Quick Intro: Who's driving this initiative?

• Which primary business outcome is pushing this project right now? Options: Increase marketing-sourced pipeline, Improve MQL → SQL quality, Prove multi-touch attribution, Fix CRM data and sync reliability, Reduce lead leakage between systems, Other
• Who is the single point of contact we should work with day-to-day?
• Who is the ultimate decision-maker for selecting and approving a vendor (title or role)? Options: CMO, VP/Director Marketing Ops, VP Demand Gen, Head of Revenue Ops, CRO, Other
• Roughly how soon does the decision need to be made to meet your next-quarter goals? Options: Within 2 weeks, 2–4 weeks, 1–2 months, By next quarter end, Flexible / No fixed date
• Are there any non-negotiable constraints (budget ceiling, procurement windows, board deadlines)? Please list.

Who Really Signs Off (Even If No One Says So)

• Most orgs assume approval is straightforward—who tends to be the actual gatekeeper that surprises teams later? Options: CFO/Finance, Legal/Compliance, IT/Infrastructure, Sales Leadership, COO/CEO, Procurement, Other
• How does the formal approval process work—committee, single approver, procurement playbook, or informal influence? Options: Single approver, Small committee, Formal procurement process, Pilot then executive sign-off, Informal champion-led
• Who has veto power over integrations, data sharing, or vendor selection—and what have they historically cared most about? Options: IT — security/data, Finance — ROI/contract terms, Legal — compliance/TOS, Sales — lead quality, Marketing leadership — platform fit, Other
• When someone has pushed back in past projects, what were the top three reasons they gave?
• If I asked those gatekeepers what would convince them to say yes, what's their one-line answer?

What If Time Isn’t on Your Side?

• If the project slips beyond your target quarter, what tangible consequences happen (board questions, missed quota, lost budget)?
• Which external deadlines are non-negotiable—fundraising, product launch, board review, quarter close, other? Options: Board review, Quarter close, Product launch, Budget cycle, Customer commitments, Other
• How flexible is the timeline if initial integration takes longer—are there contingency plans or phased rollouts you’d accept? Options: Rigid — must hit date, Somewhat flexible — +/- 2 weeks, Phased acceptance ok, Flexible — focus on quality
• Who will own keeping the timeline honest inside your organization (title/role)?
• What’s the longest delay you’ve tolerated on a similar project—and how did that impact internal support and momentum?

Are We Measuring The Same Thing?

• If marketing says 'success' and finance says 'success', do those look the same to you—or are they different? Options: Aligned, Partially aligned, Misaligned but negotiable, Completely different
• Which of these KPIs will determine whether this project is a win for your team? Options: MQL→SQL conversion rate, Leads accepted by Sales, Attribution credit to pipeline, Deliverability rates, CRM sync error rate, Time-to-first-qualified-lead
• Please provide current baseline numbers or ranges for the metrics you selected above (e.g., MQL→SQL %, weekly accepted leads, attribution gap).
• Who outside marketing needs to be satisfied with these metrics (Sales VP, CFO, CEO, Board)? Options: Sales VP, CRO, CFO, CEO, Board, Other
• How will success be validated—internal dashboard, third-party audit, weekly review with execs, signed acceptance by Sales? Options: Internal dashboard, Executive review meeting, Signed acceptance criteria, Third-party validation, Other

Executive Buy-In: Proof They Want (Not Just Need)

• What concrete artifacts would make executives comfortable approving this project (pilot results, ROI model, security sign-off, SLA)? Options: Pilot campaign report, ROI projection (3–6 months), Security/compliance review, Integration SLA, Reference customers, Other
• Has your leadership required vendor references or similar POC outcomes before signing off in past projects? If so, what did they ask to see?
• How risk-averse is your executive team on vendor changes—do they prefer incremental pilots or all-in migrations? Options: Prefer small pilots, Open to phased migration, Prefer full migration if vendor proven, Depends on vendor reputation
• Who will need to be included in a live demo or pilot review for final acceptance (name/role)?
• If we deliver a pilot that hits the agreed acceptance criteria, what internal approvals still remain before commercial terms can be finalized?

Sales & Operations: Partnering or Posturing?

• Do sales leaders currently treat marketing-qualified leads as helpful or as noise—and why do you think that’s changed or stayed the same? Options: Helpful and used, Skeptical but open, Mostly ignored, Hostile to MQLs
• What specific acceptance criteria would make Sales act on a lead immediately (score threshold, enriched fields present, fit data, buyer intent signals)? Options: Score threshold, Required fields present, Intent signal threshold, Account fit match, Other
• How does your current lead handoff work (automated CRM push, daily list, SDR triage, other)? Options: Automated CRM push, Daily list/email, SDR review queue, Manual assignment, Other
• Has sales rejected vendor pilots before because scoring didn’t match their expectations? Tell us about a specific time and what changed.
• What governance or SLA would make handoffs reliable (SLA time to contact, lead ownership, notation standards)? Options: Time-to-contact SLA, Clear ownership field, Lead enrichment standard, Weekly syncs, Other

Organizational Roadblocks: What's Really Blocking Progress?

• Beyond technical integration, what internal factors have derailed similar projects (resourcing, politics, data access, competing priorities)? Options: Insufficient resources, Competing priorities, No data access, Lack of executive support, Change resistance, Other
• Who will need to give data access for CRM and marketing systems, and are they already on board?
• If people need to change how they work (new workflows, responsibilities), how willing is the team to adopt that change? Options: Very willing, Somewhat willing, Resistant, Undetermined
• Who inside the org is a natural change champion we should partner with (name/role) and why will they influence others?
• What training or enablement will feel acceptable to your team post-deployment (hands-on workshops, playbooks, office hours, train-the-trainer)? Options: Hands-on workshops, Playbooks and templates, Office hours/consulting, Train-the-trainer, Self-service docs

Forging the First Agreement: Small Bets, Big Signals

• If we propose a POC that validates lead scoring, deliverability, and CRM sync using one campaign, would that be sufficient to drive approval to proceed? Options: Yes — sufficient, Partially sufficient — need additional evidence, No — need broader pilot, Unsure
• What three acceptance criteria must the POC meet for stakeholders to recommend full rollout?
• Who will sign the POC acceptance document on your side (name/role)?
• What communication cadence do you prefer during the POC—weekly checkpoints, twice-weekly standups, asynchronous updates? Options: Weekly checkpoints, Twice-weekly standups, Asynchronous updates, Ad-hoc as needed
• Are there quick wins we should aim for in the first 2–4 weeks to keep executive sponsors confident? Options: Improved deliverability, First set of Sales-accepted leads, Baseline attribution report, CRM sync stability

Closing the Loop: Who Agrees to What Next?

• Given everything we’ve discussed, how ready do you feel to commit to a clearly scoped POC within the next 30 days? Options: Ready to commit now, Need minor approvals, Need several approvals, Not ready
• What are the three immediate actions you need from us to move a decision forward (proposal, security review, reference call, technical scoping)? Options: Detailed proposal, Security/compliance docs, Reference customers, Technical scoping session, ROI model
• Who should be on the kickoff call from your side (name and role)—include the person who can remove blockers fast.
• Finally, what would make you say 'this discovery was worth our time' after the kickoff?

Quick Start — Who Are We Working With?

• Which of these best describes your role in the project? Options: Director of Marketing Ops, VP Demand Gen, CMO, Revenue Ops Manager, IT/Integration Lead, Other
• What is the primary CRM or customer system you currently use? Options: Salesforce (Sales Cloud), Microsoft Dynamics 365, HubSpot CRM, Oracle NetSuite CRM, Pipedrive, Custom/Proprietary, Multiple CRMs, Other
• Roughly how many contacts are in the CRM you’ll migrate or sync with? Options: 50k–150k, 150k–500k, >500k, <10k, 10k–50k
• Who are the core stakeholders we should expect to engage with during discovery and integration? Options: Marketing Ops, Revenue Ops, Sales Leadership, IT/Integrations, Legal/Compliance, Data Team/Analytics, Customer Success, Other
• What timeframe does your leadership expect to see initial results (e.g., POC validation)? Options: Within 2 weeks, 2–4 weeks, 4–8 weeks, In the next quarter, Longer than a quarter

What If Your CRM Is Lying to You?

• If I asked your Head of Sales whether the CRM contact data is trustworthy on a scale of 1–10, where would they score it—and why? Options: 1–3 (poor), 4–6 (mixed), 7–8 (good), 9–10 (very reliable)
• Which of these data quality issues shows up most often in your reports? Options: Missing email addresses, Wrong job titles/roles, Duplicate records, Stale engagement timestamps, Incorrect lead source attribution, Broken or missing account links
• Can you share a vivid example of a time CRM data caused a visible business problem (e.g., lost pipeline, bad attribution, sales rejection)? Tell the story.
• About what percentage of your active marketing lists lack a validated engagement score or fit score today? Options: 0–10%, 10–30%, 30–50%, 50–75%, 75%+
• How does it feel internally when reports produced from CRM data are questioned by sales or finance? Options: High urgency — causes friction, Moderate — requires rework, Low — accepted as normal, We rarely get challenged

Where Does Data Fall Through the Cracks?

• Which systems feed contact and activity data into your CRM today? Options: Marketing automation / ESP, Website tracking/analytics, Ad platforms (LinkedIn/Google), Event/platform registrations, Data enrichment vendors, Manual uploads/spreadsheets, Other
• Which inbound sources are most trusted for lead attribution—and which do you suspect are undercounted or missing? Options: Web forms, Ad clicks, Email engagement, Event attendance, Sales-entered leads, Third-party lists, Other
• What common field-level gaps do you see when you inspect random contact records (e.g., missing company size, industry, lead source, last activity)? Options: Company, Title/Role, Email validity, Lead source/campaign, Account association, Engagement timestamp, Custom scoring fields
• How long have these pipeline-impacting data issues been present, and have they gotten better, worse, or stayed the same? Options: New (few weeks), Months, Over a year, Multiple years
• If someone asked you what's the single most common reason a lead gets 'lost' between marketing and sales, what would your answer be?

If Integration Breaks Tomorrow, What Stops?

• Which sync patterns are critical for your ops — real-time, near-real-time, or batch — and why? Options: Real-time (instant), Near-real-time (minutes), Batch (hourly/daily), Ad-hoc/manual exports
• Which direction do your integrations need to support? (Select all that must be bi-directional) Options: Marketing → CRM, CRM → Marketing, CRM → Analytics/Warehouse, Third-party enrichment → CRM
• What happens today when a sync error or mapping mismatch occurs—how is it detected and who fixes it? Options: Automated alert + ops fixes, Sales flags issues ad-hoc, We rely on manual audits, Issues go unnoticed for weeks
• Are there existing SLAs or handoffs between marketing and sales for MQL creation, handoff, and feedback? If yes, summarize them. Options: Yes — well documented, Yes — informal, No SLAs, We're in negotiation
• Which of these would cause the most business pain if the CRM integration failed for 48 hours? Options: Leads not handed to sales, Incorrect attribution reporting, Campaigns sending to wrong segments, Sales not seeing recent activity, Billing/invoicing impacts

Show Us the Records — What Do They Reveal?

• Can you provide sample records for a typical lead, an account, and a contact activity log? Which format is easiest for you to extract? Options: CSV/Excel export, API extract (JSON), Database query dump, Sample via BI dashboard, We need help extracting
• How many sample records can you pull for a POC validation (min, typical, max)? Options: <100, 100–1,000, 1,000–10,000, 10k–50k, 50k+
• When you scan sample records, what surprises you most—missing fields, odd timestamps, duplicate contacts, or incorrect campaign tags? Options: Missing fields, Inconsistent timestamps, Duplicates, Wrong campaign/source tags, Unexpected custom field values
• Who needs to approve anonymized samples for us to review if there are privacy concerns? Options: Marketing Ops, Legal/Privacy, IT/Security, Data Team, Not required
• If we validate a sample and find mapping issues, how quickly can your team fix the source or provide corrected extracts? Options: Within 24 hours, 2–3 business days, Within a week, Longer / needs planning

Who Gets Blamed When Scores Go Wrong?

• How do you define an MQL today—what fields, behaviors, or scores trigger a handoff to sales? Options: Score threshold, Behavior + fit rules, Manual qualification, Campaign-specific rules, Other
• How often is your scoring model reviewed and who signs off on changes? Options: Weekly, Monthly, Quarterly, Ad-hoc, Never formally reviewed
• What proportion of MQLs are accepted by sales without dispute today (approx)? Options: >90%, 70–90%, 50–70%, <50%
• When a lead is rejected by sales, what feedback is captured and how does it flow back into scoring or CRM fields? Options: Structured feedback + automatic sync, Email/Slack notes only, Rarely captured, Captured manually then analyzed
• Tell us about a specific scoring mistake that caused a missed opportunity or wasted effort—what happened and what did you learn?

If We Could Snap Our Fingers, What Would Be Different?

• Describe the one mapping or field transformation that, if fixed, would free the most value (e.g., account linkages, lead source accuracy).
• Which acceptance criteria would make the POC feel undeniably successful to marketing, sales, and finance respectively? Options: Scoring accuracy aligns with sales, Reliable CRM sync with no duplicates, Attribution matches closed revenue, Deliverability within thresholds, All of the above
• What would a believable success metric look like at 30 days, 90 days, and 6 months?
• If we could automate one recurring data hygiene task for you, which should we pick first? Options: Duplicate de-duplication, Email validation, Auto-assign accounts, Standardize titles/roles, Map lead source consistently
• How would you prefer acceptance evidence to be presented—sample record comparisons, side-by-side dashboards, or signed stakeholder confirmation? Options: Sample record comparisons, Side-by-side dashboards, Stakeholder sign-off, Automated test reports

What's the Real Risk Budget?

• How risk-tolerant is leadership around changes to production CRM data during a POC? Options: Very risk-tolerant (happy to test live), Somewhat (prefer sandbox first), Low (no changes to prod allowed), Unsure / need to check
• Which of these constraints matter most for integration work? Options: PII/privacy regulations, Internal security policies, Firewall/VPN restrictions, No external APIs allowed, Change control windows
• Do you have a formal rollback plan and a defined owner for rollbacks if something goes wrong? Options: Yes, documented and owner assigned, Plan exists but no owner, No formal rollback plan, We rely on vendor to roll back
• What level of logging and observability do you expect during the POC (real-time alerts, daily reports, weekly summaries)? Options: Real-time alerts + daily reports, Daily reports only, Weekly summaries, Ad-hoc reporting
• Are there compliance or audit teams that must review integration specs before we start? If yes, who are they? Options: Legal/Privacy, Security/IT, Internal Audit, Not required

How Fast Can We Run a Real Test?

• Do you currently have a sandbox or test environment that mirrors production CRM data and mappings? Options: Yes, full mirror, Partial test environment, No, but we can provision one, No test environment available
• What is a realistic calendar window to run an end-to-end POC that includes CRM sync, lead scoring validation, and attribution checks? Options: 1–2 weeks, 2–4 weeks, 4–8 weeks, Longer than 8 weeks
• Which campaign or workflow would you want to use for the POC so it reflects real conditions? Options: Nurture welcome series, Paid acquisition campaign, Event follow-up workflow, Sales-sourced demo requests, Other
• Who needs to be available during the POC for quick decisions, mappings, or approvals? Options: Marketing Ops engineer, Sales ops lead, IT/Integration engineer, Data analyst, Legal/Privacy
• What’s the minimum set of KPIs we must collect during the POC to evaluate CRM integration health? Options: Sync success rate, Duplicate rate, Lead handoff latency, Score alignment with sales, Attribution match rate

Who Will Hold the Thermometer After Launch?

• After POC, who will own ongoing data governance and mapping changes? Options: Marketing Ops, Revenue Ops, IT/Integration, Shared rotation, We need to assign
• What cadence do you want for post-launch audits and scoring recalibration? Options: Weekly for first month, Monthly, Quarterly, Ad-hoc / as needed
• Which dashboards or alerts would make sales and marketing feel comfortable that the CRM sync is healthy? Options: Real-time sync dashboard, Daily error summary, Weekly health KPI report, Automated SLA breach alerts
• What training, documentation, or runbooks would help your team own mappings and fixes after we hand over? Options: Step-by-step runbooks, Recorded walkthroughs, Live training sessions, Access to sandbox for practice, All of the above
• Who should be the single point of contact for integration emergencies after go-live? Options: Marketing Ops lead, Revenue Ops lead, IT/Integration lead, Vendor support contact, TBD

Getting Practical — Permissions, Samples, and Next Steps

• Which authentication method does your CRM environment require for integrations? Options: OAuth2, API key, Service account / SSO, VPN/Private network, Other
• Who can provision a sample API key or temporary access for us to run a dry mapping test? Options: IT Admin, CRM Admin, Marketing Ops, Third-party vendor, No one available right now
• What format should our deliverable take after discovery—technical mapping doc, sample record redline, or prioritized remediation backlog? Options: Technical mapping doc, Sample record redline, Prioritized remediation backlog, All three
• When would you like us to deliver a proposed integration plan and a short list of blockers after we receive sample data? Options: Within 48 hours, 3–5 business days, Within 2 weeks, Longer as needed
• Is there anything else—political, technical, or timing-related—that we should know now to avoid surprises?

Quick Read: Where Are We Right Now?

• In one sentence, how would you describe your current readiness to begin deployment? Options: Ready to start, Mostly ready with minor gaps, Significant gaps but can proceed, Not ready — need more planning
• Which CRM(s) and core systems must be integrated for this initial phase? Options: Salesforce, HubSpot, Microsoft Dynamics 365, Oracle NetSuite, Marketo, Other
• Roughly how many contacts are in scope for the POC / initial migration? Options: < 10,000, 10,000–50,000, 50,000–200,000, 200,000–500,000, > 500,000
• What is your target launch date for the first workflow (dd/mm/yyyy or quarter)?
• Who is the executive sponsor and the day-to-day sponsor for this project (role/title)? Options: Director of Marketing Operations, VP Demand Generation, CMO, Head of Revenue Ops, CRM Admin, Other
• How does your team feel about the timeline and workload required for this deployment? Options: Very confident, Somewhat confident, Concerned but hopeful, Worried/overwhelmed

Who Actually Holds the Keys?

• What would happen if the person you expect to grant system access was unavailable on day one?
• List the named owners (role/title) who can grant: API access, CRM admin, DNS/Email admin, and security approval. Options: Director of Marketing Operations, CRM Admin, IT/Security Manager, DevOps/Platform Engineer, VP Demand Gen, Other
• Do you use SSO / centralized identity (Okta, Azure AD) for provisioning vendor access? Options: Yes — Okta, Yes — Azure AD, Yes — Other, No — separate accounts, Not sure
• How quickly can those owners typically grant required access once requested? Options: Within hours, 1–2 business days, 3–5 business days, Longer / depends on change window
• Who is the escalation contact and backup if access stalls?

If This Launch Stumbles, Where Will It Break?

• If the deployment fails in week one, what single preventable cause would you point to?
• Which of these blockers feel most likely for your organization right now? Options: Missing access/permissions, Poor data quality, CRM mapping ambiguity, No sandbox/test environment, Stakeholder misalignment, Email deliverability issues, Other
• Of those blockers, which one would you consider highest risk (pick one)? Options: Missing access/permissions, Poor data quality, CRM mapping ambiguity, No sandbox/test environment, Stakeholder misalignment, Email deliverability issues, Other
• Have you experienced a similar deployment failure before? Tell us what happened and how long recovery took.
• How would a failed initial deployment impact quarter goals and stakeholder confidence? Options: Major impact — jeopardizes quarter, Moderate impact — delays projects, Minor impact — manageable, Low impact

Is Your Data Fit for Launch?

• What percentage of records would you be comfortable launching with, knowing some optional fields might be missing? Options: > 95%, 80–95%, 60–80%, < 60%
• Do you have a recent sample data extract (5–10k rows) we can review for mapping and quality checks? Options: Yes — full sample available, Yes — limited sample, No — can be created, No — not available
• Which fields do you consider mandatory for the initial sync (select all that apply)? Options: Email, First name, Last name, Company, Job title, Lead status/stage, Lead source, Custom scoring fields, Other
• Estimate the percent of records with valid emails, company name, title, and a recent activity timestamp. Options: > 90%, 70–90%, 50–70%, < 50%
• Are there regulatory or residency constraints (GDPR, CCPA, data residency) that would restrict certain records from syncing? Options: Yes — GDPR, Yes — CCPA, Yes — other regional rules, No, Unsure — need to confirm
• Who is responsible for data remediation and de-duplication on your side? Options: CRM Admin, Revenue Ops, IT/Data Team, Third-party vendor, Other

Maps & Matchmaking: The Field-by-Field Reality

• If a mapping overwrite changed lead scores or stages for 5% of records, how quickly would you notice and who would raise the alarm?
• Do you already have a canonical field list and data dictionary we can align against? Options: Yes — fully documented, Partially documented, No — we can create one, No — not available
• How do you currently represent lifecycle and MQL→SQL transitions (pick one)? Options: Lead status field with picklist, Lifecycle stage field, Custom object/process, Handshake between systems, Other
• Which fields must never be overwritten by the integration (list key fields)?
• How do you want to validate mapping before full sync—sample records, dry-run, or shadow write? Options: Sample records review, Dry-run with logs, Shadow write to test field, Automated mapping preview, Other
• Who will make final approvals on field mapping changes? Options: CRM Admin, Revenue Ops Lead, Marketing Ops Director, VP Demand Gen, Other

Test Environments: Where Will We Break Things Safely?

• What's the cost or consequence if our test traffic accidentally reached production contacts?
• Do you have a sandbox/QA instance of the CRM and marketing stack available for testing? Options: Full sandbox available, Partial sandbox (some features), No sandbox — production only, Unsure/need to check
• Can we provision test email domains/subdomains and warm-up IPs in your environment? Options: Yes — we manage domains, Yes — vendor can provision, No — not allowed, Unsure
• Are there rate limits, throttles, or API usage windows that would affect testing? Options: Yes — strict limits, Yes — moderate limits, No limits, Unsure
• Do you allow synthetic contacts or test accounts that are flagged to prevent reporting pollution? Options: Yes — preferred, Yes — but limited, No — not allowed, Unsure
• Preferred windows for production-like testing (days/times)? Options: Business hours, Night/weekends, Specific maintenance windows, Flexible — mutually agreed

Rollback & Recovery: Do We Have a Plan B?

• If we needed to roll back the integration, how long would it take to restore your prior state? Options: < 1 hour, 1–4 hours, 4–24 hours, > 24 hours, Unsure
• Do you have backups/snapshots of CRM objects and critical datasets we can reference for recovery? Options: Yes — regular backups, Partial backups, No backups, Unsure
• Have you executed a rollback in the past 12 months? If so, what triggered it and what did you learn?
• What is the maximum acceptable data-loss or data-change threshold in a rollback scenario? Options: Zero tolerance, < 0.1% records, Up to 1% records, Up to 5% records, Depends on data
• Who has the authority to approve a rollback and who will lead the technical restoration?
• What communication channels and cadence should be used during an emergency rollback? Options: Slack/Teams + Email, Phone + Email, Incident management tool, Other

People, Training & Handoffs: Who Wins or Loses?

• If the launch is technically successful but your team doesn’t adopt the new workflows, what would that cost the organization?
• Which roles require hands-on training before go-live (select all that apply)? Options: Marketing Ops, Demand Gen, Sales reps, Sales Ops, CRM Admin, Finance/Analytics, Other
• Preferred training formats for your team? Options: Live workshops, Recorded videos, How-to playbooks, Office hours + Q&A, Train-the-trainer
• Who is the internal change champion that will drive adoption and what is their capacity to do so? Options: Full-time champion, Part-time champion, Shared responsibility, No clear champion yet
• What documentation, runbooks, or playbooks do you require at handoff? Options: Field mapping doc, Integration runbook, Troubleshooting guide, User training guides, All of the above, Other
• Who will own scoring calibration and scoring governance after the POC (role/title)? Options: Marketing Ops, RevOps, Data Team, Vendor/Consultant, Other

Mutual Commit: Acceptance, SLAs & Timeline

• If we miss one agreed acceptance criterion, do you prefer to pause the rollout or launch with mitigation controls? Options: Pause rollout, Launch with mitigations, Case-by-case decision, Unsure
• Please list the measurable acceptance criteria we must meet for POC success and production go-live (e.g., deliverability %, sync error rate, scoring accuracy).
• Which SLA items are non-negotiable for you? Options: Sync latency, Support response time, Data integrity threshold, Uptime for integrations, Security/compliance requirements, Other
• Who is the final go/no-go decision maker for the POC and who for full migration (role/title)? Options: Director of Marketing Ops, VP Demand Gen, CMO, Head of Revenue Ops, CRO, Other
• What are the target dates for: deployment start, validation complete, and full migration?
• What cadence of check-ins and status updates do you want during the deployment sprint? Options: Daily stand-ups, Twice-weekly, Weekly, As-needed

Close the Loop: Signals of Success & Next Steps

• What are the top three signals that will convince you this deployment is delivering value in the first 90 days?
• How will success be reported upward — dashboard, weekly executive summary, or ad-hoc calls? Options: Live dashboard, Weekly executive summary, Monthly business review, Ad-hoc reports, Other
• What would make you lose confidence in the deployment during the first 30 days? Options: High sync error rate, Broken lead handoff to sales, Deliverability drop, Data corruption, No visible pipeline impact, Other
• What is a manageable first step we can take together this week to move readiness forward? Options: Share sample extract, Schedule access handoff, Run mapping workshop, Provision sandbox accounts, Other
• Who should be on the 7–14 day tactical working group call from your side (role/title and email)?

Getting Comfortable — A Quick Intro

• Briefly tell us your role, team, and one sentence about what success looks like for you this quarter.
• How familiar is your team with modern marketing automation platforms? Options: Extremely familiar — we run complex automations, Some familiarity — we use basic automation, Minimal familiarity — mostly email blasts, No experience
• What’s the primary business reason pushing this evaluation right now? Options: Improve lead quality for sales, Get credible attribution to revenue, Replace fragmented email tools, Fix CRM data inconsistencies, Board / executive pressure, Other
• How urgent is solving this problem for your organization? Options: Immediate — within 2 weeks, Near-term — this quarter, Medium — next 2 quarters, Longer term — 6+ months, Unsure
• Who else on your side will be involved in discovery, POC approval, and technical sign-off? List roles or names if helpful.

If We Keep Doing What We're Doing…

• What is the real business cost if lead quality and attribution don’t materially improve by the end of the quarter? Options: Loss of pipeline growth, Missed revenue targets, Continued sales frustration, Budget reallocation risk, Executive escalation, Other
• How often do unqualified leads create rework for sales (e.g., rejecting, reassigning, or re-labelling leads)? Options: Daily, Several times a week, Weekly, Monthly, Rarely
• Share a recent example where a lead or campaign failure directly impacted a deal or campaign performance — what happened and why did it matter?
• How long has the team tolerated the current level of lead noise or attribution ambiguity? Options: Months, 1 year, Multiple years, It’s a recent issue, Unsure
• Which quick fixes have you tried and why did they fall short? Options: Manual list scrubbing, Simple scoring rules in CRM, Third-party integrations, Agency support, Nothing tried yet, Other

Where Data Breaks Down — Show Me the Evidence

• How confident are you that your CRM contact records correctly reflect engagement signals and fit today? Options: Very confident (90%+ accurate), Somewhat confident (70–90%), Low confidence (50–70%), Not confident (under 50%), No idea
• Do you have sample records or an exported dataset we can review for mapping and quality checks? Options: Yes — ready to share, Yes — need to extract, No — but can create, No — cannot share
• Which fields are most frequently missing or inconsistent in your CRM (pick all that apply)? Options: Email deliverability status, Job title / level, Company size/segment, Lead source / campaign, Engagement score, Lifecycle stage, Other
• What attribution model are you using now, and where do you see the biggest gaps? Options: First-touch, Last-touch, Multi-touch, Linear, We don’t have one / unsure, Other
• Tell us about the most recent CRM sync failure or mapping error — what data was lost or misattributed and what did you do to recover?

Who Actually Decides — And What They Care About

• If the CMO had to sign off today, what three measurable signals would make them say yes to a POC and rollout?
• Which stakeholders must be convinced for you to move forward (select all that apply)? Options: CMO / Marketing leader, VP Demand Gen, Head of Sales / CRO, Revenue Ops / RevOps, CFO / Finance, IT / Security, Other
• What are the executive-level deadlines or milestones driving this decision (e.g., board meeting, quarter-end reporting)? Options: Next 2 weeks, End of quarter, Next quarter, End of year, No hard deadline
• What metric or threshold would cause sales leadership to accept marketing-qualified leads as credible? Options: MQL→SQL conversion % (open), SQL→Opportunity conversion % (open), Lead response time < X hours, Lead score accuracy testing, Other
• Is finance asking for anything specific (e.g., multi-touch attribution to revenue) before approving spend? Options: Yes — multi-touch to closed revenue, Yes — pipeline impact forecast, No specific ask, Unsure

What Does Success Feel Like — Not Just Look Like

• Imagine it’s 90 days after launch — what behavior change in sales or marketing would prove this was worth doing?
• Which 3 KPIs would you use to prove POC success to executives? Options: MQL→SQL conversion uplift, Improved email deliverability rate, Lead-to-opportunity velocity, Attribution accuracy to revenue, Reduction in manual lead routing, Other
• What minimum numerical improvements would you accept for each KPI (please specify metric and target if possible)?
• Beyond numbers, what cultural or qualitative shifts would signal success (e.g., sales trusting marketing leads)? Options: Higher sales engagement with leads, Fewer lead-quality disputes, Marketing self-sufficiency, Clearer performance narratives for execs, Other
• If success starts to slip after initial rollout, what would be the single fastest corrective action you’d expect from a vendor? Options: Score model recalibration, Deliverability audit, Integration hotfix, Additional training, Pause and rollback, Other

The Proof That Will Make or Break This Deal

• What would make a POC feel like a definitive yes rather than a 'maybe later' — what single outcome would close the deal?
• Which POC acceptance criteria matter most to you (select top 3)? Options: Lead scoring accuracy vs baseline, CRM sync reliability and latency, Email deliverability improvement, Attribution mapping matches finance needs, Ease of building the tested workflow, Data quality improvements
• What minimum threshold would you accept for CRM sync reliability during the POC (e.g., 99% of records accurate within X minutes)? Options: >99% within 5 minutes, >99% within 1 hour, 95–99% within 1 hour, 85–95% / acceptable variance, Unsure — need vendor guidance
• Which live campaign would you be comfortable using for the POC (describe channel, audience size, and objective)?
• Who signs off on POC acceptance and what is their approval process? Options: Marketing leader, VP Demand Gen, Sales leader, RevOps / Data owner, Cross-functional committee, Other

Tech, Tools and the Hidden Dependencies

• Which single technical dependency would stop deployment cold if unresolved?
• Which CRM(s) and core systems must integrate with the platform (select all that apply)? Options: Salesforce, HubSpot, Microsoft Dynamics, NetSuite CRM, Custom CRM / API, No CRM / CSV only, Other
• Do you use middleware or an iPaaS (e.g., Mulesoft, Zapier, Workato) that will sit between systems? Options: Yes — enterprise iPaaS, Yes — light middleware, No middleware, Unsure
• Do you have a secure test environment and a data extract window we can use for mapping and trial runs? Options: Yes — ready, Yes — needs provisioning, No — will need to create, Unsure
• Are there security, compliance, or SSO requirements (e.g., SOC2, GDPR, MFA) that we must meet before going live? Options: SOC2, GDPR / Data residency, SSO/SAML, MFA, HIPAA, No special requirements, Other

People, Capacity, and Who Will Own It

• If you had unlimited vendor support for 30 days, what would you want your team to have accomplished by day 31?
• Who will be the day-to-day owner for the integration and for campaign ops after go-live? Options: Marketing Ops / RevOps, Demand Gen Manager, External agency, Shared / cross-functional, Vendor-managed initially, Other
• How many full-time equivalents (FTEs) can your team realistically allocate to implement and run the POC? Options: 0–0.5 FTE, 0.5–1 FTE, 1–2 FTEs, 2–4 FTEs, 4+ FTEs
• Where do you feel your team lacks skill or confidence (pick all that apply)? Options: Scoring model design, Deliverability best practices, Integration / data mapping, Building automation workflows, Attribution modeling, Change management
• What level of vendor involvement would make you comfortable during rollout? Options: Fully vendor-led until stable, Hybrid — vendor trains then handoff, Vendor guides; we execute, Self-serve with documentation

Risks, Deal-Stoppers, and Last-Minute Fears

• What’s the one risk that, if it occurred, would cause you to pause or cancel the project?
• How would you rate the likelihood and impact of the top three risks (choose impact scale)? Options: High likelihood / High impact, High likelihood / Medium impact, Low likelihood / High impact, Low likelihood / Low impact, Unsure
• Do you have a documented rollback or mitigation plan for integrations and campaign launches? Options: Yes — documented, Partial plan, No plan, Not sure
• What budget or procurement constraints could delay approval even if the POC meets acceptance criteria? Options: Fixed budget cycle, Need CFO approval, Procurement RFP process, No constraints, Other
• If an unexpected data/privacy issue emerged, who would we need to notify and what timeline would you expect for remediation?

Ready to Move — Next Steps & Timing

• Assuming we resolved the top three blockers today, how soon could you commit to a POC start date? Options: Immediately (this week), Within 2 weeks, Within a month, Next quarter, Unsure
• What approvals or signatures are required before starting a POC and who holds them?
• Which single campaign or audience would you prioritize for the POC (channel, list size, and goal)?
• What cadence and format do you prefer for check-ins during the POC (select all that apply)? Options: Weekly 30-minute calls, Bi-weekly demos, Daily stand-ups for first week, As-needed Slack channel, Email summaries only
• Who should we contact to schedule the initial technical kickoff and share a short list of required artifacts?