Who's in the Room? A quick roll call

• Who from your organization will be directly involved in this CRM initiative? Please list names, titles, and primary responsibilities.
• Which of the people listed is the final decision-maker for CRM design and budget? Options: VP of Sales Operations, CRO / Head of Revenue, CIO / CTO, CEO / President, Head of Revenue Ops, Finance, Other
• Which stakeholder groups must we consult before changing workflows, fields, or reporting? Options: Sales leadership, Frontline sales reps, Marketing, Customer Success, IT / Engineering, Finance, Legal / Compliance, Product, Other
• Who will be the day-to-day project owner on your side (name/title) and who is their backup?
• Are there external parties (investors, partners, franchisees, vendors) whose approval or input is required? Options: Yes — investors, Yes — strategic partners, Yes — franchisees/distributors, Yes — third‑party vendor, No, Unsure

What If 'We're Aligned' Is Just a Nice Story?

• Imagine each sponsor wrote a one-sentence definition of success for this CRM project — how different do you think they'd be?
• Have any previous CRM or ops initiatives in your organization derailed because leaders disagreed? Tell us one example and its consequences.
• Which outcomes do different sponsors most prioritize? (pick all that apply) Options: Accurate pipeline reporting, Faster deal cycles, Higher win rates, Less admin for reps, Predictable forecasting, Cleaner customer data, Compliance / auditability, Better cross-team visibility, Other
• Who on the sponsor list is most likely to push back on change, and what is their typical concern?
• How aligned are your executive sponsors on prioritization and budget for this work? Options: Completely aligned, Mostly aligned, Somewhat aligned, Not aligned, Don't know

The Clock Is Real — What Breaks If We Miss It?

• If the go‑live slips past your next quarter, what strategic or operational consequences would follow?
• What target go‑live window are you aiming for? Options: Within 4 weeks, 4–8 weeks, 8–12 weeks, Next quarter, Next six months, No fixed date
• Are there immovable calendar events tied to the timeline (quarter close, product launch, M&A, audit, board review)? Select all that apply. Options: Quarter close / forecast, Product launch, M&A / acquisition, Budget cycle / planning, External audit / compliance, Sales kickoff, None, Other
• What is an acceptable delay window before we consider the project at risk (in days or weeks) and why? Options: <2 weeks, 2–4 weeks, 1–2 months, >2 months, Unsure — depends on scope
• If we need to compress the timeline, which scope elements are you willing to reduce or phase? Options: Data migration depth, Number of integrations at launch, Custom report deliverables, Training breadth, Phased rollout by team/region, No reduction — full scope required, Other

If Leadership Trusted the Dashboard Again

• Imagine leadership woke up and fully trusted the pipeline — what specific decisions would they make differently in the next 90 days?
• Which measurable signals would convince leaders to trust the pipeline? (pick up to 3) Options: Forecast accuracy within X%, Rep adoption rate, Consistent stage progression rules, Timely opportunity updates, Clean account hierarchies, Duplicate reduction rate, Integration uptime / data freshness, Other
• What numeric targets would you set for go‑live success (examples: adoption %, forecast variance, duplicate rate)? Please list values where possible.
• Who must sign final acceptance of reports and dashboards (name/title or role)? Options: CRO / Head of Revenue, VP Sales Ops, Finance, Sales leadership, Revenue Ops Committee, Other
• How will you measure behavior change among reps after launch (which KPIs or signals will demonstrate adoption)? Options: Login frequency, Opportunities updated within X days, Required fields completed, Usage of prescribed workflows, Reduction in manual spreadsheets, Number of coached sellers using CRM, Other

The Ugly Truth About Data, Integrations, and People

• If I said your migration will uncover three times more data issues than you expect, what would you want us to prioritize?
• Which of these data quality issues exist in your current system? Select all that apply. Options: Duplicate accounts/contacts, Broken account hierarchies, Missing or incorrect owner assignments, Stale leads/opportunities, Inconsistent or free‑text picklists, Historical data in spreadsheets, Other
• Do you have an estimate of the percent of records that are clean versus needing remediation? Options: >90%, 70–90%, 50–70%, <50%, Don't know
• Which integrations are critical at launch? (pick all that must work day one) Options: Email (Gmail/Outlook), ERP / Finance, Marketing automation, Support / ticketing, Product telemetry / usage, Contract repository / CPQ, Identity / SSO, Other
• Have you experienced integration failures in prior projects? Describe one example and the operational impact.

Who Will Hold the System's Heartbeat?

• If nobody owns governance after launch, the system regresses. Who will be accountable for ongoing CRM health? Options: Sales Ops, Revenue Ops, IT / Tech Ops, Sales Enablement, Customer Success / Post‑Sales, A cross‑functional governance committee, External partner, Other
• How often should governance and health‑check meetings occur during the first 90 days and long term? Options: Weekly during launch, Bi‑weekly for first quarter, Monthly, Quarterly after stabilization, Other
• What is your desired escalation path for production issues and who is on it (names/titles)?
• Who will be responsible for training, change management, and onboarding of new reps after launch? Options: Sales Enablement, Sales Leadership, Sales Ops / Rev Ops, External partner / vendor, Hybrid — shared responsibilities, Other
• Is there a budget or headcount allocated for ongoing optimization and maintenance post‑launch? Options: Yes, dedicated budget and staff, Yes, limited budget, No — will need to request, Unsure

Tell Us a Story — Scars, Wins, and What We Should Avoid

• Tell us about one CRM change that left a scar — what went wrong, who felt the pain, and how long did it take to recover?
• What's the best CRM or process change your org has executed? What made it stick?
• How do your sales reps currently feel about the CRM? Choose the best description. Options: Love it and use it, Tolerate it, Avoid it when possible, Distrust it, Varies significantly by team
• What incentives, coaching, or consequences have you used to drive adoption previously? Select all that apply. Options: Recognition programs, Quota or comp alignment, Mandatory tasks / field enforcement, Manager coaching, Gamification / contests, No formal incentives used, Other
• If we proposed a short proof‑of‑concept to build trust quickly, which single sales workflow should we demonstrate first and why? Options: Lead → Opportunity conversion, Opportunity stage progression & forecasting, Renewal / expansion workflow, Deal desk / CPQ flow, Account hierarchy consolidation, Other

Quick Snapshot: Where We Actually Are

• What's the CRM platform (and version or primary package) your team is using today? Options: Salesforce (Sales Cloud), Salesforce (Other/Custom), Microsoft Dynamics 365, HubSpot CRM, Zoho CRM, Other
• Who in your org uses the CRM every day? (pick all that apply) Options: Field sales reps, Inside sales/SDRs, Sales Ops, Marketing, Customer Success, Finance/Rev Ops, Engineering/IT, Leadership/Executives, Other
• How frequently do most reps actually update opportunities or activities in the CRM? Options: Multiple times per day, Daily, Weekly, Only at quarter-end/pipe reviews, Rarely/never
• Who owns day-to-day CRM configuration and data issues right now? Options: Sales Ops, IT/Platform Team, External vendor/partner, Individual sales managers, No single owner/fragmented
• Briefly describe one recent CRM frustration that someone on the team mentioned in the last month.

If We Do Nothing, What Breaks First?

• What single report or metric do leaders say they no longer trust—and what happens when they ignore it?
• How often does bad CRM data lead to a missed forecast, a lost deal, or a bad strategic decision? Options: Regularly (monthly+), Quarterly, Occasionally, Rarely, Never
• When pipeline numbers look wrong, who raises the alarm and how is it handled today? Options: Sales Ops triage, Sales leadership debate, Ignored until next quarter, Finance intervention, No clear process
• If the CRM became unusable tomorrow, what critical process would fail first? Options: Forecasting, Renewal/upsell tracking, Lead routing/SDR workflow, Sales reporting for execs, Customer 360 visibility, Other
• How would you describe the emotional impact on the team when CRM data is wrong—frustration, embarrassment, mistrust, something else? Options: Frustration, Embarrassment, Mistrust, Apathy, Blame between teams, Other

What Have You Quietly Forgiven?

• What processes or workarounds have you allowed to persist because fixing them felt too risky or costly?
• Which of these shadow systems do reps rely on instead of the CRM? (select all that apply) Options: Spreadsheets, Personal email threads, Shared docs (Sheets/Docs), Third-party sales tools (e.g., Outreach), None/We use CRM only, Other
• How long have those workarounds been in place? Options: Under 6 months, 6–12 months, 1–2 years, 2+ years, Unknown
• Tell us about one manual step your reps hate but still do—what is it and why hasn't it been fixed?
• How often do reps tell you the CRM adds admin time vs helps close deals? Options: Mostly adds admin time, About equal, Mostly helps close deals, Not sure / mixed feedback

Show Me the Data — Not the Dashboard

• If I asked for a truth set of closed-won deals for the last 12 months, how confident are you in its accuracy? Options: Very confident, Somewhat confident, Low confidence, No confidence
• Which data issues occur most frequently? (select up to 3) Options: Duplicate records, Missing contact details, Incorrect account hierarchies, Stale stages/statuses, Inaccurate close dates/amounts, Wrong ownership
• Do you currently enforce data validation (e.g., picklists, required fields) on critical fields? If yes, which ones? Options: Yes—standardized picklists, Yes—required fields enforced, Partial/soft enforcement, No enforcement, Not sure
• Who is accountable for data quality (ownership and SLA) for accounts, contacts, and opportunities? Options: Sales Ops, Individual reps, Sales managers, Data steward/BI team, No one defined
• Describe a recent example where bad data directly cost time or revenue (what happened and impact).

Automations: Helping or Hurting?

• Which automation in your CRM causes the most unexpected behavior or user complaints? Options: Lead assignment rules, Opportunity stage auto-updates, Email/task automation, Account merges/duplicate rules, Quote/order automations, Other
• How are automations documented, tested, and rolled back when they fail? Options: Formal testing + rollback plan, Ad-hoc testing, No testing or rollback, External partner manages
• How often do automation changes get deployed without stakeholder sign-off? Options: Often, Sometimes, Rarely, Never, Don't know
• What percentage of your CRM’s business logic lives in native workflows vs code/custom integrations? Options: Mostly native (75%+), Balanced (~50/50), Mostly custom code (75%+), Don't know
• When an automation misfires, what is the typical time-to-detect and time-to-fix? Options: Hours, 1–2 days, Several days, Weeks, Undetected until reported

Integrations: The Hidden Threads

• Which systems are integrated into the CRM (select all that apply)? Options: Email (Gmail/Exchange), Dialer/COGS tools, Marketing automation (Marketo/HubSpot), ERP/Finance, Customer success platform, Custom internal systems, None/Minimal integrations
• Which integration failures cause the most business disruption? Options: Leads not routing, Activity sync failures, Order/invoice mismatch, Duplicate contact creation, Reporting gaps, Other
• How are integrations monitored and who is alerted when they fail? Options: Automated monitoring + alerts, Manual checks by IT, Not monitored proactively, External partner handles
• Are there APIs or vendor-imposed limits that have previously constrained integration work? Options: Yes—rate limits or restricted APIs, Yes—cost/licensing limits, No constraints experienced, Not sure
• If an integration needed to be temporarily disabled during migration, what business processes would be impacted?

How Reps Really Work Daily

• What's the last field or UI change that made reps push back—and why did they resist it?
• Which parts of the sales workflow do reps complete in the CRM vs outside it? Options: Entire workflow in CRM, Mostly in CRM with some external steps, Majority outside CRM (spreadsheets/docs), Varies heavily by rep/team
• How much admin time per week does an average rep spend in the CRM? Options: Under 1 hour, 1–3 hours, 3–6 hours, 6–10 hours, 10+ hours
• What motivates reps to update the CRM today—coaching, incentives, compliance, or nothing? Options: Coaching/manager enforcement, Compensation/commission, Pipeline reviews, Personal discipline, No clear motivator
• Describe one workflow change that would immediately reduce admin time for reps.

Stakeholders, Ownership, and Decision Speed

• Who needs to sign off on configuration, migration, and cutover decisions? Options: VP Sales Ops, CRO, CIO/IT, Finance/Legal, External vendor, Other
• When there's a conflict between sales needs and IT constraints, which side usually wins? Options: Sales, IT, Compromise/negotiation, Depends on executive sponsor, No clear pattern
• How quickly can your organization make a go/no-go decision during a migration window? Options: Same day, 24–48 hours, Several days, Weeks
• What’s your appetite for parallel runs (running old and new systems in tandem) to validate results? Options: High appetite—prefer parallel run, Moderate—short parallel run ok, Low—prefer cutover, Unsure
• Who on the team is most likely to resist change and why?

What Would Make You Believe Again?

• What concrete outcomes would restore leadership’s trust in CRM data (pick up to 3)? Options: Accurate closed-won history, Clean account hierarchies, Reliable pipeline forecast, Near real-time activity sync, High rep adoption rates, Clear SLA for data quality
• What is an acceptable timeline to see measurable improvement in data trust and rep adoption? Options: 30 days, 60–90 days, One quarter, Two quarters, Longer than 6 months
• Which of these would convince you a migration was successful? (select all that apply) Options: Data accuracy validated vs source, Reps report reduced admin time, Forecast error reduced by X%, No critical integration failures, Stakeholder sign-off on acceptance criteria
• What quick win could we aim for in the first 30–60 days to build momentum? Options: Fix duplicate rules for top accounts, Stabilize lead routing, Publish one trusted forecast report, Reduce required fields causing friction, Other
• Which risks keep you up at night for this project, and how severe would their impact be (briefly)?

Next Practical Steps — Priorities, Constraints, and Signals

• If we could only tackle three things in discovery, which would you prioritize? Options: Data quality audit, Key workflow mapping with reps, Integration inventory and health-check, Automation/rule inventory, Stakeholder alignment and acceptance criteria
• What hard constraints should we plan around (freeze windows, compliance, budget, license limits)?
• Who should be in the room for final acceptance of migration and adoption metrics? Options: VP Sales Ops, CRO, IT/Platform lead, Sales managers, Finance/Rev Ops, External partner
• What's the single most important signal you'd want to see before greenlighting a broader rollout? Options: Trusted dataset verified, Rep workflow validated in pilots, Integrations stable, Stakeholder buy-in documented, Other
• Any other context, stories, or examples that would help us prioritize and scope this discovery effectively?

Quick Intro — What’s Top of Mind Right Now?

• Tell us your name, role, and the one sentence that best describes why you asked for this conversation today.
• What type of CRM project is this (pick the closest)? Options: Greenfield implementation, Migration from another CRM, Optimization of existing CRM, Integration-heavy project, Other
• Who is the primary sponsor or decision owner for this project? Options: VP of Sales Operations, CRO/Head of Sales, CIO/Head of IT, Head of Revenue Operations, Other
• What is your target go-live window? Options: < 1 month, 1–2 months, 3–4 months, 5–6 months, 6+ months, Unsure
• What would you most like us to understand about your situation before we dig in?
• Which of the following best describes the trigger that started this project? Options: Leadership distrusts pipeline, New CRO/strategy, User adoption collapse, Merger or acquisition, Platform reaching end-of-life, Other

If Your CRM Could Admit One Lie, What Would It Say?

• When you look at your pipeline reports today, what’s the one thing that makes you doubt them?
• How often does leadership challenge forecast numbers? Options: Weekly, Monthly, Quarterly, Rarely, Never
• Give an example of a recent decision that was affected (positively or negatively) by data you now distrust.
• Which sources contribute most to the data problems you see? Options: Manual rep entry, Legacy system migration, Multiple CRMs, Marketing automation imports, ERP/finance integrations, Other
• Who usually notices the bad data first—sales reps, managers, ops, finance, or customers? Options: Sales reps, Sales managers, Sales operations, Finance, Customer success, External partners
• How does it feel when a payout, forecast, or strategic decision is questioned because of CRM data?

Where the Numbers Stop Adding Up

• How inaccurate are your forecasts today, on average? Options: > 50% off, 25–50% off, 10–25% off, < 10% off, We don’t track accuracy
• What are the most common discrepancies you see between CRM and actual outcomes (e.g., closed deals missing, inflated deal stage ages, duplicate accounts)?
• Which reports or dashboards does leadership insist must be accurate at go-live? Options: Pipeline by rep/team, ACV/MRR forecasts, Vertical/segment dashboards, Opportunity aging, Account hierarchy rollups, Other
• When a report is wrong, how do teams usually try to 'fix' it? Options: Manual spreadsheets, Ad hoc SQL/BI fixes, Avoid using CRM, Stop reporting certain metrics, Create shadow systems
• Tell us about one recent forecast miss—what caused it and what was the impact?
• Which downstream teams suffer most when CRM reports are unreliable? Options: Sales leadership, Finance/FP&A, Marketing, Customer success, Product, Executive team

Who Pulls the Strings — and Who Gets Blamed When Things Break?

• Who will sign off on acceptance at launch and who will be asked to take responsibility if adoption is low?
• Which stakeholders must be involved for deployment decisions (select all that apply)? Options: VP Sales Ops, CRO, CIO/IT, Sales leadership, Finance, Legal, Customer Success, Marketing
• Describe the formal governance for CRM changes today—committees, SLAs, change windows, or none at all.
• Who is the day-to-day owner of data quality, and what authority do they have to enforce standards? Options: Sales Ops, IT/Data Team, Revenue Ops, Sales Manager, No clear owner, Other
• How have past platform changes been communicated to reps and managers? Options: Town halls, Email only, Manager briefings, Training sessions, No formal communication
• If a go-live issue escalates, what’s the fastest route to a decision to pause or rollback? Options: Technical owner signs off, Project steering committee, Executive sponsor decision, No established process

The Migration You’re Afraid Will Break Everything

• Which of these migration fears keeps you up at night? Options: Duplicated records, Broken account hierarchies, Lost activity history, Integration failures, Performance impacts, Compliance/data loss
• What systems are in-scope for migration or integration (select all that apply)? Options: Existing CRM, Marketing automation, ERP/Finance, Customer success platform, Data warehouse/BI, Email/calendar sync, Other
• Approximately how many records will need to be migrated (contacts, accounts, opportunities)? Options: < 10k, 10k–100k, 100k–500k, 500k–1M, >1M, Unsure
• Describe current data quality: duplicate rate, missing required fields, and obvious mapping conflicts.
• Do you currently have full exports/backups and a sandbox that mirrors production for dry-runs? Options: Yes, both exist, Exports only, Sandbox only, Neither exists, Unsure
• What would be an acceptable rollback plan in your view—restore backup, preserve legacy read-only access, or staged rollback? Options: Full restore from backup, Staged rollback by module, Legacy system kept read-only, Manual corrections only, Other
• Who must approve the rollback plan before we execute migration rehearsals? Options: Project sponsor, IT/CIO, Legal/Compliance, All stakeholders, No formal approver

How Your Reps Really Use (or Ignore) the System

• How would your reps describe the CRM today: lifeline, necessary evil, or something they avoid? Options: Lifeline, Useful but clunky, Necessary evil, Avoid entirely, Other
• How much time does an average rep spend on CRM admin each week? Options: < 1 hour, 1–3 hours, 4–7 hours, 8–12 hours, > 12 hours, Unsure
• Which CRM tasks do reps regularly skip or do inconsistently (e.g., activity logging, stage updates, contact enrichment)? Options: Activity logging, Updating opportunity stages, Contact/account enrichment, Forecast submissions, Using tasks/follow-ups, Other
• What incentives or enforcement exist today to drive rep data hygiene and pipeline updates? Options: Comp/payout tie-ins, Manager spot checks, Automated validation rules, No enforcement, Other
• Tell us about the last time a workflow change improved rep behavior—what changed and why did it stick?
• How do you currently measure adoption success in the first 90 days after a change? Options: % of reps active, Required fields completed, Forecast accuracy, Reduction in manual spreadsheets, Other
• Which types of rep training have been most effective historically? Options: Hands-on workshops, Manager-led coaching, Microlearning videos, Documentation only, Peer mentoring

What Success Actually Looks Like — Not the PowerPoint Version

• If you had to write one measurable acceptance criterion for this project, what is it?
• Which three metrics will leadership use to decide this project was worth it? Options: Forecast accuracy, Rep adoption rate, Pipeline coverage, Sales cycle length, ARPA/ACV increases, Operational time saved
• What is a realistic adoption target at 30, 60, and 90 days post-launch? Options: 30% / 50% / 75%, 50% / 70% / 85%, 70% / 85% / 90%, Custom targets (describe below)
• How will you validate that account hierarchies and rollups are correct after migration? Options: Automated reconciliation reports, Manual sampling and sign-off, Stakeholder walkthroughs, BI/dashboard validation, Other
• Who will perform the final acceptance sign-off and by what date?
• If adoption targets aren’t met, what remediation actions would you expect us to include in the plan? Options: Additional training, Process redesign, Incentive changes, Rollback/partial rollback, Extended support

If We Started Tomorrow, What Would Make Us Stop the Project?

• What are the non-negotiable risks that would force a pause or stop (e.g., legal/compliance issues, major data loss, critical integration failure)?
• Which third-party vendors or internal teams are single points of failure for your launch? Options: Email provider, ERP/Finance team, Data warehouse vendor, External integration partner, None
• What budget, timeline, or resource constraints could realistically derail delivery? Options: Budget freeze, Key resource departure, Competing initiatives, Extended procurement, Other
• Describe the communication plan you'd want if a serious issue required us to halt deployment mid-migration.
• Who should be on our emergency escalation list (name, role, preferred contact method)?
• What would you need to see during rehearsals (dress rehearsals/dry runs) to feel comfortable proceeding? Options: Successful end-to-end migration, Zero data loss in samples, Integration validations pass, User acceptance testing sign-off, Other

Getting Comfortable: A Fast, Honest CRM Snapshot

• Tell me briefly—what prompted you to explore a CRM refresh or migration right now?
• Which role is the primary decision-maker for CRM success in your org? Options: VP Sales Operations, CRO / Head of Revenue, CIO / IT Leader, RevOps Director, Head of Sales, Other
• How long has your team been working with the current CRM configuration or setup? Options: Less than 6 months, 6–12 months, 1–3 years, 3+ years, Never had a formal CRM
• If you had to pick one short phrase that captures your current CRM feeling—what is it?
• Which of these best describes the current project type you’re considering? Options: Greenfield implementation, Full migration from another CRM, Optimization & cleanup, Integration-focused (email/ERP/etc.), Other

What If Your CRM Is Quietly Costing You Deals?

• How confident are you that your current pipeline numbers reflect real, closable opportunities? Options: Very confident, Somewhat confident, Doubtful, Not confident at all
• Where do you see the biggest gap between what leadership expects from pipeline reporting and what you actually get?
• Give an example of a recent deal or forecast surprise that made you question the CRM’s reliability.
• Which of these are present today when you run pipeline reports? Options: Outdated opportunity stages, Duplicate accounts/contacts, Missing closed-won records, Inconsistent forecasting fields, Disconnected integrations, Other
• If your CRM failed to improve, what would be the most likely business consequence in the next 6–12 months? Options: Missed revenue targets, Loss of executive trust, Longer sales cycles, Higher rep churn, Increased manual work, Other

Where the Work Actually Happens — The Rep Experience

• Why do reps treat the CRM like a last-resort filing cabinet rather than a selling assistant?
• How much time does an average rep spend per day on CRM data entry and admin tasks? Options: Less than 15 minutes, 15–30 minutes, 30–60 minutes, More than 60 minutes
• Which CRM tasks do reps resist most—logging activities, updating stages, account linking, or pipeline notes? Options: Logging activities, Updating stages/opportunity fields, Maintaining account/contact hierarchies, Adding contextual notes, Other
• Share a concrete story where a rep’s workflow was blocked or slowed by the CRM—what happened and what did they do instead?
• Which current workflows absolutely must stay the same for reps to keep selling without friction?

The Truth About Data: Can You Put Money on It?

• If you had to bet $100 on the accuracy of your account hierarchies and rollups, would you take the bet? Options: Yes, confident, I'd hedge the bet, No—too risky, Not sure
• Estimate the current duplicate or fragmented account/contact rate that affects reporting and owner visibility. Options: <1%, 1–5%, 6–15%, 16–30%, >30%, Don't know
• Which integrations feed pipeline or account data into your CRM today (select all that apply)? Options: Marketing automation (e.g., HubSpot/MA), Email sync (Gmail/Outlook), ERP/Finance, Customer Success/Support, Product analytics, None of the above, Other
• Describe any past migration or sync that created broken hierarchies, lost ownership, or inexplicable duplicates—what went wrong?
• What checks or controls would restore your trust in the data after a migration (e.g., samples validated, reconciliation scripts, ownership audit)? Options: Field-by-field reconciliation, Top accounts manual audit, Automated duplication report, Sampleed closed-won validation, Third-party data match, Other

What’s Keeping Your Leadership Up at Night?

• If you were in the VP of Sales’ shoes, what single CRM outcome would restore your confidence in forecasts?
• Which success signals would make leadership accept the CRM as the single source of truth? Options: Consistent forecasting accuracy, Rep adoption >85% in quarter 1, Account hierarchy correctness, Automated reconciled revenue reports, Operational SLAs met, Other
• How does leadership currently validate or challenge pipeline—regular QA, deal reviews, data audits, or ad-hoc checks? Options: Weekly deal review meetings, Quarterly data audits, Ad-hoc spot checks, No formal validation, Other
• What acceptance criteria (specific numbers or behaviors) would you need to sign off on a successful deployment?

Show Me the Motion: Using Real Scenarios to Validate

• If I asked a ramped rep to run a live deal through the new CRM today, what would break first?
• Which single sales scenario is the highest-value proof-of-concept for you (e.g., complex account expansion, multi-product new logo, renewals with cross-sell)? Options: New logo complex sale, Account expansion/land-and-expand, Renewal + cross-sell, High-volume SMB motion, Channel-partner influenced deal, Other
• What real account or deal examples can we use during discovery to validate reporting and workflows?
• Which metrics must the POC prove to be acceptable (e.g., time-to-update, forecast accuracy delta, reduction in admin minutes)? Options: Forecast accuracy improvement, Rep admin time reduction, Deal-stage completion rate, Reduction in duplicates, Integration latency under threshold, Other
• How would you like POC validation presented—live walkthroughs, reconciliation spreadsheets, or scripted test cases? Options: Live walkthroughs, Reconciliation spreadsheets, Recorded demos + logs, Automated test cases, Combination

Migration and Integration Fear-Test

• What's the most damaging outcome you can imagine from a migration or integration gone wrong?
• Do you have a rollback plan or freeze criteria defined today? Options: Yes—documented and tested, Yes—documented but untested, Planning to create one, No
• Who must be given access and approval during migration windows (select all that apply)? Options: Sales leadership, RevOps/CRM admin, IT/Security, Finance, Customer Success, External partner, Other
• Which environments are available for dry-runs and validation (sandboxes, staging, partial backups)? Options: Full sandbox, Partial sandbox, Staging with sample data, Backup snapshots only, None
• What sample size or set of accounts would you require validated before a full cutover (e.g., top 20 accounts, 200 random records)?

Adoption and Change: What Will Motivate Your Team?

• If adoption stalls post-launch, what do you think will be the real reason—UX friction, missing incentives, lack of training, or something else? Options: UX friction, Insufficient training, No incentive/compensation alignment, Too many fields/processes, Trust in data, Other
• Which training formats have historically worked best for your reps? Options: Instructor-led workshops, Short task-based videos, Hands-on shadowing, Playbooks + cheat sheets, Peer coaching, Other
• What percentage of reps adopting within the first quarter would make you consider the project a success? Options: >90%, 80–90%, 60–79%, <60%
• Which incentives or enforcement mechanisms are you willing to deploy to improve adoption (e.g., quota gating, leaderboard, reduced admin fields)? Options: Quota/forecast gating, Leaderboards/recognition, Reduced required fields, Automation for data capture, Role-based workflows, Other
• Describe one small change we could implement that would remove a daily pain for reps and increase willingness to use the CRM.

Triggers, Governance, and The Mutual Commit

• At what exact metric threshold would you pause deployment and investigate (e.g., duplicate rate > X%, adoption < Y%)?
• Who needs to be on the governance committee for launch and the 90-day optimization window? Options: VP Sales Ops, CRO, CRM Admin/RevOps, IT/Security, Sales Enablement, Customer Success, External partner
• What commercial or non-commercial commitments do you expect from a partner to feel comfortable moving forward (e.g., milestone payments, acceptance gates, SLA for fixes)?
• How often should governance meet during the rollout—weekly, bi-weekly, monthly? Options: Weekly, Bi-weekly, Monthly, Ad-hoc as needed
• What's the single earliest milestone that would prove this project is worth continuing after launch? Options: POC shipping successful, Data reconciliation pass, Adoption target hit, Leadership sign-off on reports, Other