Why 65% Of Digital Transformation Initiatives Fail & How Enterprise Strategist Aneesha Sharma Bridges The Gap

Why 65% Of Digital Transformation Initiatives Fail & How Enterprise Strategist Aneesha Sharma Bridges The Gap

Digital transformation faces a funding gap as only 35% of organisations achieve goals despite heavy investments. Misaligned success metrics between executives often block measurable ROI. Expert Aneesha Sharma highlights that linking technology to clear financial outcomes, governance frameworks, and phased execution is key to turning digital strategies into funded, scalable business initiatives.

Neehal KumarUpdated: Thursday, March 05, 2026, 01:37 PM IST
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Aneesha Sharma |

Digital transformation faces a funding paradox: 72% of CEOs report having aggressive digital investment strategies, yet only 35% of organisations achieve transformation objectives. Deloitte's 2025 research identifies the breakdown point—CFOs, CIOs, and CTOs define success through incompatible metrics. A project succeeds technically but fails to demonstrate financial impact. Operations improve efficiency without moving customer metrics. Value gets created but isn't recognised in ways that secure continued investment. For Indian enterprises, this challenge intensifies as they navigate both international technology ecosystems and domestic regulatory frameworks. For them, DPDP compliance and data localisation requirements create additional measurement dimensions where technology success, financial returns and adherence to regulatory demands must all demonstrate value simultaneously. 

Aneesha Sharma, who serves as Technical Account Manager  at YASH Technologies  and a fellow member of Hackathon Raptors, specialises in preventing this gap between technology investment and ROI realised. As Proposal Specialist at Honeywell, she brought business worth $60M by translating client requirements into end-to-end industrial automation solutions that help customers unlock value in their environment and meet their business objectives. As Senior Advisor in Dell Technologies' Corporate Strategy Office, she developed pan-Dell cybersecurity strategy, identifying a $3 billion opportunity in the Zero Trust market - these opportunities are commercialised as Dell's security offerings even today. At YASH, she is helping create value based offerings for the market while also improving internal governance structures that offer the CEO's office visibility into year over year internal investments. She has consistently translated business vision and strategy into measurable impact throughout her career. Her work, translating business vision into measurable impact, earned her the 2024 Indian Achievers Award’ for Outstanding Professional Achievement and Contribution toward Nation Building. 

You've worked at three major global technology companies, namely Honeywell, Dell Technologies, and YASH Technologies, helping translate technical capabilities into business outcomes. From your experience working across corporate strategy, what is actually preventing organisations from bridging this gap between technology investment and measurable business value?

The gap occurs when organisations approach technology adoption without the strategic foundation needed to sustain it. They may have an elaborate digital transformation roadmap or a sophisticated security architecture, but there are multiple issues that can prevent execution: they're not addressing the right operational or technical challenges, they lack the ability to prioritise due to limited visibility or fragmented decision-making, or they haven't tied current initiatives to their broader three-year strategic horizon. Without business models and financial justification frameworks connecting these elements, technology investments won’t translate into high value programmes.  

Companies that can articulate what they want to build in the language of business value, including revenue impact, competitive positioning and cost efficiency, can realize returns on their technology initiatives. Moreover, measurement fragmentation creates additional issues when the metrics introduced by executives do not align. As a result, an initiative can succeed in one dimension but fail in another. Without governance frameworks that establish shared definitions of success across all stakeholder groups, organisations end up with what I call perpetual pilots — technically sound initiatives that never scale because no single executive can make the business case for enterprise-wide investment.In my academic research, I'm exploring why AI pilot projects specifically stall, examining this through consumer behaviour research lens to understand the psychological and organisational factors that trigger disengagement even when the technology performs well.

Looking across your work at Honeywell winning major automation contracts, Dell commercialising the Zero Trust framework into solutions still used today, and YASH where you're converting strategic partnerships into actual customer wins, one can see a common thread beyond the different industries and technologies. You seem to specialise in moving things from concept to funded execution. What separates the initiatives that make that leap from the ones that don't?

There are three things that separate funded initiatives from those that stay conceptual. First, they have financial models that establish connections between technical investments and specific business outcomes, not abstract claims. For instance, at Honeywell, winning $60 million in automation contracts required showing clients how automation investments translated to operational efficiency and risk mitigation in measurable terms. Second, successful initiatives have clear implementation roadmaps that focus on milestones, internal alignment and defined roles and accountability mechanisms, rather than grand visions. And third, they are designed to align with how decisions are actually made in an organisation. Working on Microsoft alliance strategy at YASH required creating value based offerings and GTM roadmap that align with Microsoft's co-selling criteria, YASH partnership goals and Microsoft’s vision for its partners. You can say that to succeed, initiatives should be aligned with company strategy and operational reality, not just technical elegance.

Let's explore your work at Dell's Corporate Strategy Office in more detail. There, you developed Zero Trust strategy and identified approximately $3 billion in market opportunity. What did you learn about building frameworks that executives will actually fund rather than keeping security initiatives stuck in pilot mode?

The Zero Trust initiative succeeded because it addressed a business need with clarity. In general, successful frameworks integrate four elements that executives need to make investment decisions: market intelligence signaling clear demands, Dell’s ability to address these demands through internal capabilities, financial modelling demonstrating clear returns with risk models factored in and internal operational alignment on who does what. What prevented the Zero Trust initiative to stall was clearly defining all these components - for example mapping industry mandates and enterprise risk profiles to security control layers, and then aligning those requirements to Dell's internal IP. This mapping helped us identify opportunities that could be deployed immediately without waiting for some future state. 

Both at Dell and at YASH, you've worked on strategy frameworks that determine investment prioritisation and executive review processes. What does an effective strategy structure actually look like when you need to get a board to approve a multi-million dollar cybersecurity or digital transformation investment?

An effective strategy for board approval is a decision framework that connects business risk, financial return, and execution realism. At Dell, we started with quantifying the market opportunity and threat landscape, estimating parameters such as regulatory risks and shifting customer demand toward compliance-ready security offerings. The data were then translated into concrete investment opportunities presented with concrete product roadmaps and measurable KPIs, such as predicted sales in each sales channel. 

The same principles were applied to digital transformation investments at YASH. Effective strategy is the one that helps leadership to understand where to place the big bets, which services to grow and how to invest in capability building. We use structured prioritisation models to balance quick wins with long-term goals, while ensuring both are aligned to broader vision. 

In short, effective strategy for executive approval is not about ambition — it’s about clarity, credibility, and prioritizing the right areas to focus on. What consistently works with executive board is: a clear business problem grounded in market data, quantified financial case showing growth with risk mitigation, a phased execution plan with clearly defined owners and milestones, and clearly defined success metrics. 

Throughout your career, you've also evaluated professional work formally, as an auditor of Dell’s enterprise dashboard initiative, as evaluator of engineering team deliverables, as jury member for YASH’s internal marketing campaign assessments, and as a judge at the American Business Expo Award, a prestigious international competition bringing together over 1,000 entrepreneurs and investors. So I'm sure you've seen many approaches to digital transformation and business strategy. When you are evaluating a strategy or initiative, what distinguishes the ones that deserve investment and deployment from the ones that should stay on paper?

Whether I am auditing an internal initiative at Dell, where I evaluated a business intelligence dashboard used for portfolio related decisions across the organisation, or assessing more innovative solutions like the entries for the American Business Expo Award, I'm looking at three key components. First, innovation should solve the right problem that someone will pay to fix. Technical elegance doesn't matter if there is no commercial demand or if organisations are not prepared to integrate it to their environment. Second, the solution should have a realistic path from the current state to the deployed state. If the solution requires addressing multiple criteria simultaneously, for example, obtaining regulatory approval, restructuring processes, and changing organisational culture, it will not work. Third, the efficiency of the solution should be measured in ways that matter to the people using the solution. Strategies often fail when activity is confused with outcomes. Activities tell you how many people will be trained or how many new systems will be integrated, but do not summarise if those skills are relevant in bringing in revenue for your company or how these skills improve your customer experience. 

These are the criteria I consider consistently across different evaluation contexts.At Dell, I was appointed as the auditor for a strategic enterprise dashboard initiative that is used to gather market intelligence and inform portfolio level decisions. At Honeywell, I have also evaluated engineering team deliverables, ensuring technical solutions proposed are aligned with customer requirements and Honeywell’s operational standards. At YASH, I have reviewed internal marketing campaign content and structure, ensuring alignment of leadership vision with marketing messaging. And in December 2025 I evaluated innovative solutions at the American Business Expo Award, applying the same lens to assess whether these innovative solutions could translate from concept to business value.

What is the first thing that an enterprise leader should do differently to get their digital transformation initiatives approved and brought into practice?

The first thing leaders must change is how they frame digital transformation. Instead of presenting transformation through technical specifications or system replacements, present it as a quantified business investment tied to revenue growth, cost efficiency, and risk reduction. Boards approve business value, so successful initiatives begin with a clear financial case showing measurable impact and a clear path to value. 

Moreover, breaking transformation into stages with early wins reduces perceived risk and builds momentum. Demonstrate value in short-term increments instead of requesting approval for a large-scale overhaul, ensuring that each phase delivers measurable results that can help secure the next round of investments. In addition, leaders should frame inaction as the bigger risk, demonstrating that in the current competitive and regulatory environment standing still means losing market position. 

At Dell, I saw multi-million-dollar cybersecurity investments gain board approval only after we translated Zero Trust security initiatives into clear revenue opportunities, with risk mitigation factored in. We presented to executives how these investments would enable sales into new industry segments that were previously inaccessible, enable us to keep our market leadership position and how we can help our customers with new regulatory demands.  Similarly at YASH, digital platform and AI modernisation initiatives were approved when we clearly defined how it can bring value to our customers, our partner ecosystem and can be deployed using existing capabilities in a phased delivery model with clear milestones. 

Ultimately, the question isn't whether to invest in a digital transformation — it's enabling organisations to prioritize the right initiatives, help execute them and realize returns. The organisations mastering this strategic vigour aren't necessarily the ones with the biggest budgets or the most advanced technology tools. They're the ones with clear vision supported by financial structures and cross-functional alignment that turn strategic intent into funded reality.