10 Jan 2023

| By

Sreedhar Tatavarthi

5 signs you're falling behind & need to modernize your legacy software

How do you know when it's finally time?

You know what it’s like to be in charge of systems that are long overdue for an upgrade. You’re constantly fighting against old code and fielding customer complaints — it’s not a fun position to be in.

You already know that it’s costing your company money and giving your competitors an edge. But a legacy modernization project is a big investment of time and money.

How do you know when it’s finally time to take it on?

We help CIOs and CTOs evaluate their legacy systems all the time, and we know what metrics to check. Let me show you how to determine if it’s time to put your old system out to pasture so you can reclaim your competitive advantage.

Sign #1: Customer Response

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Your customers will tell you — maybe not in so many words — when it’s time to update your systems. This sign can be very frustrating, but it’s also usually extremely accurate.

If you’re not currently documenting the following data points, it’s important to start. These metrics will let you know if you’re on a sinking ship and need to make some changes ASAP.

You’ll be able to interpret customer response in a few different ways, such as:

  • An increase in the number of customer support requests
  • Rising support request resolution timelines
  • An increase in escalation requests where support tickets are passed to the development team
  • Repeat requests from the same customers with escalating harsh language
  • Customers indicating dissatisfaction with support request resolution on customer feedback surveys
  • A decrease in overall customer satisfaction when you do NPS surveys (and if you aren’t doing those, you should start)
  • An increase in negative online reviews
  • A decrease in new customers
  • An increase in customers migrating away from your platform
  • Customers are downgrading to cheaper versions of the software — including any options you have to downgrade into “storage mode” only.
  • Customers are reducing the number of users on the platform or changing their primary user to emails like “” — this indicates they are cutting costs and getting ready to move to another platform.

Sign #2: Security Concerns

Platform security is obviously a major concern, especially if your platform stores customer information or proprietary company knowledge.

Security breaches are serious and can be incredibly costly for the company, but you may start to notice signs that your security systems are being compromised long before a major problem occurs.

Here’s a few warning signs that you can look for:

  • Password reset or new account emails containing usernames and passwords in plain, unencrypted text.
  • Passwords are stored in your database in plain, unencrypted text.
  • Your systems don’t have password complexity compliance, such as requiring longer passwords or special characters.
  • You aren’t able to perform updates on third-party components like plugins or themes because they are no longer compatible with your core systems.
  • You don’t have systems and processes in place to regularly assess your systems and test for vulnerabilities.
  • You don’t have internal restrictions to customer data — such as limiting billing information to the accounting department - or rules for outside vendors that are accessing data.

Sign #3: You Aren’t Providing Continuous Value

Software is a highly-competitive industry. Most companies fall into one of two categories. They are either releasing updates and new features on a regular schedule or releasing them randomly.

Customers want to know when new features are coming. Moving to a new platform is a hassle they don’t want, so they will usually stay invested in your platform instead of jumping to a competitor so long as you’re communicating effectively.

Here’s a few signs that your old systems are holding you back from meeting customer expectations:

  • Customers are asking when new features will be released, and you can’t accurately predict the timelines — even to say something vague like “Q1 of next year.”
  • You don’t have a prioritized backlog of features that are planned for upcoming releases.
  • You aren’t releasing major updates at least twice a year.
  • You aren’t releasing minor updates at least quarterly.
  • You aren’t releasing bug fixes or security updates at least monthly.
  • You’re spending more time on bug fixes and security patches than you are on developing new features.
  • New releases are often buggy and are followed by a flood of support requests and complaints shortly after you release them.
  • You aren’t announcing new releases to customers.
  • You aren’t incorporating customers into the process to beta-test new features before release.
  • You aren’t providing a way for customers to request or vote on new features.
  • You aren’t offering customers a way to quickly report bugs or following up with them when a bug report has been resolved.

Sign #4: Your Staff Are Burnt Out

Your staff are another set of voices you need to make sure you listen to. They are on the front lines patching code, fielding support requests, and trying to keep your investment running (as best they can).

Your team wants to be part of a positive experience for your customers. They also want and deserve to be able to take time off work without being called in to fix problems.

Here are a few warning signs:

  • They are expressing frustration at having to solve the same problems over and over again.
  • They are being called in when they should be off work because they are the only person that can fix “that one thing” that keeps breaking.
  • Likewise, you dread when that one person requests time off because you need them to fix those things.
  • There is an overall “vibe” that your staff has basically given up — they aren’t suggesting improvements anymore and are resigned to doing whatever they’re told.
  • Your employee turnover rate has increased — more employees are taking jobs elsewhere.
  • It’s taking longer than it should to onboard new employees — the old system is hard to understand, and it’s taking too long to get them up to speed.

Sign #5: Your Users Are Creating Hacks

We’ve already talked about how customers can be a clear voice when things aren’t working like they should. One of the more subtle ways they can communicate is by creating hacks or workarounds to make up for deficits in your features or bugs in your system.

There are a few ways to find out what they’re doing to make your system work:

  • Check any communities you’ve created for them, such as comments on user guides, Facebook Groups, Slack Communities, etc.
  • Check any user-created professional communities on LinkedIn or Reddit.
  • Do a search on sites like Quora for your software name to see what questions people are asking and how other people are guiding them.
  • Search your software name on Google and look for blog articles or videos where other users are making videos or writing up their favorite hacks.
  • Look for third-party plugins, APIs, Zaps, Stylish modes, themes, or other resources that people have made to customize your software.
  • Ask your customers what you could do better. You can do this with bulk surveys or have your customer support team reach out individually to talk to customers.

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.

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