Iterative Scouting

• When facing a complex strategic decision with no obvious answer
• When the initial framing of a problem feels too narrow or binary
• After an initial strategic scout has been completed and feedback has been gathered
• When the user's feedback reveals a deeper question than the one originally asked
• When you need to teach or demonstrate the process of strategic thinking
• When the first round of scouting produced useful routes but none feel quite right

When NOT to use:

• When the first scout produced a clear winner that the user is confident about
• When the decision is time-sensitive and a second round would delay action unacceptably
• For simple, well-understood decisions that don't benefit from iteration

III. The Workflow

This is a 4-step iterative workflow. Steps 2-3 may repeat multiple times.

Step 1: Initial Scout

Goal: Explore the initial strategic tension and propose a set of viable routes.

Actions:

1. Identify the initial tension (e.g., "Deprecate vs. Companion")
2. Use the strategic-scout workflow to explore 3-5 diverse routes
3. Present the routes without recommending one
4. Synthesize a provocative starting point -- not to commit to, but to react against

Output: An initial set of routes and a provocative synthesis.

Key insight: The first scout is for provocation, not consensus. Make routes provocative enough to elicit the real conversation.

Step 2: Gather Feedback and Listen for the Reframe

Goal: Present the initial scouting results and listen for the deeper question hidden in the feedback.

Actions:

1. Present the initial routes
2. Listen not just for agreement or disagreement, but for the way the feedback is framed
3. Identify the "question behind the question":
   • Does the user's reaction reveal a different tension than the one you started with?
   • Is the user introducing a new lens or context you hadn't considered?
   • Does the feedback suggest the original framing was too narrow?
4. Articulate the reframe explicitly: "It sounds like the real question isn't [original], but [reframed]."

Output: Either confirmation of the current direction (skip to Step 4) or a clearly articulated reframe.

Key insight: Listen for how feedback is framed, not just what is said. The framing often contains the reframe.

Step 3: Re-Scout with the New Lens

Goal: Conduct a second (or subsequent) round of scouting using the new, more powerful framing.

Actions:

1. Articulate the reframed tension clearly (e.g., "Deep Work vs. On-the-Go")
2. Scout 3-5 new routes that are native to the reframed tension -- not recycled from the first round
3. Present the new routes alongside a brief summary of how the framing shifted
4. Listen again for feedback. If another reframe emerges, repeat Steps 2-3.

Output: A new set of routes native to the reframed tension.

Key insight: New routes should feel genuinely different from the first round. If they feel like minor variations, the reframe wasn't deep enough.

Step 4: Synthesize and Align on the Final Vision

Goal: Synthesize the results of the final scouting round into a coherent direction.

Actions:

1. Select the best route (or hybrid) from the most recent round
2. Define the final direction with clear rationale
3. Document the journey: initial tension, reframe(s), and how the final direction emerged
4. Confirm alignment with the user before moving to execution

Output: A strategic direction document that includes the full scouting journey (initial tension, reframes, final synthesis).

IV. Best Practices

1. The Two-Scout Rule

Why: For any non-trivial strategic decision, the first scout reveals the real question and the second scout answers it.

How: Plan for at least two rounds of scouting. Set expectations with the user that the first round is exploratory.

2. The Reframe is the Prize

Why: The most valuable output of the process is not a chosen route but a new, more powerful question.

How: After each round of feedback, explicitly name the reframe. Write it down. Compare it to the original tension.

3. Scout for Provocation, Not for Consensus

Why: Safe, consensus-friendly routes don't generate the friction needed for reframes.

How: Include at least one provocative route per round -- something that challenges assumptions or inverts the question.

4. Don't Recycle Routes

Why: The reframe should produce genuinely new options, not minor variations of previous routes.

How: After a reframe, generate routes from scratch using the new lens. If old routes still apply, they'll re-emerge naturally.

5. Know When to Stop

Why: Infinite scouting is analysis paralysis. The loop should converge, not diverge.

How: If the second round produces alignment, stop. If a third round is needed, that's fine, but ask: "Are we refining or avoiding a decision?"

V. Quality Checklist

Before concluding, verify:

• Have you completed at least two rounds of scouting?
• Can you clearly articulate the initial tension and the reframed tension?
• Did the reframe lead to a richer, more insightful set of strategic options?
• Are the second-round routes genuinely different from the first-round routes?
• Is the final vision aligned with the insights from the final scouting round?
• Is the full journey (initial tension -> reframe -> synthesis) documented?
• Has the user confirmed alignment with the final direction?

VI. Common Pitfalls

Pitfall 1: Treating the First Scout as Final

Problem: Committing to a route from the first round without testing whether a deeper question exists.

Solution: Always gather feedback after the first round. Ask: "Does this feel like the right question, or is there something deeper?"

Pitfall 2: Recycling Routes Across Rounds

Problem: The second scout produces the same routes with minor tweaks, missing the point of the reframe.

Solution: Generate routes from scratch using the new lens. Old routes that still apply will re-emerge naturally.

Pitfall 3: Infinite Scouting

Problem: Using the iterative loop to avoid making a decision. Each round produces a new reframe, and the process never converges.

Solution: Set a maximum of 3 rounds. If alignment hasn't emerged by the third round, the tension may need to be split into smaller, more tractable questions.

Pitfall 4: Losing the Thread

Problem: After multiple rounds, forgetting the original tension and how the conversation evolved.

Solution: Document each round's tension, routes, feedback, and reframe. The journey is as valuable as the destination.

VII. Example: Web App to Multi-Surface Strategy

Initial Tension: "Should we deprecate the web app or ship it as a companion to desktop?"

Round 1 Scout: 5 routes explored (Full Deprecation, Simplified Companion, Web as Beta, PWA Bridge, Freemium Split). Recommended hybrid: Simplified Web Companion as Pre-Alpha.

Feedback and Reframe: User's response shifted the conversation: "What if the web app is for mobile-first, on-the-go orchestration?" This revealed the real question wasn't about the web app's fate -- it was about what mobile users need.

Reframed Tension: "Desktop for Deep Work vs. Mobile for On-the-Go Orchestration."

Round 2 Scout: New routes native to the reframe (Mobile-First PWA, Native Companion App, Hybrid PWA-then-Native, Desktop-Only with Mobile Notifications). Selected: Hybrid PWA Now, Native Later.

Final Synthesis:

• Desktop: Core product for deep work ($20/month)
• Mobile PWA: Premium tier for on-the-go orchestration (separate subscription, 4-6 weeks after desktop)
• Web: Free tier for discovery and onboarding

The Journey: Started with "deprecate or companion?" and ended with a three-tier multi-surface strategy. The reframe from "web app fate" to "mobile context" was the transformative insight.

VIII. Related Skills

• strategic-scout -- The single-pass scouting workflow used within each round
• product-positioning -- Use when the reframe reveals a binary positioning question
• multi-surface-strategy -- Use when the reframe reveals a multi-surface opportunity