When it comes to digital transformation projects, stakeholder expectations and aspirations can vary wildly from one group to another. For example, in a recent study, 53% of CIOs and CTOs said they see one specific technology—agentic AI—being core to IT operations within two years, but only 29% of IT practitioners feel the same way. That disconnect likely stems from a complex array of factors, but it clearly illustrates the differing perspectives of those who want the benefits of new technology solutions and those who are tasked with implementing and administering the technology itself.
To ensure all stakeholders are on the same page, your IT team must be deeply involved in developing a digital transformation project’s scope as well as its timeline. Without their input, you may face resistance from a group that’s central to the effort’s success. Consider these common digital transformation project schedule missteps that can arise from a lack of technology expertise and input.
Project timelines don’t accurately reflect the effort involved.
Executives often drive early project schedule development efforts, but even those well-versed in technology management frequently don’t understand the work levels and day-to-day actions necessary to deploy many of the latest platforms. Every system plays a role within the IT stack, but there are many factors that affect the project’s workload. How many new integrations are needed? Which features will be active based on our subscription tier or purchase level? Are there restrictions on those features related to cybersecurity measures or regulatory requirements? Since IT will be responsible for implementation as well as post-deployment user support, protecting against emerging cyber threats, and other tasks, many will push back on a proposed schedule until they can confirm it’s complete, realistic, and workable.
Schedules are driven by stakeholders who aren’t part of the project’s execution.
With multiple groups interested in your digital transformation effort’s results, balancing potentially competing expectations is a big part of creating a practical timeline. Board members, investors, or business partners may want to see early positive progress from an expensive technology project. Alternatively, IT could be more focused on having enough time to respond to calls and end user requests for help that come in during the rollout phase. Rushing toward an early milestone could throw frontline users into chaos, and IT will often resist committing to an aggressive timeline that sacrifices workflow stability and the end user experience.
The project schedule underestimates (or omits) necessary customization work.
Few modern technologies can drop into the enterprise without some modification. Understanding the customizations that are needed—and what’s involved in making those happen—is outside the experience of most business groups. Even IT leaders will likely need to conduct some research and assess the scope of potential changes before the team can provide accurate task duration estimates. Tailoring a solution to fit the organization’s needs may also involve testing, quality assurance activities, and preparing to maintain the customizations over time. Without adequate scheduling, this work can consume resources intended for other core IT tasks.
The project timeline doesn’t account for IT’s internal skill- and experience-building needs.
Technology tools are in a near-constant state of evolution, and the expertise to implement and administer one system doesn’t always translate well to a different system. Your IT group may not have had an opportunity to gain much expertise in deploying, managing, or monitoring the new platform the business wants to add. Along with knowing there are provisions within the project schedule to train and educate end users, your internal IT professionals will also want to be sure there’s adequate time for their own learning curve and skills development activities.
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