Technology Strategy Patterns

Technology Strategy Patterns by Eben Hewitt

Overview

Technology Strategy Patterns provides architects and senior engineers with practical frameworks for aligning technical decisions with business strategy. Eben Hewitt presents battle-tested patterns for creating technology strategies that drive real business value.

Key Highlights

Core Principles

• Strategy is not a plan - It’s a framework for making consistent decisions under uncertainty
• Technology strategy must serve business strategy - Never build tech for tech’s sake
• Patterns over prescriptions - Reusable approaches beat one-size-fits-all solutions
• Communication is half the battle - Technical leaders must translate between business and engineering

Essential Patterns

1. The North Star Pattern

• Define clear technical vision that aligns with business goals
• Use it to evaluate every architectural decision
• Communicate it relentlessly to maintain alignment

2. The Options Framework

• Always present multiple viable options with tradeoffs
• Quantify costs, risks, and benefits for each
• Make decision criteria explicit and business-aligned

3. The Strangler Fig Pattern for Migration

• Incrementally replace legacy systems without big-bang rewrites
• Reduce risk while maintaining business continuity
• Particularly relevant for Staff+ engineers leading modernization

4. The Technology Radar

• Categorize technologies: Adopt, Trial, Assess, Hold
• Keep teams aligned on what to use and what to avoid
• Update regularly based on learning and market changes

5. The Architecture Decision Record (ADR)

• Document why decisions were made, not just what
• Capture context that will be lost over time
• Create institutional memory for future engineers

Practical Takeaways

For Staff Engineers:

• Your job is to reduce uncertainty for the organization through better technical decisions
• Build optionality into systems - future you will thank present you
• Write strategy documents that executives can understand and act on
• Use patterns to communicate complex tradeoffs clearly

Strategic Thinking Skills:

• Ask “what business outcome does this enable?” before every technical decision
• Think in time horizons: 6 months, 18 months, 3+ years
• Identify constraints early - they shape possible solutions
• Build coalitions around technical initiatives before announcing them

Common Pitfalls to Avoid:

• Creating strategy documents nobody reads or follows
• Optimizing for technical elegance over business value
• Making irreversible decisions when reversible ones would work
• Failing to measure whether strategy is working

Quick Facts

• Target audience: Architects, Staff+ engineers, technical leaders
• Key insight: Technology strategy is about making better decisions faster, not creating perfect plans
• Best chapter: “Making Strategy Real” - bridges gap between documents and execution
• Practical tool: The Strategy Canvas for visualizing competitive positioning
• Time to read: 8-10 hours
• Shelf life: Patterns are timeless, examples age well

When to Apply This Book

• Stepping into Staff/Principal engineer role requiring strategic thinking
• Leading major technical initiatives (migrations, modernizations, new platforms)
• Struggling to get buy-in for technical proposals
• Needing frameworks to evaluate competing technical approaches
• Building long-term technical roadmaps aligned with business

Bottom Line

Technology Strategy Patterns fills a critical gap between pure technical books and pure business strategy books. It gives senior engineers the vocabulary and frameworks to operate effectively at the intersection of technology and business - exactly where Staff+ engineers live. The pattern-based approach makes it immediately practical while remaining broadly applicable across different organizations and technical contexts.