Strategy from the Obstacle: a sheet for the owner

Goal. This sheet turns your goal for the year into a strategy: a named obstacle, a chosen path and three actions that support each other. It makes you pick one of two paths and test the weakest assumption before you spend money. At the end you have a near-term goal to start your 90-day plan.

In 15 minutes. In 15 minutes you won’t choose a strategy. You will choose the obstacle, the path to test first and one test that settles it. The time is our estimate, not measured, and you take the facts from memory, so check them against your invoices and calendar afterwards.

1. Goal and “what would have to happen” (part 1), 2 minutes. Write your goal for this year and answer what would have to happen to reach it. If the answer is “more work,” you don’t have a strategy yet. Keep writing.
2. Facts (part 1), 3 minutes. Write three facts, each with a source (invoices, calendar, CRM, a conversation), instead of five. Finish: “What holds us back most is ___.”
3. The obstacle (part 2), 3 minutes. Write three sentences at most: what stands in the way, with no number and no goal, and what of it is within your reach.
4. Two paths (part 3), 4 minutes. Describe two paths, one sentence each. For each, finish: “For this path to work, it has to be true that ___.” Mark the condition you believe in least.
5. The test (part 3), 2 minutes. For that condition, write a test, a pass mark and a date. The most skeptical person you know sets the pass mark, not you.
6. Decision, 1 minute. Write one line: “I decide that … Who … By when … I will check …”. For example: “I decide that the obstacle is quoting time and I test path 1 first. Who: my business partner sets the pass mark, I hold the conversations. By when: in 3 weeks. I will check: whether at least 4 of 8 people want to work with us on a regular basis.”

The result of the test decides which path you work out in parts 4 to 6 of the full version.

Instructions (full version) (about 90 minutes for the first version, an estimate; plus time for one test, usually from a few days to three weeks)

1. Fill in parts 1 and 2 on your own, before you ask anyone, AI included.
2. Describe two paths and ask the most skeptical person you know (a business partner, a manager, your accountant) for a test and a pass mark for the weakest condition of each path.
3. Test the condition you believe in least first. If it doesn’t pass, cross out that path.
4. Until you have the result, treat parts 4 and 5 as a draft. After the test, revise them for the path that passed.
5. Carry the near-term goal over to the 90-day plan and put the review date in your calendar.

Template fields

Part 1. Starting point

• Our goal for this year: ___
• What would have to happen to reach it? ___ (If the answer is “more work,” you don’t have a strategy yet. Keep writing.)
• Five facts, each with a source (invoices, calendar, CRM, a conversation): 1. ___ 2. ___ 3. ___ 4. ___ 5. ___
• My first sentence: “What holds us back most is ___.”

Part 2. Diagnosis (three sentences at most, no number and no goal)

• The obstacle, that is, what stands in the way, not what we want to achieve: ___
• What gets easier once we overcome it: ___
• What of this is within our reach: ___
• Two other answers and why I reject them: ___

Part 3. Two paths you can’t take at once

Why you can’t take both at once: ___

Part 4. Direction and boundaries

• “We will be ___, using ___, so we will not ___.”
• Where we don’t play: 1. ___ (who will be disappointed: ___) 2. ___ (who: ___)

Part 5. Three actions

Fit (supports, neutral, hinders): 1 and 2: ___ · 1 and 3: ___ · 2 and 3: ___. For every “hinders,” write a fix or swap the action.

Part 6. Near-term goal and safeguard

• One near-term goal you can reach with today’s people and hours (the start of the 90-day plan): ___
• It is [date 6 months from now] and it didn’t work. Three causes and what we do about them: 1. ___ 2. ___ 3. ___
• We come back to this document if: ___ · Review date: ___

Quick check: ☐ The diagnosis has no number and no goal. ☐ Neither path is there just for the sake of form. ☐ The direction rules something out. ☐ The actions support each other. ☐ An outsider can say what you are doing on Monday.

Fictional example (the firm and the numbers are fictional, for this template)

A woodworking shop, custom-made furniture, 11 people.

• Goal: 20% more revenue and a margin above 15%. What would have to happen? “Sell more.” So there is no strategy yet.
• Facts: 55% of revenue is kitchens (invoices). A kitchen quote waits for the owner 12 days on average (calendar). Of 40 quotes in the quarter, 11 turned into orders (quotes spreadsheet). Store fit-outs have the lowest margin (the accountant). Two interior designers sent 6 of the 11 orders (notes).
• First sentence: “What holds us back most is a shortage of people in production.”
• Diagnosis: We lose orders at the quote, not in production. We make every kind of furniture, so every quote is a new design and waits for the owner. Once we shorten the road to a quote, the same hands will fill more of the orders that already come in. Rejected: a shortage of people (production has idle days every other week); prices too high (three customers who left pointed to time).
• Path 1: kitchens for interior designers’ clients; more value: ready-made modules and a quote in 3 business days. Weakest condition: four interior designers want to work with us on a regular basis. Test: conversations with eight of them in 3 weeks, pass mark (set by the skeptical business partner): 4 commitments and 2 projects to quote. Result: 5 and 3, passed.
• Path 2: wardrobes for online customers. Lower cost is out, since the furniture chains are cheaper; that leaves fast installation. Weakest condition: ads bring in 20 inquiries a month for 1 500 PLN at most. Test: a month of ads. Result: 9, failed.
• Why not both: both need the owner’s hours, and each needs a different offer and a different message.
• Direction: “We will be a kitchen workshop for interior designers, using ready-made modules and fast quotes, so we will not take on stairs or store fit-outs.” Where we don’t play: store fit-outs (disappointed: a regular customer with three stores), single wardrobes from classified ads.
• Actions: 1. A catalog of 30 kitchen modules with prices (rules out designs from scratch). 2. A rule: the production manager quotes from the catalog, the owner only above 60 000 PLN. 3. The owner spends one day a week with interior designers. Fit: every pair supports each other (rule 2 frees up the day for action 3).
• Near-term goal: by the end of the quarter, every kitchen quote from the catalog goes out within 3 business days.
• Pre-mortem: designs outside the catalog (quote in 10 days, with a surcharge); the owner goes back to quoting (on Fridays we check who did the quotes); too much revenue lost from the stores. We come back if revenue falls by more than 10% after two months. Review: in 3 months.

From us. The layout “obstacle, direction, actions that support each other” comes from Richard Rumelt (Good Strategy Bad Strategy, ch. 3, 5 and 7: a goal is not yet a strategy, the diagnosis names the obstacle, a near-term goal is within reach). The question “what would have to be true” and the rule to test first what you believe in least are from Playing to Win (A.G. Lafley and Roger Martin, ch. 8), and the “pre-mortem,” imagining the plan has failed and writing down why, is Gary Klein’s idea (Sources of Power, ch. 5). What we added is the rule that the diagnosis has three sentences at most and contains no number and no goal, and the fit test for the three actions.

When to call us. Call us if:

• both paths pass the test, or neither does, and you can’t choose;
• you have nobody in the company who will set the pass mark and say “no” before you spend money on the chosen path;
• choosing the path costs more than a month of the company’s revenue.

The first call with us is 30 minutes and free. Bring your sheet.

Prompt for your AI. This prompt works in your own ChatGPT, Claude or Gemini account and knows only what you tell it; our own method, built on what your company knows, is what we do in a Diagnosis.

You are a calm coach. Take me through the “Strategy from the Obstacle” card, the 15-minute version.
Rules:
1. Ask one question at a time and wait for my answer.
2. If an answer is vague, ask for a number or example.
3. Never invent anything about my company. Write what I don't know as “to check”.
4. Don't choose the obstacle or the path for me.
At the start, tell me: “Do not paste passwords, account numbers or personal data.”
Questions: (1) my goal for this year, and what would have to happen; (2) three facts with sources; (3) the obstacle in three sentences, no number, no goal; (4) two paths, each with a condition that has to be true; (5) a test, a pass mark and a date for the condition I believe in least.
At the end, write one line: “I decide that … Who … By when … I will check …”.