The Ultimate ChatGPT Prompt Library for B2B Sales Leaders

You are scanning the current pipeline for deals likely to slip or fall through. Using CRM and call sentiment data, find the top 3 open deals (especially ones in Commit) that show risk signals: e.g., no customer activity in >14 days, negative tone on last call (like concerns about budget), or missing decision maker involvement. For each deal, give a brief summary of the risk ("Deal <DEAL_NAME>: last contact 3 weeks ago; competing vendor in play" or similar) and the potential revenue impact if lost ("if lost, team falls to 85% of quota"). Recommend a mitigation step for each (schedule exec call, adjust offer, etc.). Keep details anonymous (no customer names) and focus on the action needed. This will be used to focus the team on saving key deals.

Fewer surprise deal slips – e.g., 100% of identified risky deals are either closed or reforecasted appropriately

Warning: Automated risk flags aren’t perfect. Always double-check with the account owner; a deal might look inactive in CRM but still be progressing offline. Use these flags to start conversations, not as definitive conclusions.

You are doing a win/loss analysis using CRM notes and call recordings. Take one recent big win and one big loss and compare them. Identify 3 factors that contributed to the win (e.g., strong champion, superior product fit, timely executive involvement) and 3 factors for the loss (e.g., price was too high, competitor had key feature, low engagement from economic buyer). Paraphrase any customer feedback from call recordings (no direct quotes or names) that illustrate these points. Then provide one recommendation for the sales team: how to replicate the win factors more often, and one on how to avoid or mitigate the loss factors. Present the findings as a brief "lessons learned" summary for the next sales meeting.

Win rate improvement (+X% next quarter) by applying identified lessons

Blind Spot: Individual win/loss stories can be anecdotal. Validate patterns across multiple deals before overhauling strategy – don’t generalize from a single data point without further evidence.

You are a sales manager reviewing a high-value opportunity <DEAL_NAME> in the CRM. Use the MEDDIC framework (Metrics, Economic Buyer, Decision Criteria, Decision Process, Identify Pain, Champion) to evaluate this deal’s health. Check CRM notes and fields to see which MEDDIC elements are well-defined and which are missing or weak (e.g., no clear champion or undefined metrics for ROI). Summarize the status: for each MEDDIC element, note if it's fulfilled or a gap (for example, "Champion: not identified – risk"). For any gaps, recommend a specific action for the rep ("Identify a champion by engaging a power user at the client", etc.). Provide this as a short analysis to discuss in the deal review, without including any confidential customer names or details.

100% MEDDIC criteria covered for key deals (no critical gaps before close)

Blind Spot: A fully filled MEDDIC checklist doesn’t guarantee a win; qualitative factors matter. Use MEDDIC as a guide, but also consider relationship strength and timing.

You are a sales manager nearing quarter-end and need a focused closing strategy to ensure the forecast is met. Draft a 'closing gameplan' outlining critical actions for the final <TIME_PERIOD> (e.g., 2 weeks). Include steps like: daily deal stand-up calls for all closing opportunities, executive sponsor outreach for each big commit deal, expedited approval process for special discounts or terms, and clear assignments for every at-risk deal (who will follow up and by when). Make the plan a list of bullet points with responsible owners (e.g., "<REP_NAME> will update deal <DEAL_NAME> status daily"). Use a rallying tone that instills urgency and teamwork. This plan will be shared with the sales team to drive a coordinated push to hit the number.

All commit deals receive focused attention; ≥95% of commit revenue closes by quarter-end

Blind Spot: End-of-quarter pushes can strain customer relationships (avoid overly aggressive tactics that could cause churn later). Push hard, but don’t sacrifice long-term customer goodwill.

You are a sales manager preparing a brief forecast status update for the executive team mid-quarter. In an email or memo format, concisely report: the current commit vs target (e.g., "$X committed which is 92% of <KPI_TARGET>"), any changes since last update ("commit up by $Y due to deal A pulled in" or "down by $Z after loss of deal B"), and key risks/upside. Highlight if you need any leadership support (e.g., "a pricing exception for a big deal" or "additional marketing to backfill pipeline"). Keep it factual and to the point, aiming for a few bullet points or sentences. This update should ensure leaders are aware of forecast health and any help needed.

Leadership alignment on forecast (no surprises at quarter-end; execs respond timely to any support requests)

Blind Spot: Maintain realism in communication – overconfidence or excessive caveats can both undermine credibility. Provide a clear-eyed view so that executive expectations are properly set.

You are a sales manager and the current forecast shows a potential shortfall against <KPI_TARGET>. Develop a mitigation plan with concrete steps to close the gap. Outline 3 strategies such as: (1) Upsell/Cross-sell push – coordinate with Customer Success to secure additional revenue from existing customers, (2) Accelerate late-stage deals – e.g., offer quarter-end incentives or bring in executives to help close, (3) Pipeline supplement – have BDRs/run a quick campaign to add fast high-quality opportunities. For each action, include who is responsible and the expected impact (e.g., "Upsells by CS team could add $X, closing the gap by Y%"). Present this as a bulleted action plan. The tone should be urgent but positive, conveying that with focused effort the team can still hit the number.

Achieve 100% of <KPI_TARGET> despite initial shortfall (gap closed)

Blind Spot: Avoid last-minute desperation tactics that erode margin or customer trust. The plan should be aggressive but realistic – for example, don’t bank on all stretch deals closing without evidence.

You are analyzing forecast accuracy at the rep and team level. Using data from the last <FORECAST_PERIOD>, find which reps had the biggest gaps between their forecast commit and actual sales. List the top 2 reps who over-forecasted (commit far above actual) and the top 2 who under-forecasted (actuals exceeded their commit). Provide possible reasons (e.g., Rep A over-forecasted due to assuming a deal would close that slipped; Rep B was conservative and sandbagged). Also note any pattern by team (e.g., one manager’s team consistently under-forecasts). Summarize these findings and suggest one coaching action for the most inaccurate forecasters (for instance, training on pipeline qualification or tighter deal inspection).

Improved individual forecast accuracy (each rep’s forecast within ±5–10% of actual)

Note: Discuss forecast accuracy privately with reps; publicizing individual errors can hurt trust. Focus on improvement, not blame.

You are reviewing past forecasts to improve accuracy. Look at the last 2–4 quarters of data: compare each quarter’s committed forecast vs actual results. Identify any consistent bias – for example, "commit was ~10% over actual in Q1 and Q2" (over-forecasting) or the opposite (under-forecasting). Also note if certain teams or managers had larger variances. Summarize 2 insights about these patterns (e.g., a particular manager always sandbags by ~5%, or the team overall tends to be over-optimistic in Q4). Conclude with a suggestion for adjusting the current forecast process (like applying a correction factor or additional scrutiny to historically inaccurate areas).

Quarterly forecast error reduced to <5%

Blind Spot: If market conditions changed recently, past bias may not hold going forward. Use historical trends as a guide, but continuously re-evaluate assumptions.

You are a sales manager analyzing the sales forecast for <FORECAST_PERIOD>. The CRM shows a rep commit total of <COMMIT_TOTAL>, best-case of <BEST_CASE_TOTAL>, and a weighted pipeline forecast of <PIPELINE_FORECAST>. An AI-based model predicts <AI_FORECAST> for the period. Calculate the 'upside' variance between commit and best-case, and note any gap between the human commit and the AI forecast. Identify which deals or teams account for most of the variance (e.g., a big deal in best-case not in commit). Summarize 3 key insights or risks from this comparison (such as over-reliance on a few large upsides or an AI-flagged risk that humans overlooked) and give a confidence assessment for hitting <KPI_TARGET>.

Forecast within 5% of actuals (high accuracy)

Blind Spot: Numbers alone don’t capture everything – consider qualitative factors (e.g., rep optimism, customer sentiment) that the AI or raw data might miss when assessing forecast confidence.

You are a sales manager at a B2B SaaS company preparing a pipeline cleanup request for your team. Many opportunities in CRM appear outdated or have no recent activity, skewing pipeline metrics. Write a professional, concise email to all sales reps asking them to review and update their pipeline in the CRM by end of week. Specify that they should close out deals that are truly dead, update stages for deals that moved, and add next steps for active deals. Emphasize how maintaining accurate pipeline data helps forecasting and coaching (e.g., avoids false sense of security from inactive deals). Use a formal tone and focus on the importance of data hygiene, not blaming anyone.

100% of deals updated in CRM; forecast accuracy improved due to current data

Blind Spot: Avoid negative tone; frame as collective improvement effort. Ensuring buy-in will lead to more thorough updates.

You are a sales manager preparing an outreach to Marketing leadership to address pipeline gaps. Write a brief proposal (email format) outlining the current pipeline shortfall and requesting Marketing support. Include key data (e.g., "coverage is only 2.5x vs 3x goal, missing ~$X in pipeline") and suggest joint actions such as targeted campaigns or extra webinars. Use a cooperative tone and highlight the mutual benefit (hitting revenue goals). End with a clear call-to-action for a meeting or plan confirmation. This communication should motivate Marketing to collaborate on an urgent pipeline generation effort.

Marketing-sales initiative launched (X new opportunities generated within a month)

Note: Frame it as a partnership, not blame – maintain a solutions focus to get Marketing onboard enthusiastically.

You are a sales manager at a B2B SaaS company facing a pipeline shortfall. Pipeline coverage is below 3x, signaling a need for immediate pipeline generation. Draft a plan to align with Marketing and your 3 enablement staff to quickly boost pipeline. Propose 2–3 initiatives (e.g., a targeted lead-gen campaign, an SDR call blitz, customer referral incentives) and detail how you will involve Marketing in each. Prioritize the initiatives by potential pipeline impact and specify support needed (budget, content, events). The tone should be formal and persuasive, as this plan may be shared with the Marketing VP to secure buy-in.

Pipeline coverage restored to ≥3x target after initiatives

Blind Spot: Ensure Marketing has capacity and agreement – an unrealistic demand for leads could backfire. Coordinate closely on feasible targets.

You are a sales manager at a B2B SaaS firm comparing your team’s performance to industry benchmarks. Your team’s win rate is <WIN_RATE>% and average sales cycle is <SALES_CYCLE_LENGTH> days. Industry benchmarks for similar B2B SaaS sales are ~20–30% win rates and ~84 days sales cycle. Using CRM and BI data, summarize where your team outperforms or underperforms these benchmarks. Highlight the two largest gaps (e.g., win rate, cycle time, deal size) and suggest one improvement initiative for each. Provide a concise analysis for the QBR, using only summary statistics (no raw data dumps).

Close gaps to benchmarks (e.g., win rate into 20–30% range)

Blind Spot: Benchmarks are general – differences in market or product can skew direct comparisons. Use benchmarks as guides, not absolute targets.

You are a sales manager at a B2B SaaS company reviewing pipeline velocity. Several opportunities have exceeded the typical <SALES_CYCLE_LENGTH>-day sales cycle without movement. Using CRM data and call-recording insights, identify the top 3 stalled deals at risk of slipping (e.g., no activity in 30+ days, repeated pushouts). For each stalled deal, summarize why it’s stuck (no recent customer contact, missing champion, etc.) and suggest a next step to re-engage or close it out. Provide this as a brief report to address in the pipeline review meeting (no PII, just deal context and recommended actions).

Reduced sales-cycle delays (fewer deals stuck beyond <SALES_CYCLE_LENGTH> days)

Warning: Not all silent deals are lost – confirm context with reps before dropping opportunities.

You are a sales manager at a B2B SaaS company with an 80-person sales org. Your team’s quarterly bookings target is <KPI_TARGET>, and current pipeline coverage is <PIPELINE_COVERAGE>x (below the 3-4x benchmark). The team's win rate is <WIN_RATE>% and average sales-cycle length is <SALES_CYCLE_LENGTH> days. Using CRM pipeline reports and historical win rates, identify the biggest gaps or risks in the pipeline that could jeopardize hitting <KPI_TARGET>.Summarize the top 3 pipeline risk factors and recommend actions to address each, ranked by business impact. Only provide aggregated insights (no raw customer names).

Maintain ≥3x pipeline coverage (no pipeline shortfall)

Blind Spot: High coverage (4x+) can include stagnant deals – focus on pipeline quality, not just quantity.

You are a sales manager coaching a rep on how to win a key late-stage deal <DEAL_NAME>. Formulate a focused action plan using MEDDIC elements as a guide: ensure Metrics (business case ROI) are quantified and shared, engage the Economic Buyer directly (list steps to get a meeting or involve an executive sponsor), confirm Decision Criteria/Process (outline remaining steps or paperwork needed), reinforce the Pain (have the rep reiterate the main pain point our solution solves), and leverage the Champion (if one exists, plan how they will help, or find one if not). Structure the output by these categories, with bullet points under each detailing what the rep should do. The tone should be coaching-oriented and specific (e.g., "Economic Buyer: have <REP_NAME> request a meeting with the CFO by offering to review ROI outcomes"). This plan will be sent to the rep as follow-up to a deal strategy session.

Deal <DEAL_NAME> closed (or advanced significantly) after executing plan

Blind Spot: Even a perfect strategy can fail if the customer’s situation changes (budget cuts, etc.). Prepare the rep to monitor for external changes and have plan B (e.g., fallback to a smaller land deal) if full win becomes unlikely.

You are a sales manager writing a one-page executive summary for a major deal <DEAL_NAME> to brief upper management. Include: a brief customer profile and deal value, the use case or problem we’re solving, current status (stage, close date, next step), and a MEDDIC snapshot (e.g., pain point, champion identified, economic buyer involved or not, any metrics ROI identified). Also clearly state what help or attention is needed from leadership ("Executive Ask: e.g., CEO call to their CEO, approval for bespoke terms"). Keep the summary concise (a few short paragraphs or bullet sections) and free of jargon – assume the CEO/CFO will read this to get up to speed. Focus on the facts and the plan to win. Do not include internal slang or raw notes.

Leadership provides timely support (executive calls, approvals) resulting in accelerated deal closure

Blind Spot: Use executive time wisely. Only escalate what’s truly needed (e.g., a CEO call) for key deals. Over-escalating minor issues can cause leadership to tune out future deal support requests.

You are a sales manager documenting a recent major lost deal to share lessons with the team. Structure the post-mortem using a feedback framework like SBI (Situation-Behavior-Impact). For example: Situation: Describe the deal context (customer profile, needs, our proposal). Behavior/Approach: Describe what we did in the sales process (our strategy/behavior – e.g., we demoed only to lower-level users, or we gave a last-minute discount). Outcome/Impact: State how and why we lost (customer chose competitor offering X features at lower cost, or our champion left, etc.). Insight/Lesson: Finally, explain what we learned and what we’ll do differently (e.g., involve economic buyer earlier, validate budget sooner). Keep it factual and avoid blaming individuals. The output will be a few bullet points or short paragraphs to discuss in the next sales meeting for continuous improvement.

Common loss reasons addressed (e.g., next quarter’s similar deals win rate improves, fewer repeats of the same mistakes)

Blind Spot: Maintain a blameless culture – the goal is to fix process or strategy issues, not to publicly shame the rep. Ensure the takeaway is about what the team can do better collectively.

You are preparing for a weekly 1-on-1 with <REP_NAME>. Using CRM and BI dashboards, compile a performance snapshot: current quota attainment (<REP_NAME> is at % of <KPI_TARGET>), pipeline coverage for upcoming period (e.g., $X pipeline = Y.x coverage of their quota), win rate (<REP_NAME>% vs team average), and activity metrics (calls/meetings – an activity score of <ACTIVITY_SCORE>, compared to benchmark). Note any trends ("conversion from demo to close is low", or "pipeline is strong but mainly early-stage"). Also mention coaching or training engagement ("<REP_NAME> had <COACHING_HOURS> hours of coaching this month"). Summarize 1–2 strengths (e.g., high outreach activity, strong product knowledge) and 1–2 areas for improvement (e.g., needs to improve closing, or pipeline building). This summary will be the basis for your 1:1 discussion, so keep it factual and concise.

Identified issues addressed next period (e.g., rep’s low metric improves: higher win rate or attainment closer to target)

Blind Spot: Metrics provide clues but not the full story – discuss with the rep to uncover any external factors or personal challenges affecting performance. Data + dialogue gives the true picture.

You are reviewing <REP_NAME>'s recent call recordings to identify coaching insights. From the call-recording platform analytics, note patterns: e.g., talk-to-listen ratio, handling of objections, technical knowledge. Identify 2 things <REP_NAME> does well on calls (e.g., explains value clearly, builds rapport) and 2 things to improve (e.g., interrupts customer, misses discovery questions). Use the SBI model for one example: describe the Situation ("on the ACME Corp call yesterday"), the Behavior ("<REP_NAME> did most of the talking during the pricing discussion"), and the Impact ("the customer’s concerns weren’t fully heard, leading to unresolved objections"). Summarize these observations in a brief report, without quoting any sensitive info, to review in the 1:1. Make the tone constructive – highlight strengths too, not just weaknesses.

Higher quality sales conversations (e.g., next call review shows improved behavior; call quality score increases)

Warning: Base feedback on multiple calls to ensure issues are consistent, not one-off. Balance critique with positives to keep the rep motivated to improve.

You are assessing <REP_NAME>'s skill development. Review enablement data on completed courses, certifications, and simulation performance. Note accomplishments: e.g., finished all onboarding modules, passed product demo certification with 85%, simulation-score lift of 10 points after coaching (from 75 to 85). Also note gaps: maybe <REP_NAME> has not completed an optional negotiation workshop, or scored low on a recent role-play. Correlate these with on-job performance if possible ("the rep scored low on negotiation sim, which aligns with struggling to close price-sensitive deals"). Summarize 2 key observations (strength or gap) and recommend 1 targeted development action (like additional practice on a weak area or advanced training) to discuss in the 1:1. Keep it focused on improvement and supported by the data.

Rep’s skill gaps addressed (e.g., simulation scores reach target level; ramp time shorter than average)

Blind Spot: Training metrics are proxies. A high simulation score doesn’t always equal field success, and vice versa. Use this data along with real-world performance feedback for a well-rounded development plan.

You are a sales manager planning a coaching session with <REP_NAME> using the GROW framework. Structure your prompt to the rep (or your notes) in four parts: Goal: Ask or define what performance goal <REP_NAME> wants to achieve (e.g., "reach 120% of quota next quarter" or "improve win rate by 5 points"). Reality: Summarize the current situation factually ("currently at 85% quota, win rate 20% with pipeline coverage 2x – key deal slipped last quarter"), and highlight obstacles or challenges observed. Options: Brainstorm 2-3 options or strategies <REP_NAME> could pursue to bridge the gap ("increase outbound calls by 20%", "schedule weekly deal strategy reviews", "take an advanced demo training"). Way Forward (Will): Conclude with an action plan that <REP_NAME> commits to, including specific steps and timelines ("<REP_NAME> will implement chosen options, with milestones: e.g., 5 extra meetings weekly, and we’ll review progress bi-weekly"). Formulate this as a brief plan or script you’ll follow in the 1:1, ensuring it’s collaborative. The tone should be supportive, and the output clearly delineated by Goal, Reality, Options, Way Forward.

Rep achieves the set Goal or shows measured improvement (success of coaching plan tracked by KPI change)

Blind Spot: The goal must come from the rep too – if it’s imposed or too lofty, GROW plan won’t stick. Use GROW to facilitate the rep’s ownership of their improvement.

You are a sales manager providing feedback to <REP_NAME> about a specific behavior, using the SBI (Situation-Behavior-Impact) model. Draft a feedback statement: Start with the Situation – when/where it occurred (e.g., "In this morning’s team meeting…"). Then the Behavior – describe what <REP_NAME> did or said (e.g., "...you interrupted the client multiple times while they were speaking..."). Then the Impact – explain the result of that behavior (e.g., "...which caused the client to become quiet and the deal discussion stalled."). Next, suggest a collaborative next step to improve ("I appreciate your input; let's discuss your concerns one-on-one and keep client meetings focused on listening first."). Keep the tone calm, professional, and focused on behaviors, not personality. This script will guide you when you deliver the feedback to ensure it's clear and objective.

Behavior improved in subsequent similar situations (e.g., client interactions smoother, no similar complaint)

Blind Spot: Deliver feedback privately and timely; public criticism or delaying too long can reduce its effectiveness. Use SBI to stay objective, but also let <REP_NAME> respond – it should be a dialogue.

You are a sales manager organizing your weekly 1-on-1 with <REP_NAME>. Create a structured agenda outline to ensure a productive conversation: 1) Wins & Updates: Start with positive news (recent deals won, progress since last meeting, personal check-in). 2) Pipeline & Metrics: Review key numbers (current attainment vs <KPI_TARGET>, pipeline health, forecast for <FORECAST_PERIOD>, key deals status). 3) Challenges: Discuss any roadblocks or deals at risk where <REP_NAME> needs help; identify any support needed. 4) Coaching & Development: Follow up on skill improvements or training (e.g., progress on last coaching plan, any practice needed). 5) Action Commitments: Conclude with 2-3 agreed actions for the next week (specific tasks or targets <REP_NAME> will focus on, and any support you'll provide). Present this agenda as bullet points or a numbered list that you can fill in during the meeting. The tone should be supportive and structured, ensuring it's clear this is a collaborative discussion.

Consistent, focused 1:1s (all key topics covered; actions from prior meeting completed by next meeting)

Blind Spot: Don’t let the agenda become a rigid checklist – remain flexible if <REP_NAME> has pressing topics. Ensure the rep’s concerns are heard even if they don’t fit the template exactly; the agenda is a guide, not a script.

You are preparing data for the weekly pipeline review meeting. Gather key changes since last week: How many new opportunities were added and total their value, how many deals were closed won or lost (and value), and any big shifts (e.g., a deal moved from Pipeline to Commit or slipped to next quarter). For example: "New: 5 opps added ($300k); Closed Won: 2 deals ($150k); Closed Lost: 1 deal ($50k, lost to competitor); Moved: Deal <DEAL_NAME> slipped to Q+1 ($100k)". Provide a succinct summary of these pipeline movements in bullet form to share at the meeting. Focus only on significant changes that impact forecasts or strategy. No raw CRM dump, just the high-level numbers and notable examples.

Team awareness of pipeline delta (no significant change goes undiscussed; pipeline accuracy improves week to week)

Blind Spot: Highlight quality, not just quantity – a flood of new opps means little if they’re unqualified. Ensure the team notes not just counts but the significance (e.g., lost deals reasons) behind the changes.

You are reviewing the pipeline before the team call to flag stalled deals. Identify any significant opportunities that have not advanced in over <STAGNANT_DAYS> days. List 3 such deals (with their owner and value, but anonymize customer) and note how long they've been stagnant and possible reason from CRM notes ("awaiting legal review", "client unresponsive", etc.). For each, suggest a question or next step to bring up in the meeting (e.g., "Deal <DEAL_NAME> – 45 days in Stage 3; ask rep if customer decision maker engagement is lacking, plan a strategy to re-engage"). This ensures the pipeline review addresses potential bottlenecks. Keep it brief and factual.

Aged deals addressed (either progressed or removed; average pipeline age reduced)

Blind Spot: A deal might appear stalled but could have progress not logged in CRM. In the meeting, ask the rep for the latest context rather than assuming inactivity means neglect.

You are compiling a list of the top opportunities for the pipeline review meeting so the team can focus on what matters most. Identify the five largest deals in the pipeline and note their stage and expected close date (e.g., "$200k deal in Proposal stage closing <FORECAST_PERIOD>"). Also flag any that are in Commit. Provide a one-liner status for each (e.g., "Awaiting security review" or "Verbal confirmation received"). This will be shared so everyone is aware of the big bets and can offer help or insights if needed. Keep the description concise and omit any sensitive details. The goal is to ensure these big deals get appropriate attention in the discussion.

No major deal is overlooked in meetings (all top 5 deals discussed until closed or resolved)

Blind Spot: It’s easy to focus only on big deals – ensure smaller but numerous deals aren’t entirely ignored (their aggregate impact matters). However, for meeting efficiency, highlighting top deals is useful; just balance it with overall pipeline health in other forums.

You are creating an agenda for the weekly pipeline review meeting with your team (and possibly your VP). The meeting is 30 minutes. Outline it as: 1) Pipeline Metrics Update (5 min): You share highlights of new/lost deals and pipeline coverage vs target. 2) Key Deals Discussion (15 min): Each rep or manager covers their top deals or any stuck deals (prioritize the flagged ones from analysis). 3) Blockers & Needs (5 min): Open floor for reps to mention any help needed (e.g., pricing approvals, resource allocation). 4) Action Recap (5 min): Summarize agreed next steps for specific deals or pipeline generation efforts. Add time allocations for each section (~30 min total). Present the agenda as bullet points with times. Maintain a brisk, data-driven tone. This agenda ensures the call stays focused on numbers and actions.

Efficient meeting (stays ~30 min, covers all sections) and all pipeline risks addressed (no critical deal goes unmentioned)

Blind Spot: While sticking to the agenda is important, allow flexibility if a critical issue emerges. Don’t cut off important deal discussions just to stick to schedule – use judgment if deeper discussion on a key deal is needed.

You are a sales manager following up on the weekly pipeline call with an email to the team. In the email, thank everyone for their input and concisely list: – Decisions/Highlights: E.g., "Deal X will be escalated for executive support; focus this week on prospecting to fill Q4 pipeline." – Action Items & Owners: E.g., "<REP_NAME> to update deal Y by Wednesday with new close date; <MANAGER_NAME> to secure pricing approval for deal Z." – Wins/Praise: Mention any quick wins or good updates from the meeting ("Congrats to <REP_NAME> for closing ABC deal!"). Ensure the tone is positive and clear. Use bullet points for actions so it’s easy to scan. This email serves as documentation so the team is accountable to the discussed actions.

100% of action items completed by next meeting (each owner addresses their tasks)

Note: Keep the tone positive and factual. The follow-up shouldn’t be a reproach list; it’s a reference so nothing falls through cracks. Send it promptly (same day) for best effect.

You are preparing brief pipeline scorecards for each rep to review at the meeting. For each <REP_NAME>, list: their current pipeline $ (and coverage vs their quota target, e.g., 3.2x), number of opps in late stage (e.g., 3 in negotiation), their biggest open deal and its status (e.g., "$50k deal with XYZ Corp at proposal stage, expected closing <FORECAST_PERIOD>"), and any notable risk (e.g., pipeline heavily reliant on one big deal). Present this information as a list of bullet points per rep (you can use the rep name as a sub-header). Ensure it’s formatted clearly so we can quickly scan each rep’s status during the meeting. Avoid internal jargon or unnecessary detail; focus on metrics and key highlights. This is for internal use in the meeting slide or notes.

Balanced pipeline hygiene improved (e.g., no rep below 2x coverage after assistance; stagnant single-deal reliance addressed)

Blind Spot: Scorecards are a snapshot; a low pipeline rep might have unlogged deals or future commits. Use this visibility to offer help rather than to shame. The aim is to allocate support and spotlight where to drill in, not to rank reps publicly.

You are preparing the forecast roll-up for the weekly forecast call. Compile each team’s numbers: e.g., Team 1 (Manager A) commit $X (Y% of team quota), best-case $X2; Team 2 (Manager B) commit $..., etc. Also sum the overall commit vs the overall target (<KPI_TARGET>) and calculate pipeline coverage for the company (e.g., total pipeline is Zx coverage of remaining target). Highlight any notable changes or outliers ("Team A increased commit by $N after deal ABC advanced; Team B is only at 80% of quota in commit, risk of shortfall"). Provide this as a short summary, maybe a mini-table or list by team with commit, best-case, and variance to goal. It will be shared at the call to quickly show where the organization stands and which teams might need focus.

Accurate forecast roll-up (leadership trusts each team’s numbers; forecast coverage known for all teams)

Blind Spot: Different managers have different forecasting styles (one’s 90% may be another’s 110%). When consolidating, annotate with context if a manager is known to be conservative or aggressive, so leadership interprets correctly.

You are analyzing why the overall forecast changed since last week. Identify the specific deals that caused a significant shift: for example, a large deal added to commit ("Deal <DEAL_NAME> +$200k commit"), a deal pushed out or lost ("Deal XYZ -$150k removed"). List 3-5 such changes with a brief reason if available ("pushed to Q+1 due to customer delay"). This will be used on the forecast call to explain variance: e.g., "Forecast down $100k mainly because Deal ABC moved out". Keep it brief and focused on the big drivers of change, not every minor tweak.

All material forecast changes accounted for (leadership hears reasons behind any forecast delta each week)

Warning: Always verify with the deal owners before the call that these changes and reasons are up-to-date. You don’t want to present stale or incorrect info (e.g., if a "lost" deal came back in last minute).

You are scrutinizing the quality of the commit list for the upcoming call. Identify which committed deals are at risk of not closing in <FORECAST_PERIOD>. Criteria: deals in commit with close date in the quarter that have had no recent activity in the CRM (e.g., no meeting in 14+ days), or where the customer has expressed uncertainties on calls. List 3 commit deals that fit these risk signals, with a brief note on why each is risky (e.g., "Deal <DEAL_NAME>: last contact was 3 weeks ago; decision maker on leave"). Also note the potential impact if it slips ("if slips, team falls to 85% of quota"). This info will be used to discuss risk mitigation in the call. Keep it succinct and based on data (no speculation beyond the evidence).

No unchecked blind spots in commit; high-risk deals get attention or pulled from commit if needed (improving forecast accuracy)

Blind Spot: Reps might not log every customer interaction; a deal could seem inactive but actually isn't. Cross-check with the rep outside CRM data to confirm risk.

You are planning the agenda for the sales forecast call. Structure it as follows: 1) Team-by-Team Forecast Update: (10 min) – Each FLM quickly states their commit vs target and highlights any changes or big moves since last week. 2) Risk & Upside Discussion: (10 min) – Discuss deals at risk in commit (from risk review) and any upside deals that could still close. Ensure each manager addresses how they will cover any gaps. 3) Commit Roll-up & Confidence: (5 min) – You recap the consolidated commit vs <KPI_TARGET>, best-case, and any adjustments (include AI forecast if used) and state your confidence level for <FORECAST_PERIOD>. 4) Action Items: (5 min) – Note any follow-ups (e.g., reforecast a deal, get exec support on a risk deal, adjust pipeline generation plans). Keep it ~30 minutes total. Present the agenda as bullet points with timings. Maintain a brisk, data-driven tone. This agenda ensures the call stays focused on numbers and accountability.

Forecast call stays on track and yields clear decisions; forecast accuracy improves due to proactive discussion (smaller misses)

Blind Spot: Avoid spending too long on pipeline issues in a forecast call – that’s for pipeline meetings. Conversely, ensure people do speak up about risks, not just recite numbers. Balance efficiency with open communication about concerns.

You are about to finalize the forecast after hearing updates. Based on current data, you suspect some adjustments are needed to the commit numbers. Formulate a set of recommendations for the team, such as: – Increasing commit if pipeline and best-case support it (e.g., "Team A, consider moving Deal X into commit given verbal yes"). – Decreasing commit if a committed deal looks shaky (e.g., "Team B, reduce commit by $Y where Deal Z is stalled, move to best-case"). – Focusing on certain upsides (e.g., "Team C, push to close that big upside deal to cover Team B's gap"). Structure these as 3-4 bullet points by team or overall. Frame each as a suggestion to ensure we meet <KPI_TARGET> while maintaining credibility. The tone should be collaborative (we're calibrating forecast together, not dictating). This will be delivered in the call to guide managers in refining their forecasts.

Refined forecast aligns with reality (commit updated to a credible number, reducing variance at quarter-end)

Blind Spot: Over-adjusting can demoralize (if commit drastically cut) or create false pressure (if inflated). Balance optimism with realism; maintain trust by aligning forecast with evidence.

You are a sales manager who just concluded the forecast call and need to share the outcome. Draft a brief update (could be an email to the CRO or a Slack message to the team) summarizing any changes and key decisions: – Revised commit total for <FORECAST_PERIOD> (if changed) and how it compares to target (e.g., "Commit is now $X, which is 97% of target"). – Notable shifts (e.g., "Moved two deals out of commit to best-case due to delays; one upside deal moved into commit after verbal approval."). – Any actions agreed ("We will focus on closing the upside deal from ABC Co. and closely monitor the two risk deals."). – Assurance or ask: (e.g., "We remain on track to hit at least 95% of quota, with upside if we land the big deal. No additional support needed at this time."). Keep it concise and factual. This communicates to leadership the updated state and gives the team a written record of what was decided.

Alignment with leadership on new commit; no confusion among team on forecast status. (Measured by leadership feedback or lack of further queries.)

Blind Spot: Ensure the numbers in the update are absolutely accurate and match what was said; any inconsistency can erode trust. Also, tailor detail to audience: execs want headline and confidence level, team needs to know tasks and any target changes.

You are compiling the quarter’s results for the QBR. Summarize: total bookings achieved vs target (e.g., "$X on a $Y target, attainment = %"); breakdown of new business vs expansion ("$A new, $B expansion, with $C churn, net = $D, so net retention = E%"); and key sales KPIs like win rate (<WIN_RATE>%, up/down from last quarter) and average sales cycle (<SALES_CYCLE_LENGTH> days). Note any noteworthy variance: e.g., "Q3 came in at 95% of target due to two large deals slipping to Q4" or "exceeded target by 10%, driven by an increase in average deal size". Keep it high-level, a few bullets or sentences that capture the core outcome and a bit of context. This will serve as the opening summary slide of the QBR.

Executives grasp quarterly results at a glance (attainment %, net retention, etc.) with context

Blind Spot: If one-off events skewed results (a one-time mega-deal or unusual churn), mention it. Pure numbers can mislead without context (e.g., hitting quota because one huge deal masks broad underperformance).

You are analyzing what drove the quarter’s performance for the QBR discussion. Look at underlying metrics: pipeline generated during the quarter (was it higher or lower than previous quarters?), conversion rates through the funnel (lead to opp, opp to win compared to prior period), average deal size and sales-cycle changes, and percentage of reps hitting quota (attainment distribution). Identify 2-3 important trends: e.g., "Win rate improved from 22% to 25% due to better qualification, but average sales cycle lengthened by 10 days, possibly due to more enterprise deals in mix"; or "Pipeline inflow dropped 15% QoQ, which may challenge future growth". Summarize each trend and its impact in a bullet. These insights will feed the QBR narrative about what went well and what needs improvement.

Leadership understands key performance drivers (e.g., realizes win rate up but pipeline down) and makes decisions accordingly

Blind Spot: Some trends might be due to external factors (market conditions) rather than team execution; differentiate if possible to avoid misguided strategy changes.

You are reviewing individual and team performances to highlight in the QBR. Determine: which sales teams (or regions) performed best vs target (e.g., Team East at 105% quota) and which lagged (Team West at 85%). Also identify top 3 reps (by attainment %) and bottom 3 reps. Note any context ("Top rep <REP_NAME> at 130% – closed two big deals; Lowest <REP_NAME2> at 50% – ramping new hire"). Include any noteworthy HR items: new hires ramping well or not, any high performers promoted, etc. Summarize these as bullet points (no more than 5-6 bullets total). This will highlight talent and capacity topics in the QBR. Keep it factual and avoid personal judgments beyond performance data and simple context.

Key talent insights shared (top performers recognized, underperformers identified for support) – measured by actions (promotions, PIPs) following QBR as needed

Blind Spot: Be sensitive when presenting individual performance in a broad forum; maintain respect and confidentiality where needed. Focus on patterns or team-level outcomes, and frame underperformance in terms of coaching or resource needs rather than blame.

You are organizing the QBR deck for the sales org. Lay out the main sections of the QBR presentation: 1. Results Overview: Key metrics (attainment, growth vs last year, etc.) and whether the quarter goal was met. 2. Wins & Losses: Highlight major wins (big deals, new logos) and discuss significant losses or churn, with reasons. 3. Performance Analysis: Trends and insights (e.g., pipeline coverage, conversion rates, product mix, regional performance, as identified in analysis). 4. Team Highlights: Recognize top performers, address talent or capacity issues (hiring/ramp, any org changes). 5. Challenges & Lessons: What didn’t go well (missed opportunities, competitive pressures, etc.) and lessons learned. 6. Next Quarter Plan: Key initiatives and focus areas for the coming quarter (sales strategy changes, enablement focus, pipeline generation plans). Provide this outline as bullet points. This ensures the QBR covers past performance and forward-looking plans logically.

Comprehensive QBR delivered (all key topics covered within allotted time) and executives have clear visibility into past results and future actions

Blind Spot: Don’t let the presentation be all retrospective; ensure enough time on forward plan (execs care about how you’ll fix issues, not just that they happened). Keep the storytelling clear – from what happened to what’s next.

You are preparing the section of the QBR on next quarter’s plan. List 3 high-impact initiatives you propose to drive improvement or growth. For each, include a title and a brief description with expected outcome: e.g., "Upskill Sales Team on MEDDIC": Launch a training program to deepen MEDDIC usage in deal qualification (expectation: higher win rates, faster deal cycles). "Pipeline Generation Sprint": 4-week focused campaign with Marketing/BDRs targeting key verticals to add $X pipeline (aim: enter next quarter with 4x coverage). "Account Expansion Program": Align with Customer Success on upsell campaigns for top 20 customers (goal: +$Y in expansion ARR, improves net retention). Use bold headers for initiative names. These show leadership you have a forward plan tied to metrics (pipeline, win rate, retention). Ensure each addresses a gap from this quarter.

Initiatives approved and resourced by leadership (success measured by their impact: e.g., pipeline +20%, win rate +5% next quarter)

Blind Spot: Limit to a critical few – too many initiatives can dilute focus. Also tie them clearly to data from this quarter (if win rate dropped, a training initiative makes sense, etc.) so execs see you attacking the right problems.

You are a sales leader drafting the executive summary narrative for the QBR report. This should be a brief introduction (1–2 paragraphs) to the quarter for the executive audience. Include: overall achievement ("Q3 reached 95% of quota, delivering $X of $Y target"), key drivers ("enterprise wins were strong in North America, but APAC performance lagged"), and any macro factors ("longer decision cycles in the market impacted timing"). Acknowledge challenges ("we saw higher churn in SMB, affecting net retention") but also positive outcomes ("we added 3 Fortune 500 clients, bolstering our enterprise foothold"). Conclude with a forward-looking statement ("To address gaps, we’re launching an upsell initiative and ramping new SDRs for pipeline; we remain confident heading into Q4"). Maintain a formal, confident tone with a balance of realism and optimism. This summary will set the stage for the detailed QBR discussion.

Execs have a clear, concise narrative of sales performance (acknowledges challenges, highlights successes) – evidenced by informed and focused QBR discussion

Blind Spot: Don’t sugarcoat issues – executives appreciate transparency. Likewise, avoid a doom-and-gloom tone – show that you understand the issues and have a plan. The summary should inspire confidence that the sales org is under control and continuously improving.

You are preparing the monthly sales summary. Pull key metrics: total bookings for the month vs goal (e.g., "$X on a $Y goal, attainment = Z%"), how much came from new vs existing ("$A from new sales, $B from expansions; $C in churn/downsell, so net = $D"), and notable deals ("Closed BigCo $1M new deal; Lost XYZ Corp $200k renewal"). Also note pipeline added this month ("$P in new pipeline created, now total $Q pipeline for the quarter"). Summarize these in a few bullets or sentences for the executive report. For example: "Bookings: $X (Y% of monthly target)"; "Notable Wins: ABC Corp $M (multi-year deal)"; "Churn: $N lost (two major client downgrades)"). Keep it concise and factual – a quick health check for leadership.

Monthly summary delivered with 100% accuracy (execs trust the numbers and get a quick performance read)

Blind Spot: One month is a small sample; if we had an unusual large deal or miss, mention if it’s expected to normalize or if corrective action is planned. Prevent execs from overreacting to a one-month anomaly by giving context.

You are analyzing the month’s data for any early warning signs to raise to leadership. Consider: pipeline coverage for the quarter after this month (is it sufficient? e.g., only 2.5x with two months left, below 3x ideal), changes in lead volume or conversion rates (downtrend could foreshadow trouble), rep performance distribution (if only 20% of reps hit monthly quota, that’s a concern), or external factors (e.g., unusually high prospect no-response rate). Identify 2 such signals or bright spots, with brief context: e.g., "Pipeline Coverage Alert: Q4 pipeline is only 2.8x quota (below benchmark), indicating risk – need pipeline boost now"; or "Upside: Average deal size grew 15% MoM, which could offset lower deal count." Keep it brief. These will be included in the exec update to prompt discussion or action.

No surprises at quarter-end – issues identified early (e.g., pipeline shortfall addressed in time). Measured by timely mitigation (if pipeline was low, additional campaigns launched, etc.).

Warning: Flag only truly significant deviations; don’t raise alarm on normal fluctuations. Executives should trust that when you highlight a "red flag", it merits attention. Too many minor warnings can cause alert fatigue and diminish credibility.

You are adding color to the monthly executive report with a key highlight and challenge. From the month’s outcomes, pick one major positive (e.g., "closed our largest deal of the year" or "record pipeline added") and one noteworthy challenge ("missed the monthly target by 15%" or "higher churn than expected"). Write each as a bullet point with brief detail: e.g., "Highlight: Won a $2M deal with XYZ Inc (biggest new logo this year), reflecting strong enterprise traction."; "Challenge: Monthly bookings were 85% of goal – a slip largely due to 2 big deals moving out, prompting renewed focus on closing gaps next month." This provides executives a narrative insight beyond the raw numbers.

Executives have a balanced view (successes and issues) – measured by informed questions/focus (they acknowledge the win and are already aware of the challenge from the report, not surprised)

Blind Spot: For the challenge, note what’s being done about it if possible (e.g., "deals moved out are slated to close early next month"). Executives want to know we’re on top of challenges. For the highlight, ensure it’s attributable to replicable effort (not just luck) to reinforce good behavior.

You are writing the monthly sales performance email for the executive team. Compose a brief email that includes: a one-line summary of the month ("October finished at 95% of target, with strong new biz but a uptick in churn"), a few key numbers (bookings $X vs $Y goal, expansion $A vs churn $B, pipeline coverage heading into next month), one highlight (e.g., a big win or achievement) and one concern (e.g., a metric that dipped or a headwind), and a forward-looking statement ("We’re focusing on converting our increased pipeline next month and addressing the support backlog that contributed to churn"). Keep it to 2 short paragraphs or a handful of bullets. The tone is informative and upbeat-but-honest. This ensures busy execs grasp the essentials quickly each month.

Executives are well-informed from the email alone (few follow-up questions needed). Consistency between email and detailed reports builds trust in the data.

Blind Spot: Keep it concise – execs may read on mobile. Avoid jargon or excessive detail; they should get the gist in seconds. And ensure alignment: the figures and statements here must match the formal report/dashboard to prevent confusion.

You are adding explanatory notes to the monthly sales BI dashboard that leadership accesses. For each major metric or chart, write a one-liner insight to give context: e.g., Bookings: "Reached $X, 95% of goal – short by $Y due to two deals slipping to next quarter." Pipeline: "$Z total for Q4 (3.0x coverage) – slightly below ideal, but large deal ABC (not yet in commit) could boost it." Churn: "$C churn this month (above normal); primarily one enterprise cancellation – CS team engaging early with similar accounts." Forecast: "Q4 forecast at $F (90% of target) after adjusting commit; upside of ~$U remains, focusing on closing those." Use concise sentences. The idea is that any exec glancing at the dashboard sees not just numbers but also the story behind them.

Executives correctly interpret dashboard data (no misreading of metrics). Indicated by fewer clarification questions in meetings.

Blind Spot: Update comments with the latest data – stale commentary can mislead. And don’t state the obvious from the chart; add value (explain why a metric is high/low or what’s being done). This will ensure the commentary is actually read and useful.

You are updating the quarter’s sales forecast after this month and notifying leadership of any help needed. Draft a short memo or email: begin with the revised forecast vs target ("After October, we are forecasting $X for Q4, which is ~95% of the $Y target"). Note key changes ("Forecast down slightly from 98% due to one slip, but we added pipeline in other areas"). State confidence and risks ("Commit remains strong at 90% of target; hitting 100% depends on closing two large upsides – high confidence in one, the other is a toss-up"). If you need leadership support, specify it ("May need pricing approval flexibility on Deal ABC; will flag if so" or "An intro to CIO of XYZ Corp from our Board could help their upsell"). End with next steps ("We’ll update again mid-month; currently focusing on closing the big upsides and generating last-minute pipeline"). Keep it factual and no longer than a few short paragraphs.

Leadership alignment on quarter outlook and resource needs (e.g., CFO/CEO aware of likely outcome ±5% and steps being taken). Help is provided where requested, improving win probability.

Blind Spot: If asking for help, be specific and justified – vague appeals ("we need more support") won’t get traction. Conversely, if confident and no help needed, express that clearly to build trust. Continuously update if things change; nothing worse than an outdated projection lingering in an exec’s mind.

You want to see how <REP_NAME>'s ramp progress stacks up. Compare their performance to team or industry averages: e.g., average new AE reaches ~50% quota by month 2 and full quota by 5 months. Check if <REP_NAME> is ahead or behind that curve ("<REP_NAME> is at 45% of quota in month 2 vs team avg 50% – slightly below, but within range"). Also compare activity: if on average new reps make 100 calls in first month, did they? Mention any qualitative difference (maybe <REP_NAME> had a tougher territory than past hires). Summarize in 1-2 bullets whether their ramp is on track relative to expectations or if intervention is needed. This will guide whether to adjust targets or give extra support.

Fair assessment of ramp – if behind benchmarks, triggers support (leading to eventual catch-up); if ahead, identifies best practices to share

Blind Spot: Every rep ramps differently; benchmarks are guidelines. Use them to detect outliers, but don’t label someone a failure at day 60 if, say, enterprise ramps normally take longer. Calibrate expectations to role complexity.

You are auditing how <REP_NAME> has engaged with onboarding resources. Review logs: training modules completed (e.g., 8 of 10 modules done, skipped the optional "Negotiation Deep Dive"), hours of coaching or mentoring received (e.g., 5 coaching hours logged vs recommended 8 by this point), and simulation or quiz results (e.g., scored 78% on product demo simulation, improved from 65% initial – <SIMULATION_SCORE_LIFT> point lift after practice). Summarize any gaps or over-and-above efforts (perhaps they did extra things, or missed some assignments). Conclude if their engagement level is adequate for ramp or if more is needed (e.g., "needs to complete remaining modules and get more call coaching"). This insight will help enablement tailor additional support. Provide 1-2 factual bullet points.

New hire completes all enablement milestones on time (e.g., 100% training done by 90 days; achieves certification scores as required)

Blind Spot: Not all learning is captured in systems. If <REP_NAME> is learning via informal means (peer shadowing, self-study) that isn’t logged, the data might understate their effort. Supplement with your observations of their proficiency before concluding a lack of engagement.

You are updating <REP_NAME>'s 30-60-90 day plan now that they are ~60 days in. Outline next steps in 30-day increments: Day 60-90: focus areas for the coming month (e.g., "independently run full sales cycle for at least 2 opportunities," "increase outbound prospecting by 20%" and "complete advanced product training"). Day 90-120: goals as they approach full ramp (e.g., "close first $100k deal," "achieve first 100% quota month," "obtain MEDDIC certification"). Day 120-150: high-level goals for post-ramp (e.g., "sustain 100%+ monthly attainment," "mentor a newer rep by then"). Make these bullet points under each timeline. Ensure goals are specific and attainable based on current progress (if they are behind, include remedial actions; if ahead, add stretch goals). The tone should be encouraging and clear. This plan will be reviewed with the rep to align on next steps to full productivity.

Rep meets ramp plan milestones (e.g., hits targets by 90 and 120 days). If off-track, issues identified and addressed promptly within this plan period.

Blind Spot: Use the plan flexibly – it’s a guide, not a contract. If <REP_NAME> hits 90-day goals early or struggles, adjust in real time. The purpose is to support, not to be an arbitrary checklist.

You want to help <REP_NAME> practice a critical sales scenario in a role-play. Identify an area the rep needs work (e.g., handling pricing objections or doing discovery). Generate a realistic scenario for that: Situation: set the scene (e.g., "Mid-market prospect CFO, concerned about cost"). Customer Prompt: what the customer might say (e.g., "Your product looks good but your price is 20% higher than our other quote…"). Rep’s Objective: what <REP_NAME> should achieve (e.g., overcome the price objection by reinforcing value). Provide at least 2-3 customer utterances/questions in script form for the rep to respond to. For example, "Customer: We’re not sure the ROI justifies that cost." The role-play will be <REP_NAME> responding to such statements. Keep the scenario challenging but fair, reflecting common objections. This will be used in a coaching session.

Observed improvement in target skill (e.g., next real customer call, <REP_NAME> handles similar objection smoothly; higher confidence in that area)

Blind Spot: Ensure role-play scenarios mirror actual sales situations the rep faces. An irrelevant or overly contrived scenario won’t yield improvement. After the role-play, debrief thoroughly to connect the practice to real deals.

You are drafting a message to <REP_NAME> to solicit their feedback on the onboarding process now that they're two months in. Write an email that: thanks them for their hard work so far and acknowledges specific progress (e.g., finishing training, first deal closed), then asks for candid feedback on the onboarding/training: what was most helpful, and where they felt unprepared or need more support. Possibly give examples to prompt them (e.g., "Was the product training sufficient? Could shadowing have started earlier?"). Assure them their feedback is valued and will improve the process for the next hires. Invite them to share openly via reply or a meeting. Keep the tone appreciative and open. Emphasize that the goal is to make onboarding better, not to evaluate them.

Constructive feedback collected and applied (onboarding improvements implemented; next new hire class reports higher satisfaction)

Blind Spot: New hires may be hesitant to criticize. Emphasize you want honesty and that it won’t reflect on them. You might even offer an anonymous form if they prefer. Ensure you actually act on good feedback – that will encourage future openness.

You are investigating why <REP_NAME> is underperforming (e.g., only % of quota). Analyze key metrics: pipeline coverage (does <REP_NAME> consistently have less than 3x pipeline?), win rate (compare <REP_NAME>% vs team average), average deal size (smaller deals than peers could mean going after low-value opps), and activity (calls/meetings vs target). Also check qualitative factors: any notes about territory issues or personal circumstances. Compile 2-3 likely factors with evidence: e.g., "Pipeline insufficient: averaged 2x coverage, below 3x norm, leading to shortfall"; "Low conversion: win rate 15% vs team 25%, indicating skill gap in later stages". This diagnosis will inform the improvement plan. Provide it objectively, using data from CRM/BI without personal bias.

Root causes identified (agreed by manager & rep), leading to targeted actions. Improvement seen in specific metrics (e.g., pipeline coverage or win rate) the following quarter.

Blind Spot: Data might not tell the whole story – for instance, if pipeline is low, is it due to low effort or external factors like few leads? Pair this analysis with a conversation with <REP_NAME> to validate and uncover anything numbers miss.

You pull <REP_NAME>'s performance history to see if underperformance is a new issue or a pattern. Look at the last 4 quarters (or applicable periods): note quota attainment each quarter and any variability. For instance, "Q1 95%, Q2 88%, Q3 70% (downtrend)" or "was consistently ~100% until this quarter dropped to 60%". Also check how they did relative to team average each quarter. See if they've been on a PIP or received prior warnings. Summarize the trend: e.g., "<REP_NAME> maintained ~90-100% for first half of year, but has declined 3 quarters straight" or "This is <REP_NAME>'s first miss after 4 quarters of meeting targets – an outlier so far". This context will influence whether a formal PIP is initiated or if this is a first-time dip that might be solved with informal coaching. Keep it factual and focused on the numbers.

Appropriate management action taken (if trend shows persistent issue, PIP initiated; if one-time, coaching given). Outcome: either performance rebounds next quarter or managed exit if consistent decline continues.

Warning: Past success doesn't guarantee future; also, a new issue could escalate if ignored. Balance giving benefit of doubt (for a one-time drop) with urgency if a negative trend is clearly forming. Also consider any changes in role or territory that align with the performance drop.

You analyze whether <REP_NAME>'s underperformance might relate to factors beyond their control: territory or quota issues. Examine their territory’s potential vs others (e.g., did they get fewer leads or a harder segment?), any major customer changes (loss of a big account impacting their renewals), and quota fairness (was their quota significantly higher relative to historical sales in that patch?). For example: "<REP_NAME>'s territory generated 20% fewer opportunities than team average this year" or "They had two large customers churn (outside rep’s control) which cost them $X in renewals." Summarize 1-2 findings if applicable. This will inform whether we adjust expectations or provide additional support (like marketing help) for this rep. Keep it analytical.

Fair performance evaluation – if structural issues found, adjustments made (quota relief or territory realignment), leading to equitable expectations. If none, focus remains on rep’s execution issues.

Blind Spot: It’s easy for reps to blame territory/quotas. Scrutinize with data but remain open – if multiple reps in similar territories are lagging, structural issues could be real. Address those to maintain morale. Conversely, if data shows territory is fine, you have a stronger case to focus on the rep’s skills/effort.

You are preparing for a meeting with about their poor performance. Outline key talking points: – Opening: State the purpose of the discussion and express concern ("I want to discuss your sales results this quarter; you’re at 55% of quota, which is significantly below expectation"). – Facts/Behavior: Use data or specific examples (SBI-style: "In Q3 (Situation), you missed quota by 45% (Behavior), which impacts team results and raises concern about fit in role (Impact)"). – Rep’s Input: Ask for their perspective ("Help me understand what you think happened. Are there obstacles or support you need?"). – Expectations: Reiterate the performance standard ("We need quota attainment to be at least 90%."). – Plan: Introduce the improvement plan/PIP ("I’ve outlined a 60-day improvement plan with clear goals and support – I want to review that with you"). – Support: Emphasize it’s a joint effort ("The company will invest in helping you – coaching, leads – but we need to see commitment and results from your side"). – Consequences: Be clear about implications ("If we don’t see sufficient improvement, we may have to consider further action, including exit"). – Close: End positively ("I believe you can turn this around, and I’m here to help you succeed. Let’s work together on this."). Use respectful, firm language. This outline ensures you cover all bases.

Clarity and agreement on performance issues and path forward (rep understands seriousness but feels supported). Documented conversation for HR. Ideally, performance improves post-discussion (or next steps are uncontested if not).

Blind Spot: Remain calm and empathetic – the goal is to improve, not to scold. Give a chance to respond during the talk; listen for legitimate issues (e.g., personal problems, territory concerns) that might be addressable. Also, stick to facts to avoid any perception of unfairness or personal bias (especially important if things progress to termination).

You are examining the pipeline of expansion (upsell/cross-sell) deals for existing customers. Note the total expansion pipeline for this quarter (e.g., "$5M in expansion opps") and how that compares to the expansion goal or last quarter ("on track for 110% of expansion target" or "at 70% of plan, lagging"). Identify the top 2 expansion opportunities (by value) and their stages (e.g., "Upgrade of XYZ Corp $1M – Proposal stage, closing likely Q4; Cross-sell to ABC Inc $500k – early stage"). Also note if expansions are concentrated (e.g., one big deal makes up 50% of expansion pipeline – risk) or broadly distributed. Summarize in a couple of bullets the health of the expansion funnel and any focus areas (like a huge upsell we must land). This will help manage revenue growth from the customer base.

Expansion target attainment % achieved (e.g., meet or exceed expansion quota). Also improved net retention if expansion pipeline converts successfully.

Blind Spot: Expansion deals can be optimistic if identified by CSMs without full sales vetting. Treat them with the same scrutiny as new deals in forecast calls. Also, ensure chasing expansions doesn’t detract from core renewal management – expansions should enhance, not jeopardize, the renewal.

In addition to the formal PIP, you want to actively support and monitor day-to-day. Outline a plan: Frequent Check-ins: e.g., schedule a 15-minute standup each morning or every other day to review 's plan for the day and priorities. Ongoing Coaching: e.g., you or an enablement coach will shadow one call per week and give feedback immediately. Peer Mentor: Assign a top-performing peer as a buddy can go to with questions or to role-play pitches once a week. Recognition of Progress: If hits a short-term goal (like 5 new opportunities added in a week), acknowledge it in the next team meeting to boost confidence. Mid-point Review: At PIP midpoint, have a formal sit-down to evaluate progress and adjust tactics if needed. List these steps as bullets. The tone is proactive and supportive – showing that the company is investing in their success during this period.

Rep engagement and morale remain high enough to drive improvement (rep actively participates in check-ins, completes actions; no disengagement). If improvement occurs, rep feels supported and builds confidence.

Blind Spot: Some reps might feel micro-managed by intensive monitoring. Frame check-ins as collaborative, not policing. Also ensure you don’t neglect other team members by focusing only on one rep – use enablement or mentors to distribute support. Ultimately, the rep has to own their improvement, but visible management commitment can make a difference.

You are reviewing customer churn data for the last quarter. Identify how many customers churned and the associated lost revenue (e.g., "5 customers churned, $2M ARR lost"). Summarize the top reasons noted (from CS teams or exit interviews): e.g., 2 cited missing features, 2 had budget cuts, 1 went with a competitor’s cheaper solution. Note any pattern ("3 of the churned were SMB clients on legacy plan" or "all churned customers had low product usage"). Provide this as 2-3 bullet points for the QBR or exec report, focusing on actionable insight (like feature gaps or support issues to address). Keep customer names confidential; just describe segments or commonalities. This will inform churn reduction strategies.

Churn reasons clearly understood (e.g., top 2 reasons account for >80% churn). Improvement actions aligned to reasons (feature fixes, CS outreach) lead to churn rate reduction next quarter.

Blind Spot: Churn feedback from customers may mask real reasons (they might give polite excuses). Combine this analysis with CSM insights and product usage data. Don’t over-index on one quarter’s reasons if your install base is small – look for sustained patterns over time.

You want to present the combined effect of churn and expansion (Net Revenue Retention, NRR). Calculate NRR = (Starting ARR + expansion - churn) / Starting ARR * 100%. E.g., start Q ARR $100M, expansions $5M, churn $3M, NRR = (100 + 5 - 3)/100 = 102%. Note if this meets the target (say 105%) or last year’s NRR. Break down components: expansion added +5%, churn took away -3%. Identify key drivers: "NRR fell short mainly due to two large churns (budget cuts) despite strong upsells in Enterprise" or "NRR improved from 98% to 102% thanks to successful cross-sells offsetting minor losses." Provide a concise summary sentence or two for the execs. This shows how well we are growing existing accounts.

Net retention rate at or above goal (e.g., NRR >100% indicating net growth). If below, causes known and addressed (subsequent NRR trend upward).

Blind Spot: A high NRR can mask churn if driven by a few huge expansions; conversely, a lower NRR might be acceptable if churn was strategic (unprofitable clients). Provide context – e.g., if churn was in low-end customers while expansion was high-end, the quality of revenue improved. Execs will want the story behind NRR, not just the number.

You are collaborating with Customer Success to reduce churn. Draft 3 key initiatives: 1. Early Warning System: Implement a health score dashboard (usage, support tickets, NPS) to flag at-risk customers 2-3 months before renewal, and arrange proactive outreach by CSM/sales for those accounts. 2. Executive Sponsor Program: Assign a sales or exec sponsor to each strategic customer; for any account above $X ARR or flagged by health score, have quarterly executive check-ins to reinforce value and address concerns. 3. Value Reinforcement Campaign: Ensure every customer has a ROI review or success story shared mid-term (e.g., business review meeting) to remind them of achieved value before renewal time; involve product team if missing features are a theme. For each, note expected impact (e.g., reduce surprise churn by catching issues early, improve renewal rates for engaged accounts). Present as bullet points. The tone emphasizes partnership with CS and a proactive approach.

Churn rate reduction quarter-over-quarter (e.g., from 5% to 3%). Also qualitative: improved customer satisfaction scores for accounts with executive sponsor touchpoints.

Blind Spot: Execution is key – these initiatives need clear owners and processes. Make sure Sales-CS responsibilities are defined (who updates health scores? who contacts the customer?). Without follow-through, even the best plan won’t move the needle. Emphasize accountability in the plan.

You want to formalize how renewals and churn risk are handled in forecasting. Draft a process: Renewal Pipeline in Forecast Calls: Include upcoming renewals in the weekly forecast review – e.g., have CS report a renewal forecast (commit/likely/at-risk for renewals similar to sales deals). At-Risk Escalation: Define that any renewal above $X or with high churn risk (health score low, etc.) is discussed by Sales leadership – actions assigned (like Sales engineer or Exec to assist CS, special offer, etc.). Net Retention Forecast: Begin projecting NRR in forecasts (so not just new sales, but add expected upsell and subtract expected churn). Collaboration Cadence: Sales and CS leads meet monthly specifically to review account health and expansion opportunities – ensure sales is aware of any churn risk well in advance. Present as 3-4 bullets. This will ensure we forecast existing customer outcomes, not just new biz.

Better visibility and accuracy in overall revenue forecasting (actual churn/renewal rates align closely with forecast; fewer surprise lost accounts). Improved cross-team action on at-risk accounts (some saves that would have otherwise churned).

Blind Spot: Ownership can be tricky – clarify who "owns" the renewal number in forecast (often CS). The process should augment, not override, CS processes. Also be careful not to double-count expansions (if CS forecasts them and sales does too). Align data and definitions between Sales and CS so this integrated forecast is coherent.

You are creating a brief playbook for AEs to drive expansions. Outline key steps: Account Research: Know the customer’s current usage and goals; identify where our product has additional modules or capacity that can help (e.g., feature X they haven’t bought could solve Y problem for them). MEDDIC for Upsells: Treat the expansion like a new sale – ensure Metrics (document ROI achieved so far and potential additional ROI), Economic Buyer (maybe higher for budget approval on expansion), Pain (any new challenges since initial sale that we can address). Joint Planning with CS: Work with the CSM on timing (e.g., 6 months before renewal) and strategy (CSM provides success data, AE focuses on commercial discussion). Proposal & Close: Simplified pricing for loyal customers, reference success achieved, handle any new procurement steps. Post-sale: Ensure implementation of upsell goes smoothly (coordinate with support) to reinforce decision. List these as bullets in a logical order. This playbook will be shared in a sales meeting to standardize expansion motions.

Increased expansion deal conversion rate and value (more upsells closed, higher net retention). Sales team follows consistent process for upsells (reflected in deal reviews).

Blind Spot: Reps might assume expansions are "easy" and skip steps – the playbook reminds them that upsells require qualification and strategy too. Also caution not to push unwanted expansions that could actually hurt customer relationship; ensure the playbook stresses identifying genuine needs, not just upsell for the sake of a number.

You need to draft a Performance Improvement Plan for due to sustained underperformance. Outline the PIP including: Areas of Concern: Specific metrics or behaviors (e.g., "Quota attainment 60% for H1 vs 90% target; generated only $X new pipeline vs $Y expected"). Improvement Goals: Clear, measurable targets for the next period (e.g., "Achieve at least 90% of monthly quota in the next 2 months", "maintain 3x pipeline coverage ongoing", "convert at least 1 deal/month from demo to close"). Action Plan: Bullet the actions will take ("Daily prospecting 8-10am with goal of 5 new outreach/day", "attend weekly coaching sessions on negotiation", "submit a weekly progress report every Friday"). Support Provided: What you/company will do ("Manager will join 1 sales call per week for coaching", "Enabling additional BDR support for lead generation in territory"). Timeline: e.g., "60-day PIP starting , midpoint review at 30 days". Consequences: State that failure to meet the plan may result in further disciplinary action up to termination. Use a formal tone. This document will be reviewed with HR and the rep.

PIP objectives met by deadline (e.g., rep attains specified targets within 60 days) or, if not, documentation supports next steps. Ideally performance improves and rep is retained.

Blind Spot: Goals must be realistic and time-bound – if they’re set too high or vague, the PIP will fail unfairly. Ensure understands and agrees to the plan. Also, involve HR early to align on wording and process. A PIP should be a genuine opportunity to improve, not just a paper trail for termination (unless improvement is truly unlikely).