Start Here: The Deal in One Breath

• In one sentence, what is the primary objective of this financing (e.g., bolt-on acquisition, dividend recap, growth capital, rescue, refinancing)? Options: Acquisition (bolt-on/strategic), Growth/organic expansion, Dividend recap / liquidity, Recapitalization / balance sheet optimization, Rescue / covenant relief, Refinancing / maturity extension, Other
• What is the target funding amount (ballpark is fine) and preferred currency?
• What is your ideal close window? Options: Immediately (0–2 weeks), Near-term (2–6 weeks), Standard (6–12 weeks), Longer (3+ months), Flexible/unspecified
• Who on your team will lead day-to-day interactions with us (name, role, best contact), and who is the ultimate decision authority?
• Have you run this idea past anyone else (senior lender, other investors, counsel)? If yes, what was the reaction? Options: Not yet discussed, Discussed with lenders — concerns raised, Discussed with lenders — neutral/supportive, Discussed with potential investors — interest expressed, Discussed with counsel — actionable feedback

Who Really Holds the Keys?

• If one person had to approve the deal tomorrow and you were worried about convincing them, who would that be and why?
• Which parties must sign off for this financing to proceed? Options: PE sponsor investment committee, Company board of directors, CFO / CEO sign-off, Existing senior lender(s), Equity co-investors, Outside counsel, Other
• What are the formal approval thresholds (e.g., board majority, sponsor IC unanimous) and are any waivers expected?
• How does each key stakeholder define a ‘win’ for them (sponsor, CFO, counsel)?
• How confident are you that the sponsor, CFO, and counsel are aligned today? Options: Fully aligned, Mostly aligned with minor differences, Significant differences between two parties, Fundamental misalignment

Peek Under the Hood: The Capital Stack as It Stands

• What is the current capital structure (list instruments, outstanding amounts, maturities and priority: senior bank, second lien, mezz, preferred, common)?
• Which claims or liens do you believe have the greatest leverage over outcomes (e.g., first lien bank, vendor liens, tax liens)? Options: First lien bank, Second lien / unitranche, Existing mezzanine/preferred, Trade creditors, Tax authorities, Leaseholders, Other
• What covenants or triggers in existing agreements worry you most (financial covenants, change-of-control, incurrence covenants)? Options: Leverage covenants, Interest coverage covenants, Incurrence / negative pledge, Change-of-control provisions, No-subordination clauses, Consent thresholds for additional debt, Other
• Have any lenders previously withheld consent or put formal conditions on new capital? If yes, how was that resolved? Options: No prior issues, Informal pushback resolved quickly, Formal consent requested and granted, Consent refused / unresolved, Under active negotiation
• Which part of the stack would you be most comfortable subordinating, and which must remain untouched?

The Uncomfortable Cost Question — What's Tolerable?

• What effective cost of capital (all-in, dilution-adjusted) is the sponsor/CFO willing to accept before this becomes a no-go? Options: < 10% (equity-like but low), 10–15%, 15–20%, 20–30%, > 30% / only as last resort
• Would the sponsor prefer: less cash interest and more equity upside, or more fixed cash return and limited upside? Options: Prefer equity upside (lower cash), Prefer higher cash return (lower upside), Balanced / hybrid, Undecided
• Are PIK (payment-in-kind) features acceptable as part of the structure, and if so, to what extent? Options: Not acceptable, Limited PIK for short term, Moderate PIK acceptable, Full PIK acceptable
• What payoff priority and conversion mechanics would be a deal-breaker for the sponsor or senior lenders?
• How should we think about target investor IRR or return profile to align with your exit plan? Options: Target low single digits (control/strategic), Mid-teens, High-teens, 20%+

If Things Go Sideways, Who Do You Want in the Room?

• If cash generation weakens materially, should our investor be a passive lender, an operational partner, or an active restructurer? Options: Passive lender (minimal intervention), Constructive partner (advisory + selective intervention), Active restructurer (rights to step in), Depends on severity
• What governance rights are acceptable (board observer, consent thresholds, veto rights, information rights)? Options: Board observer, Board seat, Reserved matters / veto rights, Enhanced reporting / info rights, No governance beyond financial terms
• How would you feel about a liquidity / conversion waterfall that accelerates investor equity participation on underperformance? Options: Comfortable, Maybe with caps/guardrails, Prefer to avoid, Unsure
• Who on your team should we engage early about operational contingency planning (CFO, COO, head of FP&A)? Options: CFO, COO, Head of FP&A, Treasurer, CEO, Other
• How long has the team carried a contingency plan for downside scenarios, and has it ever been executed? Options: No plan, Plan created recently, Plan in place >1 year, Plan executed before

The Lender & Counsel Minefield — Who Could Slow Us Down?

• Which lenders or external parties are most likely to oppose or heavily condition this transaction, and why?
• Who is your lead counsel for this financing and are they willing/able to move on the anticipated timeline? Options: Internal counsel only, External law firm (name), No counsel appointed yet, Using both internal and external
• Are there any existing forbearance agreements, amendments, or pending waiver requests we should know about? Options: No, Yes — forbearance in place, Yes — amendment pending, Yes — waiver requested
• How quickly can your counsel provide redlines and litigation / consent histories if requested? Options: Within 24–48 hours, 3–5 business days, 1–2 weeks, Longer / variable
• Would you be open to us coordinating directly with senior lender counsel to streamline consents? Options: Yes — encouraged, Maybe — prefer sponsor-led, No — not comfortable

Where It's Hurting: Past Attempts and Uncomfortable Truths

• Tell us about a previous financing effort that stalled or failed — what exactly happened and what was the root cause?
• What internal dynamics (timing, politics, resource constraints) tend to slow decisions in your sponsor/CFO relationship?
• How resilient is the internal timeline — if we hit a snag with consents, how long can the sponsor wait before the opportunity is jeopardized? Options: Days, 1–2 weeks, 3–6 weeks, 3+ months, No firm deadline
• What’s the single recurring obstacle you wish you could eliminate across deals like this?
• On a scale of 1–10, how emotionally and operationally committed is the sponsor to closing this strategy even if it means complex documentation? Options: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10

Designing the Right Structure — Tradeoffs You’re Willing to Make

• Which tradeoff resonates most with the sponsor right now: lower dilution with looser covenants, or tighter covenants with lower price? Options: Lower dilution, looser covenants, Tighter covenants, lower price, Balanced/hybrid, Undecided
• Would the sponsor accept staged economics (step-up rates, conversion tranches) tied to performance milestones? Options: Yes — comfortable, Yes — with caps, Prefer single economics, No
• How important is predictability of cash interest versus preserving runway by deferring cash (PIK or toggles)? Options: Prefer predictable cash interest, Prefer runway via PIK/toggles, Open to hybrid solutions
• Are there governance redlines we must avoid (e.g., no board seat, no veto on budgets)? Please list.
• Would an equity kicker or co-investment be attractive to align incentives with the sponsor? If so, approximate target equity % or economics. Options: No equity kicker, Small equity kicker (<=5%), Moderate (5–15%), Significant (>15%), Undecided

Success, Specifically — How Each Party Measures a Win

• If we closed this deal exactly right, what three outcomes would the sponsor celebrate first?
• What are the CFO’s primary success metrics post-close (cash runway, covenant headroom, EBITDA targets, information cadence)? Options: Cash runway extension, Improved covenant headroom, EBITDA stabilization/growth, Reduced near-term maturities, Improved reporting/controls
• What does counsel need to see to sign off quickly (clear intercreditor language, caps on dilution, defined consent process)?
• What monitoring, reporting, or covenant structure would make the sponsor comfortable with outside capital in the near-term? Options: Quarterly reporting, Monthly cash reporting, Covenant lite structure, Step-in rights with triggers, Board observer / reporting
• How will we know three months after close that this financing is working? What are the early success signals?

Practical Roadmap — What We Need to Move Quickly

• What documents and data are available immediately (latest financials, cap table, debt agreements, lender contact list)? Options: Full diligence bundle ready, Partial docs available, Only summary info available, No docs consolidated yet
• Can you provide a data room and who will own it on your side? Options: Yes — sponsor-owned, Yes — company-owned, We can create one quickly, No current data room
• What consent or information deadlines do we need to meet to keep the deal on track?
• Who are the top three internal and external contacts (name, role, email) we should copy on transaction-level decisions?
• What’s a realistic first milestone we can commit to together (term sheet, lender outreach, consent mapping)? Options: Shared term sheet in 1 week, Preliminary lender outreach in 2 weeks, Consent mapping in 2 weeks, Initial term economics in 48–72 hours

Comfort Check — Emotional and Political Readiness

• How would you describe the sponsor’s appetite for complexity on a scale from 1 (avoid complexity) to 10 (comfortable with bespoke structures)? Options: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10
• Are there political or reputational considerations that could influence terms (LP sensitivities, public perception, competitor reactions)? Options: No major concerns, Minor reputational considerations, Significant LP or market sensitivities, Regulatory/public scrutiny potential
• What internal stories or narratives would you like us to avoid when structuring or marketing this capital?
• How important is speed relative to price and complexity (rank the three priorities)? Options: Speed > Price > Complexity, Price > Speed > Complexity, Complexity manageable if price/right, Other
• If we could remove one internal obstacle today, what would it be and how might that change outcomes?

Commitments & Next Steps — Aligning on an Immediate Plan

• Are you ready to proceed to a preliminary term conversation with us within the timeline you shared? Options: Yes — ready now, Yes — ready in 1–2 weeks, Need internal alignment first, Not ready
• What would you need from us in the next 72 hours to say 'let’s pursue this' (indicative economics, consent strategy, term sheet draft)? Options: Indicative terms, Consent strategy memo, Preliminary term sheet, Lender outreach plan, Intro call with deal team
• Who will be our single point of contact for decisions and approvals moving forward?
• Please confirm any absolute deal breakers we must avoid in a proposal (list non-negotiables).
• Would you like us to prepare a short consent-risk map and an initial term sketch for your internal review? Options: Yes — consent map + term sketch, Yes — term sketch only, Maybe — need discussion, No, not at this time

Tell Me the One‑Line Story

• In one sentence, how would you summarize the capital objective you’re trying to achieve right now?
• Which financing need best captures this situation? Options: Acquisition financing, Growth / capex, Dividend recap / shareholder liquidity, Recapitalization / balance sheet repair, Refinance existing subordinated capital, Rescue / covenant relief, Other
• Who is ultimately driving the decision internally (select all roles that apply)? Options: PE deal partner / MD, Portfolio company CFO, CEO / President, Board / Investment Committee, Company counsel, Sponsor counsel, Other
• What is your target timing to have capital committed and funded? Options: < 30 days, 30–60 days, 60–90 days, 3–6 months, 6+ months, Not sure
• Do you already have any term sheets, LOIs, or lender letters in hand? Options: Yes — binding term sheet, Yes — non‑binding LOI, Term sheets in market but no offers yet, No, exploring options, Planned in next 2 weeks
• Please paste a short summary or link to the current cap table or attach key figures (round numbers OK).

Where Does the Money Actually Live Today?

• If your capital stack were a building, which floors feel most likely to crack under pressure?
• Which of the following instruments exist today in your capital structure (select all that apply)? Options: Revolving credit facility (bank), Term loans (bank), High‑yield / bond, Subordinated debt / mezzanine, Preferred equity / preferred stock, Convertible notes, Payment‑in‑kind (PIK) instruments, Vendor / seller notes, Unfunded commitments (LP backstops), Common equity
• For each material tranche, please list approximate outstanding principal (or attach schedule).
• Are there any off‑balance obligations, guarantees, or contingent liabilities that materially affect senior lender coverage tests? Options: Yes — material (describe), Yes — immaterial, No, Not sure / need to check
• How current is the capital schedule you rely on (select the best answer)? Options: Updated this week, Updated this month, Updated this quarter, Older than a quarter, No formal cap table / reconciliation
• Who owns the economics vs who holds the claims (briefly describe mismatches or complex preferred rights).

Who Gets to Say Yes or No?

• Which counterparty — lender, investor, or holder — would most likely veto the solution you prefer?
• Which parties hold express consent rights that could constrain new subordinated or equity‑like capital (select all that apply)? Options: First‑lien banks, Second‑lien / mezz lenders, Bond trustee / indenture, Existing preferred holders, Significant minority equity holders, Governmental / regulatory approvals, Other
• Which documents contain the most restrictive provisions (restricted payments, pari passu clauses, change‑of‑control, or incurrence covenants)? Options: Credit agreement / facility, Indenture / bond docs, Existing subordination agreement, Shareholders' agreement, None / unclear, Other
• Have you obtained written or verbal indications from senior lenders regarding tolerance for subordination or new preferred equity? Options: Written comfort / waiver in hand, Verbal openness but no documentation, Firm refusal historically, No discussions yet, Not sure
• Which stakeholders are most likely to be constructive in negotiating intercreditor terms — and why?
• How would a lender refusal to consent typically impact the timeline or structure you can accept? Options: Delay 2–4 weeks, Delay 1–3 months, Force alternative instrument (more expensive), Kill the transaction, Unsure

Where the Covenants Bite: What Keeps You Up at Night?

• Which covenant would you expect to breach first in a downside scenario — and why does that one feel fragile?
• Which covenant types are active in your senior documents today (select all that apply)? Options: Leverage ratio (Debt/EBITDA), Interest coverage, Fixed charge coverage, Minimum liquidity / cash balance, Restricted payments / dividends, Negative pledge / asset sale restrictions, Incurrence covenants, Change of control provisos
• When was the last time you requested a waiver or amendment — and what was the outcome? Options: Within last 30 days, 30–90 days ago, Within last year, Over a year ago, Never requested
• How close are you today to any covenant testing thresholds? Please provide current metric values where possible.
• If a waiver were required, who would lead the negotiation and who would be the final approver?
• If covenants were relaxed, what operational or strategic choices would that unlock for you?

Testing the Tail: Imagine Stress and the Negotiations That Follow

• If revenue fell 30% tomorrow, which outcome do you think is most probable for your capital structure?
• Select the likely actions you and your counterparties would consider under severe stress (select all that apply). Options: Seek covenant waivers, Amend terms / forbearance, Recapitalize with preferred equity, Sell assets or business lines, Bring in rescue investor at high dilution, File for restructuring / bankruptcy
• Have you performed downside cash flow scenarios and a runway analysis — and which scenario is most realistic? Options: Yes — conservative plan (detailed), Yes — high‑level stress tests, Planned but not done, No
• Under the most severe credible stress, what is the estimated time to insolvency or liquidity exhaustion? Options: < 30 days, 30–90 days, 3–6 months, 6–12 months, More than 12 months, Unsure
• Which stakeholder is most likely to act constructively in a downside negotiation — and who is most likely to escalate?
• What compromises would you be willing to make proactively to avoid the worst outcomes (examples: board seat, higher coupon, partial covenants)?

If Constraints Vanished: Freedom to Rebuild

• If you could redesign the capital stack tonight with no consent constraints, what single change would you make first?
• What is your preferred long‑term mix across senior debt, subordinated/structured capital, and common equity? Options: Mostly senior debt (low equity), Balanced debt and preferred, Significant preferred / mezzanine, More common equity (de‑leveraging), Undecided / case‑by‑case
• How much dilution would you consider acceptable in exchange for covenant relief or greater operational flexibility? Options: < 5% economic, 5–15%, 15–30%, 30–50%, >50%, Prefer non‑dilutive alternatives
• Which governance elements are deal‑stoppers for you (select all that would block a deal)? Options: Board control transfer, Veto over budgets, Operational interference, Automatic conversion on default, Information rights beyond normal reporting, None of the above
• What form of structured investor behavior in downside scenarios would make you feel most comfortable (examples: constructive lender, patient capital, active operational support)?
• Would you prefer a fixed contractual solution (detailed intercreditor mechanics) or a looser, relationship‑based covenant package? Options: Strict / contractual with clear mechanics, Relationship‑based with rolling engagement, Hybrid

Operational Readiness: If We Can Solve This, How Fast Can We Move?

• If the right structure and consents are secured, what’s the earliest realistic date you could sign a binding commitment? Options: < 2 weeks, 2–4 weeks, 4–8 weeks, 8–12 weeks, 12+ weeks, Depends on consents
• Who are the internal and external approvers (names/roles) who must sign off before funding can occur?
• Do you have counsel, auditors, and financial statements ready for legal and diligence review? Options: Yes — all ready, Mostly ready (minor items), Need to engage counsel / auditors, Not ready
• Are there parallel processes (M&A, LP approvals, board votes) that could cause timing conflicts? Options: Yes — material timing conflict, Yes — minor scheduling overlap, No parallel processes, Unsure
• What communication cadence and decision milestones would you prefer as we negotiate consents and intercreditor terms? Options: Daily standups, Twice weekly, Weekly, Ad hoc as needed, Milestone based only
• Who should our structured capital team treat as the single point of contact for consent negotiations and term approvals?

Opening: A Quick Deal Snapshot

• Tell us in one sentence what you're trying to accomplish with this financing (the simplest possible statement)
• What is the primary use of proceeds? Options: Acquisition / buy-side financing, Growth / capex expansion, Dividend recap / shareholder liquidity, Recapitalization / balance sheet optimization, Refinance existing structured capital, Other
• What size ticket are you targeting (select the closest range)? Options: <$5M, $5M–$25M, $25M–$75M, $75M–$150M, >$150M, Undisclosed / custom
• How quickly do you need the capital? Options: Immediately (0–30 days), Near-term (30–60 days), Pipeline (60–90 days), 3–6 months, 6+ months
• Who on your side will sign off on proceeding to term sheet? (role names, not people) Options: PE deal partner / MD, Portfolio company CFO, General Counsel / outside counsel, Board / investment committee, Other

What Could Go Wrong (And Hurt You Later)

• If this financing turned out to be a mistake, what single consequence would you least want to explain to your partners? Options: Excessive dilution at exit, Blocking future senior financings, Operational covenants that strangle growth, Investor forcing an undesired sale, Legal entanglements with lenders, Other
• What constraints have you quietly learned to live with in prior financings?
• Which lender consent or covenant has previously derailed alternative capital options for you? Options: Change of control consent, Restricted payments / dividend covenants, Incurrence covenants, Subordination / intercreditor approval, No prior consents were required / unknown
• How emotionally comfortable are you with bringing in a capital partner who will have governance or information rights? Options: Very comfortable, Somewhat comfortable, Reluctant but open, Not comfortable
• When you imagine a worst-case scenario during life of the investment, what keeps you awake about investor behavior or control?

Where the Capital Stack Actually Bites

• What's hiding in your capital stack that makes financing choices harder than they look?
• Please select all instruments currently in the capital structure. Options: Senior bank / revolver, Term loan A / unitranche, Second lien, Mezzanine debt, Preferred equity, Convertible notes, Common equity (sponsor + management), Seller note, Other
• List outstanding maturities or amortization bullet dates that materially constrain options (next 24 months)
• Have you previously amended intercreditor agreements or obtained atypical consents? If yes, briefly describe. Options: Yes — multiple times, Yes — once, No, Unknown / under review
• How long has the current capital structure been in place (and when was the last meaningful change)? Options: <6 months, 6–12 months, 1–2 years, 2–5 years, 5+ years
• Which of these covenants feels most constraining today? Options: Fixed charge coverage, Leverage test, Restricted payments, Negative pledge / liens, Change of control, None of the above / unsure

Are We Sure Capital Is the Real Fix?

• What would it feel like to you if the real barrier to your goal wasn’t capital but execution, approvals, or market timing?
• What operational or commercial milestones must be achieved before new capital creates value (revenue targets, EBITDA, integration steps)?
• Have you modeled outcomes both with and without an equity kicker or conversion option? What surprised you? Options: Yes — material differences, Yes — modest differences, No, Started but incomplete
• If the capital raises friction with key customers, suppliers, or employees, how long could you absorb that before it affects growth? Options: <3 months, 3–6 months, 6–12 months, 12+ months, Unsure
• Which non-financial supports from a capital partner would move the needle for you (operational help, board guidance, buy-side introductions)? Options: Operational playbook / CEO coaching, M&A / add-on sourcing, Treasury & banking introductions, Governance support, None / purely capital

Design Principles: What a Constructive Partner Actually Does

• Would you rather a capital provider who largely stays passive or one who actively engages during stressed periods—even if that increases oversight? Options: Prefer passive capital, Prefer constructive active partner, Depends on economics and rights, Unsure
• What governance trade-offs are you willing to make for better economics (e.g., board observer vs. preferred liquidation preference)?
• Which conversion mechanics feel acceptable to you? Options: Fixed conversion price, Market-based / VWAP over a period, Equity-settled with anti-dilution protections, Optional conversion upon default, Prefer no conversion / pure preferred
• How important is it that the investor commits to hold-to-maturity versus syndicating or selling the position? Options: Critical — want hold-to-maturity, Prefer hold-to-maturity but flexible, Neutral, Prefer syndication for speed/liquidity
• If a downside governance mechanism (e.g., cash sweep, standstill) is required, what would feel like an acceptable trigger point? Options: Missed interest / cashflow covenant, Leverage breach, Loss of sponsor support, Material covenant default, Only upon insolvency

Which Terms Will Make This Closeable (and Which Won’t)

• Tell us the top three deal terms you cannot compromise on (economics, governance, timing — list them)
• Which economics are you most sensitive to? Options: Cash coupon / interest, PIK interest, Equity participation / warrants, Upfront fees, Preferred return / IRR target
• Would you accept a higher cash coupon in exchange for less governance? If yes, where is the break point? Options: Yes — up to X% more, Maybe — depends on terms, No — governance non-negotiable, Unsure
• How do you prefer downside liquidation priority to be documented (clear waterfall, intercreditor schedule, or principle-based covenant)? Options: Detailed waterfall / schedule, High-level intercreditor principles, Rely on counsel to negotiate, Undecided
• What would constitute a deal-killer clause for you in legal documentation?

Execution Reality: The People, Counsel, and Timelines

• Who are the critical external parties we must engage and get aligned for a timely close? Options: Existing senior lender(s), Administrative agent, Sponsor counsel, Company counsel, Board / Investment Committee, Other
• Which counsel is already committed to this path (name the firm or 'not yet retained')
• What consent approvals are likely required from existing lenders or stakeholders? Options: Majority lender consent, Unanimous lender consent, Administrative agent approval only, Board approval, No consents expected, Unsure
• How long do you realistically expect consent processes to take for this capital solution? Options: <2 weeks, 2–4 weeks, 4–8 weeks, 8–12 weeks, 12+ weeks, Unsure
• Who on your team will be the day-to-day owner for diligence, and how much bandwidth do they have? Options: CFO — full bandwidth, CFO — limited bandwidth, Head of Finance, Sponsor deal partner, Dedicated transaction manager, Other

How You’ll Judge Success (And Be Proud)

• What are the one to three success metrics you will use to evaluate whether this financing was the right call? Options: Preserved sponsor ownership %, Lowered blended cost of capital, Enabled target acquisition / growth, Improved liquidity for shareholders, Operational stability through runway, Other
• When would you want a formal post-close review to assess whether the structure is working? Options: 30 days, 90 days, 6 months, At next board review, Unsure / situational
• What lessons or reporting would you want the investor to provide as part of ongoing monitoring? Options: Quarterly financials + covenant dashboard, Early warning triggers, Operational KPIs, Ad hoc executive summaries, Minimal reporting — only required items
• Would a willingness to participate in a remediation plan (if things go sideways) increase the attractiveness of a partner? Options: Yes — highly attractive, Somewhat, No — prefer hands-off, Depends on economics
• How likely are you to recommend this capital provider to other sponsors if the deal meets your success metrics? Options: Very likely, Somewhat likely, Neutral, Unlikely

Next Steps — What Would Make Us Move Fast Together

• If we agreed on principal terms today, what is the single biggest obstacle that could stop a 60–90 day close? Options: Lender consents, Complex intercreditor negotiation, Sponsor / board approval, Operational diligence gaps, Legal documentation timeline, Other
• What are three documents or data items we should see first in the data room to accelerate diligence? Options: Most recent 3 years financials, Existing credit agreement(s), Cap table & equity agreements, Org chart and management bios, Material contracts, Other
• Who should be on the initial 30-minute alignment call from your side (role and availability window)?
• Would you like us to prepare a brief term sheet with multiple structure options (preferred, convertible, mezzanine) for comparison? Options: Yes — three options, Yes — two options, Prefer one focused option, Not yet
• Anything else we haven't asked that would change how we design a solution for you?

Quick Intro: Who’s in the Room and What’s Pressing

• Who are the primary decision-makers and advisors for this opportunity (roles and names if possible)? Options: PE Sponsor Deal Partner, CFO, CEO/President, Board Chair, General Counsel, Outside Counsel, Debt Advisor/IB, Other
• Give us a one-sentence description of the transaction you’re exploring (purpose: acquisition, growth, recap, liquidity, rescue, other). Options: Acquisition, Growth capital, Dividend recap / shareholder liquidity, Recapitalization, Rescue / covenant relief, Other
• What is your target timing to have terms in hand and to close? Options: Immediate / <30 days, 30–60 days, 60–90 days, >90 days, Flexible
• On a scale between tactical and existential, how urgent does this feel to you right now—what would happen if nothing changed in 90 days? Options: Tactical (manageable), Challenging (material impact), Time-sensitive (could derail growth), Existential (threat to deal or company)
• What’s the single biggest worry you expect us to solve in this engagement?

If You Had to Bet the Farm, What Would You Change?

• What part of your current financing approach do you suspect is fundamentally limiting value creation or deal optionality?
• How long has that constraint been in place and how has it affected deal cadence or valuation in practice? Options: Months, 1–2 years, 2–5 years, 5+ years
• Tell us about a recent transaction where that limitation forced a suboptimal outcome—what specifically happened?
• Who internally is most frustrated by this—what do they say in meetings when the constraint comes up? Options: Sponsor deal team, CFO/finance team, CEO/management, Board, Outside counsel, Debt advisor, Other
• If you were free to break the usual rules, what bold structural change would you consider to fix this problem?

Under the Hood: The Capital Stack That Will Make or Break This

• Which specific obligations, covenants, or lien positions in the current capital structure would force us to stop and rethink any proposed solution?
• Select the instruments and layers that exist today (check all that apply). Options: Senior secured term loan, Revolver / RCF, Second-lien or unitranche, Mezzanine debt, Preferred equity, Convertible instruments, Common equity, Vendor financing, Other
• What restrictive covenants, negative pledge language, or change-of-control triggers have been most problematic in past deals?
• Which counterparties will need to consent to a new junior capital instrument (list lenders, noteholders, or stakeholders)? Options: Existing bank syndicate, Revolver lenders, Second-lien lenders, Bondholders, Significant minority equity holders, Other
• Practically speaking, what priority would you accept for the new instrument relative to existing debt? Options: Subordinated to all existing debt, Pari passu with specified tranche, Preferred equity outside debt priority, Flexible depending on economics, Other
• Which single lender or creditor relationship is most fragile and why?

What Winning Actually Looks Like (Sponsor, CFO, Counsel)

• If sponsor, CFO, and counsel each wrote a one-sentence success headline for this deal, what would each say?
• Which of the following outcomes matter most to your stakeholders? (select up to three) Options: Minimize dilution, Lower all-in cost of capital, Speed to close, Limited ongoing covenants, Preserve sponsor governance, Transparent conversion mechanics, Simplicity of documentation
• What is the sponsor’s single non-negotiable objective on economics or governance?
• For counsel, what structural or documentation features would be a deal killer?
• From the CFO’s perspective, which metric or covenant would make this financing an unacceptable burden for ongoing operations?

Cost, Conversion & Downside: The Trade-offs You'd Accept

• What level of future equity dilution or participation would you accept today to avoid immediate cash strain? Options: <5%, 5–15%, 15–25%, >25%, Prefer not to quantify
• How do you prioritize the following compensation mixes for junior capital? Options: Cash interest, Payment-in-kind (PIK), Equity conversion kicker, Equity warrant, Profit participation
• Describe a realistic downside performance scenario for this business and how you would expect an investor to behave if it happened.
• How important is having a clear and enforceable conversion mechanic versus keeping conversion optional or renegotiable? Options: Critical (firm mechanics required), Important but flexible, Prefer optional/negotiable, Undecided
• What are your benchmark expectations for all-in cost of capital for a junior instrument in this situation?

Hidden Roadblocks: Consents, Timelines, and People

• Which lender, counsel position, or stakeholder is most likely to say 'no' during consent negotiations—and what is their probable reason?
• Have you recently obtained or been denied consents that set a precedent? Select all that apply. Options: Consent granted for dividend recap, Consent granted for junior capital, Consent denied for intercreditor change, No recent consent history, Other
• What is the fastest realistic calendar from term agreement to funded close given expected consents and diligence? Options: <30 days, 30–60 days, 60–90 days, >90 days
• Who will own the consent and closing process internally, and when can they prioritize work with external counsel? Options: CFO, General Counsel, Sponsor legal team, External counsel (outside law firm), Debt advisor/IB, Other
• Which documents or diligence items are most likely to slow us down—explain the biggest likely friction points.

Commitment Signals & What Would Make You Pull the Trigger

• What single investor signal would most quickly convert you from exploring to committing? Options: Firm economic offer, Agreement to lead lender conversations, Limited ongoing covenants, Fast close timeline, Clear conversion mechanics, Other
• How likely are the internal approvals required to proceed within your target timeline? Options: High (>75%), Moderate (40–75%), Low (<40%), Unknown/depends on terms
• What are absolute deal breakers we should know before we draft any term sheet?
• Would you consider a short period of exclusivity to finalize terms? If yes, how long would be acceptable? Options: No exclusivity, <2 weeks, 2–4 weeks, 4–8 weeks, Longer
• What post-close investor rights or monitoring would you prefer (select all that apply)? Options: Monthly financials, Quarterly covenant testing, Board observer seat, Limited consent items, Regular strategic check-ins, No ongoing oversight

Final Check: Red Flags, Communication, and Next Steps

• If we leave this conversation with nothing clarified, what is the single worst outcome you face in the next six months?
• Who should be on our core working group (roles and emails if possible) to keep execution moving?
• What is your preferred mode and cadence of communication during diligence and negotiation? Options: Weekly calls, Bi-weekly calls, Weekly written updates, Dedicated portal with updates, Ad-hoc as needed
• What materials or preparations would make you comfortable receiving an LOI or term sheet from us (e.g., indicative economics, consent strategy, timeline)?
• Are there regulatory, tax, or industry-specific issues we need to surface immediately? Options: Tax implications, Regulatory approvals, Foreign ownership rules, Industry-specific regs, No immediate issues, Other
• What is one thing we could do in the next 48 hours that would meaningfully reduce your stress about this deal?