Opening: Tell Us About Your Claims World

• Who in your organization will be the primary point-of-contact for claims program conversations (title and functional responsibilities)?
• Which specialty lines generate the most complex or high-severity claims for you today? Options: Professional liability / E&O, Directors & Officers, Environmental, Construction defect, Product liability, Excess casualty, Self-insured retention (large commercial), Other
• Approximately how many active complex/high-severity files do you have right now (open to an approximate range)? Options: 0–25, 26–100, 101–500, 501–1,000, 1,000+
• How would you describe the typical lifecycle length for these complex files (from notice to resolution or long-term litigation posture)? Options: Under 1 year, 1–3 years, 3–7 years, 7+ years, Highly variable / case-by-case
• What three words would you use to describe how handling these files currently feels to your claims leadership and litigators?
• Which systems or tools are used today for case management, reserves and reporting (name the platform(s) and any internal data sources)?

If a Precedent-setting Claim Landed Tomorrow, Would Everyone Agree?

• If a high-value, precedent-setting claim arrived this morning, is there a single, clearly empowered decision-maker for coverage and settlement strategy? Options: Yes — clear single owner, Mostly — small group with defined escalation, No — responsibility is diffuse, Unsure
• Which stakeholders must sign off on major coverage positions or settlements (select all that apply)? Options: VP/Chief Claims Officer, Line-of-business leader, Underwriting head, General counsel / in-house legal, Actuarial / reserving, Broker, Other
• How often have disagreements between claims, underwriting, and legal delayed a major decision in the last 12 months? Options: Never, 1–2 times, 3–5 times, More than 5 times
• Tell us about a recent situation where misalignment on a claim’s strategy had measurable impact (time, cost, regulatory exposure) — what happened and how did it feel for leadership?
• What would ‘good’ look like to each stakeholder (claims, underwriting, legal, business) after 6 months of partnering with an external specialty claims administrator?
• Are there decision thresholds (dollar amounts, litigation phases, coverage ambiguity) that automatically trigger executive review? If so, what are they?

When Things Break, Where Do They Break First?

• What root causes most commonly lead to claims going off-track in your book (pick up to three)? Options: Insufficient subject-matter expertise, Delayed coverage analysis, Poor counsel management, Reserve volatility / data gaps, System or workflow failures, Surge overload, Other
• Which part of your current workflow creates the most friction for complex claims — intake, investigation, coverage analysis, counsel selection, litigation oversight, or reporting? Options: Intake/triage, Investigation/assignment, Coverage analysis, Defense counsel selection, Litigation management/oversight, Reserving & reporting, Other
• How often do operational issues (e.g., missing files, late data, vendor delays) lead to reserve adjustments or surprise spend? Options: Almost always, Often, Occasionally, Rarely, Never
• What specific failures have you seen in vendor or TPA handoffs that you would not tolerate going forward?
• Describe a recent surge event (cat, mass-tort, regulator-driven litigation) and how well your team absorbed the volume — what broke and what held?
• From a cost perspective, where do you see the biggest leakage today (defense spend, expert fees, settlement creep, prolonged litigation, poor subrogation)? Options: Defense counsel spend, Expert witness costs, Settlement creep, Prolonged litigation expense, Subrogation failures, Other

How Will You Measure Whether This Partnership Actually Works?

• Which outcome matters most to your executive team right now: reserve accuracy, litigation spend reduction, faster closures, coverage defensibility, or improved regulatory posture? Options: Reserve accuracy, Reduce litigation spend, Faster claim resolution, Coverage defensibility, Regulatory/compliance improvement, Other
• What specific KPIs are you already tracking for complex claims (select all that apply)? Options: Case cycle time, Average indemnity per file, Litigation spend per file, Reserve variance vs actuals, Frequency of coverage disputes, Defense counsel performance scores, Reporting timeliness/accuracy
• What are acceptable target ranges for two priority metrics you’d expect a partner to achieve in 12 months (name metric and target)?
• How do you currently validate reserve methodology and actuarial inputs for complex claims — is it internal, third-party, ad-hoc, or automated? Options: Internal claims + actuarial, Independent actuarial review, Third-party consultant, Ad-hoc case reviews, Not formally validated
• Tell us about any regulatory, investor, or board-level reporting needs that a partner must support — timing, auditability, or format requirements?
• How would you prioritize these success signals if you had to rank them: speed to decision, reduced spend, better legal outcomes, stronger reserve predictability? Options: 1st, 2nd, 3rd, 4th

Imagine a Partner Who Handles Your Toughest Files — Walk Us Through One

• Pick a recent claim that felt especially challenging and describe the facts, coverage issues, and why it became a strain on your team.
• If we were to walk that claim through together, which decision points would you want us to demonstrate (coverage opinion, reservation strategy, counsel selection, settlement authority, litigation plan)? Options: Coverage opinion, Reservation of rights / denial, Defense counsel selection, Litigation budget & milestones, Settlement authority and limits, Subrogation strategy
• How important is it that our adjuster team includes legally trained professionals versus pure claims handlers? Options: Essential — legal expertise required, Very important, Nice to have, Not necessary
• Describe the level of hands-on scenario testing you'd like to run before committing (mock file review, joint governance call, parallel handling of a live file). Options: Mock file review, Joint governance pilot, Parallel handling of select live files, Short claims pilot (30–90 days), Other
• What would reassure you most during a scenario walkthrough — transparent fee forecasts, clear escalation rules, or demonstrable win/loss examples? Options: Transparent fee forecasts, Clear escalation rules, Demonstrable win/loss examples, References on similar matters, Other
• Would you be open to role-playing a coverage call with our coverage counsel in a discovery session? If yes, who should attend? Options: Yes — claims & legal, Yes — claims only, Maybe — depends on agenda, No

Boundaries, People, and Promises — What Must Be Clear?

• Which contractual or operational non-negotiables must be defined up front (SLA response times, settlement authority, data ownership, cybersecurity, regulatory controls)? Options: SLA response times, Settlement authority levels, Data ownership & access, Cybersecurity & SOC requirements, Regulatory/compliance clauses, Staffing continuity guarantees, Other
• How do you prefer adjuster assignments to be structured: dedicated lead per file, pooled specialty desk, or hybrid? Options: Dedicated lead per file, Pooled specialty desk, Hybrid (dedicated for high-severity)
• What SLA targets feel realistic for initial contact, coverage memorandum, and monthly reporting from an external partner?
• Are there regulatory, privacy, or data residency constraints we must meet (e.g., state-specific rules, EU/UK data laws, NAIC expectations)? Please list.
• What governance cadence would you require (weekly operational, monthly steering, quarterly executive reviews) and who must attend each? Options: Weekly operational, Bi-weekly, Monthly steering, Quarterly executive reviews, Ad-hoc as issues arise
• Which reporting formats and frequency are essential at launch (real-time portal, weekly dashboard, actuarial reserve file, audit package)? Options: Real-time portal access, Weekly dashboard, Monthly actuarial pack, Ad-hoc audit package, Quarterly business review

If We Asked For a Sample Transfer Tomorrow, How Ready Are You?

• Do you currently have clean, machine-readable sample claim files and a data dictionary available for a pilot transfer? Options: Yes — ready now, Yes — needs minor cleanup, No — would require significant prep, Unsure
• Which data feeds and integrations are required for onboarding (list claim system, billing, defence counsel ledger, document repository, subrogation ledger)?
• What security or vendor assessment steps must be completed before data exchange (SOC2, cyber questionnaire, legal approval)? Options: SOC2 report, Vendor security questionnaire, Legal vendor approval, Background checks on personnel, Other
• Who owns the technical onboarding timeline on your side and what is their contact role (title)?
• How long does it typically take to grant portal access and SSO integration for a new vendor in your environment? Options: <2 weeks, 2–4 weeks, 1–2 months, Longer than 2 months, Varies widely
• If there are gaps, what would be the minimally acceptable readiness items to start a small pilot (e.g., 10 files, limited scope)?

What Would Success Look Like After Deployment — And What Could Stop It?

• In the first 90 days after cutover, which three acceptance criteria would cause you to sign off on the engagement?
• Which validation checks do you require before full cutover (sample handling, reserve methodology reconciliation, reporting parity, escalation drills)? Options: Sample handling test, Reserve methodology reconciliation, Reporting parity check, Escalation path drill, Counsel invoice validation, Other
• Who on your team will own post-launch validation and how will success be measured internally?
• What change-management risks concern you most (internal stakeholder buy-in, counsel resistance, data mistrust, vendor reliability)? Options: Internal buy-in, Counsel resistance, Data quality/trust, Vendor staffing continuity, Regulatory scrutiny, Other
• If things aren’t meeting expectations at 120 days, what remedies or governance interventions would you expect from a partner?
• Finally, how soon would you be prepared to begin a structured pilot if a recommended scope, team, and pilot price were presented? Options: Immediately, In 2–4 weeks, In 1–3 months, In 3–6 months, Unsure

What Does a Typical Claims Day Feel Like for You?

• On an average week, how many new complex claims (high-severity, multi-party, or litigious) does your claims organization receive? Options: 0–5, 6–20, 21–50, 51–100, 100+
• Which specialty lines make up most of that volume? Options: Professional liability / E&O, D&O / Management liability, Environmental, Construction defect, Product liability, Excess casualty, Other
• What does the typical handoff look like from intake to assignment—who touches the file first and what are the first three actions taken?
• What claims management system(s) do you use today? Options: Guidewire ClaimCenter, Duck Creek, Xactimate/XactAnalysis, Insurity, Custom/Proprietary, Spreadsheet / Email-driven, Other
• What’s a realistic caseload for a subject-matter adjuster handling these files at your organization? Options: <10 active high-complexity files, 10–25, 26–50, 51–75, 75+
• Who on your team currently owns complex-claim governance (e.g., coverage calls, litigation strategy, reserve sign-off)? Please name roles/titles.

What Are the Numbers Actually Telling You (and What Are They Not)?

• When your KPIs look healthy but outcomes don’t, what usually explains the gap?
• Which of these KPIs are tracked and trusted today? Options: Reserve accuracy / error rate, Case and incurred development, Litigation spend per claim, Avg. days to first coverage decision, SLA compliance, Subrogation recovery rate, Customer satisfaction / claimant experience, Other
• How confident are you in the accuracy of reserves and loss development used by actuarial teams? Options: Very confident, Somewhat confident, Not confident, Unknown / haven’t checked
• Tell us about a recent time your reporting changed a reserve or strategy—what happened and what did you learn?
• How frequently do you produce actuarial-quality reports and who reviews them? Options: Daily, Weekly, Monthly, Quarterly, Ad-hoc
• Which reporting formats would make your teams more decisive (select all that apply)? Options: Claim-level drilldowns, Portfolio heat maps, Litigation spend dashboards, Reserve development triangles, Custom alerts for thresholds, API / raw data extracts

Which Claim Patterns Keep You Up at Night?

• When a claim turns into a multi-year litigation or large judgment, what are the most common early warning signs you missed?
• Which of these failure modes have you seen in the last 24 months? Options: Late coverage analysis / missed defenses, Under-reserving for complexity, Poor defense counsel control / runaway fees, Slow investigation leading to lost recovery, Regulatory or bad-faith exposure, Data/reporting latency, Other
• How often do you identify root cause as process, people, data, or governance (pick the strongest driver)? Options: Process, People / skill gaps, Data / systems, Governance / escalation, Combination / unclear
• Give one specific example of a claim failure mode that repeated across multiple files—what was the pattern, and how long did it persist?
• How does the recurrence of these failures impact underwriting confidence and renewal conversations?
• If you could eliminate one recurring failure within the next quarter, which would it be and why?

If You Could Fix One Cost Driver Tomorrow, What Would It Be?

• What are the top three drivers of claims cost in your book of business right now? Options: Defense counsel spend, Reserve mis-estimation, Large indemnity payouts, Litigation frequency, Subrogation underperformance, Fraud / exaggerated claims, Other
• How much of your annual claims spend is concentrated in the top 10% of files (estimate)? Options: <20%, 20–40%, 41–60%, 61–80%, 80%+
• Have you tried remediation efforts (e.g., preferred counsel panels, centralized coverage reviews)? Which worked and which didn’t?
• What level of delegated authority or SLA rigor would you be willing to test in a pilot to reduce those costs? Options: Tight SLAs + centralized approvals, Delegated with periodic audits, Full TPA-managed with governance, Unsure / need guidance
• If we could design a 90-day pilot to reduce one cost driver, what measurable outcome would make it a success?

How Honest Is Your Data About the Work You Do?

• If I asked for a clean, business-ready extract of recent complex-claim data, how quickly could you provide it? Options: Same day, Within a week, 2–4 weeks, Longer than a month, We don’t have one
• Which of these data elements are consistently captured and reliable for complex claims? Options: Coverage trigger dates, Reserve history, Defense counsel invoices, Litigation milestones, Claimant medical/legal records, Payment history, None of the above
• How often do you reconcile claims system data with actuarial or finance reports and who signs off on discrepancies? Options: Monthly, Quarterly, Annually, Ad-hoc, Never reconciled
• What formats and integrations would make your teams actually use a partner portal (select all that apply)? Options: Real-time API, Daily CSV push, Secure SFTP, Native integration with our CMS, Custom dashboard views, Email-triggered alerts
• On a scale of 1–5, how would you rate the overall trustworthiness of your claims data for executive decision-making? Options: 1 - Not trustworthy, 2, 3 - Mixed, 4, 5 - Highly trustworthy

Who Actually Decides When a Claim Escalates or Settles?

• When a complex claim reaches a material decision point, who must be consulted or sign off (roles/titles)?
• How often do coverage interpretations escalate to legal or underwriting for concurrence? Options: Almost always, Often, Sometimes, Rarely, Never
• Describe your current escalation path for high-exposure claims—what works and what creates friction?
• How do underwriters and claims coordinate on precedent-setting coverage positions and reserves? Options: Regular governance forum, Ad-hoc meetings, Email approvals, No formal process, Other
• What would make governance feel faster and more reliable to you (pick top two)? Options: Clear authority matrix, Pre-approved settlement bands, Faster data/reporting, Dedicated point people, Escalation SLAs

Show Us a File That Tells Your Story

• Can you describe one recent complex claim that best represents your biggest pain point—what happened, when, and what the final status was?
• Which artifacts from that file could you share to help us understand the workflow (e.g., chronology, reserve run, counsel invoices, coverage memos)? Options: Chronology / timeline, Reserve development history, Coverage analysis memos, Defense counsel invoices, Court docket / pleadings, Nothing available
• What decision points in that file would you say were handled well, and which were mishandled?
• If we were standing in your office the day that file landed, what three immediate actions would you want a partner to take?
• Would you be open to sharing a sanitized sample file for a joint diagnostic? If yes, what privacy/NDAs would you need in place? Options: Yes — standard NDA, Yes — need data-sharing addendum, Maybe — need to check with legal, No

How Big Could a Surge Really Be — and What Would You Need?

• If a single event increased complex-claim intake by 200% for eight weeks, what would break first?
• Which surge scenarios concern you most? Options: Mass professional liability suits, Regulatory-driven claim spikes, Product failure leading to claims, Construction defect batch claims, Cyber / data breach cascades, Other
• What internal surge-capacity options do you currently have (overtime, temp adjusters, counsel reprioritization, other carriers), and how fast can they scale? Options: Hours, Days, Weeks, Months, We have no scaled option
• What surge commitments would give you confidence from an external partner (select up to three)? Options: Named adjuster pool, Guaranteed onboarding timeline, Staffing uplift within X days, Temporary dedicated counsel panel, Surge-cost model transparency, Real-time capacity dashboard
• How would you measure surge readiness success after the event? What metrics matter most? Options: Time-to-assignment, Avg days to first coverage decision, Spend per claim, Claim backlog size, Customer satisfaction, Reserve accuracy

Quick Check — Who’s in the Room?

• Who will be our primary day-to-day contact for onboarding and technical coordination?
• Which internal teams need access during deployment? (Select all that apply) Options: Claims operations, IT / Integrations, Security / InfoSec, Actuarial / Reserving, Legal / Compliance, Underwriting / LOB leadership, Vendor management
• Who has final sign-off authority to approve data connections, production cutover, and go/no‑go decisions? Options: VP/Head of Claims, CRO/Chief Risk Officer, CISO/Head of Security, Head of IT/Integrations, Other (please name), Multiple people — see notes
• Preferred cadence and channel for deployment coordination (e.g., daily stand-up, weekly exec summary, Slack, Teams, email)? Options: Daily stand-up (video), Twice-weekly check-ins, Weekly status email, Dedicated Slack/Teams channel, As-needed by email/phone, Combination — please specify

If Your Data Could Talk — What Would It Say?

• What core systems currently house claim intake and lifecycle data (choose all that apply)? Options: AMS/Claims system (e.g., Guidewire, Duck Creek), Custom legacy claims system, Carrier portal / insurer-hosted system, Insured's internal system, Email/PDF intake, Third-party data warehouse, Other (please name)
• Which data feeds do you plan to deliver to us for onboarding and ongoing exchange? Please list feed types and owners (e.g., new claim API from AMS — owned by IT).
• What formats and transfer methods do those feeds currently use? Options: Real-time API (REST/GraphQL), Batched API, SFTP/FTPS, Secure file drop / portal, CSV/Excel exports, ETL to data warehouse, Proprietary format / other
• How frequently are each of these feeds expected to update (select typical cadence) Options: Real-time / near-real-time, Hourly, Daily, Once per week, Ad-hoc/manual
• Tell us about the last time a critical feed failed — what happened, how long before it was resolved, and what the impact was?

Where Things Break — Tell Us the Risks You Pretend Are “Under Control”

• Which single data or integration dependency keeps you up at night when you think about cutover? Options: Claim ID reconciliation, Reserve/financials sync, Coverage and policy data accuracy, Party/insured matching, Document transfer reliability, Other — explain
• What are the most common data quality problems we should expect (select all that apply)? Options: Missing required fields, Inconsistent status codes, Duplicate claim records, Incorrect policy/limit mapping, Timestamp or timezone mismatches, Unstructured attachments (scanned PDFs), Other (please describe)
• How are exceptions and feed mismatches managed today? Who owns triage and fixes, and how long do escalations typically take?
• Are there regulatory, court, or jurisdictional constraints that affect data sharing, redaction, or residency for claims in your book? Options: Yes — US state-specific rules, Yes — international/data residency, Yes — confidentiality/NDAs, No known constraints, Unsure — need to check
• In an ideal world, what’s the single operational improvement that would eliminate most of your integration headaches?

Who Will Actually Run the Work — Are They Ready?

• What internal and external claim-handling roles will interact with our team day-to-day (select all that apply)? Options: Assigned adjusters, Coverage counsel, Litigation manager, TPA operations, In-house counsel, Actuarial/reserving, Third‑party vendors (investigators, forensic), Other
• How many adjusters/claims staff will be assigned to this line or portfolio from your side, and what are their typical caseloads?
• Which of these readiness gaps exist today for your assigned staff? Options: No system access / accounts, Insufficient training on our processes, Lacks specialty-line expertise, Conflicting workload/priorities, Clear — no gaps identified
• What training, shadowing, or scenario-based handoffs would make your team feel confident on day one?
• How long does it typically take to provision accounts and tool access for a new vendor/partner at your organization? Options: <1 week, 1–2 weeks, 2–4 weeks, 1–2 months, Longer than 2 months

Gatekeepers and Guardrails — Security, Compliance, and Access

• What’s the one security requirement you assume every vendor must meet — and what would happen if it weren’t met? Options: SOC 2 Type II, ISO 27001, Data encryption at rest and in transit, SSO with SAML/OAuth, Contractual data processing addendum, Other — specify
• Which security/compliance checks will our team need to complete before access is granted? Options: Vendor security questionnaire (VSA), Penetration test / report review, Contractual DPIA / DPA, Proof of insurance/cyber liability, Background checks for staff, Other — list
• Do you require our staff to use VPN, bastion hosts, or specific IP allowlists to connect to your systems? Options: VPN required, IP allowlist required, Bastion host required, No special network constraints, Unsure — need to confirm
• Are there any particular PII/PHI redaction rules, privileged document handling practices, or evidentiary controls we must follow?
• Who on your security or compliance team should we engage for the vendor onboarding checklist, and what timeline do they typically operate on?

How We'll See Progress — Reporting, Metrics, and Integrations

• If you got one report from us every morning that made your CFO breathe easier, what would be in it?
• Which operational and financial KPIs must be available from day one (select all that apply)? Options: Open claim count by severity, Paid & incurred by month, Reserve accuracy vs. actuarial, Litigation spend-to-date, Avg. time to first contact, Defense counsel spend by matter, Subrogation recoveries
• How do you want to receive analytics and dashboards? Options: Direct API into data warehouse, Scheduled CSV/Excel exports, Live dashboard (BI tool), Portal access with drill-through, Ad-hoc reports by request
• Who consumes these reports within your organization and how are they used (e.g., reserving, underwriting, executive reviews)?
• How will we validate reporting accuracy during onboarding — sample files, parallel run, or statistical reconciliation? Options: Parallel run (dual-entry) period, Sample file reconciliations, Full statistical reconciliation by actuarial team, Ad-hoc validation on key files

What Would Make the First 90 Days Feel Like a Win?

• What are the non-negotiable acceptance criteria for a successful initial deployment?
• Which three measurable success signals would convince you we’re delivering value (select up to three)? Options: Reserve accuracy within tolerance, Reduction in litigation leakage/spend, Timely first contact with claimant, Improved reporting timeliness, No data-loss incidents, Smooth surge handling within SLA
• If early results don’t meet expectations, what rapid remediation options would you want to keep in place (e.g., rollback, extended parallel run, targeted triage)? Options: Rollback to prior handler, Extend parallel run, Targeted reconciliation team, Escalation to executive steering committee, Other — specify
• Who is responsible for signing off on final readiness and what evidence will they require?
• How confident are you in hitting your desired deployment date today, and what would increase that confidence? Options: Very confident, Somewhat confident, Not confident — need support, Unsure

Final Logistics — Timeline, Tests, and Next Steps

• What is your target window for first test transfers, staged cutover, and full production cutover? Options: Test transfers within 2 weeks, Test transfers in 2–4 weeks, Staged cutover in 1–2 months, Full production cutover in 2–3 months, Custom timeline — please specify
• Which end-to-end scenario should we prioritize for initial validation (select one)? Options: New claim intake to reserving, Active litigation file transfer, Subrogation/recovery workflow, Privacy-sensitive PII redaction and docs, High-severity catastrophe claim
• Please list any outstanding contractual, legal, or vendor approvals that must be in place before cutover, and estimated completion dates.
• What are the top three blockers we should resolve in the next 7–14 days to keep timeline momentum?
• On a scale from 1–10, how would you rate current readiness to begin technical onboarding (1 = not ready, 10 = fully ready)? Please explain your rating. Options: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10

Let's Start With Who's in the Room

• Who will be our primary point(s) of contact for this exploration? Options: VP / Head of Claims, Chief Claims Officer, Head of Underwriting, Actuary / Reserving Lead, Head of Legal / Coverage Counsel, IT / Data Lead, Other
• Which internal stakeholders must explicitly sign off on a change to claims administration? Options: Claims leadership, Underwriting, Finance / Actuarial, Legal / Compliance, Operations / Technology, Risk Management / Executive Committee, Other
• Who currently owns reserve methodology and final reserve sign-off? Options: Claims Head, Actuarial Team, Finance, Joint Claims & Actuary committee, No single owner / shared responsibility, Other
• What is your target timeline for reaching a preliminary decision about a third‑party claims partner? Options: Immediate (30 days), Near term (1–3 months), Medium (3–6 months), Longer (6–12 months), Undefined / exploratory
• For each stakeholder group you selected, briefly describe what ‘good’ would feel like to them (reserve confidence, litigation control, clarity on coverage, reporting cadence, etc.).

Are You Confident Your Claims Numbers Tell the Whole Story?

• How confident are you in the accuracy of current reserves and loss development metrics? Options: Very confident, Somewhat confident, Neutral / Unsure, Not confident
• Which reserve-related KPIs are used in executive reporting today? Options: Case reserves, IBNR / Bulk reserves, Paid-to-incurred ratio, Reserve adequacy by line, Loss development triangles, None of the above / ad hoc
• How frequently do you reconcile claims system data with actuarial inputs? Options: Daily / near real-time, Weekly, Monthly, Quarterly, Rarely / never
• Tell us about a recent situation where reporting or reserve assumptions led to a material surprise—what happened and who felt the impact?
• Which reporting formats give you the most confidence to make reserving or budget decisions? Options: Actuarial triangles, Rollforward schedules, Loss pick dashboards, Case-level drilldowns, Counsel spend rollups, Other

Where the Claims Engine Is Stalling

• If you had to name one recurring failure that costs you money or time, what would it be?
• Which operational failure modes occur most often in your claims lifecycle? Options: Delayed investigations, Inconsistent coverage analysis, Counsel overspend, Poor reserve changes, Slow closure rates, Data entry / coding errors, Other
• Which claims management systems and tools create the most friction for you today? Options: Guidewire, Duck Creek, Insurity, Homegrown platform, Spreadsheet-centric workflows, Third-party portal(s), Other
• How long have the failure modes you described persisted? Options: Under 6 months, 6–12 months, 1–2 years, 2+ years, New / emerging
• Who is responsible for continuous process improvement in claims and how empowered are they to change workflows? Options: Claims ops / process lead, IT / automation team, Cross-functional governance committee, No clearly empowered owner, Other

When Coverage Questions Become High Stakes

• How often do coverage decisions escalate beyond the adjuster to senior claims, legal, or underwriting? Options: Very often, Occasionally, Rarely, Never / unknown
• Who drafts and reviews reservation-of-rights and denial letters today? Options: Adjuster alone, In‑house coverage counsel, External coverage counsel, Claims + Legal collaboration, No standard practice
• How confident are you that your coverage analyses would withstand regulatory or bad‑faith scrutiny? Options: Very confident, Somewhat confident, Unsure, Not confident
• Give a recent example where coverage interpretation materially changed strategy or cost—what was the consequence?
• What controls do you currently have in place to ensure consistent defense counsel selection and budget governance? Options: Panel counsel with rate guidelines, Pre‑approved firms per specialty, Claims counsel scorecards, No formal controls, Other

If Outcomes Were the Only Thing That Mattered

• Which outcome would you prioritize if you could only pick one to materially improve in 12 months? Options: Reserve accuracy, Reduced litigation spend, Faster claim closure, Coverage defensibility, Predictable surge handling, Improved reporting / transparency
• Select the top three measurable success signals we should use during a pilot. Options: Reserve variance vs actuarial, Average indemnity spend per claim, Defense counsel hourly spend, Time-to-first‑decision, Claim closure rate, Client satisfaction / NPS
• For your top priority outcome, what is the current baseline and what is a realistic target in the next 12 months?
• How would your underwriting, finance, and executive teams use improved claims outcomes when making pricing or capital decisions?
• What reporting cadence and level of granularity would make your team comfortable to monitor these outcomes? Options: Real‑time dashboards, Daily extracts, Weekly summaries, Monthly executive reports, Quarterly deep dives

How Much Surge-Level Storm Are You Really Prepared For?

• If your largest plausible event hit tomorrow, how confident are you that you could scale claims handling effectively? Options: Very confident, Somewhat confident, Not confident, We have no plan
• What is your current peak claims intake (e.g., claims per day/week/month) and expected surge multiple? Options: Under 50 / month, 50–250 / month, 250–1000 / month, 1000+ / month, Unknown / varies
• Do you have pre‑defined surge SLAs or service commitments that a partner must meet? Options: Yes — defined SLAs, Yes — informal commitments, No SLAs, Not sure
• Describe past surge events—what worked, what failed, and what was most painful to stakeholders?
• What vendor performance metrics during a surge would make you feel you had control (e.g., time to triage, percentage routed to SMEs, average days to decision)? Options: Time to triage, Percent routed to experts, Average days to decision, Counsel engage lag, Escalation response time

What Would It Really Take to Hand Over Control?

• What are the single biggest fears that would prevent you from outsourcing complex claims? Options: Loss of quality control, Coverage inconsistency, Data security concerns, Regulatory scrutiny, Cost unpredictability, Cultural misalignment
• Which proof points or guarantees would most reduce those fears (examples: SLAs, sample file validation, joint governance, pilot outcomes)? Options: Pilot with measurable KPIs, Contractual SLAs & credits, Access to adjuster-level data, Joint governance committee, Independent audit / attestation
• Which commercial models are you most open to exploring for complex claims administration? Options: Per-file pricing, Dedicated FTEs / staffing, Blended fee + success fee, Outcome‑based / risk-sharing, Hybrid models
• What non‑negotiable legal, regulatory, or audit requirements must a partner meet before onboarding? Options: Data localization, Regulatory filings support, PCI / SOC compliance, Local counsel requirements, No special requirements
• If we proposed a short pilot, what would the minimum success criteria be for you to move to a broader engagement?

Practical Readiness — Can We Look Under the Hood?

• Can you provide representative claim files and data feeds for a sample validation (with NDA if required)? Options: Yes — several representative files available, Yes — limited anonymized extract only, Yes, but only after a data agreement, No, cannot share sample files
• Which data elements can you share from your claims system (select all that apply)? Options: Policy metadata, Reserve history / rollforwards, Payment ledger, Counsel invoices & spend, Case notes / PDFs, Coverage letters / correspondence, Other
• How frequently can those feeds be delivered for a pilot (and through what mechanism)? Options: Real‑time API / webhook, Daily flat file, Weekly extract, Manual upload via SFTP, Ad hoc / by request
• Are there security, PII, or regulatory constraints we should know about before requesting files? Options: Yes — strict constraints, Yes — standard confidentiality / NDA only, No special constraints, Unsure — need to check
• Would you be willing to do a joint walkthrough of 2–3 live claims (redacted if needed) to observe decision points and expected outcomes? Options: Yes — live walkthrough, Yes — redacted / anonymized, Maybe — need approvals, No

Decision Rhythm — Who Signs What, and When?

• What is the formal procurement or governance path for a vendor approval in your organization? Options: Claims selects + legal review, Procurement-led RFP, Executive committee approval, One-off vendor agreements, Other
• Who are the decision-makers that must be engaged for commercial, legal, and operational sign-off? Options: Claims head, CFO/Finance, Head of Legal, Underwriting leader, Procurement, Board / Executive Committee
• What internal calendar dates or budget cycles would force a decision window (e.g., renewal season, budgeting, regulatory deadlines)? Options: Renewal season, Budget planning / fiscal year, Regulatory filing deadlines, Earnings season, No fixed dates
• What would make you accelerate a decision (e.g., demonstrable savings, regulatory pressure, catastrophic event)? Options: Proven cost savings, Regulatory or litigation risk, Operational failure, Executive directive, Pilot success
• What single next step would be most valuable right now to move this conversation forward? Options: Run a 30–90 day pilot, Share sample files for validation, Joint walkthrough of live claims, Commercial term sheet / pricing, Schedule governance meeting