Opening: What pushed this to the top of the agenda?

• What specific incident or trigger led you to consider outsourcing benefits administration now? Options: Botched open enrollment, High cost of error remediation, Regulatory/compliance concern, Executive/Board escalation, Broker/consultant recommendation, Other
• Tell the story of that incident—who noticed it first, what went wrong, and how it unfolded day by day?
• Which executives expressed concern and how vocal was the Board or legal team about potential exposure? Options: CHRO, CFO, General Counsel, Board member(s), Head of Benefits, Other
• How do you feel about where things stand today—confident, anxious, outraged, resigned, or something else? Options: Confident, Anxious, Angry/Frustrated, Resigned/Overwhelmed, Motivated to change, Other

Can you really afford to accept this level of risk?

• How many employees were materially affected by the most recent enrollment/eligibility failure? Options: <50, 50-199, 200-499, 500-999, 1,000-4,999, 5,000+
• What was the approximate duration of coverage disruption for affected employees? Options: Less than 24 hours, 1–3 days, 4–7 days, More than a week
• Estimate the near-term financial impact you’re tracking (remediation costs, claim denials, potential litigation, reputational loss).
• Which legal or regulatory exposures worry you most right now (ERISA, state laws, HIPAA, other)? Options: ERISA, State insurance law, HIPAA/PHI, ACA reporting, COBRA compliance, Unsure / need counsel

Who must be convinced before anything changes?

• Which roles will sign off on a move to an outsourcer (title-level)? Please select all that apply and then name the persons in the next question. Options: CHRO/Head of People, SVP Total Rewards/Head of Benefits, CFO, General Counsel, Procurement, IT/Security, Board representative, Benefits consultant/broker
• Who are the specific decision-makers and influencers (names and titles)?
• How does your procurement process typically work for a strategic HR operations vendor—RFx, proof-of-concept, reference checks, SOC review, legal markup? Options: RFx with scoring, Pilot/PoC then contract, Reference-first then legal, Direct negotiation, Other
• How important are consultant/broker endorsements to your internal decision path? Options: Critical, Very important, Somewhat important, Not important

What does this feel like on the front lines?

• Today, what are your service metrics—first-call resolution, average handle time, abandon rate, SLA adherence—for benefits inquiries? Options: FCR >=95%, FCR 90–94%, FCR 80–89%, FCR <80%, Unknown / not measured
• What are the top 5 reasons employees call your benefits team during open enrollment and year-round?
• Share a recent example of a call or case that escalated to leadership—what happened and why did it go unresolved at first level?
• How do employees describe their experience—confused, reassured, frustrated, or trusting—and how does that affect HR workload or escalations? Options: Frustrated/angry, Confused, Generally satisfied, Trusting but cautious, Mixed

Where are your processes quietly leaking value?

• How many active vendor/carrier integrations do you manage today (including EDI feeds, broker systems, and third-party administrators)? Options: <10, 10–24, 25–49, 50–99, 100+
• Which parts of eligibility and enrollment are manual or batch-driven instead of real-time? Options: Enrollment activation, Eligibility reconciliation, Carrier transmissions, COBRA lifecycle, ACA file generation, None / fully real-time
• When a carrier mismatch or error occurs, what is your typical end-to-end remediation workflow and average time-to-resolution?
• Which systems own your single source of truth for active enrollment (HRIS, payroll, third-party admin, hybrid)? Options: HRIS, Payroll, Third-party admin/TPA, Multiple systems—no single source, Other

If we could guarantee 'no surprises,' what would that actually look and feel like?

• Which measurable outcomes would make you feel the problem is solved (select and then specify targets)? Options: First-call resolution, Time-to-coverage activation, Carrier error rate, Remediation costs, Employee NPS, SLA adherence
• What exact targets would you set for your top three success signals (e.g., FCR 95%, activation within 4 hours, remediation cost <$X per incident)?
• How much flexibility do you have on timeline—how quickly do you need to see pilot results and a go/no‑go decision? Options: Immediately (weeks), 1–3 months, 3–6 months, 6+ months
• Which security and compliance proofs are non-negotiable before you move forward (SOC 2 Type II, ISO, penetration test reports, other)? Options: SOC 2 Type II, ISO 27001, Penetration test report, Business Associate Agreement (BAA), Other

Would you be willing to stress-test us where it matters most?

• Are you open to running a parallel service period where our team handles a subset or all live traffic while your team continues operations? Options: Yes—full parallel run, Yes—sample parallel cases, Maybe—need details, No
• Would you permit mock-call audits and triaged real scenarios run against your most complex plan designs? Options: Yes—mock calls allowed, Yes—with restrictions, Maybe—requires NDA, No
• Which complex plan elements must be included in any technical test (multi-carrier plans, COBRA interaction, non-standard eligibility rules, ACA special cases)? Options: Multi-carrier, COBRA interplay, Erratic payroll schedules, Union/Collective bargaining specifics, Custom eligibility rules, All of the above
• What acceptance tests or scorecards would you require to certify a successful simulation (carrier EDI success, mock-call score >=X, SLA performance during parallel run)?

How will you judge whether a commercial and legal deal is trustworthy?

• How many reference checks from comparable employers do you expect before proceeding? Options: 1, 2, 3, 4+
• Which SLA metrics must be contractually guaranteed and which are negotiable (FCR, activation SLAs, error remediation time, uptime, security breach response)? Options: FCR, Activation SLA, Error remediation time, System uptime, Security incident response
• What commercial protections matter most to you—service credits, termination rights, transition assistance, price protections, indemnities? Options: Service credits, Termination for convenience, Transition assistance / run-out, Price caps, Indemnities
• What internal approvals are required for legal and commercial terms (General Counsel sign-off, CFO sign-off, Board notification)? Options: General Counsel, CFO, CHRO, Procurement, Board

Who will lose sleep during transition—and how do we keep them confident?

• Do you expect any of your in-house benefits specialists to leave during transition, and how would that affect institutional knowledge? Options: Yes—likely, Possible, Unlikely, No
• What knowledge-transfer methods have worked before (shadowing, documentation, recorded sessions, job aids), and which do you prefer now? Options: Shadowing/on-the-job, Recorded sessions, Written SOPs, Runbooks/checklists, All of the above
• What staff-to-client ratio do you believe is required to maintain service quality during and after onboarding? Options: 1:50, 1:100, 1:200, Other / unsure
• How do you want employee communications handled during transition—template-driven, co-branded, fully owned by outsourcer, or managed internally? Options: Outsourcer-owned, Co-branded, Employer-owned, Hybrid

What would make you say 'Yes'—and when?

• What is your target timeline for a procurement decision and potential contract signature? Options: Within 30 days, 1–3 months, 3–6 months, 6+ months
• What are the three non-negotiable signals we must deliver to earn a pilot or contract (e.g., SOC 2 Type II, three references from similar-size employers, platform test pass)?
• Who should own next steps on your side and what is the best way to keep them informed (weekly calls, shared dashboard, email summaries)? Options: Weekly calls, Shared project dashboard, Email summaries, Ad-hoc meetings
• If we could remove one remaining barrier right now, what would it be and why would that change everything for you?

• Solution Experience Preparation & Alignment
• Real-Time Eligibility Activation Simulation
• Parallel Service Run Kickoff & Execution
• Mock-Call Audit Workshop (Service Center Effectiveness)
• Consolidated Validation, Gap Analysis & Acceptance

• Customer delivers top 10 most-difficult call scripts and any recent escalated call recordings for calibration.
• Customer uploads production-complex plan design, sample employee records, and three escalated call recordings (72h before next session).
• Seller prepares scenario scripts, a test environment seeded with provided data, and timing/telemetry dashboards for measurement.
• Assign validation owners from both teams and circulate acceptance criteria and scoring rubrics.
• Objectives & Success Criteria for Parallel Run
• Agree and execute a parallel run that reproduces production activity sufficient to validate reconciliation and carrier feed reliability.
• Demonstrate monitoring that reliably measures SLA performance and exception resolution in near-real time.
• Capture gaps with owners and schedule remediations or retests if acceptance criteria are not met.
• Customer nominates operations and IT points of contact and grants access to the production-like data subset.
• Seller schedules the parallel run windows, configures routing, and provides the monitoring dashboard link.
• Both parties agree on the SLA reporting template and frequency for the remainder of the parallel run period.
• Rubric & Scoring Review
• Demonstrate service center can resolve complex plan questions and reach the customer's FCR target or provide a concrete improvement plan.
• Surface and document training or process gaps with owners and deadlines for remediation.
• Agree on a re-audit cadence and acceptance threshold for call quality.
• Brief Recap of Current State & Success Metrics
• Seller creates individualized coaching plans and updated SOPs for the identified gaps and schedules re-training.
• Schedule a follow-up mock-call re-audit once coaching is complete to validate improvement.
• Executive Recap: Current State -> Consequence -> Future State
• Provide a single consolidated decision (accept with handoff or conditionally accepted) to proceed to Deployment Enablement.
• Document all remaining gaps, assign owners, and set firm remediation deadlines before transition.
• Deliver an acceptance pack that ties each evidence artifact directly to the customer's defined success signals.
• Seller compiles an acceptance pack (activation logs, EDI test results, reconciliation reports, call scorecards, and SOC2 notes) and circulates to stakeholders.
• Customer executives provide formal acceptance or list conditions with owners for closure before Deployment Enablement.
• If conditional, both parties agree on remediation milestones and schedule a re-validation session prior to final handoff.
• Prove that real-time eligibility activation succeeds for the customer's complex plan designs within the agreed time window.
• Demonstrate the automated remediation path for carrier rejections and quantify reduction in manual remediations.
• Obtain customer confirmation that the observed outcomes map to their definition of 'better' (future state).
• Customer supplies 5–10 test employee records representing edge-case enrollments prior to the run.
• Seller produces a time-stamped activation log for each scenario and a short report mapping results to success metrics.
• If any scenario fails acceptance, owner to produce immediate remediation plan with ETA for retest.
• Introductions & Meeting Objectives
• Customer and seller sign off a single-sentence current state describing the exact failure and who it affects.
• Agree and document the quantified consequence(s) that make the problem urgent.
• Define and commit to 2–3 measurable future-state success signals to be proven during the experience.
• Confirm all pre-work artifacts and assign owners for simulations and validations.
• Run Mock-Call Scenarios (Live or Recorded)
• Parallel Run Design: Scope, Window, and Traffic
• Crystal-clear Current State (Diagnosis)
• Evidence Review: Simulation & Parallel Run Artifacts
• Scenario 1: Single Enrollment Activation (Core Case)
• Scorecard Review & Root Cause Analysis
• Live Execution: Sample Transaction Flow
• Service Center Evidence: Mock-Call Scorecards
• Explicit Consequence Statement
• Scenario 2: Complex Dependent / Plan Rule Edge Case
• Define Future-State Outcomes
• Gap Analysis & Risk Assessment
• Reconciliation & Exception Handling Demo
• Immediate Coaching & Process Adjustment Plan
• Bulk/High-Throughput Scenario
• Monitoring, Metrics & Reporting Plan
• Acceptance Checklist & Go/No-Go Decision
• Error Handling & Remediation Flow
• Artifact & Scenario Confirmation
• Validation & Re-Audit Plan
• Run Retrospective & Next Steps
• Logistics, Roles & Validation Rules
• Next Steps & Handoff to Deployment Group
• Validation Checkpoint & Customer Confirmation

• Migrate Benefits and Enrollment Data
• Configure Platform for Complex Plan Designs
• Establish and Maintain Carrier EDI Feeds
• Deliver Real-Time Eligibility Confirmation
• Operate Participant Service Center (Phone/Chat/Email)
• Reconcile Eligibility Discrepancies with Carriers
• Administer COBRA Notices and Processing
• Prepare and File ACA Reporting
• Reconcile Carrier Invoices and Billing
• Run Parallel Administration with Internal Team
• Deliver Monthly SLA Performance Exports
• Maintain SOC 2 Controls and Compliance Package

Migrate Benefits and Enrollment Data

• Do you require a full historical data migration or only current active enrollment and benefit elections? Options: Full historical (all prior years), Current and prior year only, Current active enrollments only, Other (explain)
• Which source systems contain your benefits and enrollment data? Options: HRIS (e.g., Workday, Oracle), Legacy benefits system, Broker/consultant exports, Carrier reports, Custom/Other
• What file formats and integration methods are available for migration (select all that apply)? Options: CSV/Excel exports, SFTP batch files, API/JSON, Database extract (SQL), Manual entry by client, Other
• Approximately how many unique covered lives and dependent records need to be migrated? Options: Less than 2,000, 2,000 - 10,000, 10,000 - 50,000, 50,000 - 100,000, More than 100,000
• Are there known data quality issues that require cleansing (e.g., duplicate SSNs, mismatched hire dates, inconsistent plan codes)? Options: Yes, No
• Who will own field mapping and reconciliation decisions during migration? Options: Client HR/Benefits team, Outsourcer implementation team, Broker/consultant, Third-party data vendor, Shared ownership
• Describe any non-standard or custom attributes that must be preserved (e.g., union codes, legacy benefit flags, custom eligibility tags).

Configure Platform for Complex Plan Designs

• How many distinct plan designs (medical, dental, vision, HSA, FSA, life, disability, voluntary) must be configured? Options: 1-5, 6-10, 11-20, 20+
• Do any plans have custom eligibility rules (hourly vs salaried, bargaining units, variable waiting periods)? Options: Yes, No
• Which of the following plan elements require configuration (select all that apply)? Options: Tiered coverage (EE/EE+1/Family), Dependent age rules, Class-based eligibility, Mid-year change rules, Retroactive effective dates, Elections with payroll deductions/pretax
• Are there employer-specific enrollment events (e.g., open enrollment windows, special enrollment periods, life events) with non-standard timelines? Options: Standard OE/SEP, Multiple OE windows by division, Continuous enrollment, Other
• Who will approve final plan configuration and test cases? Options: Client Benefits Lead, Client Compensation/HRBP, Broker/Consultant, Outsourcer Technical Lead, Other
• What acceptance tests must be passed for configuration signoff (examples: enrollment flow for most complex employee, premium calculation validation, dependent eligibility rules)?
• List any custom calculation rules or integrations required (e.g., HSA employer contribution schedules, payroll deduction offsets).

Establish and Maintain Carrier EDI Feeds

• How many carrier EDI feeds need to be established or reconfigured? Options: 1-2, 3-5, 6-10, 10+
• Which connectivity types are used by your carriers (select all that apply)? Options: 837/834 HIPAA EDI, Carrier proprietary API, SFTP batch, Manual carrier portal upload, Other
• Do carriers currently support real-time updates or only batch processing? Options: Real-time, Batch (daily), Batch (weekly), Mixed
• What are your required SLAs for carrier feed processing and error resolution? Options: Within 4 hours, Same business day, 48 hours, 5 business days, Custom (specify)
• Who is responsible for carrier testing and certificates—client, carrier, outsourcer, or broker? Options: Client, Carrier, Outsourcer, Broker/Consultant, Shared
• Describe current pain points with carrier feeds (examples: missing enrollments, mismatched IDs, delayed terminations).
• Are there required monthly/quarterly carrier reconciliation reports or audits we must produce? Options: Yes, No

Deliver Real-Time Eligibility Confirmation

• Is real-time eligibility confirmation a mandatory requirement or a desired enhancement? Options: Mandatory, Desired but optional, Not required
• For which carriers or plan types must eligibility be confirmed in real time?
• What is the expected confirmation window (e.g., within 4 hours of enrollment) for an enrollment to be considered 'real-time confirmed'? Options: Within 1 hour, Within 4 hours, Within 24 hours, Same business day, Custom
• What fallback process should be used when real-time confirmation is unavailable (e.g., parallel batch feed, provisional coverage flags)? Options: Use batch confirmation, Provisional coverage with manual follow-up, Escalate to carrier support, Other (describe)
• What acceptance criteria or test cases should be used to validate real-time eligibility functionality?
• Are there regulatory or contractual constraints affecting real-time confirmations (e.g., carrier restrictions, union agreements)? Options: Yes, No

Operate Participant Service Center (Phone/Chat/Email)

• Which channels should the participant service center support at launch? Options: Phone, Email, Chat (web), SMS, Portal messaging
• What are your target SLA metrics for the service center (first-call resolution, response times, abandon rate)? Options: 95% first-call resolution, 90% FCR, Average speed to answer <60s, Custom (specify)
• What language support and extended hours (time zones) are required? Options: English only, Bilingual (specify), 24/7 support, Business hours with extended OE hours, Other
• What expected monthly and peak call/chat/email volumes should staffing plan for? Options: Less than 1,000 interactions/month, 1,000-5,000, 5,000-20,000, 20,000+
• Will the client require mock-call audits and scorecards for acceptance testing of the service center? Options: Yes (number of scenarios to be defined), No
• Who owns escalation to client HR for unresolved participant issues? Options: Client HR, Broker/Consultant, Shared, Outsourcer
• Describe any specialized knowledge or scripts the service center agents must have (e.g., ERISA, COBRA, union rules, complex plan logic).

Reconcile Eligibility Discrepancies with Carriers

• What is the current monthly rate of eligibility discrepancies requiring reconciliation? Options: Less than 1%, 1-3%, 3-7%, 7%+
• What SLA do you require for discrepancy resolution with carriers? Options: 5 business days, Custom, Within 24 hours, 48-72 hours
• Should reconciliation be automated, manual, or a hybrid process? Options: Automated where possible, Manual reconciliation only, Hybrid (automated reconciliation + manual review)
• Who will own disputes with carriers (initiating appeals, providing evidence, negotiating corrections)? Options: Outsourcer, Client, Broker/Consultant, Shared
• What evidence and audit trail do you require for reconciled items (e.g., time-stamped tickets, carrier confirmations)? Options: Carrier EDI ack/log, Email confirmations, Ticketed audit log, Other
• Are retroactive adjustments common and how should they be handled for coverage and premium? Options: Yes — require credits/refunds, Occasional — case-by-case, No — not expected
• Provide examples of the most complex discrepancy scenarios we should plan for.

Administer COBRA Notices and Processing

• Does the client require state-specific COBRA/mini-COBRA administration in addition to federal COBRA? Options: Federal only, Federal + select states (specify), Full state-by-state coverage required
• Do you require electronic delivery of notices, physical mail, or both? Options: Electronic delivery, Physical mail, Both
• What typical monthly COBRA caseload should we plan for (new events and active participants)? Options: Less than 50 events, 50-200, 200-1,000, 1,000+
• Who is responsible for premium collection and invoicing for COBRA participants? Options: Outsourcer, Client, Third-party COBRA vendor, Shared
• Which acceptance tests should be executed for COBRA processing (notice timing, enrollment acceptance, premium billing)?
• Are there union or collective bargaining agreements that alter COBRA timelines or notices? Options: Yes, No, Unsure
• Describe any special reporting or audit requirements for COBRA administration.

Prepare and File ACA Reporting

• Which ACA filings are required (e.g., Forms 1094-C/1095-C, state-level filings)? Options: 1094-C/1095-C federal, State reporting required, Forms not required (non-applicable), Other
• Do you require assistance generating employee forms and distributing them electronically or by mail? Options: Electronic distribution, Physical mail, Both, Not required
• What is your expected timeline and who owns year-end reconciliation for ACA data? Options: Client owns, Outsourcer owns, Broker assists, Shared
• Do you anticipate a need for corrected filings and what is your tolerance for filing corrections? Options: Low tolerance — must be accurate, Some corrections acceptable, Expect corrections yearly
• Which payroll and HR data sources must be reconciled to produce ACA reports? Options: Payroll system, HRIS, Time and attendance, Other
• What acceptance criteria should be used to consider ACA reporting complete and auditable?
• Describe any multi-state or multi-entity complexities that affect ACA filing.

Reconcile Carrier Invoices and Billing

• Do carriers send monthly invoices that require reconciliation against enrollment and premium files? Options: Yes, No
• What invoice formats and frequencies are used by carriers? Options: Monthly PDF, EDI invoice, SFTP CSV, Portal only, Other
• Who is responsible for premium payment processing and remittance? Options: Client, Outsourcer, Third-party billing vendor, Shared
• What SLA is required for researching and resolving premium invoice discrepancies? Options: Within 5 business days, Within 10 business days, End of month reconciliation, Custom
• Do you require GL-level billing detail and export to your financial systems? Options: Yes — GL-detail required, Summary invoicing only, Optional

• Non-Disclosure Agreement (NDA)
• Master Services Agreement (MSA)
• Statement of Work (SOW)
• Commercial Terms & Fee Schedule
• Service Level Agreement (SLA) & Metrics
• Data Processing Agreement (DPA)
• SOC 2 & Security Evidence Package
• Reference Check Pack
• Acceptance & Go/No‑Go Criteria
• Transition & Knowledge Transfer Plan
• Carrier Connectivity & Third‑Party Responsibilities
• Change Order & Scope Amendment Process
• Insurance, Indemnity & Liability Certificates
• Payment Authorization & Purchase Order
• Exit, Data Portability & Escrow Terms

• Success Metrics Review
• Lessons Learned / Deployment Retrospective
• Operational Governance & Escalation Cadence
• Continuous Improvement & Enhancement Prioritization
• Customer Satisfaction, Mock-Call Audit & Reference Review

• Agree on funding/ resource commitments or change-order processes for high-impact items.
• Schedule a targeted training session for service center agents on the top 3 complex plan designs that caused issues.
• Governance Charter Review
• Create and approve a governance charter and meeting cadence that balances oversight with speed of decision.
• Agree on an escalation matrix that limits executive exposure and clarifies when board-level notice is required.
• Stand up a single shared collaboration channel and ticketing triage rules for all operational issues and enhancements.
• Publish the approved governance charter and RACI to the shared workspace and notify stakeholders.
• Configure the shared channel and integrate ticketing/alerts; create templates for incident reports and enhancement requests.
• Schedule recurring governance and tactical meetings with calendar invites and ownership of recurring agendas.
• Backlog Review
• Produce a prioritized 90-day enhancement roadmap with owners and measurable success criteria.
• Define pilot acceptance tests that directly prove future-state outcomes and risk reduction.
• Welcome & Objectives
• Publish the prioritized roadmap with owners, milestones, and pilot criteria into the governance backlog.
• Prepare cost estimates and resource plans for top three enhancements for CFO review.
• Schedule pilot start dates and draft acceptance test scripts tied to success signals.
• Satisfaction Metrics Overview
• Confirm overall user satisfaction and close any outstanding service quality gaps identified by audits.
• Obtain permission to use up to three comparables as references and agree on reference content scope.
• Assign corrective actions for service deficiencies and set deadlines for measurable improvement.
• Circulate mock-call audit details and required training plans to service center management.
• Collect written reference permissions and prepare reference packets (SLA evidence, ROI summary) for prospect use.
• Launch targeted remediation training and report improvements to the governance forum at the next cadence.
• Validate whether each success signal has been met and record formal acceptance or remediation triggers.
• Agree on financial reconciliation (remediation-cost accounting) and confirm cost-to-savings model assumptions.
• Assign owners and deadlines for remediation actions or confirm closeout if accepted.
• Deliver a signed acceptance or exception log capturing which success signals passed/failed and agreed remediation timelines.
• Provide detailed source reports (raw EDI test logs, call center scorecards, remediation invoices) within 3 business days.
• Update the shared performance dashboard to reflect agreed final metrics and version control.
• Retrospective Framing
• Capture a prioritized list of 6–10 concrete improvements with owners and deadlines.
• Identify systemic root causes that could recreate the initial failure modes and define prevention controls.
• Commit to updates of runbooks, training materials, and knowledge-transfer checkpoints.
• Produce a 'Lessons Learned' report with prioritized recommendations and circulate to governance stakeholders.
• Update operational runbooks and onboarding checklists to include new controls and publish to the shared channel.
• Mock-Call Audit Results
• Impact vs Effort Scoring
• Timeline & Incident Review
• Restate Success Signals
• RACI & Roles
• Pilot & Rollout Criteria
• Performance Dashboard Walkthrough
• Escalation Matrix
• What Went Well
• Reference Candidate Review
• Financial & Risk Consequence Review
• Collaboration Channel & Ticketing
• Funding & Resource Discussion
• Remediation for Low Satisfaction
• What Should Change
• Governance Schedule & KPI Cadence
• Gap Root-Cause Summary
• Action Prioritization
• Roadmap Agree & Owners
• Marketing & Case Study Next Steps
• Close & Documentation Plan
• Decision & Next Steps