Series Three · May 2026

The Returns
on Technology.

Three essays. Approximately ninety minutes of reading. Twenty-four principles a CEO, COO or board member should be able to articulate in their own words — on how to think about technology spending, why most projects fail to produce returns, and how every classical investment principle is being rewritten by AI.

Why this series, why now

Most senior leaders cannot defend their technology choices when pressed.

Every CEO has a version of the same recurring conversation. The CIO presents a roadmap that runs into hundreds of crores. The CFO asks what the return looks like. Someone mentions AI. Someone else mentions technical debt. And underneath all of it sits a question that almost no one in the room can answer with real conviction — are we spending the right amount, on the right things, in the right way?

This series is an attempt to answer that question — not as a survey of frameworks, but as a working theory of how to think about technology investment in the AI era, distilled to twenty-four principles across three essays. The first is about the mindset. The second is about returns and execution. The third is about strategy itself. Each builds on the previous one.

Written for senior leaders who have noticed that the cost of getting this wrong has gone up — and that the firms quietly pulling away are the ones whose CEOs have changed how they think about this category of decision.

The Three Essays

Read in order

EP 01

The Mindset Decision

Eight principles on how to think about technology spending — before a single rupee is committed.

Posture, allocation, build-buy-partner, total cost of ownership, core versus context, the bottleneck principle, what shadow IT is actually telling you, and why foundations matter more than features. The upstream work that determines whether everything downstream compounds.

Key idea → The mindset is the foundation.

30 MIN READ 3,963 WORDS
EP 02

The Returns Reality

Why most technology projects fail to produce real returns — and what the firms that succeed do differently.

Why ROI is genuinely hard to measure. The J-curve and why CEOs kill good projects too early. Why most technology projects fail (and it is almost never the technology). The last-mile problem. Tech debt as a balance-sheet item. The talent multiplier. When to walk away. And the new mathematics of AI returns.

Key idea → Returns are leadership work, not technology work.

30 MIN READ 4,032 WORDS
EP 03

The Strategic Rewrite

Why every classical principle of technology investment is being rewritten by AI — and what that means for the next decade of leadership.

Technology strategy is business strategy. Platforms over products. Ecosystems and the leverage of partners. AI as cost reduction versus AI as reinvention. Why proprietary data is the moat. Human-in-the-loop economics. How big tech actually thinks. And the CEO's new mandate.

Key idea → Technology strategy is business strategy now.

30 MIN READ 4,198 WORDS

Technology is the work. The work is leadership. And leadership is harder than any of us were trained for.

— from Episode Three, MacSays
Also from MacSays

Series One & Two — Compounding and Structured Thinking

If The Returns on Technology is about how senior leaders should think about technology spending, the earlier MacSays series sit underneath it. Compounding is about productivity in the AI era — what AI is doing to individuals, teams and organisations. Structured Thinking is about the discipline that lets you do that thinking yourself, before, around and after the machine.

Read Series One — Compounding →

Read Series Two — Structured Thinking →