Quick introductions — who should we be talking to?

• Which executives should be included in our initial alignment conversations? Options: CIO/CTO, CFO, CEO/President, Head of IT/VP IT, Head of Finance/VP Finance, COO, CHRO/Head of HR, Procurement Lead, Legal Counsel, Other
• Please provide the single best sponsor contact for day-to-day alignment (name, role, preferred contact method).
• Who is the ultimate signatory for major commercial commitments (contracts, change orders, >$500k)? Options: CEO/Board, CFO, CIO, Procurement Committee, Divisional President, Other
• Which functional leaders do you expect to be active decision-makers on scope and acceptance? Options: Finance, Supply Chain, Manufacturing/Operations, HR/Payroll, IT/Infrastructure, Sales/Commercial, Procurement, Legal/Compliance, Other
• Have any of the named leaders sponsored or led an ERP implementation before? Tell us who and one result or lesson from that experience.

Who's really calling the shots?

• If the board could wave a wand, whose decision would actually move this project forward today?
• Who has final approval over changes to project scope (features, modules, customizations)? Options: Program Sponsor/Executive, Steering Committee, CIO/IT, CFO/Finance, Procurement, Other
• Who has final approval for budget increases or contingency draws? Options: CFO, CEO/Board, Steering Committee, Program Sponsor, Procurement
• Who sets or approves the target go-live date? Options: Executive Sponsor, PMO/Program Manager, Steering Committee, External Partner (with Sponsor sign-off), Other
• How are conflicts between these decision-makers typically escalated and resolved?

Money, mandates, and maybes

• How committed is the funding today — fully allocated, approved by board, conditional, or still being sized? Options: Board-approved and allocated, Allocated but awaiting final approval, Conditional on business case milestones, Preliminary estimate only, Unfunded
• Is the budget structured as a fixed amount, a phased funding model, or flexible based on scope? Options: Fixed, Phased/milestone-based, Flexible within governance, Not yet decided
• What level of cost overrun is tolerated before leadership must reauthorize (choose the closest): Options: None — strict limit, Up to 5%, 5–10%, 10–20% with justification, Any increase requires board review
• Are there pre-conditions tied to funding (e.g., executive sign-off, vendor selection, regulatory sign-off)? Please list.
• If additional investment is required for unforeseen complexities, who would own the decision to proceed? Options: CFO, CEO/Board, Steering Committee, Program Sponsor, Other

If the timeline shrinks, what breaks first?

• What immovable dates drive this program (select all that apply)? Options: Regulatory deadline, Fiscal year close, Audit deadline, Merger/acquisition close, Contract renewal, Board reporting, Customer commitments, Other
• How much schedule compression can your organization tolerate before it materially risks business continuity? Options: None — hard date, 1–4 weeks, 1–3 months, 3–6 months, Flexible beyond 6 months
• If timelines shorten, which deliverables are you prepared to defer to a subsequent phase? Options: Analytics and BI, Advanced customizations, Non-core integrations, Fresh UI/UX work, Global rollouts – regional first, None — everything is must-have
• Which internal or external events would force a hard freeze or pause of the program?
• Who is responsible for the master schedule and for communicating trade-offs to the executive team? Options: PMO/Program Manager, External Implementation Partner, CIO/IT, Steering Committee, Other

How will we know this actually worked?

• Which outcome metrics would make the board call this a success? Pick up to five. Options: On-time go-live, On-budget, Data migration accuracy, Reduction in month-end close time, Inventory accuracy improvement, Improved order-to-cash cycle, User adoption % trained, FTE reduction / productivity gain, Regulatory compliance achieved, Other
• Who will be accountable for tracking and reporting these KPIs after go-live? Options: Program Sponsor, Business Process Owners, PMO/Program Manager, CFO/Finance, IT/Operations, Other
• What baseline data or measurements exist today for your top KPIs (comprehensive, partial, spotty, none)? Options: Comprehensive and auditable, Partial but usable, Spotty / inconsistent, No baseline available
• When would you expect to see measurable ROI or operational improvement (select the closest)? Options: 0–6 months post go-live, 6–12 months, 12–24 months, 2+ years, Unsure
• What acceptance criteria or exit tests would you require before declaring the program a success?

Politics, allies, and quiet opponents

• Who stands to lose influence, budget, or comfort if this new ERP succeeds, and how might they react?
• Which departments have historically slowed or derailed IT programs here, and what were the root causes?
• Do you have named internal champions who will actively promote change and adoption? Options: Yes — executive sponsor, Yes — business process owner(s), Yes — change lead/PMO, No identified champions, Unsure
• How direct or subtle do you expect resistance to be (choose the best fit)? Options: Open and vocal, Passive but obstructive, Politically maneuvered, Mostly neutral, Supportive
• What incentives, governance levers, or communication approaches have historically reduced resistance here?

Red flags, deal-breakers, and escapes

• Are there regulatory, contractual, or security constraints that would prevent certain architectures or cloud approaches? Options: Yes — major constraints, Yes — manageable constraints, No significant constraints, Unsure — need to investigate
• Do existing vendor contracts or long-term support agreements limit our integration or migration options? Options: Yes — significant limitations, Yes — some limitations, No, Unsure
• Which data domains are legally or operationally restricted (select all that apply)? Options: Finance/GL, Payroll/HR, Customer PII, Supplier contracts, Manufacturing IP, None/No special restrictions
• Do you require consultants with industry experience, security clearances, or local presence? Please specify. Options: Senior program lead with industry experience, Functional consultants with domain experience, Security-cleared personnel, Local/on-site resources required, Remote resources acceptable, Other
• What would be a non-negotiable 'no-go' condition before we mobilize a program (e.g., unresolved data holds, missing sponsor, no budget)?

Next move — aligning on a minimal win

• If we had to agree on a single immediate milestone to demonstrate progress within 30 days, what would that be? Options: Executive alignment workshop, Validated sponsor and decision matrix, Baseline data inventory and risk log, Preliminary scope and budget estimate, Integration dependency map, Other
• Who must attend a 60–90 minute sponsor alignment meeting to unblock decisions? (list roles) Options: CEO/Board rep, CFO, CIO, Head of Finance, Head of Operations, PMO Lead, Procurement, External Partner Lead, Other
• What concrete pre-work can your team commit to delivering within two weeks to accelerate alignment (data extract, org chart, contract copies)?
• What governance cadence would you prefer for the program ramp (choose one)? Options: Weekly steering + weekly PMO, Biweekly steering + weekly PMO, Monthly steering + weekly PMO, Ad hoc with escalation only, Executive sponsor-led weekly
• Would you agree to a brief sponsor-only alignment call next week to confirm authority, budget posture, and the 30-day milestone? Options: Yes — schedule it, Maybe — need to confirm, No — prefer different timing

Start with the Big Picture — Where Are We Now?

• In two sentences, how would you describe your current ERP and supporting application landscape?
• Which of the following core systems are active today in your environment? Options: Finance / ERP, Supply Chain / WMS, Manufacturing / MES, HR / Payroll, CRM / Sales, BI / Analytics, Custom legacy apps, Other
• How is your ERP currently hosted? Options: Cloud (SaaS), Private cloud / hosted, On-premises, Hybrid (mix of cloud and on‑prem), Multiple models across business units, Not sure
• Which statement best describes your ERP footprint today? Options: Single global instance, Multiple regional instances (2–5), Many fragmented instances (6+), One core system + several bolt‑ons, Unsure / need to confirm
• When was the last major upgrade, consolidation, or migration effort, and what changed?
• Who on your team is the day‑to‑day owner for the ERP landscape and integrations? Please name role(s) and primary contact if available.

What’s Actually Broken — Not the 'Everything' Answer

• Which single legacy process or system failure do you believe is quietly costing the most time, money, or credibility?
• Can you share a recent concrete incident (dates, impact, teams affected) that illustrates this problem?
• How frequently does this issue occur? Options: Daily, Weekly, Monthly, Quarterly, Rarely / one‑offs
• What measurable business outcomes does it affect (revenue, days sales outstanding, stockouts, compliance fines, cycle time, etc.)? Please quantify if possible.
• What workarounds or manual fixes are in place today, and who bears the burden of those fixes?
• If we solved this problem tomorrow, what would change in the first 90 days—both operationally and emotionally for your team?

Hidden Integration Debt — Where Data Gets Lost in Translation

• How often does data fail to arrive or be reconciled across systems, causing rework, disputes, or missed customer commitments? Options: Constantly, Often, Sometimes, Rarely, Never / not sure
• Which types of integrations move critical data today? (Select all that apply) Options: Order-to-cash, Procure-to-pay, Inventory sync, General ledger / financial posting, HR / payroll feed, Supplier EDI, API-based custom integrations, Batch ETL jobs, Other
• Which middleware or integration platforms do you use (iPaaS, ESB, custom scripts)? Options: MuleSoft / iPaaS, Dell Boomi, SAP PI/PO, Custom middleware, Point-to-point scripts, Message broker (Kafka, RabbitMQ), No dedicated middleware, Not sure / needs confirmation
• Which three integrations would you classify as 'business critical' and why?
• How are integration failures detected today—automated alerts, manual reconciliation, or after customer impact? Options: Automated alerts & monitoring, Basic logs reviewed periodically, Manual reconciliation, We discover on customer complaints, Unknown
• Who is accountable for integration reliability—IT, a middleware team, or business application owners? Options: IT / Integration team, Application teams, Shared responsibility, Third-party vendor, Not clearly assigned
• What maximum delay or data lateness can the business tolerate for critical flows (in minutes or hours)? Options: Near real-time (<5 min), Minutes (5–60), Hours (1–6), Up to 24 hours, More than 24 hours

If the Data Were Honest — What Would It Say?

• If your master data could speak, which hard truth would it confess—duplicates, missing attributes, wrong ownership, or outdated mappings?
• Which data domains are most problematic today? Options: Customers, Suppliers, Items / SKUs, Chart of accounts, Employee records, Site/location master, Transactional data quality, Other
• Do you have active data quality metrics or dashboards (completeness, duplicates, referential integrity)? Options: Comprehensive dashboards with trends, Ad-hoc reports, Only manual checks, No formal measurement, Unsure
• Have you attempted a data migration or cleansing project in the last 24 months? What worked and what didn’t?
• Who owns data governance and stewardship across master and transactional domains? Options: Central data governance team, Functional business owners, IT / Data team, No clear owners, Hybrid model
• What tools do you use (MDM, data quality, ETL), if any? Options: MDM solution, Data quality tooling, ETL / ELT tools, Custom scripts, None, Unsure
• How would you prioritize data fixes—what must be fixed before cutover vs. what can be remediated post‑go‑live?

What Could an Ideal Cutover Save or Break?

• When you picture cutover day, what’s the single worst-case scenario that keeps you up at night?
• What is your acceptable system downtime window for go‑live? Options: Less than 1 hour, 1–4 hours, 4–12 hours, 12–24 hours, More than 24 hours
• Are there blackout periods we must avoid (month-end, quarter-end, seasonality)? Select all that apply. Options: Month‑end close, Quarter‑end close, Year‑end / fiscal close, Peak sales season, Payroll run windows, No blackout windows, Other
• How many full dress rehearsals / cutover dry runs have you executed in the last 2 years? Options: None, 1, 2–3, 4–6, More than 6, Unsure
• What rollback criteria would force you to abort a cutover and revert to the legacy environment?
• Who would sit in the cutover command center and who has final sign‑off to proceed/abort?
• Which business processes must be fully operational immediately after go‑live (top 3)?

People, Power, and Change — Who Decides and Who Resists?

• Who inside your organization has the most to lose from a move to a new ERP, and how do they typically express resistance?
• Who are the formal sponsors and budget holders for this program? Options: CIO, CFO, COO, Business Unit Leader, Head of Supply Chain, Shared sponsorship, Other
• Is there an executive steering committee or program governance model today? If so, describe composition and cadence.
• Where do you anticipate the biggest adoption gaps—roles, geographies, or functions? Options: Finance teams, Supply chain / operations, Manufacturing / plant, Sales / order entry, Regional offices, Third‑party users / suppliers, Other
• What learning and training approaches have worked best historically (classroom, train‑the‑trainer, online, role‑based simulations)? Options: Instructor‑led classroom, Train‑the‑trainer, eLearning / modules, Role‑based hands‑on simulations, On‑the‑job coaching, Blended learning, Other
• How available are your subject matter experts during implementation? Options: Fully available (dedicated), Part-time availability, Over-allocated across projects, Not assigned yet, We need vendor support
• Who outside IT must be convinced that this change is worth the disruption (list roles and their biggest concerns)?

Risk, Cost, and the Measures That Matter

• What hidden cost or complication has surprised you most on previous ERP projects?
• How do you currently treat requested customizations—strict guardrails, pragmatic exceptions, or open to heavy tailoring? Options: Strict guardrails (minimal customization), Pragmatic exceptions, Flexible / customization friendly, No formal policy
• What is your internal tolerance for change orders as a percent of initial scope (choose the closest)? Options: <5%, 5–10%, 10–20%, 20–40%, >40%, No predefined tolerance
• Which regulatory, security, or compliance requirements must we design for (select all that apply)? Options: SOX / financial controls, GDPR / data privacy, HIPAA, PCI‑DSS, ITAR / export controls, Industry-specific regulations, None / not applicable, Other
• Describe the most sensitive system or dataset we must avoid disrupting or exposing during migration.
• What contingency budget or timeline buffer do you typically protect for large platform projects? Options: No buffer, 5–10% budget / 1–3 months, 10–20% budget / 3–6 months, 20%+ budget / 6+ months, Undecided

Small Experiments, Big Confidence — What's the Safest Way Forward?

• If you had to prove value in 90 days, what small process or dataset would you pick as a pilot to demonstrate measurable impact?
• What success metrics would convince executives this pilot is ready to scale? Options: Cycle time reduction, Error reduction (%), Cost savings, User adoption / task completion, Data quality improvement, On-time delivery / SLA improvements
• Which business stakeholders must be involved in a pilot decision and sign-off? Options: Finance lead, Operations lead, IT / Architecture, Supply Chain lead, HR / People lead, CFO / CIO
• What minimum dataset or number of transactions would give the pilot statistical credibility? Options: Small sample (under 1k txns), Medium (1k–10k txns), Large (>10k txns), By time window (e.g., 30 days), Unsure — need to explore
• How quickly could your team commit resources to a tightly scoped pilot (choose one)? Options: Immediately (within 2 weeks), In a month, In 2–3 months, Longer than 3 months, Unsure
• What would be the single easiest win from a pilot that would change stakeholder sentiment in your favor?

Realities to Align On — Next Steps and Practical Constraints

• What timeline do you feel is realistic for a full transformation from kickoff to stabilized operations? Options: 6–9 months, 9–18 months, 18–36 months, Multi-year phased program, Unsure / depends on scope
• Which internal approvals or milestones must occur before we can begin discovery workshops?
• What internal reporting cadence will we be expected to follow (weekly, monthly, executive checkpoints)? Options: Weekly, Biweekly, Monthly, Ad-hoc as needed, Executive milestones only
• Who needs to be in the room for our initial discovery workshops (roles, not names)?
• What would you like us to deliver at the end of this Current State Mapping stage (select all that apply)? Options: Landscape inventory & dependency map, Integration catalog and risk matrix, Data quality assessment & remediation plan, Cutover & rollback constraints, Resourcing and governance recommendations, Pilot definition and quick-win roadmap
• Finally, what concerns do you have about our asking these deep questions—what would make this conversation safer or more productive for your team?

Getting Ready Together — your timeline and stakes

• What is your current target go-live window for this ERP deployment? Options: Next 30 days, 30–60 days, 60–90 days, 3–6 months, 6+ months, TBD
• How confident are you, on a scale from 'fully confident' to 'we're stretching the date', that this window is realistic? Options: Fully confident, Mostly confident, Moderately confident, Uncertain, Date driven by external mandate
• Who is the executive sponsor(s) we should align with for final approval, and what are their top concerns about this timing?
• If the go-live slips 30 days, which business outcomes or financial metrics would be most at risk? Options: Revenue recognition, Month/quarter close, Supply continuity, Payroll/HR operations, Regulatory/compliance deadlines, Other
• Has the board or CFO placed any hard constraints (budget caps, blackout periods, audit windows) that limit our scheduling flexibility? Options: Yes—budget cap, Yes—blackout/seasonal window, Yes—audit/ compliance window, No hard constraints, Unsure

If We Go Live Tomorrow, What Would Break?

• If we flipped the switch tomorrow, which three processes do you expect would fail first or cause the biggest disruption?
• How long is the business willing to tolerate degraded capability in those processes before executive intervention? Options: Hours, One business day, Up to 3 days, Up to a week, Not acceptable
• Which recent incident(s) (past 12–18 months) should inform our cutover risk planning—what happened and how was it handled?
• Which single point of failure in your current landscape concerns you most (e.g., payroll batch, EDI, warehouse operations)? Options: Payroll, EDI/partner interfaces, WMS/warehouse, Manufacturing/MES, Finance close, Other
• Who on your side is empowered to pause a go-live if things are deteriorating, and what criteria would they use?

Where Does Your Data Live — and How Honest Are We About Its Quality?

• Which data domains are mission-critical for cutover (select all that apply)? Options: AR/Customer master, AP/Supplier master, GL/Chart of accounts, Inventory/Items, Bills of Material, HR/Employee records, Other
• What percent of those mission-critical data domains have been profiled and remediated to your standards? Options: 100%, 75–99%, 50–74%, 25–49%, Less than 25%, Not started
• Do you have working sample extracts and reconciliation scripts we can run end-to-end before cutover? Options: Yes—complete and available, Partial extracts available, Scripts exist but not tested, No, not yet
• Who are the appointed data owners for each critical domain (name or role) and how quickly can they resolve data defects during cutover?
• What acceptance criteria must be met for migrated data (e.g., balance tolerance, duplicate thresholds, % completeness)?

Who Actually Has the Keys — access, environments, and security

• Are all required environments (dev, test, pre-prod, prod) provisioned and tagged for our cutover rehearsals? Options: All provisioned, Most provisioned, Only dev/test provisioned, Not provisioned
• Which access or network dependencies could block our team from executing remote or onsite cutover activities (select all that apply)? Options: VPN/Network policies, Firewall rules, Privileged account provisioning, SAML/SSO configuration, Third‑party vendor access, None
• How long does it take on average to approve a new privileged account or access request in your organization? Options: Same day, 1–3 days, 4–7 days, More than a week, Varies greatly
• Who (role/title) will be the single point of contact for urgent access changes during rehearsals and cutover, and how reachable are they?
• Are there compliance or audit controls (e.g., change freeze, segregation of duties) that will influence how we plan access during go-live? Options: Yes—strict controls, Yes—moderate controls, No special controls, Unsure

Do Our Systems Breathe Together — integrations and external dependencies

• How many external interfaces/third‑party integrations must be live at cutover? Options: 0–5, 6–15, 16–30, 30+
• Which integrations are live-critical (real‑time or daily cutover dependencies) — please list systems or partners.
• Is middleware (e.g., iPaaS, ESB) fully configured in pre-prod and connected to external partners for end‑to‑end testing? Options: Yes—fully connected, Partially connected, Not connected yet, No middleware
• Do external partners/vendors support our rehearsal windows and have SLA commitments for cutover support? Options: Yes—all partners committed, Some partners committed, No formal commitments, Unsure
• Who owns each integration end-to-end (internal role or vendor), and how quickly can they respond to a production interface failure?

Can Your Tests Break It—and Let Us Fix It?

• Do you currently have an end‑to‑end test plan that mirrors the cutover sequence and includes business-critical scenarios? Options: Yes—comprehensive, Partial coverage, Basic unit tests only, No end‑to‑end plan
• How complete is your UAT user participation (percent of identified superusers who have signed up and executed scenarios)? Options: 100%, 75–99%, 50–74%, 25–49%, Less than 25%
• Is performance/load testing completed for peak‑volume processes that will run during or immediately after cutover? Options: Yes—passed, Yes—issues found, Planned but not run, Not planned
• Who will coordinate defect triage during rehearsals and cutover, and what is your target defect‑to‑resolve SLA during the window? Options: Same day, 48 hours, 5 business days, Depends on severity
• Can we access realistic test data sets that include edge cases (high volume customers, suspended accounts, complex BOMs)? Options: Yes—comprehensive, Partial, No

When Cutover Happens, Who’s in the Room?

• Have you identified and confirmed the cutover command center roles (decision maker, technical lead, business lead, communications, escalation)? Options: Yes—all confirmed, Some roles confirmed, Roles not yet assigned
• Who can make final acceptance calls during cutover (name/role), and are they available for the full window?
• What communication channels should the command center use for real‑time updates (select all that apply)? Options: Phone bridge, Dedicated Slack/MS Teams channel, Email summaries, War room in person, Other
• What time of day/day of week do you prefer to perform cutover activities to minimize business impact? Options: Weekend daytime, Weekend overnight, Weeknight overnight, End of month/quarter specific window, Other
• Do you have a pre-approved list of emergency contacts and delegation rules should primary contacts be unavailable? Options: Yes—documented, Partial list, No

What Will It Feel Like for Your People — adoption and support readiness

• What percent of end users are scheduled to receive role‑based training before go‑live? Options: 100%, 75–99%, 50–74%, 25–49%, Less than 25%
• Who are your trained superusers/champions by function, and how many are available during hypercare?
• What is your preferred post‑go‑live support model for the first 30–90 days (select up to two)? Options: Onsite hypercare team, Remote command center, Hybrid onsite/remote, Dedicated helpdesk queue, Shared responsibility with vendor
• How will business acceptance be measured day‑by‑day during hypercare (examples: transaction throughput, error rates, finance close timing)?
• Which internal teams are likely to resist the new processes and will need targeted change management? Options: Finance, Supply chain/warehouse, Manufacturing, Sales/Order management, HR/Payroll, IT/Infrastructure

If Everything Goes Wrong, What’s the Plan B?

• What are your hard rollback thresholds (explicit metrics or conditions that would trigger reverting to legacy systems)?
• Do you have verified backups and a documented restore procedure for critical data and configurations? Options: Yes—verified in pre-prod, Backups exist but not tested, No formal backups/process
• What recovery time objective (RTO) and recovery point objective (RPO) apply to the most critical processes? Options: RTO < 1 hour, RTO 1–8 hours, RTO 8–24 hours, RTO > 24 hours, Not defined
• Are there vendor escalation paths and guaranteed response SLAs if third‑party integrations fail during cutover? Options: Yes—documented SLAs, Informal commitments, No SLAs
• Who in your executive team needs to be briefed immediately if we hit a major cutover incident, and how should we frame that communication?

Last Check Before the Switch — go/no‑go criteria and next actions

• Looking across environments, data, integrations, testing, people, and contingency plans, which single area gives you the least confidence right now? Options: Data migration, Integrations, Access/environments, Testing coverage, Org readiness/training, Contingency plans
• What are the non‑negotiable go/no‑go criteria we must satisfy before locking the cutover date?
• Which rehearsals or dress‑rehearsal milestones would you like to see completed and validated before we set a firm schedule? Options: Full end‑to‑end dress rehearsal, Data migration rehearsal, Integration smoke test, UAT signoff, Command center run
• Realistically, what is the single next action you can commit to this week to increase readiness?
• Who should receive the readiness summary and final go/no‑go checklist from our team, and how would you like that delivered? Options: Email with attachments, Live review meeting, Secure portal upload, Executive summary + meeting

Getting Comfortable — Tell Us Where You Are

• Which statement best describes why you’re pursuing an ERP change right now? Options: Replace aging/unsupported system, Consolidate after acquisition, First enterprise-wide ERP, Cost reduction / efficiency, Regulatory or compliance driver, Other
• What is the target timeframe you and your leadership are expecting for selecting a partner and confirming a go-forward plan? Options: <3 months, 3–6 months, 6–12 months, 12–18 months, Undecided / exploratory
• Tell us briefly about any prior attempts to modernize or migrate ERP capabilities—what happened and why it didn’t meet expectations?
• Among cost, timeline, business disruption, and functionality, which single constraint feels most likely to derail this program if it isn’t managed? Options: Cost overruns, Timeline slips, Business disruption/cutover impact, Insufficient functionality, User adoption
• Who in the C-suite will be most visible in sponsoring this program, and who else do we need to keep reassured during discovery?

If This Keeps Going, What Breaks First?

• Which specific process, report, or outcome do you expect to fail or materially degrade if the current ERP remains unchanged over the next 12–18 months?
• How often do you encounter manual workarounds or spreadsheets because the system can’t handle a core process? Options: Daily, Weekly, Monthly, Rarely, Never
• Give an example of a recent operational issue that you traced back to the legacy system—what happened and what were the downstream effects?
• How do these failures show up to your external stakeholders—customers, suppliers, auditors—and how often has that caused reputational or contractual risk? Options: Frequently, Occasionally, Rarely, Never
• If we had to prioritize one business process to stabilize in the first 6 months, which should it be and why? Options: Order to cash, Procure to pay, Record to report, Manufacturing / production, HR / payroll, Other

Hidden Costs and Silent Risks

• Where are you quietly losing money, time, or credibility because of the current ERP—what’s the single most surprising cost you’ve uncovered?
• Which of these cost categories are currently the largest drain on your operations? Options: Manual reconciliation labor, Inventory carrying costs, System downtime, Rework and corrections, Third-party integrations / middleware fees, Audit / compliance penalties
• Estimate the annual dollar or FTE impact of those hidden costs (choose a range) — if unknown, select 'unsure' and explain. Options: <$100k, $100k–$500k, $500k–$2M, >$2M, Unsure—will need to calculate
• Have there been recent audit findings, regulatory lapses, or supplier/customer SLA breaches tied to system limitations? Describe one example.
• How willing is leadership to pay to remove these hidden costs vs. tolerate them for short-term cash preservation? Options: Highly willing, Somewhat willing, Only with strong ROI case, Prefer to delay

Who Really Decides — and Who’s Quietly Resisting?

• If the program were paused today, who in your organization would most forcefully argue to continue—and who would quietly push back?
• Which roles or groups will need to sign off on technical architecture, functional scope, commercial terms, and go/no-go decisions? Options: CIO/CTO, CFO, Business Unit Heads, Procurement, Security/Compliance, Line-of-business operations, Other
• Which stakeholder groups tend to underestimate the change impact on people and why (give a recent example if possible)?
• How are you currently engaging internal change agents—do you have named process owners, data owners, and adoption champions? Options: All identified and engaged, Some identified, limited engagement, Not yet identified, Unsure
• What would make your most skeptical stakeholder shift from resisting to supporting the program? Options: Clear ROI/benefit case, Proof-of-concept or pilot, Reference from similar peer, Low-risk phased approach, Guaranteed support and training

What Would 'No Surprises' Look Like?

• What single piece of evidence would satisfy your board or CFO that this program will avoid the ‘surprise’ outcomes you fear?
• Which of these delivery guarantees would increase your confidence the most? Options: Fixed-price milestones, Time-and-materials with cap, Stage-gated approvals, Performance SLAs, Guaranteed consultant seniority
• What is your acceptable threshold for cost variance and schedule variance before you expect an executive-level escalation? Options: <5%, 5–10%, 10–20%, >20%
• How frequently do you want formal program status and risk reviews once a project is underway? Options: Weekly, Bi-weekly, Monthly, Only at major milestones
• Which artifacts or checkpoints would make you comfortable proceeding from discovery into design (pick top three)? Options: Executive decision matrix, Detailed business process map, Data readiness assessment, Validated staffing plan, Realistic cutover plan and runbook, Commercial milestone schedule

Data: Truths, Myths, and Loose Ends

• When you think about data quality and migration, what single nightmare scenario do you most want to prevent?
• Which data domains require the most attention for migration and governance? Options: Master data (items, customers, vendors), Financial balances, Historical transactions, Bills of material / routings, Employee and payroll data, Other
• Roughly how many integrations touch the ERP now (including batch extracts), and which are highest risk to migrate? Options: 0–5, 6–15, 16–50, >50, Unsure—need discovery
• Do you have named data owners and documented data quality SLAs (if yes, point to the most recent gap)? Options: Yes—owners and SLAs, Partial—owners only, No formal owners/SLAs, Unsure
• Would you prefer a big-bang migration, a hybrid phased approach, or a nearline coexistence strategy for high-risk domains? Options: Big-bang, Phased by module/region, Hybrid (parallel for critical domains), Nearline coexistence, Undecided—need guidance

Cutover Night — Plan, Panic, or Performance?

• Imagine go-live night goes wrong—what single failure would be catastrophic for your business continuity?
• What maximum downtime window is acceptable for core transactional systems during cutover? Options: <2 hours, 2–8 hours, 8–24 hours, 24–72 hours, Cannot accept downtime
• Which roles must be physically or virtually present in the cutover command center? Options: Program Director, Technical Architect, Business Process Owner, Data Migration Lead, Security/Network, Executive on-call
• Have you run full end-to-end dress rehearsals for cutover before, and if so, what went wrong most recently? Options: Yes—multiple, with learnings, One full dress rehearsal, Partial simulations only, No full rehearsals
• What contingency would you insist on including in the cutover plan to sleep at night (e.g., rollback plan, parallel processing, buffer days)? Options: Rollback plan, Parallel backstop, Extended hypercare, Phased switchovers, Additional vendor staffing

Measuring Success — What Will Make You Smile?

• Three months after go-live, what would you want to be able to say to the board that proves success?
• Which KPIs should we track and report from day one to demonstrate value? Options: Invoice cycle time, Days sales outstanding (DSO), Inventory accuracy, Order lead time, First-pass quality, User adoption rates, System availability
• What adoption targets would make you confident the organization has embraced the new system (select ranges)? Options: >90% active users on new system, 75–90%, 50–75%, <50%
• How long of a hypercare window do you anticipate needing after go-live, and what would justify extending it? Options: 2 weeks, 4 weeks, 8–12 weeks, Quarterly phased hypercare
• What would you like us to capture as the single most important lesson learned at the end of the program?