Getting Everyone on the Same Page

• Which stakeholders will you involve in evaluating a new DMS? Options: Dealer Principal / CEO, CFO / Finance, IT Director, Fixed Ops Director, General Manager, Controller, Parts Manager, Service Manager, Regional / Group VP, Other
• Who is the final decision maker who can sign off on a new DMS? Options: Dealer Principal / CEO, CFO, IT Director, Owner Group / Board, Regional VP, Collective committee, Other
• Who usually signs contracts for technology and services at your organization? Options: Dealer Principal / CEO, CFO / Controller, IT Director, General Manager, Outside counsel, Other
• How do the different stakeholders prefer to be engaged during evaluation? Options: One-on-one executive brief, Hands-on scenario demos, Technical deep-dive workshops, Group decision sessions, Reference calls / site visits, Written TCO and timelines, Other
• Share one sentence that would get each key stakeholder excited about evaluating a new DMS (dealer principal, CFO, IT).
• Are there current vendor or OEM relationships that will need approval or notification as part of this evaluation? Options: Yes — OEM rep, Yes — current DMS vendor, Yes — finance partners, No, Unsure

Who's Really Calling the Shots?

• Which stakeholder could quietly kill this project if they believed the risk outweighed the gain? Options: Dealer Principal / CEO, CFO, IT Director, Fixed Ops Director, Controller, Other
• Which three roles have the most influence over the technical acceptance criteria? Options: Dealer Principal / CEO, CFO, IT Director, Fixed Ops Director, Service Manager, Parts Manager, Controller, Regional / Group VP, Other
• For each highly influential stakeholder, what is their single biggest concern about switching DMS?
• How aligned are stakeholders on the tradeoff between budget and business disruption? Options: We prioritize minimizing disruption over cost, We prioritize cost over disruption, Balanced — both matter equally, No clear alignment
• Has any influential stakeholder led a previous DMS or major systems change? What was the outcome?

What Keeps Your Team Up at Night?

• When DMS issues happen on a busy day, who takes the heat — and why does that matter to the project? Options: Dealer Principal / CEO, CFO / Controller, IT Director, Fixed Ops Director, Service Manager, Other
• Which failure modes are most damaging to your business today? Options: System downtime, Data loss / corruption, Incorrect OEM reporting, Failed integrations (CRM, lenders), Billing / invoicing errors, Open RO visibility loss, Other
• How often do those failure modes occur today? Options: Daily, Weekly, Monthly, Quarterly, Rarely / Never
• Describe a recent incident that caused measurable business impact (revenue, customer experience, OEM penalties).
• Which teams feel the operational pain most acutely when the DMS fails? Options: Sales / Desking, F&I, Parts, Service, Accounting / Finance, IT / Integrations, Other
• What is the maximum acceptable downtime during business hours for you to still consider a deployment successful? Options: Minutes (under 30), 1–2 hours, Same-day recovery, Up to 24 hours, Longer — business closes

Are We Comfortable with the Rules?

• What's the policy, compliance requirement, or OEM rule you would never relax—even if it increased cost or timeline?
• Which non-negotiables must the new DMS meet before you will accept it? Options: OEM certification/compliance, Migration within approved window, Data residency or retention, PCI / payment security, SOC2 / ISO standards, SSO / SAML integration, Audit trails & reporting, Other
• Are specific OEM certifications, factory tools, or manufacturer portals mandatory on day one? Options: Yes — specific OEM tools required, Yes — OEM reporting only, No immediate OEM requirement, Unsure — need to verify
• Do any existing contracts, manufacturer warranties, or finance provider terms constrain timing or vendor choice? Options: Yes — manufacturer contract, Yes — finance partner agreement, Yes — other vendor contract, No, Unsure
• What internal IT or security policies would force changes to our standard implementation approach? Options: Strict firewall policies, Restricted outbound connections, SAML/SSO requirements, Vendor penetration testing required, Data encryption mandates, Other
• Under what circumstances would you consider revising a current non-negotiable?

If Success Had a Meter, What Would It Read?

• If we judged success after 12 months on one number, which metric would you choose? Options: Uptime percentage, Migration window length, Net financial ROI, Reduction in manual processes, Faster close-to-cash, User satisfaction / adoption, OEM compliance score, Other
• Which three success signals matter most to you? Options: Uptime / reliability, Short cutover window, Positive ROI, Fewer support tickets, Faster service throughput, Accurate OEM reporting, Cleaner financials / GL reconciliation, Other
• What target uptime percentage would you require for acceptance? Options: 99.99%, 99.9%, 99.5%, 99%, Other / Not sure
• How do you define a successful cutover from a business perspective (no revenue loss, no OEM penalties, full transactional capability)?
• Who will own ongoing success metrics after go-live (tracking and sign-off)? Options: IT / Technical Owner, CFO / Finance, Fixed Ops Director / Ops, Vendor (us) with shared SLA, Third-party success manager, Other

How Will We Move the Data Without a Headache?

• What about your data migration feels most risky to you today?
• Which source DMS platforms and versions are we migrating from? Options: Vendor A, Vendor B, Vendor C, Custom/legacy, Multiple vendor environments, Unsure / need inventory, Other
• How many years of historical data must be transferred (sales, parts history, RO, GL)? Options: Full history (all years), Last 7+ years, Last 3–5 years, Last 1–2 years, Only current balances / open items
• Which data domains are highest priority for go-live? Options: Customer records, Vehicle VIN history, Open repair orders, Parts inventory & pricing, F&I contracts, General ledger balances, Payroll data, Other
• Describe the primary data quality issues we should expect (duplicates, missing VINs, mismatched vendor codes, historical mapping gaps).
• Do you require a full parallel-run reconciliation, spot checks, or a phased data verification approach before cutover? Options: Full parallel run, Sampled reconciliation, Phased verification by module, Trust & validate post-cutover, Unsure — need recommendation

Politics, People, and the Quiet Objections

• Who inside the organization might prefer the status quo, and what influence do they have?
• Have any internal stakeholders already expressed explicit objections? What are those objections?
• Are there external partners or vendors (lenders, CRM, marketing, OEM reps) who could create resistance to switching? Options: Lender / finance partner, CRM provider, Digital retailing vendor, OEM rep, Parts vendor, No known conflicts, Unsure
• How do you plan to communicate the change to staff to minimize friction? Options: Executive announcement, Department meetings, Hands-on training sessions, Train‑the‑trainer model, Pilot group rollout, Regular email updates, Other
• What training cadence, format, and duration will be required for your teams to reach confidence? Options: Intensive on-site week, Phased classroom + eLearning, Train-the-trainer with follow-ups, On-demand microlearning only, Combination
• Who will be the internal project sponsor and who will be the day-to-day project manager? Options: Dealer Principal / Sponsor, CFO / Sponsor, IT Director / PM, Fixed Ops Director / PM, External consultant / PM, Other

Timeline, Investment, and Decision Confidence

• If someone asked you today whether you could comfortably sign a contract in 60 days, what would keep you from saying yes?
• What is your target go-live timeframe? Options: Within 1–2 months, 3–6 months, 6–12 months, 12+ months, No firm timeline
• What budget range have you allocated for license, migration, and implementation services? Options: Under $100k, $100k–$250k, $250k–$500k, $500k–$1M, Over $1M, Undetermined
• Which commercial terms matter most to you when choosing a DMS vendor? Options: Term length (contract years), Transparent per-user pricing, Data migration included, SLA and uptime guarantees, Exit / data portability terms, OEM certification included, Other
• What contract or legal terms would be a deal-breaker for you?
• How confident are you in your internal approval process to meet your target timeline? Options: Very confident, Somewhat confident, Unsure, Not confident

If We Only Did One Thing Next, What Would It Be?

• Which next step would unlock decisions fastest for you? Options: Executive scenario demo, Hands-on workshop with workflows, Reference visit to a similar dealer group, Detailed TCO and timeline, Pilot migration of a data slice, Legal & commercial draft review
• Who must attend the next meeting from your side to make progress? Options: Dealer Principal / CEO, CFO / Controller, IT Director, Fixed Ops Director, Service Manager, Parts Manager, Other
• What evidence, deliverable, or outcome would change a 'maybe' to a 'yes' for your stakeholders?
• When can we schedule the next check-in to address remaining gaps? Options: Within 1 week, Within 2 weeks, Within 1 month, Other — propose a date
• Is there anything critical we haven't surfaced that would materially affect scope, timeline, or decision?

Quick Check: Who's in the Room?

• Who are the people we should interview or include when we map your current DMS workflows (name, role—e.g., dealer principal, CFO, IT lead, fixed ops manager)?
• Which of these decision roles currently sign off on DMS changes, budgets, or go-live timelines? Options: Dealer Principal / CEO, CFO / Finance Director, IT Director / CTO, Fixed Ops Director, General Manager, Parts Manager, F&I Manager, Other
• What’s the single biggest constraint on scheduling discovery interviews with your team (time, access to systems, stakeholder availability, OEM reporting blackout windows, other)? Options: Executive availability, Shop/rush schedules, Lack of admin credentials, OEM timing windows, Other
• Is there an internal owner we should treat as the primary contact for questions and approvals during mapping?

Where Your System Actually Earns Its Keep

• If you had to pick one workflow where the DMS must be flawless to protect revenue, which would it be and why? Options: Sales/desking, F&I contracting, Parts ordering/fulfillment, Service repair order flow, Accounting/GL posting, Other
• Walk me through your typical sales-to-funding flow from customer lead to lender funding—where are manual handoffs or re-entries required?
• Describe how an RO (repair order) is created, dispatched, and billed today—who touches it and where do exceptions occur?
• Which workflows currently require someone to 'fix' data before the next step can proceed (examples: VIN corrections, contract re-entries, parts substitutions)?
• How often do you run parallel or manual reconciliations for revenue, parts, or F&I each month? Options: Daily, Weekly, Monthly, Quarterly, Ad hoc / only when issues arise

The Quiet Failures That Cost You

• What recurring DMS failures have you learned to tolerate because ‘that’s just how it is’—and how much do those failures actually cost you (time, lost deals, fines)?
• Which of the following failure modes happen in your environment (select all that apply)? Options: Data sync delays, Duplicate customer or vehicle records, Contracts not transmitted to OEM/lender, Parts orders lost or duplicated, GL posting mismatches, System downtime/unavailable during peak hours
• When a failure occurs, how long does it typically take to detect and then to resolve? Options: <1 hour, 1–4 hours, 4–24 hours, 1–3 days, Several days or longer
• Share a recent example of a failure that had an outsized impact—what happened, who was involved, and what was the business outcome?
• How often do failures trigger manual workarounds that bypass standard controls (e.g., spreadsheet fixes, paper contracts, off-system payments)? Options: Daily, Weekly, Monthly, Rarely, Never

Who Owns the Mess When Things Break?

• When something breaks in the DMS, who is the first person or team staff call—and are they empowered to resolve it? Options: In-house IT, DMS vendor support, Third-party integrator, Store manager, Other
• Describe your escalation path for critical issues (who gets notified at 1 hour, 4 hours, 24 hours) and whether SLAs exist.
• Which service model do you currently have for vendor support—reactive ticketing, dedicated technical account manager, 24/7 support, or none? Options: Reactive ticketing, Dedicated TAM, 24/7 on-call, Business-hours only, None / ad hoc
• How confident are you that the person on call can fix issues that impact OEM compliance or lender transmission within your required windows? Options: Very confident, Somewhat confident, Not confident, Unsure
• What internal consequences happen when downtime or data failures occur (e.g., overtime pay, lost F&I deals, delayed funding, fines)?

Data — How Clean Is It, Really?

• If I asked your CFO whether the data in the DMS is trustworthy for month-end reporting, what would they say and why? Options: Yes—fully trusted, Mostly trusted with manual adjustments, Not trusted, Unsure
• Which datasets cause the most pain during reconciliation or reporting (select all that apply)? Options: Customer records, Vehicle VIN/inventory, Sales contracts and funding, F&I product booking, Parts inventory, Repair orders / labor hours, General ledger
• How often do you find duplicate customer records, mismatched VINs, or orphaned transactions—and what process currently resolves them? Options: Daily, Weekly, Monthly, Rarely, Never
• When you extract data for reporting, what percentage of fields typically require manual correction or transformation before use? Options: <5%, 5–15%, 15–30%, 30–50%, >50%
• Are there legal, OEM, or audit requirements tied to data retention, formatting, or access that we must honor during mapping and migration? Options: Yes—OEM compliance, Yes—auditor/tax rules, Yes—privacy/regulatory, No specific requirements, Unsure

Integration Web: What’s Plugged In and What’s Fragile?

• Which external systems are currently integrated with the DMS (select all that apply)? Options: OEM portals, Lender / funding engines, CRM / lead providers, Digital retailing platform, Parts vendors / distributors, Payroll/HR, Accounting / ERP, Aftermarket vendors, None / not sure
• What interface types do those integrations use—API, SFTP, EDI, proprietary middleware, file drops—and which feel most brittle? Options: API, SFTP/FTPS, EDI, Proprietary connector, Flat-file import/export, Manual copy/paste, Other
• Tell us about a time an integration failed—how was it detected, how long did it take to restore, and what was the business impact?
• Who owns monitoring and validation for integrations (internal ops, IT, vendor, third-party integrator)? Options: Internal IT, Business ops team, DMS vendor, Third-party integrator, No one / ad hoc
• Which integrations would you consider non-negotiable in a migration (e.g., OEM certified connections, lender integrations, payroll)?

Cost and Rhythm: Where Are You Paying the Most?

• Beyond subscription fees, where do you see the largest, recurring operational costs tied to the DMS (select all that apply)? Options: Staff time for reconciliations, Third-party integration fees, Per-user licenses, Overtime due to outages, Audit and compliance remediation, Data conversion services, Other
• How much time (approx. hours per week) does your team spend fixing DMS-related exceptions or working around system limits? Options: <5 hours, 5–15 hours, 15–40 hours, 40–80 hours, >80 hours
• Do you have a clear monthly or annual number for total cost of ownership (TCO) for your current DMS, including internal headcount and third-party fees? Options: Yes—detailed TCO, High-level estimate, No, but we could produce one, No/unknown
• Which workflows, if automated or fixed, would meaningfully reduce headcount or overtime?
• Are there contract terms or vendor fees that would complicate a migration timeline (early termination penalties, certification costs, or mandatory transition windows)? Options: Yes—penalties/fees, Yes—OEM certification timing, No major constraints, Unsure

If We Were to Rebuild This — What Must Survive?

• Which existing features, reports, or customizations could we not remove without disrupting operations?
• Are there OEM or lender certifications, compliance checks, or reporting formats that are non-negotiable for cutover acceptance? Options: OEM reporting/certification, Lender/funding certs, Tax/audit reporting, Custom dealer reports, Other
• Which data sets must be migrated with 100% fidelity (e.g., active contracts, current inventory, open ROs) versus those acceptable to archive or transform? Options: Active contracts, Current inventory, Open ROs/estimates, Customer contact history, Historical GL entries, Other
• What are your absolute no-go windows for cutover or heavy system changes (months, OEM blackout periods, month-end, year-end)?
• If we could guarantee one thing about a new system on day one, what would make you comfortable to move forward (example: no downtime during funding windows, 99.9% data match for open deals)?

Small Wins & First Steps — Where Should We Prove Value?

• If we fixed one recurring pain in 30 days, which problem would deliver the most business value or confidence for your leadership? Options: Faster lender transmissions, Cleaner inventory/VIN accuracy, Reduced parts order errors, Less time on month-close, More reliable service scheduling
• Who are the internal champions and skeptics we should engage early to pilot a fix or quick win?
• What data access and credentials can you provide us for discovery and pilot work—read-only accounts, test environment, or production admin? Options: Read-only production, Production admin, Test/staging environment, No access currently available, Other
• How quickly could your team commit to a 4–6 week pilot that validates one core workflow end-to-end? Options: Immediately, Within 1 month, 1–3 months, Longer than 3 months, Unsure
• What would success look like for that pilot—define measurable signals (examples: X% reduction in manual fixes, 0 missed lender deliveries, Y hours saved/week)?

Set the Stage: Your Cutover Horizon

• What target date or window are you aiming for to go live with the new DMS? Options: Specific date (MM/DD/YYYY), Two-week window, Month range, Quarter, TBD
• What internal or external deadlines are forcing that timing (e.g., OEM reporting cutoffs, fiscal close, franchise commitments)?
• Which days or times are absolute no-go’s for cutover (service peak days, payroll, major OEM pushes, key store events)? Options: Weekday business hours, End-of-month, Weekend, Holiday periods, Model release weeks, Other
• How much lead time do you need between final data freeze and the cutover execution? Options: Same day, 24 hours, 48–72 hours, A week, Depends on scope
• Who needs final calendar approval for the cutover date (name and role)?

If We Missed the Window, What Breaks?

• If the cutover slips by a week, what immediate business outcomes are at risk—sales, lender funding, OEM reporting, payroll, parts ordering? Options: Vehicle deliveries, Lender funding, OEM compliance, Payroll, Parts procurement, Service scheduling, Other
• Which of those risks would cause you to escalate to the executive team immediately? Options: Lender funding delays, OEM non-compliance, Payroll errors, Inability to process retail deals, Major parts supply issues, Other
• How much downtime (scheduled or unscheduled) is tolerable during cutover for each critical area—Sales, F&I, Parts, Service, Accounting? Options: None/zero tolerance, Under 1 hour, 1–4 hours, 4–8 hours, Up to 24 hours
• Describe a previous go-live or migration that didn’t go as planned—what happened and what lesson should we apply here?

Who Owns This? — Roles, Availability, and Decision Rights

• Who is the single owner (name and role) accountable for declaring go/no-go on cutover day?
• Beyond that owner, who are the 3–5 critical on-the-ground contacts we must reach during cutover (Dealer Principal, CFO, Fixed Ops Director, IT lead, Store Manager)? Options: Dealer Principal/CEO, CFO, IT Director, Fixed Ops Director, General Manager, Store Manager, Other
• What are the escalation channels and hours of availability for each contact during the cutover (phone, SMS, email, after-hours)? Options: Phone (call), SMS/text, Email, Messaging app (Slack/Teams), On-site only, Other
• Who is authorized to approve emergency changes or scope reductions during cutover, and what is the approval turnaround time expected?
• Which roles will be on-site versus remote during the cutover? Options: On-site, Remote, Hybrid (some days on-site)

Is Your Data Really Ready to Move?

• If someone looked at your current DMS data today, how confident would you be that the customer, inventory, and accounting data are complete and accurate? Options: Very confident, Mostly confident, Some gaps expected, Significant issues likely
• Which datasets are already scoped and mapped for migration (select all that apply)? Options: Customers/CPAs, Deal and contract data, Vehicle inventory, Parts inventory, Service history/ROs, General ledger, Payroll, OEM/submissions
• Have sample exports been shared with our migration team? If yes, which tables/files and when were they last extracted? Options: Yes—full extracts, Yes—partial/sample, Planned but not yet provided, No extracts available
• Are there known data quality issues we must remediate before migration (duplicates, missing VINs, incorrect GL mapping)? Please list and indicate impact.
• Do you have any special data-handling rules (masking PII, retaining audit logs, vendor-specific formats) we must honor? Options: PII masking, Retention policies, Audit trail preservation, Vendor-specific formatting, Other/None

Can We Rehearse Without Breaking Anything?

• How often do you run dress-rehearsals for major IT changes, and what usually goes wrong in those rehearsals? Options: Weekly, Monthly, Quarterly, Rarely/Never, Never
• Do you have a dedicated test environment that mirrors production (data volume, integrations, user roles)? Options: Full mirror of production, Partial mirror, Limited test environment, No test environment
• Who will own User Acceptance Testing (UAT) for each business stream—Sales, F&I, Parts, Service, Accounting—and how will success be measured?
• What representative test scenarios must pass before go-live (e.g., retail deal through funding, F&I contracting, parts reorder, RO close to GL)? List top 6 priority scenarios.
• How many named users will participate in UAT and do they need training or runbooks beforehand? Options: 1–5, 6–15, 16–50, 50+

All the Integrations — Are They Actually Connected?

• If an integration failed the day after cutover, which failure would be most damaging—OEM feed, lender interface, CRM, digital retailing, parts vendor? Options: OEM feed, Lender funding, CRM integration, Digital retailing, Parts vendor, Payroll/GL
• Please list the critical third-party systems we must validate pre-cutover and their current status (Connected / Credentialed / Needs Approval): CRM, OEM APIs, Lenders, Payment Processors, Parts Vendors.
• Which integrations require vendor coordination or certification from the OEM or third parties before live transactions are allowed? Options: OEM certification, Lender certification, Payment gateway certification, Third-party API keys, None
• Do you have test credentials and a contact at each vendor who can support integration testing during our windows? Options: All test credentials available, Some available, Planned but not ready, Not available
• How do you prefer we validate integrations during cutover—parallel run, phased redirect, or immediate switch-over? Options: Parallel run (preferred), Phased redirect by module, Immediate switch-over, Hybrid approach

Security, Access, and Who Gets the Keys

• Who will be the security approver for accounts, roles, and access changes during cutover?
• What authentication methods are required in production (SSO, MFA, LDAP, local accounts) and which of these must be in place before go-live? Options: SSO/SAML, MFA, LDAP/AD Sync, Local accounts, VPN only, Other
• Are there firewall, VPN, or network change windows we must book with your IT or hosting provider ahead of cutover? Options: Yes—booked, Yes—not booked, No changes needed, Unsure
• Do you require penetration testing, vulnerability scans, or security attestations before we enable live connections to OEMs and lenders? Options: Pen test required, Vulnerability scan required, Attestation/Checklist only, No additional tests required
• What logging, monitoring, and audit expectations do you have for the first 30 days after cutover?

Plan B: If Things Go Sideways

• Do you have an existing rollback plan for this kind of migration and how quickly can you restore the previous environment if needed? Options: Full rollback in hours, Rollback in 24 hours, Rollback in 48+ hours, No rollback plan
• Which data snapshots and backups must be captured immediately before cutover (full DB, transactional logs, file system)? Options: Full DB snapshot, Transaction/log backups, File system backup, Configuration exports, Other
• If critical integrations fail, what manual workarounds are acceptable to keep the business running (e.g., manual lender submission, parts phone orders)?
• What internal communication templates or external customer/vendor notices must be ready in case we delay or rollback? Options: Customer-facing notice, Vendor notice, Internal escalation template, None
• Who is responsible for declaring a rollback and who must agree before it executes?

Acceptance: What 'Done' Actually Looks Like

• What are the non-negotiable acceptance criteria for a successful cutover (data integrity %, transaction success %, reconciliation completeness)?
• Which business owners must sign acceptance and how will that sign-off be captured (email, e-signature, ticket closure)? Options: Email confirmation, E-signature, Ticket system closure, Formal sign-off document
• How long is the hypercare monitoring window post-cutover and which SLAs apply during that period? Options: 24–48 hours, 3–7 days, 2–4 weeks, Custom SLA
• What reconciliation and validation tasks do you expect immediately after cutover (e.g., open deals, vendor invoices, GL trial balance)?
• If acceptance criteria are not met, what is the agreed remediation path and who owns it?

Final Pulse: Are We Ready to Declare Go?

• Based on the items above, how would you rate your overall readiness to proceed with the planned cutover? Options: Ready—green, Caution—some gaps, Not ready—major blockers, Undecided/need more info
• List the top three outstanding blockers that must be cleared before we can confirm the cutover date.
• What would be a practical next step from your side this week to move readiness forward (provide extracts, approve schedule, assign UAT users)? Options: Provide data extracts, Approve cutover schedule, Assign UAT users, Confirm vendor contacts, Security approvals
• Choose a preferred time for a final readiness review call with our delivery team (include timezone). Options: Within 48 hours, This week, Next week, After blockers cleared
• Anything else we haven’t asked that keeps you up at night about this migration?

Start: Tell Us About Your Dealership Group

• How many rooftops/stores are in your organization right now? Options: Single store, 2–5 stores, 6–20 stores, 21–50 stores, 51+ stores
• What’s the legal or trading name we should use for this project (dealer group or store name)?
• Which DMS are you currently running today? Options: CDK, Dealertrack/DMS (ADP), Reynolds & Reynolds, DealerBuilt, Auto/Mate, Other — please specify
• How is your DMS hosted today? Options: On-premise (local servers), Cloud-hosted by current vendor, Hybrid, Unsure
• Roughly how many active users access the DMS regularly (FTE equivalents)? Options: 1–10, 11–25, 26–75, 76–200, 200+

Are You Comfortable Running on a Best-Guess?

• When something in the DMS goes wrong, who usually hears about it first—and how does that conversation start? Options: Service desk/IT, Fixed Ops manager, Store manager/GM, CFO/Controller, Other
• How often do you experience DMS outages, slowdowns, or critical integration failures that interrupt transactions? Options: Daily, Weekly, Monthly, A few times a year, Rarely/Never
• What data or integration gaps are you most worried about right now (select all that apply)? Options: OEM reporting/communications, Lender integrations, CRM sync, Inventory feeds, Parts vendor integrations, Payroll/GL sync, Other
• Tell us about a recent incident that exposed an unknown or unreliable piece of data—what happened and what was the fallout?
• How much tolerance does your leadership team have for transactional errors during peak windows (e.g., nights/weekends, month-end)? Options: None—must be zero, Very low—minor acceptable, Moderate—some disruption tolerable, Flexible
• Who owns your master data (customer, vehicle/VIN, parts) today, and how is ownership enforced? Options: IT, Fixed Ops/Parts, Sales operations, Finance/Controller, Shared governance, No clear owner

Who's Quietly Paying the Price?

• Which department spends the most time compensating for DMS gaps (manual work, spreadsheets, calls)? Options: Sales/Desking, F&I, Parts, Service/RO, Accounting/Finance, IT/Support
• Approximately how many staff-hours per week are spent on manual workarounds tied to the DMS? Options: Under 10 hours, 10–40 hours, 41–100 hours, 100+ hours, Don’t know
• What recurring error or reconciliation eats the most time or margin for your business?
• Have integration failures ever caused lost deals, missed manufacturer incentives, or lender rejections? Tell us an example.
• Which financial line items do you suspect are being impacted by your current DMS issues (choose all that apply)? Options: Gross Profit on Vehicles, F&I income, Parts margin, Service labor capture, Manufacturer chargebacks/penalties, Payroll errors, Other
• How do these recurring problems make key stakeholders (owner, CFO, fixed-ops lead) feel about the current technology? Options: Frustrated/angry, Worried/cautious, Tolerant/apathetic, Optimistic about change, Other

If You Could Snap Your Fingers and Fix Three Things

• Which three outcomes would make you say a new DMS was a clear win? (rank or list) Options: 99.9% uptime, Migration in a single weekend, No disruption to OEM reporting, Integrated CRM & inventory, Reduced manual reconciliations, Faster month-end close, Other — specify
• What measurable success signals will the dealer principal, CFO, and IT director each demand before they approve a go-live?
• What is your target maximum cutover window (the total time you can tolerate for migration/cutover)? Options: One business day, Weekend (48 hours), Multi-day (3–5 days), Phased with parallel runs, Flexible/unsure
• Over what timeframe must the platform demonstrate ROI for the CFO to consider the investment justified? Options: Under 6 months, 6–12 months, 1–2 years, 2+ years, Not sure
• What would you consider non-negotiable acceptance criteria on day one of go-live?

Show Me You Can Handle Our Mess: Workflows & Integrations

• Which customer-facing workflows absolutely must be demoed using your real processes (pick all that apply)? Options: Sales desking/quote-to-cash, F&I contracting and funding, Parts sales/POS, Service scheduling and RO, Trade appraisal and VIN transfer, Other
• List the third-party systems you currently integrate with that cannot be disrupted (CRM, digital retailing, lenders, OEM portals, payments).
• How many historical transactions and which data domains must be migrated (customers, vehicles, contracts, parts inventory, GL)? Options: <1 year, 1–3 years, 3–7 years, All historical data, Unsure
• Which integrations require certified connections or OEM attestations on day one? Options: OEM factory communications, Lender decisioning/funding, Manufacturer warranty systems, Third-party payment processors, Payroll providers, None
• What real-world scenario should we run together to prove fit—for example: a high-volume F&I funding day or parts physical inventory reconciliation?
• What validation metrics would convince IT that integrations are healthy (e.g., latency thresholds, sync success rates)?

Who Will Carry the Baton When Things Get Messy?

• Who will be the executive sponsor for this project from your side? Options: Dealer Principal/CEO, CFO/Controller, VP Fixed Ops, IT Director, Other
• Which roles should we expect to be on the day-to-day project team (select all that apply)? Options: Project Manager, IT Admin, Parts Lead, Service Manager, Sales Manager, F&I Manager, Accounting Lead
• Who is authorized to sign readiness and cutover approvals when the checklist is complete?
• What internal change-management constraints do we need to respect (training windows, union rules, OEM training/credentials)?
• How do you prefer training to be delivered for each role (choose all that apply)? Options: Instructor-led onsite, Remote live sessions, Self-paced eLearning, Role-based shadowing, Documentation only
• Who will own post-go-live support and first-line triage at each store? Options: Local store manager, Dedicated super-user, Regional support team, Internal IT, Vendor support

What Would Make Us Say Yes Today? Commercials, Risk, and Must-Haves

• What are the non-negotiables that would immediately disqualify a vendor from consideration? Options: No OEM certification, Insufficient data migration plan, No SLA for uptime, No on-site training option, Contract terms unacceptable, Other
• What length of commercial term do you realistically prefer for a significant system like this? Options: 1 year, 3 years, 5 years, 7+ years, Unsure
• Which SLA targets are table stakes for you (choose up to three)? Options: 99.9% availability, 4-hour critical incident response, 24/7 support, Monthly performance reports, Certified OEM support
• Are there specific compliance or certification requirements we must meet (manufacturer, finance, PCI, SOC2, ISO)? Please list.
• What pricing model do you prefer or must the vendor support? Options: Per-user per-month, Per-store flat fee, Transaction-based, Tiered modules, Capital purchase + maintenance, Other
• What are the top commercial risks your CFO worries about with a DMS change?

What's One Small Step That Proves Momentum?

• Which pilot scope would demonstrate value quickly for your leadership (single store, department pilot, phased go-live)? Options: Single store pilot, Fixed Ops pilot only, Sales & F&I pilot, Phased multi-store roll, Full cutover
• What is your ideal timeline for a pilot and a full roll (pick ranges)? Options: Pilot within 30 days, Pilot in 30–90 days, Pilot in 90–180 days, Longer/strategic timeline
• What would a minimally viable acceptance test look like for the pilot (list specific transactions or reports)?
• What rollback or contingency plans do you require to feel safe during pilot or cutover?
• Who should be on the weekly steering calls while we run the pilot and prepare cutover? Options: Sponsor (Dealer Principal), CFO/Controller, IT Director, Project Manager, Vendor PM
• What stakeholder concerns would need to be addressed in the first pilot update to keep momentum?