Quick introductions — who’s actually in the room?

• Who will be our primary contact during discovery and decision-making? (name, role, email)
• Which functions are represented in today’s stakeholder group? Options: Finance / Accounting, IT / Infrastructure, Procurement, Manufacturing / Operations, Supply Chain / Logistics, HR / Payroll, Legal / Compliance, Systems Integrator / SI, Other
• Who is the executive sponsor with final budget authority for this initiative? Options: CFO, CIO, COO, CEO, Board / Investment Committee, Other
• Does the sponsor have an assigned delegate who can make day-to-day decisions during implementation? Options: Yes — named delegate, Yes — role-based delegate (e.g., VP Finance), No, Unsure
• What is your current relationship with our certified systems integrators? Options: We have selected an SI and engaged them, We have preferred SI candidates, We have no SI selected yet, We will use internal resources only, Other

If this project fails, who gets held accountable?

• When deadlines slip or unexpected costs appear, who in your organization typically owns the fallout? Options: CFO, CIO, VP Finance, VP IT, Program / PMO lead, Business unit leader, Other
• What formal decision rights exist today for trade-offs between scope, timeline, and budget?
• Are there formal veto gates we must plan for (finance committee, IT security board, legal approval)? If so, which? Options: Finance committee, IT / Security board, Legal / Procurement sign-off, Executive steering committee, No formal veto gates, Unsure
• How were past ERP or major systems projects governed — what worked, and what repeatedly caused problems?
• If a conflict arises between finance and IT during cutover, what escalation path will resolve it? Options: Executive sponsor decision, Steering committee vote, Predefined RACI / sign-off matrix, External arbitrator (vendor/SI), Other

What keeps you up at night about data and cutover?

• Which of the following risks would cause you to pause or stop a cutover on day zero? Options: Data migration accuracy, Transactional data loss, Business downtime / production stoppage, Compliance / audit breach, User adoption failure, SI delivery failure, Budget overrun, Other
• Can you describe a recent incident where a migration, integration, or cutover caused disruption? What happened and how long did recovery take?
• What tolerance for reconciliation variance will you accept immediately post-cutover (choose the closest) Options: Zero tolerance — must match exactly, < 0.1% variance, 0.1%–1% variance, > 1% acceptable short-term, Unsure
• Which source systems or data domains are the single source of truth and must be treated as ground truth during migration? Options: General Ledger / Financials, AR / AP subledgers, Inventory / WMS, Payroll / HR, Manufacturing systems (MES/PLM), CRM / Sales, Other
• Do you already have reconciliation scripts, test cases, or acceptance reports that our migration must pass? Options: Yes — comprehensive suite exists, Partial scripts / reports available, No, we need help creating them, Unsure

Are your timelines aspirational or negotiable?

• What target go-live window are you aiming for (date, quarter, or fiscal milestone)? Is that date immovable?
• Are there immovable deadlines driving the timeline (e.g., end-of-support, regulatory reporting, acquisition close)? Please select all that apply. Options: Incumbent ERP end-of-support, Regulatory / statutory reporting deadline, Acquisition / integration legal close, Fiscal year close / audit, Business restructure or board mandate, None of the above, Other
• Would you prefer a phased deployment that secures financials first even if full enterprise rollout shifts later? Options: Prioritize financials / phased approach, Prefer a big-bang enterprise cutover, Open to phased if clear ROI, Undecided
• Which internal approval cycles typically add time (procurement, security review, budget committee)? Select all that apply. Options: Procurement approval, IT security review, Architecture / IT change board, Budget committee / finance sign-off, Legal / compliance review, HR / privacy review, None / fast-track
• How much buffer would you like between final testing sign-off and actual cutover? Options: 0–2 weeks, 2–4 weeks, 1–3 months, 3+ months, Unsure

How will we know — and prove — that this was a success?

• What are the top three measurable outcomes that will convince your executive sponsor this project succeeded?
• Which of these KPIs would you expect to improve within 6 months post-go-live? (select all that apply) Options: Consolidated close days, Number of manual journal entries, Time spent on reconciliations, Invoice-to-payment cycle time, Inventory accuracy / shrinkage, Order-to-cash cycle time, Payroll accuracy / exceptions, Other
• What formal acceptance criteria will trigger a go/no-go decision for a phase cutover? Select all that apply. Options: All critical reconciliations pass within tolerance, Automated close achieves target timeline, Key integrations validated end-to-end, No high-severity defects outstanding, Process owner or user sign-off, Other
• Who (by role) will sign the formal acceptance for each phase cutover? Options: CFO, VP Finance, CIO, VP IT, Process owner (finance), Process owner (operations), SI Program Manager, Steering Committee
• If early metrics fall short of targets, what remediation window would you allow before considering roll-back or escalation? Options: 0–14 days, 2–8 weeks, 1–3 months, 3+ months, Depends on the KPI / issue, Unsure

Which integrations or reports would trigger an all-hands alarm if they fail?

• List the top five integrations or reports that must work on day one (e.g., payroll feed, bank reconciliation, MES inventory updates).
• Which customizations or reconciliations in your current ERP are non-negotiable to preserve or replicate?
• Which interfaces require real-time processing versus batch updates after cutover? Options: Real-time only, Batch only, Some real-time / some batch (hybrid), Unsure — need to review each
• Who currently owns each critical integration or report, and who will be responsible after cutover? (list owners and backup owners)
• Are there audit, regulatory, or retention requirements for logs and data that must be preserved verbatim? Options: Yes — full preservation required, Partial retention acceptable, No special retention requirements, Unsure — need legal input

Who needs to be won over — and what will actually move them?

• Which user groups are most likely to resist this change and why (practical examples please)? Options: Finance accountants / close team, FP&A, Procurement, Shop floor / operations, Field service / technicians, HR / Payroll, Sales / Order entry, Other
• What training formats and change practices have historically driven the best adoption in your organization? Options: Instructor-led classroom, Virtual instructor-led, Role-based e-learning modules, Job aids / quick reference, Super-user / champion network, One-on-one coaching, Other
• Who would you nominate as change champions for finance, IT, and operations? (names and roles)
• Which adoption metrics will you monitor to know people are actually using the new system? Options: Logins / usage rates, Process completion time, Number of manual reconciliations, Exception volume / resolution time, Training completion rates, User satisfaction / NPS, Other
• If adoption stalls after phase one, what remediation approaches would you accept? Options: Additional targeted training, Extend parallel run period, Deploy external change specialists, Revisit and simplify process design, Introduce incentives / performance KPIs, Other

How confident are you in the SI and commercial safeguards — where is the safety net?

• Have you validated the systems integrator’s delivery model and cost assumptions against deals of similar complexity? Options: Yes — fully validated with references, Partially validated, Not yet validated, We will validate jointly with you
• What contingency percentage do you expect or require in the SI implementation budget? Options: 0–5%, 5–10%, 10–20%, 20%+, Unsure
• Which commercial protections do you consider necessary to guard against scope creep or schedule slippage? Options: Fixed-price milestones, Time & materials with cost cap, Incentive / penalty clauses, Formal change-order process, Dedicated contingency fund, Other
• Do you require reference checks from customers in your vertical with similar complexity before we proceed? Options: Yes — mandatory, Preferable, Not necessary, Unsure
• What governance cadence will you expect during implementation (select all that apply)? Options: Weekly PMO / delivery calls, Bi-weekly working sessions, Monthly steering committee, Daily stand-ups during cutover, Ad hoc escalation meetings, Other

Agreeing next moves — who commits to what, and when?

• What specific decisions or deliverables do we need from you in the next 14 days to keep the timeline on track?
• Who will be responsible for producing the chart of accounts and entity mapping, and when can we expect those artifacts?
• Please confirm availability windows for key stakeholders for a 2-week discovery workshop (list dates or date ranges).
• What constraints or risks should we document now that would prevent starting the next phase (e.g., budget not approved, SI not contracted, regulatory hold)?
• Do you agree to a proposed discovery roadmap and governance touchpoints we’ll present at the end of this session? Options: Yes — agree, Yes — with modifications, No — propose alternate approach, Need more information before committing

Tell Us Where You Live Today

• What core ERP or financial systems are you currently running across entities (pick all that apply)? Options: Oracle E-Business Suite, SAP ECC / S/4HANA, Workday Financials, Microsoft Dynamics (AX/365/GP), Infor, Custom/on‑prem homegrown, Multiple legacy ERPs, Not sure / needs inventory
• How many legal entities or reporting units will be in-scope for your first consolidation phase? Options: 1–3, 4–10, 11–25, 26–100, 100+
• When was the last time you performed a major ERP upgrade or consolidation effort (rough timeframe)? Options: < 2 years, 2–5 years, 6–10 years, > 10 years, Never / unknown
• Where do the authoritative general ledger and intercompany books reside today (brief description of systems and any off-ledger processes)?
• Describe any critical spreadsheets, shadow systems, or bolt‑on applications you rely on weekly for financial reporting.

Are We Sure This Is Just 'A System' Problem?

• What business pain forced you to consider replacing or consolidating your ERP now—what’s at stake if nothing changes? Options: End-of-support for current vendor, Post-acquisition consolidation, Cannot meet consolidated close targets, Regulatory compliance risk, Cost of upgrades/maintenance, Inability to scale operations, Other
• How urgent is a decision and why—what happens to the business if you miss your target timeline? Options: Critical (months), Important (6–12 months), Strategic (12–18 months), Exploratory (no fixed timeline)
• Which executive sponsors will be judged on the outcome and what are their primary success criteria (CFO, CIO, COO, CEO, Board)? Options: CFO, CIO/CTO, COO, CEO, Board / Audit Committee, Business Unit Leaders, Other
• Which functions feel the pain most acutely today (choose all that apply) and give a one-sentence example of the worst current failure they face. Options: Finance / Accounting, Procurement, Manufacturing / Production, Supply Chain / Logistics, HR / Payroll, Sales / Billing, IT / Infrastructure
• If we were honest: how much of your current 'close' or reconciliations rely on manual workarounds versus automated system postings (estimate percentage)? Options: 0–10%, 11–30%, 31–60%, 61–90%, 91–100%

Where Customization Became a Cage

• How many major customizations or bespoke modules are in production that business users call 'non‑negotiable'? Options: None, 1–5, 6–20, 21–50, 50+
• Which customizations must be preserved as-is for regulatory, contract, or core-process reasons—list names and why they're critical.
• Who owns ongoing changes to custom code today (internal developers, external SI, both) and how responsive are they to urgent fixes? Options: Internal team, External SI partner, Hybrid/internal + SI, No clear owner
• How well documented are your custom processes and code (choose the best fit)? Options: Fully documented with tests, Partially documented, Mostly tribal knowledge, Not documented at all
• Which customization types create the most upgrade or migration risk—reports, interfaces, validations, unique accounting flows, or other? Pick up to three and describe one example. Options: Reports, Interfaces / integrations, Validations / custom GL logic, User interface custom screens, Custom workflows/approvals, Data transformations / nonstandard chart

Reconciliations That Live in Spreadsheets

• Which reconciliations are currently the largest time sink each month (AP, AR, Intercompany, Fixed Assets, Bank, Inventory)? Options: Accounts Payable, Accounts Receivable, Intercompany, Fixed Assets, Bank / Cash, Inventory, Payroll, Other
• How long does your consolidated month‑end close take today (select range) and who are the critical contributors? Options: ≤5 business days, 6–10 business days, 11–15 business days, 16–30 business days, >30 business days
• How often do reconciliation differences trigger late adjustments or restatements (rarely, occasionally, frequently) and give a brief example of a recent costly adjustment. Options: Rarely, Occasionally, Frequently
• Which parts of reconciliations rely on manual matching or Excel macros that we should plan to remove first?
• What level of detail do auditors expect in reconciliation evidence, and are there standing audit findings tied to reconciliation practices? Options: Full transaction-level evidence, Summary-level with support, Inconsistent expectations across entities, Yes — open audit findings, No significant audit issues

The Touchpoints We Can't Break

• Which downstream systems or external partners absolutely must keep running unchanged during cutover (banking, payroll vendor, manufacturing MES, tax engine, e‑invoicing)? Options: Banking / Treasury, Payroll provider, Manufacturing / MES, Tax calculation engine, Trading / EDI partners, Carrier / TMS, Customer billing portals, Other
• What types of integrations are predominant today—real‑time APIs, scheduled batch files, EDI, point‑to‑point middleware, or manual exports? Options: Real-time API, Scheduled batch/flat files, EDI, Point‑to‑point custom connectors, Middleware/ESB, Manual exports/imports
• Who owns each integration (internal team, SI, third‑party vendor) and how quickly can they produce interface specs or sample data? Options: Internal owners, Systems Integrator, Third‑party vendor, No clear owner
• What SLAs or latency constraints exist for key integrations (near real‑time, within minutes, daily batch, end‑of‑day)? Options: Near real-time (seconds/minutes), Within 30 minutes, Within a few hours, Daily batch / EOD, Weekly
• Are there any external or partner systems with complex certification or compliance requirements (banking, customs, tax authorities)? If so, name them and the constraint.

If Data Migration Stumbles, What Breaks First?

• Which data domains are highest risk during migration—master data, transactional history, open AR/AP, inventory valuation, fixed assets, or tax history? Options: Master data (customers/vendors/items), Open AR/AP and subledger balances, Historic transactional history, Inventory balances and valuation, Fixed assets and depreciation, Tax and statutory ledgers
• What tolerance do you have for daylight differences between source and target systems at cutover (zero tolerance, small recon tolerances, interim balancing allowed)? Options: Zero tolerance (must match exactly), Small reconciled variances allowed, Interim balancing with offsets allowed, Unsure / need to define
• How far back do you need transactional history accessible in the new system (full history, 3 years, 1 year, summary balances only)? Options: Full history, Last 7+ years, Last 3 years, Last 1 year, Summary/open balances only
• Are there legal, tax, or audit retention rules we must honor during migration (specific jurisdictions or retention periods)? Please list them.
• Which reconciliation or validation reports must be produced immediately after migration (e.g., trial balance match, intercompany eliminations, AP aging)? Options: Trial balance match, Intercompany reconciliation, AP aging vs source, AR aging vs source, Inventory valuation report, Fixed asset rollforward

Imagine a Month-End That Doesn’t Drain You

• If the month-end felt fast, predictable, and low-stress, what three concrete differences would you notice first?
• Which measurable outcomes below would signal success for phase 1 (pick up to three)? Options: Consolidated close ≤15 business days, Automated intercompany eliminations, Reduction in manual journal entries by %, Real-time cash position, Elimination of key spreadsheets, Lower ongoing TCO
• What acceptance criteria should govern go/no‑go for the first cutover (data match thresholds, business process sign‑off, transaction testing coverage)?
• How long of a parallel-run or stabilization period do you consider minimally acceptable to feel confident in cutover (days/weeks/months)? Options: No parallel (big bang), 1–2 weeks, 3–6 weeks, 1–3 months, 3+ months
• Which success signals are non-negotiable (e.g., bank reconciliation accuracy, payroll processed correctly, invoices not lost)? List up to three.

Who Needs to Be in the Room (and Who Won't Be Happy if They Aren't)

• Who are the essential stakeholders that must participate in discovery and testing (names or roles: CFO, process owners, tax, audit, IT, SI lead)? Options: CFO/Finance Leadership, Process Owners (e.g., AP/AR/GL), Tax/Compliance, Internal Audit, IT/Integration Team, Procurement / Supply Chain, Operations / Manufacturing, HR / Payroll, Systems Integrator Lead
• Who holds final sign‑off authority on financial cutover and who will sign the acceptance checklist?
• Which groups are likely to resist change most and why (fear of disruption, loss of control, training burden, job impact)? Options: Finance users, Operational staff, IT team, Third‑party vendors, No resistance expected, Other
• How many active end users will need training in phase 1 and what is the profile (power users, basic users, external partners)? Options: <50, 50–200, 201–500, 501–2000, 2000+
• Who will be the program manager on the customer side and what authority will they have to make cross‑functional tradeoffs?

Quick Wins & Guardrails — The Practical Next Steps

• If we could deliver one tangible win in the first 90 days, what should it be (improve close, automate a reconciliation, stabilize AR aging, implement unified chart of accounts)? Options: Faster consolidated close, Automate key reconciliations, Unified chart of accounts, Stabilize AR/AP processes, Integrate a critical partner system, Other
• Which modules or capabilities should be in phase 1 (financials, intercompany, tax, procurement, fixed assets)? Select preferred scope for first deployment. Options: Core GL & Close, AP/AR, Intercompany & Allocations, Tax & Statutory reporting, Fixed Assets, Procurement (basic)
• What migration approach do you prefer for phase 1: big-bang historical load, phased load with summaries, or live cutover with minimal history? Options: Full historical load, Phased historical load (years), Summary/open balances only, Live cutover with minimal history
• What contingency budget percentage would you expect to reserve for scope creep or late discovery during implementation? Options: 0–5%, 6–10%, 11–15%, 16–25%, 25%+
• What would make you say 'go' after a proof-of-concept or sandbox demo—what evidence convinces you to proceed? Options: Matches our chart of accounts scenarios, Integration feasibility proven, Data migration sample matches, Executive alignment & SI cost model validated, Positive reference from peer industry

Quick Read: Where Do You Stand Right Now?

• How prepared do you feel today to begin a financials-first deployment? Options: Completely ready, Mostly ready, Partially ready, Not ready yet
• Target timeline for an initial production cutover (months from now)? Options: <1 month, 1–3 months, 4–6 months, 7–12 months, 18+ months / not decided
• Are executive sponsors (CFO + CIO or equivalent) committed and available through cutover week? Options: Yes — committed and available, Committed but limited availability, Sponsors identified but not fully committed, Sponsors not yet identified
• Is a certified systems integrator already engaged to own cutover execution and migration workstreams? Options: SI engaged and scoped, SI identified but not contracted, No SI yet — evaluating partners, We will use internal resources only
• What keeps you up at night about this upcoming deployment (single biggest concern)?
• Have you completed any previous ERP migrations or large finance system cutovers in the last five years? If so, briefly describe outcomes and lessons.

What Would Break This Cutover Before It Starts?

• If you had to name one single failure that would stop cutover dead, what would it be?
• Which of the following technical risks do you see as highest likelihood/impact (select up to three)? Options: Data migration accuracy, Missing integration points, Environment instability, Insufficient access/credentials, Performance on go-live day, Other
• Which business processes cannot tolerate any downtime during cutover (e.g., AP payments, shop floor control, payroll)? Options: Accounts Payable, Accounts Receivable, Payroll, Shop-floor/MES, Procurement/PO creation, Customer billing/invoicing, Other
• Do you already have blackout windows, period-end freezes, or regulatory dates that constrain when a cutover can occur? Options: Yes — fixed blackout windows, Yes — flexible windows with approvals, No fixed windows, Unsure / need to confirm
• Where have past projects in your organization tripped up (people, process, tools)? Please give a concrete example.
• How emotionally ready are the process owners for a disruptive phase like cutover (e.g., nervous, cautiously optimistic, fully supportive)? Options: Nervous / highly resistant, Cautiously optimistic, Generally supportive, Fully aligned and enthusiastic

Who Holds the Keys — and Will They Share Them?

• If we requested admin-level access to your pre-production and extraction systems tomorrow, what would the process look like?
• Which environments are available now for migration testing (select all that apply)? Options: Development, Integration/QA, Pre-production (near-prod), Production replica, No non-prod environment available
• How long does it take to get formal access approvals for these environments (typical lead time)? Options: Same day, 1–3 business days, 1–2 weeks, 2+ weeks / needs change control
• Do you have SSO/Identity providers and approved service accounts for the SI to use, or will separate accounts be required? Options: SSO available for SI, Service accounts available, Both available, Neither — will need setup
• Who is the single point owner for environment access and change approvals during cutover (name/role)?
• Have you experienced access or segregation-of-duty roadblocks in prior projects that we should proactively plan around? Options: Yes — frequent blocker, Occasional issue, Rarely, Never

If the Data Were Wrong, How Would We Catch It?

• Which reconciliations or control reports would detect a migration error that matters to you (e.g., AR aging, GL trial balance, inventory valuation)? Options: GL Trial Balance, Account Reconciliations, AR Aging, Inventory Valuation, Fixed Assets register, Cash position report, Payroll register, Other
• What level of sampling/validation gives you confidence (e.g., 100% of high-risk accounts, 5% random sample, full reconciliation)? Options: Full reconciliation of critical accounts, 100% for top N accounts, Statistical sample (e.g., 5–10%), Spot checks only, Unsure — need SI recommendation
• Who must sign off on migrated data before a phase cutover (roles, not names)? Options: CFO/Finance Lead, Controller/Month-end Owner, IT/Infrastructure Lead, SI Migration Lead, Internal Audit, Other
• Do you have automated reconciliation tooling or will reconciliations be manual spreadsheets during validation? Options: Automated reconciliation tools in place, Hybrid (some automation, some manual), All manual spreadsheets, We plan to implement tools with this project
• If validation finds a material discrepancy on cutover day, what is the acceptable remediation SLA (time to fix) before rollback is considered? Options: <4 hours, 4–24 hours, 24–72 hours, >72 hours / require rollback

Can We Prove a Safe Cutover Without Breaking Production?

• What would have to happen during a parallel run for your leadership to feel confident moving off the old system?
• Preferred parallel-run duration to demonstrate stability for financials-first (choose best match)? Options: 1–3 business cycles (weeks), 1 full month, One month + month-end close, Multiple month-ends
• What rollback strategies are acceptable if key issues emerge (select all that apply)? Options: Full rollback to legacy, Selective rollback of specific modules, Pause and extend parallel run, Patch and continue (accept risk), Other
• Who has authority to call a rollback or hold-the-cutover decision in your organization? Options: CFO/Executive Sponsor, Program Steering Committee, IT Director, SI Program Lead with customer approval, Other
• What monitoring and real-time dashboards would you require during the dress rehearsal and cutover to feel in control?

Which Integrations Are Non-Negotiable?

• If an outbound or inbound interface failed at go-live, which downstream system failure would cause the most immediate business pain?
• Which integration types must be preserved exactly (select all that apply)? Options: Real-time APIs, Batch ETL jobs, EDI connections, Middleware/ESB flows, Flat-file imports/exports, Manual CSV transfers
• Who owns each critical integration today (internal team or third party)? Please list role and org for the top three integrations.
• What are your batch windows and SLAs for integrations that run overnight or at month-end? Options: Multiple daily windows, Single nightly window, Short maintenance windows only, No batch windows — near-real time required, Unsure / need to document
• If an integration cannot be fully migrated for phase one, what acceptable manual or temporary workaround would you permit? Options: Manual CSV uploads, Interim middleware mapping, Hybrid dual-write with reconciliation, Delay that integration to a later phase, None — must be migrated

Money, Time and the ‘What Ifs’

• If the project slips two months, what is the most tangible business impact you expect (cost, compliance, lost revenue)?
• How much contingency budget has been set aside for deployment risk and scope creep? Options: >20% of implementation estimate, 10–20%, <10%, No contingency budget defined, Unsure / need to confirm
• Do you require the SI to provide a formal contingency plan and cost model that ties to rollback and extended parallel-run scenarios? Options: Yes — required, Preferred but not required, No — not required, Unsure
• What internal resource constraints are most likely to slow cutover execution (select all that apply)? Options: Key SME availability, Budget approvals, IT infrastructure capacity, Change control timelines, Vendor/third-party availability, Other
• If an unexpected compliance or audit requirement appears during cutover, how quickly can you mobilize an executive decision? Options: Within hours, 1–2 business days, Several days to a week, Longer / unclear

Commitments & Next Steps We’ll Need From You

• If asked to commit to three concrete actions this week to accelerate readiness, what are you willing to pledge (roles/activities)?
• Which of these immediate items can you provide in the next 7–14 days (select all that apply)? Options: Access approval to pre-prod, Sample ledgers and mappings, List of critical integrations and contacts, Signed cutover window date(s), Dedicated SME time for testing
• Preferred cadence for deployment governance meetings during readiness and cutover? Options: Daily standup, 3x weekly, Weekly, Bi-weekly, Ad-hoc as needed
• Who should be the primary contact for cutover coordination (name, role, email)?
• What are the best 2–3 calendar weeks in the next 6–8 weeks for a full dress rehearsal and test migration?

Opening: Quick Check-In on Cutover Timing

• What is your target cutover date for this deployment phase?
• Who are the primary stakeholders we should expect to have in the cutover room and available for final acceptance? Options: CFO, CIO/CTO, Head of Finance Operations, IT Lead, SI Project Manager, Data Migration Lead, Internal Audit, Procurement Lead, HR Lead, Other
• How do you prefer we communicate live cutover decisions and status updates? Options: Dedicated Slack/Teams channel, Email + escalation list, Virtual war-room (video link), On-site command center, Daily standups only, Executive-only updates
• What parallel-run duration do you expect before we finalize acceptance (choose best fit)? Options: No parallel run (immediate switch), 1–3 days, 1 week, 2 weeks, 1 month, Longer than 1 month
• Who will be our day-to-day point of contact on your team for validation activities (name, role, contact)?

If We Can’t Trust the Numbers, Nothing Else Matters

• If even small ledger mismatches could derail approval, what accuracy threshold would keep your team confident? Options: Exact match at currency level, ≤0.01% variance, ≤0.1% variance, ≤0.5% variance, Tolerance defined per account/report, Other
• For the following areas, please state the acceptable reconciliation tolerance or rule (AR, AP, GL, Inventory, Fixed Assets).
• Which reconciliation or control reports must match exactly as part of cutover acceptance? Options: Trial balance (by entity), AP aging, AR aging, Intercompany eliminations, Bank reconciliation / cash position, Fixed asset rollforward, Inventory valuation, Tax reports, Other
• Have you had prior migrations where specific data issues recurred? Please describe one recent example and its operational impact.
• Who owns master data (chart of accounts, legal entities, vendors, customers) and how will freeze/updates be coordinated during migration? Options: In-house Data Team, Finance team, IT/ERP team, Systems Integrator, Shared governance, Other

Show Me the Tests You Can't Ignore

• Which single business scenario, if it failed in testing, would make you stop the go-live? Options: Consolidated financial close, Cash reconciliation, Payroll processing, Order-to-cash, Procure-to-pay, Intercompany eliminations, Manufacturing costing/BOM, Revenue recognition, Other
• List the top acceptance tests you require; for each, briefly describe the expected result and explicit pass/fail criteria.
• How representative should test volumes be for each scenario? Options: 10–50 sample transactions, Full month volume, Quarter-to-date, Year-to-date sample, Percentage of daily volume (specify), Other
• Which automated test suites, reconciliation tools, or scripts must be run and captured as evidence? Options: ERP built-in reconciliations, SI proprietary scripts, Informatica/ETL validations, Celigo/Integration tests, Excel reconciliations with signatures, Robotic/automated UI tests, Other
• Who on your side will own sign-off for each test area? Please provide name and role for each test owner.

Who Gets to Say 'Yes' (and 'No')?

• Who has the unilateral authority to refuse go-live at cutover and why does that authority sit with them? Options: CFO, CIO/CTO, Head of Finance Ops, SI Project Lead, Joint steering committee, Other
• If we achieve partial readiness (for example, financials pass but procurement does not), which staged-acceptance approach do you prefer? Options: Accept financials only and delay other modules, Hold entire phase until all modules pass, Stagger go-live by module with mitigation plan, Conditional acceptance with remediation SLA, Other
• What formal sign-off artifacts do you require for acceptance (choose all that apply)? Options: Signed acceptance form, Executive approval memo, Full test runbooks with results, Reconciliation report PDFs with stamps, Email trail from approvers, Legal sign-off, Other
• What is the escalation path and expected timeline if a late-breaking defect threatens sign-off? Options: Immediate executive alert (hours), 24-hour crisis team, 72-hour triage window, Weekly steering committee decision, Other
• Will internal audit or external auditors need to validate the migration artifacts prior to formal sign-off? Options: Yes — internal audit, Yes — external auditors, No auditors required, Unsure / needs confirmation

What If Something Breaks During Cutover?

• Imagine the worst plausible outage during cutover—what single contingency must exist to protect core operations?
• What is your maximum tolerable business outage for core finance functions during the cutover (hours)? Options: 0 hours — no outage tolerated, <4 hours, 4–12 hours, 12–24 hours, >24 hours
• Which rollback or recovery strategies do you require we have in place (select all that apply)? Options: Full snapshot restore to legacy, Point-in-time database recovery, Transaction-level replay, Freeze-and-continue on legacy for X days, Dual-write rollback plan, Other
• Who is authorized to initiate a rollback and which approvals must be captured before doing so?
• If a rollback is initiated, how quickly must normal operations be restored and what communication cadence do you expect? Options: Immediate hourly updates, Every 4 hours, Twice daily, Daily summary, Other

Counting Success After Go-Live

• Which single post-go-live metric failing would make you conclude the migration did not deliver the expected value? Options: Consolidated close >15 business days, Reconciliation backlog above threshold, Cash discrepancies exceeding tolerance, High-severity defects persist, Inventory variance exceeds tolerance, Other
• Choose up to six KPIs we should monitor in the first 30/60/90 days to validate success. Options: Days to close (consolidated), Days Sales Outstanding (DSO), AP aging >90 days, Number of manual journal entries, Cash reconciliation variance, Intercompany reconciliation time, Inventory accuracy, Payroll accuracy, User adoption rate, Support ticket volume, System performance/response time
• What reporting cadence and audience do you expect for hypercare updates? Options: Daily to project team, Daily to steering committee, Twice weekly, Weekly executive summary, Real-time dashboard access, Other
• What SLAs for issue prioritization and remediation do you require during hypercare? Options: P1 <4 hours, P1 <24 hours, P2 <48 hours, P3 <5 business days, Custom SLA per issue type, Other
• Who will be the ongoing owner for continuous improvement after hypercare and when should the handover occur? Options: Customer IT, Finance Operations, Shared governance board, SI-managed for fixed period, Other

Let Evidence Speak: Deliverables & Archival

• Which evidence formats convince your auditors and approvers (choose all that apply)? Options: Time-stamped reconciliation reports, Signed logs with hashes, Executable test scripts and results, Screenshots with run IDs, Excel recon with sign-off column, Other
• Which minimum deliverables must be archived as part of the acceptance package and for how long should they be retained? Options: Test cases/results, Migration mapping sheets, Data extract snapshots, Reconciliation reports, Signed acceptance forms, Cutover runbooks, Retention: 6 months, Retention: 1 year, Retention: 3 years, Retention: 7+ years
• How do you want the acceptance evidence packaged for review? Options: Single PDF binder, Folder per functional area, SharePoint/Drive link, Integrated into GRC tool, SI portal workspace, Other
• Who will approve the final acceptance package before signatures are circulated (name and role)?

Commitment & Immediate Next Steps

• Given everything we've discussed, what is the single biggest blocker that could delay your final sign-off?
• On a readiness scale, how prepared do you feel today to execute and validate this phase? Options: Fully ready, Mostly ready — minor gaps, Some substantive gaps remain, Not ready at all, Unsure
• What are the three most important actions we should take this week to materially de-risk acceptance?
• Please name the 1–3 owners we should lock into the cutover war-room and provide preferred contact method for each.
• Confirm the committed date by which you will provide final sign-off or a formal list of blocking items after cutover. Options: Same day, 1–3 business days, 4–7 business days, >7 business days, Unsure