Opening: Tell Us About Your Current Moment

• What immediate event or outcome prompted you to explore compensation change today? Options: Recent resignations of key people, Board request, Pay equity audit finding, Market competitiveness loss, New business strategy or M&A, Proactive alignment effort, Other
• Who on your team is most accountable for moving this forward day-to-day? Options: VP/Head of Total Rewards, CHRO, Compensation Manager, HRBP Lead, CFO/Finance representative, External consultant, Other
• How urgent is the timeline for decisions or changes? Options: Immediate (weeks), Near-term (1–3 months), Quarterly (3–6 months), Longer-term (6–12 months), Undetermined
• What would a successful first 90 days look like from your perspective?
• What internal attempts have you already made to address this, and what stopped them from delivering the outcome you wanted?

Who Really Holds the Keys?

• If you had to bet who ultimately approves a material compensation change, who would you be wrong to ignore? Options: Board compensation committee, CFO, CEO, CHRO, Compensation committee advisor, Major investor/PE sponsor, Other
• How do those stakeholders typically define a defensible recommendation—what evidence or language convinces them? Options: Benchmark data aligned to peers, Cost modeling and ROI, Pay equity analysis, Legal/compliance clearance, Scenario testing and sensitivity analysis, Stakeholder endorsements
• What has been the biggest source of friction when those parties reviewed past changes? Options: Insufficient data, Unexpected cost impact, Lack of governance/owner, Communication risks, Equity or legal concerns, Timing/conflicts with payroll
• Which decision-makers are most motivated by people retention, versus cost control, versus proxy/board defensibility? Options: Retention-focused, Cost-control-focused, Defensibility/proxy-focused, Combination, Undetermined
• Tell us about a recent approval that failed or stalled—who pushed back and why?

Where Pay Is Actually Breaking (Not Where You Think)

• Which parts of your pay system do you suspect are quietly costing you people or exposing you to risk? Options: Base pay ranges, Incentives / variable pay, Equity grants, Sales compensation, Job leveling inconsistencies, Geographic differentials, Other
• What measurable signals have you seen that point to failure—turnover hotspots, offer declines, pay complaints, or equity gaps? Options: Voluntary turnover spikes, Offer decline rates, Internal compression reports, EEO/pay equity flags, Exit interview themes, Manager escalation frequency
• Where does your job architecture break down—are titles, levels, or families inconsistent across functions? Options: Consistent across org, Some inconsistencies by function, Major inconsistencies / legacy systems, We don't have a formal job architecture
• Which roles do you believe are most out of market and why (examples, markets, or competitors)?
• Describe a recent situation where pay design produced an unintended behavior (e.g., quota chasing, internal mobility freeze). What happened and what did it cost?

What Would a Board-Ready Answer Need to Prove?

• What single proof-point would make your board say 'this is defensible' and greenlight the change? Options: Market benchmarking to a selected peer set, Modeled cost impact and ROI, Pay equity remediation plan, Legal sign-off and documentation, Stakeholder endorsement package
• Which metrics will satisfy governance—retention, gender/race pay gaps, comp-to-market, or total cost of ownership? Options: Retention impact, Pay equity metrics, Percentile vs market, Total comp budget impact, Executive proxy disclosure readiness
• How important is auditable methodology and traceability (e.g., source data, weighting, statistical notes) for your reviewers? Options: Critical—must be auditable, Important but flexible, Nice to have, Not a priority
• What historical evidence (past analyses, benchmarks, board minutes) would you want attached to a recommendation?
• If the board asks for worst-case and best-case scenarios, which risks do you most want modeled? Options: Budget overrun, Employee retention failure, Proxy advisor negative opinion, Regulatory or legal exposure, Operational disruption

Imagining Outcomes: Numbers + Narrative

• If compensation changes not only moved pay but actually changed behavior, what three outcomes would you prioritize?
• Which of these outcomes should be measured quantitatively versus qualitatively in the first year? Options: Retention rates, Offer acceptance, Performance distribution, Pay equity improvements, Employee sentiment
• What is an acceptable incremental cost-to-market to achieve the desired outcomes (as a % of payroll or dollar range)? Options: 0–0.5% of payroll, 0.5–1% of payroll, 1–2% of payroll, 2%+ of payroll, We haven't defined it
• How quickly would you expect to see signal that changes are working (30/60/90 days, 6 months, 12 months)? Options: 30–90 days, 3–6 months, 6–12 months, 12+ months
• Who needs to feel the narrative is credible—employees, managers, investors, or the board—and why? Options: Employees, Managers, Investors/owners, Board/comp committee, Multiple parties

Data & Systems Reality Check

• How confident are you that your HRIS and payroll can produce the precise outputs a redesigned structure requires? Options: Very confident, Somewhat confident, Not confident, Don't know
• Which systems will we need to touch or extract from (HRIS, payroll, ATS, equity management), and who owns them? Options: Workday, SAP SuccessFactors, UKG/PeopleSoft, ADP/payroll, Equity platform (e.g., Carta), Other / custom
• Are there known data quality issues—missing grade/level, incorrect hire dates, or inconsistent job codes—that have blocked past projects? Options: Yes—major issues, Some issues but manageable, No major issues, Unsure
• Can you share a sample extract (anonymized) with incumbents, comp elements, grades, and hire dates within the engagement timeline? Options: Yes—we can provide immediately, Yes—but will take time, No—we cannot share extracts, Unsure / need to check
• Who would be the owners for remediation tasks if we surfaced data or HRIS mapping gaps? Options: Comp/Total Rewards team, HRIS/People Ops, Payroll, Finance, External vendor, Other

Implementation & Governance: Who Will Run This?

• If you were handed a detailed implementation plan today, what would realistically stop it from being executed? Options: Budget constraints, Lack of owners, Competing priorities, Payroll system limits, Board approval delays, Union/works council issues
• What internal governance cadence do you prefer for review and approvals (weekly working group, biweekly steering committee, monthly exec updates)? Options: Weekly working group, Biweekly steering committee, Monthly executive update, Ad hoc as needed, Other
• Who will be responsible for sign-off at each gate (design, pre-deployment, payroll validation, go-live)? Please list roles.
• What acceptance criteria must be met before you’ll consider a change deployable (e.g., payroll parity, equity remediation thresholds, manager training complete)?
• How do you prefer to surface and resolve issues during cutover—escalation matrix, war room, daily standups? Options: Escalation matrix, War room during cutover, Daily standups, Dedicated Slack/channel, Other

Commercial & Success Commitments

• What minimum commercial or governance commitment would make this engagement worth the effort for your leadership? Options: Clear ROI within 12 months, Board-ready deliverables, A closed remediation plan for equity issues, Operationalized outputs for HRIS/payroll, Other
• What budget or procurement constraints should we be aware of before proposing an approach? Options: Fixed budget, Range available with approval, Procurement cycle timeline, No formal constraints, Unsure
• How do you expect us to partner—advisory + deliverable handoff, or embedded with your team through deployment? Options: Advisory + deliverables, Embedded partnership, Train-the-trainer model, Mixed approach
• Which success metrics would trigger ongoing support or a renewal of services from your side? Options: Retention improvement, Achieved pay equity thresholds, Board acceptance, Payroll/HRIS stability post-change, Employee sentiment improvement
• Who needs to be on the invoice/statement of work and who signs it for your organization?

Final Check: Risks You're Not Talking About

• What’s the uncomfortable or politically risky aspect of this project that people avoid saying out loud?
• Are there legacy commitments—verbal promises, retention bonuses, or localized agreements—that limit how we can redesign pay? Options: Yes—multiple commitments, Some localized agreements, No significant legacy commitments, Unsure
• Do you anticipate any external stakeholder reactions (investors, proxy advisors, regulators) that should shape how we position recommendations? Options: Investor scrutiny, Proxy advisor sensitivity, Regulatory/regional compliance, Minimal external scrutiny, Unsure
• How do employees typically react to pay changes—anger, confusion, appreciation, indifference—and how have you managed that in the past? Options: Anger/resentment, Confusion/questions, Generally positive, Mixed reactions, We haven't communicated changes well
• What would you most want us to include in the communication kit to head off political risk? Options: Manager talking points, Board memo and appendices, Employee FAQ, Detailed modeling appendix, Training modules

Tell Me About Your World — a quick scene-setter

• To get us started, which statement best describes where your compensation program sits today? Options: No formal structures (manager discretion), Documented pay structures but outdated, Recently redesigned and rolling out, Multiple legacy programs from M&A, We run annual market adjustments only
• Which pay components are active for most employees at your company right now? Options: Base salary, Annual bonus / STI, Long-term incentives / equity, Commission / sales incentives, Sign-on / retention bonuses, Special allowances (location, shift, on-call), Other
• Roughly how many employees and countries does this program need to cover (list headcount and geo scope)?
• Who is your primary internal sponsor for compensation change (role/title) and how invested are they emotionally in getting this right? Options: CHRO, VP/Head of Total Rewards, CFO, CEO, Compensation Committee Chair, Other
• When you think about the last time compensation caused a big headache, what was the single most painful outcome? Options: High voluntary turnover in a function, Board or proxy scrutiny, Pay equity audit failure, Candidate offer losses, Payroll errors / overpayments, Other

Are You Confident Your Data Tells the Truth?

• If I told you someone could prove your pay decisions are defensible in front of the board, would your current data support that claim? Options: Yes — we have auditable evidence, Mostly — with some gaps, Not really — data quality is an issue, No idea
• What are the primary sources you rely on when making pay decisions (select all that apply)? Options: Payroll system, HRIS / employee records, Proprietary benchmark data, External salary surveys, Finance/GL data, Recruiting offer data, Legacy spreadsheets, Other
• How current are the data feeds you depend on (last payroll extract, survey refresh, comp history)? Options: Realtime / daily, Monthly, Quarterly, Annual, Irregular / ad hoc
• Where do you feel data accuracy breaks down most often (job titles, pay element mapping, manager-entered fields, global currency conversions, other)?
• Tell a short example of a time data led you to the wrong conclusion—what happened and what did you learn?

Where Compensation Is Burning You

• Which compensation failure keeps you up at night — the one outcome you fear repeating? Options: Losing high performers to competitors, A discriminatory pay gap finding, Uncontrolled salary inflation, Executive pay not defensible to proxy advisors, Payroll compliance penalties, Other
• Which roles or functions are you losing most frequently, and what reason do departing employees most commonly give? Options: Sales — commission/pay, Engineering — market pay, Product — equity competitiveness, Operations — pay banding issues, Leadership — total package, Other
• What measurable signals have you tracked that show pain (e.g., voluntary turnover %, offer acceptance delta vs market, internal equity variance)? Please list the top 2–3 metrics and recent values.
• How long have these failure patterns been present, and have they been getting better, worse, or stayed the same? Options: Less than 6 months, 6–12 months, 1–2 years, More than 2 years
• Has leadership tried to fix this before? If so, what was attempted and why didn't it stick?

Who Holds the Keys — and What Would Happen If They Let Go?

• Who currently has final decision rights over pay structure changes and who must sign off for the board to feel comfortable? Options: CHRO, CFO, CEO, Compensation Committee/Board, Head of Total Rewards, Legal/Compliance, Other
• When you need to change pay for a population, what is the typical approval pathway and how long does it take from proposal to execution? Options: Days, Weeks, 1–3 months, 3–6 months, 6+ months
• What evidence persuades your CFO or board — total cost modeling, benchmarking to peers, pay equity stats, scenario impact on retention, or something else? Options: Total cost modeling, Market benchmarking, Pay equity analysis, Retention/attrition modeling, Scenario-based outcomes, Other
• Have you experienced stakeholder pushback driven by perception rather than data? If yes, who raised it and what convinced them eventually (if anything)?
• If a recommended change required a material budget increase or redistribution of pay, what internal trade-offs would you accept and which are non-negotiable?

When Pay Decisions Break (and Who Notices)

• What parts of your HRIS/payroll architecture feel most brittle when you try to change pay rules or ranges? Options: Job/grade mapping, Currency conversions, Incentive calculation engines, Retroactive pay processing, Third‑party payroll integrations, Other
• Which HRIS/payroll/vendor systems do you rely on today (select all that apply)? Options: Workday, SAP SuccessFactors, Oracle HCM, ADP, UKG/Ultimate, Ceridian, Homegrown / custom, Multiple / hybrid, Other
• Describe a recent implementation or change that failed or created significant remediation work—what was the root cause?
• How tightly coupled are your compensation decisions to payroll cycles and finance close (i.e., how disruptive is a mid‑cycle change)? Options: Very tightly coupled, Somewhat coupled, Loosely coupled, Not sure
• What internal resources or roles own mapping, extract transforms, and validation for a pay deployment (names/titles and availability)?

If We Fixed One Thing, What Changes the Whole Story?

• If you could wave a wand and fix one compensation problem that would change momentum across the company, what would it be?
• Which outcomes would signal success for you in the first 12 months (select up to three)? Options: Reduced voluntary turnover, Improved pay equity metrics, Lower offer rejection rate, Defensible board approvals, Reduced payroll errors, Predictable comp budgeting
• What timeline do you expect for seeing meaningful impact from a redesigned structure (immediate, 3–6 months, 6–12 months, longer)? Options: Immediate (0–3 months), 3–6 months, 6–12 months, 12+ months
• How willing are you to trade short-term budget neutrality for long-term competitiveness—what is your tolerance on cost delta? Options: Prefer budget-neutral, Small increase acceptable (<5% comp budget), Moderate increase acceptable (5–10%), Open if ROI clear
• Who in your organization will judge whether the change ‘worked’ and what evidence will they ask to see?

Getting Practical: Non‑Negotiables, Timelines, and Data Prep

• What are the hard non‑negotiables we must design around (e.g., union agreements, regulatory caps, industry pay bands, board directives)?
• What specific data extracts can you commit to delivering and when (e.g., current payroll file, employee master, historical promotions, offer data)? Options: Payroll extract, Employee master / HRIS, Offer acceptance history, Historical compensation adjustments, Performance ratings/history, Equity grant history, We haven’t prepared these
• Who will be the day‑to‑day owner for remediation and HRIS mapping if we identify gaps, and what percent of their time can they allocate?
• What timeline and gating do you have for procurement, CFO/board review, and deployment (ideal dates or windows)?
• On a scale from 1–5, how deployment‑ready do you feel: 1 = need foundational clean‑up, 5 = ready to deploy with final approvals? Options: 1, 2, 3, 4, 5

Quick Check — Where Are We Right Now?

• Which phase best describes your current readiness for implementing pay structure and incentive changes? Options: We’ve only agreed in principle, Scoping complete, awaiting data, Data prep underway, Implementation planning in progress, Ready to cutover
• Who are the active sponsors and decision-makers for this project? Options: CHRO/Head of HR, CFO/Head of Finance, Comp Committee/Board Chair, Head of Payroll/HRIS, General Counsel, Other
• What is your target timeline for the first payroll reflecting these changes? Options: Next payroll (within 2 weeks), 1–2 months, 2–4 months, 4–6 months, Longer / TBD
• What keeps you up at night about this deployment? Options: Payroll errors/overpayments, Equity remediation risks, Budget blowouts, CFO/board rejection, Employee backlash, Data integrity issues, Other
• Briefly describe one recent payroll or comp implementation that went well — what made it successful?

If Implementation Fails, Who Pays the Price?

• Imagine the rollout generates significant pay calculation exceptions — whose credibility or budget would be most exposed? Options: CHRO/Total Rewards, CFO/Finance, Payroll/HRIS team, Compensation Committee/Board, Legal/Compliance, Other
• How have past compensation changes affected executive or board confidence in HR recommendations? Options: Increased confidence, No change, Decreased confidence, Not applicable/no prior changes
• What are the worst-case downstream consequences you’re most concerned about (e.g., overpayments, legal exposure, employee attrition)?
• Who would lead the public or board-facing explanation if adjustments or remediation were required after deployment? Options: CHRO, CFO, Head of Legal, Comp Committee Chair, External advisor/consultant, Other
• If we uncovered a material error during validation, how quickly must it be resolved to avoid material stakeholder impact? Options: Within 24 hours, 48–72 hours, Within two weeks, End of quarter, Depends on severity

Can Your Data Actually Run the Playbook?

• Do you have an authoritative list of data sources for compensation (HRIS, payroll, performance, equity, benefits)? Select all that apply. Options: Core HRIS, Payroll system, Performance management, Equity administration, Benefits platform, Time & attendance, Other
• How complete and current is the compensation data across those sources? Options: Up-to-date and complete, Mostly complete with gaps, Significant gaps, Unknown
• Which key fields can you reliably extract today (job code, level, base pay, bonuses, equity grants, hire date, manager, cost center)? Options: Job code, Job title, Level/grade, Base salary, Bonus target/plan, Equity holdings/grants, Hire date, Manager, Cost center/BU, Other
• Are there legal or privacy constraints that will affect the extracts (e.g., masking, cross-border data transfer restrictions)? Options: No constraints, Some masking required, Cross-border restrictions, Union/collective bargaining limits, We need legal review, Other
• Who owns each data source and can sign off on a production extract? Options: HRIS owner, Payroll owner, IT/data team, Total Rewards, Finance, Legal, Other
• Describe any recent data surprises (e.g., stale job codes, duplicated records, missing pay elements) and how long it took to remediate.

HRIS vs. Reality — What Your Systems Won’t Admit

• Which HRIS and payroll platforms are in scope for this deployment? Options: Workday, SAP SuccessFactors, Oracle HCM, UKG/UltiPro, ADP, Ceridian, Custom/on-prem, Other
• What customizations or local payroll rules exist that could block a generic pay range or incentive calculation? Options: Country-specific tax rules, Custom pay components, Legacy interfaces, Manual overrides, Union/collective agreements, None/standard
• How easily can your HRIS accept new pay range metadata or incentive term sheets (config change, API, manual upload)? Options: Configurable via UI, Requires IT change request, API-based integration, Manual spreadsheet uploads, Not sure
• Describe one known limitation of your HRIS/payroll that has forced a workaround in the past (e.g., cannot store range midpoints, manual override required).
• How much lead time does your payroll vendor/partner require for configuration changes before a pay cycle? Options: <1 week, 1–2 weeks, 2–4 weeks, 4+ weeks, Varies by change

Who Will Be Responsible When the Numbers Don't Match?

• If a validation discrepancy is found, who is accountable for remediation and resolution? Options: Payroll team, HRIS team, Total Rewards/Comp, Finance, Legal, Third-party vendor, Other
• How are acceptance criteria and sign-off defined today for compensation changes (sample: tolerance thresholds, reconciliation counts, approval gate owners)? Options: Formal documented criteria, Informal agreed thresholds, Ad-hoc sign-off, No criteria defined
• Who has final sign-off authority to move to production for pay changes and remediation actions? Options: CHRO, CFO, Head of Payroll, Comp Committee/Board, Legal, Other
• Do you maintain an issues register or remediation tracker today, and who updates it? Options: Yes — centralized tracker, Yes — distributed trackers, No formal register, Planning to create one
• When remediation involves headcount or budget decisions, who approves the funding or headcount changes? Options: Finance, CHRO/People, Business unit leader, CFO, Other

Can Compliance Hold a Mirror to This Plan?

• Which compliance frameworks or laws are most likely to affect this deployment (e.g., pay equity laws, tax reporting, SEC disclosures, union rules)? Options: Federal pay equity requirements, State/country pay equity laws, Tax reporting constraints, SEC/proxy disclosure, Union/works council rules, Other
• Have legal and compliance teams already reviewed the proposed changes, and if so, what was their top concern? Options: Yes — no major concerns, Yes — minor concerns to remediate, Yes — material concerns, Not yet reviewed
• What internal controls do you have around payroll changes (segregation of duties, audit logs, change approvals)? Options: Segregation of duties, Audit logging, Dual approvals, Change control board, Limited/paper trail, None
• When sensitive remediation is required (e.g., pay equity adjustments), how should communications be routed to protect confidentiality? Options: Direct manager disclosure, Private HR outreach, Group-wide announcement, Legal-reviewed messaging, Other
• Has the company faced any regulatory findings or audits related to compensation in the last 3 years? If yes, summarize impact. Options: No, Yes — minor findings, Yes — material findings, Unknown

Can Payroll Execute the Cutover Without a Reprise of Errors?

• Do you plan to run parallel payrolls/test payrolls prior to cutover? Options: Yes — full parallel runs, Yes — sample parallel runs, No — single dry run, No — direct cutover
• What percentage of the population must reconcile perfectly in validation before we accept production go-live? Options: 100%, 99–99.9%, 95–99%, 90–95%, Other
• Who will perform day-of payroll reconciliations and where will variance tolerances be documented? Options: Payroll operations, Finance reconciliations, HR/Total Rewards, Shared responsibility, Not yet defined
• If an error requires rollback, do you have the systems and approvals to revert changes within your payroll timeline? Options: Yes — full rollback capability, Partial rollback possible, No — rollback not feasible, Unsure
• Describe any blackout periods or payroll freeze windows that would prevent changes from being applied

How Will We Know It's Working — And Who Fixes What Next?

• Which success metrics do stakeholders want validated post-deployment (choose up to three)? Options: No. of payroll exceptions, Pay equity gaps closed, Retention improvement, Cost-to-market alignment, Manager adoption rate, Employee satisfaction
• What level of evidence will satisfy the CFO and Compensation Committee that the deployment met objectives (reconciliations, sample audits, third-party attestation)? Options: Detailed reconciliations, Executive summary + samples, Third-party attestation, Board-ready memo, Other
• Who will own ongoing monitoring and remediation after go-live, and how frequently should we review performance? Options: Total Rewards, Payroll, Finance, People Analytics, Shared governance, Other
• What escalation path should we use for post-live issues that risk material impact? Options: Immediate CHRO/CFO notification, Issue triage group, Legal escalation, Weekly governance meeting, Other
• If we propose a 90-day stabilization window with defined checkpoints, what concerns or constraints might prevent that from working?

What Would Make Your Stakeholders Sleep Easier?

• Which stakeholder anxieties are highest and most likely to block approval (board optics, financial impact, employee morale, audit risk)? Options: Board optics, Financial impact, Employee morale, Audit/regulatory risk, Operational disruption, Other
• How transparent do you want reporting to be during implementation (detailed weekly dashboards vs. high-level executive updates)? Options: Daily operational dashboards, Weekly detailed reports, Biweekly executive summary, Milestone-only updates
• What format best reassures the board or comp committee (live demos, sample payroll outputs, third-party validation, written memos)? Options: Live demo/walkthrough, Sample payroll outputs, Third-party validation, Board memo + Q&A, Other
• Which communications should be pre-approved before any employee outreach (press/legal, HR, leadership)? Options: Legal-approved messaging, HR drafted templates, Leadership talking points, No pre-approval required, Other
• What would be one small assurance we could deliver quickly to ease stakeholder nerves?

Commitments, Gaps, and Immediate Next Steps

• On a scale of 1–10, how ready are you to start detailed implementation work this week? Options: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10
• What are the top three artifacts or accesses we need from you in the next 7 days to avoid delays?
• Who should be invited to the technical kickoff and who needs executive briefing access (names/titles)?
• What single blocker, if unresolved, would prevent us from achieving your target deployment date?
• Which cadence do you prefer for governance during deployment (weekly ops, biweekly steering, monthly exec)? Options: Weekly operational meetings, Biweekly steering committee, Monthly executive reviews, As-needed
• Any final thoughts or hidden constraints we haven’t asked about that we should surface now?

A Quick Welcome — Who Are We Partnering With?

• What's your primary role in leading or sponsoring compensation work? Options: CHRO, Head of Total Rewards/Compensation, VP/Director HR Ops, CFO, Compensation Committee Chair, CEO, Other
• What best describes your organization right now? Options: High-growth / hiring rapidly, Stabilizing after layoffs, Post-merger / acquisition, Public company with proxy concerns, Non-profit / public sector, Other
• In one sentence, what outcome would make this work feel unquestionably worth doing for you?
• Which of these compensation challenges feels most pressing today? (pick up to 3) Options: Turnover to competitors, Pay equity findings, Incentive misalignment with strategy, Executive pay scrutiny, Poor internal compression, Global harmonization, HRIS/payroll implementation constraints
• What is your target decision/timing horizon for a board‑ready recommendation? Options: Within 30 days, 30–60 days, 60–90 days, 3–6 months, Longer / exploratory

If Your Compensation System Could Talk, What Would It Confess?

• Where are you most disappointed by how pay actually functions versus how you think it should?
• Which roles or populations are most likely to leave because of pay issues, and how long has this been a pattern?
• Can you describe a recent, concrete example where compensation decisions led to a loss, legal exposure, or major employee backlash?
• How have your leaders reacted when these problems surface—dismissal, stop‑gap raises, structural change attempts, or other? Options: One-off pay fixes, Formal redesign attempts, Avoidance / deferment, Ad hoc manager discretion, Legal counsel involvement
• How does this make you feel when you brief your CEO or board—defensive, uncertain, pressured, or something else? Options: Defensive, Uncertain, Pressured, Motivated to act, Other

When the Board Asks 'Why Now?' — Can You Answer Them?

• What specific event or trigger has created urgency (pick one)? Options: High-profile departure, Pay equity audit, Proxy advisor concern, Market benchmarking shows lag, Regulatory/union issue, Leadership mandate, Other
• Who must sign off on recommendations for this work to proceed to implementation (select all that apply)? Options: CEO, CFO, CHRO, Compensation Committee/Board, Legal/Compliance, Head of Payroll/HRIS
• What evidence or artifacts will convince the board/CFO this approach is defensible (e.g., statistical analysis, market percentiles, cost scenarios)? Options: Benchmark percentile rationale, Pay equity statistical report, Cost-to-market impact model, Implementation risk assessment, Compensation governance plan
• What is the non‑negotiable deadline (e.g., board meeting date) that shapes your timeline?
• If we needed to compress deliverables for an earlier board readout, what would you be willing to accept as a minimum viable deliverable? Options: Executive summary + high-level cost scenarios, Role-level benchmarking for key populations, Pay equity heatmap, Detailed pay ranges and acceptance criteria

Behind the Numbers — How Solid Is Your Data?

• Which HRIS / payroll systems currently hold your compensation master data? Options: Workday, SAP SuccessFactors, UKG/Ultimate Kronos, Oracle HCM, ADP, Custom / Homegrown, Multiple / Hybrid, Unsure
• Where do you have the biggest concerns about data quality—job titles, incumbents, pay components, or tenure? Options: Job titles/classification, Incumbent level accuracy, Variable pay history, Equity grants and vesting, Start/termination dates, Other
• How often have you needed to do manual remediation to reconcile payroll vs. intended pay (and how long does that usually take)? Options: Rarely, Quarterly, Monthly, Continuously / ongoing
• Which external benchmarking sources do you currently trust and why?
• Are there legal, union, or country‑specific constraints we should plan around during discovery? Options: Collective bargaining agreements, Local pay disclosure laws, Executive pay disclosure rules, Data privacy restrictions, Other / specify

What Would 'Defensible' Look Like at Your Company?

• When you hear 'board‑ready and defensible', what three things must be true?
• Which market percentile or positioning philosophy best matches your aspiration? Options: Median (50th), Competitive midpoint (55–65th), Lead the market (70th+), Role dependent / graded approach, Unsure
• What level of first‑year total compensation cost increase (if any) would you consider acceptable to achieve target outcomes? Options: No increase (reallocation only), Up to 1% of payroll, 1–3% of payroll, 3–6% of payroll, Unsure / scenario‑dependent
• How do you expect to balance equity remediation versus market competitiveness when they conflict? Options: Prioritize equity remediation, Prioritize market competitiveness, Phase remediation over time, Case-by-case with governance
• Who in your leadership team will defend recommendations that increase short‑term cost for long‑term benefit?

What Stops a Well‑Designed Plan from Becoming Reality?

• When past compensation changes failed, what specifically went wrong?
• Which implementation constraint worries you most: data, systems, change management, union/legal, or budget? Options: Data quality and readiness, HRIS/payroll mapping, Manager adoption/change management, Union or legal constraints, Budget / financial approval
• Who owns remediation and cutover in your organization, and how empowered are they to make fast decisions?
• How much timeline slippage have you historically experienced between decision and payroll cutover? Options: Minimal (weeks), Months, Many months / iterative
• If we propose phased implementation, what phase sequencing would be acceptable (e.g., pilot population first)? Options: Pilot key functions/levels, Regional rollout, Job family by job family, All at once

Show Me the Scenarios That Would Convince the CFO

• Which scenario types do you want us to model and contrast for the CFO? (select up to 4) Options: Base pay structure + ranges, Compression remediation, Short‑term incentive redesign, Equity modeling and dilution impact, Cost-to-market delta, Headcount-level impact
• What acceptance criteria must payroll outputs meet for you to sign off (e.g., per‑employee variance thresholds, reconciliation success)?
• Which sample roles should we prioritize for detailed modeling to make the case quickly?
• Do you need scenario outputs at the individual employee level, aggregate cost level, or both? Options: Individual employee level, Aggregate cost level, Both
• How will you evaluate tradeoffs between simplicity for payroll and nuance needed for fairness (e.g., banding vs. slotting)?

Who Will Make This Happen — And Will They?

• Who will be the day‑to‑day sponsor and the person accountable for implementation outcomes?
• Which stakeholders must be engaged during discovery and implementation (select all that apply)? Options: CFO/Finance, Compensation Committee/Board, Legal/Compliance, Payroll Operations, HRIS/Technology, People Managers/Business leaders
• How quickly can your payroll/HRIS team provide certified data extracts once we request them? Options: Within 1 week, 1–2 weeks, 2–4 weeks, Longer / need planning
• What internal governance cadence is realistic for sign‑offs—weekly, biweekly, monthly? Options: Weekly, Biweekly, Monthly, Ad hoc as needed
• If conflicts arise between department leaders, what's your escalation path to resolve them?

What Would Success Feel Like in 12 Months?

• Describe the top three measurable outcomes that would make you call this engagement a success a year from now.
• What specific retention, equity, or cost-to-market targets matter most (choose up to 3)? Options: Retention improvement %, Reduction in pay gaps by cohort, Target market percentile attainment, Reduction in reactive one-off pay increases, Improved manager satisfaction with pay tools
• How will you demonstrate ROI to finance or the board—qualitative stories, hard dollar savings, or risk reduction? Options: Hard dollar savings, Risk / legal exposure reduction, Retention and productivity improvements, Board-ready narrative with data
• Would you consider a living governance model with quarterly reviews as part of success, or do you prefer a static one‑time change? Options: Living governance with ongoing reviews, One-time redesign, Hybrid / time-limited governance
• Who should own continuous improvement after we exit—HR Total Rewards, People Ops, or a joint governance committee? Options: HR Total Rewards, People Ops, Finance/Payroll, Joint governance committee, Other

Next Steps — Making This Practical

• Which working model would you prefer for this engagement? Options: End-to-end advisory + implementation, Advisory + handoff to internal team, Deliverable-focused (e.g., ranges + models), Pilot-first then scale
• Are there commercial or procurement constraints (e.g., vendor approval, PO terms) we should know about up front? Options: Standard vendor onboarding, Requires legal review, Must fit within existing SOW, Other / specify
• What are the top three risks you want us to explicitly mitigate during discovery and design?
• How would you like us to communicate progress and decisions—weekly executive summary, shared workspace, or standing working sessions? Options: Weekly executive summary, Shared collaboration workspace, Standing working sessions, Ad hoc updates
• If we agreed on next steps today, what would a practical first deliverable look like and when can your team commit to kickoff?