Walk me through annual strategic planning for myself or my small team — not the corporate strategic-planning theater that produces a 60-page deck nobody reads.
WHO THIS IS FOR: {yourself / 2-5_person_team / 10-30_person_company}
WHAT YOU'RE PLANNING: {personal_year / business_strategy / both}
CURRENT STATE in 1 paragraph: {paste — what's working, what's stuck, what just changed}
WHAT FELT BIG LAST YEAR: {2-3_things}
WHAT FAILED LAST YEAR: {2-3_real_misses}
WHAT YOU'RE TIRED OF: {real_frustrations}
WHAT YOU'RE EXCITED ABOUT: {real_pulls}
CONSTRAINTS: {money / family / health / runway / capacity}
WHEN YOU'D EVALUATE this plan: {quarterly / mid-year / monthly}
WHAT YOU DON'T WANT this exercise to produce: {generic_OKR_doc / motivational_vision_statement}
DESIGN a 90-minute exercise (one sitting, alone or with co-founder):
1. **Honest retrospective (15 min)** — 4 questions, written.
2. **The 'kill list' (10 min)** — what to stop doing this year. Most planning fails because nothing gets dropped.
3. **The 3-bet allocation (20 min)** — what are the 3 biggest bets for the year. (Why 3 not 10.)
4. **The 'unsexy work' acknowledgment (10 min)** — what's the maintenance work that has to happen to make the bets possible.
5. **The 'what would have to be true' test (15 min)** — for each bet, what assumptions must hold?
6. **A 1-page artifact (10 min)** — the entire plan on one page. Anything longer doesn't survive.
7. **The quarterly check-in protocol (10 min)** — how you'll re-confront this in 90 days.
No vision statements. No '10x goals'. No 'leverage'. Real, specific, your year.0 copies·0 saves·2 views
251 words·1,597 chars
Sample output
For: myself + 4-person team running a SaaS business. Planning: business strategy. Current state: 2 years in, $400K ARR, slow growth (~10%/qtr), product is decent but not differentiated, team is good but small, runway 14 months. Last year highs: shipped 3 major releases, hired a great designer. Last year fails: changed positioning twice mid-year + didn't ship the data integration we promised customers. Tired of: chasing every customer ask. Excited about: a specific vertical (legal tech) where 3 customers landed unprompted. Constraints: runway, founding team's energy. Evaluate: quarterly. Don't want: a 30-page deck with arrows.
1. Honest retrospective (15 min) — 4 questions:
Write your answers, don't think them. 3 min each.
Q1. What did I/we do last year that I want to NEVER do again? → Changed positioning twice in 6 months. Burned trust with first 8 customers. Burned 2 months of engineering on copy/UX work that we threw away.
Q2. What did I/we get RIGHT last year that I want to keep doing? → Shipped 3 major releases on time. Designer hire was a 9/10. Customer interviews quarterly.
Q3. What's the thing I keep avoiding? → Having a real conversation with my co-founder about whether one of us should focus on legal-tech vertical full-time while the other holds the broader product.
Parameters
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FAQ
The single most powerful question in solo strategic planning: 'what's the thing I'm avoiding that I know I need to do?' Write the answer. Then put it on the plan. That's the move that makes the year different from last year. The prompt targets Claude Sonnet and lives in the Validation & Strategy category on mycopyprompt.
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Q4. What's the most painful customer or stakeholder feedback I got — that I haven't yet acted on? → Three customers explicitly said: 'we use you because of X feature; everything else is a distraction.' I've been ignoring this because it's narrow.
2. The kill list (10 min):
Things we will stop doing this year — write them BEFORE picking bets:
Why kill-list first: every bet requires capacity. You can't take bets without freeing up the time. Most plans skip this and then 'why didn't we hit anything?'
3. The 3-bet allocation (20 min):
Why 3 not 10: you're a 4-person team. 10 bets is 10 mediocre attempts. 3 bets is 3 serious commitments.
Bet 1: Become the AI tooling for legal teams. Reason: 3 unprompted inbound customers in this vertical in last 6 months. No competitor specifically positioned here. The product already does 70% of what they need. Who owns: me (CEO). 60% of my time.
Bet 2: Ship the data integration we promised, by end of Q1. Reason: existing customers cite this as the #1 reason they'd churn. It's been delayed twice. Trust deficit. Who owns: my co-founder (CTO). 80% of CTO's time in Q1.
Bet 3: Build a real distribution channel for legal-tech (content + partnerships). Reason: legal-tech buyers don't respond to cold sales. They consume content from credible voices. We need a credible voice in the space. Who owns: Tessa (designer + content) + me. Q2 onwards.
Everything else is maintenance, not a bet.
4. Unsexy maintenance work (10 min):
Things that must happen for the 3 bets to be possible, that aren't bets themselves:
Why call this out separately: maintenance work is what kills most plans. It gets done in 'extra hours' instead of being budgeted. Then it doesn't get done.
5. 'What would have to be true' test (15 min):
Bet 1 — Become the AI tooling for legal teams. Assumptions:
Bet 2 — Data integration shipping Q1. Assumptions:
Bet 3 — Distribution channel. Assumptions:
If any assumption is wrong, the bet doesn't pivot — it gets re-evaluated at the quarterly check-in.
6. The 1-page artifact:
Print this. Put it on the wall:
2026 PLAN — [Company]
Mission this year:
Become the AI tooling for legal teams.
Bets:
1. Lock down the legal-tech vertical (owner: founder, 60% time)
2. Ship data integration by Q1 end (owner: CTO, 80% time Q1)
3. Build content + partnership distribution in legal-tech (Q2+) (owner: Tessa + founder)
What we're killing:
- Broad SaaS positioning
- Custom requests from non-vertical customers
- 4 features on the public roadmap
- Founder-led demos
- Quarterly rebrands
Maintenance to make these possible:
- Auth refactor + multi-tenancy (Q1)
- SOC2 Type 1 (Q2)
- 24hr support SLA
- Legal-tech-only customer interviews
We re-confront this every 90 days.
This page is the plan.
That's it. No deck, no Notion sub-pages, no 'OKR cascade'.
7. Quarterly check-in (90 min, once per quarter):
Open the 1-page plan. Then:
Bets — status by status (15 min):
Kill list — held? (5 min):
Maintenance — done? (5 min):
Assumptions — what changed? (15 min):
Adjustments (20 min):
Next 90 days (15 min):
What surprised us (15 min):
The quarterly check-in IS the plan. The annual plan is the operating system; the check-ins are when it runs.