Annual Planning Workshop
Run a one-day annual planning session — solo or with your team
The problem
Annual planning at most small businesses either doesn't happen or happens in a rushed afternoon that produces a vague statement like "grow 20%" and nothing else. A real planning process takes a full day and a facilitator, both of which are expensive to hire. This workflow gives you five structured working sessions — each with its own ready-to-use prompt — that take you from last year's actual results to a finished one-page plan by the end of the day.
The tool
Run these five steps in order, in a single day if possible. Each step has its own prompt — copy it into Claude or ChatGPT, fill in the brackets, and carry the output forward into the next step. Block 60-90 minutes per step; if running this with a team, do steps 1-3 solo first, then bring the group in for steps 4-5.
Step 1: Year-in-review extraction
You are helping me conduct an honest year-in-review before I plan next
year. Your job is to pull out the real signal from what actually happened
this year — not what I wish had happened.
WHAT I KNOW HAPPENED THIS YEAR: [PASTE WHATEVER YOU HAVE — REVENUE NUMBERS,
KEY WINS, THINGS THAT FELL APART, CUSTOMER FEEDBACK, TEAM CHANGES]
YOUR TASK:
1. WINS: The 3-5 things that worked, with the reason they worked (not just
that they happened).
2. MISSES: The 3-5 things that didn't go as planned, with the most likely
root cause — not the surface excuse.
3. SURPRISES: Anything that happened that nobody planned for, good or bad.
4. ONE HONEST SENTENCE: If you had to summarize this year in one blunt
sentence for the owner to hear, what would it be?
RULES: Don't soften the misses. Don't credit luck as strategy. If I haven't
given you enough information to assess something, say so instead of
guessing.Step 2: Market shift scan
You are a market analyst helping me understand what's changed around my
business since I last planned, so I don't plan for a market that no longer
exists.
MY BUSINESS AND MARKET: [WHAT YOU DO, WHO YOU SERVE, YOUR REGION/NICHE]
WHAT I'VE NOTICED CHANGING: [COMPETITOR MOVES, CUSTOMER BEHAVIOR SHIFTS,
COST CHANGES, NEW TECHNOLOGY, REGULATION — WHATEVER YOU'VE OBSERVED]
YOUR TASK:
1. Organize what I've told you into: customer shifts, competitive shifts,
cost/supply shifts, and technology/regulatory shifts.
2. For each shift, tell me whether it's a threat, an opportunity, or both —
and why.
3. Flag the ONE shift most likely to hurt me if I ignore it, and the ONE
most likely to help me if I lean into it.
4. Ask me up to 3 questions about shifts I might be missing, based on my
industry, that I haven't mentioned.
RULES: Don't invent market data I haven't given you or that isn't common
knowledge for my stated industry — flag anything you're inferring versus
stating from what I told you.Step 3: 3-scenario visioning
You are helping me stress-test next year by imagining three different
versions of it before I commit to a plan.
MY YEAR-IN-REVIEW SUMMARY: [PASTE OUTPUT FROM STEP 1]
MY MARKET SHIFTS SUMMARY: [PASTE OUTPUT FROM STEP 2]
YOUR TASK — write three short scenarios for next year, 150 words each:
1. FLAT: Nothing major changes, I execute steadily, no big bets pay off or
fail. What does the business look like?
2. BREAKOUT: My best bet this year actually works. What specifically had to
go right for that, and what would I need to have in place to handle it?
3. STRAINED: My biggest risk from the market scan actually happens. What
breaks first, and what's the minimum response that keeps the business
intact?
THEN: name the ONE capability or resource that shows up as necessary across
all three scenarios — that's likely your top investment priority regardless
of which future happens.
RULES: Ground each scenario in what I've told you about my business, not
generic industry speculation.Step 4: Goal-setting
Using everything from the year-in-review, market scan, and three scenarios
above, help me set 1-3 annual objectives for next year that account for
the breakout upside and the strained downside, not just the flat scenario.
YEAR-IN-REVIEW: [PASTE STEP 1 OUTPUT]
MARKET SHIFTS: [PASTE STEP 2 OUTPUT]
THREE SCENARIOS: [PASTE STEP 3 OUTPUT]
Give me 1-3 annual objectives in plain language, each with a one-sentence
reason it's the right bet given all three scenarios. Then tell me: these
annual objectives should become the input to a quarterly OKR-setting
session for Q1 — restate each as a starting point for that conversation.Step 5: One-page plan assembly
Assemble everything from this planning day into a single one-page annual
plan I could put on the wall or share with my team.
INPUTS: [PASTE OUTPUTS FROM STEPS 1-4]
FORMAT — exactly one page:
- One-sentence honest summary of last year
- Top 2 market shifts to watch
- The capability that matters across all three future scenarios
- 1-3 annual objectives
- The single most important thing to get right in Q1
RULES: Ruthlessly cut anything that doesn't fit on one page. If something
important doesn't make the cut, list it separately as "parked for later,"
don't force it in.How to use it
- 1Block a full day (or a half-day solo, spread across a week if that's more realistic for your schedule).
- 2Run steps 1-3 alone first, using real numbers and honest self-assessment — the outputs only help if the inputs are true.
- 3Bring your team in for steps 4-5 if you have one; share the scenario outputs from step 3 before the discussion so everyone starts from the same picture.
- 4Carry each step's output into the next prompt exactly as instructed — don't skip steps or reorder them.
- 5Print or pin the one-page plan from step 5 somewhere visible; revisit it at each quarterly planning session.
- 6Immediately after this workshop, run the annual objectives from Step 4 through the quarterly OKR builder to set your Q1 targets.
Example
Input: a 7-person specialty pet grooming business, year-in-review shows steady revenue but a key groomer left mid-year causing a 6-week booking backlog; market scan flags a new competitor offering mobile grooming.
Sample output excerpt (Step 3, Strained scenario): "Losing another skilled groomer would be the single point of failure — with no cross-trained backup and a 6-week backlog precedent already set, one departure could stall bookings again. Minimum response: cross-train at least one groomer in every specialty service before it's needed, not after."
Step 5 one-page plan (excerpt): "Capability that matters across all scenarios: groomer redundancy — at least one backup trained per specialty. Q1 priority: cross-train two groomers before peak spring season."
Pro tip
Do not skip the "flat" scenario in Step 3 even though it feels boring — it's usually the most likely outcome, and plans that only account for breakout or strained futures tend to overreact in one direction.
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