Start with the Story: Tell Us the Near-Miss

• In a sentence or two, tell us what happened with the most recent late filing or resubmission that sparked this project.
• Which filing(s) were involved in that incident? Options: Quarterly NAIC statutory statement, Annual statutory statement, Schedule P / loss triangles, Call Report, SEC/10-Q or 10-K, Other
• When was the failure first discovered relative to the filing deadline? Options: More than 2 weeks before, 1–2 weeks before, 2–7 days before, Less than 48 hours before, After submission
• Who initially flagged the issue? Options: Compliance/CCO, Controller, Single analyst, External auditor, Regulator, Other
• What immediate regulatory response did you receive (if any)? Options: Letter of inquiry, Request for resubmission, Fine or penalty, Informal inquiry, No formal response yet, Other
• Estimate the tangible and intangible impacts this incident caused (time, cost, reputation). If unknown, describe what you suspect. Options: <$50k, $50k–$250k, $250k–$1M, >$1M, Primarily reputational/operational

If This Keeps Happening, What Breaks First?

• Imagine the same fragility persists for the next 12 months—what outcome would be most damaging to the business or license? Options: Formal regulatory examination, Material restatement, Loss of rating, Major client or broker fallout, Financial penalty, Other
• How often have you experienced filing near-misses or significant reconciliation failures in the past two years? Options: Monthly, Quarterly, Annually, Rarely (once in 2+ years), This was the first
• How dependent is your current process on individual knowledge or a single person? Options: Critical single-person dependency, High dependency but some backup, Moderate dependency, Low dependency
• Which parts of the filing workflow feel most fragile right now (pick all that apply)? Options: Data extraction from source systems, Manual mapping into templates, Cross-schedule reconciliations, Validation and rule checks, Sign-off and governance, Submission process
• Tell us about one example where a known weakness almost caused a material issue—what went wrong and why?

Who Holds the Keys — and Who’s Accountable?

• Who in your organization will ultimately sign off on filing accuracy and accept the residual risk? Options: CFO, Controller, CCO, Head of Regulatory Affairs, Board committee
• Who is sponsoring this initiative and who will hold the budget authority to approve investments? Options: Chief Compliance Officer, Controller, CFO, CIO, Other
• Which stakeholders must be engaged during discovery and mapping (select all that should be part of working sessions)? Options: Policy administration owner, Investment accounting owner, General ledger / FP&A, IT / Integration, Internal audit, Legal / Reg Affairs, External auditors
• How would you describe your regulator’s tolerance for late filings or resubmissions today? Options: Very low – immediate escalation, Low – formal inquiry likely, Moderate – depends on context, High – informal handling common, Unsure
• Are there mandatory internal governance gates (committees, sign-offs) we should plan around? If yes, who and how often do they meet?

Where Your Data Actually Lives (and Who Owns It)

• Do you have a single authoritative source for each data domain required for filing (policies, claims, investments, GL)? Options: Yes, clearly defined, Mostly, with exceptions, No, fragmented across systems, Unsure
• Which source systems feed your filings today (select all that apply)? Options: Policy Admin System(s), Claims warehouse, Investment accounting system, General ledger / ERP, Reinsurance system, CRM/Underwriting systems, Custom data marts
• Who currently owns each data feed or schedule in your organization? Please list system → owner pairs or explain if ownership is ambiguous.
• Are sample datasets and historical filings readily available for testing and baseline validation? Options: Yes – full datasets available, Partial samples exist, Only aggregate outputs available, Not available
• What common data quality issues do you regularly encounter (pick all that apply)? Options: Missing fields, Duplications, Inconsistent identifiers, Timing mismatches, Currency/valuation differences, Other

Show Me the Broken Process — Step by Step

• Walk us through the current end-to-end process you follow from data extraction to regulator submission.
• Which tools are central to the current workflow (select all that apply)? Options: Excel / spreadsheets, BI tools (Tableau/PowerBI), Homegrown scripts, ETL platform, Regulatory filing software, Manual PDF/Word templates
• How long does the typical filing cycle take from data pull to submission? Options: <1 week, 1–2 weeks, 2–4 weeks, >1 month
• When you performed the last reconciliation, where were the most time-consuming tie-outs or manual adjustments made?
• Who is responsible for maintaining the mapping logic today, and how is that change-managed or documented? Options: Single analyst, Small team (2–4), Cross-functional team, No clear owner / ad-hoc

What Would 'Not Worth Another Regulator Letter' Actually Feel Like?

• If you could guarantee one outcome that would restore comfort to leadership, what would it be and why?
• Which of these measurable success signals matter most to you (pick top three)? Options: Zero late filings, Automated cross-schedule reconciliations, Repeatable audit trails, Faster close-to-file cycle time, Fewer manual adjustments, Reduced single-person dependency
• What level of residual risk would be acceptable after automation (pick one)? Options: Negligible (near-zero), Low (tolerable with exception handling), Moderate (requires oversight), Uncertain—need to discuss
• How quickly do you need to see demonstrable improvement to feel confident (pilot, POC, or production timeline)? Options: Immediate (within 30 days), Short (30–90 days), Medium (3–6 months), Longer (>6 months)
• Who on your team needs to feel the benefits first to onboard the rest of the organization? Options: Controller team, Compliance/CCO, IT/Integration, Finance leadership, Audit/Legal

What Could Stop This Change From Working?

• What doubts or objections would you expect from your peers if we proposed automating mappings and validation? Options: Accuracy concerns, Loss of manual controls, Regulatory acceptance, Integration complexity, Cost/budget
• Which implementation risks worry you most (select up to three)? Options: Mapping errors producing inaccurate filings, Delayed regulatory rule updates, Over-reliance on automation eroding staff knowledge, Data access or security issues, Project timeline slippage
• Have you experienced previous automation projects that failed or fell short? What happened and what would you change next time?
• What internal constraints would most likely block progress (budget cycles, procurement policy, resource availability, political buy-in)? Options: Budget cycle timing, Procurement/contracting rules, Limited IT resources, Competing priorities, Leadership skepticism
• If we surfaced a critical mapping error during validation, what remediation governance would you expect us to follow? Options: Joint change control board, Vendor-led correction with approval, Documented exception process, Escalate to leadership

Proof That This Works: What Would Convince You?

• What evidence would remove the biggest barriers to adoption—what would make leadership say 'yes' today?
• Which validation artifacts would you require from a pilot or proof-of-concept (select all that apply)? Options: Side-by-side comparison with prior filings, Automated reconciliation reports, Complete audit trail of mappings, Regulator-format test filing, Third-party attestation
• Would running a simulated 'near-miss' using your historical data to reproduce the failure and prove prevention be persuasive? Options: Yes, essential, Helpful but not required, Not necessary, Unsure
• What SLA commitments would you need around mapping error resolution and regulatory rule updates? Options: 24–72 hour response, Weekly patch cadence, Monthly roadmap updates, Custom SLA
• Are there internal or external auditors/regulators we should include early to accelerate acceptance of automated filings? Options: Yes—internal audit, Yes—external auditors, Yes—regulatory liaison, No, not necessary, Unsure

Decision, Timing, and Next Steps — Where Do We Go From Here?

• What is the single most important decision criterion for moving forward (e.g., cost, time-to-value, auditability, governance)? Options: Cost, Time-to-value, Audit trail and compliance, Integration ease, Vendor reputation
• Who sits on the decision committee and what is the approval path for projects of this type?
• What is your realistic budget window and procurement timeline for a remediation or automation project like this? Options: Immediate (allocated), This quarter, Next quarter, Next fiscal year, Undecided
• Which items must be confirmed before we can start a pilot (select all that apply)? Options: Source system access, Sample datasets provided, Mapping owners appointed, Test environment available, Executive sponsor confirmation
• How comfortable would you be running a parallel filing run vs. production cutover as part of acceptance testing? Options: Very comfortable, Comfortable with controls, Prefer limited parallel testing, Not comfortable
• If we proposed a 30–90 day pilot that simulates your recent near-miss and delivers reconciliation artifacts, would you be willing to commit the required people and access? Options: Yes—ready now, Yes—within 30 days, Maybe—need internal approval, No

Start With the Last Near‑Miss (Tell Us, in Plain Terms)

• Briefly describe the last late filing or resubmission event and its immediate outcome.
• Which filing(s) were involved? Options: Quarterly statutory statement (NAIC), Annual statutory statement, SEC/10-Q or 10-K, Call Report / FFIEC, HMDA/CRA, Other
• When was the issue discovered relative to the submission deadline? Options: >2 weeks before, 1–2 weeks before, 3–7 days before, 24–72 hours before, <24 hours before, After submission
• Who first detected the problem? Options: Analyst/individual contributor, Team lead/manager, Controller, Compliance officer, Regulator / external party, Automated monitoring, Other
• What immediate remediation steps were taken (brief timeline and owners)?

Is One Person the Process? (Who Would Carry the Torch if They Left?)

• If the analyst who mapped the last filing were unavailable tomorrow, how confident are you that the next submission would be correct? Options: Very confident, Somewhat confident, Not confident, We would likely miss the deadline
• List the people or roles that touch mapping, reconciliation, and final sign‑off today (names or titles).
• Which of those roles have formal runbooks, documented procedures, or recorded training? Options: All have detailed documentation, Most have basic docs, Some have notes only, None are documented
• Are backups or delegates assigned for each critical task? If yes, how well can they perform under time pressure? Options: Backups assigned and trained, Backups assigned but not trained, No formal backups, We use external consultants as backup
• How long would it take an informed but new engineer/analyst to run a full filing end‑to‑end from source extracts to submission? Options: <1 day, 1–3 days, A week, >1 week, Unknown

Trace the Data — Where Does It Bend or Break?

• Which link in the data chain do you suspect causes most discrepancies: source systems, ETL/mappings, manual spreadsheets, or filing templates? Options: Policy administration system, General ledger / GL, Investment accounting, Claims warehouse, ETL / transformation scripts, Manual spreadsheets, Regulatory filing templates
• Please list the primary source systems and their owners (system name + owner/team).
• How are mappings currently created and stored? Options: Manual Excel mapping files, ETL tool (e.g., Informatica, Talend), Custom scripts (Python/R/SQL), Vendor mapping tool, Embedded in legacy system, Other
• How often are source extracts produced and reconciled to the GL or policy system? Options: Daily, Weekly, Monthly, Per filing cycle only, Ad hoc
• Who is the owner of mapping rules and transformation logic (title/team)?
• Can you provide a sample extract (masked) from each key system for mapping validation? Options: Yes—all samples ready, Partial—some available, No—requires work to extract, Unsure

When Numbers Don't Line Up, Who Raises the Flag?

• Who in your organization has both the authority and the incentive to escalate unresolved cross‑schedule differences? Options: Controller, Chief Compliance Officer, Head of Reporting, Finance manager, No clear escalation owner, Other
• How frequently do reconciliations surface unexplained variances that remain open at submission? Options: Never, Rarely, Occasionally, Often, Almost always
• What reconciliation tools or processes do you use (select all that apply)? Options: Excel reconciliation sheets, Dedicated reconciliation software, Manual tie-outs, In‑house dashboards, No formal reconciliation tool
• What tolerance thresholds trigger an investigation (e.g., $ amount, percentage, or qualitative)?
• Provide an example of a recent unresolved difference: size, schedules affected, and how it was handled.
• How long does it typically take to resolve a significant reconciliation exception? Options: Same day, 1–3 days, A week, Multiple weeks, Still open/varies

Paper Trails, Audit Trails — Where Are They Missing?

• Where in the workflow do you most often lack regulator‑grade evidence (e.g., change history, sign‑offs, version control)? Options: Mapping change history, Data extract provenance, Reconciliation records, Final submission bundle, Exception handling documentation, All of the above
• Do mappings and transformation rules have version control and an auditable change log? Options: Yes—full versioning, Partial/versioning for some artifacts, No version control, Unsure
• How are sign‑offs captured (electronic approval, email, shared drive stamp)? Options: Electronic workflow (eSign), Approval emails, Manual paper sign‑off, Shared document notes, No formal sign‑off
• Where are reconciliation worksheets and submission artifacts stored and for how long? Options: Secure compliance repository, Shared network drive, Local machines, Document management system (e.g., SharePoint), Other
• How comfortable are you sharing current artifacts with a vendor during remediation (data masking/privacy concerns)? Options: Fully comfortable, Comfortable with masking, Reluctant—legal review needed, Not comfortable

Access, Sandboxes, and Test Data — Do You Have What Matters?

• Could a third‑party run a meaningful end‑to‑end filing test in a sandbox today using masked data? Options: Yes—full sandbox available, Partial sandbox/test environment, No sandbox available, Unsure
• Which of these test artifacts are available and current? Options: Masked policy extracts, GL journals and trial balance, Investment ledger extracts, Claims data / loss triangles, Prior filing files (submitted), Reconciliation workpapers
• Are there access or legal constraints that usually delay providing extracts to vendors? Options: Strict legal review required, IT/ops provisioning delay, Data privacy concerns, No significant constraints
• How recent are your sample datasets relative to the current filing period? Options: Current month, Previous quarter, Previous filing period, Older than 6 months, Varies by system
• Who approves provisioning of test access and who executes it (title/team)?

If We Could Snap Our Fingers, What Changes Would Feel Like a Win?

• What would you notice first if your reporting process stopped producing late filings and material reconciliations? Options: Fewer late notices/regulatory letters, Shorter close-to-file timelines, Less nightly/after-hours work, Better executive confidence, Fewer audit findings
• Which success signals matter most to your sponsor (CFO) vs. your operational teams (controllers/compliance)? Options: Zero late filings, Automated cross-schedule reconciliation, Faster close-to-file, Clear audit trail, Lower headcount for routine tasks, Other
• What residual risk level would you accept after automation (e.g., % variance tolerated or number of exceptions per cycle)?
• What SLAs would be required for mapping fixes and rule updates to feel safe (time to fix, time to deploy)? Options: <24 hours, 48–72 hours, Up to 1 week, Depends on severity
• How often would you want governance reviews once a solution is live (weekly, biweekly, monthly, quarterly)? Options: Weekly, Biweekly, Monthly, Quarterly, Ad hoc

What Would It Take to Move Forward — Risk, Budget, and People?

• If we proposed a short pilot to eliminate the next filing near‑miss, what is the single biggest barrier to saying yes within 30 days? Options: Budget, Legal/Procurement, Lack of resources/time, Data access, Risk appetite, Other
• Who are the decision‑makers required to greenlight a pilot and final procurement (title/team)?
• What level of budget authority is needed to start a pilot without full CFO sign‑off? Options: Operational budget owned by Controller, Department head approval, Requires CFO approval, Requires exec committee
• What internal resources would you commit to a 6–8 week pilot (mapping owner, IT support, reconciler, compliance reviewer)? Options: Dedicated full‑time resources, Part‑time commitments, Ad hoc support only, External consultants required
• What legal or procurement guardrails must we be aware of before exchanging sample data or running tests? Options: Standard NDA only, Security review required, Data privacy assessment, Vendor risk assessment, Contracting lead time

Collect a Snapshot — The Logistics We Need to Start

• If we had 48 hours to compile a snapshot of your current state, what would be the single hardest item to produce? Options: Masked source extracts, Mapping documentation, Reconciliation worksheets, Access to test environment, Regulator correspondence, Other
• Please mark which artifacts you can provide within the first week. Options: Masked policy administration extract, GL trial balance and journals, Investment ledger extract, Claims/loss triangle sample, Last two filed regulatory submissions, Reconciliation workpapers, Mapping spreadsheets
• Who should we contact to request each of those artifacts (name, title, email)?
• Are there scheduled blackout windows or maintenance periods that would block extracts or testing in the next 30 days? Options: Yes—provide dates, No scheduled windows, Unsure
• What format do your current extracts come in (CSV, Excel, database dump, API, other)? Options: CSV/flat files, Excel workbooks, Database export (SQL dump), API access, Proprietary format
• Any other red flags or constraints we should log now to avoid surprises during discovery?

Start: Tell Me About the Filing That Kept You Up Last Night

• Briefly describe the incident that led to the late or corrected filing (what happened, which filing, and when).
• Who first raised the issue and how was the problem discovered? Options: Internal analyst, Controller review, Regulator inquiry, External auditor, Other
• What immediate consequences followed the resubmission (e.g., regulator letter, reputational impact, internal investigation)? Options: Regulator letter/inquiry, Escalation to executive team, Restatement, No external consequence yet, Other
• How would you describe how that moment felt for your team and leadership?
• On a scale, how confident are you today that the same failure could be prevented next quarter? Options: Very confident, Somewhat confident, Unsure, Not confident

Who’s Holding the Keys?

• Imagine your primary reporting analyst suddenly couldn’t perform their duties—what breaks first?
• List the people or roles who currently sign off on statutory and SEC filings.
• Which single role or team would you say is the single point of failure for filing accuracy? Options: Reporting analyst, Controller office, IT/systems team, External consultant, Other
• Who in your organization has final budget authority to approve investments in reporting automation? Options: CFO, Chief Compliance Officer, Controller, CIO, Board/Finance Committee, Other
• How often do you have cross-functional governance meetings that include compliance, finance, and IT to discuss reporting risk? Options: Weekly, Bi-weekly, Monthly, Quarterly, Rarely/Never

Where the Data Lives and How Fragile It Is

• If your source systems stopped sharing data reliably, could you still produce an accurate filing on time? Options: Yes, with existing manual workarounds, Maybe, with extra overtime, No, would miss deadline
• Which source systems feed your regulatory filings? Select all that apply and add others in the next question. Options: Policy administration, General ledger / GL, Investment accounting, Claims warehouse, Broker-dealer trade systems, Cash management, Other
• Describe any recent system changes, migrations, or conversions that impacted reporting (include timing and teams involved).
• Which datasets can you produce as samples for testing today (choose all available)? Options: Full GL extract, Policy-level detail, Claims loss triangle, Investment positions, Trial balance, None available currently
• How well documented is your data lineage and field-level ownership for the fields that feed filings? Options: Comprehensively documented, Partially documented, Ad hoc notes only, Not documented

When Processes Break, How Fast Do You Know?

• How often do mapping or reconciliation errors surface after you’ve already submitted a filing? Options: Regularly (every filing cycle), Occasionally, Rarely, Never
• How long does it typically take from detection to root-cause identification for a material reporting error? Options: Less than 1 day, 1–3 days, 4–10 days, More than 10 days
• What monitoring or validation checks do you have in place today (automated reconciliation, manual tie-outs, peer review, none)? Options: Automated reconciliations, Manual spreadsheet tie-outs, Peer review process, Audit sampling, No formal checks
• When an exception is raised during preparation, who owns remediation and how is it tracked? Options: Analyst, Controller/Finance, IT/Data team, Compliance, Tracked in ticketing system, Tracked ad hoc
• Tell us about a near-miss you had (what failed, how it was caught, and what changed after).

What Success Actually Looks Like

• If a future filing passed regulator scrutiny with zero follow-up, what would have changed in your process?
• Which measurable success signals matter most to you? Pick up to three. Options: No late filings, Zero material restatements, Automated reconciliations, Reduced manual hours per filing, Full audit trail, Faster time-to-file
• What level of residual risk is acceptable for automated mappings and transformations? Options: Near-zero (very conservative), Low (minor exceptions tolerable), Moderate with human review, High tolerance
• How would you measure ROI or success after a deployment (time saved, error reduction, audit findings, cost avoidance)? Options: Time saved, Error reduction, Fewer regulator actions, Lower audit findings, Operational cost savings, Other
• Who needs to see the success dashboards and how often would they review them? Options: CFO, Controller, Chief Compliance Officer, CIO/IT, Board/Committee

What Would Stop You From Making That Change?

• Why might leadership quietly choose to accept the current risk rather than invest in automation?
• Which of these barriers are most relevant to you today? Select all that apply. Options: Budget constraints, Procurement timelines, Integration complexity, Loss of internal subject-matter expertise, Audit/controls concerns, Change management resistance
• Have prior attempts to change reporting tooling failed or stalled? Tell us what happened and why.
• What internal compliance or audit requirements would we need to satisfy before you could run automated filings?
• How concerned are you about mid-cycle regulatory rule changes and the platform’s ability to adapt quickly? Options: Very concerned, Somewhat concerned, Not concerned

How We’d Prove It Works — The Acceptance Tests

• What concrete tests would convince you automation is safe to push to production for regulator submission?
• Which of these acceptance criteria are mandatory for signoff? Select all that apply. Options: Reconciles to prior filing totals, Passes cross-schedule consistency checks, Full audit trail for all transforms, Rollback and repeatable test runs, Sign-off by Controller and Compliance
• Who must approve the acceptance results before we run parallel or live filings? Options: Controller, Chief Compliance Officer, CFO, CIO, Internal Audit
• What sample size and date ranges would you expect in validation runs to feel confident (e.g., full-quarter, rolling 2 quarters)? Options: Full most-recent quarter, Rolling 2 quarters, Rolling 4 quarters, Custom selection
• Describe the rollback or remediation plan you’d require if an automated run produced unexpected variances.

Decision and Budget: Who Says Yes and When?

• What would make the CFO release budget now rather than later—what is the tipping point?
• Which stakeholders must be engaged in the procurement decision? Select all that apply. Options: CFO, Controller, Chief Compliance Officer, CIO/IT, Procurement, Legal
• What is your expected procurement timeline from evaluation to contract signature? Options: Less than 1 month, 1–3 months, 3–6 months, 6+ months
• Estimate the budget range you’d consider for a solution that materially reduces filing risk. Options: <$100k, $100k–$500k, $500k–$1M, >$1M, Unsure
• Do you have preferred contracting or security requirements (e.g., SOC2, data residency) we should know about? Options: SOC2, ISO 27001, On-prem option, Data residency constraints, Standard vendor terms, Other

Timeline, Risk, and Critical Dates

• If our goal is to eliminate late filings next quarter, what is the absolute latest start date for work to begin?
• List your upcoming filing and blackout dates that we must avoid for heavy integration work.
• How much lead time do you need for testing before a live submission (select one)? Options: 1–2 weeks, 2–4 weeks, 1–3 months, 3+ months
• Are there any seasonal or cyclical activities (e.g., year-end close, audits) that would prevent deployment during parts of the year? Options: Yes, No, Not sure
• What is your tolerance for parallel runs (running both manual and automated processes) before full cutover? Options: Required for at least 2 cycles, One cycle is enough, Not required, Depends on results

People, Training, and Organizational Change

• What roles will need training to operate and govern the automated process (choose all that apply)? Options: Reporting analysts, Controller team, Compliance, IT/data engineers, Legal, External auditors
• How do you prefer training delivered—hands-on workshops, recorded modules, playbooks, or train-the-trainer? Options: Hands-on workshops, Recorded modules, Detailed playbooks, Train-the-trainer, Combination
• What internal documentation or runbooks exist today for exception workflows and acceptance testing? Options: Comprehensive, Partial, Minimal, None
• How much of the current team’s time should be preserved for knowledge transfer during implementation? Options: >50% of time, 25–50% of time, <25% of time, Ad hoc as needed
• What would make your team feel confident that automation won’t erode institutional knowledge?

Next Steps and Comfort Items

• What would make you sleep better the night before our first integration—what assurances do you need?
• Would you be willing to run a small pilot or proof-of-value using recent filing data? Options: Yes, immediately, Yes, after scoping, Maybe, No
• What evidence or deliverables would you expect from a pilot to recommend moving to production? Options: Reconciliation report vs prior filing, Audit trail of transformations, User acceptance signoff, Performance benchmarks, Other
• Who should be our primary contact for scheduling technical discovery and providing sample datasets?
• When would you like us to follow up with a proposed scope and timeline? Options: This week, Next week, In two weeks, Next month, Unsure

Start Here: The One Filing That Changed Everything

• Briefly describe the late filing and resubmission that prompted this project—who noticed it and when?
• How long did it take from discovery to remediation (root cause identified and filing resubmitted)? Options: Within 24 hours, 1–3 days, 4–10 days, More than 10 days
• Which regulator(s) followed up with a letter or inquiry after the resubmission? Options: State Insurance Department, NAIC, SEC, FDIC, Federal Reserve, Other
• Which internal teams were most involved in the remediation effort? Options: Chief Compliance Office, Controller/Accounting, IT/CIO, Actuarial, Risk/Legal, Operations, External consultants
• When you think back to executive reactions (CFO, CCO, Board), what was the dominant tone or fear that came up?

How Close Are You to a Formal Examination?

• If the regulator dug deeper tomorrow, what would they most likely find about your filing controls and repeatability?
• How many near-miss filing events (late filings, resubmissions, material corrections) have you experienced in the last 24 months? Options: None, 1, 2–3, 4–6, 7+
• Which failure types most commonly cause your near-misses? Options: Data mapping errors, Reconciliation timing gaps, Missing or late source data, Manual spreadsheet mistakes, Approval routing failures, Other
• Who today acts as the single-point-of-failure for filing assembly or final edits (role/title)?
• Before submission, how often do you run acceptance checks that compare to prior filings for consistency? Options: Every filing, Most filings, Occasionally, Rarely, Never

Where the Data Actually Lives — and Where It Breaks

• Do your source systems act like aligned truths or a set of competing single-source narratives?
• Which source systems feed your regulatory filings (select all that apply)? Options: Policy administration, General ledger / ERP, Investment accounting, Claims warehouse, Reinsurance systems, Data warehouse / BI, Other
• What vendors or versions are in scope for those systems (examples: Guidewire, SAP, BlackRock Aladdin)?
• Who owns each source system and who currently owns the mappings to the filing templates (list names or roles)?
• How frequently do extracts and reconciliations run ahead of filing windows? Options: Real-time / continuous, Daily, Weekly, Monthly, Ad-hoc

Who Holds the Keys — Accountability, Authority, and Politics

• When accuracy and timing conflict, who would win the argument internally—who signs the filing despite concerns?
• Who has final budget authority for remediation or automation projects like this? Options: CFO, CEO, Board/Committee, Controller, Other
• What level of regulatory tolerance would trigger formal escalation for you (examples: any late filing, a material misstatement, repeated errors)? Options: Any late filing, Material misstatement, >$ specified $ exposure, Pattern of issues, Unsure
• How are disputes between Compliance and Operations resolved during filing preparation and sign-off?
• Which function should be the executive sponsor for an automation effort—Compliance, Controller, CIO, or another party? Options: Chief Compliance Officer, Controller, CIO / IT, CFO, Other

What Winning Looks Like — Regulator-Defensible Outcomes

• If you could present one undeniable proof to a regulator that your process is reliable, what would that single proof be?
• Which success signals are highest priority for you (pick up to three)? Options: No late filings, Automated cross-schedule reconciliations, Complete audit trail / lineage, Regulator-facing evidence pack, Faster close-to-file cadence, Lower manual effort, Reduced error rate
• What residual risk threshold is acceptable for automated mappings and reconciliations (your tolerance for exceptions left to manual review)? Options: 0% (zero tolerance), <0.1%, <1%, <5%, Unsure / depends
• What acceptance tests or reconciliation checks do you consider non-negotiable before allowing production filings?
• Which roles must sign the go-live acceptance certificate for filings (select all that apply)? Options: Controller, Chief Compliance Officer, CFO, IT Lead / CIO, Legal, External Auditor, Other

What’s Really Stopping Automation — Tech, People, or Politics?

• When you look at past attempts to fix this, what single reason best explains why they stalled?
• Which of these barriers worry you most about adopting a vendor automation platform? Options: Mapping errors or incorrect transformations, Lack of IT resources for integration, Budget constraints, Change management / staff resistance, Speed of regulatory rule updates, Loss of institutional knowledge, Data security or privacy
• Have you run a pilot or POC for reporting automation before, and if so, what specifically prevented it from scaling?
• How do you currently manage mapping updates when chart of accounts or source feeds change?
• What vendor support model would give you confidence—fully managed, co-managed, tooling + ticketing, or self-service? Options: Managed service, Co-managed, Tooling + support tickets, Self-service

Data, Samples, and Validation — Can We Run The Tests You Trust?

• If asked for the minimum dataset that proves end-to-end mapping and reconciliation, could you provide it today?
• Do you have anonymized sample datasets and prior filings available for validation runs? Options: Yes — ready today, Partially ready, No — will require effort, Unavailable due to policy
• What formats are your prior filings and data extracts in (pick all that apply)? Options: NAIC templates, XBRL / SEC formats, CSV / Excel, Database exports (SQL), Proprietary extracts, Other
• Who controls access to test data and who must approve anonymization or sharing with a vendor?
• How quickly could you assemble the minimum POC dataset if we agreed scope today? Options: <1 week, 1–2 weeks, 3–4 weeks, >4 weeks, Unsure

Proof, Controls, and Audit Trails — What Regulators Will Want to See

• Would your auditors and regulator accept automated reconciliations and mapping lineage without human-run exception logs?
• Which audit artifacts are mandatory for you after a filing (select all that apply)? Options: Reconciliation reports, Mapping lineage and transformation logs, Change logs / version history, Exception runbooks and remediation steps, User access and approval logs, Signed acceptance tests
• What retention period do you require for filing evidence and audit trails? Options: 1 year, 3 years, 5 years, 7+ years, Unsure
• How mature is your current governance cadence for filings (defined owners, frequency, escalation paths)? Options: Well-established, Defined but informal, Ad-hoc, Not defined
• Who in your organization would own ongoing SLA monitoring for mapping errors and rule updates?

Decision Moment — Timing, Budget, and Next Steps

• If avoiding regulator escalation is the objective, what is the earliest acceptable go-live window you would consider?
• What procurement path do you prefer for a first-phase engagement? Options: Pilot then enterprise roll-out, Direct enterprise contract, RFP / competitive process, Other
• What budget range do you expect for an initial phase that includes mapping, validation, and a production pilot? Options: <$50k, $50k–$150k, $150k–$500k, $500k–$1M, >$1M, Unsure
• What is your realistic timeline to final budget approval for this type of remediation project? Options: Immediate (<30 days), 30–60 days, 60–90 days, >90 days, Unsure
• Who are the additional stakeholders or approval authorities we should include in scoping conversations?

Ready to Change — Or Hope It Won’t Happen Again?

• Are you prepared to adopt a different process now, or do you expect to deploy only tactical fixes and hope the problem doesn’t recur? Options: Prepared to adopt a new process, Prefer tactical fixes only, Undecided / need more info
• How comfortable would you be proactively sharing our validation evidence with the regulator to demonstrate remediation? Options: Very comfortable, Somewhat comfortable, Prefer not to, Unsure
• What are the top three concerns we must address to earn your team’s confidence in a vendor solution?
• Would you like us to prepare a targeted POC plan that includes required samples, acceptance tests, and a proposed timeline? Options: Yes — please prepare, Maybe later, Not at this time
• What would be the best next step and who should we invite to the kickoff conversation from your side?