Opening: Who's Driving the Decision?

• Who is the final decision-maker for this raise? Options: Founder-CEO, Founder + Board approval, CEO with Board sign-off, CEO + CFO, Board control / Board chair, Other
• Who will be the day-to-day point person for our advisory team and investor outreach? Options: Founder-CEO, CFO, Head of Finance, Chief of Staff, External counsel, Other
• How involved do you expect the board to be in shaping valuation, investor selection, and timing? Options: Hands-off / tactical only, Advisory but decisive, Actively involved in investor selection, Will demand approval for final terms, Unsure
• Have you recently run a comparable fundraise? Who led negotiations last time and what role should they play now?
• Which internal stakeholders must be consulted before a signature (name roles or teams)? Options: Founder(s), Board members, CFO/Finance, Legal counsel, Head of People, Head of Revenue/Sales, Other
• Who on your team we should treat as the single source of truth for cap table and legal documents? Options: CFO, Head of Finance, External counsel, Founder-CEO, Not defined yet

Who Holds the Keys?

• Could any board member or current investor realistically veto the deal path you prefer—and if so, who? Options: Yes, No, Possibly / Unsure
• List your board members and briefly characterize their fundraising posture (supportive / neutral / skeptical).
• Which board members have demonstrable fundraising experience or investor networks we should engage? Options: Board chair, Relevant sector expert, Current investor with track record, No experienced board members, Other
• Have any past board discussions led to delayed or reshaped rounds (examples and outcomes)?
• What does your board prioritize most when evaluating a round—valuation, speed, strategic investor, governance, or something else? Options: Valuation, Speed to close, Strategic investor fit, Governance protections, Minimize dilution, Future control/true-up mechanisms, Other
• If board alignment is fragile, how would you prefer we surface and resolve disagreements during process? Options: Pre-authorized escalation path, Weekly alignment calls, Board chair + CEO decision, Vote-based, Not sure / need advice

The Runway & Deadline Pressure

• If the round slips by 4–6 weeks, what exactly breaks—hiring, burn runway, a contract, or something else?
• How many months of runway do you currently have (assuming current burn)? Options: <3 months, 3–6 months, 6–9 months, 9–12 months, 12–18 months, >18 months
• What is your target close window (when do you realistically need funds in bank)? Options: 2–4 weeks, 4–8 weeks, 8–12 weeks, 3+ months, Flexible / no hard deadline
• Are there near-term product, revenue, or customer milestones tied to this timing? If so, describe and include dates.
• If timing compresses, which contingency would you consider: bridge from existing investors, convertible note, cost reductions, or other? Options: Bridge from existing investors, Convertible note / SAFEs, Aggressive cost cuts / hiring freeze, Revenue acceleration programs, None feasible / must close, Other
• Are there external timing constraints we should know about (customer renewals, regulatory deadlines, competitor events)?

Success Signals That Don't Lie

• Which single metric would make an institutional investor write the check today? Options: ARR and growth trajectory, Net Dollar Retention (NDR), Gross margin profile, Burn multiple / unit economics, Customer concentration / enterprise traction, Other
• Select the metrics investors at your stage typically care about (pick all that apply). Options: ARR, ARR Growth rate (YoY/YoYQoQ), Net Dollar Retention (NDR), Gross margin, Burn multiple, Free cash flow runway, CAC / LTV, Customer concentration, Other
• Provide current concrete numbers: ARR, ARR growth rate (QoQ or YoY), NDR, gross margin, and burn multiple.
• Which customer evidence accelerates conviction for you—expansion revenue, referenceable logos, signed pilots, or predictable pipeline? Options: Expansion revenue, Referenceable enterprise logos, Multi-year contracts, High-quality pipeline / inbound demand, Customer referrals / case studies, Other
• Which single metric gap worries you most when talking to investors and why?

Deal Must-Haves and Red Lines

• What term or clause in a term sheet would make you walk away immediately?
• What maximum dilution (approximate % of company) are you willing to accept in this round? Options: <10%, 10–20%, 20–30%, 30–40%, >40%, Not sure / want advice
• Which governance outcomes are non-negotiable for you (e.g., board composition, protective provisions, anti-dilution type)? Options: Founder control / veto on key items, Limit on investor board seats, No participating liquidation preference, No full ratchet anti-dilution, Standard protective provisions only, Other
• Do you require investors to provide operational support (e.g., go-to-market, hiring, customer intros) as a condition of lead selection? Options: Yes — required, Nice-to-have, No preference, Prefer passive financial investors
• What minimum post-money valuation or price-per-share threshold would you view as unacceptable to go below?
• Are there investor profiles you explicitly want to avoid (e.g., activist, sector-agnostic, overly controlling, public-market focused)? List and explain.

Past Rounds Tell a Story

• What in your last round’s terms or process is most likely to reappear as a negotiation landmine now?
• Summarize prior terms we should know: last valuation, liquidation preferences, anti-dilution mechanics, option pool status.
• Which investors from prior rounds would you like us to re-engage, and which (if any) should be excluded? Please name and state preference.
• What lessons from past diligence slowdowns should we prioritize fixing before outreach?
• Do you currently have outstanding legal, IP, cap-table, or employee documentation issues that could surface during diligence? Options: Option pool / grants not approved, IP assignment gaps, Cap table discrepancies, Pending litigation or claims, Customer contract concerns, No known issues, Other
• Do you have references (customers, prior investors, advisors) willing to speak on short notice? If yes, who and what will they highlight?

Decision Rhythm & Communications

• If three term sheets land in the same week, can your leadership team align and respond within 48 hours? Options: Yes, No, Maybe with pre-work, Unsure
• Who must be included in an internal term-sheet review call (names/roles)? Options: Founder-CEO, CFO, Board chair, Lead investor (ad hoc), Legal counsel, Head of Revenue/COO, Other
• What is your preferred cadence and format for advisor updates during outreach (email digest, weekly calls, dashboard access)? Options: Daily email digest, 2–3x/week calls, Weekly call + dashboard, Biweekly updates, Ad hoc for material events
• How quickly can legal documents be reviewed and routed for signature (typical turnaround time)? Options: <24 hours, 1–3 days, 3–7 days, >1 week, Unsure
• Are there blackout periods coming up (product launches, board meetings, investor roadshows, holidays) where fundraising should pause?
• Which communication channel do you prefer for time-sensitive alerts (phone/SMS, email, Slack, other)? Options: Phone / SMS, Email, Slack / Teams, Project platform updates only, Other

Reality Check: What’s Most Likely to Stall Us?

• What is the single most likely thing to derail this fundraise in the next 60 days?
• Which of the following blockers are likely to surface (select all that apply)? Options: Data room gaps, Model hygiene / financial inconsistencies, Cap table / option issues, Key customer churn or concentration, Board disagreement, Legal / IP concerns, Market/sector downturn, None of the above, Other
• Which of the selected blockers can you commit to resolving within two weeks? Specify who will own each fix.
• Which external factors could meaningfully slow investor interest (market sentiment, high-profile competitor news, regulatory change)? Options: Market/sector volatility, Competitor fundraise or product launch, Macro funding slowdown, Regulatory or policy risk, No meaningful external constraints, Other
• What concrete pre-work would lower the likelihood of stalls (data room items, model cleanup, legal fixes)? List top three priorities.
• Are you ready to grant us access to board materials, cap table, and core diligence docs to validate readiness? Options: Yes – full access, Yes – limited access only, Not yet, need to prepare, Need to discuss with board

Commitment: Locking the Roles, Timeline, and Escalation Plan

• Can we commit to a shared decision plan now that locks in roles, timeline, and escalation rules if disagreements arise? Options: Yes – ready to commit, Need to modify the plan, Not ready to commit
• Propose the first three milestones for this engagement (e.g., model cleanup, investor list, board alignment) and who owns each.
• Which success criteria should we use to decide when to pause outreach and re-evaluate strategy (e.g., no term sheets in X weeks, runway falling below Y months)?
• Who is authorized to sign off on commercial terms and who must be looped in for governance items? Options: Founder-CEO, Founder + Board chair, CEO + CFO, Board approval required, Other
• Would you like us to prepare a short one-page alignment memo for the board summarizing agreed roles, timeline, and escalation rules? Options: Yes – prepare memo, Maybe – want to review first, No – not necessary
• Please capture any final concerns or conditions we should be aware of before we begin outreach.

Opening: The Snapshot That Moves the Clock

• How many months of runway do you currently have? Options: <3 months, 3–6 months, 6–9 months, 9–12 months, 12–18 months, 18+ months
• Who is driving the decision to start this raise on a day‑to‑day basis? Options: Founder/CEO, CFO/Head of Finance, Board member, Acting fundraising lead, External advisor, Other
• What is the rough headline target for this round (raise size and target pre‑money)?
• When is the latest possible date you must have funds in the bank to avoid cutting growth plans? Options: Within 30 days, 30–60 days, 61–90 days, 91–120 days, 120+ days
• How confident are you in the runway and timing numbers you just shared? Options: Very confident, Somewhat confident, Unsure — needs validation, Not confident

If the Round Slows, What Breaks First?

• If this process slips 8–12 weeks, what’s the first thing inside the company that will stop or materially slow? Options: Hiring freeze, Marketing slowdown, Product roadmap delays, Customer support cuts, Sales slowdown, Other
• Which internal constraint becomes most acute as runway tightens, and how would that show up operationally?
• How would a prolonged close change the morale or decision-making dynamics between founders and the board?
• Have you run into a stalled round before? Briefly tell us what broke the momentum and what you learned from it.
• What contingency actions are you prepared to execute if we miss the target close date? Options: Pause hiring, Reduce spend by X%, Seek bridge financing, Activate strategic partner, Other

Numbers That Make Investors Lean In — Or Lean Away

• Which single financial metric do you believe will define investor appetite and valuation for your company right now? Options: ARR/Growth, Net Dollar Retention (NDR), Gross Margin, Burn Multiple, Unit Economics (LTV/CAC), Other
• Please provide current ARR, ARR 12 months ago, and the trailing three‑month growth rate (paste numbers).
• What is your current net dollar retention (percentage) and what are the primary drivers of that figure?
• What is your current gross margin and any major levers that will change it over the next 12 months?
• Which range best describes your burn multiple (net burn / net new ARR)? Options: <0.5, 0.5–1.0, 1.0–2.0, 2.0–3.0, 3.0+
• How investor-ready is your financial model and forecast (e.g., audited, investor-reviewed, internal only)? Options: Audited/GAAP, Reviewed by advisor/auditor, Investor-friendly but unaudited, Internal model — needs cleanup

Terms You’re Carrying — Which Ones Help vs Hurt

• Which existing investor term or cap-table feature do you fear will meaningfully reduce buyer competition or valuation? Options: Large liquidation preferences, Participating preferred, Aggressive anti-dilution, ROFR/ROFO, Major pro-rata claims, Other
• Describe any current liquidation preferences, participation rights, ratchets, or protective provisions that investors would see in the cap table.
• Do any outstanding SAFEs, notes, or convertible instruments convert at terms that could materially change the pre-money? Options: Yes — material, Yes — minor, No, Not sure
• Which investor-side governance rights currently exist (board seats, vetoes, information rights) that could affect a new lead investor? Options: Board seat(s), Veto rights, Observer rights, Special approval thresholds, None of the above
• Which of these existing terms are you open to revisiting during this round? Options: Liquidation preference, Anti-dilution, Board composition, Pro-rata allocations, Side letters, None — not open

Risks Investors Will Spotlight — And How You’ll Answer Them

• What is the single risk you expect investors to surface first that could force a price cut or lengthy diligence? Options: Customer concentration, Revenue recognition, Churn, IP/tech risk, Regulatory/compliance, Other
• Identify the top three diligence red flags (briefly) and explain why each could slow or derail a deal.
• What percentage of ARR comes from your top 5 customers today? Options: 0–10%, 11–25%, 26–50%, 51–75%, 75%+
• Are there any active legal, tax, IP, or compliance issues that would surface in a standard diligence review? Options: Material issue — active, Minor issue — manageable, No issues, Unsure — need to check
• For each risk above, what concrete evidence or mitigant can you deliver quickly to reassure investors?
• Have you had past diligence adjustments (accounting restatements, customer churn disclosures) that investors referenced? If yes, summarize. Options: Yes — significant, Yes — minor, No

What Would Make Investors Pull Forward a Check?

• What one near-term change (metric, contract, or evidence) would most increase the chance an investor converts curiosity into a term sheet in weeks?
• Are there near-term customer wins, partnerships, or contract signings that would materially change the forecast if closed in the next 30–60 days? Options: Yes — multiple, Yes — one meaningful, Maybe — in progress, No
• How much incremental runway (months) or revenue uplift would you estimate is required to change the target valuation band? Options: None, 1–3 months / small uplift, 3–6 months / moderate uplift, 6+ months / material uplift
• Would you consider offering governance concessions (e.g., expanded board, observer terms) to accelerate close or improve valuation? How comfortable are you with that trade? Options: Very comfortable, Somewhat comfortable, Reluctant, Not comfortable
• Which types of investors would you prioritize for a fast-close scenario (lead with strategic, growth equity, traditional VC, crossover)? Options: Strategic, Growth equity, Traditional VC, Crossover, Angel syndicate

Decisions You’ll Need to Make — Who Signs and When

• If a term sheet arrives that protects founder economics but requires a board sign-off, who has final approval authority and under what conditions? Options: Founder unilaterally, Founder + CEO, Board approval required, Special committee, Investor consent required
• Map the internal approval steps required to accept a lead term sheet (people and expected timing).
• When handling multiple term sheets, which process do you prefer: structured auction, staged negotiation, or single-lead bilateral? Options: Structured auction, Staged negotiation, Single-lead bilateral, Unsure — want advice
• What are your non-negotiables for governance and economics (list the top 3 that you will not concede)?
• If closing faster requires giving some economic or control concessions, which axis are you more willing to trade on? Options: Valuation (take less $/share), Governance (board seats/rights), Pro-rata/structure, Deal timing (warranties/escrows)
• What is your target timeline from signed term sheet to cash in bank? Options: <2 weeks, 2–4 weeks, 4–6 weeks, 6–8 weeks, 8+ weeks

Commitment & Next Steps — What Would Help Us Move Faster?

• What would make you feel comfortable committing to a compressed 4–12 week process starting today?
• Who will be the single point of contact for diligence and investor communication on your team? Options: CEO/Founder, CFO/Head of Finance, Fundraising lead, General counsel, External advisor, Other
• Which documents are ready for a data room today (select all that apply)? Options: Latest 3 P&Ls/Balance sheets, Cap table and SAFEs, Customer contracts, Top 10 customer references, IP documents, Compliance certificates, None ready
• What outstanding items must be resolved before we begin outreach (legal, audit, referenceable contracts, etc.)? List and prioritize.
• What is the first measurable milestone you’d like us to deliver in the next 7–14 days? Options: Investor map with priorities, Cleaned financial model, Pitch deck revision, Initial outreach list, Diligence checklist
• How would you prefer we run status and decisions (weekly syncs, shared dashboard, ad‑hoc calls, or email summaries)? Options: Weekly live sync, Shared dashboard with async updates, Ad-hoc calls as needed, Email summaries only, Combination

Quick Live Check — Where Are We Right Now?

• On a scale, how confident are you that your company could survive an investor diligence sprint starting next week? Options: Very confident, Confident, Somewhat confident, Not confident
• How many months of runway do you have today (best estimate)? Options: <3 months, 3–6 months, 6–9 months, 9–12 months, >12 months
• Who currently owns the data room and financial model updates on your team? Options: CEO / Founder, CFO / Head of Finance, FP&A / Controller, External advisor, No single owner
• When was the data room last audited or re-organized? Options: Within 1 week, Within 1 month, Within 3 months, Within 6 months, Longer / never
• If you had to describe your single biggest worry about diligence in one sentence, what would it be?

What Would Stop an Investor Cold?

• If an experienced investor scanned your data room for 90 seconds, what would make them say 'we need to slow this down'?
• Which of the following documents would you expect investors to request first? Options: Cap table and option pool history, Latest 3 P&L / balance / cash flow, Waterfall and liquidation scenarios, Top customer contracts, Product / IP documentation, Compliance certificates (SOC2, GDPR)
• Have you ever had diligence previously uncover an issue that changed deal economics or timing? Options: Yes — materially, Yes — minor impact, No
• If yes, briefly describe what was found and how long it took to remediate.
• How would you feel if a lead investor asked for a full audit of your revenue recognition policies? Options: Comfortable — we’re clean, We’d need to prepare but can deliver, Concerned — some gaps exist, Alarmed — major issues

Which Numbers Will Get Picked Apart?

• Which core metric in your model do you believe an analyst will most aggressively challenge—and why?
• Select the metrics we should expect written follow-ups on. Options: ARR / TTM revenue, Net Dollar Retention (NDR), Gross margin by product, Customer acquisition cost (CAC), Burn multiple, Bookings vs recognized revenue, Churn / cohort retention
• Do you have reconciliations between GAAP numbers, internal dashboards, and investor-facing spreadsheets? Options: Yes — documented and recent, Partial — some reconciliations, No — not reconciled
• How frequently are forecasts and model assumptions updated? Options: Weekly, Biweekly, Monthly, Quarterly, Ad-hoc/rarely
• Share an example of a recent forecast assumption that changed materially—what happened and how did you explain it to stakeholders?

The Data Room: Welcome Center or a Maze?

• How often in the last 12 months did your team have to dig for a 'missing' contract or statement? Options: Never, Once, 2–3 times, Monthly, Weekly
• Which best describes your current data room organization? Options: Indexed with summary document and version control, Indexed but no summaries, Partial organization — key files only, Ad-hoc folders with inconsistent naming, No formal data room
• Do you maintain a single master index or checklist that maps every document to investor questions? Options: Yes — fully mapped, Partial mapping, No — but plan to, No — not available
• Which access controls and tracking do you have in place for the room? Options: Time-limited links, Watermarked downloads, Viewer logs, Tiered access levels, No controls
• If an investor asked for a redline of your top five customer contracts, how quickly could you provide it? Options: <24 hours, 1–3 days, 4–7 days, >7 days, We don’t track redlines

Model Hygiene — Will It Survive the Scrutiny?

• If we handed your financial model to an investor analyst, what would break first?
• Which of these model controls do you have implemented? Options: Assumptions tab with documented sources, Version history with change log, Sensitivity tables, Scenario outputs (best/base/worst), Audit formulas / error checks
• Who runs model reviews and how long do they take? Options: Internal finance weekly, Internal finance ad-hoc, External advisor periodically, No regular reviews
• Do you publish a bridge showing movement from last reported financials to your current forecast? Options: Yes — detailed bridge, High-level bridge, No bridge available
• Describe any manual workarounds or spreadsheet hacks that would need cleaning before investor review.

Material Risks — Which Ones Could End the Conversation?

• Which unresolved risk would most likely cause investors to walk if left unaddressed? Options: Customer concentration, IP ownership questions, Pending litigation, Regulatory / compliance exposure, Key-person dependency, Accounting restatement risk
• For the top risk you selected, how long has it existed and what remediation (if any) is underway?
• How transparent do you plan to be with investors about these risks in early diligence? Options: Fully transparent with context, Selective transparency, Wait until later stages, Undecided
• Have you prepared mitigation evidence (legal memos, remediation plans, insurance) for material risks? Options: Yes — ready, Partially ready, No — need to prepare
• Which internal owner is accountable for each top-3 risk?

Narrative vs Evidence — Does the Story Match the Files?

• Is there any part of your investor narrative that sounds strong in the deck but can’t be proven in the data room? Options: Yes — multiple sections, Yes — a single claim, No — fully proven
• Which narrative claims require the most supporting evidence? Options: Growth runway and expansion plan, Customer retention and NDR, Unit economics and CAC payback, Product roadmap and IP protections, Market leadership / comps
• Are customer references and case studies mapped and ready to share on short notice? Options: Yes — multiple references, A couple ready, None prepared
• Do you have a one-page audit trail that ties each headline claim to a specific document or table in the room? Options: Yes, In progress, No
• Share an example of a deck claim you’d want us to validate first before investor outreach.

Compression Test — Could We Run a 4-Week Diligence?

• If we had to compress diligence to four weeks to hit a closing window, what would snap first—people, documents, or processes? Options: People (availability), Documents (missing items), Processes (review cadence), Other
• Which documents would be gating items for a compressed timeline? Options: Top customer contracts, Cap table and option history, Audited financials or financial statements, Key hire offer letters and equity docs, IP assignment agreements
• Who are the three internal or external owners we need immediate access to during diligence?
• What is a realistic number of business days to produce a missing gating document? Options: <24 hours, 1–3 days, 4–7 days, >7 days
• How comfortable is your leadership with daily or twice-weekly diligence check-ins during an accelerated process? Options: Very comfortable, Somewhat comfortable, Reluctant but possible, Not comfortable

Commitments & Next Steps — Who Does What and When?

• If we move to outreach this week, what concrete changes will you commit to in the first 14 days to improve diligence readiness?
• Which of these would you prioritize to shore up before a lead investor review? Options: Cap table cleanup, Customer contract summaries, Model reconciliation and sensitivity, Legal memos on material issues, Reference pack and case studies
• Who will be the single point of contact for investor requests during diligence? Options: CEO / Founder, CFO / Head of Finance, Legal counsel, External advisor, Rotate by topic
• What is the earliest date you can guarantee dedicated time from owners for diligence (calendar date)?
• Finally, what would success look like for you at the end of a 6-week diligence period?

Quick Grounding: Where You are Right Now

• What role are you filling in this process? Options: Founder / CEO, CFO / Head of Finance, CRO / Head of GTM, Board member / Advisor, Other
• How would you best describe the current status of your raise? Options: Not started (planning), Preparing materials (deck/model), In-market (meetings ongoing), Received term sheets, Paused/indefinite
• How many months of runway do you have today? Options: <3 months, 3–6 months, 6–12 months, 12–18 months, >18 months
• What round are you targeting and approximately how much capital do you intend to raise? Options: Pre-Seed / Seed, Series A, Series B, Growth / Later stage, Convertible / Bridge
• If you can, enter the target raise amount or range (USD).
• Who on your team will be the primary day-to-day contact for an advisor? Options: Founder / CEO, CFO, Head of Finance, Head of Growth / CRO, External counsel, Other

What If the Clock Wins?

• If you haven’t closed a round in 90 days, what is the single most likely outcome for the company? Options: Staff reductions, Hiring freeze, Delay or cancel product roadmap, Seek bridge on worse terms, Run out of cash
• Which operational or financial metric would first force a material change to strategy if the raise slips? Options: ARR growth, Net dollar retention (NDR), Burn multiple / runway, Gross margin, Customer acquisition payback, Other
• How often have you modelled the ‘downside’ scenario for delayed funding and how actionable are those plans? Options: Modeled and actionable, Modeled but not executable, High-level only, Not modeled
• Have you already had internal conversations about which planes you would cut or which hires you’d pause if the round slips? Options: Yes — clear plan, Yes — vague ideas, Not yet, Prefer not to answer
• Describe one concrete milestone that must be hit in the next 60–90 days to avoid a crisis (revenue, contract, product, etc.).
• Who on the executive team feels most stressed by the timing, and how is that showing up in day-to-day decisions?

Who Really Holds the Keys?

• If the board had to sign off on the round tomorrow, how confident are you that you would get unanimous support? Options: Very confident, Some concerns with one or two members, Divided views likely, Not confident
• List the decision-makers who must be aligned (name and role).
• Which stakeholder priorities are non-negotiable for the board or lead investors? Options: Valuation, Speed to close, Governance structure, Founder control/board seats, Signal investors / brand, Other
• Are there any existing investor relationships or commitments that will materially affect syndicate formation? Options: Yes — committed lead, Yes — verbal interest, No existing commitments, Prefer not to say
• Who is empowered to sign the engagement letters and final documents on behalf of the company? Options: CEO, Board Chair, CFO, Combination / depends on counsel, Other
• Are there known internal conflicts or differing expectations among the founders or board that we should be aware of? Options: Yes — material, Yes — minor, No, Prefer not to answer

Valuation vs Dilution: Where’s Your Line?

• If taking more time produced a 25% higher valuation but the business needed the cash now, which would you choose? Options: Wait for higher valuation, Raise quickly at lower valuation, Split the raise (bridge + main), Unsure
• What percentage dilution is an absolute ceiling for you in this round? Options: <10%, 10–20%, 20–30%, 30–40%, >40%
• Which term-sheet clauses worry you most from a founder-protection perspective? Options: Liquidation preferences, Anti-dilution (full ratchet), Control / protective provisions, Board composition, Participation rights, Other
• Have there been prior rounds or convertible notes with features that create complexity (participating preferred, MFN, valuation caps)? If so, list them.
• What trade-offs are you willing to make to secure a strategic investor who adds operational value? Options: More dilution, Worse governance terms, Faster close preferred, Prefer pure financial investors, Depends on investor
• Describe one past negotiation you feel you handled well and one you wish you had handled differently.

What Story Will Investors Believe?

• What single narrative do you expect will convince investors this is the right multiple to apply?
• Which metrics will investors anchor to when valuing you? (pick up to three) Options: ARR growth rate, Net dollar retention (NDR), Gross margin, CAC payback, LTV:CAC, Revenue concentration, Other
• How clean is the financial model and can you produce scenario-level outputs quickly for investor questions? Options: Fully modelled and stress-tested, Mostly modelled but needs cleanup, Basic model only, No reliable model
• How complete is your data room against investor expectations (financials, cap table, contracts, IP, customer references)? Options: Complete, Mostly complete, Partial, Minimal
• Which customers or proof points will most reliably close investor concerns about churn, retention, or growth?
• What’s the most sensitive data point you expect investors to probe deeply (margins, churn pockets, concentration, legal)? Options: Margins, Churn pockets, Customer concentration, Legal/IP, Revenue recognition

What Could Break This Round?

• What is the single negotiation dynamic you fear most when term sheets land? Options: Unwilling lead investor, Aggressive control terms, Split syndicate causing delays, Surprising diligence findings, Price collapse late in process
• Have you identified any cap-table or legal issues that could slow or derail diligence? Options: Yes — material, Yes — minor, No known issues, Unsure / need review
• How comfortable are you pacing multiple competing term sheets (weighing speed vs price) without losing leverage? Options: Very comfortable, Some experience but not confident, No experience, Prefer to avoid
• What internal time windows (board meetings, investor availability, product launches) will constrain closing dates?
• Who will be the internal lead for diligence responses and how quickly can they turn around sensitive requests? Options: CFO / Head of Finance, CEO, Head of Legal, Dedicated data room lead, Not yet assigned
• List any external advisors (legal, accounting, previous bankers) you plan to involve and their stage of readiness.

If This Round Is a Home Run, What Changes?

• Beyond the cash, what is the single most important outcome you want from the right investor? Options: Strategic GTM help, Follow-on capital, Credibility / signal, Operational support, Board expertise, Other
• How do you plan to allocate proceeds across hiring, product, go-to-market, and runway extension (approximate percentages)?
• What milestones in the next 12 months will prove the raise was successful (revenue targets, metrics, launches)?
• What governance or reporting cadence would you prefer after close (monthly updates, quarterly board, board observer)? Options: Monthly investor updates, Quarterly board meetings, Board + monthly reports, Quarterly updates only, Other
• Which introductions or operational support from an investor would have immediate measurable impact?
• How would you measure whether this advisor’s involvement contributed meaningfully to that home-run outcome? Options: Multiple competitive term sheets, Close within target timeline, Improved governance terms, Strategic investor secured, Reduced founder dilution

How Would You Like Us to Show Up?

• What’s the most painful part of fundraising you would hand off immediately if you could? Options: Investor outreach and scheduling, Term negotiation, Model and diligence prep, Crafting the narrative, Managing investor expectations
• Which advisory model do you prefer? Options: Full-service (we run process end-to-end), Advisory only (coach and support), Hybrid (we handle outreach + you lead meetings), Unsure — want to discuss
• What budget or fee structure are you expecting for an advisory engagement? Options: Fixed fee, Success fee at close, Hybrid retainer + success fee, Equity-based / roll into deal, Not yet discussed
• How soon do you expect to decide on engaging an advisor? Options: Immediately, Within 2 weeks, Within a month, Later / flexible
• What would be the top three success signals you’d use to evaluate an advisor after 30 days?
• Is there anything else you want us to know right now that would change how we prioritize support?