The CRM works. Kind of. The interface feels old. There are workarounds everyone knows. Nobody remembers why certain things are configured the way they are.

But replacing it seems painful. So you keep going.

This is where most businesses live with their aging software. Not broken enough to force action. Not good enough to feel right.

Let me help you think through whether it’s time for change.

The Five-Year Assessment

Software that’s been in place for five years deserves a formal review. Here’s the framework.

1. Vendor Trajectory

Is your vendor investing in the product or milking it?

Signs of investment:

• Regular feature releases
• Modern interface updates
• Growing customer base
• Strong roadmap communication

Signs of decline:

• Minimal updates
• Dated interface never refreshed
• Customer churn
• Acquired by private equity (often precedes milking)
• Support quality declining

If your vendor is clearly in decline, start planning your exit regardless of current satisfaction.

2. Market Evolution

What’s happened in your software category since you chose this tool?

• New entrants with better approaches?
• Major platforms (Google, Microsoft, Salesforce) entering the space?
• Integrations and ecosystems shifting?
• Pricing models changing?

If the category has evolved significantly and you’re on an older solution, you might be missing meaningful capability.

3. Business Fit

Has your business changed in ways that strain the software?

• Significant growth in users or data volume
• New products or services the system wasn’t designed for
• Changed processes that require workarounds
• Acquisitions or partnerships requiring different capabilities

Software that fit perfectly five years ago might be a poor fit for today’s business.

4. User Experience

Do your people like using it?

Gather actual feedback. Not “do you want new software” (everyone says yes). Instead:

• What takes too long?
• What’s frustrating?
• What workarounds have you created?
• What do you wish you could do?

Frustration is costly. Not just in productivity, but in morale and adoption.

5. Technical Health

Is the underlying technology aging out?

• Browser compatibility issues
• Mobile experience poor or nonexistent
• Integration capabilities limited
• Security features outdated
• Performance degrading

Old technology creates real risk. And some things can’t be fixed by the vendor.

The Keep vs Replace Analysis

Once you’ve assessed, make a decision.

Calculate the Cost of Keeping

Direct costs:

• Current licensing
• Support and maintenance
• Workaround time (estimate monthly hours)
• Integration limitations (manual work that could be automated)
• Training new staff on outdated interface

Opportunity costs:

• Features competitors have that you don’t
• Productivity gaps
• Data you can’t access or analyze

Calculate the Cost of Replacing

Direct costs:

• New licensing
• Implementation (3-12 months typically)
• Data migration
• Integration rebuilding
• Training
• Parallel running period

Hidden costs:

• Productivity dip during transition
• Staff resistance and frustration
• Things that don’t transfer perfectly
• Risk of implementation problems

Compare Honestly

If keeping costs $50,000/year (including opportunity costs) and replacing costs $100,000 one-time plus $40,000/year ongoing, you break even in year three.

But if replacing costs $100,000 and saves $100,000/year, that’s a different story.

Run the numbers with realistic estimates.

When to Definitely Replace

Some situations demand action:

Vendor shutting down or discontinuing product. You’re on a timeline whether you like it or not.

Security vulnerabilities. Old software that can’t be secured creates real business risk.

Compliance requirements. New regulations requiring capabilities your software can’t provide.

Critical limitations. Business can’t execute strategy because of software constraints.

Staff revolt. When talented people are leaving partly because of frustrating tools.

When to Definitely Keep

Some situations favor staying:

Recent major investment. If you implemented or upgraded in the last 2-3 years, ride it out longer.

High switching cost, low pain. If the software basically works and switching is extremely expensive, optimize what you have.

No clearly better option. If alternatives aren’t obviously better, why switch?

Major business change coming. If you’re about to be acquired, reorganize, or pivot, wait until dust settles.

When It’s Genuinely Unclear

Most situations are ambiguous. The software is OK. Alternatives might be better. Switching is work.

Here’s what to do:

Evaluate alternatives properly. Not casual browsing. Real demos, real comparisons.

Pilot if possible. Some tools allow limited trials. Test with real work.

Talk to reference customers. Specifically those who migrated from your current platform.

Create a migration plan. Even if you don’t execute it, planning reveals true costs.

Set a decision deadline. “We’ll decide by March 1.” Prevents endless deliberation.

The Modernization Alternative

Sometimes you don’t need to replace, you need to modernize.

• Integration layer to connect with newer tools
• Workflow tools on top of legacy systems
• Custom interfaces improving user experience
• Data warehouse pulling data out for better analytics

This approach extends life of the core system while addressing specific pain points.

Works best when the core system is solid but specific capabilities are lacking.

Making the Decision

After assessment:

1. If vendor trajectory is poor or technical health is declining, prioritize replacement
2. If business fit is the issue, replacement probably makes sense
3. If user experience is the main pain, consider modernization first
4. If costs are close, often favor new (it’ll keep improving while old won’t)
5. If costs strongly favor keeping, optimize and reassess in two years

The Implementation Reality

If you decide to replace, do it right:

• Allocate adequate budget and time
• Get executive sponsor and dedicated project owner
• Involve users in selection
• Plan migration meticulously
• Train thoroughly
• Don’t rush the cutover

A failed implementation makes things worse, not better.

The Bottom Line

Five-year-old software isn’t automatically obsolete. Sometimes it’s still the best choice.

But five years is long enough that a thorough review is warranted. The landscape changes. Your business changes. The software might not have kept up.

Do the assessment. Run the numbers. Make a deliberate choice.

Then either commit to the current system for another few years or commit to a proper replacement. The worst outcome is limbo: knowing you should change but never acting.