Getting Comfortable Together

• Tell us your name, role, and the one outcome you expect from a move to self-funding this year.
• Who are the core decision-makers we should engage (title and likely final approver)? Options: CFO, Head of Benefits/Total Rewards, Benefits Consultant, VP Finance/Controller, CEO/Owner, Board/Comp Committee, Other
• What timeline is driving your decision process right now (renewal, fiscal planning, regulatory, other)? Options: Next renewal (0-3 months), 3–6 months, 6–12 months, 12+ months, No fixed timeline
• What’s one past change initiative on benefits or finance that felt successful — and why did it work?
• What keeps you up at night about taking on claims risk directly? Options: Catastrophic claims, Monthly cash volatility, Lack of claims transparency, Administrative burden, Vendor coordination, Regulatory/compliance risk, Other
• How would you like this discovery conversation to help you walk away—what are the top two decisions you want clarity on?

If Your Financial North Star Could Speak — What Would It Say?

• If you had to describe a successful first 12 months of self-funding in one sentence, what would that sentence be?
• Which of these financial outcomes matter most right now? Rank up to three. Options: Lower long-term premium trend, Reduced per‑employee cost, Predictable monthly cash flow, Retained underwriting gain, Improved budgeting accuracy, Protect against catastrophic exposure
• What is your target year‑over‑year medical cost change that would make this move feel successful? Options: > -10% (substantial savings), -5% to -10%, 0% to -5%, No change expected — focus on transparency, I don't have a target
• How do you currently quantify ‘good’ operational performance from a TPA/carrier? List the top 3 metrics you care about.
• When you think about value, how important is the upside (keeping savings) versus downside protection (avoiding surprise losses)? Options: Upside oriented, Balanced, Downside protection prioritized, Unsure / need modeling
• If you had to pick one internal audience to convince first (finance vs benefits leadership vs consultant), which would you choose and why? Options: Finance/CFO, Benefits/Total Rewards, Benefits Consultant, Payroll/HR, Executive Leadership

If a Bad Claims Year Happened Tomorrow — Could You Live With That?

• What level of single‑claim exposure would you consider intolerable without stop‑loss protection (estimate dollar amount)? Options: <$50k, $50k–$250k, $250k–$500k, $500k–$1M, >$1M, Unsure — need modeling
• Do you have a preferred stop‑loss structure today (specific attachment, corridor, aggregate)? If so, what is it and why?
• How do you feel about the trade‑off between lower attachment (more protection) and higher premium/fee cost—what would make you accept more protection? Options: Willing if budget neutral, Willing if clear ROI in 3 years, Prefer to protect minimally, Need scenario modeling to decide
• Which of the following stop‑loss features are must-haves versus nice-to-haves? Options: Specific attachment level flexibility, Aggregate corridor limits, Reinsurance reimbursement timing, Run‑in/run‑out provisions, Claims cost containment incentives, Stop‑loss policy transparency
• Tell us about a time you faced a large claim or surprise cost—how did it affect operations, cash flow, and internal trust?
• How long have you been willing to tolerate claims volatility under current arrangements? Options: Less than 1 year, 1–2 years, 3–5 years, 5+ years, We haven't tolerated volatility — it's been urgent

How Much Cash Flow Swings Can You Actually Sleep With?

• If monthly claims were 25% higher than plan for two months, what would be the immediate operational impact? Options: No impact (we have reserves/line of credit), Short-term cash reallocation, Delay projects/payables, Need emergency funding, Unsure
• Describe your current funding model and cadence (level funding, ASO with claims pay, monthly true-up, banked reserves, etc.). Options: Level funding, ASO – pay claims as billed, Monthly deposits with reconciliation, Funded reserve account, Other
• Which smoothing or liquidity options are you open to exploring? Options: Rolling reserves, Monthly true-up with smoothing, Bank line of credit, Stop‑loss cash flow triggers, Premium financing, None
• How quickly do you need stop‑loss reimbursements to occur after a large claim to avoid operational stress? Options: Within 30 days, 30–60 days, 60–90 days, 90+ days, Varies by claim
• Who in finance will own funding reconciliation and monthly cash forecasting—title and capacity?
• Have you modeled scenarios for claim spikes and their budgetary impact? If yes, how thorough were they and what surprised you? Options: No modeling, Basic scenarios, Moderate modeling with sensitivities, Extensive stochastic modeling

What Would Reporting and Analytics Need to Do to Earn Your Trust?

• If you had one complaint about existing claims visibility, what is it and how long has it bothered you?
• Which analytics capabilities are non‑negotiable for you? Options: Diagnosis-level drilldown, Provider-level spend, Member cohort trends, Real‑time claim feeds, Monthly funding pack, Custom ad‑hoc reporting
• How often do you need reporting to feel confident—monthly, biweekly, daily dashboards, or ad‑hoc? Options: Daily dashboard, Weekly, Biweekly, Monthly, Quarterly
• Who needs access to claims analytics and at what permission levels (finance, benefits, consultant, broker)? Options: Finance (full), Benefits (full), Consultant (read/export), Broker (read only), Senior leadership (summaries)
• What formats and integrations matter most for your tech stack (API, SFTP, CSV, BI tool connectors)? Options: API (real‑time), SFTP batch, CSV exports, Snowflake/warehouse connector, Power BI/Tableau connector, Other
• Give an example of a decision you couldn’t make in the past because data arrived late or was incomplete.

What Would ‘Winning’ Look Like — Beyond Just Saving Money?

• If you could measure three outcomes 12 months after go‑live to judge success, what would they be?
• How important are member experience metrics (call responsiveness, claims accuracy, care navigation outcomes) relative to financial metrics? Options: More important, Equally important, Less important, Not considered currently
• What year‑over‑year percentage change in total medical spend would you celebrate? Options: >10% reduction, 5–10% reduction, 0–5% reduction, No reduction but improved predictability, Other
• What operational SLAs would make you feel we’re delivering (turnaround times, claims accuracy, reporting delivery)? Select top 3. Options: Claims adjudication turnaround, First‑pass payment accuracy, Provider inquiry response time, Monthly reporting delivery date, Stop‑loss reimbursement timing, Data refresh frequency
• How will success be reported internally—what cadence, audience, and decision forums will use these metrics? Options: Monthly finance review, Quarterly leadership, Renewal committee, Board/Owners, Ad‑hoc
• If after 12 months the financial targets are missed but operational goals are met, how would you want to handle renewal decisions? Options: Renegotiate structure, Extend term with improvement plan, Terminate, Escalate to execs for decision

Deal Makers, Deal Breakers, and the Path Forward

• What would be an absolute deal breaker for you in a partnership with a TPA/stop‑loss partner? Options: Slow reimbursement, Poor data access, Opaque fees, Weak clinical programs, Inflexible stop‑loss terms, Other
• What commercial terms or governance commitments would make you comfortable signing today? Options: Fixed admin fee, Transparent pass‑through costs, Guaranteed reporting cadence, Service SLAs with penalties, Renewal governance roles, Other
• Who needs to sign off and what is the expected approval timeline? Please list names/titles and a target date.
• What modeling or artifacts do you need from us to move from interest to commitment (cash‑flow scenarios, stop‑loss quotes, member impact analysis)? Select all that apply. Options: Cash‑flow sensitivity models, Specific & aggregate stop‑loss quotes, Claims trend analysis, Provider network impact, Implementation checklist, SLA draft
• If we were to propose a one‑page pilot or proof period, what would success look like and how long should it run? Options: 3 months, 6 months, 12 months, Pilot not desired
• What are the top three internal objections you expect, and who is best positioned to address each?
• What next step would make this conversation most valuable to you right now? Options: Request modeling, Schedule stakeholder workshop, Receive sample reporting, Get preliminary stop‑loss terms, Other

Starting Point: How You Currently Cover Care

• Which funding model are you operating under today? Options: Fully insured, Level-funded, Self‑funded (TPA), ASO with insurer, Captive, Other
• Who currently administers claims and handles stop‑loss—internal team, a TPA, your insurer, or a mix? Options: Internal benefits team, Third‑party administrator (TPA), Insurer/ASO team, Combined partners, Other
• How long have you been on this funding model? Options: Less than 1 year, 1–3 years, 3–7 years, 7–15 years, 15+ years
• Describe (briefly) any recent changes that led you to adopt or keep this model.
• What internal team owns month‑to‑month funding (payroll, benefits, treasury, or finance)? Options: Finance/CFO, Benefits/Total Rewards, Payroll, Shared ownership, Other

If Your Claims Data Could Be Brutally Honest

• If your claims data could tell a single blunt headline about your plan today, what would it say?
• Over the last 12 months, what pattern best describes your claims spending trend? Options: Steady and predictable, Gradually rising, Highly volatile month to month, A single catastrophic spike, Declining
• What is your typical monthly lag between services rendered and claims reflected in your reports? Options: Less than 7 days, 7–14 days, 15–30 days, 30–60 days, Over 60 days
• How often do you experience significant adjudication backlogs or denials that require manual intervention? Options: Weekly, Monthly, Quarterly, Rarely, Never
• Tell us about a recent claim or claims episode that caused the most frustration—what happened and why?
• Which claims metrics do you trust today, and which do you doubt? (e.g., paid dollars, incurred but not reported, CPT/diagnosis accuracy)

Are Your Vendors Team Players or Lone Rangers?

• Do you feel your vendor ecosystem is designed to collaborate toward your goals—or to minimize each vendor's risk? Options: Collaborative and aligned, Mostly aligned but siloed, Fragmented and defensive, We haven’t evaluated this
• Which vendors currently touch medical claims, network access, RX, stop‑loss, and clinical programs? Options: TPA/Claims Admin, Stop‑loss carrier, PBM, Network/TPN, Care management vendor, Wellness vendor, Other
• How many separate contracts govern benefits administration and stop‑loss today? Options: One integrated contract, Two (TPA + stop‑loss), Three or more, We’re unsure
• How easy is it to get consolidated invoicing, reconciliations, and a single view of liabilities across vendors? Options: Easy and timely, Possible but manual, Very difficult, Not possible today
• Have vendor handoffs ever created an issue that cost you time or money? Please describe the most recent example.
• Do you have data‑sharing or SLAs in contracts that specify timeliness and formats for claims data? Options: Yes, detailed SLAs and formats, Some SLAs but inconsistent formats, No SLAs, We don’t know

The Cash Story: When Benefits Surprise the Ledger

• How often does your benefits funding run differently than the finance team expected for a given month? Options: Almost every month, Several times a year, Rarely, Never
• What is the typical range of month‑to‑month variance (high to low) in benefit costs as a percentage of budget? Options: <5%, 5–10%, 10–20%, 20–50%, 50%+
• When a month spikes, how long does it take to receive stop‑loss reimbursements (if applicable)? Options: <30 days, 30–60 days, 60–90 days, 90+ days, Not applicable
• What working capital or reserve practices do you have for benefits cash flow (e.g., claims float, funded reserves, letter of credit)? Options: Formal reserve account, Ad‑hoc float with treasury, No reserves, Other
• Describe the emotions or internal conversations when finance gets surprised by benefits spend.
• Who on your finance team models benefits volatility and how frequently are those models refreshed? Options: CFO/Controller, Treasury, Benefits analyst, External consultant, We don’t have models

Data: Windows, Not Locked Vaults

• When you request claims data today, is the response a useful dashboard or a frustrating data dump? Options: Actionable dashboard + raw extracts, Dashboard only, Raw extracts only, Delayed and inconsistent, I don’t know
• Which of the following data elements do you have reliable access to (select all that apply)? Options: Member identifiers (de‑identified options), Date of service, Paid amounts, Allowed/negotiated amounts, Diagnosis/CPT codes, Provider NPI/location, Stop‑loss attachment flags
• How long is the typical reporting lag for a complete claims extract (days between DOS and availability)? Options: <7 days, 7–14 days, 15–30 days, 30–60 days, 60+ days
• Do you have API access or automated feeds into your analytics tools, or are exports manual? Options: APIs/automated feeds, Scheduled flat‑file feeds, Ad‑hoc manual exports, No automated access
• What quality issues do you regularly see in claims data (duplicates, mismatched IDs, incomplete codes)? Give examples and frequency.
• If we wanted to run a 12‑month claims cohort analysis for cost drivers, what existing reports or extracts could you share right away? Options: Monthly paid claims by member, Incurred but not reported (IBNR) estimates, Provider contract files, We cannot share right away, Other

Decision Makers and Risk Appetite: Who Pulls the Levers?

• Who ultimately approves changes to funding structure, stop‑loss, and vendor relationships? Options: CFO, Head of Benefits/Total Rewards, Benefits consultant, Board/Executive committee, Finance committee, Other
• How would you describe your organization’s appetite for funding risk: conservative, balanced, opportunistic, or undecided? Options: Conservative, Balanced/moderate, Opportunistic (high risk for reward), Undecided
• What timeline do decision‑makers expect for major benefits changes (immediate, within renewal, 12–24 months)? Options: Immediate (next 30 days), Next renewal (3–6 months), 6–12 months, 12–24 months, Undecided
• Who on your team should we engage to model cash flow scenarios and why?
• When stakeholders disagree on risk, what is the usual tiebreaker (finance opinion, consultant advice, HR leader, CEO)? Options: Finance/CFO, Benefits consultant, HR/Benefits leader, CEO/Exec sponsor, Other

Red Lines and Trigger Points: When Do You Act?

• What single event or metric would trigger you to change vendors or funding approach immediately? Options: A catastrophic claim above X, Repeated adjudication errors, Data access failures, Unexpected cash strain, Regulatory/compliance failure, Other
• Do you have explicit stop‑loss attachment or aggregate corridor thresholds that are considered unacceptable? If so, what are they?
• How quickly would you expect a vendor to remediate a critical issue (pay/reconciliation error, data breach, reporting fail)? Options: <24 hours, 48–72 hours, One week, Longer than one week
• Have you ever exercised contract termination or withheld payment for vendor performance? Please describe the circumstance.
• Emotionally, what keeps you up at night about benefits risk—cash, reputational, compliance, or people impact? Options: Cash volatility, Employee disruption, Regulatory risk, Reputational exposure, Other

If We Could Solve One Thing in 12 Months

• If you could remove one financial or operational headache in the next 12 months, which would move the needle most? Options: Reduce monthly volatility, Faster stop‑loss recoveries, Cleaner claims data, Single vendor accountability, Lower admin fees, Other
• Which metrics would you use to measure success for that goal (select up to three)? Options: Variance to budget (%), Days to stop‑loss reimbursement, Claims data lag (days), Adjudication accuracy rate, Employee satisfaction with benefits, Other
• What analytics or reports would have to exist for your team to feel confident about moving forward? Options: Member‑level paid claims extract, Monthly funding cashflow model, Catastrophic claim forecasts, Provider concentration analysis, Custom KPI dashboard, Other
• Realistically, what internal approvals or resources would be required to pilot a different funding or TPA model?
• What would success look and feel like to the CFO vs. to the benefits leader—where might their priorities differ?

Readiness: Can We Move Toward a Model or Pilot?

• What documents and data could you share within 7–14 days to support modeling (claims extracts, funding statements, stop‑loss contracts)? Options: 12–24 months paid claims extract, Renewal exhibits and stop‑loss policies, Monthly funding statements, Provider contracts, None readily available
• Who would need to be in the room (or on the call) to approve a pilot scope and timeline? Options: CFO, Head of Benefits, Finance lead, Benefits consultant, TPA/vendor rep, Other
• What does an acceptable pilot look like for you: a modeling exercise, a time‑limited parallel adjudication, or a phased live migration? Options: Modeling only, Parallel adjudication/test, Phased live migration, Small population pilot (e.g., one region), Other
• What are your preferred next steps and ideal timeframe for exploring change (options, modeling, pilot)? Options: Start immediately (within 30 days), Within 2–3 months, At renewal (3–6 months), 12+ months, Undecided
• Is there anything else we should know about your current state that would help us design a useful analysis or pilot?

Who’s in the Room (and Who Moves the Needle)?

• Who from your organization will be actively involved in evaluating a move to or optimizing self‑funding (select all who will influence the final decision)? Options: CFO / Finance, Head of Benefits / Total Rewards, HR / Payroll, Benefits Consultant / Broker, Actuarial / Risk, General Counsel / ERISA Counsel, CEO / COO, Other (please name)
• How does final sign‑off typically happen for benefits financial commitments—single approver, committee, or board-level approval? Options: Single approver (name/role), Executive committee, Finance committee, Board approval required, Varies by size of commitment
• What timeline are you aiming for to decide on a new TPA/stop‑loss or transition to self‑funding? Options: Immediate (next 30 days), This quarter, By renewal (3–6 months), 6–12 months, No set timeline
• Who would own the financial model and cash flow monitoring once a self‑funded plan is live? Options: CFO / Treasury, Benefits team, HRBP / Payroll, External consultant, Shared ownership, Undecided

What’s Actually Happening with Your Dollars?

• When you look at last 12 months of claims, what single pattern surprised you most? Options: High-cost outliers, Seasonal spikes, Consistent trend upward, Large one-time catastrophic month, Data gaps prevented insight, Other (explain)
• Which funding model are you operating under today? Options: Fully insured, Level-funded, Admin services only (ASO) + stop‑loss, Self‑funded with captive, Hybrid, Not sure / need to confirm
• How predictable have your monthly cash requirements been over the last two years (PMPM variance or number of months >20% above budget)? Options: Very predictable (few/no large variances), Moderately predictable, Often volatile (several months >20%), Extremely volatile (multiple catastrophic months)
• Which claims data feeds do you currently receive and how timely are they? Options: Real‑time or daily claims, Weekly claims files, Monthly summary reports, Ad‑hoc reports only, No consistent claims feed
• Tell us about one recent claims or vendor data issue you wish had been handled differently—what happened and what did it cost you (time, dollars, trust)?

Where It Actually Hurts (and How Often It Comes Up)

• If a single pain point had to be fixed this year to keep leadership comfortable with self‑funding, what would it be? Options: Cash flow volatility, Stop‑loss clarity and placements, Claims accuracy and speed, Access to usable data, Vendor coordination and accountability, Other (specify)
• How many times in the last 12 months did claims activity trigger a formal conversation with finance or the executive team? Options: Monthly or more, Quarterly, A couple of times, Once, Never
• Have catastrophic claims in the last 3 years required special funding actions (waivers, loans, or board approvals)? If yes, briefly describe frequency/impact. Options: Yes — multiple times, Yes — once, No
• How do these recurring issues feel for you and the team—annoying, risky, paralyzing, or energizing (briefly explain)? Options: Annoying, Risky, Paralyzing, Energetic / Opportunity
• Which vendor relationship causes the most friction today (TPA adjudication, network, stop‑loss carrier, pharmacy, analytics)? Options: TPA adjudication, Network / PPO vendor, Stop‑loss carrier, Pharmacy / PBM, Analytics / Data vendor, Multiple / All of the above

Questioning What You’ve Always Taken for Granted

• What belief about stop‑loss or self‑funding, if proven false, would change your willingness to proceed? Options: Stop‑loss will fully protect cash, TPA transparency is limited but acceptable, Savings are guaranteed over time, Vendor consolidation reduces risk, We can afford short‑term volatility
• Where have you accepted a 'normal' level of service or data delay because changing vendors felt harder than tolerating the problem? Options: Claims speed, Reporting accuracy, Integration with payroll, Provider network issues, Customer service / escalations
• How confident are you in the accuracy of the enrollment and eligibility feeds that would drive funding and adjudication? Options: Highly confident, Mostly confident, Some concerns, Significant concerns / gaps
• If you could remove one internal barrier to change (budget process, executive risk aversion, procurement complexity), which would you pick and why?

If Numbers Could Talk: What Outcome Actually Matters?

• Which single financial outcome would make a move to our TPA + stop‑loss model a clear win for you next year? Options: Reduced PMPM vs. current, Lower variance in monthly funding, Reduced catastrophic exposure, Improved cash flow predictability, Better forecasting / budgeting accuracy
• What target ranges would you consider acceptable for year‑over‑year cost variability and trend? Options: <5% variability, 5–10%, 10–20%, >20%
• Which KPIs would you want in the executive dashboard (select up to 4)? Options: PMPM spend, Loss ratio, Months cash at risk, Number of catastrophic claims, Claims turnaround time, Net savings vs. actuarial
• How often do you want reconciliations and executive funding briefs once live? Options: Weekly, Bi‑weekly, Monthly, Quarterly, Event‑driven only
• What would a successful first 12 months look and feel like to you—quantitatively and emotionally?

Controls You Won’t Compromise On

• Which operational control is non‑negotiable for your team (pick one)? Options: Real‑time claims visibility, Strong stop‑loss attachment/structure, Direct access to raw claims files, Strict SLAs and penalties, Segregated banking / funding controls
• How do you prefer access controls and user permissions to be handled for sensitive claims data? Options: Role‑based access with audit logs, Centralized access via benefits team, Vendor limited views only, Full direct access for finance/actuarial
• What frequency and format of reconciliation would satisfy both payroll and treasury teams? Options: Daily feeds + monthly reconciliation, Weekly summaries + monthly detailed, Monthly detailed only, Custom cadence (specify)
• What level of SLA (turnaround time, accuracy) do you expect from your TPA and stop‑loss partners? Options: Best‑in‑class (tight SLAs + penalties), Industry standard SLAs, Flexible SLAs with escalation, Unsure—need guidance
• Describe any reporting or audit requirements driven by internal governance or external regulations we should be aware of.

Deal Breakers, Deal Makers, and the Roadblocks in Between

• What single factor would make you walk away from negotiating a self‑funded arrangement today? Options: Unacceptable stop‑loss terms, Lack of data transparency, Inability to control cash flow, Poor references / service history, Executive veto
• What evidence or proof points would most reduce your risk perception (claims audit, reference client of similar size, parallel adjudication results, pricing guarantees)? Options: Claims audit, Peer reference, Parallel adjudication test, Guaranteed pricing structure, Detailed servicing roadmap
• What internal due diligence or committee approvals remain to be completed before a final agreement? Options: Finance review, Legal / ERISA review, Procurement, Executive / Board review, Actuarial validation
• Are there procurement or vendor selection rules (RFP, number of vendors, mandatory checks) we should follow? Options: Formal RFP required, Informal competitive process, Sole source allowed, Procurement involvement only at final stage
• What internal champions or skeptics should we loop in early to smooth approval?

A Small, Low‑Risk Step That Could Change Everything

• If we offered a low‑risk pilot or parallel adjudication test, what outcome from that test would make you want to proceed? Options: Matching or better claims accuracy, Improved adjudication speed, Clearer cash projections, No surprises in catastrophic claim handling, Strong service responsiveness
• What specific data would you be comfortable sharing first to run an initial assessment (e.g., 12 months claims, enrollment, premium history)? Options: 12 months claims, Enrollment + eligibility files, Premium and funding history, Stop‑loss claims detail, None / need confidentiality discussion
• How soon could your team commit to a technical kickoff and data share under an NDA? Options: This week, Within 2 weeks, Within a month, 3+ months, Undecided
• Who should we name as the single point of contact to coordinate the pilot, data requests, and executive updates?

Who’s in the room (and who signs the checks)?

• Who will be involved in evaluating funding, vendor selection, and renewal decisions? Options: CFO, Head of Benefits/Total Rewards, Finance team, Benefits consultant/broker, HR/Payroll lead, General counsel/ERISA counsel, Other
• Which single person or title do you expect will have final sign-off on changing funding approach or stop‑loss structure? Options: CFO/Finance leader, Head of Benefits/Total Rewards, Board/Owner, CEO/COO, Shared approval (Finance + Benefits), Other
• What’s your current stance on transitioning from fully insured to self-funding? Options: Actively pursuing change, Exploring options, undecided, Curious but risk-averse, Committed to fully insured for now
• How do you prefer to receive updates and analytical deliverables during an evaluation (format and cadence)? Options: Weekly briefings, Bi-weekly deep-dive meetings, Monthly summary dashboards, Ad hoc requests only, Shared workspace with real-time access, Other
• In one short sentence, what is the primary reason your team is exploring changes to funding or vendors today?

Is volatility quietly eroding your plans?

• How often does claims volatility derail your monthly cash forecasts or capital planning? Options: Every month, Several times a year, Around once a year, Rarely, Never
• When a high-claim month hits, what is the typical financial impact (select the range closest to reality)? Options: < 1% of payroll, 1–3% of payroll, 3–5% of payroll, 5–10% of payroll, >10% of payroll
• How do you currently smooth or fund months with unexpected claims (select all that apply)? Options: Cash reserves, Line of credit, Reserve account with carrier/TPA, Monthly true-up billing, No formal smoothing mechanism, Other
• Who in your organization owns the cash reserve and liquidity strategy for benefits? Options: Finance treasury, CFO, Benefits/HR, Shared ownership, Not defined
• When volatility happens, how does it affect your team emotionally and operationally? Give a short example of the last time it caused friction.

What don’t your reports tell you (but should)?

• If your analytics vanished tomorrow, what critical decisions would you no longer be able to make?
• Which of these data feeds do you currently receive from your administrator or carrier? Options: Paid claims (EOB/837), Raw adjudication detail, Encounter/institutional files, Enrollment files, Provider network discounts, Pharmacy data, None of the above
• How timely and complete are the data feeds you actually get? Options: Daily, near real-time and complete, Weekly, largely complete, Monthly with frequent gaps, Delayed by multiple months, We don’t get usable feeds
• Which metrics do you trust now for steering vendor performance and plan design? Options: Trend by month, Per member per month (PMPM), Top diagnoses, High-cost claimants list, Provider-specific spend, Member-level utilization
• When you ask for an ad hoc analysis or a drill-down, what is an acceptable turnaround and what is the reality?

Are you paying for care you can actually change?

• Roughly what portion of annual medical spend do you believe is avoidable or manageable with better clinical programs and plan design? Options: <5%, 5–10%, 10–20%, 20–30%, >30%
• Which clinical or cost-containment programs are currently in place? Options: Care management / case management, Utilization review / pre-authorization, Chronic condition programs, High-cost claim review, Care navigation, Pharmacy management, None
• How do you currently measure the impact of those programs (examples and frequency)?
• Have you previously tried to modify network strategy, carve in/out services, or change benefit design to lower spend? What stopped or supported that change?
• How do members typically react when cost or clinical programs change—resistance, acceptance, or neutral? Options: Mostly resistant, Mixed reactions, Generally accepting, Not sure / varies

If renewal were happening today, what would keep you up at night?

• What single renewal outcome would make you decline a recommended change or vendor?
• Which renewal levers are highest priority for you this cycle? Options: Stop‑loss attachment points, Aggregate corridor/aggregate stop‑loss, Plan design changes, Administrative fee reductions, Provider network strategy, Funding cadence
• What stop‑loss structure have you historically been comfortable with (specific attachments or % of expected claim)? Options: Low attachment (protects against moderate risk), Medium attachment, High attachment (employer retains more risk), We vary by year, No stop‑loss previously
• How many renewal scenarios do you expect to see before you feel comfortable making a decision? Options: 1–2, 3–4, 5–7, More than 7, Unsure
• Who beyond the usual benefits team must sign-off on renewal assumptions (e.g., treasury, CFO, board)? Options: Treasury/finance, CFO, Executive leadership, Board/owners, Benefits consultant alone, Other

What does success actually feel like—beyond ‘lower cost’?

• If we returned 12 months after launch and you called this engagement a success, list the top three outcomes you would cite.
• Which of these success metrics matter most to your organization? Options: Medical trend reduction, Reduced cash variance, Improved claims adjudication speed, Timely, actionable data access, Provider cost savings, Member satisfaction / NPS, Clinical outcomes improvement
• Which timeframe feels realistic for you to see measurable change from new funding or vendor decisions? Options: 3–6 months, 6–12 months, 12–24 months, More than 24 months
• How would achieving these outcomes change how you engage with your broker/consultant or internal stakeholders?
• Would you be willing to commit to an annual joint governance and performance review if it meant more predictable outcomes? Options: Yes, Maybe with conditions, No

What could quietly sink this transition?

• What hidden barrier, if unaddressed, would almost guarantee failure of a move to self‑funding or a new vendor?
• Which of these operational risks concern you most right now? Options: Poor data quality, Slow or inaccurate claims adjudication, Payroll/enrollment errors, Insufficient stop‑loss terms, Vendor integration failures, Internal political resistance
• Do existing vendor contracts (networks, PBM, etc.) limit what you can change in the short term? Options: Yes—significant constraints, Some constraints but manageable, No constraints, Not sure
• How confident are you that payroll and enrollment files can be accurate and timely on day one of a transition? Options: Very confident, Confident with effort, Low confidence, Not confident
• Who would be the escalation owner inside your organization for funding disputes or material claim issues? Options: CFO/Finance leader, Benefits director, HR/Payroll lead, Assigned project manager, Not yet identified

What’s the smallest step that proves this can work?

• What’s the least disruptive pilot or proof you’d accept to validate modeling, claims flow, and reporting?
• Would you be open to a parallel adjudication or reconciliation pilot before full cutover? Options: Yes—parallel adjudication, Yes—limited population pilot, Only modeling initially, No, prefer direct cutover
• How much historical claims detail are you willing to share for modeling and stop‑loss placement? Options: 24+ months, 12–24 months, 6–12 months, Less than 6 months, None
• What reporting cadence during a pilot would make your finance and benefits teams comfortable? Options: Weekly, Bi-weekly, Monthly, Ad hoc on request
• Which internal approvals are needed to run a pilot (select all that apply)? Options: CFO/Treasury, Benefits/HR, Legal/Compliance, IT/Security, Board/Owners, None / fast-track