10 prompts every mid-market executive should have on file.

Use when you're about to make a significant decision and want a sharp critic before you sign.

Act as a sceptical strategist who has seen this kind of decision fail before.

Decision I'm about to make: [DESCRIBE THE DECISION IN 2–3 SENTENCES]
Context: [COMPANY STAGE, MARKET, TEAM SIZE, RELEVANT CONSTRAINTS]
Why I think it's right: [YOUR CURRENT REASONING IN 3 BULLETS]

Do four things, in order:
1. Identify the single strongest argument against this decision. Don't hedge.
2. Generate three questions a sceptical board member would ask me before approving it.
3. Describe what a wrong version of this decision looks like 12 months from now — be specific about the failure mode.
4. Tell me one piece of information I should gather this week before committing.

Be direct. I want a critic, not a cheerleader.

Use for quarterly board updates when you have the data but not the time.

You are drafting a quarterly board update for a mid-market company.

Inputs:
- Headline financials vs. plan: [REVENUE, MARGIN, CASH, RUNWAY]
- Period: [QUARTER]
- Key initiatives and status: [LIST]
- Notable customer / market events: [LIST]

Produce a board update with exactly these sections:
1. Headline (2 sentences — the one thing the board must remember).
2. Financials vs. plan (3 bullets, each with the number and the why).
3. Three wins worth naming (1 line each, named outcomes not activity).
4. Three concerns with mitigations (1 line concern + 1 line mitigation).
5. Top initiative status (RAG with one-line reason).
6. One strategic question framed for board discussion (not yes/no).

Tone: confident, specific, no jargon. Length: under 400 words.

Drop 50+ customer emails and get classified, ranked, and ready to action.

Act as a senior customer operations lead.

Below are [N] customer emails. For each one, return a single row:
| # | Customer | Urgency | Underlying concern (≤5 words) | Suggested response opener | Churn risk? |

Rules:
- Urgency = HIGH / MEDIUM / LOW based on tone, business impact, and explicit asks.
- Match the suggested opener to the customer's tone (warm / formal / frustrated).
- Flag "Churn risk: YES" only on HIGH items where the email signals exit, escalation, or repeated unresolved issue.
- Do not paraphrase the entire email. Be ruthless about brevity.

Sort the table HIGH → MEDIUM → LOW.

Emails:
[PASTE EMAILS HERE, SEPARATED BY "---"]

Run weekly to stay sharp on the three competitors that actually matter.

Act as a competitive intelligence analyst for a [INDUSTRY] mid-market company.

My top 3 competitors: [COMPETITOR A, B, C]
My company's current focus: [1–2 SENTENCES]

Using publicly available information from the past 7 days (press, product launches, hires, pricing, partnerships):
1. Summarise the most important move from each competitor in 2 sentences.
2. For each move, explain in 1 sentence why it matters for my company specifically.
3. Name the single competitor move that deserves closest attention this week, and what I should do about it (one concrete action).

If you cannot verify a claim, say "unverified" rather than guessing. End with a 1-line "what I'd watch next week".

Generates non-generic discovery questions and surfaces the angle most people would miss.

Act as a senior advisor preparing me for a meeting.

Meeting context:
- Who I'm meeting: [NAME, ROLE, COMPANY]
- Their company: [WHAT THEY DO, STAGE, RELEVANT FACTS]
- The reason for the meeting: [1–2 SENTENCES]
- What I want out of it: [SPECIFIC OUTCOME]

Produce:
1. Five non-generic discovery questions specific to their business — no "tell me about your goals".
2. Three likely objections they will raise, each with a one-line response that lands.
3. One strategic angle most people in my position would miss in this conversation, and how to bring it up naturally.

Keep it under one page. No filler.

Rewrites a job description so it actually attracts the right operator.

Act as a hiring partner who has placed senior operators into mid-market companies.

Below is a draft job description. Rewrite it so:
1. The first paragraph names the actual problem this person will solve in their first 90 days — not a list of responsibilities.
2. It is honest about constraints (team size, budget, reporting line, what's broken today).
3. It signals the type of operator we want (builder vs. optimiser, generalist vs. specialist) without using those words.
4. It ends with one filter question that only the right candidate will answer well.

Keep it under 350 words. Cut every sentence that could appear in any other JD.

Draft:
[PASTE DRAFT JD HERE]

Turns a transcript or rough notes into a clean decisions / actions / open-questions log.

You are a chief of staff turning meeting notes into a clean decision log.

Notes / transcript:
[PASTE HERE]

Produce three sections, in this exact order:

DECISIONS MADE
- [Decision] — Owner: [name] — Effective: [date]

ACTION ITEMS
- [Action] — Owner: [name] — Deadline: [date]

OPEN QUESTIONS DEFERRED
- [Question] — Needed by: [date or trigger]

Rules:
- If a decision, owner, or date is ambiguous, flag it as "AMBIGUOUS — needs confirmation" rather than guessing.
- Do not include narrative or summary. Decisions and actions only.

Five-sentence executive commentary on monthly P&L — ready to edit, not rewrite.

Act as a CFO writing executive commentary for a monthly management report.

Inputs:
- Period: [MONTH]
- Revenue actual vs. plan: [NUMBERS]
- Gross margin actual vs. plan: [NUMBERS]
- Cash on hand and runway: [NUMBERS]
- One operational signal worth flagging: [METRIC + DIRECTION]
- Forward note from the leadership team: [1 LINE]

Write exactly 5 sentences:
1. Revenue movement vs. plan and the dominant cause.
2. Margin movement and the root cause (mix, pricing, cost).
3. Cash position and runway in plain terms.
4. The one operational signal and what it implies.
5. One forward-looking note for the next 30 days.

No hedging, no "we will continue to monitor". Concrete language only.

Turns a call transcript into both an internal team summary and a customer follow-up email.

You will produce two outputs from the transcript below.

OUTPUT 1 — Internal team summary (5 lines, no more):
- Customer's intent (why they took the call)
- Their main concern
- One positive signal
- Commitments made (with deadlines and owners)
- One thing not to forget next time

OUTPUT 2 — Customer follow-up email (under 150 words):
- Warm, specific opener referencing what they actually said
- Confirms commitments with dates
- One clear next step with a proposed time
- No corporate filler

Transcript:
[PASTE TRANSCRIPT HERE]

Sorts a long list of candidate priorities into clear-yes / clear-no / depends.

Act as an operating partner helping me set quarterly priorities.

Company context: [STAGE, REVENUE, TEAM SIZE, STRATEGIC FOCUS]
Quarter goal in one sentence: [GOAL]

Below is a list of [N] candidate priorities. Group every item into exactly one bucket:

CLEAR YES
- [Priority] — Outcome it produces this quarter: [1 LINE]

CLEAR NO
- [Priority] — Cost of doing it anyway: [1 LINE]

DEPENDS
- [Priority] — The question whose answer determines the call: [1 LINE]

Be decisive. "Depends" should be the smallest bucket, not the largest.

Candidates:
[PASTE LIST]