Facilitate your annual sales planning working session
Runs your annual planning as a facilitated five-phase working session — honest retro, top-down versus bottom-up target reconciliation, 2-4 resourced strategy pillars with stop-doing decisions, ramp-aware hiring math, and a one-page output. It plays the challenging board member most planning sessions lack, so the plan survives its first contact with your leadership team.
You are a strategic planning facilitator who has run annual revenue planning for B2B leadership teams — and you know the two ways these sessions fail: they become budget negotiations wearing a strategy costume, or they produce a 40-slide deck nobody opens after January. You facilitate this session live in this chat, one phase at a time; the output is a one-page plan with numbers and owners. Facilitate my annual planning session in five phases, confirming with me before advancing: 1. Retro: walk me through last year honestly — targets versus actuals, what drove the gap in either direction, which bets paid off, which didn't, and the one thing we kept saying we'd fix but didn't. Push past the first easy answer. 2. The number: pressure-test next year's revenue target top-down (board ambition) versus bottom-up (capacity math). Where they disagree, quantify the gap and make me choose: more capacity, better conversion, or a different number. 3. Strategy pillars: help me pick 2-4 big bets that get disproportionate resources. For each: the thesis, what we stop doing to fund it, the leading indicator, and quarterly milestones. 4. Resourcing: heads, budget, and tools mapped to pillars, with the hiring timeline worked backwards from ramp time — a rep hired in June contributes in Q4. 5. The one-pager: compress everything into a page — number, pillars, milestones, owners, and the three risks we're accepting knowingly. Then list the five questions my leadership team will ask and how the plan answers them. Avoid: pillars that are business-as-usual with a bow on it, plans where nothing gets stopped to fund the new bets, and hockey-stick math where Q4 rescues the year. Before we begin, interview me. Ask me these questions ONE AT A TIME, waiting for my answer each time: 1. What did this year look like — target, actual, and your honest read on why? 2. What's the revenue ambition for next year, and where does that number come from? 3. What are your current capacity facts — team size, ramp times, quota attainment distribution, pipeline sources? 4. What big changes are on the table — new markets, products, channels, leadership? 5. Who has to buy into this plan, and what do they care about most? Once you have my answers, begin phase 1. When I give a vague answer, ask the follow-up a good board member would.
How to use it
- 1
Copy the prompt into Claude, ChatGPT, or any LLM.
- 2
Gather the facts first: this year's actuals, attainment by rep, pipeline by source — the session is only as honest as the retro.
- 3
Block 90 minutes; the phase-gated structure is designed for one deep sitting, though you can pause between phases.
- 4
Let the model challenge you in phase 2 — the top-down versus bottom-up gap is the most valuable argument of the year.
- 5
Bring the one-pager and the pre-answered questions to your leadership review, not a deck.
Best practices
If every pillar sounds like what you already do, you have a budget, not a strategy — ask the model to force a real bet.
The stop-doing list is the test of seriousness; plans that only add never get funded by reality.
Hire dates minus ramp time equals contribution dates — make the model show that math in phase 4.
Revisit the one-pager quarterly and mark each pillar green, yellow, or red; annual plans die from neglect, not error.
Example: what this looks like in practice
A founder-CEO of a 30-person freight-audit software company runs the session in early December. Retro surfaces that this year's 78% attainment traces to a mid-year pricing change, not rep effort. Phase 2 exposes a $2M gap between his $8M ambition and what current capacity supports; he chooses to close it with two Q1 AE hires and a conversion push rather than lowering the number. Pillars land as: enter the 3PL segment, rebuild outbound on trigger data, and fix onboarding-driven churn — funded by killing the underperforming events budget. The one-pager pre-answers his COO's inevitable capacity question with the ramp math. The January board meeting takes 20 minutes on the plan instead of two hours.
Best fit
This prompt is one gear in a bigger machine. We orchestrate 20+ tools into outbound systems our clients own — and guarantee the results.
Apply for a Pilot Spot → →Frequently asked questions
Work in phases: an honest retro of last year, reconciling the top-down target with bottom-up capacity math, choosing 2-4 strategy pillars with explicit stop-doing decisions to fund them, mapping resources with ramp-aware hiring timelines, and compressing it all to one page with owners and accepted risks. This prompt facilitates that exact sequence and challenges vague answers along the way.
More sales strategy & planning prompts
Build a quarterly outbound plan that survives contact with reality
Produces a complete quarterly outbound plan — pipeline math, prioritized segments, 3-5 concrete plays, a launch calendar, and named risks — grounded in your actual win rate and team capacity. The capacity check is the killer feature: it forces the plan to admit when the math doesn't close instead of papering over it with optimism.
Design an irresistible B2B offer with the value equation
Applies the value equation to your actual B2B offer instead of leaving it as a book concept. You get a blunt scoring of your current offer, three rebuilt variants with guarantees your margins can survive, the operational cost of each, and a small validation test — turning 'our offer is fine' into an engineering exercise.
Build a 13-week outbound campaign calendar for the quarter
Turns a pile of campaign ideas into a staggered 13-week execution calendar with owners, prep time scheduled before launches, standing review rhythms, and kill criteria at week 7. It prevents the classic quarter shape — frantic week-1 launches, silent middle, panicked final push — by design rather than discipline.