The Internet strategic plan

What this book actually teaches

Robert Boutin's book arrives at a specific moment — 1999, the peak of the dot-com build-out — and addresses a specific audience: business executives who understood that the internet was strategically important but had no framework for making disciplined decisions about it. The core argument is that internet initiatives fail not because of technology problems but because of planning failures: companies launch websites and e-commerce capabilities without defining success metrics, without integrating internet strategy with business strategy, and without a governance process for making ongoing resource allocation decisions. The book proposes a six-phase Internet Strategic Planning (ISP) framework as a corrective.

The six phases — Environmental Analysis, Customer Analysis, Competitive Analysis, Internal Assessment, Strategy Formulation, and Implementation Planning — map closely to a traditional strategic planning process adapted for the specific decision context of internet deployment. What Boutin adds to the standard MBA strategy template is a set of internet-specific analytical lenses: how to evaluate a company's existing technical infrastructure as a constraint on internet deployment speed, how to assess the digital literacy and change-readiness of the workforce, and how to set realistic timelines for capability development in an environment where technology is evolving faster than most annual planning cycles.

The environmental analysis chapter is the strongest section. Boutin identifies the structural forces shaping internet commerce in 1999 — falling access costs, rising consumer digital adoption, emerging payment infrastructure, evolving regulatory environment for data privacy — and shows how each creates different strategic implications depending on industry. For retail, falling access costs meant that customer acquisition economics were more favorable online than most traditional retailers had modeled. For financial services, evolving payment infrastructure created both opportunity and risk depending on timing. The framework for reading these environmental signals is more durable than the specific 1999 examples.

The customer analysis chapter introduces a segmentation approach that holds up well: rather than segmenting by demographics, Boutin segments internet customers by their digital behavior and technology comfort level — early adopters, pragmatist adopters, and laggard adopters — and maps different service strategies to each segment. This maps loosely to Geoffrey Moore's technology adoption lifecycle framework and is more actionable than demographic segmentation for decisions about which features to build first and at what technical sophistication level to pitch the user experience.

The implementation planning section has aged the most poorly. The specific technology recommendations (network architecture choices, content management system selection criteria, e-commerce platform evaluation) reflect a world of technical constraints that no longer exist — cloud infrastructure, SaaS platforms, and API-first architecture have eliminated most of the build-vs-buy and infrastructure decisions Boutin addresses. These chapters are historical documentation rather than current guidance.

For small business owners in 2026, the durable value is in the planning discipline Boutin advocates, not the specific internet content. The argument that digital initiatives require the same strategic rigor as any other major capital decision — defined objectives, explicit assumptions, measurable success criteria, governance for ongoing resource allocation — is as relevant for AI tool adoption, platform expansion decisions, and digital marketing investments today as it was for website launches in 1999. The framework translates.

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About Martin A Schulman

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