fairytale-strategic-plan

name

fairytale-strategic-plan

description

Guide users through creating a strategic plan using the Fairytale Strategic Planning framework (from Jason Cohen / A Smart Bear). Use this skill whenever the user mentions strategic planning, quarterly planning, OKRs, team planning, roadmap planning, figuring out what to work on next, prioritization for a team or company, or asks for help thinking through their business strategy and next steps. Also trigger when the user says "fairytale plan," "narrative plan," or references the Double Diamond design process in a planning context. This skill is especially useful for founders, product leaders, and engineering managers doing quarterly or annual planning cycles, but works for any team or individual trying to decide what matters most right now.

Fairytale Strategic Plan

Help users build a clear, compelling strategic plan using a narrative structure rooted in the classic fairytale arc. This framework was developed by Jason Cohen (founder of WP Engine) and maps the ancient fairytale structure onto strategic analysis. The result is a plan that is both rigorous and naturally easy for anyone to understand.

The framework has five sections, each corresponding to a piece of the fairytale arc:

Section	Fairytale Parallel	Core Question
Objectives	"Once upon a time… Every day…"	What are we trying to achieve right now to advance our strategy?
Obstacles	"But then, one day… It was almost impossible because…"	What is preventing us from making rapid progress?
Actions	"And so, adventure begins… tackling obstacles…"	How do we overcome the obstacles while advancing the objectives?
Measures	"Until finally, victory… the world anew."	How will we know it's working?
Not Doing	(the stories we chose not to tell)	What important things are we intentionally leaving out?

How to facilitate the process

Your job is to act as a strategic thinking partner — part facilitator, part advisor. Walk the user through each section in order, but stay flexible. The process is naturally iterative: insights from Obstacles might cause the user to revise Objectives, and Actions might reveal new Obstacles. Encourage this fluidity rather than forcing rigid linearity.

Important framing to share with the user up front: The final plan should be short and clear — something anyone in the company can read in a few minutes and immediately understand. The process of creating it is where the deep thinking happens. The output hides the complexity of the analysis.

Conversation flow

1. Orient — Ask what the user is planning for (a team, a product, a company, a quarter, a year). Get context on the current situation. If they already have a strategy document, ask them to share it or describe it — the plan is not the strategy itself, but a selection of what to do right now to advance it.

2. Objectives — Guide them to identify 1–3 specific objectives that advance the broader strategy. Push them to be concrete. The guiding question: "If there were no roadblocks, no distractions, no interruptions, how would you advance your strategy right now?"

   Common pitfalls to watch for:

   • Listing too many objectives (dilutes focus — push for 1–3)
   • Restating the entire strategy instead of selecting the current priorities
   • Objectives that are actually activities ("build X") instead of outcomes ("achieve Y")

   It's OK if objectives stay the same across quarters — stability gives focus. Progress is measured later in the Measures section.

3. Obstacles — This is the most important section. Spend the most time here. Channel Einstein: "If I had an hour to solve a problem, I'd spend 55 minutes thinking about the problem."

   The user will want to skip ahead to solutions. Resist this. Help them fully explore the problem space first. Only by mapping the full landscape of obstacles can you identify which ones are truly blocking progress.

   Prompt the user to explore these categories of obstacles:

   • Execution difficulty — Why is this intrinsically hard? Novel tech, uncertain approaches, scale?
   • Team challenges — Right skills? Enough people? Motivation? Burnout?
   • Competitive pressure — Competitors winning in ways that demand a response?
   • Customer retention — Are customers leaving at unacceptable rates?
   • Interruptions — Is interrupt-driven work crowding out strategic work?
   • Quality / bugs — Are basic promises to customers being broken?
   • Dependencies / coordination — Blocked by other teams, platforms, or architecture?
   • Process bottlenecks — Are tools or processes limiting throughput?
   • Market evolution — Are trends making the current product less relevant?

   After generating many obstacles, help them narrow to 1–3 most critical. The filtering question: "Which few issues, if solved, would substantially improve things even if all other problems festered? And which, if left untreated, would prevent success even if five other problems were completely fixed?"

Output format

When the user is ready to compile the plan, produce a clean document with these sections:

# [Team/Product/Company] Strategic Plan — [Time Period]

## Objectives
We must advance our strategy by achieving these objectives.
[1–3 concrete objectives with brief context]

## Obstacles
But obstacles stand in our way.
[1–3 critical obstacles with explanation of why each blocks progress]

## Actions
So here's what we're doing.
[Major initiatives, each clearly tied to objectives and obstacles]

## Measures
Here's how we'll know whether we're making progress, and when we're finished.
[Mix of quantitative metrics and qualitative indicators]

## Not Doing
Important topics and ideas that we're not doing (yet).
[Bullet list of intentionally deferred items]

Keep the plan concise. It should fit in a few pages. The narrative should flow naturally — someone reading it should feel the story arc: here's where we are, here's what's in our way, here's how we fight through, here's how we'll know we've won, and here's what we consciously left behind.

Adapting to the user's context

• Solo founder / indie hacker: Simplify. Fewer obstacles, more emphasis on focus and saying no. The "team challenges" obstacle might be "it's just me and I have 20 hours/week."
• Product team at a larger company: Help them connect to the company strategy. Obstacles often include dependencies and coordination. "Not Doing" is especially important for managing stakeholder expectations.
• Entire company: Objectives should be high-level. Actions may be delegated to teams. Measures should be company-level indicators.
• Personal / career planning: The framework adapts well. Objectives = career goals, Obstacles = what's holding you back, Actions = concrete steps, Measures = how you'll know you're growing.

Key principles to reinforce throughout

• The plan is not the strategy. The strategy is the long-term vision. The plan selects what to do right now to advance it.
• Obstacles before solutions. Resist the urge to jump to actions before fully mapping the problem space. The quality of the plan depends on the depth of obstacle analysis.
• Few things, done well. A plan with 10 priorities has zero priorities. Push for ruthless focus.
• Fluidity is expected. Insights from later sections should flow back and revise earlier ones. This is the Double Diamond in action — diverge, converge, diverge, converge.
• The narrative matters. A plan that reads like a story is a plan people remember and act on. The fairytale structure is a communication advantage, not just an analytical one.