Opening: Who's in the Room and Why?

• Who is sponsoring this capital allocation review and what’s the single most important outcome they want? Options: CFO, CEO, Board Chair, Finance Committee Chair, PE Partner / Sponsor, Family Office Principal, Other
• Who will present the recommendation to the board or LPs (name and role)?
• What is the firm deadline or next board/LP meeting date driving this work? Options: Next 2 weeks, 2–4 weeks, 1–3 months, 3–6 months, No firm deadline
• Which stakeholders must sign off before allocations change (select all that apply)? Options: Board, Finance Committee, CEO, CFO, Business Unit Heads, Investor/LP Consent, Advisory / External Counsel
• What would success look like for the sponsor at the end of this engagement (one-sentence answer)?

Are We Comfortable With How Decisions Get Made?

• If you had to bet, who actually holds the final decision power when allocations become political? Options: Board Chair, CEO, CFO, Largest Investor / LP, Finance Committee, Business Unit Heads, Other
• Tell us about a recent allocation decision that was driven more by politics than analysis—what happened and why?
• How clear are escalation paths when committees can’t reach agreement? Options: Clearly documented and followed, Informal but understood, Unclear / ad hoc, No escalation path
• Which investor or board priorities tend to override financial optimization? Options: Short-term EPS, Market share, Strategic control / governance, Conservative balance sheet, Speed of deployment, Founder preferences, Other
• Who on the governance side is most likely to veto an analytical recommendation, and why?

Numbers That Tell the Story (or Hide It)

• What part of your current allocation picture do you suspect is misleading the board the most? Options: Aggregate cash position, Internal hurdle rates, Historic allocation bias (buybacks / M&A), Liquidity runway assumptions, Projected synergies / deal economics, Other
• Please quantify historical allocation over the last 3 years (approx % to each): buybacks, dividends, M&A, capex, debt paydown, cash build.
• How are internal hurdle rates set today (process and owner)? Options: Central finance sets them, Business units propose, finance approves, Executive committee sets, No formal process / ad hoc
• When was the last time hurdle rates were recalibrated against market comps or WACC changes? Options: Within 6 months, 6–12 months, 1–2 years, Over 2 years / never
• Describe common failure modes where past allocation choices produced regret (specific examples encouraged).

What's Making the Assumptions Feel Unsafe?

• Which single assumption in your models, if wrong, would change the recommended allocation path overnight? Options: Revenue growth, Margin recovery, Multiple expansion / contraction, Realized synergies, Financing availability / cost, Exit timing / IPO window, Other
• How do you currently stress-test or run sensitivities against those key assumptions? Options: Basic sensitivity table, Full scenario suite, Ad hoc manual checks, Rarely / not systematic
• Have recent macro or sector moves materially invalidated assumptions you rely on? If so, which ones and how?
• Which scenarios do you wish you had modeled but haven’t—eg. forced liquidity event, capital markets shutdown, competitor M&A? Options: Liquidity shock, Multiple compression, Competition-driven price war, Large acquisition opportunity, Regulatory shock, Other
• Who on your team is responsible for keeping model assumptions current and challenged? Options: CFO, FP&A, Treasury, Head of Strategy, Business Unit CFOs, External advisor

Where Would the Board's Head Nod Come From?

• What single measurable outcome would make the board say 'approve' with confidence? Options: Target valuation achieved, Defined liquidity runway, Minimal dilution threshold, IRR / NPV threshold met, Strategic market position improved, Other
• Please define the specific targets for valuation, liquidity, and strategic outcomes (numbers or ranges preferred).
• Which time horizons matter most to the board for these targets? Options: This quarter, 12 months, 2–3 years, 3–5 years, Longer-term / strategic
• What monitoring metrics would reassure the board after a decision (examples: free cash flow, debt / EBITDA, ROIC, volatility limits)? Options: Free cash flow, Debt / EBITDA, ROIC, ROIC vs hurdle, Liquidity runway (months), Share count / dilution, Other
• What minimum evidence package does the board expect before sign-off (peer comps, sensitivity outputs, legal sign-offs, scenario overlays)? Options: Peer benchmarking, Full scenario models, Sensitivity tables, Executive summary slides, Legal / tax memos, Independent fairness / valuation opinion

Price vs Control vs Timing — Which Wins?

• When choices conflict, does the organization prioritize minimizing dilution, maximizing valuation, preserving optionality, or something else? Options: Minimize dilution, Maximize valuation, Preserve optionality / optionality value, Prioritize liquidity / conservative balance sheet, Speed to deploy capital
• Give a specific recent trade-off (price vs control vs timing) and explain how it was resolved—what guided the decision?
• Do you have firm thresholds for acceptable dilution or deal structures (select one)? Options: <5%, 5–15%, 15–30%, >30%, No formal thresholds
• How do financing constraints and covenant terms influence the timing of allocation decisions?
• Which external audiences (analysts, largest shareholders, lenders) matter most when weighing dilution vs. liquidity? Options: Sell-side analysts, Largest shareholders / blockholders, Lenders / banks, Private investors / LPs, Employees (option pool)

What Would Make Our Models Irrefutable to You?

• What would make you stop questioning model outputs and accept them as board-grade evidence? Options: Transparent assumptions and audit trail, Back-tested scenarios, Independent validation, Peer benchmarking, Clear governance and ownership
• Which inputs do you treat as sacred (i.e., cannot be adjusted without committee approval)? Options: Revenue growth, Discount rate / WACC, Exit multiple, Synergy realization schedule, Capex ramp, Other
• What format of model deliverable is most persuasive to your board—detailed workbook, executive scenario dashboard, or both? Options: Detailed workbook with audit trail, Executive dashboard + appendix, Interactive scenario tool, One-pager with key scenarios
• Who will be responsible internally for model validation, reproducibility checks, and maintaining a single source of truth? Options: CFO, FP&A, Treasury, Head of Strategy, External auditor / advisor, Other
• Are there regulatory, audit, or compliance constraints that limit how we present model assumptions or scenarios to investors or the board?

What Would Kill This Engagement Before We Get to the Board?

• What is the single organizational behavior that has derailed similar advisory engagements in the past? Options: Business unit resistance, Board overrides, Competing internal priorities, Data quality issues, Budget / fee objections, Other
• Have business unit leaders resisted centralized allocation before? If yes, describe the friction and how it was managed.
• Are there incentive structures (bonuses, budgets, scorecards) that systematically bias decisions toward one allocation path? Options: Yes — compensation, Yes — budgeting process, Yes — P&L ownership, No obvious incentives, Unsure
• What escalation or change-management steps would you expect us to take if we hit that derailment risk?
• How comfortable would you be with an explicit governance cadence (decision gates, rehearsal, evidence checklist) versus informal alignment? Options: Prefer formal cadence, Prefer informal alignment, Hybrid approach, Unsure

Readiness — Do We Have What We Need to Move Fast?

• If we had to brief the board in four weeks, what critical data or access would be missing?
• Which systems hold the source data we’ll need (select all that apply)? Options: ERP / GL, Treasury system, FP&A models, Capex tracker, M&A / transaction ledger, CRM / Revenue system, Other
• How clean and consolidated is your historical transaction and cashflow data? Options: Well consolidated and auditable, Mostly consolidated with gaps, Fragmented with significant gaps, Significant quality issues
• Who will be the day-to-day point of contact for data, assumptions, and model questions (name and role)?
• Realistically, what timeline do you expect for: framework design, board rehearsal, and final sign-off? Options: 6 weeks / 2 weeks / 4 weeks, 8 weeks / 3 weeks / 4 weeks, 12 weeks / 4 weeks / 6 weeks, Other

How Should We Work Together — Commitments & Next Steps

• What would cause you to walk away before we get to the board (deal-breakers for the engagement)? Options: Lack of access to data, Misaligned incentives, Unclear governance, Price / fee concerns, No internal sponsor, Other
• What governance cadence do you prefer for decision gates and updates? Options: Weekly working sessions, Bi-weekly reviews, Monthly steering committee, Ad hoc as needed
• What evidence package will the board or LPs require for approval (pick all that apply)? Options: Full scenario models, Executive slide deck, Peer benchmarking, Independent valuation memo, Legal / tax analysis, Rehearsal transcript / summary
• How do you prefer fees and scope to be structured for this work (fixed, milestone, success fee, retainer)? Options: Fixed-fee engagement, Milestone payments, Retainer + success fee, Hourly / time & materials, Other
• What would make you comfortable signing a mutual commitment to proceed after discovery (specific deliverables or conditions)?

Getting Comfortable — Quick Snapshot

• Which of the following best describes the primary trigger for this capital allocation review? Options: Investor criticism of cash accumulation, PE fund investment-period deadline, Competing internal investment proposals exceed capital, Routine board capital review, Post-transaction funding decision, Other
• Who on your team will be the day-to-day contact for this diagnostic and what are their roles?
• Which stakeholder is expected to make the final allocation recommendation to the board? Options: CFO, CEO, Board/Finance Committee Chair, PE partner / General Partner, Family office principal, Collective decision by executive team, Other
• Approximately how much re-allocable capital (or capital under active review) is in scope for this exercise? Options: < $50M, $50M–$200M, $200M–$500M, $500M–$1B, > $1B, Prefer not to disclose
• What timeline does the board expect for a recommended allocation (from diagnostic start to decision)? Options: Immediate (<30 days), 1–3 months, 3–6 months, 6–12 months, >12 months
• How confident are you that your current internal metrics and hurdles reflect economic reality today? Options: Very confident, Somewhat confident, Skeptical, Not confident at all

Are We Settling for Yesterday’s Rules?

• When was the last time your corporate hurdle rates and return thresholds were formally recalibrated against market comparables and real option value? Options: Within 6 months, 6–12 months, 1–2 years, >2 years, Never
• Walk me through the current methodology for setting hurdle rates—what inputs, judgments, and governance steps are involved?
• Which teams or individuals materially influence these rates today? Options: CFO/Finance, Treasury, FP&A, Business unit leaders, Board/Finance Committee, Compensation committee, External advisors, Other
• How do you account for strategic optionality or competitive positioning when translating project-level returns into corporate allocation decisions? Options: Captured qualitatively, Quantified via scenario models, Ignored / not captured, Inconsistently considered, Other
• How often does the board request multiple valuation scenarios (e.g., downside, base, upside) tied to capital allocation choices? Options: Always, Often, Sometimes, Rarely, Never

Where the Money Actually Lives and Moves

• If we traced every dollar available today, how many discrete 'pots' of capital would we find and who controls them?
• Which of the following liquidity pools are in scope or constrained for reallocation? Options: Unrestricted cash, Committed cash for deals, Short-term marketable securities, Credit facility capacity, Board-designated reserves, Restricted cash (covenants or contractually earmarked), Shareholder/LP-designated capital
• To what extent are those pools fungible for re-deployment today? Options: Fully fungible, Partially fungible with approvals, Not fungible, Unsure
• Which explicit or implicit restrictions most limit your redeployable liquidity? Options: Debt covenants, Tax/repatriation constraints, Investor/LP mandates, Board policy, Operational cash needs, Regulatory/legal restrictions, Other
• When was the last time you ran a liquidity stress test tied to adverse allocation outcomes (e.g., delay in monetization, prolonged capex ramp)? Options: Within 3 months, 3–12 months, >12 months, Never

What Keeps You Awake at 2 AM?

• Which potential allocation mistake today would do the most damage to the company’s valuation or optionality?
• Are there historical allocation decisions that you regret—what went wrong and what lesson stuck with leadership?
• Which stakeholders are most likely to escalate or politicize allocation choices? Options: Board / Finance Committee, Largest investors / LPs, CEO / Executive team, Business unit leaders, Employees / union, External regulators, Other
• How does the fear of reputational or political backlash influence your appetite for bold reallocation? Options: Severely constrains appetite, Moderately constrains, Minor effect, No effect
• Describe a time when political pressure caused a materially different capital decision than the model suggested.

How We Decide — Hidden Biases and Hurdles

• Which internal habit or incentive structure do you think most consistently misprices projects (for example: optimism bias, inertia, compensation-linked KPIs, or siloed P&Ls)? Options: Optimism / forecast bias, Inertia / historical precedent, Compensation-linked metrics, Siloed P&Ls and local incentives, Executive politics, Other
• How do business unit leaders typically advocate for funding—data-driven cases, future narratives, relationship channels, or something else?
• Where do approval gates most often break down (e.g., timing, incomplete info, lack of accountability)?
• How do you currently account for opportunity cost when comparing competing allocation proposals? Options: Formal portfolio-level optimization, Simple NPV comparisons, Rule-of-thumb estimates, Not quantified, Other
• Is there a forum or role that consistently plays 'devil’s advocate' on allocation decisions? If not, why not? Options: Yes—internal committee, Yes—external advisor, No, informal challenge only, No formal challenger role

When Models Break — Failure Modes in Action

• Tell us about a recent model-led allocation decision that failed—what assumptions collapsed and how did the organization respond?
• Which model inputs make you the least comfortable (pick all that apply)? Options: Revenue growth by segment, Margin expansion assumptions, Exit / valuation multiples, Discount rates / cost of capital, Timing of cash flows, Macro / FX assumptions, Capital structure / refinancing risk
• How reproducible and auditable are your core allocation models today? Options: Fully reproducible with version control and docs, Mostly reproducible but fragmented, Ad hoc spreadsheets requiring a single person, Not reproducible / unknown
• If we needed to rebuild your central allocation scenario suite from scratch, how long and what resources would that realistically require? Options: <24 hours / small team, 1–3 days / FP&A lead, 1–2 weeks / multi-discipline team, >2 weeks / significant effort, Unknown
• What documentation exists for model inputs, assumptions, and data sources? Please list or describe.

If You Could Reimagine Capital Allocation

• If you could change one thing about how capital allocation decisions are made today, what single change would likely produce the largest valuation or strategic benefit?
• Which allocation outcomes matter most to your board and investors (select top three)? Options: Valuation uplift / multiple expansion, Liquidity / runway extension, Strategic optionality / growth optionality, EPS accretion, De-risking the balance sheet, Return on invested capital / IRR, Other
• What measurable signals would convince you and the board that a new allocation framework is working? Options: Modeled valuation delta realized, Improved IRR / ROIC on deployed capital, Faster execution / time to deployment, Higher board approval rates, Investor endorsement / positive commentary, Reduced volatility in cash runway, Other
• How would you like portfolio-level reporting to change to make allocation trade-offs clearer to non-finance board members?
• What level of independence or separation between advisory and execution would make you trust recommendations most? Options: Fully independent, no execution ties, Limited execution involvement with disclosure, Execution allowed if conflicts disclosed, No preference / unsure

What Would It Take to Change Course?

• What specific evidence would persuade your board to choose a model-driven reallocation over politically expedient options? Options: Modeled valuation uplift >X%, Third-party validation of assumptions, Pilot demonstrating outperformance, Investor/LP endorsement, Clear contingency plans and governance, Other
• Who must sign off to run a time-boxed diagnostic or pilot (list names/titles and their likely stance)?
• What non-negotiables would you require in a proposed advisory engagement (e.g., timing, governance cadence, fee structure, confidentiality)?
• Would you consider a limited-scope pilot (e.g., applying the framework to one business unit or a tranche of capital) to de-risk adoption? Options: Yes—definitely, Maybe, with conditions, No
• If yes or maybe, what pilot size would be meaningful but manageable (choose best fit)? Options: <$10M, $10M–$50M, $50M–$200M, >$200M, Unsure

Setting the Table: A Quick Read on Where You Are

• What is the single primary objective for this deployment window (board sign-off, capital call, portfolio action, etc.)? Options: Board approval of allocation framework, Decision to deploy capital (M&A, buybacks, capex), Finalize financing structure, Satisfy LP/investor deadline, Other
• What is your target timeline for the next meaningful milestone (e.g., rehearsal, final model delivery, board packet distribution)? Options: < 2 weeks, 2–4 weeks, 1–2 months, 2–3 months, Flexible/unspecified
• Who is the person expected to present the recommendation to the board or committee?
• On a scale-from-words: how would you describe your current overall confidence that the team can execute this deployment? (briefly explain) Options: Very confident, Moderately confident, Worried, Not ready
• If we left today, what's the one thing you’d want completed in the next 48 hours to feel progress?

What Would Break This Before It Starts?

• Which single issue — data, model assumption, stakeholder pushback, or governance gap — would cause you to halt deployment immediately? Options: Key dataset missing/unreliable, Critical model assumption invalid, Major stakeholder not aligned, Board/LP process not defined, Other
• Which specific datasets or reports are incomplete or inconsistent today? Please name them (e.g., cash forecast, segment P&L, valuation comps).
• How long has each identified gap existed (days, months, years)? Options: Under 1 month, 1–3 months, 3–12 months, Over a year, Unknown
• When past capital reviews encountered one of these failures, what was the real-world consequence (delayed decision, wrong allocation, reputational fallout)? Options: Decision delay, Poor allocation outcome, Board override, Investor criticism, Other
• How does this potential failure feel politically—manageable with prep, or likely to become a major fight? Options: Manageable, Risk of pushback, Likely major conflict, Unsure

Who Will Carry the Torch? Mapping Accountability

• If the board asks who owned a modeling error that changed the recommendation, who would you name first?
• Please select which stakeholders will own each artifact (data feeds, model, board deck, Q&A log, execution plan). Options: CFO/finance, Treasury, Business unit lead, Strategy team, External advisor, Legal/Compliance, Other
• For each owner you selected, do they have clear authority to make decisions or only to recommend? Options: Has decision authority, Recommends only, Shared authority, Unclear
• Where do you expect the biggest ownership friction to appear (e.g., business unit versus corporate finance)? Options: Business unit vs corporate finance, Treasury vs strategy, External advisor vs management, Legal/compliance constraints, None anticipated
• If a stakeholder refuses to comply with a data request or rehearsal, what escalation path would you use and how long would it take?

Which Assumptions Would Move the Needle?

• Name the one assumption that, if it shifted by 5–10%, would change your recommendation. What is it?
• Which of the following categories contain your top 3 assumptions (select up to 3)? Options: Revenue growth / market share, Margin assumptions, Discount rate / cost of capital, Exit multiples / valuation comps, Synergy capture, Liquidity timing, Other
• Have sensitivity analyses been performed on those assumptions and are the outputs documented? Options: Yes — full sensitivities and doc, Partial — some scenarios only, No — plan to do during sprints, No — not planned
• Who will independently validate key assumptions (internal reviewer, audit, external advisor)? Options: Internal reviewer, Internal audit, External advisor, Board committee, No independent validation planned
• If an assumption proved wrong after board sign-off, what is your preferred remediation: stop, pause & re-model, or proceed with contingency? Briefly explain. Options: Stop and re-evaluate, Pause and remap, Proceed with contingency, Depends on magnitude

Are the Numbers Truly Reproducible?

• Can an independent analyst reproduce the model outputs from source files and documented steps within one day? Options: Yes, reproducible in <1 day, Yes, but needs >1 day, Partial reproducibility, Not reproducible today
• Which model governance controls are in place (version control, change log, peer review, audit trail)? Options: Version control, Change log, Peer review, Audit trail, None of the above
• Where are the canonical source files stored and who has edit rights? Options: Secure shared drive, Enterprise data warehouse, Local spreadsheets, Cloud collaboration (e.g., OneDrive, Google), External advisor’s environment
• When was the model last stress-tested against an adverse macro scenario and what changed? Options: Within last month, 1–3 months, 3–12 months, Over a year, Never
• If we asked you for a reproducibility checklist, which three items would you prioritize?

Board Rehearsal: Are We Ready to Face the Room?

• What is the single hardest question the board could ask that we are least prepared to answer?
• Have you scheduled a full-dress rehearsal with the expected panel and a hostile Q&A simulation? Options: Yes — scheduled with panel, Planned but not scheduled, No rehearsal planned, Rehearsal with select stakeholders only
• Which materials are ready for the rehearsal (slide deck, appendix, model extracts, Q&A memo, one-page summary)? Options: None ready, Slide deck, Appendix data pack, Exported model sheets, Q&A memo, One-page summary
• Who will role-play the skeptical board member(s) during rehearsal, and do they have authority to pushback authentically? Options: Internal execs, Independent advisor, Board committee member, External facilitator, No realistic role-play planned
• After rehearsal, what are the top three actions you expect to emerge and who will own them?

Data & Systems: Is the Foundation Solid?

• Which single dataset, if corrected, would materially change liquidity or valuation metrics?
• How frequently do your core data feeds refresh (daily, weekly, monthly) and is that cadence sufficient for the decision? Options: Daily, Weekly, Monthly, Ad-hoc/manual, Unknown
• Who is the data owner for each critical feed and do they have SLA commitments? Options: Finance data owner, Treasury, IT/BI, Business unit owner, External provider, No clear owner
• Describe current reconciliation processes—automated, manual, sampled—and how long end-to-end reconciliation takes. Options: Fully automated, Hybrid automated/manual, Manual, No formal reconciliation
• Have any recent audits or incidents flagged data integrity issues? If so, what were the fixes and when? Options: Yes — recent with fixes, Yes — open issues, No audits flagged issues, No audits performed

Decision Gates & Contingencies — When Do We Stop?

• What explicit metric or trigger would cause you to stop execution mid-deployment (e.g., cash shortfall, covenant breach, adverse valuation change)?
• Which monitoring metrics will be tracked in real-time during execution (select all that apply)? Options: Cash runway, Deal pricing variance, Synergy realization, Market multiple movement, Debt covenant headroom, Other
• Who has authority to enact the stop/pause and what is the expected notification timeline to the board/LPs? Options: CEO/CFO, Board chair, Finance committee, External advisor, No clear authority
• What contingency playbooks exist today (alternative financing, phased execution, fallback allocations) and who can activate them? Options: Alternative financing, Phased execution, Hold funding, Sell assets/portfolio rebalancing, None documented
• If a trigger fires, how quickly can you implement the contingency (hours, days, weeks)? Options: Under 24 hours, 1–3 days, One week, Multiple weeks, Not sure

Final Logistics & Commitments: Clear Next Steps

• If we leave this session with one agreed immediate deliverable, what should it be? Options: Complete data pack, Revised model assumptions, Schedule rehearsal, Owner RACI confirmation, Contingency plan
• Which of the following sprint milestones do you want scheduled first? Options: Modeling sprint (sensitivity work), Data reconciliation sprint, Board deck draft, Full-dress rehearsal, Execution checklist finalization
• Who will be the single point of contact we check progress with, and what is their preferred communication cadence?
• Looking at the whole readiness picture, how would you rate your deployment readiness today? Options: Green — ready, Yellow — minor gaps, Orange — significant gaps, Red — not ready
• What remaining concern keeps you up at night about this deployment, and what would make that worry go away?

Opening: The Real Reason We're Here

• What's the immediate trigger that prompted this capital-allocation review? Options: Investor criticism about cash accumulation, PE fund investment-period deadline, Competing internal investment proposals, Board request after strategic update, Management concern about dilution, Other
• Who will be the primary internal sponsor and final presenter to the board or investment committee? Options: CFO, CEO, Head of Strategy, Head of Corporate Development, Board Finance Chair, PE Partner, Other
• What timeline are you targeting for a board or LP decision on allocation recommendations? Options: Within 2 weeks, Within 1 month, 1–2 months, 2–3 months, Longer than 3 months
• In one sentence, what would make this review feel like a clear success to you personally?
• Which of the following outcomes matter most to your sponsors right now? Options: Valuation uplift, Improved liquidity profile, Reduced dilution, Faster deployment of dry powder, Clear governance & approval package, Other

Are We Just Living With Old Rules?

• When was the last time your internal hurdle rates led to a decision you later wished you'd changed?
• How often do you formally revisit hurdle rates and capital allocation guardrails? Options: Quarterly, Biannually, Annually, Only after major events, Never
• Who currently owns the calibration of hurdle rates and what inputs do they use? Options: CFO/Finance, Treasury, Strategy/Corporate Development, External advisors, No single owner, Other
• Have your historical allocation patterns produced measurable opportunity cost (e.g., missed M&A, lost market share)? Please give a concrete example.
• How emotionally comfortable are you presenting a materially different allocation framework to the board? Options: Very comfortable, Somewhat comfortable, Wary but willing, Not comfortable

Who Wins Under the Current System — And Who Loses?

• Who benefits most from the current allocation process—corporate center, business units, shareholders, or specific executives? Options: Corporate center/central allocation, Individual business units, Shareholders/LPs, Specific executives with P&L control, No clear beneficiaries, Other
• Which stakeholders have the most influence (formal or informal) over the final allocation decision? Options: Board, CEO, CFO, Business unit leaders, Major investors/LPs, Other
• Where have you seen politics override analytics in past allocation debates? Describe one recent instance and its consequence.
• Which of the following tend to drive defenders of the status quo in your organization? Options: Fear of being wrong, Personal KPIs tied to spend, Siloed incentives, Insufficient data, Habit/cultural inertia, Other
• If we could remove one political friction today, what would it be and why would that matter?

Where Would the Balance Sheet Bend First?

• If a severe liquidity shock hit tomorrow, which part of your balance sheet is most likely to constrain options? Options: Working capital lines, Short-term investments, Covenant headroom, Debt maturities, Cash on hand, Other
• What is your current cash buffer expressed in months of operating burn? Options: <1 month, 1–3 months, 3–6 months, 6–12 months, >12 months, Unsure
• How is excess cash currently allocated across these buckets? Options: Share buybacks, Debt repayment, Short-term investments, Capex/organic growth, M&A pipeline, Other
• What explicit liquidity triggers do you have (e.g., cash < X months, covenant breach, market drawdown)? List thresholds and owners of the trigger.
• Have you faced a near-miss liquidity episode in the past five years? If yes, what changed afterward? Options: Yes — materially changed policy, Yes — small adjustments, No, Unsure

Do Our Allocation Scenarios Move the Needle on Valuation?

• Which single allocation decision over the last three years would have most likely increased enterprise valuation if it had been made?
• Which valuation metrics carry the most weight with your board or investors? Options: EV/EBITDA, P/E, ROIC, Free cash flow yield, NAV per share, Other
• What types of scenario analysis have you run internally (e.g., dilution vs. growth, buyback vs. acquisition, staged investment)? Options: Simple pro-forma, Full scenario waterfall, Probability-weighted outcomes, Stress tests, None, Other
• Who currently owns the models and can reproduce results end-to-end without manual tweaks? Options: Internal FP&A, Treasury, Strategy team, External advisor, No single owner, Other
• What concerns do you have about model credibility or board trust in modeled outcomes?

What Could Break This Plan, and How Would We Detect It Fast?

• What's the single failure mode most likely to cause the board to reject your recommendation (e.g., political override, model error, market shock, execution failure)? Options: Political override, Modeling error/assumption, Market or macro shock, Execution capability, Liquidity covenant breach, Other
• What monitoring metrics would you want agreed up front to detect that a chosen allocation path is off-track? Options: Revenue growth vs plan, Margin compression, Cash burn vs forecast, M&A integration milestones, Share-price sensitivity, Other
• Who will be responsible for near-term monitoring and who signs off on triggers to pause or pivot? Options: CFO, Treasury, Head of Strategy, Board Finance Chair, Investment Committee, Other
• What contingency actions would be acceptable (e.g., stop funding, accelerate buybacks, seek bridge financing) and who would authorize them?
• How quickly must a contingency trigger translate into a board-level decision to be effective? Options: Immediate/within 24 hours, Within 1 week, 2–4 weeks, One quarter, Depends on trigger

If This Worked, What Would You Show the Board?

• Imagine the board publicly applauding your allocation recommendation — what three pieces of evidence would they cite? Options: Quantified scenario models, Calibrated hurdle rates, Independent valuation or benchmarking, Clear execution plan, Defined monitoring & contingency plan, Other
• Which of those evidence pieces are currently missing, weak, or untrusted? Options: Scenario models, Hurdle calibration, Independent benchmarks, Execution plan, Monitoring framework, All are in place
• What time horizon would you present as the primary lens for measuring success (e.g., next 12 months, 24 months, 5 years)? Options: 12 months, 24 months, 36 months, 5+ years, Varies by initiative
• What emotional outcome matters most if we succeed — relief, validation, increased risk appetite, or something else? Options: Relief, Validation, Confidence to act, Mandate to centralize, Other

Commitment & Next Steps — Who Will Carry the Torch?

• If we walk out today without clear owners and dates, which part of this effort is most likely to stall? Options: Modeling and assumptions, Board materials and rehearsal, Stakeholder alignment, Execution planning, Monitoring & governance, Other
• Which internal teams must be engaged immediately to make models reproducible and board-ready? Options: FP&A, Treasury, Corporate Development, Legal/Compliance, Investor Relations, Business Unit Finance, Other
• What governance cadence would you accept for making allocation decisions and reviewing outcomes? Options: Weekly working group, Biweekly steering committee, Monthly executive review, Quarterly board-level decision, Ad hoc as needed
• Are you prepared to commit a budget or advisory mandate to complete the diagnostic, models, and board package? If yes, what range feels reasonable? Options: No budget yet, Small advisory engagement (<$50k), Medium ($50k–$200k), Large (>$200k), Prefer to discuss privately
• What are your top three concerns about moving forward with an external capital strategy advisor?
• Who should we schedule a 30–45 minute follow-up with to validate assumptions and agree the evidence package for the board?