Quick Intro: Who's in the Room?

• Please list the people and roles who will have direct input on add-on acquisition decisions for this platform company.
• Which of those people will be the ultimate decision-maker on deals of this size? Options: CEO, Board Chair, CFO, M&A Lead / Head of Corporate Development, Operating Partner, Private Equity Deal Partner, Other
• Which individuals or functions typically hold veto power or require advance notice before a deal proceeds? Options: Board members, CFO/Finance, CEO, Legal/Compliance, Major customers, LPs / Investment Committee, Other
• How often do these stakeholders formally meet to evaluate potential add-ons? Options: Weekly, Bi-weekly, Monthly, Quarterly, Ad-hoc / As needed
• Who currently owns integration planning and first-100-day playbooks inside the platform team? Options: Portfolio company CEO, CFO, Dedicated Integration Lead, Platform M&A Team, External Integration Consultant, No owner yet
• Are there external parties (LPs, strategic partners, key customers) that must be informed or consulted before a transaction is announced? Options: Yes — LPs, Yes — Strategic partners, Yes — Key customers, No, Unsure

What Would Make Your Board Sleep Easier?

• If the board woke you up at 2 a.m. about this acquisition, what single question would they demand you answer immediately?
• What approval thresholds trigger full board review for this platform (e.g., deal size, leverage, multiples)? Options: >$1M, >$5M, >$10M, >$25M, Specific multiple threshold (e.g., >7x), Other / Depends
• Which board members are most likely to prioritize risk mitigation over growth, and which will push for aggressive expansion? Options: Mostly risk-averse, Mostly growth-oriented, Split evenly, Don't know / varies by person
• How does the board define 'strategic fit' for an add-on—what signals move them (revenue synergies, customer overlap, capability build, geography)? Options: Revenue synergies, Cross-sell potential, New capabilities / tech, Geographic expansion, Cost / operational synergies, Other
• Are there non-financial board priorities (ESG, regulatory posture, reputation, diversity) that could block a deal even if the numbers look good? Options: Yes — ESG concerns, Yes — Regulatory / compliance risk, Yes — Reputation / brand fit, No, Unsure
• Tell us about a past board objection to an acquisition — what was the objection and how was it resolved?

If the CEO Could Wave a Wand…

• What's the single outcome the CEO would insist on from any add-on (e.g., faster growth, margin expansion, new capability), and why? Options: Faster revenue growth, Margin expansion / cost synergies, New strategic capability, Customer base expansion, Geographic reach, Other
• Beyond that headline outcome, what are the CEO's top three measurable targets for the next 12–18 months?
• How tolerant is the CEO of short-term revenue disruptions during integration? Options: Very tolerant — long-term view, Somewhat tolerant, Low tolerance — needs stability, Zero tolerance — must maintain revenue
• What cultural signals or behaviours would most reassure the CEO that an acquired team will integrate smoothly? Options: Strong leadership commitment, Customer-centric mindset, Operational discipline, Transparent communication, Shared values, Other
• How involved does the CEO want to be in diligence and negotiations—hands-on, oversight only, or somewhere in between? Options: Hands-on (regular meetings), Periodic check-ins, High-level oversight only, Not involved
• When the CEO says 'move fast', what constraints or risks do you worry might be overlooked?

Where Does Money Say Yes or No?

• At what valuation or EBITDA multiple would your CFO say 'we can't justify this' — select the clearest threshold you have Options: < 3x EBITDA, 3–5x EBITDA, 5–7x EBITDA, 7–10x EBITDA, > 10x EBITDA, Depends on strategic rationale
• What IRR or ROI hurdle must a deal clear for sign-off? Options: > 25%, 20–25%, 15–20%, 10–15%, < 10%, No strict numeric hurdle
• Which financial levers does finance trust most to deliver projected returns (choose up to three)? Options: Cost synergies / headcount rationalization, Revenue cross-sell, Price increases, Back-office consolidation, Tax or working capital optimizations, Other
• What capital sources are available or preferred for add-ons (platform cash, committed facility, sponsor bridge, seller financing)? Options: Platform cash, Committed debt facility, Sponsor-provided capital, Seller financing / earnouts, Equity raise, Other
• Who must sign off on contingent structures like earnouts, escrow, or holdbacks? Options: CFO, CEO, Board, Private equity deal partner, Legal, Other
• Describe a time finance pushed back on a deal—what was the core concern and what resolved it?

Timeline Pressure Points — What Breaks Under Time?

• If you were forced to close an accretive add-on in 30 days, what single process or approval would most likely collapse?
• What is your typical timeline from first-screen to signed LOI? Options: < 30 days, 30–60 days, 60–90 days, 90–180 days, > 180 days
• Which approval gates are most often the bottleneck: board review, CFO modeling, legal, regulatory, customer approvals, or something else? Options: Board review, CFO / Financial modeling, Legal / contracts, Regulatory / antitrust, Key customer consents, Other
• How much run‑way do you need between LOI and close to be confident integration plans and retention incentives are in place? Options: < 30 days, 30–60 days, 60–90 days, > 90 days
• What external calendar constraints (earnings, tax year, regulatory filings) have forced you to slow or accelerate deals in the past? Options: Earnings / reporting periods, Tax-year deadlines, Regulatory filing windows, Major customer renewals, Other
• When timelines compress, which risks are you willing to accept and which are non-negotiable?

The Quiet Power Players

• Who outside the company — advisors, LPs, bankers, large customers — has de facto veto power even if not formally on the approval list? Options: LPs / Investment Committee, Lead bank / debt provider, Strategic customers, Industry regulator, Key suppliers, Other
• Which internal roles hold more influence than their titles suggest? Options: Head of Sales, Head of HR / Talent, Head of Product / Engineering, General Counsel, Head of Customer Success, Other
• How do you surface hidden objections early—direct interviews, anonymous feedback, reference checks, or other methods? Options: Direct stakeholder interviews, Anonymous surveys, Reference checks with ex-employees, Board pre-briefs, Third-party advisory review, Other
• Who do we need to persuade first to make decision-making smooth later in the process? Options: CEO, CFO, Board Chair, Key investor / LP, Major customer, Other
• What motivates these influencers most: risk reduction, personal reputation, financial upside, operational control, or something else? Options: Risk reduction / downside protection, Personal reputation / legacy, Financial upside / carry, Operational control / autonomy, Customer relationships, Other
• Give an example of a hidden influencer that ultimately shaped a deal outcome—how and why did that happen?

What Keeps Your CFO Up at Night?

• What's the worst financial surprise your CFO fears from an add-on, and how would that surprise show up in the P&L or cash flow?
• Which KPIs will finance watch most closely after close (select up to four)? Options: Cash flow / free cash flow, Gross margin, EBITDA, Customer churn / retention, Days Sales Outstanding (DSO), Working capital / inventory turns, Other
• What level of sensitivity and downside scenario testing do you require before you can sign off? Options: Basic sensitivity, Moderate scenario analysis, Thorough downside cases with stress tests, Full enterprise modelling including covenants
• How confident are you in the target's historic financials and internal controls? Options: Very confident, Somewhat confident, Doubtful, Unknown / needs review
• List the top three financial red flags that would stop this deal immediately.
• Would your CFO accept price mechanisms (escrows, earnouts) instead of full upfront payment if those red flags are present? Options: Yes — prefer earnout / escrow, Maybe — case-by-case, No — prefer clean economics

When Integration Goes Wrong — Tell Us a Story

• Think of an acquisition that failed to deliver — what was the single cause you wish you'd fixed earlier?
• Which integration failures do you see most often: people attrition, systems incompatibility, customer churn, cultural mismatch, or operational dissonance? Options: People / key talent loss, Systems / IT mismatch, Customer churn / revenue loss, Cultural mismatch, Operational process conflicts, Other
• How much integration capacity (team size or hours) can the platform company realistically commit in the first 100 days? Options: Minimal — < 1 FTE equivalent, Small — 1–3 FTEs, Moderate — 4–9 FTEs, Large — 10+ FTEs, Variable depending on deal
• Which integration responsibilities must the portfolio company own versus what can be run by the central M&A team? Options: Customer communications, People / retention incentives, Systems migration, Operational SOP alignment, Sales / go-to-market integration, Other
• How do you prefer to track early integration progress week-by-week (what dashboards or milestones)? Options: Retention rate / employee retention, Customer NPS / CSAT, Systems migration milestones, Revenue vs plan, Cost synergy capture, Other
• What escalation path should be used if customer retention or EBITDA lags materially in the first 90 days?

What Does 'Good' Look Like to Each Person?

• If we asked the CEO, CFO, board chair, and M&A lead separately, whose definition of 'success' would differ most and why?
• List the top three success metrics each stakeholder cares about — respond in the format Role: metric1, metric2, metric3 (CEO / CFO / Board / M&A).
• For customers and employees of the acquired company, what retention rates (year 1) would you need to consider the deal successful? Options: Employee retention > 90%, Employee retention 75–90%, Employee retention 50–75%, Customer retention > 95%, Customer retention 85–95%, Customer retention < 85%
• What change in customer NPS or CSAT over 12 months would you view as acceptable, neutral, or a failure? Options: Improve >5 points — excellent, Improve 1–5 points — acceptable, No change — neutral, Decline 1–5 points — concern, Decline >5 points — failure
• Which qualitative signs (leadership engagement, cultural alignment, customer sentiment) would make you comfortable even if early financials lag slightly?
• Who will own the final acceptance decision at the post-close validation gate (the person who flips the 'go/no-go' switch)? Options: CEO, CFO, Board, M&A Lead, Integration Lead, Joint committee

Making Decisions Together — Governance & Next Steps

• If we drafted a governance clause today, what single element would guarantee you feel comfortable signing it?
• Which governance model do you prefer during deal execution: tight central control, joint steering committee, or advisory oversight? Options: Central control by platform M&A team, Joint steering committee (platform + portfolio), Advisory oversight only, Hybrid — committee for big decisions
• How often should the steering committee meet and what standard materials should we provide each time (financial pack, integration milestones, risk register)? Options: Weekly — full pack, Bi-weekly — key dashboards, Monthly — summary, Ad-hoc for milestones / escalations
• Which formal approval gates should we lock in now (LOI, financing, board sign-off, post-close validation)? Options: LOI approval, Debt / financing approval, Board sign-off, Post-close validation (90 days), Regulatory approval, Other
• Who should be the single escalation contact for quick decisions during diligence (name or role)? Options: CEO, CFO, M&A Lead, Deal Partner (PE), Integration Lead, Other
• What communication cadence and deliverables do you expect from our M&A team over the next 30 / 60 / 90 days?

How Does Work Really Flow Here?

• Walk me through a typical week—what recurring meetings, reports, and decision points keep the company running?
• Which three leaders or teams own the day-to-day decisions that most affect revenue and customer experience?
• How often do you run formal performance reviews for commercial KPIs (revenue, retention, NPS)? Options: Weekly, Biweekly, Monthly, Quarterly, Ad-hoc
• When an urgent customer issue arises, what’s the escalation path and typical response time? Options: Same day, 24-48 hours, 3-7 days, Depends on priority
• Tell us about one recurring friction in your operating rhythm that silently steals time or focus—how long has it been tolerated?

If We Had to Close an Acquisition Tomorrow, What Would Break?

• How realistic is it that your current team could support an acquisition due diligence and integration while maintaining business-as-usual? Options: Fully realistic, Manageable with prioritization, High risk of disruption, Not realistic
• Which internal roles would need to be backfilled or deprioritized to take on M&A tasks—and how long would that take?
• What budget or external resource constraints do you anticipate for running concurrent diligence and integration activities? Options: Dedicated budget available, Limited budget—need approval, No budget yet, Unknown
• When integration work ramps up, which internal processes or teams have historically slowed the fastest (e.g., IT, HR, Sales Ops)? Options: IT/engineering, HR/payroll, Sales operations, Finance/reporting, Customer success, Other
• If you had to name the single biggest operational vulnerability during past change efforts, what is it and how long has it been an issue?

Where Your Customers Feel the Heat

• What customer segments show the greatest fragility when contracts, pricing, or service models change? Options: Enterprise, Mid-market, SMB, SMB - high churn, Other
• Which customer-facing processes create the most complaints or churn signals (onboarding, billing, support SLAs, product stability)? Options: Onboarding, Billing, Customer support, Product reliability, Account management, Other
• How have retention rates trended over the last 12–24 months for your top two segments, and what explanations do you have for those trends?
• Share a recent example where an operational change (internal or due to an acquisition) led to tangible customer dissatisfaction—what happened and who felt it most?
• Which customers would you consider mission-critical to preserve during an integration, and why?
• How confident are you in your ability to predict which customers will stay vs. leave after an acquisition? Options: Very confident, Somewhat confident, Not confident, No data

What Integration Success Has Actually Looked Like Here

• Think about the last acquisition or major partnership—what concrete signals told you it was stabilizing successfully?
• What integration milestones usually take the longest to reach, and why do they stall? Options: Systems migration, Customer transition, People alignment, Contract harmonization, Regulatory/compliance
• When integrations did not meet expectations, whose decisions or assumptions most contributed to that outcome? Options: Leadership prioritization, Under-resourced implementation, Poor target fit, Cultural mismatch, Other
• How do you measure integration ROI today—what metrics move the needle and over what timeframe?
• If you could repeat one integration practice that reliably delivered value, what would it be and how would you scale it?

Pipeline Reality Check—Is It Real?

• Your CRM lists X active targets—how many of those are genuinely strategic fits versus exploratory conversations? Options: Mostly strategic fits, About half fit, Mostly exploratory, Don't know / not tracked
• Which sourcing channels consistently yield the highest-quality targets (broker network, direct outreach, industry events, inbound referrals)? Options: Broker network, Direct outreach, Industry events, Inbound referrals, Proprietary lists, Other
• When you look at current pipeline stages, what percentage are actionable within 90 days, and what blocks the rest? Options: >50%, 25–50%, <25%, Unknown
• Describe one near-term target in your pipeline that feels like the best fit—what makes it attractive and what risks are obvious?
• How are target fit and valuation tolerance currently scored or ranked, and who approves moving a target to diligence?

Data and Systems: The Invisible Risk

• If we attempted to consolidate CRM, billing, and support platforms with a new acquisition, how many different systems would we be aligning? Options: 1–2, 3–4, 5–7, 8+
• How accessible and clean is the data we’d need for diligence (customer lists, churn history, contracts, revenue by cohort)? Options: Immediately accessible and clean, Mostly accessible but needs cleanup, Fragmented and hard to extract, Not available
• Which system migrations have caused the most customer-impacting errors in the past, and what did that look like operationally?
• Who holds administrative access and ownership of each critical system today, and how quickly can they grant external diligence access?
• What reporting or dashboards do you rely on to monitor post-close health, and what gaps would hamper early detection of integration issues?

What’s the One Thing We Can’t Compromise On?

• When push comes to shove in an integration, what outcome would you refuse to trade off (e.g., customer satisfaction, EBITDA margin, cultural fit, retention of founders)? Options: Customer satisfaction, EBITDA margin, Cultural fit, Retention of key staff, Regulatory/compliance
• Why is this non-negotiable—what would happen if it slipped even slightly?
• Who on the leadership team is most protective of this priority and who will sign off that it’s preserved post-close?
• If preserving this priority requires additional investment or slower timelines, how willing are you to accept that tradeoff? Options: Very willing, Somewhat willing, Reluctant, Not willing

Sequencing & Quick Wins—Where Do We Start?

• What integration tasks would deliver visible value within the first 30–90 days and who should own each?
• Which decisions must be made before close versus what can be safely deferred until after day one? Options: All critical before close, Some key before close, rest after, Mostly after close, Undecided
• If we had a single cross-functional integration lead, which person would you trust most to carry that role and why?
• What escalation paths do you want in place for the first 100 days—who gets alerted for revenue risk, for employee retention, and for system outages?
• Realistically, when could your team begin executing an integration plan if a deal were signed next month? Options: Immediately, In 2–4 weeks, In 1–3 months, Longer than 3 months

Getting Our Bearings — a quick readiness check

• Who from your leadership and operations team should be the primary contacts for pre-close readiness? Options: CEO, CFO, COO/Head of Ops, Head of M&A/Corporate Dev, Head of HR/People, Head of IT, Legal Counsel, Other (please name)
• What is the single best day/time window to schedule recurring readiness calls to ensure momentum? Options: Mon morning, Mon afternoon, Tue/Wed mid-day, Thu morning, Fri morning, Ad hoc by availability
• Tell us briefly about your most recent acquisition experience — what worked, and what surprised you the most?
• How would you describe your current organizational bandwidth for diligence and early integration activities? Options: We can commit dedicated time (protected), We can reprioritize tasks as needed, We have very limited capacity, Unsure — need to evaluate
• Are there any calendar or governance constraints we must respect before close (e.g., board blackout, fiscal year-end, employee leave windows)?

If Data Disappeared Tomorrow, What Would Break First?

• If we could only secure three datasets from the target before close, which three would you put at the top of the list and why? Options: Customer contracts & T&Cs, AR aging/receivables, Revenue by customer / MRR, Customer contact list & engagement history, Product/service delivery logs, Employee records/key hire list, Other (please specify)
• Which systems currently hold the target’s critical customer and revenue data? Options: CRM (Salesforce/HubSpot/Other), Billing/CPQ system, ERP/Accounting, Custom databases, Spreadsheets/Shared Drives, Other
• How would you rate the cleanliness and completeness of those datasets today? Options: High quality — few gaps, Moderate — some cleanup required, Poor — significant gaps or inconsistencies, Unknown
• What previous data handoffs have caused delays or rework in your deals, and how long did those blockers typically take to resolve?
• Who on your team is best placed to validate dataset completeness and sign off on data readiness? Options: Head of IT, Head of Finance, Head of Sales/Customer Success, External advisor, Other (name/role)

Who's Actually Owning Diligence — and Are They Ready to Deliver?

• Who will be accountable day-to-day on your side for driving diligence deliverables to completion? Options: Dedicated M&A lead (internal), CFO or Finance lead, VP/Head of Ops, Third‑party advisor, Split across functions (specify)
• How clear are those owners on timelines, expectations, and the specific deliverables they must produce? Options: Crystal clear, Mostly clear, Some ambiguity, Not defined
• Do the assigned diligence owners have protected time or delegated authority to prioritize this work over business-as-usual tasks? Options: Yes — protected time and authority, Yes — some time but limited authority, No — juggling BAU heavily, Unsure
• What external advisors (legal, tax, IT, HR) are already engaged and what scope will they cover pre-close? Options: Legal, Tax, IT/Infrastructure, HR/Compensation, Valuation/Accounting, No advisors engaged yet, Other (specify)
• If a key owner becomes unavailable, what is the escalation path and who is the backup?

The People-Risk Conversation No One Likes — but We Need to Have It

• How confident are you that critical target employees will remain through the first 100 days post-close? Options: Very confident, Somewhat confident, Concerned, Very concerned
• Which specific roles or individuals would cause disproportionate operational risk if they left immediately after close?
• Have you identified retention incentive structures and approvals needed pre-close to secure those employees? Options: Yes — approved and budgeted, Planned — pending approvals, No plan yet, Need help designing incentives
• From past integrations, what levers have you found most effective to preserve seller talent (e.g., equity, cash bonuses, title/role clarity)?
• What cultural differences do you anticipate between teams that could materially affect retention or productivity? Options: Leadership style, Compensation philosophy, Customer service approach, Pace of decision-making, Tech stack/practices, Other

Controls That Actually Prevent Chaos — change gates and approvals

• What formal change-control gates do you enforce today that would apply to an acquired business (e.g., code releases, pricing changes, org changes)?
• Who must sign off on changes affecting customers, billing, or critical systems? Options: CEO, CFO, Head of Product/Engineering, Head of Sales/CS, Legal, Other (specify)
• How long do typical approval cycles take for emergency vs. planned changes? Options: Same-day, 1–3 days, 4–10 days, More than 10 days, Varies widely
• Do you have predefined rollback procedures and a person authorized to trigger them? Options: Yes — documented and tested, Yes — documented but untested, No — ad hoc, Unsure
• Describe the most common source of integration governance friction you've experienced and how it was resolved.

Money on the Table: Funding, Approvals, and Timing

• If a retention or remediation need drives an unexpected one-time cost of ~30% above estimates, do we have pre-approved contingency funding? Options: Yes — contingency budget exists, Partial — some funds available, No — would require approval, Unsure
• What funding sources are available for immediate post-close needs (e.g., platform reserves, escrow, portfolio company Opex, external financing)? Options: Platform reserves, Escrow/holdback, Portfolio company cashflow, Bridge financing/credit, Vendor financing, Other
• Who has final sign-off authority for draws against contingency or post-close integration spend? Options: Platform CFO, Portfolio company CFO, Investment Committee, CEO, Other (specify)
• What are typical approval lead times for funding above $25k / $100k / $500k in your organization? Options: Same-day, 1–3 days, 4–10 days, More than 10 days
• Are any financial covenants or lender constraints likely to limit post-close integration spend? Options: Yes — specific constraints, Possibly — need to review, No constraints, Unsure

Customer Signals & Experience — protecting revenue and trust

• Which customer metric — if it slipped materially — would make you stop the integration to reassess? (Pick the strongest single trigger.) Options: NPS/CSAT drop, Churn increase, Major SLA breach, Loss of top 3 customers, Material billing errors, Other (specify)
• How will we measure customer experience impact in the first 100 days (tools, frequency, owners)?
• Which customers or segments do you consider high churn-risk during a transition, and why?
• Do you have pre-approved customer communication templates and a single owner for external messaging during transition? Options: Yes — templates and owner identified, Templates exist but no owner assigned, No templates — need to create, Unsure
• How quickly can support routing, SLAs, or account ownership be changed if we see customer issues post-close? Options: Immediately (same-day), 1–3 days, One week, Longer — requires approvals

Systems Migration & Access — the technical gates that delay cutover

• What single systems access gap historically causes the longest cutover delays (e.g., lack of DB exports, missing API keys, SSO restrictions)?
• Please list required access types and current status for each (CRM, billing, payroll, source control, production DB, SSO).
• Which credentials or data transfers require legal or vendor approvals that could extend timelines? Options: Vendor contracts/consent, Data transfer agreements, Customer consent, Licensing restrictions, None
• How frequently can the target provide production-level exports or snapshots for testing (daily, weekly, one-time)? Options: Daily, Several times a week, Weekly, One-time/once off, Cannot provide
• Are there third‑party integrations (payment processors, analytics, partners) that would need separate coordination or approvals?

Commitments, Timelines & What We Need from You Right Now

• What commitment can you make today to guarantee readiness on Day 0 (e.g., dedicated person, data exports delivered, signed retention plan)?
• Provide a realistic target close date and any immovable milestones that govern that timing.
• Who will attend the pre-deployment readiness gate review and who has final go/no-go authority? Options: CEO, CFO, Head of Ops/Delivery, Platform M&A lead, Investment Committee rep, Other
• What deliverables can your team provide within the next 7 days to materially de-risk the close (e.g., access credentials, org chart, top customer list)? Options: Access credentials, Org chart & key contacts, Customer contract list, AR aging & revenue detail, Retention plan approvals, Other (specify)
• What would make you hesitate to commit to these timelines or deliverables right now?

Opening: Who's Speaking for Success?

• Who will be our primary point of contact for validation and sign-off after close? Options: CEO, CFO, Head of Operations, Head of Integration/PMO, Head of Sales/Commercial, Other
• Does that person have final authority to approve go/no-go decisions for validation gates, or do they route to a committee? Options: Has final authority, Routes to CEO/CFO, Routes to board/investor committee, Shared authority (multiple sign-offs), Not yet defined
• How many hours per week can your validation lead realistically dedicate to post-close validation activities in the first 90 days? Options: 40+ hours, 20–40 hours, 10–20 hours, Less than 10 hours, TBD
• Tell us about one prior integration you led or observed—what validated success most clearly in the early months?
• What reporting cadence do you prefer for validation checkpoints (e.g., weekly scorecard, biweekly review, monthly board update)? Options: Weekly, Biweekly, Monthly, Ad hoc as issues arise, Other

Before We Call It a Win — What's Truly Non‑Negotiable?

• If this deal misses one promise in the first 100 days, which single failure would make you say it wasn't worth doing? Options: Loss of a top customer or cohort, Material revenue miss vs plan, Failure to migrate critical system, Loss of key leadership, Major NPS decline, Other
• Across retention, NPS, systems migration, and financials, please rank which area would be the most damaging if it underperforms (1 = most damaging). Options: Customer retention, Employee/leadership retention, Systems/data migration, Revenue/EBITDA targets, Regulatory/compliance issues, Brand/reputation
• What tolerance do you have for misses against acceptance criteria in month 1, month 2, and month 3 (express as +/− % or absolute thresholds)?
• Give one concrete example of an integration outcome you consider unacceptable—and why it would be a blocker for future add-ons.
• Who on the investor/team side would escalate if the non-negotiable item above begins to trend poorly? Options: Deal lead (PE M&A team), Operating partner, Board representative, Portfolio company CEO/CFO, Other

Where the Rubber Meets the Road: Customers, Retention & NPS

• Why do you believe customers might leave during or after integration—what are the root causes you've seen?
• What is the current baseline churn (monthly or annual) for the target’s customers, and what target retention rate must we achieve post-close? Options: Provide numeric baseline and target (%)
• What is the current NPS (or equivalent customer satisfaction score) for the target and for the platform, and what delta would signal success?
• Which customer segments or top-accounts are most at risk during transition—please list by revenue concentration or strategic importance.
• What customer communication cadence and owner will be in place during the first 90 days to preserve trust? Options: Daily outreach from account teams, Weekly customer newsletters, Assigned executive sponsor per key account, Customer success-led onboarding, Other
• How will we measure customer retention and satisfaction in real time—what systems or dashboards can we access? Options: CRM subscription dashboards, Customer success platform (e.g., Gainsight), Custom BI reports, Manual tracking spreadsheets, Not yet available

People Pivots: Who Must Stay and Why

• If three people on day one handed in notices, which three roles would cause the most strategic damage?
• List the names/titles of critical employees we must retain and the expected timeline for their integration into platform processes.
• Do you have retention incentives planned (cash, equity, bonus) and what is the expected duration and payout trigger? Options: Yes—cash-based, Yes—equity-based, Yes—bonus tied to targets, No formal plan yet, Other
• Historically, how long after an add-on close have critical roles tended to churn here, and what patterns should we watch for?
• Who owns people retention day-to-day, and who will approve emergency retention funds if needed? Options: Platform CEO, Portfolio CFO, Head of HR/People, Operating Partner (PE), Board/investor

Systems, Data, and the Migration Cliff

• Which single system migration failure would immediately cause customer disruption or financial misstatement? Options: Billing/Revenue system, CRM/customer data, Order management/fulfillment, Financial close/ERP, Support/ticketing system, Other
• Please inventory the critical systems involved, identify the source-of-truth for customer data, and note who has admin access today.
• Which migration approach do you prefer and why—big bang, phased coexistence, or parallel with reconciliation? Options: Big bang, Phased coexistence, Parallel + reconciliation, Keep systems separate (no migration), Undecided
• What test, cutover, and rollback plans exist? Describe one scenario where rollback would be executed and who signs the decision.
• How complete is data mapping and extraction from the target today (e.g., percent of records validated and ready)? Options: >90% validated, 70–90% validated, 40–70% validated, <40% validated, Unknown
• Who will provide access to system logs, test environments, and sample datasets for the validation team? Options: Platform IT/CTO, Target IT lead, Third-party integrator, PE operations team, Not defined

Money Matters: Targets, Timing, and Accountability

• What are the explicit financial acceptance criteria for this transaction at day 30, day 60, and day 100 (revenue, EBITDA, cost synergies, cash conversion)?
• Who will own the monthly reconciliation between deal model commitments and actuals, and who is the escalation contact for discrepancies? Options: Platform CFO, Portfolio company finance lead, PE FP&A team, External accountant, Other
• Are there earnouts or contingent payments tied to early performance? If so, describe the triggers and measurement owner. Options: Yes—earnout tied to revenue, Yes—earnout tied to EBITDA, No earnouts, Other/complex structure
• What accounting or one-time integration costs do you expect to hit the P&L in the first 100 days, and who will approve them?
• If the financials miss targets by a material amount, what remedies are acceptable (e.g., holdbacks, remediation plan, earnout adjustment)? Options: Draw on contingency funds, Performance remediation plan, Negotiated holdback, Renegotiate earnout, Other

Signals We Can Trust: Evidence, Timing, and Reporting

• What single metric reported at day 30 would most convince you the integration is on track? Options: Net retention %, NPS change, Billing/collections status, System uptime & data integrity, Employee retention of critical roles
• Which dashboards or reports can we expect to see during validation, and are they automated or manually compiled? Options: Automated BI dashboards, CRM-built reports, Manual spreadsheets, Third-party monitoring tools, Not available yet
• Who are the named KPI owners for customer retention, NPS, systems migration, and finance, and how should we contact them for rapid clarification?
• What thresholds should trigger an immediate escalation (e.g., >x% churn in a cohort, revenue shortfall > $Y, critical system outage > Z hours)?
• How will we document and share validation evidence with the board/investors—one-line summary, package of artifacts, or live demo? Options: One-line summary + dashboard, Full evidence package (data + logs), Live demo of systems, Ad hoc memo as needed, Other

Agreeing the Acceptance Checklist and Next Gates

• If we had to define a single pass/fail gate at day 60, what would it be and why?
• Please list the specific acceptance criteria (short, measurable statements) we should include for: customer retention, NPS, systems migration, and financials.
• Who must sign off on each acceptance criterion (name/title), and who has veto rights for the overall gate?
• If a gate is failed, what immediate remediation steps would you accept (e.g., 30‑day remediation plan, limited holdback release, contingency funding)? Options: 30‑day remediation plan, Contingency funding release, Partial holdback, Renegotiation with seller, Immediate pause to integration activities
• Are there any legal, compliance, or customer contract clauses that must be validated before we can sign off on acceptance criteria? Options: Yes—customer contract approvals, Yes—regulatory/compliance checks, No critical clauses, Not sure
• Can you commit to providing the required evidence (dashboards, data extracts, customer call logs) by the agreed reporting dates? If not, what constraints exist? Options: Yes—fully committed, Partially (some data available), No—significant constraints, Need help to enable