It has been
8 days
since the date nobody puts on their calendar.
Every September, a board quietly decides whether the CRO is running next year's number.
Every September, a sales leader quietly decides who's on their team for the next year.
Nobody sends a meeting invite for it,
and most people find out where they stood only after the decision's already been made.
The AI Prompts are designed for the turnover toolkit to help you make it through that time.
They're also bonus content for The CRO's Guide to Winning in Private Equity and The AI Handbook for Sales Professionals
but you don't need to purchase either book to get these tools.
I want you to help me run a talent nine-block review for my team. Here's the framework we're using:
The nine-block scores each person on two axes — Performance (Low/Medium/High) and Potential (Low/Medium/High) — producing nine boxes:
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High Performance / High Potential = Future Leader (top box; actively develop, but watch for retention risk if under-challenged)
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High Performance / Medium Potential = Rising Star (strong now, real room to grow; priority development)
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High Performance / Low Potential = Solid Professional (reliable, capped in current scope; protect and retain, don't assume they want a bigger role)
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Medium Performance / High Potential = Emerging Talent (potential ahead of output; check for a ramp, territory, or coaching gap)
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Medium Performance / Medium Potential = Core Performer (the backbone of most teams; don't ignore this box because it isn't dramatic)
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Medium Performance / Low Potential = Inconsistent Player (coach the gap between effort and output before assuming it's a fit problem)
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Low Performance / High Potential = Diamond in the Rough (potential is real, something specific is blocking it — diagnose before deciding)
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Low Performance / Medium Potential = Misplaced or Underperforming (often the start of a development-plan conversation)
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Low Performance / Low Potential = New/Ramping or Genuinely Stuck (tell the difference before this becomes a PIP)
Here's how I want to work through this with you, one person at a time:
Step 1 — Quantitative input. Ask me for this person's quota attainment (current period and trailing trend), and their forward pipeline coverage relative to where they need to be. Keep this brief — it's an input, not the whole conversation.
Step 2 — Qualitative input. Ask me: their flight/retention risk, morale, and anything going on in their territory, ramp stage, or personal life that the numbers alone wouldn't show. Push me for something specific here, not just "seems fine."
Step 3 — Placement. Based on what I've told you, tell me which of the nine boxes this person lands in and explain your reasoning in a sentence or two, referencing the specific inputs I gave you.
Step 4 — Development action. This is the part I actually need help with, not just the label. Based on the box, help me build one concrete, specific next step — not generic advice. If it's a Future Leader, help me think about a stretch assignment or expanded scope, and flag the retention-risk angle explicitly. If it's a Rising Star or Emerging Talent, help me identify the one skill or coaching gap most worth closing next. If it's a Core Performer, don't let me skip them — ask what would move them one box in either direction, and whether that's even the goal this cycle. If it's Inconsistent Player, Diamond in the Rough, or Misplaced/Underperforming, help me separate a genuine skill or fit problem from a ramp, territory, or circumstantial issue before we default to a Development Plan — and if we do need one, tell me and I'll bring you the Personal Development Plan prompt for that instead of trying to solve it here.
Step 5 — Repeat or summarize. Ask if I want to go through another person, or if I'm done, summarize everyone I've reviewed today in a simple table: name, box, one-line reasoning, and the development action — something I could paste into notes for my next one-on-one with each person's manager.
One more thing: if at any point what I describe sounds more like a performance problem than a talent-placement question, tell me directly and suggest we switch to the Personal Development Plan conversation instead of forcing it into a box.
Nine-Block Talent Placement & Development Planner
Walks you through placing employees on a nine-block grid and then turns that placement into an actionable next step.
COPY PROMPT
I want you to help me draft this week's flash report — a short weekly email to my frontline managers, VPs, exec team, and board, covering bookings and pipeline generation.
Step 1 — Get the numbers. Ask me for: bookings this week, broken down by team and region; pipeline generated this week, same breakdown; and how this week's numbers compare to a normal week for us.
Step 2 — Find the "why." For anything that moved more than a little in either direction, don't let me just report the number — ask me what actually caused it. Push me until I can name a specific driver: a deal that closed early or slipped, a seller out on leave, a renewal at risk, a new-logo push that landed. If I don't know yet, ask me what I'd need to find out before I send this.
Step 3 — Pace-to-plan. Ask me where this leaves us against the quarter or annual number, and whether that trend is improving, holding, or worsening.
Step 4 — Draft it. Write the email in a tight, board-ready format: structured metrics first, no more than 200 words total, one line of real context per notable movement — not vague reassurance, not alarm, just what happened and what it means for pace-to-plan. If something's trending the wrong way, make sure the email says so plainly rather than burying it — the whole point of this habit is that nobody on this list should ever be surprised later by something this email could have flagged now.
Step 5 — Sanity check. Before you give me the final version, tell me honestly: does this read like I'm hiding something, or like I'm showing my math? If it reads like the former, tell me what to add.
Weekly Flash Report Builder
Turns your raw weekly numbers into a tight, board-ready update that shows your math instead of just the score.
COPY PROMPT
I want your help building my one-page annual sales plan for the year, using a structured process. Here's the methodology:
The plan starts from net retention, not from a top-down number. We're building this plan grounded in real historical data, not aspiration.
The plan breaks into these components:
Renewals — not every contract is up for renewal this year. For the ones that are, we need: current satisfaction level, contracted price-increase language already locked in, and a strategy per account (e.g., trade a bigger price increase for a multi-year term, or vice versa).
Price increases — separate from renewals: what's contractually allowed, and what's realistic.
Upsell/cross-sell — expansion revenue within the existing base, contingent on product readiness and adoption.
New logo acquisition — net retention strength changes how hard you need to lean here. Strong net retention relieves pressure on new logos; weak net retention means you need disproportionately more new-logo volume to hit the same number.
Sales force productivity — hiring, ramp time, and expected turnover, built into the plan rather than ignored.
Here's how I want to work through this with you, step by step:
Step 1 — Net retention baseline. Ask me about my current customer base: renewal timing, satisfaction levels, and contracted price-increase terms for accounts up in the next 12 months. Help me project a realistic net retention rate from this, not a hoped-for one.
Step 2 — New logo target. Based on the net retention number from Step 1, help me calculate how much new-logo volume I actually need — walk me through the math rather than just giving me a number, so I understand the relationship between the two.
Step 3 — Sales force productivity. Ask me about current headcount, expected turnover, time-to-hire, and time-to-ramp. Help me build that into the plan as a real constraint, not an assumption I'll deal with later.
Step 4 — Assemble the one-pager. Lay out the board-facing plan as a single page: total number, broken into the five components above, one line per component stating the real assumption behind it — something a board member could actually question. This is the "Board Plan" — the true baseline, not an internally inflated management version that sellers will see.
Step 5 — Sanity check. Before finalizing, ask me directly: is any part of this plan dependent on something that hasn't happened yet — a product launch, a new hire, a price change not yet approved? If yes, tell me plainly that this belongs in a separate "upside" list, not the baseline plan, so a miss on that item doesn't take the whole plan down with it.
One-Page Annual Plan Builder
Walks you through building a one-page annual plan fully grounded in data.
COPY PROMPT
I want your help drafting my regular board reporting — this is a separate, recurring task from building the annual plan itself, and it runs on three different cadences: weekly, monthly, and for in-person board meetings.
Ask me which one we're doing today, then follow the right path:
If weekly: ask me for this week's bookings and pipeline generation, broken down by team and region. Draft a short flash report — data first, one line of context on anything that moved more than normal, no more than a few sentences total.
If monthly: ask me for pipeline, bookings, and forecast, each measured against the monthly, quarterly, and annual plan. Also ask about headcount versus plan and the status of any key initiatives currently in flight. Draft a one-page monthly dashboard summary: the quantitative comparison against plan first, then a short qualitative section — what's underperforming, and what's being done about it. Don't pad the underperforming section with reassurance; state it plainly.
If prepping for an in-person board meeting: the data will already be familiar to the board by this point, so don't re-explain it. Instead, ask me: what's the story behind anything that's off track, what's the response or strategy, and are there any requests I need from the board (budget, hiring approval, strategy input). Help me draft two or three slides' worth of talking points that spend the meeting on "what we're doing about it," not on re-litigating the numbers — the goal is that the board and I are aligning on strategy, not spending the meeting trying to forecast the weather together.
One check to run every time, regardless of which cadence: ask me whether everything in this report has already been discussed with the people it affects before it reaches this document. If something hasn't been, say so directly and suggest I have that conversation first — this report should read as a recap of things already known, never as the first place anyone hears the news.
Board Reporting Cadence Builder
Drafts your weekly flash report, monthly board report or in-person board talking points.
COPY PROMPT
I want your help evaluating whether my current team — or my CRO — is actually the right fit for what the business needs right now, using a structured framework. Here's the approach:
There are two different jobs a revenue leader can do: build something from scratch (creating sales processes, hiring and developing a team) or take an existing, functioning team and scale it fast for an outsized outcome. Most mismatches happen because a company hired someone great at one job when they actually needed the other — and they usually don't realize it as fast as they'd like.
Walk me through this one section at a time:
Step 1 — Stage fit. Ask me: what stage is the business at right now (early build, scaling, pre-exit), and what did this person actually do at their last two stops — not their title, but what they built or what they inherited and sharpened. Help me figure out which of the two jobs above they were actually doing, and whether it matches what this business needs next.
Step 2 — Story vs. data. Ask me to describe, in my own words, how this person explains the current number — both when they hit it and when they miss it. Then ask me: does their explanation match what the underlying data has actually been showing for the last few months, or does it feel like they're explaining around something? Push me for a specific recent example, not a general impression.
Step 3 — Whose name is in the story. Ask me to recall the last two or three updates this person gave me about a win or a save. In those stories, are they the one who closed it, or are they describing how their team executed? If most of the stories center on them personally, flag that as a possible sign they're still operating like an individual contributor rather than running the org at its current size — not a character flaw, just possibly a stage mismatch.
Step 4 — Plan quality. Ask me whether this person's plan is grounded in real historical performance, broken into challengeable components, with anything unproven kept separate as upside. If it isn't, flag that the number may be built on hope, rather than an actual plan.
Step 5 — Culture check. Ask me to rate this person, honestly, on three separate things: integrity, respect for the people around them, and results — not as one blended impression, but three distinct answers. If any one of the three is clearly weak, tell me directly that a strong score on the other two won't hold up long-term, and that's worth addressing now rather than waiting for it to show up in attrition or a data problem later.
Step 6 — Synthesis. Once we've been through all five, give me your honest read: does this look like a fit problem, a performance problem, or a communication problem? Those need very different responses, and I don't want you to default to the easiest-sounding one — push back if my answers in Steps 1–5 don't actually support the conclusion I'm reaching for.
One more thing: if at any point this starts sounding like a legal or HR-sensitive termination conversation rather than an evaluation exercise, tell me directly and suggest I loop in HR or counsel before going further — this prompt is for clarifying my own thinking, not for building a case.
Fit or Performance? Executive Evaluation Guide for Boards
Helps a board member or manager determine if their leader is a fit for the current needs.
COPY PROMPT
I want your help building an objective-to-competency table for a role I'm hiring, before I write the job description. Here's the approach: every performance objective (a quota, a deal-close target, a pipeline number) has a competency underneath it — the actual skill someone needs to hit that number in my specific environment, not a generic one.
Step 1 — Objectives. Ask me for the role's core performance objectives: quota, deal volume, pipeline targets, whatever applies.
Step 2 — Environment. For each objective, ask me about the specific environment this role operates in: sale complexity, number of buyers involved, cycle length, how much pipeline the seller has to generate themselves versus what's handed to them, whether this is a competitive-displacement sale or a category-creation sale. Push me for specifics — "enterprise software" isn't enough detail to write a real competency against.
Step 3 — Derive the competency. For each objective, propose the specific competency someone needs given the environment I described, and write a one-line "why" explaining the connection — the kind of note a candidate or hiring manager could actually read and understand.
Step 4 — Table stakes. Ask me whether there are competencies that matter regardless of the specific objectives — communication style, time management, self-direction in an ambiguous environment — and add those as a second section.
Step 5 — Sanity check. Before finalizing, ask me: is there anyone on my team, or anyone I've hired before, whose resume looked great but who failed in this specific environment? If so, ask what competency was actually missing, and check whether it's already captured in this table. If it isn't, add it. Similarly, ask me about the team members who are succeeding in the role, and probe for what they're doing that's making them successful. If those competencies are required and not already in the table, add them, too.
Give me the final result as a clean table: Objective, Competency, Notes — ready to build a job description from.
Job Description Builder with Objectives and Competencies
Turns a role's performance objectives into the competencies you need to hire for, before writing the job description
COPY PROMPT
Interview Questions and Rubric Builder
Takes your competency list and builds interview questions, a scoring rubric and interviewer assignments to test each one.
COPY PROMPT
I want your help building a structured interview process for a role, based on a competency table I already have (I'll paste it in, or we can build it together if I don't have one yet).
Step 1 — Get the competencies. Ask me for the competency list. If I don't have one, tell me to run the Job Description Builder with Objectives and Competencies prompt first, since this one depends on it.
Step 2 — Behavior-based questions. For each competency, write one or two behavior-based interview questions — always starting with "tell me about a time when..." — designed to surface a real example of the candidate demonstrating that skill, not a hypothetical answer about how they'd behave. Avoid generic questions; tie each one specifically to the competency's notes.
Step 3 — Scoring rubric. For each question, define what a 1, 3, and 5 answer actually looks like — concrete, observable differences, not vague adjectives like "good" or "great." A 3 should represent "meets the bar for this role," not "average." Provide examples.
Step 4 — Interviewer assignments. Ask me how many people will be on the interview panel, and help me assign each competency to a specific interviewer so nothing goes untested and nothing gets asked twice.
Step 5 — Consistency check. Remind me: every candidate for this role should get the exact same questions, asked the same way, so I can actually compare them. Ask me to confirm I'm ready to commit to that consistency before finalizing.
Give me the final output as a grid: Competency, Question(s), Assigned Interviewer, and the 1/3/5 scoring guide for each.
Candidate Evaluation Conversation
Talks through a specific candidate against your rubric, their resume, and what came out in the interview.
COPY PROMPT
I want to talk through a specific job candidate with you, evaluating them against my interview rubric. I'll give you the rubric, their resume, and my notes or impressions from the interview(s). Ask me to paste or upload what I have, and tell me what's missing if something's incomplete.
Step 1 — Gather. Ask me for: the competency rubric for this role, the candidate's resume, and my raw notes or recollections from the interview — what they actually said in response to the behavior-based questions, not just my overall impression.
Step 2 — Score, competency by competency. Walk through each competency on the rubric one at a time. Ask me what the candidate actually said or demonstrated for that one, and propose a 1–5 score with your reasoning. Push back if my instinct doesn't match the evidence I'm giving you — if I say "5" but the example I describe sounds more like a 3, tell me that directly.
Step 3 — Resume cross-check. For any competency where the interview evidence feels thin, check whether the resume offers corroborating (or contradicting) evidence — a track record that matches or doesn't match what they claimed live.
Step 4 — The "we hire our own problems" conversation. Once every competency is scored, tell me honestly: is this a candidate who clears the bar everywhere, or one with a specific gap? If there's a gap, don't just flag it — ask me whether I have the coaching capacity and time to close it, and whether this role can absorb that risk. Help me decide with clear eyes, not talk me into hiring someone by rounding up.
Step 5 — Recommendation. Give me a clear recommendation: offer, continue interviewing, or pass — and if it's a pass, help me draft one honest sentence I could actually say to the candidate about why, in case I want to give them that feedback.
Keep this whole conversation candidate-specific and evidence-based — don't let general impressions substitute for what I actually tell you they said or did.
I want your help building (or executing) a professional "go-bag" — the documents, contacts, and materials I'd want backed up outside of work systems in case my job access were cut off without warning. Throughout this conversation, if anything I describe sounds like it could be confidential or company-owned information rather than something I'm personally entitled to (client lists, proprietary documents, trade secrets, internal-only data), flag it and steer me toward keeping only what's mine.
First, ask me which mode I'm in:
A) Routine maintenance — I have time and want to build or update my go-bag properly.
B) I need it right now — I just got bad news and have limited time before I lose access.
If I say A (routine maintenance):
Walk me through each of these categories one at a time, asking me follow-up questions to help me actually produce the content rather than just listing what I should do:
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Performance history: help me draft a clean summary of attainment vs. quota by period, based on numbers I give you.
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Wins with numbers: help me turn rough bullet points into specific, externally-shareable language (deal size, percent above target, what I'm allowed to name publicly).
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Recommendations: help me draft 2-3 short, specific LinkedIn recommendation requests, personalized to the person and the project we worked on together, so I'm not sending a generic ask.
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Reconnections: give me a short list of low-pressure, genuine outreach messages I could send to people I haven't talked to in a while — no ask attached.
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Recruiter folder: help me write a short, polite template for acknowledging recruiter outreach when I'm not looking, that's easy to send in ten seconds.
End by giving me a simple quarterly checklist based on what we just did.
If I say B (I need it right now):
Start with one calm sentence acknowledging that this is a genuinely hard moment, and that feeling rattled is normal, not a sign I'm handling it wrong. Then ask how much time I have. Give me a short, ordered list of the highest-priority actions only — contacts, personal documents, and reference contacts — in the order I should do them, assuming I might get interrupted at any point. Keep every instruction short, concrete, and free of anything that isn't immediately actionable — no pep talks, no "silver linings," nothing that requires me to reflect. If I say anything that sounds like anger, panic, or self-blame, briefly acknowledge it without dwelling on it, then gently redirect me back to the next concrete step. Do not give me the full quarterly list. End by reminding me, in one line, that the bigger decisions can wait until later today.
The Go-Bag Builder
Walks you through building your go-bag when you have time, or triages you calmly through the five-minute version when you don't.
COPY PROMPT
I want your help sharpening my resume so it reads well to someone scanning it for thirty seconds as well as someone taking a deep dive into it. Do the following, in order:
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First-read impression. Before you suggest any changes, tell me what conclusions a first-time reader — a hiring manager or recruiter seeing this resume cold — would draw or reasonably infer from it. What story does it currently tell about my level, my strengths, and my trajectory? What would they assume I'm good at, and what would they assume I haven't done, based only on what's written? Be honest even if the answer is unflattering — I'd rather know now.
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Results vs. responsibilities. Go through every bullet point. For each one, tell me whether it describes a responsibility (what I was supposed to do) or a result (what actually happened because of what I did). For every responsibility-only bullet, propose a rewrite that states the result, with a number attached wherever one is plausible from context — and if you don't have enough information to invent a real number, ask me for it rather than making one up.
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Jargon and internal language. Flag every job title, project name, internal tool, or acronym that wouldn't mean anything to someone outside my company. For each one, suggest a plain-language alternative that describes what it actually was or did.
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Spelling and grammar. Do a full spelling and grammar pass on the document as written, separate from the content suggestions above. List each issue with the original text and the fix.
Give me your findings as four separate sections in the order above, not blended together, so I can address them one at a time.
The Resume Rewrite
Upload your current resume, get line-level rewrites to optimize impact
COPY PROMPT
I want your help drafting my weekly update email to my manager. I'll paste in rough notes, bullet points, or just a stream-of-consciousness recap of my week — it won't be organized. Turn it into a clean email with exactly these five sections, in this order:
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Numbers and forecast. Where I stand against quota or my key metrics this week, and what I expect over the next one to two weeks. Keep this section factual and specific — numbers, not adjectives.
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Commentary on changes. Anything that shifted since last week and why — a deal that moved, a timeline that slipped, a risk that showed up. Explain the "why" behind anything in section 1 that needs context.
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People Updates. Anything about my direct reports that my manager should know about this week.
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Key project updates. Where things stand on the initiatives I'm accountable for, separate from my core number.
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Miscellaneous. Anything else worth flagging — upcoming PTO, a peer I helped, something I learned.
Rules for how you write it:
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Keep the whole email skimmable in under a minute — short sentences, no filler, bullet points, no restating something in two different sections.
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If my notes don't give you enough for one of the five sections, leave it brief or say "nothing to report" rather than padding it out with vague language.
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Don't invent numbers, outcomes, or details I didn't give you — if something sounds like it needs a number and I didn't provide one, flag it with a placeholder and ask me for it.
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Write it in a professional but natural tone — like an update from a real person, not a corporate status report.
End with the finished email, ready to send as-is or lightly edited.
The Week In Review Builder
Develop a ready-to-send update to your manager, weekly.
COPY PROMPT
I want your help building a territory plan for next quarter or next year, from scratch — I don't have a company template to work from.
Start by asking me these questions, one at a time, and pushing back if my answers are vague:
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What's working right now, specifically? Not "relationships" or "my process" — what have I actually done that produced a result?
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What's not working, specifically? Where am I losing time, deals, or momentum, and why?
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What could I personally do differently next quarter that's within my control — not "work harder" or "dig deeper," but a specific, describable change in behavior?
Then walk me through building out three sections:
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Accounts. Help me think through which accounts deserve the most attention and why — not just size, but where I actually have a credible path to close. Ask me what evidence I have for that path.
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Prospecting plan. Help me get specific about how I'll generate new pipeline — which channels, how often, and roughly how much volume I'm committing to.
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Activities and metrics. Help me identify leading indicators I can track weekly, not just the lagging number I'm judged on at the end of the quarter.
Throughout, hold me to this standard: if a hiring manager or my own manager read what I just said, would they know exactly what I'm going to do differently, and why it should work? If any answer is still vague — like "I'll sell more" or "I'll be more proactive" — push me to get specific before moving on.
End with a clean, one-page summary of the plan we built, organized under the three headings above.
The Territory Plan Builder
Develop a real plan that gives everyone confidence about your success next quarter
COPY PROMPT
I want your help building a 90-day personal development plan for myself — either because my manager hasn't offered one, or because I want to walk into that conversation prepared instead of just reacting.
Walk me through these five steps, one at a time, and push me to be specific and honest rather than generic:
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Self-assessment. Ask me what I think my current strengths and gaps are, in my own words, before I've talked to my manager about it. Push back if I'm vague ("I need to be more strategic") and ask me to make it concrete. Ground them in how they relate to my specific job assignment and thoughts about future jobs.
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SMART objectives. Help me turn my self-assessment into a small set of Specific, Measurable, Achievable, Relevant, Time-bound goals for the next 90 days — objectives I could actually bring to my manager as a starting point for a real conversation, not a wish list.
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Underlying skills. For each objective, ask what skill or capability actually needs to improve to hit it — not just the number I'm supposed to produce, but what has to get better to produce it.
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Concrete actions. Help me turn each skill gap into a specific action — a type of training, a person I could ask to mentor me, a stretch assignment I could request — something specific enough to put in writing, not "try harder."
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Check-in cadence. Help me draft a short, low-pressure way to ask my manager for a weekly or biweekly check-in on this plan, rather than waiting for a quarterly review to find out how I'm doing.
End with a one-page summary of the plan, organized under: Self-Assessment, 90-Day Objectives, Skills to Develop, Action Steps, and Check-In Cadence — something I could actually bring into a conversation with my manager.
Personal Development Plan
Turn a quarterly review into a 90-day plan you and your manager agree on.
COPY PROMPT
I'm going to upload or paste in a separation agreement I've been given. I want your help understanding it and thinking through what might be negotiable — not legal advice, just a starting point before I talk to an attorney.
Do the following:
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Plain-language summary. Summarize what the document actually says, section by section, in language a non-lawyer can understand. Call out anything that seems unusual, unusually broad, or unusually restrictive compared to a typical separation agreement — but don't guess at legal validity or enforceability.
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What's already being offered. List everything the document currently provides — severance amount and structure, benefits continuation, equity treatment, PTO payout, notice period, outplacement, references, and anything else you find.
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What might be worth asking about. Based on what is and isn't in the document, and drawing on this list of commonly negotiable items — severance amount and structure, timing of payments, health insurance continuation, equity vesting, bonus and PTO, notice period or pay in lieu, outplacement services, references and characterization of departure, non-compete/non-solicit terms, equipment retention and more — flag anything that's missing, unusually limited, or worth raising. Be specific about what's actually absent or thin in my document, not generic.
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Timing considerations. If there's anything about when payments are scheduled, flag whether the timing could matter for taxes (e.g., a payment landing in December versus January) or benefits like 401(k) matching, and suggest it's worth discussing with an accountant or attorney.
Before your response, and again at the end, remind me clearly: this is not legal advice, you are not a lawyer, and before signing anything I should have this reviewed by an actual employment attorney — especially if I'm giving up the right to sue, or if anything in the document is unclear to me.
Separation Agreement Review
Upload your separation agreement and get a plain-language summary, flagged points worth exploring further, and a clear reminder that this isn't a substitute for working with an attorney
COPY PROMPT
Disclaimer / Terms of Use for AI Prompts and Templates
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