Quick orientation — tell us who we're working with

• Please confirm your role and the core team members we should include in this conversation Options: Treasurer/Head of Treasury, VP of Corporate Finance, CFO, Financial sponsor deal partner, General Counsel, Other (please name)
• What is the legal entity (or entities) that will receive financing or be party to documentation?
• Which market/region should we prioritize for lender outreach (choose all that apply)? Options: North America, EMEA, APAC, Global / multi‑region, Other
• How would you describe the current relationship with your incumbent bank(s)? Options: Strategic partner with strong coverage, Transactional — limited appetite, Over‑concentrated with single bank, Underpenetrated — we want new lenders, Prefer not to say

Where are we on the clock? — urgency, windows, and pressure

• How imminent is the financing need or refinancing deadline? Options: Immediately (within 2 weeks), Near-term (2–6 weeks), Medium (6–12 weeks), Longer than 12 weeks, Timing flexible
• If we slowed down this process, what specifically gets worse and how quickly?
• Rate‑lock windows and pricing cliffs can disappear fast — what hard dates or market windows are we trying to hit?
• How sensitive is the deal economics to a one‑month slip (pick best fit)? Options: Very sensitive — pricing/covenants change materially, Moderately sensitive, Low sensitivity
• Who internally will own keeping us within that timeline (name and role)?

Are we comfortable repeating the same mistakes?

• When you look back at past financings, what recurring pain points keep showing up?
• Which of the following outcomes have you experienced before and would not want repeated? Options: Under‑subscribed syndication, Unfavorable pricing under time pressure, Restrictive covenant package, Documentation delays causing missed rate lock, Rating agency action
• Tell us a short story about the last time a financing surprised you — what happened and what was the cost?
• How long have these challenges persisted and what have you tried to fix them? Options: This is new, A few months, 1–2 years, Several years

If lenders could only see three things about you, what would you want them to see?

• How would you describe your current credit profile in plain language? Options: Investment grade, Upper‑mid market, Sub‑investment grade / high yield, Sponsor backed transitional, Credit challenged / turnaround
• Provide the most recent three financial metrics lenders will care about (e.g., EBITDA, Net Leverage, Interest Coverage).
• Which off‑cycle adjustments or one‑offs should lenders know about when assessing covenant tests? Options: M&A adjustments, COVID/extraordinary items, Capex timing shifts, Working capital seasonality, Other (describe)
• What are the top 2–3 downside scenarios lenders should model? Be specific (e.g., 20% revenue loss in 12 months).

Who needs to be reassured — and what does ‘reassurance’ look like?

• Which stakeholders will sign off on the financing and what are their primary concerns? Options: Treasury, CFO, CEO, Board, Financial sponsor, General Counsel
• For each stakeholder group, what single metric or clause would make them feel the financing is acceptable?
• Where do stakeholder priorities conflict today (for example: lowest coupon vs maximum covenant flexibility)?
• Who is the ultimate decider on trade‑offs between price and covenant protection? Options: Treasurer, CFO, Board/Investment Committee, Sponsor lead, Other
• How do stakeholders prefer to receive updates during the process (frequency and format)? Options: Daily written digest, Twice‑weekly call, Weekly dashboard, Ad‑hoc as material arises, Other

What would ‘mission accomplished’ feel like — be ruthless and specific

• If we achieved a successful financing, list the top three measurable outcomes you would celebrate (be concrete: spread, covenant headroom, tenor, etc.)
• Which of these is most important right now (choose one primary objective)? Options: Lowest all‑in cost, Covenant flexibility / freedom to operate, Speed to close, Broader lender diversification, Longer tenor / structural durability
• What are acceptable trade‑offs (e.g., pay 10bp for two more months to tighten covenants) — please specify limits
• How will you measure success at close and at 90 days post‑close?

Where could the deal actually derail—let’s name the choke points

• Which of the following have derailed deals in the past for you? Options: Covenant negotiations, Lender underwriting concerns, Legal/documentation timing, Credit rating changes, Sponsor commitment changes
• Which documentation milestones do you expect to be the hardest (e.g., confirmation of covenants, security package, intercreditor)?
• Who is your external counsel and what’s their typical responsiveness under compressed timelines?
• If a negotiation stalls, what escalation path has worked before (internal and external)?

Who will run this day‑to‑day so things don’t fall through the cracks?

• Which internal owner will be the single point of contact for lender and advisor coordination?
• How many people on your team can actively support diligence and who are they (roles)? Options: One dedicated owner, Small committee (2–3), Cross‑functional team (4+)
• How much bandwidth can your team realistically give per week during the active outreach/negotiation phase? Options: >20 hours/week, 10–20 hours/week, 5–10 hours/week, <5 hours/week
• Which internal processes tend to slow decisions (procurement, legal review, sponsor sign‑off)?

What paperwork and numbers should we pull first to maintain momentum?

• Which of these documents are current and readily available (pick all that apply)? Options: Last 3 years audited financials, Latest management accounts / 12 months, Debt maturity schedule, Existing credit agreements and covenants, Material contracts list, Cap table / ownership schedule
• Do you already have a data room we can use, and who controls access? Options: Yes — shared with advisors, Yes — but access restricted, No — we will create one, Prefer to discuss
• What are the most sensitive documents and how should we treat them in outreach (e.g., redacted, staged access)?
• Are there any upcoming events (earnings, regulatory filings, material contracts) that could impact lender perception in the next 60 days? Options: Earnings / results release, Material contract renewal, Regulatory milestone, None known, Other

Who do we want in the room — lender mix and sourcing preferences

• Which lender types would you prefer we prioritize for initial outreach? Options: Banks (syndicated), Regional banks, Insurance companies, CLO managers, Direct lenders / private credit, Hybrid
• Are there incumbent lenders we want to include regardless of price or do you want to broaden the syndicate? Options: Include incumbents, Seek replacement where necessary, Open to either — prioritize best economics
• Are there lenders or investor groups you explicitly do NOT want on the deal? Options: Yes — provide names, No
• What level of pre‑commitment/soft circle from anchor lenders would make you comfortable proceeding to documentation? Options: Firm commitments from anchors before docs, Soft circles sufficient to start docs, Need exclusivity period first, Open

How will we know when it’s time to say yes — acceptance criteria

• What non‑negotiable terms must be met before you will accept an offer (be specific: spread, covenant language, tenor, fees)?
• What flexibility do you have to accept slightly worse economics in exchange for structural protections? Options: High flexibility, Some flexibility, Little flexibility, None
• Would you require a final board or sponsor vote to execute once commercial terms are agreed? Options: Yes — board vote, Yes — sponsor vote, No — executive approval only, Depends on materiality
• When should we schedule a short decision checkpoint to review market feedback and refine strategy? Options: Immediately (this week), Within 1–2 weeks, After initial lender outreach (3–4 weeks), Other

Small commitment, clear next step — let’s get moving

• Are you open to a short, no‑obligation credit review from our team to test lender appetite? Options: Yes — proceed, Maybe — need more info, No — not yet
• What would be the ideal outcome of an initial advisory call (pick one)? Options: Refine target structure and timing, Create lender shortlist, Get market pricing indication, Agree on engagement terms
• Please propose 2–3 times for a 45‑minute introductory call this week or next
• Any final concerns or context we should know before that call (sensitive items welcome)?

Quick Snapshot — A One‑Minute Brief

• Who are we speaking with today and what is your role in the financing decision? Options: Treasurer, VP of Finance, CFO, Head of Capital Markets, Sponsor deal partner, General Counsel, Other
• What is the primary objective driving this financing need right now (refinance maturity, acquisition, covenant relief, working capital, other)? Options: Refinance a near-term maturity, Fund an acquisition, Restructure covenants, Raise liquidity / working capital, Replace expensive credit, Other
• Which currency(ies) and legal entities will be in scope for the financing? Options: USD, EUR, GBP, CAD, AUD, Other
• What is the target financing size (ballpark) and the earliest date you would need committed terms?
• How would you rate the urgency on a scale from 1 (planning stage) to 5 (must-close before maturity/bid deadline)? Options: 1, 2, 3, 4, 5

What Would Happen If Today’s Plan Unravels?

• If we failed to secure your target financing this cycle, what are the top three concrete business outcomes you fear most?
• How likely do you think each of those failure outcomes is on a scale from unlikely to very likely? Options: Unlikely, Possible, Likely, Very likely
• When you imagine that downside, who inside or outside the company is most affected and why?
• Have you experienced a near‑miss or breach in the last 24 months that changed the way you view refinancing risk? If so, please describe.
• What steps have you already taken to reduce the chance of those failure modes (e.g., backup facilities, sponsor support letters, covenant waivers)?

Who Really Holds the Keys?

• Who must sign off for a mandate, and who can approve execution day decisions (pricing, rate‑lock, exclusivity)?
• Is there any party that can veto a syndication or force an alternate path (existing bank, sponsor, board, rating agency)? Options: Existing bank, Sponsor / LPs, Board of Directors, Major shareholder, Rating agency, No single veto
• How fixed are your internal timelines for approvals—are they soft target dates or hard deadlines tied to other transactions? Options: Hard deadlines (non‑negotiable), Mostly fixed with limited flexibility, Soft targets (negotiable), Undecided
• Who will be the day‑to‑day point of contact for the advisor and for lender diligence requests? Options: Treasurer, FP&A lead, General Counsel, External counsel, Sponsor rep, Other
• If a short‑notice decision is required (within 24 hours), who is empowered to make it and what is the escalation path?

The Maturity Map — Where the Pressure Really Is

• List the top five debt maturities by date and principal amount that matter most to this financing exercise.
• Are any of those maturities subject to make‑whole, prepayment premiums, or covenant‑triggered acceleration? Options: Make‑whole / premium, Prepayment penalty, Acceleration risk, None of the above, Not sure
• How much of your short–medium term maturities are concentrated with a single lender or banking group? Options: >75%, 50–75%, 25–50%, <25%, No concentration
• Do you have any upcoming amortization or cash sweep events that materially change free cash flow available for debt service? Options: Yes, significant, Yes, moderate, Minor, No, Not sure
• Would you be able to share a maturity schedule or model? If not now, what information would you need to prepare one?

Covenant Reality Check — Are You Walking on Thin Ice?

• Which covenant frameworks currently apply: maintenance covenants, incurrence covenants, reporting covenants, or other bespoke triggers? Options: Maintenance, Incurrence, Reporting / information covenants, Financial reporting timing, Other
• How close are your covenant metrics to testing thresholds today (comfortably above, approaching, or in breach)? Options: Comfortably above, Approaching thresholds, Currently testing borderline, In breach
• What covenant items matter most to your board or sponsor (leverage, interest coverage, secured ratio, liquidity)? Options: Leverage ratio, Interest coverage, Secured/unsecured ratio, Minimum liquidity, Other
• Have lenders recently requested covenant resets, extra reporting, or restrictions on dividends/capex? Please describe any recent asks.
• If covenant flexibility is limited, what non‑covenant levers (pricing, longer tenor, structural protections) would you trade to gain breathing room? Options: Higher pricing, Longer tenor, Amortization relief, Security / collateral changes, Sponsor support, Other

Banks, Lenders, and Hidden Relationships — Who Will Back You?

• Which lender types do you currently rely on and which have been most supportive in stress (relationship banks, regional banks, direct lenders, insurance, CLOs)? Options: Relationship banks, Regional banks, Syndicated banks, Direct lenders, Insurance companies, CLOs, Institutional bond investors
• Which specific banks or lenders would you consider non‑negotiable partners and which would you prefer to replace or diversify away from?
• Have you previously received firm commitments or indications from lenders for this deal? If so, what form (term sheet, verbal, none)? Options: Term sheet, Verbal indication, No indications yet, Under NDA discussions
• How open are you to introducing new lender types (e.g., insurance companies, private credit, bond markets) versus deepening existing bank syndicate? Options: Very open, Somewhat open, Prefer existing banks, Not open
• Are there confidentiality, political, or regulatory constraints that limit which lenders we can approach? Options: Yes – regulatory, Yes – confidentiality, Yes – sponsor restrictions, No constraints, Not sure

Execution Risks & Rate‑Lock Vulnerabilities — Where Timing Breaks Things

• If pricing moves unfavorably, what is the latest acceptable point to pause or change strategy before committing to a suboptimal execution?
• How long of a rate‑lock or pricing window do you need to feel comfortable on the day of closing? Options: 24 hours, 48 hours, 72 hours, One week, Other
• Do you have fallback options if primary syndication is undersubscribed (bridge facility, sponsor bridge, extend maturity with existing bank)? Options: Bridge facility, Sponsor bridge, Extend with existing bank, Asset sales, No fallback
• What operational bottlenecks have derailed closings in the past (document review, legal counsel bandwidth, trustee delays, rating agency timing)? Options: Documentation timing, Legal counsel bandwidth, Trustee/agent delays, Rating agency timing, Other
• Who in your organization needs to be available for last‑minute diligence calls or document signoffs during closing week? Options: Treasurer, CFO, General Counsel, External counsel, Sponsor rep, Finance operations

Operational Readiness — Do You Have the Pieces in Place?

• How complete is your data room and financial model for lender diligence (fully ready, mostly ready, partial, not started)? Options: Fully ready, Mostly ready, Partial, Not started
• What items are most likely to slow diligence: audit gaps, EBITDA adjustments, tax issues, environmental / collateral documentation, or ownership structure complexities? Options: Audit gaps, EBITDA adjustments, Tax issues, Environmental / collateral docs, Ownership structure, Other
• Which external advisors are already engaged (placement agent, rating agency advisor, financial due‑diligence firm, legal counsel)? Options: Placement agent, Rating advisor, Financial DD, Legal counsel, None yet, Other
• Do you have a single‑version financial model that lenders can use, and who owns updates during syndication? Options: Yes — internal owner named, Yes — but ownership unclear, No single model, Not sure
• Are there governance or board reporting cycles that could pause execution during key windows (e.g., quarterly board meeting during syndication)? Options: Yes – likely impact, Maybe – possible delay, No cycles conflicting, Not sure

What Would True Confidence Look Like?

• If we achieved an ideal outcome, what three metrics or signals would tell you we succeeded (pricing target, covenant headroom, committed lender count, tenor)? Options: Pricing target, Covenant headroom, Committed lender count, Tenor achieved, Speed to close, Other
• Which of those success metrics are non‑negotiable and which are tradeable if needed?
• What maximum pricing or covenant concession would you accept before you would rather delay or re‑run the process?
• How important is lender diversity vs. speed—would you accept a smaller fast syndicate or prefer a broader slower one? Options: Prefer fastest path, Balance speed and diversity, Prefer broad, diverse syndicate, Undecided
• Imagine we close to target terms—what operational or governance changes would you implement to avoid repeating this stress in future cycles?

Next Steps — Who Does What and When?

• What would you like the advisor to prioritize in the first two weeks (detailed credit memo, lender outreach list, model reconciliation, data room build)? Options: Credit memo, Lender outreach, Model reconciliation, Data room build, Other
• What are your expectations for communication cadence (daily, every other day, weekly updates, milestone only)? Options: Daily, Every other day, Twice weekly, Weekly, Milestone only
• Who must approve the initial engagement terms and what is your preferred timeline to decide?
• Are there non‑financial constraints we should know about when designing outreach (confidentiality, sponsor sensitivities, public company disclosure windows)? Options: Confidentiality needs, Sponsor sensitivities, Public disclosure constraints, Regulatory limits, None
• What would make you say after our first two weeks: 'Yes—these advisors understand our problem and can run this process'?

Why Are We Talking Now?

• What's the immediate trigger that brought you to explore refinancing or new debt today? Options: Maturing debt within 6 months, Bid deadline for an acquisition, Credit rating pressure/downgrade risk, Liquidity event or covenant breach risk, Other
• How many months remain before the first material maturity or executable bid deadline? Options: <4 weeks, 4–8 weeks, 2–3 months, 3–6 months, 6–12 months, >12 months
• What is the narrowest rate‑lock or pricing window you’re realistically operating within? Options: <72 hours, 3–7 days, 1–2 weeks, 2–4 weeks, More than a month
• Are there any upcoming corporate events (earnings, M&A, investor roadshows) that will materially constrain execution timing? Options: Earnings release, Board approval window, M&A process, Debt or equity raise, Material legal or regulatory date, None of the above

Who Holds the Keys?

• If this financing slips or comes in worse than expected, whose name will be on the line—and are their incentives aligned to prioritize certainty over price? Options: Treasurer, CFO, CEO, Board/Finance Committee, Private equity sponsor, General counsel, Other
• Who is the final decision‑maker for selecting an advisor and signing commercial terms? Options: Treasurer/Head of Finance, CFO, CEO/President, Board or Investment Committee, Private equity sponsor, Other
• Which internal stakeholders must sign off on key tradeoffs (pricing vs covenant vs timeline)? Please name roles and expected approval lead times.
• Have you experienced internal misalignment in past financings? Tell us one example of where that cost time or value.
• How do you prefer we engage stakeholders—single point of contact, steering committee calls, or direct sessions with each owner? Options: Single SPOC (Treasury), Weekly steering calls, Direct sessions with CFO/Board, Ad hoc updates only, Other

What’s Broken Under the Hood?

• What hidden covenant, relationship, or maturity cliff is most likely to derail your refinancing if left unaddressed? Options: Tight leverage covenant, Change‑of‑control covenant, Single‑bank dependency, Upcoming amortization spike, Cross‑default exposure, Other
• Please summarize your debt maturity ladder (amounts and dates) or upload the schedule if available.
• Which existing covenants feel most constraining today (rank top 3)? Options: Total leverage/Net debt to EBITDA, Interest coverage, Restricted payments/dividends, Negative pledge/pari passu, Change‑of‑control, Other
• How reliant are you on one or two incumbent banks to place the majority of the deal? Options: Very reliant, Somewhat reliant, Diversified relationships already, We have no bank relationships
• Have you had a near‑miss or failed syndication in the past 24 months? If so, what specifically failed (timing, appetite, docs, pricing)?

If Lenders Read Your File Today, What Would They Say?

• How would an underwriter likely characterize your credit story today? Options: Compelling/Investment grade profile, Moderate risk but bankable, Borderline/high yield, Material concerns/red flags
• What are the three concrete strengths in your credit profile we should lead with (metrics, contracts, market position)?
• What are the two primary weaknesses or data‑points that lenders are most likely to question?
• What rating agency or public market signals are we dealing with (outlook, watchlist, recent actions)? Options: Stable, Positive, Negative watch, Under review, No agency coverage
• Do you have recent financial projections and covenant testing models ready to share? Options: Yes — fully stress‑tested, Partially ready, No — need support to prepare

What Would Winning Feel Like?

• If we achieve everything you hoped for in this financing, what single outcome will make the board and sponsor feel it was a success? Options: Lowest possible all‑in cost, Max covenant flexibility, Full certainty of funding by deadline, Strategic lender mix/diversification, Minimal documentation risk
• What is your target all‑in pricing band (spread or interest rate) and your absolute maximum acceptable level? Options: Target: <2.0% / Max: <3.0%, Target: 2.0–4.0% / Max: 4.0–6.0%, Target: >4.0% / Max: >6.0%, I prefer to provide a custom range
• Which of these outcomes would you accept trading off if needed (select all you’d be willing to sacrifice to get the others)? Options: Price, Covenant tightness, Speed/timing, Lender mix (retain incumbents), Documentation detail
• Describe one non‑negotiable clause, covenant, or structural feature we must avoid in documentation.
• What minimum lender commitment coverage percentage would make you feel comfortable proceeding to docs (e.g., X% of size priced)? Options: 75%, 80%, 90%, 100%

Where Are You Willing to Compromise?

• Which bargaining chips are you truly comfortable trading to secure certainty—price, covenant, or timeline? Options: Price (willing to pay premium), Covenants (tighter temporarily), Timeline (shorter exclusivity), Fees/structuring concessions, None — must keep all
• What is the maximum incremental cost (bps or fees) you would accept to significantly shorten execution risk? Options: <25 bps, 25–50 bps, 50–100 bps, >100 bps, Prefer to specify in USD fees
• Would you consider staged documentation (binding term sheet then confirmatory docs) or do you require full documentation in one go? Options: Staged approach acceptable, Require full documentation before pricing, Open to either depending on lender appetite
• Are you comfortable granting a short exclusivity period to a lead arranger for the right economics? Options: Yes — up to 7 days, Yes — up to 14 days, Only very short (48–72 hours), No exclusivity
• What concessions on covenants could be time‑limited or subject to performance reopeners? Options: Temporary covenant step‑downs, Earnings‑based testing windows, Carve‑outs for acquisitions, None — covenants must be permanent

Execution Experience — How Do You Want This to Feel?

• Beyond price and covenants, what execution characteristic would make you feel we were exceptional partners? Options: Proactive communications, Clear tradeoff framing, Fast problem resolution, Minimal internal lift, Transparent competitive process
• What communication cadence and formats do your stakeholders expect during syndication and documentation? Options: Daily written updates, Twice‑weekly calls, Weekly steering calls + ad hoc emails, Board‑level briefings only at milestones
• Who should be the single point of contact from our side and who will be your SPOC? Please include backup contacts.
• Which operational owners will drive closing tasks (treasury, legal, tax, treasury operations)? List roles and level of availability.
• How would you like tradeoffs and lender feedback presented—detailed term comparison, executive decision memo, or scenario modeling? Options: Detailed term comparison, Executive memo with recommendation, Scenario P&L and covenant modeling, Combination

Let's Check Readiness — What’s in Place?

• If I asked for your data room today, would it support lender diligence and docs drafting without major follow‑ups? Options: Yes — comprehensive, Mostly ready — a few items missing, Significant gaps — need help to prepare, No data room exists
• Which of the following are already completed or assigned (select all that apply)? Options: Data room assembled, Lead counsel identified, Term‑sheet template available, Internal closing owner assigned, No items completed
• Who is or will be your lead outside counsel on documentation, and do they have extensive syndicated loan or bond experience? Options: Internal counsel only, Big‑law DCM/Bank‑facing counsel, Boutique debt docs counsel, Not yet engaged
• List any third‑party consent, intercreditor, or cross‑default approvals that could delay closing.
• Are there operational capabilities or systems (treasury systems, payments, escrow) that require testing before funds flow? Options: Yes — requires testing, No — ready, Unsure — need assessment

When Should We Pull the Trigger?

• Given market and internal timing, what is the non‑negotiable date by which we must have committed financing? Options: Within 2 weeks, 2–4 weeks, 1–2 months, 2–3 months, Flexible
• What internal approval lead times do we need to accommodate (board, sponsor, auditors)? Options: <1 week, 1–2 weeks, 2–4 weeks, >4 weeks
• Do you have blackout or restricted periods (earnings quiet periods, corporate events) when we cannot execute? Options: Yes — specify dates, No
• What is your preferred rate‑lock approach? Options: Lock at syndication/pricing, Use tips/soft‑lock with pricing confirmation, Staggered locks for portions, No lock preference
• If the primary execution window is missed, what is your fallback plan? Options: Push to backup bank group, Extend maturity with incumbents, Accept higher pricing, Delay until market improves, Other

What Does Success Look Like — 6 Months Out?

• Six months after close, which signal would make you say this financing was unequivocally successful? Options: Achieved target pricing, Covenant headroom intact, No covenant breaches or waivers, Improved lender diversification, Seamless funds flow and treasury ops
• What monitoring cadence and reporting would you like post‑close to ensure covenants are adhered to? Options: Monthly reporting, Quarterly covenant reviews, Ad hoc on events only, Automated dashboard access
• Who will own post‑close covenant monitoring and lender communications inside your organization? Options: Treasury, FP&A/Finance Ops, General counsel, Investor relations, Sponsor
• What lessons or process improvements from past financings would you insist we apply this time?
• Are you open to a short post‑close retrospective with our team to capture learnings and set an improved cadence for covenant monitoring? Options: Yes — schedule within 30 days, Maybe — schedule later, No

Quick Check‑In: What's Brought You Here?

• Briefly describe the financing need or trigger that brought you to explore options now.
• Which of these best describes the trigger for this financing? Options: Near‑term debt maturity, Acquisition financing / bid deadline, Covenant breach or rating concern, Refinancing to improve pricing, Strategic restructuring, Other
• Who will be the primary decision‑maker on the financing (title/role)? Options: Treasurer, VP of Finance/Corporate Finance, CFO, Sponsor deal partner, CEO, Board/Finance Committee, Other
• Which internal and external stakeholders must be consulted or sign off before a final commitment? Options: CFO, Treasurer, Sponsor / PE counsel, Internal Legal, External Counsel, Board / Committee, Rating Agency, External auditors, Other
• If you had to name the single biggest fear about this refinancing process, what would it be?

What's Really at Stake?

• If this financing doesn't close on the terms you need, what is the real cost to the business beyond headline spread—operational, strategic, or reputational?
• Which of the following outcomes would be most damaging if they occurred? Options: Covenant breach / default, Loss of strategic transaction (missed acquisition), Forced expensive bridge financing, Credit rating downgrade, Sponsor or board pressure, Operational constraints / capex cuts
• Can you estimate the likely financial impact (cash, EBITDA, or IRR erosion) if pricing increases or terms tighten materially?
• How tolerant are your stakeholder group(s) to temporary liquidity strain or higher short‑term financing costs? Options: Very tolerant, Somewhat tolerant, Low tolerance, Zero tolerance / cannot accept
• Who inside the company would feel the impact first and most—whose priorities should we structure the deal around? Options: Treasury, CFO / Finance Leadership, Business unit heads, Sponsor / LPs, Board / Audit Committee, Other

Where Things Break Down

• Thinking back on past financings, what recurring point consistently stopped momentum or pushed pricing in the wrong direction?
• How often have you experienced shortfalls in syndication or interest that required last‑minute fixes? Options: Never, Rarely, Occasionally, Frequently, Almost every deal
• Which of these failure modes have occurred or nearly occurred on prior deals? Options: Under‑subscription, Last‑minute covenant imposition, Documentation delays, Rate‑lock missed, Rating agency action, Conflicting lender demands
• Who historically managed lender relationships for you, and what worked or failed about that approach?
• How current and consolidated is your debt maturity, covenant, and bank relationship data? Options: Real‑time and audited, Updated monthly, Quarterly, Ad‑hoc / manual, Fragmented across systems
• When timelines compressed in the past, which trade‑offs did you accept (e.g., worse pricing, weaker lender mix, tighter covenants)?

If This Went Perfectly

• Imagine it's closing day and you call this financing a clear success—what three things must have happened?
• Which specific target outcomes would make you feel the financing hit its mark? Options: Pricing at or below internal spread target, No incremental restrictive covenants, Desired maturity extension achieved, Diverse, high‑quality lender book, Minimal documentation conditions precedents
• What timeline from mandate to close would you consider comfortable and realistic? Options: <4 weeks, 4–6 weeks, 6–8 weeks, >8 weeks
• Which lender types would you prioritize to achieve strategic value (not just price)? Options: Banks / relationship lenders, Insurance companies, CLO managers, Direct lenders / private credit, High‑yield bond investors, Other
• What post‑close covenant monitoring or governance would you want in place to feel protected after closing?
• How should we measure success quantitatively and qualitatively after close? Options: Spread vs target, Syndication coverage (%), Number / quality of lenders, No post‑close covenant waivers, On‑time closing vs rate‑lock

Red Lines, Flex Points, and Hidden Constraints

• What internal or external constraint would you prefer not to discuss but would immediately derail execution if ignored?
• Which covenant types are absolute red lines for you and your sponsor/board? Options: Leverage / total net debt covenant, Interest coverage, Restricted payments / dividends, Negative pledge / lien covenants, Change of control provisions, Incurrence covenants
• Where are you prepared to show flexibility if it meaningfully improves syndication or pricing? Options: Pricing, Maturity, Amortization schedule, Limited covenant step‑downs, Collateral package, Other
• Do regulatory, tax, sponsor LPA, or other external rules create non‑negotiable limitations we must model from day one? Options: Yes — regulatory constraints, Yes — tax constraints, Yes — sponsor / LPA constraints, No, Unsure — need to confirm
• Who must approve compromises on covenants or structural terms (internal and external), and how quickly can they act? Options: Internal Legal, External Counsel / Sponsor Counsel, CFO / Treasurer, Board / Finance Committee, Sponsor / LPs, Other
• If we proposed a covenant trade that stretched your flexibility, how would you prefer we present that trade to stakeholders (format and decision criteria)?

Timing, Windows, and the Price of Delay

• If every day of delay meaningfully widened pricing or risk, what is the maximum timeline slip you can absorb before the deal becomes unacceptable? Options: <3 days, 3–7 days, 1–2 weeks, >2 weeks
• What rate‑lock window would you need to feel confident we can protect priced terms? Options: 7+ days, 4–6 days, 2–3 days, Same‑day / intraday
• Are there fixed external deadlines we must meet (maturities, bid deadlines, covenant cure dates)? Please specify which. Options: Debt maturity, Acquisition bid deadline, Covenant cure period, Rating agency review date, Other
• Which internal processes typically slow approvals (board scheduling, sponsor consent, legal review) that we should plan around? Options: Board meetings / calendar, Sponsor approvals, Internal legal review, External counsel turnaround, Treasury sign‑off, Other
• When time is compressed, how do you want us to prioritize trade‑offs between time, price, and lender quality? Options: Time > Quality > Price, Price > Quality > Time, Quality > Price > Time, Equal priority across all three
• What contingency plans do you already have if the primary execution path fails (e.g., bridge financing, alternative lenders)?

Getting Comfortable with Execution

• What would make you feel confident handing lead coordination to an external advisor rather than relying on your incumbent bank?
• Which advisory deliverables would you value most from a lead advisor? Options: Detailed credit memo and rating agency prep, Capital structure modeling and sensitivity analysis, Targeted lender outreach and bookbuilding, Negotiation leadership, Documentation and closing coordination, Post‑close covenant monitoring setup
• How actively do you want to be involved in lender selection and outreach? Options: Hands‑on (approve every lender), Review and approve shortlist, High‑level oversight, Minimal involvement — delegate to advisor
• What communication cadence would keep you informed without creating noise? Options: Daily milestone updates, Twice weekly, Weekly, Ad‑hoc as milestones hit
• What specific artifacts (data room folders, model outputs, legal templates) would you need from us during diligence to feel comfortable?
• Are there past advisor relationships or experiences (positive or negative) that would shape how we should approach you? Options: Yes — positive experiences, Yes — negative experiences, Neutral / none, Unsure
• What would be a decisive go/no‑go milestone for you during engagement (e.g., X% soft coverage, a lead investor term‑sheet)?

Final Signals: Costs, Commitments, and Next Steps

• What would make you decide to award an exclusive mandate to an advisor today?
• Which commercial and timeline terms would you require before granting exclusivity? Options: Defined timelines and milestones, Cap on advisory fees / fee structure, Defined exclusivity period, Performance milestones / clawbacks, Communication and reporting protocol
• Before signing an engagement, what level of lender outreach or soft‑commitment would you expect to see? Options: Preliminary indicative interest from top banks, Demonstrable coverage % of target amount, At least one lead investor soft‑commitment, Detailed lead term‑sheet
• What are your expectations for conflict disclosures, prior relationships, and reference checks from the advisor?
• Which immediate next step would you prefer if you decide to proceed? Options: Introductory strategy workshop, Preliminary credit memo and modeling, Board / sponsor briefing, Draft engagement letter / mandate, Other
• Any final unspoken constraints, political dynamics, or stakeholder sensitivities we should know about before we design an execution plan?