---
id: wiki-2026-0508-strategic-thinking
title: Strategic Thinking
category: 10_Wiki/Topics
status: verified
canonical_id: self
aliases: [Strategic Thinking, Strategy, Engineering Strategy]
duplicate_of: none
source_trust_level: B
confidence_score: 0.85
verification_status: applied
tags: [strategy, decision-making, engineering-leadership]
raw_sources: []
last_reinforced: 2026-05-10
github_commit: pending
tech_stack:
  language: na
  framework: na
---

# Strategic Thinking

## 매 한 줄
> **"매 long-horizon, multi-step, 매 trade-off 의 reasoning — 매 goal → diagnosis → guiding policy → coherent actions"**. Richard Rumelt, *Good Strategy / Bad Strategy* (2011) 의 kernel. 매 engineering context — 매 architecture choice, tech debt, hiring, platform investment.

## 매 핵심

### 매 Rumelt kernel
1. **Diagnosis**: 매 challenge 의 명확한 정의 — what is actually hard?
2. **Guiding Policy**: 매 approach — how we'll address it.
3. **Coherent Actions**: 매 mutually reinforcing concrete steps.

### 매 strategic vs tactical
- **Strategic**: months-years, irreversible, enables/blocks options.
- **Tactical**: days-weeks, reversible, executes within strategy.
- **Type 1 vs Type 2 decisions** (Bezos): 매 one-way door (strategic) vs two-way door (tactical).

### 매 frameworks
- **OKRs**: Objective + Key Results.
- **Wardley Map**: 매 capability evolution chain (genesis → custom → product → commodity).
- **Five Forces** (Porter): 매 industry structure.
- **First Principles** (Musk): 매 axiom 부터 reason.
- **Pre-mortem** (Klein): 매 future failure 의 imagine.

### 매 응용
1. Engineering org strategy (build vs buy, monolith vs micro).
2. Career planning (5-year arc).
3. Technical roadmap prioritization.

## 💻 패턴

### Pre-mortem template (Markdown ADR)
```markdown
# ADR-042: Migrate to Kubernetes

## Diagnosis
Current ECS deployment cannot scale to multi-region; deploys take 40min.

## Pre-mortem (it's 2027, this failed)
- Team didn't learn k8s; constant outages.
- Cost 3× higher than ECS.
- Migration took 18 months instead of 6.

## Mitigations
- Hire 1 SRE with k8s background before start.
- Pilot with 2 non-critical services for 3 months.
- Define rollback criteria.
```

### Wardley Map (text DSL — onlinewardleymaps.com)
```
title Engineering Platform 2026

component User [0.95, 0.50] label [0, -10]
component Web App [0.85, 0.55]
component Auth [0.75, 0.70]
component LLM Inference [0.55, 0.30] label [0, 10]
component GPU Cluster [0.30, 0.40]
component Datacenter [0.10, 0.30]

User -> Web App
Web App -> Auth
Web App -> LLM Inference
LLM Inference -> GPU Cluster
GPU Cluster -> Datacenter
```

### First-principles decision (LLM-augmented)
```python
# Use Claude Opus 4.7 for option exploration
from anthropic import Anthropic
client = Anthropic()
def explore_options(problem: str, constraints: list[str]) -> str:
    msg = client.messages.create(
        model="claude-opus-4-7",
        max_tokens=2000,
        thinking={"type": "enabled", "budget_tokens": 8000},
        messages=[{"role": "user", "content":
            f"Problem: {problem}\nConstraints: {constraints}\n"
            "From first principles, list 5 distinct approaches with key trade-offs."}],
    )
    return msg.content[-1].text
```

### Decision matrix (weighted)
```python
options = {
    "Postgres":  {"perf": 7, "cost": 9, "team_skill": 9, "scale": 6},
    "DynamoDB":  {"perf": 9, "cost": 5, "team_skill": 4, "scale": 9},
    "CockroachDB":{"perf": 8, "cost": 6, "team_skill": 5, "scale": 8},
}
weights = {"perf": 0.3, "cost": 0.2, "team_skill": 0.3, "scale": 0.2}
scores = {k: sum(v[c]*weights[c] for c in weights) for k, v in options.items()}
print(sorted(scores.items(), key=lambda x: -x[1]))
```

### OKR structure
```yaml
objective: Make platform self-serve for new teams
key_results:
  - 90% of new services deploy without platform team involvement (currently 20%)
  - Onboarding time < 1 day (currently 3 weeks)
  - NPS from internal devs > 50
```

### Type-1 vs Type-2 framing
```markdown
| Decision | Type | Reversibility | Rigor needed |
|---|---|---|---|
| Choose primary DB | 1 | Low | High — involve all leads |
| Choose CI provider | 2 | Medium | Medium |
| Choose linter ruleset | 2 | High | Low — just decide |
```

### Strategy doc skeleton (Will Larson style)
```markdown
# Strategy: Platform Reliability 2026

## Context
Outages weekly, MTTR 4hrs, eng team rotates on-call.

## Diagnosis
Lack of observability + flaky integration tests + no SLO discipline.

## Guiding Policy
Invest in observability and SLO culture before adding features.

## Actions
1. Adopt OpenTelemetry across all services (Q1).
2. Define SLOs for top 10 services (Q1).
3. Error-budget-based release gating (Q2).
4. Hire 2 SREs (Q2).

## Non-goals
- Multi-region active-active (defer to 2027).
- New feature work pause: NO — 70/30 split.
```

## 매 결정 기준
| 상황 | Approach |
|---|---|
| Long-horizon org/tech direction | Rumelt kernel + Wardley map |
| Capability evolution planning | Wardley map |
| Multi-option comparison | Weighted decision matrix + ADR |
| Risk-laden irreversible decision | Pre-mortem + Type-1 framing |
| Quarterly execution | OKRs |
| Novel/uncertain space | First principles + LLM exploration |

**기본값**: 매 strategic decision → ADR + diagnosis + pre-mortem.

## 🔗 Graph
- 부모: [[Decision Making]]
- 응용: [[Architecture Decision Record]]
- Adjacent: [[Systems_Thinking|Systems Thinking]] · [[Mental_Models|Mental Models]]

## 🤖 LLM 활용
**언제**: option exploration, pre-mortem brainstorming, devil's advocate, summarize long context for diagnosis.
**언제 X**: 매 final commit decision — accountability 의 human; 매 confidential strategy — privacy concern.

## ❌ 안티패턴
- **Goals as strategy**: "be #1" 의 strategy X — 매 goal. 매 diagnosis + policy 의 missing.
- **Strategy as wishlist**: 매 incoherent action list, 매 trade-offs 의 unstated.
- **Pre-mortem 의 skip**: 매 surprise failure mode.
- **Analysis paralysis on Type-2 decisions**: 매 reversible 의 just decide.
- **Wardley map as drawing exercise**: 매 decision 으로 connect X — 매 useless.

## 🧪 검증 / 중복
- Verified (Rumelt *Good Strategy/Bad Strategy* 2011; Larson *An Elegant Puzzle*; Wardley *Wardley Maps* 2018).
- 신뢰도 B (synthesis from multiple authorities).

## 🕓 Changelog
| 날짜 | 변경 |
|---|---|
| 2026-05-08 | Phase 1 |
| 2026-05-10 | Manual cleanup — strategic thinking frameworks for engineering |