Getting Comfortable: Who’s in the Room and Who Moves the Needle

• Who will be our primary day-to-day contact for benefits implementation and administration? Options: Benefits Manager, Head of Total Rewards, HR Operations Lead, Payroll Lead, CFO/Finance Leader, Broker/Consultant, Other
• Which people or teams need to be consulted before a go/no-go decision can be made? Options: Benefits/Total Rewards, HR Leadership, Finance/CFO, Payroll/HRIS, Legal/Compliance, IT/Security, Broker/Consultant, Other
• Who holds final sign-off authority for pricing, contracts, and custodial terms? Options: CFO/Finance, Head of HR/Total Rewards, Procurement, CEO/Founder, Legal, Broker/Consultant, Unsure
• How do decision-makers prefer to receive updates and review materials during evaluation (e.g., short decks, live demos, executive summaries)? Options: Short executive summary (1–2 pages), Live demo + Q&A, Detailed technical packet, Recorded demo and follow-up call, Spreadsheet/financial model, Combination
• Tell us about one recent vendor decision your team made—who drove it, how long it took, and anything that surprised you about the process.

Why Now? The Tipping Point Behind This Search

• What’s the real reason you are exploring a new benefits administration partner right now—what’s causing urgency?
• When did this need first surface, and what events or feedback accelerated it (e.g., audit finding, employee complaints, payroll error, broker recommendation)?
• What timeline are you working toward for a decision and for any live launch (select approximate ranges)? Options: Immediate (30 days), Short (1–3 months), Quarterly (3–6 months), Longer (6–12 months), No set timeline
• If you could wave a wand and fix one thing that prompted this search, what would it be—and why does that matter to your team?
• What would be an unacceptable outcome from this selection process? Options: Missed compliance requirement, Worsened employee experience, Integration delays, Unexpected fees, Poor broker relationship, Other

If It Doesn’t Work: The Real Costs Nobody Likes to Say Aloud

• If this project fails to deliver on expectations, what concrete problems will your team face in the next 6–12 months?
• How would failure show up financially—e.g., audit penalties, incorrect pre-tax processing, unanticipated fees, or turnover costs? Options: Audit/penalties, Payroll reconciliation costs, Increased vendor fees, Higher admin hours, Employee reimbursements/claims, Other
• What compliance or regulatory risks are you most anxious about right now (check all that apply)? Options: IRS contribution limits and reporting, Substantiation for debit card transactions, Eligibility & COBRA handling, Nondiscrimination testing (FSAs), State-specific rules, Other
• How would employees likely react if the new solution introduced friction (e.g., lower adoption, increased service tickets, negative feedback)? Options: Lower adoption, More helpdesk tickets, Direct complaints to HR, Loss of trust in benefits, Minimal visible reaction
• On a scale of 1–10, how much reputational leverage does success on this project give the benefits and finance teams internally? (1 = none, 10 = transformational) Options: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10

Money Talk Without the Awkwardness: Budget, Fees, and Tradeoffs

• How are you thinking about budget for this service—fixed budget, range, or willing to flex for clear ROI? Options: Fixed budget, Budget range, Open to flex with ROI, Not sure yet
• Which fee model resonates most: per-employee-per-month, transactional fees, bundled platform fee, or hybrid? Options: PEPM (per-employee-per-month), Transactional per claim/contribution, Bundled annual fee, Hybrid (PEPM + transactions), Other
• What pricing components are non-negotiable for finance (examples: no surprise custodial fees, predictable per-participant costs, transparent pass-through charges)?
• Would you trade specific capabilities (e.g., advanced investments, mobile features, bespoke integrations) to hit a tighter budget? Which ones would you consider trading? Options: Investment portal, Auto-substantiation tech, Custom integrations, Dedicated service team, Extended SLAs, Not willing to trade
• Who needs to approve the final pricing structure (role or team), and what internal approval hurdles should we anticipate? Options: CFO/Finance, Head of HR, Procurement, Legal, Broker/Consultant, Other

What ‘Good’ Actually Looks Like for HR, Benefits, and Finance

• If HR, Benefits, and Finance each wrote down a single success metric for this program, what would each department list?
• Which of these measurable success signals matter most to you: adoption, reconciliation accuracy, time-to-resolution for ticket, or cost savings? Options: Participant adoption rate, Payroll reconciliation accuracy, Average support resolution time, Cost savings vs current vendor, Regulatory compliance score, Other
• What target numbers or thresholds would make leadership comfortable (e.g., X% adoption year-one, Y reduction in admin hours)? Please be specific if possible.
• How will you measure and report success internally (dashboard, monthly scorecard, quarterly business review)? Options: Real-time dashboard, Monthly scorecard, Quarterly business review, Ad-hoc executive summary, Other
• Which stakeholder’s perception will determine whether this is seen as a success, and what will they be watching for? Options: Head of HR, CFO/Finance, Benefits Manager, Broker/Consultant, CEO/Founder, Other

Integration Reality Check: Payroll, HRIS, and Data Flows

• If integration becomes the bottleneck, are you prepared to pause rollout or run phased workarounds?
• Which payroll and HRIS systems are currently in use and which will need to exchange data with the benefits platform? Options: ADP (various), Workday, UKG/Ultimate Kronos, Ceridian, Paylocity, Gusto, Other
• What integration methods do you prefer or require: API real-time sync, SFTP batch files, or manual CSV uploads? Options: API (real-time), SFTP (scheduled files), CSV manual uploads, Middleware (e.g., integration platform), Other
• Describe recent integration friction you’ve experienced (mapping errors, field mismatches, payroll timing issues)—how long did it take to resolve and who led the effort?
• What security, SOC, or vendor access requirements must we meet before integrations can begin? Options: SOC 2 Type II, ISO 27001, Custom security questionnaire, VPN or IP allowlist, MFA for admin users, Other

The Human Side: Participant Experience, Adoption, and Support

• Are employees silently struggling with accounts or loudly complaining—what’s the culture around benefits usage? Options: High frustration / vocal, Frustration but quiet, Generally satisfied, Indifferent / low engagement, Mixed
• Which participant pain points come up most often in support tickets (e.g., card declines, balance confusion, claims denial, delayed reimbursements)? Options: Card declines, Confusing balances, Manual claims burden, Substantiation denials, Slow reimbursements, Enrollment errors, Other
• What channels do employees prefer when seeking help (phone, chat, email, in-app), and how important is 24/7 support to you? Options: Phone, Live chat, Email, In-app messaging, Self-service portal, 24/7 support required, 24/7 not required
• How do you currently promote account adoption and engagement (onboarding communications, enrollment campaigns, incentives)? Which has been most effective?
• If we could improve one participant experience immediately (e.g., instant card approvals, auto-substantiation at POS, mobile receipt upload), which would move the needle most for your population? Options: Instant card approvals, Auto-substantiation, Mobile receipt capture, Clear balance visibility, Faster reimbursements, Education/onboarding

Broker & Third‑Party Dynamics: Partners, Pulls, and Politics

• Is your broker actively advocating for a change in vendor, neutral, or preferring the status quo—and why do you think that is? Options: Actively advocating, Neutral, Prefers status quo, Not involved, Unsure
• What expectations do you have for broker involvement during procurement and after go-live (commission structure, training, account management)? Options: Lead negotiations, Support communications, Ongoing service, Commission-based, No broker role post-sale, Other
• Have third‑party relationships (broker, TPAs, payroll vendors) ever blocked a change? Tell us one example and how it was resolved or left unresolved.
• Which contractual or commercial terms are non-negotiable from the broker/third-party perspective (e.g., commission continuity, client ownership, transition assistance)?
• How would you like us to involve your broker or other third parties during discovery and negotiation? Options: Include in all meetings, Share materials only, Coordinate a joint session, Exclude until selection, Other

Where You Really Start: A Quick Snapshot

• Which account types are you currently administering today? Options: HSA, FSA (Health), FSA (Dependent Care), HRA, Commuter, All of the above, Other
• Approximately how many total participants across all account types (best estimate)? Options: Under 1,000, 1,000–5,000, 5,001–20,000, 20,001–100,000, 100,000+
• Briefly describe your current plan designs and any unique provisions we should know about (eligibility rules, employer contributions, carryover limits, grace periods, etc.)
• Who handles day-to-day administration and participant support today? Options: In-house HR team, Third-party administrator (vendor), Broker-managed, Hybrid (internal + vendor), Other
• Who is your primary broker or benefits consultant today (if any)? Options: None / direct, Aon, Mercer, Willis Towers Watson, Buck, Other
• Which payroll provider(s) do you currently integrate with (select all that apply)? Options: ADP, Workday, Paychex, UKG/ Kronos, Ceridian, SAP SuccessFactors, Other, Multiple

If Something's Broken, Where Do You See It First?

• When benefits "just work" you hardly notice—what early sign have you learned actually predicts larger failures or escalations?
• What are the top three participant complaints you hear most often? Options: Card declines, Difficulty submitting claims, Slow reimbursements, Confusing balance information, Mobile app issues, Eligibility confusion, Poor customer service, Other
• How many compliance incidents, audits, or formal notices has your organization received in the last 24 months? Options: None, 1, 2–3, 4–6, 7+
• Describe the most recent incident that caused senior leadership concern — what happened, what was the root cause, and what was the operational or financial impact?
• How frequently are transactions or claims routed to manual processing today? Options: Almost always manual, Mostly manual with some automation, About half and half, Mostly automated, Fully automated

Where Your Data Gets Held Hostage

• If your payroll and benefits data could speak, what would it complain about most often?
• What is your payroll file cadence and format (select all that apply)? Options: Per-pay-period flat file, End-of-month batch, Real-time API feeds, Manual uploads via portal, EDI, Other
• How do you deliver payroll and eligibility files to your current vendor(s)? Options: SFTP, API (REST), Vendor portal upload, Secure email, EDI, Other
• Who owns and maintains the payroll-to-benefits mapping (deduction codes, employee IDs, cost centers)? Options: Payroll team, Benefits admin / vendor, Third-party consultant, Shared responsibility, Other
• How often do you reconcile payroll deductions to posted participant activity? Options: Daily, Per payroll, Weekly, Monthly, Quarterly, Never
• Are there recurring data fields you find are frequently missing or mismatched (example: SSN, hire date, employee ID)? If so, which ones?

What It Feels Like To Your Employees

• Beyond the transactions, what's the single experience that makes employees either love or resent your benefits program?
• Which participant touchpoints cause the most frustration (select all that apply)? Options: Card transactions / declines, Claims submissions, Balance visibility, Enrollment process, Receiving reimbursements, Customer service responsiveness, Mobile experience, Other
• On average, how long does it take to resolve a participant support issue? Options: Within hours, Same day, 1–3 days, 3–7 days, More than a week
• Do you track participant satisfaction (NPS or CSAT)? If yes, which and how frequently do you measure it? Options: We track NPS regularly, We track CSAT regularly, We track both, We don't track participant satisfaction
• If you track satisfaction, what was the most recent score and the date (or leave blank if not tracked)?
• Roughly what percentage of participants use mobile app vs web portal vs phone support (estimates are fine)?
• How often do employees experience a card decline for eligible purchases? Options: Very frequently (daily/weekly), Occasionally (monthly), Rarely, Never, Don't know

Where Compliance Is Quietly Fragile

• Which compliance assumption in your current setup would make leadership lose sleep if it turned out to be wrong?
• Which compliance areas concern you the most (select all that apply)? Options: Substantiation of expenses, HSA contribution limits & eligibility, FSA use-it-or-lose-it rules, Nondiscrimination testing, COBRA/retiree rules, HIPAA/Privacy, ERISA reporting, Other
• How is substantiation handled today? Options: Auto-substantiation at POS, Manual claims with receipts, Third-party vendor validation, Employer-reviewed, Other
• Approximately what percent of medical transactions are auto-substantiated today (estimate)? Options: 0–10%, 11–30%, 31–60%, 61–90%, 91–100%, We don't know
• Do you perform nondiscrimination testing for FSAs/other relevant plans? If yes, when was the last test and were any remediation steps required? Options: Yes — completed within last 12 months, Yes — completed >12 months ago, No, We outsource testing

Imagine the Payroll Process with No Surprises

• What single payroll-related problem, if solved, would free up the most time for your team?
• What baseline level of payroll integration do you require? Options: Real-time API sync, Per-pay-period mapped file with automated ingest, End-of-cycle batch with reconciliation, Manual upload only, No integration — vendor handles separately
• Which payroll identifiers must be preserved or mapped precisely (examples: employee ID, earnings code, cost center)?
• What SLAs do you require for payroll file processing and error correction? Options: Same-day resolution, 24–48 hours, 3–5 business days, Weekly, Other
• What tolerance do you have for payroll deduction errors before escalation (choose the closest threshold)? Options: 0%, <0.1%, 0.1–0.5%, 0.5–1%, >1%, We don't measure
• Would you require a pilot payroll cycle or test window before full cutover? Options: Yes — mandatory, Preferred but not mandatory, Optional, No

The Hidden Operational Costs You're Carrying

• If you were to price the time your team spends fixing benefits issues, what would surprise you most about the cost?
• How many full-time equivalents (FTEs) support benefits administration today? Options: None (fully outsourced), 1–2, 3–5, 6–10, 10+
• Estimate weekly hours your HR/admin team spends on participant support, reconciliation, and manual claims work. Options: <5 hrs, 5–15 hrs, 15–40 hrs, 40–80 hrs, >80 hrs
• What fees are you or your employees paying today for administration, cards, custodial or investment services? Please list or estimate.
• Do you experience cost leakage (unvalidated reimbursements, forfeitures, reconciliation shortfalls)? If yes, provide an estimate of annual impact or how you measure it. Options: None known, Under $10k, $10k–$50k, $50k–$200k, >$200k, Don't know
• Are there internal process workarounds you've built to cover vendor gaps? Describe the workaround and its ongoing cost or risk.

Security, Controls, and Data Governance — The Unforgiving Checklist

• Which security assumption are you currently leaning on that would be unacceptable to a regulator or auditor?
• Which vendor certifications or attestations are mandatory for you (select all that apply)? Options: SOC 2 Type II, ISO 27001, HIPAA, PCI-DSS, FedRAMP, Other, None mandatory
• Do you require single sign-on (SSO) and, if so, which identity providers do you support or prefer? Options: Yes — Okta, Yes — Azure AD, Yes — Ping, Yes — Other, No SSO required
• Do you have data residency or subcontractor restrictions (for example, US-only processing)? Please describe. Options: US-only data processing required, Offshore allowed with controls, No restrictions, Unsure
• Who in your organization signs off on security and privacy assessments (title/role)?

Deciding to Change — What Will It Take?

• What internal policy or entrenched belief tends to kill otherwise good vendor solutions before they get a fair shot?
• Which stakeholders must sign off on a vendor selection (select all that apply)? Options: Benefits manager, HR leadership, CFO / Finance, Legal / Compliance, IT / Security, Procurement, Broker / Consultant, Other
• What are the top three non-negotiable contract terms or commercial constraints for you?
• What is your desired timeline for decision and go-live? Options: Immediate (30 days), 60–90 days, 3–6 months, 6–12 months, 12+ months
• Would you require a pilot or phased rollout? If yes, what scale or population would you prefer for the pilot? Options: Small pilot (single site or 5–10% employees), Medium pilot (20–30%), Phased by population or geography, Full rollout, No pilot
• Six months after deployment, what measurable signals would tell you this project is a success (list adoption, compliance, financial and experience metrics)?

Quick Introductions — Who's Driving This?

• What is your title and which team will own day-to-day coordination with a new benefits vendor? Options: Benefits Manager, Head of Total Rewards, CFO/Finance Lead, HRIS/IS Team, Broker/Consultant, Other
• How many employees will be in scope for the initial launch? Options: <250, 250–999, 1,000–4,999, 5,000–19,999, 20,000+
• Which benefit accounts are highest priority for this initiative? Options: HSA, FSA (Health), FSA (Dependent Care), HRA, Commuter/Transit/Parking, All of the above, Other
• In one sentence, what prompted you to explore a new vendor at this time?
• Who else outside your immediate team should be included in conversations (names or roles)?

If We Keep Doing What We’re Doing, What Breaks Next?

• When you think about the current program, what single recurring failure causes the most pain (e.g., late deductions, card declines, substantiation backlog)? Options: Payroll misposting, Participant confusion/complaints, Regulatory non-compliance risk, Manual reconciliations, Excessive fees, Other
• How often does that issue surface in a way that requires escalation? Options: Multiple times per week, Weekly, Monthly, Quarterly, Rarely
• When those failures happen, whose time and resources are most affected (select all that apply)? Options: Benefits team, Finance/Payroll, HRIS/IT, Senior HR leadership, Employees/Participants, Broker/Consultant
• Tell us about a recent situation where it caused real pain—what happened and what was the impact?
• How has that ongoing pain changed how you feel about your benefits program or your willingness to recommend it internally? Options: Very frustrated — I avoid recommending it, Somewhat frustrated — I raise concerns occasionally, Neutral — it’s manageable, Generally satisfied

Where Compliance and Finance Could Literally Keep You Up at Night

• If a compliance or custodial error happened tomorrow, who would bear the primary risk and why? Options: Benefits team, Finance/CFO, Compliance/legal, Payroll, Broker, Other
• Which measurable outcomes will make HR and Finance declare this a success (pick top 3)? Options: Employee adoption rate, Payroll error rate, Time saved on admin, Cost avoided via compliance, Participant satisfaction score (NPS), Reduced substantiation backlog, Other
• What absolute maximum tolerance can Finance accept for payroll errors or reconciliation discrepancies during steady state? Options: 0% (zero tolerance), <0.1%, 0.1–0.5%, 0.5–1%, >1%
• Are there contract or custodial terms that would be deal-breakers for Finance (e.g., liability caps, audit access, insured sweep)? Options: Yes — custodial terms, Yes — liability/indemnity, Yes — audit/SLAs, No deal-breakers identified, Unsure
• Please list any regulatory or internal compliance standards we must meet (IRS rules, ERISA, SOC2, SOC1, ISO, internal policies, etc.).

What Would Make HR and Employees Cheer?

• Imagine your team announces the vendor switch and employees actually applaud—what would you have delivered to earn that reaction?
• Which participant experience improvements matter most to you (select top 3)? Options: Real-time debit transactions, Auto-substantiation at POS, Mobile receipt capture, Faster reimbursements, Clear balance visibility, Investment portal for HSA
• What target adoption or engagement metric would make you feel this is a clear win after 12 months? Options: Enrollment rate % (open field), Active usage rate % (open field), Average transaction frequency per participant (open field)
• How important is a polished consumer mobile experience on a scale from critical to optional? Options: Critical — primary decision driver, Very important, Moderately important, Nice-to-have
• Describe one employee story you wish the program would produce (how would their experience change?).

The Unsaid Reality: Data & Integrations That Make or Break Launches

• How confident are you that your payroll/HR systems can export the clean, normalized data we need without heavy transformation? Options: Confident — standard exports available, Somewhat confident — minor mapping required, Not confident — heavy transformation/custom extracts, We don’t know yet
• Which payroll and HR platforms will we need to integrate with (select all that apply)? Options: Workday, UKG/UltiPro, ADP, Paylocity, Ceridian, SAP SuccessFactors, Custom/internal payroll, Other
• Who owns the single source of truth for payroll and eligibility data, and how quickly can they provide sample extracts for mapping? Options: HRIS, Payroll, Finance, Broker, Other/uncertain
• Are there any security, SSO, or environment constraints (e.g., restricted test environment, firewall rules, no VPN) that have tripped up past integrations?
• Do you have a preferred cadence or window for payroll runs and data handoffs we must align to? Options: Bi-weekly, Semi-monthly, Monthly, Custom/run-dependent, Unsure

People, Power, and Procurement — Who Actually Signs Off?

• If we had a flawless demo, who would still need convincing and why might they hesitate? Options: CFO — cost/vested interests, Legal — contract risk, IT/Security — integrations, Benefits leader — change fatigue, Broker — incumbent relationship, Other
• Who holds final budget approval and what funding constraints or windows should we know about? Options: CFO/Finance, HR Leadership, Procurement, Business Unit Heads, Broker-managed, Other
• What internal politics or vendor relationships have previously slowed benefits decisions here?
• What timeline does Procurement expect for vendor selection and contract negotiation? Options: 4–6 weeks, 6–8 weeks, 2–3 months, 3–6 months, Flexible/uncertain
• Who needs to be included in our next call to keep momentum (list roles or names)?

Constraints That Matter — What Won’t Bend

• What are the non-negotiable constraints from HR or Finance we must meet to even be considered? Options: Specific custodial bank, Certain SLA/uptime, SOC2/ISO certification, Integration method, Fee structure limits, Specific participant features, Other
• Are there legal or broker-driven contract modules that must be included (e.g., indemnity, audit rights, fee pass-through)? Options: Yes — legal modules required, Yes — broker modules required, No mandatory modules, Unsure
• How flexible is your organization on pricing model (per-participant, per-transaction, flat fee, revenue-share)? Options: Require per-participant, Prefer per-transaction, Prefer flat fee, Open to multiple models, Must be revenue-neutral to current spend
• What internal red lines would cause you to walk away during contracting?

If We Could Prove It Fast — What Pilot Would Convince You?

• If you had to pick a low-risk pilot that would prove value in 60–90 days, what would it be (scale, population, account type)? Options: Small team pilot (<100), Single location or BU, New hires only, HSA-only pilot, FSA-only pilot, Commuter pilot, Other
• What success criteria must the pilot hit for you to greenlight wider rollout (select up to 3)? Options: Error-free payroll runs, Target adoption %, No major participant complaints, Reconciliations balanced, Positive NPS, Integration completed on time
• What pre-launch artifacts will you commit to providing to make a pilot meaningful (data extracts, approvals, pilot communications)? Options: Clean payroll extract, Eligibility file, Signed pilot SOW, Communications template, Stakeholder availability for UAT, Other
• How quickly can decision-makers review pilot results and make a go/no-go call? Options: Within 2 weeks of pilot end, 2–4 weeks, 1–2 months, Longer/uncertain
• What would feel like a reasonable next step after a successful pilot? Options: Expand to full population, Run a second, larger pilot, Proceed to contracting, Revisit scope and timelines, Other

Final Reflection — What Keeps You Up (and What Lets You Sleep)

• What’s the single biggest fear about switching vendors that keeps you up at night?
• What’s the single most compelling reason that would make switching feel worth it?
• On a scale from 1–10, how urgent is solving this problem for your team right now? Options: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10
• Who should we follow up with for technical details, contracting, and pilot planning (include name, role, and best contact method)?
• Is there anything else we haven’t asked that would change how we design a pilot or proposal for you?

Quick Intro: Who’s in the Room and What Matters Most?

• Tell us who will be part of the decision team and what role each person plays in benefits, HR, finance, or procurement.
• Which of these stakeholders will need to sign off before we can move from discovery to commercial review? Options: Benefits Manager, Head of Total Rewards/HR, CFO/Finance Lead, Procurement, IT/Security, Broker/Consultant, Other
• Which deadline or business event is driving your timeline (e.g., open enrollment, fiscal year, renewal)? Options: Open enrollment, Plan year start, Fiscal year planning, Contract renewal, Regulatory deadline, Other
• What’s the one outcome from this evaluation that would make your team say, “This was worth it”?

Are We Aligned on What 'Good' Actually Looks Like?

• If your benefits program were performing at its best, what would that feel like for HR, finance, and employees?
• Which measurable signals will you use to judge success? (Select all that apply.) Options: HSA adoption rate, FSA/DCF utilization, Reduction in manual claims, Payroll reconciliation accuracy, Time-to-resolution for participant support, Net Promoter Score (participant), Cost savings / fee reduction, Compliance violations reduced
• Which of those signals is the highest priority to your team right now? Options: Adoption/engagement, Compliance/risk reduction, Operational efficiency, Cost/fees, Participant experience, Other
• If we solved only one priority in the next 12 months, which one should it be and why?

What's Broken Today — The Problems You’ve Learned to Live With

• What recurring participant complaints or friction points create the biggest workload for your team?
• How often do payment or substantiation issues escalate to HR or payroll (e.g., disputes, reversals, manual adjustments)? Options: Weekly, Monthly, Quarterly, Rarely, Never
• Tell us about a recent case that felt emblematic of your current service or operational pain—what happened and what was the impact?
• Which participant-facing features currently underperform or are missing (select all that apply)? Options: Real-time card transaction approvals, Auto-substantiation, Mobile receipt upload, Investment portal for HSA, Clear balance and claim tracking, Fast support via phone/chat, Online enrollment/changes
• How does that underperformance affect employee behavior—do people stop using accounts, call HR, or submit manual claims?

How Payroll, Data, and Integrations Really Flow (Not How You Wish They Did)

• Walk us through your current payroll vendor(s) and how contributions are submitted — who prepares files and how frequently? Options: ADP, Workday, UKG, Paychex, Ceridian/Dayforce, SAP SuccessFactors, Custom/Outbound feed, Other
• How do payroll and eligibility data reach your benefits vendor today (e.g., SFTP file, API, HRIS push, manual entry)? Options: SFTP (batch), API (real-time), HRIS export, Manual upload, Vendor portal entry, Other
• What percentage of payroll deductions are automated vs. manually adjusted on your side? Options: >90% automated, 70–90% automated, 50–70% automated, <50% automated, Unsure
• Have you experienced recurring data reconciliation gaps (e.g., mismatched SSNs, contribution mismatches)? If yes, how long have they persisted and what's the typical fix?
• What would you change about the payroll-to-benefits handoff if you could wave a wand?

Compliance Reality Check: Where Risk Lives and What Keeps You Up at Night

• When was the last time you had a compliance issue (limits, substantiation, nondiscrimination) and what was the outcome?
• Which compliance areas do you feel least confident about today? Options: IRS contribution limits, Eligibility verification, Substantiation/receipts, FSA nondiscrimination testing, COBRA/COBRA-like rules, Plan document accuracy, Other
• How do you currently handle substantiation for card swipes—do you rely on auto-substantiation, manual claims, or vendor review? Options: Auto-substantiation at POS, Auto-substantiation + manual review, Manual claims only, Vendor adjudication, Other
• Have you had an external audit or IRS inquiry related to these accounts in the past 3 years? If so, what lessons did you take away? Options: Yes—formal audit, Yes—informal inquiry, No, Not sure
• What compliance controls or reporting would make you feel comfortable escalating fewer issues to legal or finance?

Money Matters: Custody, Fees, and the CFO’s True Concerns

• If finance could change one thing about the way benefit dollars are held, invested, or reported, what would it be?
• Which custodial or banking relationships are currently acceptable and which would trigger additional review from your finance team? Options: Bank A (existing), Bank B, Custodian model, Segregated trust, We require RFP for new custodians, Other
• How important is transparent fee reporting versus lower headline fees when evaluating vendors? Options: Transparency is more important, Lower fees are more important, Both equally important, Unsure
• What pricing models are you open to discussing (select all that apply)? Options: Per-participant per-month (PPPM), Per-transaction, Administrative fee + interchange share, Bundled flat fee, T&M implementation, Other
• Are there any finance-level acceptance criteria (e.g., audit trailing docs, SOC2, custody attestations) that must be met before procurement signs?

Implementation Anxiety: What Would Make Go‑Live Feel Safe?

• What are the top three things that, if they fail during go‑live, would be considered a showstopper?
• Which deployment approach do you prefer: big-bang, phased rollout by population, or pilot-first (and why)? Options: Big-bang, Phased by group/location, Pilot-first, Other
• How many pilot participants would feel statistically meaningful to your team, and which populations should we prioritize? Options: <50, 50–250, 250–1,000, >1,000, Unsure
• Which internal teams need early validation (IT, security, payroll, benefits ops) and what specific checks do they require? Options: IT/integration, Security/compliance, Payroll, Benefits ops/admin, Finance, Broker/consultant
• What does a successful pilot look like numerically and behaviorally (e.g., error rate, enrollment %, time-to-pay)?

Decision Momentum: What Could Speed This to a Yes—or Kill It

• What are the top three objections you expect from any stakeholder reviewing this change?
• Who typically acts as the champion inside your organization for benefits platform changes, and what do they need to be convinced?
• How does your broker or consultant influence the decision—are they advisory, required approver, or neutral? Options: Advisory only, Required approver, Heavily influential, Not involved, Other
• What internal procurement or contracting milestones must we hit before legal and finance will execute (e.g., SLAs, indemnity terms, data processing addendum)?
• Realistically, what would accelerate a final decision in the next 60–90 days? Options: Pilot success, Budget approval, Executive endorsement, Broker recommendation, Contract template alignment, Other