# Strategy coaching

> Use when they’re debating plans or tactics while what they’re trying to achieve, what’s hard about it, and how they’d overcome that are still muddled.

- Skill: `yanqingcheng/strategy-coaching` (Agent Skill)
- Install (CLI): `npx skillmds@latest add yanqingcheng/strategy-coaching`
- Raw SKILL.md: https://api.skillmd.com/api/skills/yanqingcheng/strategy-coaching/raw
- Safety review: pending
- Works with: Claude Code, Claude.ai, OpenAI Codex
- Category: Coding & Dev Tools
- Author: yanqingcheng (https://skillmd.com/u/yanqingcheng)
- Updated: 2026-09-22
- Page: https://skillmd.com/skills/yanqingcheng/strategy-coaching

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# Strategy coaching

**Structure tool** under [Coaching session](sand-workflow:coaching-session) — Half 1 Understand *or* Half 2 inside a **bounded** problem when strategy structure is the missing piece (goal/challenge/approach muddy). Recognise the hole and drive there with questions; don’t supply the strategy.

Self-contained **coach-side diagnostic** for what to ask next — not a lecture and not a book excerpt. [Stay with](sand-workflow:stay-with) (or drop back to Map) before advancing any layer; don’t skip unfinished shape work. Mid-plan hole → weave Half 1 for that piece, then return.

## Credit

Ideas drawn from Jon Berger's *What Happens When You Are Not In The Room* — https://www.jonbergerleadership.com/home (and related good-strategy thinking). Credit the source; do not reproduce the book.

## Core relationships (know these; ask through them)

1. **Goal** = *what* you're trying to achieve (boolean: done or not). Not the mission. Not the plan.
2. **Challenge** = what is *hard* about achieving that goal. Nested **under** the goal — not a parallel slogan.
3. **Approach** = *how* you will overcome **that** challenge to reach **that** goal. Approach without a clear goal is noise.
4. **Strategy** ≈ **Goal + Approach** (with the challenge made explicit when communicating the approach).
5. **Plan** = actions to enact the approach. Iterate; **commit to goals, not to plans.**
6. **Tactic** = how for a step in the plan — often decided when the leader is absent; needs clear strategy + agency upstream.

Stack (zoom out → actionable):

`Mission/Vision → Goal → Approach → Plan → Tactics`

If they're arguing tactics, climb. If they're stuck in mission poetry, descend to a boolean goal + honest challenge.

## Diagnostic order (question flow)

### 1. Which layer are we on?
- What are you actually trying to decide or align?
- Is this about why we exist, what to achieve next, how to win, what to do this week, or how to do a step?

### 2. Goal before approach
- What's the goal — in a sentence you'd know is true when it's done?
- How would you know it's done (boolean)?
- Is this the goal, or an approach wearing a goal costume?
- If they jump to how: "Approach to *what* goal?"

### 3. Challenge under the goal
- What's hard about achieving **this** goal — specifically?
- If everything were already fine, why are we doing this work?
- What are you tempted to paper over because it's uncomfortable?

### 4. Approach as answer to the challenge
- Given **that** challenge, what's your approach to overcome it?
- What are you choosing *not* to do so this approach can work?
- If the goal changed, has the approach been reconsidered?

### 5. Honesty / fluff tests (as questions)
- If we reverse that statement, is the reverse nonsense? (truism check)
- Could a smart person disagree with this approach?
- If I ask someone else what the strategy is, what would they say?
- Is this a strategy, or a soundbite?

### 6. Toward doing (don’t skip session open)
When structure is clear enough to lean Half 2 — follow [Coaching session](sand-workflow:coaching-session) open (spell map → which piece → outer-edge options), then [Questions — will](sand-workflow:questions-will) / [Questions — transfer](sand-workflow:questions-transfer). Don’t jump straight to will from a tidy goal/challenge/approach.

## Anti-patterns (coach)

- Don't fill in their goal, challenge, or approach.
- Don't lecture frameworks; ask until *they* place challenge under goal.
- Don't confuse plan commitment with goal commitment.

## Stop

They can state goal, name the hard challenge under it, and an approach that answers that challenge — or a clear next decision. Then session Half 2 open / weave as fits — not a one-way “gate.”