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3+ Steps for IT Leaders to Get Buy-In
for a Legacy Modernization Project
10 Jan 2023 | By Sreedhar Tatavarthi

How to get your boss on board

Do you ever feel like you’re the only one at the company that’s championing the initiative to upgrade your systems? You’ve struggled to convince the executive team that modernizing would actually save money. And it’s been even harder to get support for investing in outside IT help.

It’s really no surprise that it’s been that hard for you. 

Change can be scary — and your leadership team could be letting their fear hold them back.

In fact, 47% of CIOs and 58% of CFOsare not able to get buy-in from their executive team to commit to a legacy system modernization project. It’s a vicious cycle that leaves you constantly patching old code and living in fear of the day that something happens to “Bob” — the one guy that knows how to fix that one thing that keeps breaking.

It doesn’t have to be that way. 

You can convince them to leave their multi-decade, complex, and “reliable” old system in favor of one that isn’t so expensive (and frustrating) to operate. 

You simply have to battle their fears and win — I know that sounds dramatic, but it’s worth it if you get the help you’re looking for. So, let me show you how to win and get your boss on board with your modernization project.
Step 1: Embrace the Legacy System
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I know you’re not exactly a fan of the legacy system. It causes daily headaches for you and the rest of your team. You’re tired of handling support tickets, and you know your competitors are reaping the rewards of customer frustration.

So why am I saying that you should support the old system?

Simple. Your boss does.

You might have inherited the legacy system, but your organization poured time, energy, and money into building it. There was a time when it was new, it was shiny, and it was amazing.

Your boss isn’t going to share the same excitement you have for replacing it.

So how do you get your leadership team on board?

You have to present a pathway to modernization that’s more palatable. You need to make it easier to visualize the upgrade as a transition and not an abrupt changeover.

They should understand that you’re not flipping a switch overnight and throwing away their old system. It will be a gradual process with multiple checkpoints along the way to ensure everything is working as it should.

For example, we just finished a project for a software company that had been losing customers because their product suffered from repeated malware attacks due to overwhelming technical debt.

Instead of immediately diving into  building a new, better system, we started by making repairs to stabilize the existing one. We put a focus on shoring up security and backups, and as a result, they were able to stop hemorrhaging customers.

We were able to simultaneously work with the CTO to build a case for a complete overhaul of the application. We documented the challenges and security concerns and made a solid recommendation for what should be done in a replacement.
Step 2: Build Confidence with an Agile Approach
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Change happens — sometimes it’s good, sometimes it’s scary, but it happens.

Your industry evolves and your customers’ needs change. Your ability to keep up or get ahead can sometimes be the only thing you have to keep your competitors at bay.

Your current application has withstood the test of time (mostly). It might be a little rough around the edges,  but it’s evolved with you, and it’s what your leaders know vs a new system they don’t trust — yet.

If you want their buy-in for the upgrade, you need to be able to prove that the new system will be able to adapt. I’m sure you know how much easier it will be compared to the old code that needs a whack with a wrench in just the right spot to keep it going — but they aren’t so sure.

The new application is just a glimmer in your eye at this point. It doesn’t have the same track record of success.

You can help build confidence by using an Agile approach to building the new system. 

At Symphonize, we work closely with client teams in 2-week sprints. This gives us the opportunity to continually review the work completed to date and plan upcoming deliverables for the next sprint with stakeholders.

Working in sprints makes it easy to make adjustments as new information comes to light in your industry, in your company, or as we’re getting feedback from users.

It offers plenty of opportunities to check in and reevaluate goals along the way. Your leadership team will feel more at ease with the process if they understand they’ll have the option to pivot as necessary while the new program is being built.
Step 3: Demonstrate Short and Long-Term Value
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Credit: Marketpulse Research by IDG Research Services. (January 2022). The Path to Digital Transformation: Where IT Leaders Stand in 2022.
90% of respondents in Insight’s State of Innovation Surveyexpect IT modernization to have either a transformative or significant impact on their organization’s long-term growth — including some that haven’t even started the upgrade process as yet.

In the same study, they found that the largest improvements cited by respondents included things that would have a major business  impact, including:
  • User Experience / Satisfaction (40%)
  • Business Continuity (35%)
  • Cost Efficiency/Savings (34%)
  • Resource Optimization (33%)
  • Increased Agility (32%)
  • Increased Innovation/Creation of New Revenue-Generating Products (32%)
Put simply, legacy system modernization  means your customers would be happier, they’d stay with you longer, it would be easier and more profitable to keep them happy, and you’d finally have the bandwidth to do new things that make more money.

Who wouldn’t want to invest in something that would make all that possible?

You know that modernizing your legacy systems will have immense long-term benefits, but do your bosses also understand the short-term benefits — the things that will get better even before the upgrade is complete?

Sometimes it can be so easy to focus on the long game that you lose sight of the benefits that will emerge in the early stages of the modernization process.

My advice to you would be to start looking into quantifying some of those things that aren’t currently possible or profitable in the current system.
Gather the data to back up your case, and you’ll find that it’s much easier to get support.
Step 4: Get a Partner to Help You Make Your Case
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There is one thing I know for sure — projects go much smoother when your executive team is fully invested (not just financially) in the success of your modernization project. We’ve done dozens of legacy system upgrades, and I’ve seen for myself just how big of an impact executive buy-in  can make on the project as a whole.

You have three great tips already that can help you:
  • How long are wait times for new features?
  • How many support requests are coming in each week, and what’s the average response time?
  • How long does it take to release a fix when a bug is found?
  • What new projects are shelved or running behind because you don’t have time to do them?
  • How has your customer retention been impacted?
  • Embrace the legacy systems and acknowledge the hard work and effort that went into them.
  • Plan for change by taking an Agile approach.
  • Demonstrate both long and short-term benefits to an upgrade.
But one of the best things you can do is bring in a partner who’s been there, done that, and knows what you’re up against.

I know first-hand how beneficial it can be to upgrade your systems. I know what obstacles you’re facing as you attempt to field all their objections and win support for your project. I also know how to answer questions that they probably haven’t even thought of yet.

So, if you’re trying to get buy-in from your bosses, I’d love to help you figure out the best solution. 

You can hop on a call with one of our specialists and we can help you uncover and compile the pertinent information to win your case for funding. 

Book a free consultation today and get one step closer to reducing your headaches (and not having to ever worry again about “Bob” going on vacation!)
About the author

Sreedhar Tatavarthi

Sreedhar is a seasoned IT leader with over 17 years of experience spearheading technology strategy, creating business value for customers and business stakeholders through legacy application modernization.
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