50 free operator prompts across 5 categories of 10 prompts each. Calibrated for the CFO, COO, Chief of Staff, and Head of Operations who run the company while the founder runs the strategy. Each prompt produces a decision memo, a variance analysis, a process change, or a hard conversation prep. Banned phrases include "founder mode", "operator mindset", "10x the business", "running point", "world-class", "best-in-class", "executing flawlessly", "scaling rapidly", "reps on the bar", "lean in", "hustle", "rolling up sleeves".
Pairs with the 8-Component Skeleton framework for the strategic and process categories and the Founder Pack for the financial and people categories. Free, no email gate.
For the operator, not the influencer
The operator-content genre on LinkedIn and Twitter has produced a thousand threads about "operator mindset" without a single named decision. Real operators write boring memos with hard numbers and named tradeoffs. The threads describe a vibe; the memos make a call. This pack is calibrated for the people who write the memos.
Six dimensions of difference between the operator voice and the influencer voice. Substance: the operator names the specific decision; the influencer names the disposition (decisive, ruthless, customer-obsessed). Tradeoffs: the operator names what is being lost; the influencer says "and" instead of "or". Numbers: the operator opens with the number; the influencer opens with the story. Ownership: the operator names the owner and date; the influencer names the team. Tone: the operator writes flat memos; the influencer writes narrative arcs. Audience: the operator writes for the CEO, board, or specific function; the influencer writes for the algorithm.
Both voices exist in the wild. Only one runs companies. The pack is calibrated for the first; it explicitly rejects the second at the prompt level by banning the genre's signature phrases inline. The result is output that reads like a memo from a CFO who has run a close, not a thread from a personal-brand operator who has not.
Five categories. The operator workflow end to end.
The five categories map to the five operating disciplines that determine whether a company runs smoothly or accumulates dysfunction. Financial Operations and FP&A comes first because the close, the cash forecast, and the unit economics determine what is real. People and Org Operations comes second because the company is the people. Strategic Operations comes third because the strategic plan needs to translate into operating decisions or it is just a deck. Process and Systems Operations comes fourth because the process work is what scales the company beyond the founder's attention. Communication and Decision Operations comes fifth because the company runs on the quality of the decision memos and the all-hands messages.
Most operators who fail to compound do so by skipping the unglamorous categories: process, comms, and the boring half of finance. The thread-genre operator skips these in favor of "strategic" work; the actual operator does these because they are the leverage.
Category 01: Financial Operations and FP&A
Ten prompts for the financial operations and FP&A work that determines whether the company has a real read on its numbers or is running on vibes. The shape: monthly close that closes, variance analysis that drives action, cash flow forecasting under uncertainty, vendor and headcount cost decisions named in dollars not adjectives. Reject the entire 'finance partner' theater that produces decks no one reads.
Pairs with: Founder Pack
1. Monthly close acceleration plan
Current monthly close timeline: [paste days from period end to close]. Finance team headcount: [paste]. Tools: [paste accounting system, close management]. Bottlenecks: [paste, e.g. accruals, intercompany, revenue recognition, FX]. Draft a 400-word close acceleration memo: the three bottlenecks consuming the most time, the specific actions for each (process change, automation, policy change, deferred to quarter), the realistic close-day target for next quarter and the year, the headcount or tool implication. Numbers and named tradeoffs, not 'world-class close' aspirations.
2. Variance analysis that drives action
Period: [paste]. Plan: [paste line items and amounts]. Actual: [paste]. Variance: [paste with dollars and percent]. Draft a 300-word variance memo: the three variances over the materiality threshold (define it), the cause for each (timing, volume, price, mix, one-time, ongoing), the action for each variance that is structural not timing, the question the variance raises about the plan itself. Variance analysis without action is bookkeeping; this prompt forces the action column.
3. Cash flow forecast under uncertainty
Cash position: [paste]. Monthly burn: [paste range, low and high]. Committed inflows: [paste with timing]. Committed outflows: [paste with timing]. Uncertain inflows: [paste]. Draft a 500-word 13-week cash forecast memo: the base case, downside case (collections delayed, revenue miss), the breakeven trigger date for each scenario, the financing or expense decisions implied by each scenario, the assumption that most affects the answer. Cash forecasts that show only the base case are aspirational; this version names the downside trigger date.
4. Burn rate reduction memo without panic
Current monthly net burn: [paste]. Runway at current burn: [paste months]. Runway target: [paste, e.g. 18 months]. Revenue trajectory: [paste]. Draft a 600-word burn reduction memo: the gap between current and target burn, the specific cuts ranked by dollar impact and reversibility (people decisions are last and largest), the cuts that hit the income statement vs balance sheet, the specific people-decision threshold (do not touch headcount until non-headcount cuts exhaust), the decision deadline. Operator memo register; no 'lean and mean' framing.
5. Unit economics teardown
Product or business unit: [paste]. Revenue per customer (or unit): [paste]. Gross margin: [paste]. CAC: [paste]. Payback period: [paste]. LTV (defined): [paste]. Draft a 400-word unit economics teardown: the honest read on whether the unit economics work, the specific assumption that most affects the answer (typically: churn assumption or CAC blended vs paid), the decision implied (continue, fix specific input, kill, pivot), the metric to track for the next quarter to validate. Honest tone; unit economics that look great usually have one input that does not survive scrutiny.
6. Pricing decision memo
Current pricing: [paste]. Customer segments: [paste with willingness to pay if known]. Competitive pricing: [paste]. Cost per delivery: [paste]. Draft a 500-word pricing decision memo: the three pricing options (hold, raise X percent, restructure), the customer impact of each (churn risk, expansion impact), the revenue impact at the margin, the recommendation with named tradeoffs, the rollout sequence. Pricing decisions that get framed as 'value-based' without a willingness-to-pay number are not decisions.
7. Vendor renegotiation pack
Vendor: [paste]. Current spend: [paste annual]. Contract end: [paste]. Use case: [paste]. Alternatives: [paste with rough cost]. Draft a 400-word renegotiation pack: the specific ask (target percent or dollar reduction), the leverage I have (volume change, alternatives, multi-year commit, payment terms), the BATNA (specific alternative if no deal), the conversation script with three concession scenarios, the walk-away threshold. Vendor negotiations that start without a walk-away threshold end at the vendor's preferred number.
8. AR collection workflow
Current AR aging: [paste 30 / 60 / 90+ buckets in dollars]. DSO: [paste]. Top five outstanding accounts: [paste with amount and age]. Draft a 400-word AR collection workflow memo: the cause analysis for the largest aged balances (process, customer dispute, customer cash, ours), the action for each cause (collections call, dispute resolution, payment plan, write off), the system change to prevent the next aging buildup, the DSO target and timeline. AR work that focuses on the chase ignores the upstream causes.
9. Headcount cost model
Current headcount: [paste by function]. Average loaded cost per head by function: [paste]. Open roles approved: [paste]. Open roles requested but not approved: [paste]. Draft a 400-word headcount cost memo: the total cost trajectory for next four quarters under three scenarios (freeze, planned hires, requested hires), the function-by-function cost vs revenue contribution, the role priorities under a freeze (which two roles get filled first if only two are allowed), the trigger that would move us between scenarios. Numbers, not 'invest in talent.'
10. CFO one-on-one prep with CEO
Standing items: [paste, e.g. monthly close, cash, hiring, board prep]. New items: [paste]. Asks: [paste, e.g. decision needed on X]. Draft a 300-word CFO one-on-one agenda: the three items requiring decision (each with options and recommendation), the two items requiring information (status update only), the one item that is uncomfortable but needs to be on the agenda, the specific time allocation for each. CEO time is the scarce resource; one-on-ones that drift across status updates without decisions waste it.
Category 02: People and Org Operations
Ten prompts for the people and org work that produces functioning teams or accumulates dysfunction. The shape: performance reviews that name the actual issue, comp decisions tied to the band, layoffs handled with operator discipline, hiring slowdowns communicated honestly. Reject the 'people-first' / 'lean in' / 'culture deck' framing that performs care without doing the hard work.
Pairs with: 8-Component Skeleton framework
11. Performance review that does not lie
Person and role: [paste]. Tenure: [paste]. Performance reality (private): [paste honest assessment]. Goals last cycle: [paste]. Draft a 500-word performance review that names the actual issue: the specific behaviors meeting / not meeting the bar (with examples not adjectives), the bar itself defined, the trajectory (improving, flat, declining), the specific commitments for the next cycle, the implicit decision (continue, formal plan, exit). Reviews that praise generally and criticize vaguely produce no behavior change; this prompt forces specificity.
12. Hard conversation prep
Person: [paste]. Issue: [paste, e.g. performance, conflict, attitude, role mismatch]. Context: [paste, what has been tried, who else is affected]. Draft a 400-word conversation prep: the opening that names the issue without rehearsing it, the three to four specific examples ready, the boundary (what is not changing), the path forward I will offer, the response if the person disagrees, the response if the person asks 'am I being fired'. Hard conversations that get rehearsed as scripts often fail; this prompt prepares the structure not the words.
13. Layoff decision memo
Current headcount: [paste]. Burn vs runway gap: [paste]. Revenue trajectory: [paste]. Draft a 700-word layoff decision memo for the CEO and board: the rationale (financial, not 'restructuring for growth'), the size (specific count and percent, named in advance not derived from named individuals), the criteria (function priority, performance, role redundancy, named in that order), the severance and notice policy (specific weeks), the communication sequence (CEO all-hands first, then department heads, then individuals, in that order), the rebuild plan if the cuts work. Layoffs handled with discipline are awful but recoverable; layoffs handled poorly damage the company for years.
14. Hiring slowdown communication
Decision: [paste, e.g. pause hiring outside critical roles, slow to 1 hire per quarter, freeze]. Trigger: [paste financial or strategic]. Open roles affected: [paste count]. Draft a 400-word hiring slowdown communication for the team: the decision named directly (no 'shifting our talent strategy'), the rationale (the number that triggered the decision), the impact on existing teams (more work, slower scaling, named honestly), the criteria for exceptions, the trigger to revisit. Hiring slowdowns communicated as strategic refocusing rather than financial reality lose trust.
15. Org structure change rationale
Current structure: [paste reporting lines]. Proposed change: [paste]. Trigger: [paste, e.g. scale, conflict, gap, growth area]. Draft a 500-word org change rationale memo: the specific problem the change solves (not 'better alignment'), the people-level impact named (whose responsibilities change, who reports to whom), the transition plan and timeline, the metrics that would tell us the change worked, the cost (every reorg has cost: people leaving, dropped balls, learning curve). Reorgs without measurable problem statements produce more reorgs.
16. Comp band review
Function: [paste]. Current band: [paste levels with ranges]. Market data source: [paste, e.g. Pave, Carta, recruiter input]. Issues: [paste, e.g. retention, hiring, internal compression]. Draft a 400-word comp band review: the gap between current bands and market (by level, in dollars), the recommendation (hold, adjust X percent, restructure levels), the cost implication, the rollout sequence (typically: lowest paid first, then compression cases, then top), the decision deadline. Comp band drift produces retention and hiring issues that take quarters to surface; the review is preventive.
17. Manager coaching plan
Manager: [paste tenure, level, team size]. Issue: [paste, e.g. weak feedback, hands-off, micromanage, low trust]. Evidence: [paste, e.g. skip-level signals, 360 results, peer input]. Draft a 400-word manager coaching plan: the specific behaviors to change, the specific behaviors to build, the cadence (weekly 1:1, monthly skip-level review, quarterly 360 retest), the timeline (typically 90 days to see signal, 180 to see change), the decision point if no progress (move out of management, exit). Coaching plans without timelines and decision points become permanent.
18. Backfill vs replace decision
Departing role: [paste title and level]. Why departing: [paste]. Team context: [paste current workload, gaps]. Draft a 400-word backfill memo: the question of whether the role should be backfilled at all (would the work survive consolidation), the level question (same level, more senior, more junior), the timeline urgency, the budget implication, the recommendation. Default-backfill produces org bloat; this prompt forces the question of whether the role still needs to exist.
19. Team-level RACI
Team: [paste]. Recurring decisions or workflows: [paste 5-8 examples that have ambiguity]. Draft a 500-word RACI memo for this team: the top decisions or workflows, the responsible (does the work), accountable (signs off), consulted (input before), informed (told after) for each, the specific cases where the current ambiguity has caused issues, the rollout sequence. RACI documents that try to cover everything become useless; this prompt focuses on the 5-8 actually-ambiguous decisions.
20. Founder-CEO one-on-one prep
Standing topics: [paste]. New topics: [paste]. Asks of CEO: [paste]. Draft a 300-word one-on-one agenda for the CEO: the two issues requiring CEO decision (with options and my recommendation), the one issue requiring CEO awareness (no decision, just heads-up), the one ask (resource, decision deadline, calibration), the question I have for the CEO (what is on their mind that is not on this list). CEO one-on-ones that drift across function status updates waste both people's time.
Category 03: Strategic Operations
Ten prompts for the strategic operations work that translates strategy into operating decisions. The shape: strategic plan teardowns that name the actual bet, OKR reviews that produce action not slides, build-vs-buy decisions with named tradeoffs, customer concentration risk analysis. Reject the 'strategic alignment' / 'north star' / 'flywheel' framing that produces decks no one acts on.
Pairs with: 8-Component Skeleton framework
21. Strategic plan teardown
Current strategic plan: [paste, ideally 1-2 page summary]. Time horizon: [paste]. Resources committed: [paste people, dollars]. Draft a 600-word strategic plan teardown: the actual bet the plan represents (the one or two assumptions that, if wrong, kill the plan), the resource allocation honestly (where most people and dollars actually go vs where they should), the strategic alternatives that were rejected (and why), the leading indicators that would tell us the bet is working or failing in 90 days. Strategic plans that survive teardown have a clear bet and a kill criterion; ones that do not are wishlists.
22. Quarterly OKR review
Last quarter OKRs: [paste objectives and key results with progress]. This quarter context: [paste]. Draft a 500-word OKR review: the OKRs that hit (and what we learned), the ones that missed (cause: priority drift, capacity, definition, external), the OKR carryforward decisions (kill, modify, recommit), the new OKRs for next quarter ranked by strategic importance, the explicit tradeoff (what we are not doing because of this list). OKR reviews that produce no kills are aspirational; quarters compound when this prompt forces tradeoffs.
23. Build vs buy vs partner decision memo
Capability needed: [paste]. Current state: [paste]. Build option: [paste cost and timeline]. Buy option: [paste vendors and pricing]. Partner option: [paste]. Draft a 600-word build-buy-partner decision memo: the specific use case requirements, the three options scored on cost, timeline, fit, ongoing burden, and switching cost, the recommendation with named tradeoffs, the migration or implementation path, the kill criterion if the chosen option fails. Build-vs-buy decisions made without explicit option scoring tend to default to build (engineering optimism) or to whoever pitched last.
24. Market entry analysis
New market or segment: [paste, e.g. geographic, customer segment, vertical]. Current revenue: [paste]. Investment to enter: [paste]. Draft a 600-word market entry memo: the strategic rationale for entering this market (and what we lose by not entering), the realistic year 1, year 2, year 3 revenue scenarios, the resource requirement (people, capital, time), the kill criteria (specific metrics by specific dates), the strategic alternative (where else this resource could go). Market entry memos that show only the upside case are pitches; this version names the kill criterion.
25. Pricing strategy refresh
Current pricing structure: [paste]. Issues observed: [paste, e.g. churn at price points, hesitation in sales, expansion not happening]. Draft a 500-word pricing strategy refresh: the strategic question (are we underpriced, overpriced, or wrong-structured), the data that would answer it, the three pricing options with named customer-segment impact, the rollout decision (grandfather existing, force migration, optional migration), the rollout sequence. Pricing refreshes that copy a competitor's structure without understanding our customer base produce churn.
26. Customer concentration risk assessment
Top 10 customers as percent of revenue: [paste]. Top customer revenue concentration: [paste percent]. Customer health by top 10: [paste]. Draft a 400-word concentration risk memo: the realistic loss scenarios for the top 3 customers, the revenue impact and runway implication of each, the specific risk-reduction actions (multi-year contracts, expansion, segment diversification), the priority ranking. Customer concentration risk that is acknowledged but not actioned is a liability that compounds.
27. Vendor consolidation plan
Current SaaS spend: [paste annual]. Tool count: [paste]. Top 10 tools by spend: [paste]. Overlap or unused: [paste]. Draft a 400-word vendor consolidation memo: the consolidation candidates ranked by savings, the specific function being consolidated and the surviving tool, the migration cost (people time, switching), the net annual savings, the decision sequence. Vendor consolidation projects that try to consolidate everything fail; this prompt focuses on the top 5-10 consolidation candidates by savings.
28. M&A readiness assessment
Current state: [paste financial, ops, legal]. Strategic goal: [paste, e.g. acquire to fill gap, acquire to consolidate, prepare for sale]. Draft a 600-word M&A readiness memo: the readiness gaps for the goal (financial reporting cleanliness, contract assignability, IP cleanliness, customer concentration, key person risk), the priority closing for each gap, the realistic timeline to readiness, the cost of readiness work, the trigger to start. M&A processes that begin without readiness work add 6-12 months and reduce price.
29. Product priority forcing function
Current product roadmap: [paste]. Resources: [paste engineering capacity, design, PM]. Customer demand: [paste signals]. Draft a 500-word product priority forcing memo: the top 3 things the team will ship next quarter (named in user-facing terms not feature names), the explicit list of what we are not shipping (typically more useful than what we are shipping), the rationale for the prioritization, the customer or revenue impact estimate. Roadmaps that try to do everything ship nothing well; the explicit not-shipping list is the discipline.
30. Geographic expansion decision
Markets considered: [paste with current activity]. Strategic context: [paste, e.g. customer pull, competitive coverage, partnership opportunity]. Draft a 600-word geographic expansion memo: the rationale for expansion (customer pull or strategic positioning), the specific market chosen with revenue and cost projections, the operational requirements (legal entity, hiring, compliance, local partner), the kill criterion (specific revenue threshold by specific date), the alternative use of the same resource. Geographic expansion that adds one market a year compounds; expansion to 3+ markets in parallel usually fails one or all.
Category 04: Process and Systems Operations
Ten prompts for the process and systems operations work that determines whether the company runs smoothly or accumulates friction. The shape: process audits that name the bottleneck, tool stack rationalizations, approval workflow redesigns, decision logs, meeting hygiene policies. Reject the 'operational excellence' / 'continuous improvement' framing that produces process documents no one follows.
Pairs with: Founder Pack
31. Process audit and simplification
Process: [paste, e.g. expense approval, hiring, customer onboarding, contract review]. Current steps: [paste]. Time per step: [paste]. Pain points: [paste]. Draft a 500-word process audit: the specific bottleneck (the step that consumes the most time or fails most often), the cause (approval depth, tool, handoff, ambiguity), the simplified design with fewer steps, the trade-off explicit (we lose X to gain Y), the rollout sequence. Process audits that try to fix everything stall; this prompt focuses on the one bottleneck.
32. Tool stack rationalization
Tools by function: [paste]. Annual cost: [paste]. Adoption rate: [paste if known]. Overlap: [paste]. Draft a 400-word tool rationalization memo: the tools to keep (with the function they own), the tools to consolidate (with the surviving tool), the tools to kill, the annual savings, the migration plan with specific dates. Tool stack rationalization without specific kill decisions and dates leaves the stack as-is; this prompt forces decisions.
33. Approval workflow redesign
Current approval workflow for: [paste decision type, e.g. expenses, hires, contracts, vendors]. Current path: [paste]. Average time to approval: [paste]. Draft a 400-word approval workflow redesign: the specific decisions that should be pushed down (with the threshold), the decisions that should still escalate (with the threshold), the named approver at each level (not 'leadership'), the SLA for each level. Approval workflows that route everything up consume executive time on small decisions; clear thresholds free that time for the big decisions.
34. SLA framework for internal teams
Internal team: [paste, e.g. legal, finance, IT, people ops]. Current request volume: [paste]. Common request types: [paste]. Draft a 400-word internal SLA framework: the request categories (urgent, normal, project), the SLA for each in business hours not days (and the specific business-hour definition), the intake process (specific channel and required info), the escalation path. Internal SLAs that are aspirational without intake discipline produce friction; the intake form is half the work.
35. Decision log template
Decision domain: [paste, e.g. product, pricing, hiring, vendor]. Current state: [paste, ad hoc, partial documentation]. Draft a 400-word decision log template and rollout: the fields (decision, date, decision-maker, alternatives considered, rationale, expected outcome, review date), the storage and access (specific tool and permissions), the rollout (start with new decisions, do not retroactively log, review quarterly), the discipline. Decision logs that go beyond a few minutes per decision become abandoned; this template is fast.
36. Meeting hygiene policy
Current meeting load: [paste, e.g. average meetings per week, recurring meetings]. Meeting friction observed: [paste, e.g. no agendas, drift, no decisions]. Draft a 500-word meeting hygiene memo: the specific policies (agenda required 24 hours before, decision-or-cancel rule, default 25/50 minutes not 30/60, recurring meetings auto-cancel quarterly unless re-justified), the enforcement mechanism, the meeting types this excludes (1:1, all-hands), the rollout sequence. Meeting hygiene policies that are unenforced produce no change; this version names the enforcement.
37. Dashboard rationalization
Current dashboards: [paste count by team]. Most-used: [paste if known]. Owned: [paste who maintains each]. Draft a 400-word dashboard rationalization memo: the dashboards to keep (with the decision they support), the dashboards to consolidate, the dashboards to kill (most are watched once a quarter and not actually used), the metric ownership (every metric has one owner), the maintenance cadence. Dashboard sprawl produces metric fatigue; this prompt forces the question of which decisions the dashboards actually support.
38. Documentation debt cleanup
Documentation surface: [paste, e.g. wikis, runbooks, policies, onboarding docs]. State: [paste honest assessment, e.g. 30% current, 50% stale, 20% unknown]. Draft a 500-word documentation debt memo: the highest-leverage documents to update first (typically: hiring, onboarding, on-call runbooks, security policies), the cleanup approach (kill stale, consolidate duplicates, label currency, owner per doc), the cadence (quarterly review, owner-driven), the trade-off (engineering or function time spent on docs vs other work). Documentation that is aspirationally complete is usually documentation no one reads.
39. Cross-functional handoff design
Handoff: [paste, e.g. sales to CS, marketing to sales, product to support, finance to executive]. Pain points: [paste]. Draft a 400-word handoff design: the specific information that must transfer (in a structured format not free text), the system that holds the information (specific tool not Slack threads), the SLA for the handoff, the recovery if information is missing, the metric that would tell us the handoff is working. Cross-functional handoffs that depend on goodwill and Slack break under volume.
40. Quarterly retro that produces change
Period: [paste]. Major events: [paste, e.g. launches, incidents, hires, losses]. What worked: [paste]. What did not: [paste]. Draft a 500-word quarterly retro: the three things to keep doing (named at the action level, not 'good communication'), the three things to change (with the specific change, owner, and timeline), the one thing to stop entirely, the metric that would tell us the change worked, the next retro date. Retros that produce 'communicate better' as an outcome produce no change; this version forces specific actions and owners.
Category 05: Communication and Decision Operations
Ten prompts for the communication and decision operations work that determines whether the company gets the right information at the right time or runs on rumor and last-meeting impressions. The shape: board memos that earn trust, all-hands messages that do not bullshit, post-mortems that name the cause not the person, decision memos that decide. Reject the 'storytelling' / 'narrative arc' / 'amplify the message' framing that performs communication while obscuring the substance.
Pairs with: Founder Pack
41. Board memo structure
Board meeting in: [paste days]. Last meeting: [paste date]. Major events since: [paste]. Asks: [paste decisions or input needed]. Draft a 700-word board memo: the executive summary (3-5 bullets, the most important things the board needs to know), the financial update (numbers and variance, no narrative), the strategic update (what changed in the bet), the operational update (key metrics with trend), the asks (specific decisions, named, with options and recommendation), the risk update (new and changing risks). Board memos that are 30 pages of slides without an executive summary fail to use board time.
42. Difficult update to investors
Update topic: [paste, e.g. miss, layoff, key person departure, strategy shift]. Investors to update: [paste]. Draft a 500-word investor update: the news named directly in the first paragraph (no preamble), the cause (factual, not narrative), the response (what we are doing), the implication for the business (revised forecast or trajectory), the ask if any (introduction, follow-on, advice). Investors who hear hard news from secondhand sources lose trust; investors who hear it from the founder/CEO directly with a plan generally hold.
43. All-hands message that does not bullshit
Topic: [paste, e.g. quarterly results, layoff, strategic shift, key win]. Audience: [paste team size and composition]. Draft a 400-word all-hands message: the news named in the first sentence (no preamble), the context (what changed, what did not), the implication for the team (work, structure, expectations), the ask (what the team should do, where to ask questions), the timeline for next update. All-hands messages that bury the news in narrative produce rumor; this version puts the news first.
44. Post-mortem that names the cause not the person
Incident: [paste, e.g. outage, customer escalation, missed deadline, missed forecast]. Impact: [paste]. Draft a 600-word post-mortem: the timeline of events, the root cause (technical, process, decision, judgment, named without blame), the contributing factors, the decisions that would have prevented it (with the trade-off named), the action items with owners and dates, the system change to prevent recurrence. Post-mortems that name a person produce defensive culture; post-mortems that blame 'process' without naming the specific decision produce no change.
45. Decision memo format
Decision: [paste]. Context: [paste]. Options: [paste]. Draft a 500-word decision memo: the question being decided in one sentence, the recommended option, the alternatives considered (with the reason rejected), the tradeoffs explicit (what we lose with each option), the implementation path, the review date and metric. Decision memos that recommend without naming the alternatives produce decisions that get re-litigated when the alternative comes up later.
46. Pre-mortem template
Project or initiative: [paste]. Timeline: [paste]. Stakes: [paste]. Draft a 400-word pre-mortem: the question 'imagine this initiative failed in 6 months: what would have caused it', the top 5 risks ranked by likelihood and impact, the mitigation for each, the kill criterion (the metric or signal that would tell us to stop or pivot), the decision-maker for the kill. Pre-mortems run before the launch surface risks the team is reluctant to name during launch enthusiasm; the kill criterion is the operational discipline.
47. Customer escalation response
Customer: [paste with revenue, contract length, expansion potential]. Escalation: [paste issue]. Internal context: [paste, e.g. our error, their error, ambiguous, edge case]. Draft a 400-word escalation response: the named acknowledgment of the issue (factual, no 'we hear you'), the cause from our side (if it was us, name it; if not, state the cause), the specific resolution offered, the timeline, the relationship-level follow-up (who owns the next 30 days). Escalation responses that perform empathy without owning the cause produce repeat escalations.
48. Cross-functional disagreement resolution
Disagreement: [paste, e.g. product vs sales on roadmap, finance vs hiring on headcount, ops vs CS on workflow]. Each side's position: [paste]. Draft a 500-word resolution memo: the actual disagreement named (often it is not the surface issue), the underlying tradeoff (resource, philosophy, timing), the decision-maker (named), the decision with rationale, the implementation path, the review date. Cross-functional disagreements that get resolved by the loudest voice or the last meeting produce repeated cycles; this prompt forces the named decision-maker.
49. Crisis communication playbook
Crisis type: [paste, e.g. security incident, product failure, public dispute, executive departure]. Stakeholders: [paste, e.g. customers, employees, investors, press]. Draft a 700-word crisis comms playbook: the first-hour actions (named owner per action), the stakeholder communication sequence (typically: employees first, then customers, then investors, then press), the holding statement (factual, no 'we are aware'), the escalation criteria for full disclosure, the legal review checkpoint, the post-crisis review trigger. Crisis comms playbooks that are written during the crisis fail; this version is written before.
50. Executive summary that earns the next paragraph
Document or memo: [paste topic and length]. Reader: [paste, e.g. CEO, board, all-hands]. Draft an under-150-word executive summary: the question being addressed, the one-line answer, the three key points that support the answer, the ask of the reader (decision, awareness, action). Executive summaries that read like abstracts fail to get the document read; the answer comes first, the supporting points second, the ask explicit.
How the prompts fit a real operator week
Monday: weekly business review prep. Variance analysis, key metric review, decision queue review. The Monday memo is the steering wheel for the week.
Mid-week: hard conversations and decision memos. The work that gets pushed if not scheduled. Block the time on Tuesday or Wednesday morning.
Thursday: process and systems work. Tool stack, approval workflows, documentation debt. The unglamorous work that compounds when done weekly.
Friday: communication. Board memo drafts, all-hands message drafts, customer escalation responses. Friday afternoon write means Monday morning publish.
Monthly: close, comp band review, headcount cost model, vendor renegotiation pack. The monthly cadence catches the medium-frequency issues.
Quarterly: OKR review, strategic plan teardown, retro that produces change. The quarterly cadence catches strategic drift.
Five mistakes that wreck operator prompts
1. Filling in the prompt with vibes instead of numbers. The prompts ask for specific dollars, dates, percentages. Filling them with "high", "low", "growing" produces output of the same low calibration. The discipline is putting the actual numbers into the inputs.
2. Using the prompts as decks rather than memos. The output is engineered for memo register: flat, factual, named owners and dates. Re-formatting the output as slides defeats the purpose; slides are for board meetings, memos are for decisions.
3. Skipping the prompts that ask uncomfortable questions. The customer concentration risk prompt, the layoff decision memo, the walking-from-a-vendor prompt. The avoided prompts are usually the ones with the most leverage. Notice the avoidance.
4. Treating the recommendation as the answer. The prompts produce a recommended option with named alternatives. The point is the structured comparison, not the recommendation. The recommendation is the LLM's; the decision is yours.
5. Running the influencer-genre prompts instead of these. Prompts that produce "10x your operations" outputs reinforce the genre this pack rejects. Calibration to the picks-influencer voice produces threads not memos.
Questions people ask
Who is this pack for? CFOs, COOs, Chiefs of Staff, Heads of Operations, VP Operations, and senior operators in any function. Most useful for late-stage startups (Series B+), professional services firms, PE portfolio operators, and corporate operators inside large companies. The prompts assume basic operator literacy: P&L reading, variance analysis, decision-memo writing, performance management.
Does it work for early-stage founders without a CFO yet? Partially. The Financial Operations category requires actual financial data; the People Operations category assumes a team of 10+. The Strategic Operations and Communication categories work earlier. Pair with the Founder Pack for the founder layer.
Does it work for non-tech companies? Yes. The pack is calibrated for the operator role independent of industry. Most prompts work for professional services, family-owned businesses, PE portfolio companies, and corporate operators inside large companies. The Strategic Operations category is the most industry-agnostic; the FP&A category may need adaptation for service businesses with different unit economics.
What output format does it produce? Memo register: flat, factual, named tradeoffs, specific owners and dates. The opposite of LinkedIn-thread register. The prompts explicitly ban the influencer-genre phrases listed at the top.
The other free packs in the franchise
Same calibration discipline, different audiences. Daily B2B work: 100 B2B Mega Pack. Founder GTM: 50 Founder GTM Pack. Crisis moments: 100 Issues and Escalations Pack. Personal life: 100 Personal Productivity and Life Pack. Sports betting and markets: 50 Sports Betting Pack. All free.
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