Your initiative launched with great expectations. Now it’s falling apart in front of your eyes. What should you do next?
Every digital transformation initiative starts with high hopes and great expectations. Then, for many CIOs, reality hits hard. What was once a promising plan to modernize products, processes, operations, and the technology stack, suddenly begins careening off the rails.
Now the digital transformation must be delayed, adapted, reconfigured, or perhaps even scrapped altogether. If only the CIO had seen the warning signs and used those indicators to take the steps necessary to get the initiative back on course.
Is your enterprise’s digital transformation initiative succeeding, circling the drain, or simply in need of some well-planned adjustments? To find out, pay attention to the following signs of a digital transformation gone awry.
1. There’s no tangible business value
It’s not about delayed timelines or budget overruns, which can be part of any complex project, says Trevor Young, chief product officer with cybersecurity product and services firm Security Compass. “It’s a fundamental disconnect where the technology being implemented simply isn’t delivering the promised improvements to operations, customer experience, or competitive advantage.” This indicator, he notes, often reveals itself as a growing cynicism within the organization, with teams feeling like they’re simply “doing digital” for its own sake without a clear understanding of the “why” or seeing any real positive impact.
Young believes that the best way to detect this failing is by conducting regular honest assessments, including examining key performance indicators (KPIs). “Look for stalled adoption rates of new tools, continued reliance on old processes despite new systems, and a general decline in cross-functional collaboration around the transformation goals,” he suggests.
Young also recommends conducting candid feedback sessions with both end-users and middle management. “If they express frustration, confusion about the purpose, or a feeling that the new systems are making their jobs harder rather than easier, those are strong indicators.”
2. Goal misalignment
When users aren’t interested or feel no need to use the transformation’s new tools or applications, it indicates a disconnect between the users, their goals, and actual business outcomes, says Aparna Achanta, IBM Consulting’s cybersecurity strategist and AI governance and transformation leader.
To successfully address this issue, Achanta recommends aligning digital transformation with the overall business vision, making sure that the voices of end-users and customers are being heard. “It’s [then] important to deliver the tools and streamline the processes and use cases that need to be re-designed.”
Roll out the transformation’s tools and applications one by one, as opposed to rolling out all everything all at once, Achanta advises. “Tool fatigue can lead users to not adopting the new tools for their day-to-day tasks,” she warns. Additionally, role-based training will help users better understand how the new tools and applications can be used to their benefit.
Pratik Mistry, executive vice president at Radixweb, an AI and data consulting firm, sees misalignment also often appearing as “digital busy work,” lacking any potential for measurable wins. Stakeholders soon become disillusioned. Momentum stalls.
“Everyone’s working hard, but nothing’s really changing,” he says. “You’ll see teams focusing on features over impact and platforms over processes.”
As soon as goal misalignment is detected, pause and realign, Mistry advises. “Strip away the noise and return to the core.” Reconsider the initiative’s intent. “Then re-evaluate every sprint, every integration, every dollar, against that original goal.”
3. Business leader indifference
Chatter from the right people has always been the best transformation health indicator, says Steve Hochman, managing director for North America at engineering and technology consulting firm Nagarro. “If the coolest and most influential senior business leaders in your organization aren’t actively talking about your project, it’s a warning sign that your transformation may be doomed.”
Strong business leadership, and a willingness to admit mistakes, are essential to digital transformation success, Hochman says. “Too often, enterprises run away from failure.” He notes that such moments are actually golden opportunities to break paradigms and try new approaches. “The more failures a company speaks openly about, the more innovation occurs.”
4. Poor leadership
Digital transformation requires strong leadership focus and a sense of sponsorship and championship, says Ola Chowning, a partner at technology research and advisory firm ISG. “Transformations have both technology and people/process-oriented outcomes and implications, so initiatives should be communicated broadly and often to continually reinforce the vision, expectations, and progress.” Inconsistent communication from leaders, a lack of reporting on progress or results, missed or declining management metrics, and poor customer or team feedback can all point to a lack of leadership focus, she adds.
Chowning believes it’s vital to review the overall initiative to revalidate its vision and priority. “A form of reboot may be required to achieve the appropriate sponsorship from leadership that’s critical to transformation initiatives,” she states. “If the review reveals that the initiative is no longer a priority, or that the scope or vision needs a serious revamp, it may be best to abandon the initiative.”
5. End-user indifference
You built a shiny tool, migrated to a new system, and conducted perhaps three weeks of training, yet if usage drops 40% you’re not transforming, you’re simply decorating, warns Toby Basalla, principal data consultant at data consulting firm Synthelize. “Adoption is the oxygen of transformation,” he says. “If your people are still working in spreadsheets while your digital platform gathers dust, you’re done and just have not said it out loud yet.”
Decay can be detected faster than most teams think, Basalla says. “Start with logins [and] pull the usage stats,” he suggests. “If less than 20% of the intended users are in the system daily, something’s broke.” Perhaps the system is too slow, or the workflows don’t fit users’ needs. “Either way, it’s not getting used, and pretending otherwise just wastes everyone’s time.”
To reverse the slide, Basalla recommends cutting the fluff and focusing on a single flow. “Find the process with the biggest pain-to-payoff ratio and fix that first,” he advises. “If a digital tool saves someone time, they will use it, but if it takes 10 extra clicks to do the same task they were doing in Excel, it’s a hard no.” People, Basalla explains, vote with their time.
6. Faulty execution
Digital transformations often falter due to a lack of disciplined execution or insufficient focus and commitment from the top of the organization, says Karthik Krishnamurthy, chief transformation officer and CFO at Smith and Howard, a tax, accounting, and business advisory firm. Without strong executive sponsorship, it’s difficult to sustain momentum, he observes. “You’ll begin to see key deadlines slipping, results falling short of expectations, and diminishing engagement — especially from senior leadership.”
Krishnamurthy recommends periodically validating the transformation’s original assumptions and benefits to see whether they’re still relevant. “If they are, it often comes down to re-engaging leadership,” he says. “When a CEO or business unit leader actively owns the initiative — tracking progress daily or weekly — the organization typically responds, and momentum can be regained.”
If the initial assumptions no longer hold true — due to shifts in either the enterprise’s priorities or the external environment — it may be time to walk away, Krishnamurthy advises. He also believes that it’s okay to pause a transformation if its resources can be better used elsewhere. “What’s critical is clearly communicating the ‘why’ behind the decision, or teams will lose faith and start believing that ‘we chase trends but never finish anything.’”
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