November 17, 2025
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Why every failed digital transformation is a human story

Companies keep writing big cheques for digital change. Yet the payoff often eludes them: when projects stall, it is rarely because the code is bad. As Shaswat Kumar, SVP Customer Success & Delivery at Darwinbox, framed it in his conversation with Pushkar Bidwai, CEO of People Matters on the Humanscope podcast, “Human failures were leading to failures of all these digital programs.”

That observation explains a stark industry fact: around 70% of transformations do not meet their objectives.

The human side of failure

What does “human failure” mean in practice? It shows resistance to new ways of working, fragmented communication between people and teams, and a lack of trust in leadership to protect employee welfare while change happens. These problems turn technology rollouts into theatre rather than business outcomes. 

Even with sophisticated digital tools, human alignment remains critical. CHROs in SEA report that 40–45% of HR functions still rely heavily on human intervention for critical processes such as C-suite collaboration, executive compensation, and HR team capability development, illustrating how execution often falters when human readiness lags behind technological ambition.

The CEO’s mandate: Non-negotiable

Successful transformation is rooted in top-down ownership. Without CEO sponsorship, even the most sophisticated platforms or processes rarely succeed. As Kumar puts it, “If that buy-in is not there, don’t waste your time.”

The stakes are high: 78% of CEOs expect CHROs to advise on strategic transformation and future readiness, yet gaps in execution and alignment leave many initiatives underdelivering. When leaders anchor transformation to measurable business outcomes like revenue impact, customer retention, faster product cycles, HR moves from the sidelines to the centre.

Start small, scale smart

Across industries, digital leaders are adopting a “small wins, big scale” approach: beginning with tightly defined problems and scaling once early impact is proven. Technology acts as an amplifier, not a cure-all. As Shaswat notes, “Tech will accelerate it. Tech will allow you to do it at scale, but you need to first understand the problem, what solution is ideal, and then enable it with tech.”

In India today, cloud and AI are shifting the calculus: two-thirds of enterprises are migrating applications to the cloud and many see cloud as a primer for AI adoption, while Indian employees are among the fastest to adopt generative AI tools at work. 

Making the value visible

Business leaders are also recognising the importance of linking transformation to financial outcomes. Quantifying ROI—whether in hours saved, revenue per employee, or productivity gains—creates credibility across the C-suite. Reports also note that 61% of HR leaders cite difficulty justifying HR tech ROI and value realization, and 42% struggle with system integration and adoption support, underscoring the fact that measurement is critical to securing executive buy-in. As Kumar emphasises, “Let’s close that value case with the CFO because that keeps everyone honest.”

When HR and finance collaborate to define clear success metrics, transformation becomes a business initiative rather than a technology project.

Funding the work of change

For leaders in India and beyond, the lesson is clear. Fund the technology, yes, but first fund the work of change: mandate from the top, measurable ROI, clear people-centred design, and a partnership of HR, IT and finance. That is how digital projects stop being IT projects and become business accelerators.