Strategy coaching

Strategy coaching

Structure tool under 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 (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 open (spell map → which piece → outer-edge options), then Questions — will / 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.”