Getting Comfortable — Who’s Actually in the Room?

• Who is the single person who will make the final decision on a core conversion (name and title)?
• Which roles will influence that decision? (select all who will actively participate) Options: CEO/President, CFO/VP Finance, Head of Operations/COO, Board Chair/Board Members, Head of IT/Interim IT Manager, Compliance Officer, External Consultant/Advisor, Other
• Who currently owns day-to-day responsibility for your core vendor relationship and conversion logistics (name/title)?
• How do these stakeholders prefer to evaluate risk and evidence? (pick the top two) Options: Quantitative metrics & SLAs, Reference calls & case studies, Pilot/parallel testing results, Regulator/examiner sign-off, Board narrative and risk analysis, Legal/contract protections
• When there’s disagreement among these stakeholders, whose view tends to win—practical operations, financial analysis, or board governance? Options: Operations/practical, Financial/CFO analysis, Board/governance, Compliance/regulatory, Depends on the issue

If the Cutover Freezes Tellers, Who Sleeps Worse at Night?

• Describe the single worst thing you fear happening during a conversion and why it would be catastrophic for your institution.
• Which of these outcomes would be most damaging to your reputation or operations (select one)? Options: Extended branch/teller outage, Account balance errors, Failed regulatory reporting, Mass customer attrition, Data breach/exposure, Other
• How much downtime during cutover would you consider unacceptable (choose the maximum acceptable window)? Options: Under 1 hour, 1–4 hours, 4–12 hours, 12–24 hours, More than 24 hours
• If a conversion caused an outage or material error, how do you expect the board and examiners would respond?
• What emotional impact do these risks have on your leadership team—are they paralyzed, conservative, eager for change, or something else? Options: Paralyzed/avoidant, Conservative/slow to change, Open but cautious, Eager to move quickly, Mixed emotions across team

Decision Timeline — Are We on a Deadline or Kicking the Can?

• What is your target decision date for choosing a new core provider (month/year)? Options: Within 30 days, Within 2–3 months, Within 4–6 months, 6–12 months, No firm date/undecided
• What contractual or examiner deadlines force this timeline (select all that apply)? Options: Contract expiry with current vendor, Examiner finding deadline, Board meeting schedule, Regulatory reporting cycle, Acquirer or merger timeline, None formal—internal driver
• What are the three non-negotiable milestones that must happen before the board will vote to approve a conversion?
• If the timeline slips by 3 months, what consequences would you expect (operational, financial, regulatory)?
• Who controls scheduling of the pilot/parallel processing window and board packet timing? Options: CEO/President, CFO, Operations/COO, Board Secretary/Chair, External Advisor, Vendor collaborative scheduling, Other

What Will Make the Board Say Yes (and Sleep Easy)?

• What single performance metric or proof point would make your board comfortable approving the conversion?
• Which evidence types would the board accept as credible (select all that would carry weight)? Options: Conversion runbooks and playbooks, Third-party uptime/conversion audits, Reference site visits with similar institutions, Pilot parallel-processing results, Regulator/examiner letters of support, Financial TCO analysis
• What minimum uptime guarantee do you require in contract terms to present to the board? Options: 99.9%, 99.95%, 99.99%, Higher—specify in comments, No specific number yet
• What contractual protections would your legal/board insist on (select all that apply)? Options: Conversion completion guarantees, Financial penalties for extended downtime, Data integrity indemnities, Rollback/restore commitments, Regulatory compliance indemnity, Insurance/escrow
• Are there specific board members or examiners whose approval is decisive? If so, what concerns do they always raise?

What Control Gaps Do We Have to Close Before Anyone Signs?

• What outstanding examiner findings, audit issues, or internal control gaps must be resolved or mitigated as part of a conversion?
• Who will be accountable for validating data conversion accuracy—internal teams, vendor, or a joint task force? Options: Internal operations/IT team, Vendor conversion team, Joint vendor/internal validation team, External auditor/consultant, Other
• What reconciliation and acceptance tests will you require before approving go-live (select all that apply)? Options: Trial balance reconciliation, Deposit test suites, Regulatory report matching, Aging loan schedule validation, Customer account sampling, End-to-end transaction flow tests
• How would you like remediation documented if a conversion test fails (options for evidence)? Options: Root-cause report + fix plan, Re-run test evidence, Third-party validation, Formal change-control sign-off, Other
• What level of audit trail or documentation does your board/examiner require to demonstrate controls were followed? Options: High-detail technical logs, Executive summary + key logs, Signed checklists and approvals, Third-party attestation, Not sure—need guidance

People, Capacity, and Who Will Run the Pilot

• How many full-time internal staff (by role) can you dedicate to the conversion over the next 6–12 months? Please list counts by role.
• Who will be the operational lead for the parallel-processing pilot (name and role)?
• Which of these best describes your team’s experience with full core conversions? Options: Led multiple conversions, Participated in one conversion, Observed conversions externally, No direct conversion experience
• What training cadence and format do you prefer for staff during migration (select all that apply)? Options: Instructor-led workshops, On-demand video modules, Hands-on shadowing during pilot, Written runbooks and quick-reference guides, Train-the-trainer model
• What is the single biggest people-related risk that could derail your pilot or go-live?

How Do We Tell the Story Up the Chain?

• What format convinces your board most—concise executive risk memo, slide deck with data, technical appendix, or a live demo/report-back? Options: Executive memo, Slide deck + appendix, Live demo with Q&A, Pilot report with metrics, Combination of the above
• Which metrics and narrative points must appear in the board packet to make approval likely (top 5)?
• How much lead time do you need to prepare board materials prior to a scheduled meeting? Options: Less than 1 week, 1–2 weeks, 2–4 weeks, More than 4 weeks
• Have previous board presentations about vendor changes uncovered recurring objections or language we should preemptively address? If yes, summarize.
• Would you like a vendor-provided board-ready summary/template we can adapt for your packet? Options: Yes—highly useful, Maybe—depends on length, No—we’ll produce our own

Start Here: The Story Behind Your Trigger

• What prompted you to start evaluating your core now? Options: Examiner finding, Loss of key IT staff, Vendor acquisition/merger, Contract renewal/expiry, Performance or reliability issues, Other
• Can you briefly describe the specific event or feedback that triggered this initiative?
• When did the triggering event occur? Options: Within the last 30 days, 1–3 months ago, 3–6 months ago, 6–12 months ago, 12+ months ago
• Who first raised the concern internally (select all that apply)? Options: CEO, CFO, COO/Operations, Compliance/Chief Risk Officer, Board member, IT Manager/Staff, Other
• How urgent does the board view making a change to the core? Options: Immediate (0–3 months), Near term (3–6 months), Planned (6–12 months), Not urgent / exploratory
• What would be an immediate dealbreaker for your team that would stop a migration in its tracks? Options: Extended downtime beyond acceptable window, Regulatory disapproval, Data loss or balance discrepancies, Cost exceeds approved budget, Vendor lacks comparable references, Other

If This Fails, What Keeps You Awake?

• If our conversion caused the teller line to freeze for even a few hours, what would that mean for your bank?
• Which of these worst-case impacts concern you most? Options: Customer attrition / lost deposits, Regulatory sanctions or fines, Significant financial loss, Reputational damage in the community, Legal claims or lawsuits, Other
• Have you experienced a past outage, conversion problem, or near-miss? Tell us what happened and the aftermath.
• How tolerant are your examiners and board for temporary operational disruption? Options: Zero tolerance – would escalate immediately, Low tolerance – requires formal remediation, Moderate tolerance with strong communication, High tolerance – willing to accept temporary issues
• Which customer segments would be most harmed by transaction or balance errors? Options: Retail depositors, Commercial / business clients, Mortgage customers, Treasury / corporate clients, High-net-worth clients, Other
• Estimate in your own words how a loss of trust would manifest financially or operationally (percent deposits lost, penalties, customer complaints, etc.).

Where the Backbone Lives: Systems, Integrations & Shadow Tech

• What critical systems or hidden tools must keep talking to your core for day-to-day operations to continue?
• Which third-party systems integrate with your core right now? (select all that apply) Options: Digital/mobile banking, ATM/POS network, ACH processor, Wire processor, Loan Origination System (LOS), Card processing, Check imaging, Fraud/AML system, Treasury/ERP/GL, CRM, Other
• Which integrations are real-time versus batch? Please list or describe any mixed modes.
• Do you have any custom middleware, one-off scripts, or manual workarounds that keep integrations functioning? Options: Yes – many customizations, A few targeted workarounds, No – mostly standard connectors, Unsure
• Are there vendor contracts or SLAs that could prevent data extraction or real-time connectivity during conversion? Options: Yes – explicit constraints, Possibly – need to review contracts, No constraints known, Unsure
• Are there 'shadow IT' systems or spreadsheets teams rely on that we should know about?

Data Truths: Where the Records Tell the Real Story

• If you had to bet on one single data risk that could derail cutover, what would it be?
• How complete is your current data inventory (accounts, transactions, fees, custom fields)? Options: Comprehensive and well-documented, Mostly documented with some gaps, Fragmented across teams, No single inventory exists
• Which data sets fail reconciliation most frequently? Options: Deposit balances, Loan balances and accruals, Pending ACH/wires, Fees and interest calculations, Customer identifiers/KYC, Historical transaction history, Other
• How long does it currently take to produce a regulatory-grade extract or reconciliation report for auditors? Options: Days, Weeks, 1–2 months, Longer than 2 months, Unsure
• Do you have sample data sets or a sanitized test environment we can use? Describe access restrictions or masking needs.
• Are there known 'poison pill' records or formats that repeatedly break systems (examples, legacy account types, unicode issues, negative balances)?

Examiner Red Lines and the Papers That Calm Them

• What specific examiner findings, audit expectations, or regulator behaviors would make them say 'not approved' for a migration?
• List any open examiner findings, audit items, or regulatory concerns tied to IT, disaster recovery, or third-party risk.
• Which pieces of evidence have previously satisfied examiners in similar projects? (select all that apply) Options: Parallel processing reports, Full reconciliation logs, Third-party validation/attestations, Board-ready risk/mitigation materials, Runbooks and test scripts, Other
• Who is our regulator-facing contact internally, and what communications cadence do they expect during a migration? Options: Internal compliance handles communications, We coordinate jointly with compliance, You (vendor) will engage directly with regulator, Unsure
• Have regulators required a pilot or parallel run in the past? If so, what acceptance criteria did they require?
• What board-level documents or metrics are non-negotiable to secure approval?

People, Power, and Who Pulls the Levers

• Who in your organization has the power to halt or veto the migration, and what typically influences their decision?
• Please provide names/roles for the decision owners (CEO, CFO, Operations lead) and who will own day-to-day conversion choices.
• Which internal teams must be staffed during cutover? (select all that apply) Options: Core operations, Deposits team, Loan operations, IT/Infrastructure, Compliance/Risk, Fraud/AML, Customer service/Contact center, Treasury/Finance/GL, Vendor management, Other
• How much time can your subject matter experts realistically devote during peak conversion weeks? Options: Full-time (40+ hrs/week), Mostly full-time (20–40 hrs/week), Part-time (10–20 hrs/week), Limited (a few hours/week), On-call only
• What cultural or organizational blockers should we expect (risk aversion, siloed teams, vendor mistrust, lack of documentation)?
• Who should be on a short steering committee empowered to remove roadblocks and approve scope changes?

What Past Conversions Taught You (Or Failed to)

• What near-miss, past migration, or vendor engagement still makes you nervous today?
• Have you ever paused or rolled back a production cutover? If yes, what were the causes and the fixes? Options: Yes – rollback, Yes – paused but recovered, No, N/A
• How do you verify a vendor's conversion track record when evaluating partners? Options: Customer references and site visits, SLA and uptime history, Third-party audits/attestations, Pilot performance, Public case studies, Other
• Which metrics from previous conversions most convinced your board or examiners that risk was controlled? Options: Uptime percentage during cutover, Reconciliation completeness, Number of incidents and time-to-resolution, Customer impact measured by complaints, Regulatory reporting parity
• What runbooks, playbooks, or emergency checklists do you currently have, and where are the biggest gaps?
• Would you be open to a joint tabletop or simulated cutover exercise before a live pilot? Why or why not? Options: Yes – mandatory before pilot, Yes – optional, No – not useful, Unsure

Acceptance Before the Cut: What 'Good' Looks Like

• If the board demanded 99.9% uptime and zero regulatory gaps, what evidence would you need from a pilot to feel safe?
• Which measurable success signals must be proven in a pilot? (select all that apply) Options: Conversion completeness (no missing accounts), No account balance drift, Regulatory report parity, Transaction latency and throughput targets, Successful parallel processing for defined period, Customer service SLA maintained, Other
• What is your acceptable window for parallel processing duration during transition? Options: Less than 1 month, 1–3 months, 3–6 months, 6–18 months
• Do you require contractual conversion guarantees (e.g., uptime SLA, financial remediation)? If yes, please specify thresholds.
• What dashboards, executive summaries, or artifacts will the board require during pilot and cutover? Options: Real-time reconciliation dashboard, Issue tracker with SLAs, Daily executive summary, Audit logs and change history, Third-party validation reports, Other
• Who signs off on pilot acceptance and final cutover approval at the executive and board levels?

Priorities Today: What to Lock Down First

• If I told you we could fix one thing in 30 days to materially reduce conversion risk, which would you choose?
• Select up to your top 3 immediate priorities you'd like us to address (we'll use this to draft a 30/60/90 plan). Options: Formalize stakeholder decision roles, Inventory integrations and SLAs, Produce regulatory-grade extracts, Establish a parallel processing environment, Remediate known data poison pills, Secure third-party connectivity, Staffing plan and on-call rosters, Board-ready migration and risk materials
• Which of those priorities are already budgeted or resourced? Options: Fully budgeted, Partially budgeted, Not yet budgeted, Awaiting approval, Unsure
• What material constraints (time, budget, vendor approvals, staff availability) would prevent quick progress on your top priorities?
• Who should be on a short, empowered steering committee to clear blockers and make rapid decisions?
• Would you like us to draft a prioritized 30/60/90 day mitigation plan and a list of required artifacts for your board and examiners? Options: Yes – please draft and include templates, Maybe – need internal signoff first, No – we will draft internally, Unsure

A Quick Check Before We Roll In

• In one sentence, what outcome would make this deployment feel successful to you and satisfy the board?
• What specific cutover weekend(s) or date ranges are you targeting today? Options: Next 30 days, 30–60 days, 60–90 days, 3–6 months, Unscheduled / flexible
• Tell us about any past conversions or DR events that still shape how you think about risk for this migration.
• Who in your organization will have final sign-off authority on go/no-go (name and role)?
• What is your maximum acceptable customer-facing downtime during cutover (choose the closest) Options: < 15 minutes, 15–60 minutes, 1–2 hours, 2–4 hours, No maximum tolerated (must be zero)

Who's in the Room When It Counts?

• If your CEO or board asked today, 'Why won’t this cutover freeze teller lines?', what single, credible answer would you give?
• List the decision roles we should expect to engage during readiness and cutover (select all who apply). Options: CEO / Board Chair, CFO, COO / Operations, Head of Retail/Branches, IT Director / CIO, Compliance Officer, Vendor Relationship Manager, Other
• For each role you selected, how available will they be during the cutover window (hours per day / on-call)? Options: Dedicated on-site / full availability, On-call but remote, Limited availability (business hours only), Not available
• Who is the backup for your recently departed IT manager, and how long have they been in that role?
• How do you prefer escalation to be handled during an incident (single contact, tiered, committee, other)? Options: Single executive contact, Tiered technical then executive, Emergency committee/war room, Automated escalation with rotation, Other

Your Data — Not Just Files but Lifelines

• What would you do if a sample extract showed account balance mismatches on 0.1% of accounts—pause and investigate, proceed with fixes, or other? Options: Pause all progress and investigate immediately, Proceed but isolate and fix discrepant records, Accept and remediate post-cutover, Other
• Which data extracts have been completed and validated so far (select all that apply)? Options: Customer master / ID files, Account balances and ledgers, Transaction history (X years), Loan files and amortization schedules, ACH / wires history, Collateral and lien records, None yet
• What format do your current extracts use and how consistent are they across channels? Options: Fixed-width flat files, CSV / delimited, XML / JSON, Database snapshots / SQL dumps, Mixed formats / inconsistent
• Describe your current reconciliation cadence and who owns day‑to‑day reconciliation during testing.
• What data quality thresholds must be met before migration (e.g., % of accounts with verified balances, missing fields allowed)?

Third-Party Glue and Where It Breaks

• Which single third-party integration failing during cutover would cause the most customer impact—and why?
• Please identify all critical external vendors and integrations we must test end-to-end (select all that apply). Options: Digital banking provider, ATM network, Card processor / switch, ACH operator, Wire correspondent, Fraud/AML vendor, Check clearing / image processor, Other
• Which of those vendors have completed formal connectivity testing with your extract/test environment? Options: All completed, Most completed, Some completed, None completed
• Who is the vendor contact and SLA owner for each critical integration, and do we have escalation contacts?
• If a vendor fails during cutover, which contingency should we trigger first (rollback, manual workaround, queued processing, other)? Options: Rollback to prior system, Manual workarounds with staff, Queue transactions for delayed processing, Temporary service substitution, Other

Dry Runs, Test Data and Pilot Confidence

• If the parallel-processing pilot gave us 100% green lights but masked a rare edge case, how would we detect that before go-live?
• Which pilot scenarios must be executed and validated before go/no-go (select all that apply)? Options: End-of-day balancing, ACH processing day, Wire day, Loan posting and interest accrual, Regulatory reports generation, High-volume teller day, Dispute/resolution flows
• What sample size or transaction volume will you use in parallel processing to feel confident (percentage of daily volume or absolute transactions)? Options: <1% sample, 1–10% volume, 10–50% volume, Full production volume for a window
• How many full-dress dry runs have you completed and when was the last one? Options: None yet, 1, 2–3, 4 or more
• Who owns test sign-off for each pilot scenario and what evidence do they require (logs, reconciliations, screenshots)?

People Power: Who Will Run the Weekend

• If a critical process fails at 2 a.m. on cutover day, who are we absolutely confident will be awake and fixing it—and why?
• Please map the core roles that will be staffed during cutover and indicate whether they will be on-site, remote, or on-call (select role then location). Options: On-site, Remote with guaranteed connectivity, On-call only, Not staffed
• Do you plan to use contracted/temporary staff for extended hours during cutover, or rely solely on internal teams? Options: Internal teams only, Use contractors for overflow, Hybrid approach, Undecided
• Who owns the runbooks and playbooks, and are they version-controlled and accessible to escalation teams? Options: Yes, centralized and versioned, Yes, but multiple copies, Drafts exist, No documented runbooks
• What training has branch and frontline staff completed on the new workflows, and what gaps remain?

Regulators, Boards and the Paper Trail

• If an examiner arrived the morning after cutover, what single document would convince them we mitigated conversion risk?
• Which regulator and board notifications are required before (or immediately after) cutover? Options: Primary regulator pre-notification, Primary regulator post-cutover report, Board briefing package pre-cutover, Board post-cutover acceptance, None required / not sure
• Are there any open examiner findings or outstanding compliance issues that must be resolved or disclosed as part of the readiness checklist? Options: No open findings, Open findings unrelated to conversion, Open findings relevant to conversion, Unsure / need to verify
• Who will coordinate regulatory questions during the first 30 days post-cutover, and what is their contact protocol?
• What formatted board-ready materials do you expect us to provide (select all required)? Options: Risk assessment memo, Cutover timeline and gates, Contingency plans, Proof of pilot results, SLA and uptime guarantees, Other

The Go/No-Go Moment — Gates That Protect the Bank

• What's the single condition that would make you say 'no' at the final gate even if everything else appears green?
• Which objective metrics must be met to pass the final go/no-go gate (select all that apply)? Options: Zero unreconciled balances, All critical integrations online, Pilot processing at X% volume, Regulatory notifications acknowledged, Staffing confirmed
• Who holds the authority to trigger rollback and who must be notified within 15 minutes of that decision?
• Describe the communication plan for customers and staff if we delay or abort cutover (templates, channels, timing).
• What timing and format do you require for final sign-off (e.g., live call, signed checklist, board approval)? Options: Live executive call + documented checklist, Signed digital checklist, Board-approved resolution, Email confirmation from authority

Final Confidence Check — What Would Make You Sleep Better?

• Aside from technical readiness, what single human concern makes you the most anxious about the upcoming deployment?
• Which assurance from us would most reduce that anxiety (examples: guaranteed conversion SLA, extra on-site staff, extended parallel window)? Options: Conversion uptime SLA (99.9%+), Guaranteed remediation window, Additional on-site support, Longer parallel processing, Regulatory-ready documentation
• What would you like our team to proactively own and report on daily during the 14 days leading to cutover? Options: Extract & validation status, Integration test progress, Staffing confirmations, Pilot results summary, Risk register updates
• If you could ask one question of your board about this migration and get a candid answer, what would it be?
• Is there anything else we should know right now that would change how we approach pre-deployment readiness?

Tell Us What Brought You Here (briefly)

• In one or two sentences, what exact event or concern prompted you to explore replacing or updating your core today?
• Who first raised the issue inside your institution—CEO, CFO, operations, board, or an examiner—and what did they say? Options: CEO, CFO, Operations/COO, Board member, Examiner/regulator, IT manager, Other
• How urgent does this feel on a scale from 'nice to fix' to 'board/examiner action required'? Options: Board/examiner action required, High priority for leadership, Important but not urgent, Watchlist for future planning
• What would you like us to understand first about your situation that might not be obvious from documents or vendor logs?

Are You Comfortable Leaving Core Risk to Assumption?

• If your current conversion plan assumed 'no downtime over cutover weekend,' what would you say is most likely to break that assumption?
• Which of these single points of failure feels closest to reality for you right now? Options: Data conversion rules, ACH/External integrations, Teller capture continuity, Regulatory reporting runs, Staffing during cutover, Rollback capability, Other
• How long have these risks been tolerated in your environment—weeks, months, years? Options: Weeks, Months, 1–3 years, 3–10 years, 10+ years
• Tell us about a time when a trusted assumption about your systems failed; what happened and what did it cost you (time, reputation, money)?

Who Really Decides—and What Keeps Them Up at Night?

• You may think the CEO owns the decision, but who actually signs off on go/no-go during a conversion weekend? Options: CEO, CFO, COO/Operations, Board chair, Chief Risk/Compliance Officer, Examiner sign-off required, Other
• What specific approval criteria would the board or examiner need to see to feel comfortable (examples: zero-balance mismatches, signed SLAs, pilot acceptance)? Options: Balance reconciliation proof, Conversion guarantees, SLA uptime history, Third-party readiness attestations, Pilot parallel-processing results, Regulatory notification plan, Other
• Which one metric would immediately make the CEO breathe easier: conversion uptime, TCO over seven years, minimal customer complaints, or something else? Options: Conversion uptime, 7-year TCO, Customer complaint volume, Regulatory findings eliminated, Staff time saved, Other
• How emotionally prepared is your leadership to defend a decision if the migration faces short-term customer friction? Options: Very prepared, Somewhat prepared, Not prepared, Undecided

The Moments That Actually Make Customers Leave (and How You’ve Seen Them)

• Which customer-facing failures do you fear most during conversion—frozen teller lines, missing balances, failed ACH, or delayed online access? Options: Frozen teller lines, Account balance errors, ACH/Wire failures, Online/mobile outages, Statement/reporting errors, Other
• Have you ever had a customer escalate a core-related issue to the board or local press? What happened and how was it resolved?
• How many accounts or transactions would you consider 'critical' to validate during cutover to avoid depositor flight? Options: Top 100 accounts, Top 1,000 accounts, All commercial accounts, All accounts over $X, All accounts (full validation)
• If a worst-case scenario occurred and you lost teller capability for 12 hours, what immediate actions would you expect from your vendor partner?

What 'Successful Conversion' Actually Looks and Feels Like

• Imagine the board signs off after cutover—what three concrete outcomes did they see that convinced them to approve?
• Which of these acceptance criteria must be met for you to call the conversion successful? Options: Zero reconciled balance differences, 99.9%+ uptime observed, Regulatory reports run correctly, Customer-facing channels fully functional, Parallel processing pilot acceptance, Other
• How will you measure seven-year TCO success—what line items matter most (processing fees, staffing, third-party licenses, risk remediation)? Options: Processing fees, Staffing costs, Third-party licenses/integrations, Compliance/regulatory costs, Hardware/hosting savings, Other
• Beyond metrics, what would it feel like to your leadership team to have a 'no-surprises' conversion in terms of stress, media risk, and board relations? Options: Relief and confidence, Cautious optimism, Skeptical but satisfied, No change

How Your Data and Integrations Really Live Today

• If I asked your senior developer to map your core data flows right now, how complete would that map be? Options: Complete and documented, Mostly documented with gaps, Fragmented across teams, Undocumented/tribal knowledge
• Which external systems must remain uninterrupted during migration (select all that apply)? Options: Digital banking vendor, ATM/network provider, ACH processor, Loan origination system, POS/merchant services, General ledger, Regulatory reporting bureau, Other
• Have you run a reconciliation between your current core and any backups/test extracts recently—when and what did you find? Options: Within last month, 1–6 months ago, 6–12 months ago, Over a year ago, Never
• Which data quality issues keep you awake (duplicate accounts, stale balances, misposted fees, missing ACH history, other)? Options: Duplicate accounts, Stale balances, Misposted fees, Incomplete transaction history, Missing third-party references, Other

Regulators, Examiners, and the Board: What They’ll Want to See

• If an examiner asked for evidence that migration risk is mitigated, what three documents or proofs would you want to present?
• Which of these regulatory concerns is most pressing for you right now? Options: Disaster recovery documentation, Data integrity proofs, Change management logs, Vendor oversight evidence, Timely regulatory report delivery, Other
• How comfortable are you with having board-level materials prepared that explain conversion risks and mitigations in plain language? Options: Very comfortable, Somewhat comfortable, Need help from vendor, Not comfortable at all
• Have previous regulatory findings influenced your timeline or level of due diligence—if so, how?

Pilot Reality Check: Parallel-Processing and Acceptance

• What would a successful parallel-processing pilot have to prove to your operations team? Options: Matching balances, Timely posting, Customer channel parity, Exception counts below X, Regulatory report parity, Other
• How long could your operations team realistically run parallel processing without unacceptable strain? Options: 2–4 weeks, 1–3 months, 3–6 months, 6–18 months, Unsure
• Who in your organization will be responsible for signing off on pilot acceptance and what criteria will they each demand? Options: CEO, CFO, COO, Head of Operations, Compliance Officer, Board representative, Other
• What successes or failures from past pilots should we know about so we can design a realistic pilot together?

Decision Practicalities: Timeline, Budget, and Non-Negotiables

• If the vendor delivered a guaranteed 99.9%+ uptime during conversion, would that change your willingness to proceed? Options: Yes—significantly, Somewhat, No change, Depends on proof
• What budget horizon do you evaluate TCO over—7 years, 10 years, or a different timeframe? Options: 7 years, 10 years, 5 years, Other
• Which contractual terms are absolute deal-breakers for you (select up to three)? Options: Conversion uptime guarantee, Financial conversion guarantees, Regulatory compliance indemnity, SLA severity/credits, Board-ready documentation, Vendor exit assistance, Other
• How do you want vendors to demonstrate their historical conversion uptime for similarly sized institutions—logs, third-party attestation, or reference calls? Options: System logs/metrics, Third-party attestation, Customer reference calls, Case studies with data, All of the above
• Realistically, what's your internal deadline to have a vendor decision in front of the board? Options: Immediate (this month), 30–60 days, 60–120 days, 6+ months, No firm deadline

Who Will Do the Work—and Do They Have the Bandwidth?

• If we mapped every role needed for conversion (project lead, data analysts, 24/7 support, teller trainers), which roles are already staffed and which would you expect us to provide? Options: All staffed internally, Most staffed; need vendor support, Critical roles missing, Expect vendor to supply all roles
• How many internal FTEs can realistically be dedicated to conversion during peak windows without jeopardizing day-to-day operations? Options: 1–2, 3–5, 6–10, 10+, None available
• What level of vendor-led training and documentation would make your staff feel confident post-cutover? Options: Hands-on classroom, Recorded sessions + docs, Train-the-trainer, Shadowing during pilot, On-call vendor support
• Which internal team tends to be the hardest to align during projects like this—and why? Options: IT, Operations, Compliance, Finance/CFO, Customer service, Other

Red Flags and Deal Breakers: Tell Us Early

• What absolute red flags would stop you from moving forward with a vendor at any point during diligence? Options: No conversion guarantees, Lack of references, Poor regulator engagement, Insufficient data controls, No rollback plan, Other
• Have you walked away from a vendor before? If yes, what single issue caused that decision? Options: Yes—security/compliance, Yes—poor conversion plan, Yes—cost, Yes—cultural fit, No, never
• How would you like us to surface concerns during discovery so you feel heard—weekly checkpoint, written risk register, or an executive summary? Options: Weekly checkpoints, Written risk register, Executive summary for leadership, Ad hoc conversations, All of the above
• What would restore your confidence in a vendor if an issue emerged late in the process? Options: Rapid remediation plan, Financial compensation, Public commitments to board, Third-party validation, Demonstrated successful rollback, Other

Next Steps Together: What Would Make This Conversation Valuable

• Which artifacts would you like from us next—a tailored migration roadmap, pilot design, TCO model, or board-ready summary? Options: Tailored migration roadmap, Pilot design and success criteria, 7-year TCO model, Board-ready presentation, Regulatory notification checklist, All of the above
• Who else on your team should be part of the next conversation to avoid surprises later? Options: CEO, CFO, COO/Operations, Head of IT, Compliance Officer, Board representative, Other
• What would make you decide to continue exploring our solution after this discovery call? Options: Clear risk mitigation plan, Proof of 99.9%+ conversion uptime, Satisfactory pilot plan, Acceptable TCO estimate, Board materials ready, Other
• When would you like us to present our proposed next-step materials? Options: Within 1 week, 1–2 weeks, 2–4 weeks, After internal review, Undecided