Top Mistakes to Avoid When Upgrading Business Software

For enterprises running on outdated software platforms, system upgrades inevitably become necessities rather than choices. As technology progresses and vendors stop supporting older tools, these naturally become outdated. Staying stagnant is simply not an option if a company wants to remain competitive, compliant, and secure.

But just because software upgrades prove unavoidable doesn’t make them simple or risk-free endeavors. Even minor oversights or mistaken assumptions can snowball into debacles. Vigilance against common pitfalls represents the best insurance policy against upgrade calamities.

Don’t Skimp on Up-Front Discovery

More upgrade initiatives derail from insufficient preparation than perhaps any other factor. Businesses that underestimate the effort and complexity of projects do so at their own risk.

The key lies in thoroughly auditing every nook and cranny of the existing software ecosystem first. Account not just for core applications, but ancillary integrations, report requirements, data sources, workflows, third-party add-ons, and more. Identify customizations to migrate and technical debt to mitigate too.

Only by achieving complete current-state visibility can teams properly size subsequent upgrade efforts, timelines, and resources. If you rush the planning phase, you risk going over budget and falling behind schedule due to missing some important details.

Engage the Right Stakeholders, Experts Early

Upgrades inevitably create widespread reverberations across organizations. Business processes, access needs, reporting demands all face upheaval that nobody can ignore.

Yet all too often, companies still treat upgrades as insular IT projects rather than collaborative business endeavors. Not looping in impacted users and stakeholders until late is a massive mistake.

The involvement of external experts, like those at ISG, proves equally pivotal for major upgrades too. Trusted software advisory services help set realistic expectations, evaluate alternatives, build business cases, and optimize implementations. Attempting disruptive transitions without that expert guidance breeds uncertainty and missteps.

Don’t Underestimate Data Complexities

Migrating decades of accumulated business data into new systems seems straightforward enough in theory. In reality, data wrangling frequently represents the hairiest, most problem-prone aspect of end-to-end upgrades.

Common landmines include data mapping challenges, missing integrity, corrupt records, and incompatible formats. Even fundamental architecture shifts like transitioning from on-premises to cloud infrastructure muddy the migration waters. Overlooking any of those data complexities can corrupt upgraded systems on Day 1.

Adequate preparation absolutely requires exhaustive data profiling. Inspecting data quality and compatibility enables proactive mitigation plans rather than scrambling reactively later.

Embrace Comprehensive Testing Protocols

Software quality assurance often represents an organization’s single greatest investment during major upgrades. And with good reason; shoddy system testing virtually guarantees nightmarish stakeholder experiences post-implementation.

Proper testing goes far beyond simply ensuring new software “works” from a technical perspective. It delves into areas like security, performance under load, role-based user stories, reporting accuracy and workflow nuances. Teams should thoroughly evaluate all features so as not to release any unstable code into production.

Don’t Skimp on End User Training

Another brutally expensive upgrade mistake is assuming end users can immediately adapt to new software with little to no training. That unfounded optimism virtually guarantees adoption struggles, process bottlenecks, and squandered transformation investments.

Instead, enterprises must approach training with the same vigor as implementation planning. Identify specific training needs across roles and departments first. Develop tailored curriculums and delivery strategies for resonant knowledge transfer, and maintain readily available resources for reinforcement.

Conclusion

At first glance, enterprise software upgrades simply look like mere technical transitions from legacy tools to newer versions. But scratch just beneath the surface, and their true stakes become abundantly clear.

When executed flawlessly, upgrades catalyze transformed efficiencies, competitiveness, and strategic advantages. But when mismanaged, companies needlessly squander time, money, productivity, and sometimes even their entire future viability.

Organizations willing to invest proper upgrade governance reap the full benefits rather than suboptimal deployments. Their thriving enterprises will appreciate those foresighted efforts.

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