to update or replace legacy applications may also depend on the skills of your workforce. If you have a large and highly skilled team, it may not be necessary to replace certain applications just yet. If your team doesn’t have the skills necessary to keep legacy applications running, however, or if you are worried that these technicians may soon leave the company, updates will be vital. 

In some cases, updates may not be possible at all, and you could be forced to live with the legacy, notes Pivotal Director of Marketing Michael Coté. “Think of external systems like airline and hotel booking platforms, or at the infrastructure layer networking and CDN configuration. When you can’t directly or quickly modernize these legacy systems, you need to put in a scheme to quarantine these systems and, longer term, a scheme to modernize or replace them.” 

In short, these kinds of applications have no place in your legacy upgrade plan.

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Don’t Be Afraid of Big Scopes

Even if you only focus on your business’ most important applications, the scope of your legacy upgrade could still be huge. If this seems scary, don’t worry. Big scopes aren’t anything to be afraid of.  

Leading companies, even ones that have a huge modernization vision, don’t approach it as one single large transformation, says Peter Bendor-Samuel, founder and CEO of Everest Group. “Instead, they break the modernization journey down into a set of smaller journeys. These smaller individual journeys enable a company to make consistent, productive progress that better supports the business and reduces operating costs.”

This is the approach your organization should take, as well. Rather than looking at it as a single event, break your scope down into several smaller scopes. Bendor-Samuel suggests moving applications to the cloud first, then modernizing the network, then modernizing your company’s approach to application development, and so on. 

You could split your transformation steps according to importance. Modernize critical systems first, then move onto the next most important systems.

This kind of iterative rollout doesn’t just help you come to terms with huge legacy update scopes. It also gives you the best chance of success. Monolithic rollouts are one of the biggest legacy update mistakes that business can make, says ReadWrite managing editor Deanna Ritchie

Legacy upgrades are big commitments that require a substantial amount of work. Coming to grips with exactly how much work is required is one of the first steps in making the process a success. No matter how unmanageable it may seem, make sure that you clearly define exactly what a legacy upgrade entails to make sure that you get the best results possible. 

Images by: Mimi Thian, bonneval sebastien, Alvaro Reyes

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