Quick Introductions — Who’s in the Room?

• Who are the primary decision-makers we should be talking to right now (roles and names)? Options: Founder / CEO, Co-founder / Partner, Spouse / Family member, CFO / Controller, Outside Attorney, CPA / Tax Advisor, Family Office / Investor, Board / Advisory Board, Other
• Which single person usually has the final say on a transaction like this? Options: Founder / CEO, Co-founder, Spouse/Family, Board Chair, Investor Representative, Consensus of leadership team, Other
• How aligned are those decision-makers today on exploring an outside partner? Options: Completely aligned, Mostly aligned with a few reservations, Divided roughly 50/50, Mostly opposed but open to discussion, Undecided / unknown
• Tell us briefly about any informal influencers or gatekeepers who shape the founder’s decision-making.
• How do decisions typically get finalized in your business—Founder veto, consensus, advisor recommendation, or another pattern? Options: Founder veto, Consensus of leadership, Advisor-driven, Investor/Board approval, Other

If This Fell Apart Tomorrow, Why Would That Be?

• What’s the single reason you might choose NOT to pursue a partner like us right now?
• How long has this concern been influencing your thinking? Options: Less than 1 month, 1–6 months, 6–24 months, 2+ years, New consideration
• If that issue were resolved, how would it change your appetite to proceed? Options: Would proceed immediately, Would proceed but with caution, Would need more time to decide, Still unlikely to proceed
• Who else needs to be convinced to remove this barrier, and what will convince them?
• Have you walked away from or paused a prior opportunity for the same reason? What happened?

Timeline Pressure — How Fast and How Flexible?

• If everything had to close in 30 days, what would break in your business?
• What is your ideal timing for a transaction? Options: Immediately / within 30 days, 1–3 months, 3–6 months, 6–12 months, 12+ months
• Are there external deadlines driving urgency (tax, contracts, seasonal revenue, debt covenants)? Select all that apply. Options: Tax year / events, Customer contract renewal/consent, Lender covenants / refinancings, Regulatory deadline, Personal timing (retirement, relocation), None of the above, Other
• Which internal milestones must occur before you could comfortably sign?
• What would accelerate or decelerate your decision-making timeline? Options: Clarity on valuation, Clear retention plan for team, Simple governance post-close, Tax/liquidity certainty, Competing offers, Personal events, Other

What Do You Really Need From a Partner?

• If you could sell only parts of your business and keep the rest, what would you absolutely not part with?
• Which outcomes are true must-haves for you (pick up to three)? Options: Guaranteed employee protections, Meaningful equity rollover, Founder leadership role post-close, Preserve brand/operational independence, Immediate liquidity at close, Clear growth/bolt-on playbook, Strong cultural fit
• Which of those must-haves feels non-negotiable, and why?
• How would you define success at 12 months and at 36 months post-close?
• What trade-offs on valuation or timing would you accept to secure the must-haves you selected? Options: Significant valuation concession, Small concession, Prefer full valuation no concession, Open to earn-out / milestone structure

Money & Rollover — Are You Betting on the Second Bite?

• How important is material equity rollover for your personal and professional goals? Options: Essential — I want meaningful future upside, Important but not essential, Nice-to-have, Not important
• What percentage of equity would you consider meaningful to retain influence and upside? Options: 0% (full cash), 1–5%, 6–15%, 16–30%, 31%+
• Would you consider a phased rollover tied to performance milestones or time-based vesting? Options: Yes — prefer milestone-based, Yes — prefer time-based, No — prefer immediate rollover, Unsure / need advisor input
• How do you feel about earn-outs, contingent payouts, or milestone-triggered liquidity? Options: Comfortable, Open with clear metrics, Prefer to avoid, Need advisor input
• Who should review potential rollover structures with us (which advisors or internal leaders)? Options: Outside attorney, CPA / tax advisor, Wealth/family office, Board/advisor, CFO, Other

Who Signs Off Outside Your Office?

• Who, outside your company, could stop this deal cold?
• Which external advisors will you consult before deciding (select all that apply)? Options: Outside attorney, CPA / tax advisor, Personal financial advisor, Family office, Existing investors, Lender, Other
• Are there regulatory approvals, industry consents, or customer contract consents required to close? Options: Yes — regulatory, Yes — customer consents, Yes — lender consents, No, Unsure
• Do any existing investors, owners, or lenders have veto or consent rights we should know about? Options: Yes — investors, Yes — lenders, Yes — other, No
• How long do you expect external approval cycles to take (best / likely / worst case)?

Deal Boundary Lines — What’s Off Limits?

• What’s one thing you will absolutely not accept in a deal—even for a higher price?
• Which employee protections do you require immediately post-close (select all that apply)? Options: No layoffs for X months, Preserve health benefits, Retention bonuses for key staff, Preserve union/contract terms, Other
• How important is preserving brand identity or operational independence? Options: Critical, Important but negotiable, Minor concern, Not important
• What governance roles would you insist on post-close (board seat, observer, advisory role)? Options: Board seat, Board observer, Advisory role, No formal role — informal involvement only, Other
• Are there categories of customers, contracts, or geographies you want carved out or handled specially?

Culture & People — Who Will Carry the Story Forward?

• Imagine your team hears the news today that an outside partner is buying the company—what is the emotional reaction you expect?
• Which employee groups are mission-critical to retain (select all that apply)? Options: Sales leadership, Operations / field teams, Key technical staff, Finance / accounting, HR / People Ops, Customer success, Other
• What retention levers have worked for you before (bonuses, equity, titles, culture commitments)? Options: Retention bonuses, Rollover equity, Promotion / new title, Contractual protections, Cultural commitments, Other
• How much say do you want in first-line leadership and key hires after close? Options: Direct hiring authority, Advisory input only, No role in hires, Depends on role
• How would you prefer employee and customer communications to be handled during the transition? Options: Founder-led announcement, Joint announcement with buyer, Phased communications, Buyer-led, Other

Decision Confidence — How Do You Want This Process Run?

• What is the single thing we could do in this process that would make you say 'yes' confidently?
• What frequency and format of updates would keep your decision-makers comfortable? Options: Weekly written update, Weekly call, Bi-weekly, Ad-hoc as needed, Dashboard access only
• Who should be our primary point of contact on your side for deal logistics? Options: Founder / CEO, CFO, COO, Outside counsel, Deal lead / advisor, Other
• What level of transparency on valuation methodology and playbook do you expect early in the process? Options: Full transparency early, High-level first, detail after LOI, Only necessary info, Need advisor input
• Are there specific documents or metrics you need from us early to build confidence (e.g., case studies, references, sample term sheets)? Options: Case studies / references, Sample term sheet, Integration playbook, Financial model / assumptions, Other

Signing the Dotted Line — Next Steps & Small Commitments

• If we left this conversation without a clear next step, what would make you regret the missed opportunity?
• What small, low-risk step would you be willing to take in the next week to move this forward? Options: Sign NDA / confidentiality agreement, Share high-level financials, Introduce advisors, Schedule a deeper meeting, Provide customer references
• Who needs to be included in that next step from your side? Options: Founder / CEO, CFO, Outside counsel, CPA / tax advisor, Spouse / family, Other
• Do you prefer a mutual NDA before we share detailed financials and diligence lists? Options: Yes — mutual NDA, Yes — buyer NDA only, No — not necessary at this stage, Unsure / need advisor input
• Which materials would be most helpful for you to receive next from us (choose all that apply)? Options: Intro deck and strategy overview, Sample term sheet, Data request checklist, Integration playbook, Founder references / portfolio company intros, Other

Quick Snapshot — Tell Us Who You Are

• What is the company name, headquarters location (city, state), and primary website?
• Which best describes your current ownership and decision-making group? Options: Sole founder, Founders + spouse/partner, Founder + external investors (minority), Family-owned, Other
• Select your approximate trailing twelve months (TTM) revenue range. Options: $10–25M, $25–50M, $50–100M, $100–250M, >$250M, Prefer not to say
• How many total employees (full-time equivalents) across all locations? Options: <25, 25–50, 51–100, 101–250, 251–500, >500
• Who is the primary contact for an initial commercial and operational conversation (name, role, email)?
• Which of these statements best describes why you’re exploring a partner now? Options: Need capital to grow, Lack management depth to scale, Seeking liquidity/partial exit, Desire geographic expansion, Succession planning, Other

Where the Business Really Lives

• What would you say is the single biggest thing keeping the business from reliably scaling to the next level? Options: Access to capital, Leadership bandwidth, Operational systems, Sales/marketing capability, M&A execution, Other
• Please break down your revenue by major service line or product today (percentages — list each line and %).
• How much of revenue is recurring or subscription-like versus transactional or one-off? Options: >75% recurring, 50–75% recurring, 25–49% recurring, <25% recurring, Not tracked
• Which geography or business unit is currently highest-growth, and why do you think that is?
• Describe any seasonality or cyclical patterns that materially affect cashflow or staffing.
• Are there business lines you’d consider divesting or that are clearly non-core? Options: Yes — one or more, Not currently, Unsure

Who Keeps the Lights On?

• If the founder stepped back tomorrow, what would visibly break in the next 90 days?
• Please map the senior leadership roles you have today (title and name) and note any open or unstaffed critical roles.
• Which functions are centralized vs. decentralized (finance, HR, operations, sales, IT)? Options: All centralized, Mostly centralized, Mixed, Mostly decentralized, All decentralized
• How dependent is the business on particular individuals (e.g., founder, salesperson, ops lead)? Please name roles and describe the dependency.
• How do you currently recruit and develop mid-senior level managers? Options: Internal promotions, External hires via agencies, Executive search, We struggle to hire, Other
• What HR or people systems do you use for payroll, performance, and compliance? Options: ADP/Paylocity, BambooHR/Workday, Gusto/QuickBooks Payroll, Custom spreadsheets, Other

What Your Customers Can't Live Without

• What’s the riskiest assumption you make about your customers that, if wrong, would change the business materially?
• How concentrated is your revenue among top customers (approx % from top 5 and top 10)? Options: Top 5 >50%, Top 5 30–50%, Top 5 <30%, We do not track
• Which customer segments are most profitable and why (by vertical, size, contract type)?
• What is your typical sales cycle length by offering (weeks/months) and main acquisition channels? Options: <1 month, 1–3 months, 3–6 months, >6 months, Varies by segment
• What’s your average customer retention or churn rate over the past 24 months (if tracked)? Options: <5% annual churn, 5–15%, 16–30%, >30%, Not tracked
• Are there long-term contracts, exclusivity agreements, or vendor/customer terms we should know about? Options: Yes — material contracts, Yes — minor contracts, No, Unsure

Money Under the Hood — Financial Controls & Drivers

• How confident are you that past financials reflect the true, repeatable earning power of the business? Options: Very confident, Generally confident with exceptions, Questionable in areas, Not confident
• Which accounting systems and processes do you use (ERP, payroll, invoicing)? Options: NetSuite, QuickBooks, Sage/Peachtree, Custom ERPs, Spreadsheets/Manual
• Have you completed audited or reviewed financial statements in the last 3 years? Options: Audited, Reviewed, Unaudited but prepared, No formal statements
• Describe any recurring one-time adjustments, owner-related expenses, or accounting practices that materially affect EBITDA.
• What is the typical working capital profile (cash conversion days, receivables days, inventory or prepaid service liabilities)?
• Are there material off-balance-sheet liabilities, leases, tax exposures, or contingent obligations? Options: Yes — material, Yes — manageable, No, Unsure

Culture, What Matters Most, and Who Stays

• If we asked your employees what they value most about working here, what do you think they'd say—and what worries them?
• How would you describe the core cultural norms that guide day-to-day decisions? Options: Customer-first, Execution-focused, Family/relational, Technical/expert-driven, Other
• What are your annual voluntary attrition and involuntary turnover rates for frontline and leadership roles? Options: <5%, 5–15%, 16–30%, >30%, Not tracked
• Do you have formal employee engagement or pulse surveys? If yes, what are the recurring themes? Options: Regular surveys — mostly positive, Regular surveys — mixed, Ad hoc feedback, No formal surveys
• Have you used equity, rollover, or incentive programs to retain senior staff? Please describe any existing plans. Options: Rollover equity for founders, LTIP/bonus plans, Stock/options for key hires, None, Other
• What cultural attributes would you most want preserved after a partnership, and why?

M&A Readiness — Where the Gaps Are

• What’s the single biggest reason your business has not already completed bolt-on acquisitions or scaled via M&A? Options: Lack of capital, No sourcing capability, Integration capability, Leadership bandwidth, Fear of cultural dilution, Other
• Have you previously bought or sold businesses? Describe outcomes and lessons learned.
• How complete is a data room today (financials, customer contracts, HR files, IP, compliance)? Options: Investor-ready (very complete), Mostly complete, Partial, Minimal or none
• Which systems would be hardest to integrate with a platform operating model (CRM, scheduling, billing, back-office)? Options: CRM/field ops, Billing/AR, Scheduling/dispatch, Payroll/HRIS, Proprietary tech, None
• Do you have third-party vendor contracts or customer consents that could impede a change in ownership? Options: Yes — some require consent, Yes — difficult to transfer, No, Unsure
• Are there known integration friction points (licensing, union rules, state regs) we should prioritize?

Risks, Unknowns, and Potential Deal-Breakers

• What issue, if discovered in diligence, would most likely cause you to walk away from a partnership?
• Are there pending legal or regulatory matters, claims, or investigations involving the company? Options: Material pending matters, Minor matters, None, Unsure
• Do you have any key supplier or vendor dependencies that could disrupt operations if changed? Options: Yes — single supplier risk, Yes — concentrated vendors, No, Unsure
• Have there been any recent cybersecurity incidents or data breaches? If yes, describe impact and remediation. Options: Yes — material, Yes — minor, No, Unsure
• What insurance coverages do you maintain for professional liability, cyber, and general business interruption?

If We Partnered — What Would Real Success Look Like?

• If you could guarantee one outcome from a partnership in five years, what would you choose: faster growth, better margins, expanded geographic reach, or founder continuity—and why? Options: Faster growth, Better margins, Broader geography, Founder continuity/role, Other
• How important is maintaining brand identity and local autonomy post-partnership (scale 1–5)? Options: 1 — Not important, 2, 3, 4, 5 — Extremely important
• What level of founder rollover equity feels acceptable versus required for you to stay engaged long-term? Options: None — prefer cash out, <25% rollover, 25–50% rollover, >50% rollover, Undecided
• Which operational improvements would unlock the most value quickly (select up to three)? Options: Standardized ops playbook, Centralized finance/HR, Sales enablement/CRM, Tech modernization, Field hiring/comp structure, Other
• Realistically, how involved do you want to be after a transaction across these areas: strategic advisor, day-to-day ops, regional leader, board member, or fully exited? Options: Strategic advisor, Semi-active (quarterly), Regional/operator role, Board with voting rights, Fully exited
• What questions or concerns would you want addressed up-front to feel comfortable continuing conversations?

Practical Next Steps — What We’ll Need From You

• Which documents can you provide in the next 7–14 days to accelerate discussions (financials, tax returns, key contracts)? Options: Last 3 years financials, YTD management P&L, Customer contracts, Employee roster and comp, Insurance and leases, All of the above
• Who will be the internal point person for diligence and information requests?
• Are there timing constraints or deadlines we should be aware of (funding needs, contract renewals, or fundraising windows)? Options: Yes — specific deadlines, Some timing sensitivity, No immediate timing constraints
• Would you prefer a staged information request (high level then detailed) or a single consolidated diligence push? Options: Staged approach, Consolidated push, Open to either
• Is anyone besides listed decision-makers authorized to sign NDAs or share legal financial documents? Options: Yes — name listed, No, Unsure

Quick Snapshot: Where We Stand Right Now

• How would you describe your readiness to begin integration and deployment activities in the next 30–90 days? Options: Ready to start within 30 days, Ready but need minor prep (30–60 days), Significant prep required (60–90+ days), Unsure / need assessment
• What is your current target or expected close date (or earliest realistic go-live window)? Options: Within 2 weeks, Within 30 days, 30–60 days, 60–90 days, More than 90 days, TBD
• Who will be the primary integration lead from your side (name, title, best contact) and who are the two other internal stakeholders we should loop in immediately?
• Which systems currently hold your core operational data (select all that apply)? Options: ERP / Finance system, CRM / Sales system, Scheduling / Ops software, Payroll / HRIS, Customer-facing portals, Medical/EHR systems, Proprietary/internal apps, Other
• Are there any active legal, regulatory, or investor holds that could delay signing or closing? Options: Yes, No, Unknown / needs verification

Before We Flip the Switch—What Could Stop Us?

• If we had to go-live tomorrow, what single technical, legal, or people-related obstacle would surprise you most and prevent it?
• Which specific documents or access permissions are still incomplete in your data room and who owns each item?
• Which of the following data sets are not yet exportable or easily shareable for integration work? Options: General ledger / charts of accounts, Customer master & contracts, Payroll & benefits data, Inventory / equipment records, Service delivery / scheduling records, None — all exportable, Unsure
• How confident are you in the accuracy and cleanliness of the data we will inherit (customer IDs, billing history, employee headcount)? Options: High — vetted and clean, Moderate — work needed, Low — significant cleanup required, Unknown
• Who holds the administrative credentials and how will we obtain secure access (SSO, shared vault, staged handover)? Options: IT admin, Founder/CEO, External MSP/vendor, HR/Payroll admin, Not yet identified

Who Do We Need to Keep—And What Happens If They Leave?

• Which three roles or individuals would cause immediate operational or revenue disruption if they resigned within 60 days of close?
• Do you have active retention agreements, deferred compensation, or upcoming equity events for key employees? Options: Yes — documented, Planned but not documented, No, Not sure
• Which retention tools would feel acceptable to you and your leadership team (select all that apply)? Options: Short-term cash bonuses, Time-based equity rollovers, Title/role commitments, New performance-based incentives, Non-compete adjustments, Other
• How do employees currently describe the company culture and what language would you want preserved in early communications to staff?
• Are there any collective bargaining agreements, pending grievances, or known HR disputes we should factor into retention planning? Options: Yes, No, Unsure — need review

Your Tech Stack—Will It Cooperate?

• If your systems couldn’t exchange data with a central shared-services platform for 60 days, which operational area would break first? Options: Billing & cash collection, Scheduling & service delivery, Payroll & HR, Customer support, Regulatory reporting, Other
• For each core system (ERP, CRM, HRIS, scheduling, billing), please list the vendor, version, hosting model (cloud/on-prem), and whether API access exists.
• What is the current integration maturity for those systems? Options: Standard APIs available — production-ready, APIs exist but need development, Exports only (CSV/XML) — manual processes, No practical export path — custom work required, Unknown
• Are there third-party vendors or custom code we must coordinate with for data transfers (e.g., EHR integrators, industry-specific vendors)? If so, who are they and what are their SLAs?
• How do you currently handle backups, disaster recovery, and access auditing for systems that contain customer or payroll data? Options: Managed by internal IT, Managed by external MSP, Basic backups only, No formal process, Unsure

Paperwork, Permits, and the Things That Stop a Close

• Which existing contracts or permits explicitly require third-party or customer consent on change of control that could delay operations? Options: Major customer contracts, Key supplier/vendor contracts, Real estate leases, Government licenses/permits, Insurance policies, None identified, Unsure / need review
• Are there material pending regulatory filings, inspections, or approvals tied to your ability to operate post-close? Options: Yes — details attached, No, Possibly — need counsel input, Unsure
• Who is your outside counsel and who will manage legal handoffs and consents during the pre-closing period?
• Do any leases, real estate agreements, or third-party vendor terms include assignment fees, cure rights, or accelerated obligations on change of control? Options: Yes — several, Yes — a few, No, Unsure — need review
• Are there insurance, bonding, or certification renewals due in the next 6–12 months that the integration team should budget for early? Options: Yes — list attached, No, Unsure

Will Customers Notice—and How Will They React?

• Which customer segment (or specific customers) would notice a change in ownership first and how might that impact retention or contracts? Options: Large enterprise accounts, Mid-market recurring customers, Small/local accounts, Regulated customers, No single segment stands out, Other
• Do any top customers have change-of-control clauses, explicit approval requirements, or service guarantees that could trigger renegotiation? Options: Yes — top customers affected, Some customers may be affected, No, Unsure — need contract review
• What is your current customer communication plan for ownership change, and who from your team is comfortable leading customer outreach? Options: We have a draft plan, We need help drafting, No plan yet, Prefer the buyer to lead communications
• Are there key accounts with single points of failure (a single PM, tech, or rep) whose transition would risk immediate revenue loss? Options: Yes — list provided, A few, No
• How would customers describe the things they value most about your company (price, responsiveness, local relationships, quality, other)? Options: Price, Responsiveness/service, Local relationships, Quality of work, Specialized expertise, Other

The First 90 Days—What Would Real Success Look Like?

• If we are accountable for day-one stabilization, what is the single highest-impact outcome you expect within the first 30 days?
• Which of the following milestones must be completed within 90 days to consider the deployment successful? Options: Payroll continuity verified, Billing & collections transitioned, Key systems integrated and reconciled, Top 3 retention agreements executed, Regulatory or license transfers complete, Customer communication executed
• Who will be the milestone owners on your side for payroll, IT, HR, commercial accounts, and legal (name + role for each)?
• What are reasonable go/no-go criteria for each major milestone (how will we know it’s done)?
• Are there budgeted or one-time costs we should expect to fund in the first 90 days (systems migration, vendor fees, retention payouts)? Please estimate amounts or ranges if known.

Hidden Costs, Unknowns, and The Things That Keep Founders Up at Night

• What expense or liability has surprised you most in prior transitions (tax, legacy payroll, vendor claims, lease penalties) and why?
• Are there open tax positions, audits, or deferred liabilities that require special handling, and who is your tax advisor? Options: Yes — details attached, No, Unsure — need review
• Do you foresee any one-time operational costs tied to integration (e.g., rebranding, new software licenses, training) that haven’t been budgeted? Options: Yes — list amounts, Possibly — unsure, No
• Have you previously run a divestiture, acquisition, or major systems migration? What surprised you most about the cost or timeline?
• What contingency or buffer would make you feel comfortable about financial and operational surprises during the first 90 days? Options: Cash reserve (amount), Contingent vendor credits, Phased handover, Other

Getting to Know Your Story

• In one short paragraph, tell us who you are, what your business does, and why you’re exploring a partnership now.
• What is your company’s approximate annual revenue today? Options: <$10M, $10M–$25M, $25M–$50M, $50M–$100M, >$100M
• Which vertical best describes your primary business? Options: Healthcare services, Facility maintenance, Financial services, Business services, Other
• How many physical locations or operating regions do you currently have? Options: 1–5, 6–20, 21–50, 51–100, 100+
• Who is on the short list of people making this decision inside your circle (founder, spouse, partner, advisors)? Please name roles rather than individuals if you prefer.
• Roughly when would you like a transaction to close if everything aligns? Options: Next 3 months, 3–6 months, 6–12 months, 12–18 months, No firm timeline

If Growth Is the Promise, What’s Been Getting in the Way?

• What one belief about your growth limits would you want us to challenge right away?
• Which of the following have materially constrained growth in the last 24 months? Options: Access to capital, Leadership bandwidth, Sales capacity, Technology limitations, Regulatory barriers, Customer concentration, Other
• How has revenue and EBITDA trended over the past 3 years (growth, flat, declining)? Options: Strong growth, Moderate growth, Flat, Declining
• Who are your top 3 customers by revenue share and how dependent are you on them?
• What attempts have you already made to solve the main constraint, and how long have you been working on those fixes?
• If nothing changes in the next 12–24 months, what is the most likely downside scenario for the business?

Who Actually Holds the Keys — And What Keeps Them Up at Night?

• When you picture making a decision on a partnership, what would make someone in your inner circle say 'this is unsafe'?
• Which stakeholders must sign off before you can move forward? Options: Board/advisors, Founder/owner, Spouse/partner, Financial advisor, Legal counsel, Key investor
• How involved are external advisors (financial, legal, tax) in the evaluation process today? Options: Actively advising and available, Advising on request, Not yet engaged, We plan to engage soon
• What are the founder’s non-negotiables that would prevent a deal from happening (e.g., brand preservation, certain employee protections, specific governance terms)?
• How do the family or partner dynamics influence the timeline and willingness to change?

What Would Success Feel Like — Not Just on Paper?

• If we delivered everything on your wish list, what would you and your team be celebrating one year after close?
• Which measurable outcomes matter most to you post-close? Options: Revenue growth %, EBITDA margin increase, Location expansion, Customer retention rate, Employee retention, Founder liquidity
• How much meaningful equity would you realistically want to retain after a rollover to feel aligned long-term? Options: None (full liquidity), <10%, 10–25%, 25–50%, >50%
• What role would you prefer after close and how hands-on would you want to be? Options: CEO/operator, Chair/strategic advisor, Part-time advisor, Exit immediately post-close, Other
• Beyond financials, what personal goals (lifestyle, reputation, legacy, family security) does a successful outcome need to address for you?

How Will the People and Culture Survive — Or Thrive?

• Is the company known internally for one dominant leadership style or culture trait that we must preserve? Describe it.
• Who are the 5 people you could not lose without harming operations or customer relationships?
• Have you used retention or rollover equity packages before to keep leaders post-close? How did they work? Options: Yes — successful, Yes — mixed results, No, but open to it, No, not open
• What percentage of your workforce is hourly vs. salaried, and which group do you worry about most losing during transition? Options: Mostly hourly, Mostly salaried, Even split, Unsure
• How would employees likely describe their confidence in leadership and future company direction (high/medium/low)? Options: High, Medium, Low, Unsure

The Numbers That Reveal Readiness

• Please select the best description of your accounting and reporting maturity. Options: Robust, audited financials, Reviewed by CPA but not audited, Tax-prep only financials, QuickBooks/simple books
• What was your most recent 12-month revenue and adjusted EBITDA (ballpark if exact not available)?
• Which financial controls are currently in place (check all that apply)? Options: Monthly close process, Budgeting and forecasting, AR/AP approval workflows, Internal audits, None of the above
• Do you maintain customer-level profitability data or a product/service-level margin view today? Options: Yes, customer-level, Yes, product/service-level, Both, No
• How predictable is your cash flow seasonally and what months are most challenging?

Integration Reality Check — What Will Break First?

• If we had to integrate your business into a platform over the first 12 months, what single operational issue would slow us down most?
• Which systems are core to delivery and will need to be integrated (HR, payroll, CRM, ERP, scheduling)? Options: HRIS/payroll, CRM/sales, ERP/finance, Scheduling/field ops, Proprietary systems, None of the above
• Do you have vendor or customer contracts with change-of-control clauses that could be triggered by a sale? Options: Yes, No, Unsure
• What regulatory or licensing requirements must be preserved during transfer (state licenses, HIPAA, bonding, insurance)?
• How quickly can you provide clean, exportable operational and HR data if requested? Options: Immediately, Within 2 weeks, Within 1–2 months, Longer / uncertain

Deal Mechanics — What Would You Actually Accept?

• If value creation is driven over time, how comfortable are you with earnouts vs. higher upfront cash? Options: Prefer upfront cash, Balanced earnout + cash, Prefer earnout-heavy, Open to discussion
• What is the minimum rollover percentage that would make you feel aligned post-close? Options: 0%, 5–10%, 10–25%, 25–50%, >50%
• Which governance arrangements would you find acceptable (board seat, advisory role, no seat)? Options: Board seat, Advisory role, No formal seat, Time-limited role
• What employee protections are non-negotiable (e.g., no immediate layoffs, retention bonuses, maintained benefits)?
• Are there tax, estate, or personal liquidity needs that require specific structuring? Options: Yes — requires special structure, Possibly — needs review, No special needs

Red Flags, Skeletons, and Gaps — Tell Us Before They Surprise Everyone

• Are there pending or threatened legal claims, audits, or investigations we should know about? Options: Yes — details to follow, No, Unsure
• Have there been material tax disputes, historic payroll liabilities, or past ERISA exposure? Options: Yes, No, Unsure
• Are there environmental, licensing, or compliance issues in any operating region that could block integration? Options: Yes, No, Some concerns
• Do you have any undisclosed related-party transactions, founder loans, or vendor arrangements tied to owners? Options: Yes, No, Unsure
• If any of the answers above are 'Yes', briefly describe the issue, status, and estimated financial exposure.

Stories That Matter — Past M&A Experience and Lessons

• Have you been involved in a sale, merger, or acquisition before? Tell us what worked and what didn’t.
• If you’ve sold or partnered before, what was the single biggest emotional surprise after closing?
• What would you want us to promise and actually deliver to avoid repeating past mistakes?
• How long have you been thinking about an exit or partnership as a strategic option? Options: Months, 1–2 years, 3–5 years, More than 5 years

How Comfortable Are You Sharing the Paperwork — Practical Readiness

• How complete is a data-room-style package today (financials, contracts, HR files, insurance)? Options: Mostly complete, Partially complete, Only basic docs, Not started
• Who on your team will be the day-to-day point person for diligence and integration coordination?
• Are there timing windows (seasonality, large contracts, regulatory renewals) we must avoid when scheduling diligence or closing? Options: Yes — specify, No
• What level of granular data (customer-level, job-level, location-level) are you comfortable sharing early in diligence? Options: Full granular data, Aggregated data only, Limited samples only, Unsure

Commitment, Concerns, and Next Steps

• On a scale from 1–10, how committed are you to pursuing a partnership if alignment is clear? Options: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10
• What is the single biggest concern that would make you pause right now?
• Who else should we talk to next (name, role), and can you introduce us?
• Realistically, what date or milestone should we use as a next-decision checkpoint? Options: Within 2 weeks, Within 1 month, Within 2–3 months, No set date
• What would you need from us in the next 7 days to feel this conversation is moving in the right direction?