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Forbes - Innovation

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How To Avoid The Common Headaches In Software Migration
Thomas Bernd · 2026-05-15 · via Forbes - Innovation

Thomas Berndorfer is the CEO of Connecting Software.

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​IT professionals often dread the task of migrating software—an undertaking that can require months, if not years, of work and the difficult job of gaining cultural buy-in from staff.

Migrations like these happen for many reasons—new apps and systems might have a better business case because of technological edge or cost, alternatively, a merger or acquisition might mean that new staff have to be brought into alignment with the broader company.

Misaligned systems can immediately cause problems between processes, departments and new acquisitions. When one side uses Microsoft and another uses Google, files might be saved in different formats and useful functions might not exist on a colleague’s machine. These small inconveniences can cumulatively lead to inefficiencies and breakdowns in collaboration.

It’s easy to see why companies would therefore want to migrate their systems to have greater alignment, but that is certainly easier said than done in many cases. Recent surveys show that companies with 750-1499 employees use about 116 different SaaS apps, with complex layers of interdependencies that make change difficult and frustrating.

This is especially true when companies try to integrate SaaS apps with on-prem systems (about 25% of apps) or integrate across departments within large companies, which often have subtly different yet distinct setups. These webs of interdependency can lead to unexpected consequences when one program is changed—if a company were to change its backend website technology, for instance, it might find that the data it provides to its sales pipeline is no longer compatible.

Famously, many migration projects end up in some sort of failure—behind schedule, over budget, incomplete or abandoned. In many cases, it’s because migrations can create more than their fair share of unexpected issues.

Why Migrations Generate Headaches

One of the most damaging aspects of migration happens in the human aspect of the business. If companies handle migrations poorly, creating frustrating or inefficient processes for straightforward tasks, morale can suffer.

In some companies, employees resent the training meetings and new habits that are frequently necessary with software migrations. Inevitably, when employees are given roadblocks to doing their job effectively, many will consequently reach for forms of Shadow IT or unauthorized workarounds, that can create new security vulnerabilities.

Tech migrations will involve some degree of a learning curve at best, but in the worst circumstances, can result in months of lost productivity across the organization. Especially when you are asking employees to migrate over from dozens of applications, sales slow down, collaboration between teams might decrease and businesses can make poor decisions without reliable data to base them on (which can be especially fatal during Enterprise Resource Planning). Even small decreases in aggregate efficiency can kill companies.

How To Avoid These Headaches

Often, the greatest headaches during software migration are more to do with the approach than the software itself. Poor execution on the people or technological management side tends to create the problems we often see.

For instance, faced with the decision of a burdensome migration, businesses avoid the issue entirely, allowing different parts of the company to work with the systems they’re more comfortable with. This tends to bring headaches of its own due to misaligned systems.

Similarly, a “take it or leave it” solution where everyone is asked to use a new program can make things less complicated and avoid costs, but without tech support and company buy-in, can lead to inefficiencies, reductions in morale and the growth of Shadow IT. To avoid headaches here, it's important to have a well-thought-out internal communications strategy and strong internal management that helps employees feel more comfortable, as well as allowances for the learning curve it might take for employees to get used to it.

An alternative to this approach combines the strengths of both while eliminating some of the weaknesses: co-existence. With current technology, it's possible to have two different systems (like Google Workspace and Microsoft 365) automatically and bidirectionally synchronize with each other, meaning any change in one is automatically reflected in the other. Crucially, coexistence also directly addresses the data migration challenge—while employees continue working in familiar systems, data can be migrated in the background without operational disruption, reducing risk and enabling a more gradual, controlled transition.

This allows employees to retain the systems they are comfortable working with while also enabling increased internal collaboration. This gives employees that crucial time window to adapt to new processes, opening the possibility of a longer-term migration of systems down the line. The middleware layer adds a useful audit trail, making it easier to spot where workflow or data inconsistencies are happening during the transition.

This approach won’t work for some programs, given that not all are mutually compatible, and it will still require some degree of mutual adaptation on both ends of the business. Particularly given that some useful features will be available on one but not the other. But in our experience, many businesses benefit from a middle-ground strategy that maximizes compatibility while minimizing disruption.

Regardless of the approach, organizations always benefit when migrations and transitions are well planned and communicated. Smart leaders use available tech to make transitions easier for their companies and employees.

Conclusion

Tech migrations will likely always be dreaded by IT professionals, but they don’t always have to be so nerve-wracking. The key to managing these transitions is to avoid neglecting either the human or the technological side.

Migrating software must be clearly and consistently communicated to a company's employee base, and both leaders and managers must adapt their plans to their colleagues' technological skills. Companies can’t expect major change to happen overnight.

Managing the process technologically can be a significant benefit, with configurations allowing some degree of coexistence between programs, providing a much greater window for change. ​


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