Tell Me About the Deal That's Keeping You Up

• What is the project name, address, and a one‑sentence description?
• Who are the core sponsor stakeholders (name and role) and who will be our day‑to‑day contact?
• What is the property type and unit mix? Options: Multifamily, Office, Industrial, Retail, Hospitality, Mixed‑Use, Other
• What are the key project metrics today — total development cost, current/capitalized equity, and the estimated financing need (dollar amounts)?
• What stage is the project at today? Options: Acquisition pending, Predevelopment/entitlements, Permitted, Under construction, Stabilization/lease‑up, Refinance/recap
• What internal or external deadlines are non‑negotiable (purchase option expirations, construction milestones, investor capital calls)? Please include dates if available.

What Would Happen If You Missed the Next Deadline?

• If financing isn’t secured by your next critical date, what are the realistic consequences for the deal and the sponsor?
• How severe would the financial or reputational impact be—minor delay, meaningful cost overrun, loss of option, or deal collapse? Options: Minor delay/manageable, Moderate cost/time impact, Significant financial loss, Deal at risk of collapse
• How long has this deadline been a pressure point, and what tradeoffs have you already made to try to protect it?
• Which of these matters most right now: speed of close, size of proceeds, cost (rate/fees), certainty of funding, or preserving sponsor control? Options: Speed of close, Size of proceeds, Cost (rate/fees), Certainty of funding, Preserving sponsor control
• On a scale from 'calm' to 'urgent', how would you describe the emotional pressure in the sponsor team around this financing? Options: Calm/planful, Some urgency, High stress/urgent

If You Could Design the Capital Stack, What Would It Look Like?

• If you had a blank sheet, what mix of debt and equity would you prefer (first choice)? Options: Construction loan + permanent, Construction + mezzanine, Bridge to permanent, Preferred equity/JV, All‑equity, Other
• What maximum leverage (LTV or LTC) do you consider acceptable for this asset type? Options: <60%, 60–70%, 70–80%, 80–90%
• Which instruments are you open to including in the stack? Options: Construction loan, Permanent loan, Mezzanine debt, Preferred equity, Joint venture equity, Bridge loan, CMBS
• What is the minimum sponsor equity you can commit today (dollar amount or % of total cost)?
• Which term tradeoffs would you accept to gain speed or certainty—higher fee, partial recourse, shorter term, or higher interest reserve? Options: Higher fee, Partial/limited recourse, Shorter loan term, Higher interest reserve, None of the above
• What target net proceeds or sponsor cash‑on‑closing do you need to make the deal viable?

Where Lenders Have Said No — Tell Me Why

• When lenders have declined past deals, what was the most common reason you were given? Options: Market comps/values, Sponsor experience, Cost‑overrun risk, Entitlement risk, Borrower leverage, Loan structure/recourse, Other
• Tell me about a recent financing attempt that failed—what specifically did lenders cite, and how long ago was it?
• How have you tried to mitigate those lender concerns so far (guarantors, higher equity, pre‑leases, contractor letters)?
• Which lender types have shown the most interest — regional bank, national bank, debt fund, insurance, CMBS, private equity — and which have been quick to move? Options: Regional bank, National bank, Debt fund, Insurance company, CMBS conduit, Private equity / opportunistic funds
• Would you consider non‑traditional solutions (stretched mezzanine, seller carryback, hybrid preferred equity) if traditional lenders decline? Options: Yes, Maybe, No

Who Decides and What Keeps Them Up at Night?

• Who are the decision‑makers for financing approval (investor LPs, board, CEO, committee), and what are their primary concerns?
• What are the non‑negotiable investor or LP constraints (return hurdles, leverage caps, approval lead time)?
• How fast can the sponsor legally commit to an exclusive engagement or term sheet (days/weeks)? Options: Within 24 hours, 2–7 days, 1–2 weeks, Longer than 2 weeks
• What internal approvals or materials are typically required before you sign (board packets, pro forma, legal review, partner consent)? Options: Board/Investor approval, Updated financial model, Legal review, Partner/GP consent, Guarantor approvals, Other
• How do you prefer to receive updates during placement—daily call, weekly written memo, milestone dashboard, or as‑needed? Options: Daily call, Weekly written memo, Milestone dashboard, As‑needed/critical only

What Would a Flawless Close Look Like to You?

• Describe the ideal timeline from term sheet to funding for this transaction—what's acceptable and what would be a crisis?
• Which closing elements cause the most delays for you—title, environmental, contractor draws, survey, lender underwriting, or legal negotiation? Options: Title issues, Environmental reports, Contractor/draw mechanics, Survey/ALTA, Lender underwriting timeline, Loan documentation negotiation
• What draw mechanics and reporting cadence do you need post‑close to manage construction (monthly draws, % retention, certificate of completion)? Options: Monthly draws, Bi‑monthly draws, Retention %, Milestone draws, Other
• Which covenants or recourse structures would you never accept, and which are negotiable?
• After funding, what success metrics should we track together (budget variance, construction schedule, occupancy, DSCR targets)? Options: Budget variance, Construction schedule milestones, Occupancy rates, DSCR/coverage ratios, Rent‐up velocity, Other

What Would Make Working With an Advisor Worthwhile?

• If you could hire an advisor to guarantee one thing, what single outcome would you demand (speed, certainty, best economics, or creative structure)? Options: Speed of execution, Certainty of close, Optimal pricing/terms, Creative capital structuring
• Which advisor behaviors build trust for you—transparent brokered lender lists, real‑time model updates, direct lender introductions, or on‑site coordination? Options: Transparent lender list, Real‑time model updates, Direct lender introductions, On‑site coordination, Regular executive summaries
• How do you prefer fee alignment—success fee only, retainer + success fee, or hourly/advisory plus success fee? Options: Success fee only, Retainer + success fee, Hourly/advisory + success fee, Other
• What level of exclusivity would you be comfortable granting an advisor to win priority lender access? Options: Full exclusivity for a period, Limited exclusivity for specific lender types, No exclusivity
• What would make you recommend an advisor to other sponsors—specific examples of added value or moments that matter?
• Are you ready to proceed with a structured market sounding now, and what materials can you share immediately (model, pro forma, draws schedule, contractor AIA)? Options: Yes — materials ready, Yes — need 1–2 days to compile, Not yet — need >1 week, Unsure

• Financing Strategy Kickoff & Current-State Review
• Capital-Stack Scenario Workshop (Diagnosis → Proof)
• Lender & Investor Market Match — Sources, Terms, Probability
• Tradeoffs, Terms & Path-to-Close Confirmation (Decision Meeting)
• Risk, Contingency & Execution Readiness

• Authorize advisor to commence market outreach according to the agreed plan.
• Sponsor: Confirm any non-negotiable covenants or structural constraints (recourse limits, ownership thresholds).
• Advisor: Update the model with any assumption changes agreed during the workshop.
• Recap Preferred Scenario(s) and Acceptance Criteria
• Create a prioritized, actionable target-lender list mapped to each preferred scenario.
• Set realistic term expectations and execution timelines for outreach.
• Agree outreach sequencing and exclusivity stance to maximize execution certainty.
• Identify any underwriting deliverables that must be prepared immediately.
• Advisor: Deliver a target-lender packet (contact, expected terms, probability, required docs) for each shortlisted lender.
• Sponsor: Provide any required organizational documents or prior lender history needed for outreach.
• Advisor: Draft outreach templates and a proposed outreach timeline for sponsor approval.
• Recap Market Feedback & Key Term Ranges
• Finalize and document the single preferred path to close and negotiation priorities.
• Agree explicit acceptance criteria that will be used to judge inbound term-sheets.
• Establish fee structure and advisor economic alignment for the mandate.
• Introductions & Meeting Objectives
• Sponsor: Sign-off on the acceptance criteria and outreach authorization.
• Advisor: Begin outreach to prioritized lenders and circulate initial info pack.
• Advisor: Prepare a negotiation playbook and key-message brief for lender conversations.
• Confirmed Path & Timeline Recap
• Establish an actionable contingency plan with clear triggers and alternative sources.
• Assign execution owners and a communication protocol for underwriting and draw management.
• Validate that the team can respond to common shocks without derailing the path to close.
• Create a monitoring cadence to surface risks early and keep stakeholders aligned.
• Advisor: Produce a contingency playbook with trigger thresholds and backup lender contacts.
• Sponsor: Nominate the single-point decision-maker for contingency activation and provide delegated authority details.
• Advisor: Establish the monitoring dashboard and schedule the standing update cadence.
• All participants confirm a single-sentence current-state diagnosis.
• Sponsor and advisor agree on quantified consequences of failing to secure timely financing.
• Clear, measurable success criteria for acceptable financing outcomes are documented.
• Data gaps and required model adjustments for the next meeting are identified.
• Sponsor: Deliver revised financial model and updated schedule with itemized budgets within 48 hours.
• Advisor: Produce one-sentence current-state statement and consequence summary to circulate before the workshop.
• Advisor: Prepare baseline scenario runs (bank, mezz, preferred equity) using the updated model.
• Recap of Current State & Success Criteria
• Demonstrate which capital-stack scenarios meet the measurable success criteria and which fail under stress tests.
• Surface and document explicit tradeoffs (cost vs. speed vs. covenants vs. dilution).
• Gain sponsor validation on a ranked set of 1–2 preferred scenarios to take to market.
• Identify any remaining model assumptions to lock before lender outreach.
• Advisor: Produce a scenario comparison memo with sensitivity outputs and recommended top scenarios.
• Fee & Economics Tradeoffs
• Lender Universe Mapping by Product
• Scenario A: Bank Construction → Permanent
• Top Risks & Impact Assessment
• Current-State Snapshot (one sentence)
• Scenario B: Debt Fund / Mezzanine + Preferred Equity
• Term Expectations by Lender Type
• Contingency Options & Trigger Thresholds
• Key Constraints & Deadlines
• Recourse, Covenant & Structural Negotiation Priorities
• Scenario C: JV Equity or Bridge-then-Permanent Hybrid
• Probability & Timeline Assessment
• Draw Mechanics, Milestones & Timing to Close
• Roles, Communication Protocols & Decision Rights
• Project Metrics Review (proof data)
• Pre-Underwriting Readiness Check
• Scenario Comparison Dashboard
• Consequence Quantification
• Validation Exercise: Simulated Shock
• Acceptance Criteria Checklist Review

• Build full underwriting financial model
• Prepare lender/investor offering memorandum
• Solicit and distribute lender term sheets
• Negotiate and finalize loan term sheets
• Structure and place mezzanine debt
• Structure and place preferred equity
• Place joint-venture equity and negotiate JV terms
• Assemble and deliver lender due-diligence package
• Administer construction draw disbursements
• Manage lender inspections and payment certifications
• Procure title, survey, and environmental reports
• Manage loan closing and funding execution
• Negotiate intercreditor and subordination agreements
• Execute construction-to-permanent loan conversions

Build full underwriting financial model

• What property type and project phase should the model support? Options: Multifamily, Office, Industrial, Retail, Hospitality, Mixed-use, Land / entitlement, Other
• Which financing scenarios must be modeled (select all that apply)? Options: Construction loan only, Permanent loan only, Construction-to-perm, Bridge, Mezzanine, Preferred equity, JV equity, Refinance
• What model outputs and deliverables are required? Options: Pro forma cash flows, Sources & uses, Debt service schedule, Investor waterfalls, IRR / equity returns, Sensitivity & stress tests, Draw schedule, Other
• What level of detail and assumptions do you expect (e.g., monthly construction budget, unit-level rent roll)? Options: High: monthly construction + unit-level, Medium: quarterly construction + building-level, Low: summary-level
• Who will provide base inputs (sponsor underwriting, GC budget, market comps)? Options: Sponsor/Developer, GC/PM, Advisor to build assumptions, Lender-provided assumptions, Other
• What is your required delivery timeline for the completed model? Options: < 3 business days, 3-7 business days, 1-2 weeks, 2+ weeks

Prepare lender/investor offering memorandum

• What audience(s) will the OM target? Options: Regional banks, Debt funds, Insurance companies, Mezzanine funds, Private equity / JV partners, All of the above
• Which sections should the OM include? Options: Executive summary, Market & comps, Financial model summary, Borrower track record, Site & entitlements, Risk mitigation, Legal/ownership structure
• Are there branding or confidentiality requirements (NDA, logo, co-branding)? Options: Yes - NDA required, Yes - co-branding required, No specific requirements
• Do you need tailored lender-specific versions or a single general OM? Options: Single OM, Tailored lender versions, Hybrid (core OM + lender appendix)
• What format and files do you require for distribution? Options: PDF (print-ready), Editable PowerPoint/Word, Secure portal link, Data room upload only
• What is the target delivery date for the initial OM draft? Options: < 3 business days, 3-7 business days, 1-2 weeks, 2+ weeks

Solicit and distribute lender term sheets

• Which lender channels should we solicit (select all that apply)? Options: Regional/commercial banks, National banks, Debt funds, Insurance companies, CMBS conduits, Credit unions, Other
• What information should accompany term sheet solicitations? Options: OM + model, Executive summary only, Data room link, Pre-qualified sponsor package
• Do you have a target timeline for receiving term sheets? Options: < 1 week, 1-2 weeks, 2-3 weeks, Flexible
• How many competing term sheets would indicate sufficient market testing? Options: 1-2, 3-5, 6+
• Who should be copied/receiving distributed term sheets within your team?
• Do you require confidentiality or tracking controls on distributed term sheets? Options: Yes - watermark & tracking, Yes - NDAs only, No additional controls

Negotiate and finalize loan term sheets

• Which term sheet items are highest priority for negotiation? Options: Rate/fees, Loan-to-cost or LTV, Amortization/term, Recourse, Covenants, Prepayment/exit terms
• Do you have recourse preferences to guide negotiation? Options: Full recourse, Limited / partial recourse, Non-recourse with carve-outs, Sponsor prefers no recourse
• Are there fee structures you will accept (placement/success fees, origination points)? Options: Standard placement fee, Success-based only, Split fees with lender, Other
• Who has final approval authority to accept a negotiated term sheet? Options: Managing Principal, CFO, Investment Committee, Other
• What is the allowable negotiation window before you require escalation? Options: 48 hours, 3-5 days, 1+ week
• Do you require a term-sheet comparison matrix for decisioning? Options: Yes, No

Structure and place mezzanine debt

• Is mezzanine debt required in the target capital stack? Options: Yes - required, Maybe - depending on terms, No
• What economic and structural preferences guide mezzanine terms? Options: Preferred interest-only, PIK interest allowed, Equity kicker required (warrant/preferred), Subordinated note only
• What target sizing and leverage metrics are acceptable for mezzanine? Options: Amount ($) - free response, Target % of total capital, Target leverage metric (e.g., LTC, LTV)
• Are there sponsor covenants or restrictions the mezzanine provider must accept? Options: Yes - provide details, No
• Which investor types should we approach for mezzanine? Options: Mezz funds, Debt funds, Private credit, Family offices, Institutional
• What is the expected timeline to syndicate or place mezzanine? Options: < 2 weeks, 2-4 weeks, 1-2 months, 2+ months

Structure and place preferred equity

• Is preferred equity being considered as an alternative to mezzanine or JV equity? Options: Preferred instead of mezzanine, Preferred alongside mezzanine, Not considering
• What preferred return and liquidity features are required? Options: Fixed preferred return, Cumulative non-cumulative, Liquidation preference, Convertible to common equity
• What target sizing and ownership percentage is expected for preferred equity? Options: Amount ($) - free response, Target % of capital, Target % of equity
• Are there tax, reporting, or investor qualification constraints for preferred equity investors? Options: Yes - provide details, No
• Which investor types should we solicit for preferred equity? Options: Private equity, Family office, Institutional investors, High-net-worth individuals
• What milestone or exit conditions must be documented for preferred returns? Options: Refinance, Sale, IPO/recap, Other

Place joint-venture equity and negotiate JV terms

• Are you seeking an active operating JV partner or passive capital only? Options: Active operating partner, Passive capital partner, Flexible
• What governance and decision rights are required (board seats, vetoes)? Options: Control with sponsor, Shared governance, Investor control on key items, Other
• What preferred profit split and promote structure do you expect? Options: Standard waterfall with promote, No promote - pro rata, Custom waterfall (provide details)
• What capital contribution schedule and funding mechanics are anticipated? Options: Commitment with draws by milestone, Capital call schedule, One-time equity close
• Are there sponsor track-record or accreditation requirements for JV investors? Options: Yes - accredited only, Yes - specific track record, No
• What is the target timeline for JV placement and execution? Options: < 2 weeks, 2-4 weeks, 1-2 months, 2+ months

Assemble and deliver lender due-diligence package

• Which core documents must be included in the diligence package? Options: Financial model, OM, Borrower organizational docs, Construction contracts, Rent rolls/leases, Appraisal, Entitlements/permits
• Do you already have a data room or do we need to create one? Options: Existing data room, Create new data room, Sponsor will provide physical files
• Who will be responsible for collecting third-party reports (appraisal, environmental, survey)? Options: Sponsor, Advisor arranges & pays, Lender orders
• Are there known diligence gaps or outstanding items we should flag upfront? Options: Yes - provide details, No
• What delivery format and security controls do lenders require (e.g., direct portal access, watermarking)? Options: Secure portal access, Watermarked PDFs, Encrypted files, Other
• What is your preferred timeline to have the full diligence package ready for lenders? Options: < 1 week, 1-2 weeks, 2-4 weeks, Flexible

Administer construction draw disbursements

• Do you require the advisor to administer monthly draw requests or just coordinate lender approvals? Options: Full administration of draws, Coordinate submissions only, Sponsor handles draws
• What draw schedule granularity is needed (monthly, milestone-based, % complete)? Options: Monthly, Milestone-based, By % completion, Other
• What backup documentation will be provided for each draw (invoices, lien waivers, GC certifications)? Options: Invoices, Lien waivers, GC/PM certifications, Third-party inspection reports, Other
• Who will handle disbursement reconciliation and accounting entries? Options: Sponsor accounting, Advisor handles reconciliation, Third-party fund administrator
• Are there lender-specific draw mechanics or escrow controls we must follow? Options: Yes - provide lender requirements, No - standard mechanics
• What SLAs are required for processing draw requests to avoid payment delays? Options: 24-48 hours, 3-5 business days, 1+ week

Manage lender inspections and payment certifications

• Which inspections are anticipated (progress, final, code, environmental)? Options: Progress/construction, Final/CO, Code/compliance, Environmental, Other
• Who arranges inspections and pays for third-party inspectors? Options: Sponsor, Advisor arranges & sponsor pays, Lender orders & pays
• What documentation must inspectors produce (photos, signed certification, measurement reports)? Options: Photos, Signed certification, Measurement/QA reports, Other
• Do you require real-time inspection reporting or periodic consolidated reports? Options: Real-time individual reports, Weekly consolidated report, Monthly summary only
• Are there insurance, safety, or compliance standards the inspections must enforce? Options: Yes - provide standards, No
• What is the expected turnaround time for inspection certifications to support draws? Options: 24-48 hours, 3-5 business days, 1+ week

• Engagement Letter
• Statement of Work (SOW)
• Fee Schedule & Payment Terms
• Exclusivity / Right to Market Agreement
• Term Sheet Priorities & Negotiation Mandate
• Recourse & Covenant Profile
• Mutual Commitment to Underwriting
• Underwriting Deliverables & Document Checklist
• Authorizations & Data Release Consent
• Break Fee & Remedies
• Closing Conditions & Funding Triggers

• Funding Confirmation & Closing Outcomes
• Lessons Learned & Deal Retrospective
• Post-Close Operations & Draw Workflow Setup
• Issue Resolution & Escalation Protocol
• Future Capital Planning & Refinance Strategy

• Create and distribute an emergency contact roster and after-hours procedure.
• Required Draw Documentation
• Agree an end-to-end draw submission and approval workflow with clear SLAs.
• Assign operational owners for draw administration, inspections, and lender liaison.
• Establish the reporting package and covenant monitoring triggers to be delivered on a set cadence.
• Publish a draw submission checklist and template for sponsor and contractor use.
• Configure the shared portal (or folder/Slack channel) for draw intake and set user permissions.
• Schedule the recurring reporting dates and assign data owners for each report element.
• Common Issue Types & Examples
• Establish a clear escalation matrix and corresponsive SLAs for post-close issues.
• Agree on dispute resolution steps that minimize funding delays and construction impact.
• Introductions & Objectives
• Publish the escalation matrix and SLAs to all stakeholders and load into the shared channel.
• Create a template for issue reports that captures severity, impact, proposed remedy, and owner.
• Distribute the emergency contact roster and test the after-hours notification process.
• Current Performance vs Pro Forma
• Create a prioritized capital plan with clear triggers and timelines for refinance or recapitalization.
• Identify target lender types and a preliminary outreach timetable to achieve the desired capital outcome.
• Assign owners for scenario modeling, market-sounding, and ongoing monitoring.
• Produce a 12–36 month capital plan document with scenarios and trigger dates.
• Prepare preliminary market materials (executive summary, updated cashflow model) for lender outreach.
• Schedule quarterly capital review check-ins to monitor performance vs triggers.
• Confirm all funding transactions and reconcile actual sources & uses with the closing statement.
• Document any deviations from the executed term sheets and capture required remedial actions.
• Assign ownership and deadlines for all outstanding post-close deliverables.
• Establish the primary shared communication channel for post-close coordination.
• Distribute final closing binder and reconciled sources & uses spreadsheet to all stakeholders.
• Update the deal financial model to reflect final funding, fees, and interest commencement.
• Create a tracker for outstanding deliverables with owners and deadlines.
• Publish the chosen post-close communication channel (portal/Slack/email) and grant access.
• Timeline Recap
• Create a prioritized set of actionable improvements to reduce friction on future transactions.
• Capture specific lender and partner feedback to inform future sourcing strategies.
• Document a short post-mortem report and update internal playbooks/checklists accordingly.
• Produce a Lessons Learned report summarizing findings, root causes, and recommended changes.
• Update the deal playbook and standard checklists (due diligence, closing) with agreed improvements.
• Schedule internal training or briefing to roll out process changes to the origination and execution teams.
• Escalation Matrix
• Refinance / Permanent Financing Triggers
• Wire & Funding Confirmations
• What Worked Well
• Draw Submission & Approval Timeline
• Market & Lender Appetite Assessment
• Final Sources & Uses Reconciliation
• Roles & Responsibilities
• Response SLAs & Communication Protocol
• Pain Points & Root Cause Analysis
• Dispute Resolution & Cure Processes
• Reporting & Covenant Monitoring
• Finalized Loan/Equity Terms & Mechanics
• Lender & Partner Performance Review
• Capital Options & Scenario Planning
• Next Steps & Owner Assignments
• Prioritized Improvement Backlog
• Portal/Channel for Draws
• Emergency Contacts & After-Hours Protocol
• Outstanding Post-Close Deliverables
• Next Steps & Communication Plan