🐟 Analogy
David Foster Wallace’s parable: two young fish swim past an older one who says, “Morning, boys, how’s the water?” One turns to the other: “What the hell is water?” Technologists live inside business so completely that they can’t see it. Technology strategy is learning to see the water — a hammer doesn’t exist to be a hammer; technology exists to build a business.
Eben Hewitt’s thesis is blunt: technologists are endlessly told to “speak the language of the business,” but no one teaches them what that language is. Technology Strategy Patterns is meant to be the Rosetta Stone — a catalog of 39 patterns, borrowed from McKinsey, BCG, Bain, and Harvard Business School, that lets an architect produce a strategy leaders will fund. The recurring maxim, via Lawrence Freedman: “strategy is the art of creating power.”
The architect and the strategist
Hewitt fuses two roles that people want most while knowing least about. He grounds the architect in Vitruvius, the Roman engineer who held that any architecture must satisfy three requirements:
- Firmitas — solid and firm. (“Solid doesn’t mean inflexible” — skyscrapers sway on purpose.)
- Utilitas — useful, fit to its purpose.
- Venustas — beautiful, in the sense of harmonious proportion — “rightsize” your work.
The architect’s three concerns are to contain entropy (standards and conventions), to specify the “-ilities” (the nonfunctional requirements: scalability, availability, security, and the rest), and to determine trade-offs — because “when you invent the ship, you also invent the shipwreck,” and every trade-off ultimately reduces to time and money. Avoid “a shopping list of shiny objects.”
graph TD AR["The architect"] AR --> CE["Contain entropy<br/>standards and conventions"] AR --> IL["Specify the -ilities<br/>scalability, availability, security"] AR --> TO["Determine trade-offs<br/>time and money"] TO -->|"invent the ship,<br/>invent the shipwreck"| RS["Rightsize the work"]
🔑 Key insight
A technology strategy is, in essence, a request to spend millions of dollars of someone else’s money. Everything in the discipline ultimately serves two artifacts — the Strategy Deck and the Ask Deck — because that is how the work gets funded.
The three groups of patterns
graph TD S["Technology Strategy<br/>(39 patterns)"] S --> A["Analysis<br/>critical-thinking metapatterns<br/>(MECE, Logic Tree, Hypothesis)"] S --> C["Creation<br/>building the substance<br/>(World → Industry → Company → Department)"] S --> CM["Communication<br/>winning approval<br/>(rhetoric, templates, decks)"] A --> C C --> CM CM --> ASK["Strategy Deck + Ask Deck<br/>(get funded)"]
The patterns cluster into three logical groups that mirror the workflow:
- Analysis — foundational metapatterns for critical thinking (MECE, Logic Tree, Hypothesis).
- Creation — 19 patterns arranged in concentric scopes from broadest to narrowest: World → Industry → Company → Department.
- Communication — 20 patterns for the rhetoric, templates, and decks that win approval and resources.
You use only the patterns the job needs. A full multi-year org-wide strategy uses all of them; a small database upgrade might use only MECE, a Logic Tree, a Stakeholder Matrix, a RACI, and Principles/Practices/Tools.
The strategist’s role and rhythm
Strategy comes from the Greek strategos, “the general’s art.” Jomini’s division still holds: “Strategy decides where to act; logistics brings the troops to this point; tactics decides the manner of execution.” A working definition: determine the problems and opportunities and shape a course of action that gives the business the greatest advantage, balancing goals, methods, and resources.
💡 Know the calendar
Strategy season typically begins in spring; the deck is presented to executives in late summer, feeding the fall budget season. Knowing this calendar is how you get big items funded — and Hewitt suggests two versions of every Strategy Deck: a detailed, honest one for executives and a shorter public one for teams.
⚠️ Culture eats strategy for breakfast
Drucker’s warning anchors the Triumvirate: Strategy, Culture, and Execution. All three must align. The most elegant strategy dies if the culture won’t carry it or the organization cannot execute it — so a Strategy Deck is the organizational analogue of an architecture definition document, not a stand-alone artifact.
See also
- Analyzing strategy — MECE, Logic Trees, hypotheses, and the world-context frameworks.
- Creating strategy — Porter, Ansoff, BCG, and the concentric creation patterns.
- Communicating strategy — Ars Rhetorica, dramatic structure, and the Ask Deck.
When to use it — and when not
✅ Reach for it when
- When you need to turn a technical vision into a request leaders will fund.
- When you must 'speak the language of the business' but were never taught what that language is.
- When framing a multi-year, org-wide direction that spans world, industry, company, and department scopes.
⛔ Think twice when
- For a tiny project (e.g., a database upgrade) that needs only a handful of patterns, not the full catalog.
- When you have no real ask — a strategy is in essence a request to spend someone else's money.
- When you would present a 'shopping list of shiny objects' rather than a coherent course of action.
Related topics
The analysis metapatterns — MECE, Logic Trees, and Hypothesis — plus the world-context frameworks PESTEL, Scenario Planning, Futures Funnel, and Backcasting that ground a strategy in reality.
path-strategyCreating StrategyThe creation patterns build a strategy's substance in concentric scopes — industry frameworks (SWOT, Porter's Five Forces, Ansoff) and corporate portfolio tools (BCG Growth-Share, APM, Value Chain).
path-strategyCommunicating StrategyWinning approval is its own discipline — the 30-second answer, Ars Rhetorica, dramatic structure, the meeting before the meeting, and the Ask Deck that turns analysis into funded action.
Check your understanding
Score: 0 / 41. What is the essence of any technology strategy, per Hewitt?
Everything in the book ultimately serves the Strategy Deck and the Ask Deck, because a strategy is fundamentally a fundable request — 'it's how you get funded'.
2. What are the three Vitruvian requirements of any architecture Hewitt borrows?
Vitruvius held that architecture must be firm (solid, not inflexible), useful (fit to purpose), and beautiful (harmonious proportion); the architect must also be educated across many fields.
3. What are the three logical groupings of the 39 patterns?
The book mirrors its three parts: Analysis (critical-thinking metapatterns), Creation (building the substance), and Communication (decks and rhetoric to win approval).
4. Which trio must align for a strategy to succeed (Drucker's warning included)?
All three forces — strategy, culture, and execution — must align; a brilliant strategy fails if the culture won't carry it or the org can't execute it.
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