Start with the Moment That Matters

• Where are you today in the transaction timeline? Options: Already closed (Day One passed), Signed but not closed (pre-close), Near close (within 30 days), Early diligence / >30 days from close, Uncertain
• Who will be responsible for reporting progress against the deal model to investors or the board? Options: PE operating partner, Corporate COO, CFO, Chief Integration Officer, Deal sponsor (CEO), Integration Manager / IMO lead, Other
• Which two synergy line items from the deal model are top of mind right now? Options: Cost of goods / sourcing, SG&A consolidation, Sales cross-sell revenue, IT consolidation savings, Headcount / org redesign, Commercial pricing, Other
• How would you describe the current level of confidence in the assumptions behind those synergies? Options: Very confident, Somewhat confident, Doubtful, Unsure / need validation
• Tell us briefly: what keeps you up at night about this integration (one or two sentences)?

Where the Deal Could Start Losing Value

• If you could pick one immediate failure that would erode the deal value fastest, what would it be? Options: Loss of key sellers, IT or financial reporting delay, Customer churn from account reassignments, Executive attention drift, Regulatory / compliance surprise, Other
• How many weeks of integration delay would you estimate starts to materially cut into projected investor returns? Options: <4 weeks, 4–8 weeks, 9–16 weeks, >16 weeks, Not sure
• Which parts of the business carry the largest single-point-of-failure risk for the deal model (pick up to three)? Options: Top-sales accounts / GTM, Finance & consolidation, IT / ERP / CRM, Key manufacturing lines, Critical suppliers, Regulated operations, Other
• Can you quantify (or estimate) the dollar or percentage impact if that failure occurs in the first 90 days? Options: % of annual revenue, % of projected synergies, Estimated $ impact, Prefer not to quantify here
• Describe an integration (in this company or another) where a similar risk actually materialized—what happened and how was it handled?

Who Really Decides (and Who Gets Left Out)

• If the integration becomes politically contested, whose misalignment would most likely sink decisions? Options: PE operating partner / investment committee, Acquirer CEO / board, Target CEO / leadership, CFO, CHRO/People leader, Integration lead / IMO, Other
• List the core sponsor, executive approvers, and day-to-day owners you expect to involve in integration governance (names or roles).
• How often does the investment committee or board expect a formal update during the first 100 days? Options: Weekly, Bi-weekly, Monthly, Only at milestones, Not specified
• Which stakeholders have veto rights or final sign-off on compensation / retention decisions? Options: Investment committee, Acquirer HR / CHRO, Target leadership, CFO / finance, CEO, Other
• Have you previously set up an Integration Management Office (IMO) in-house? If yes, what worked and what didn't? Options: Yes — worked well, Yes — had issues, No — we relied on existing teams, No — first time

Why People Quit in the First 90 Days

• What's the single most convincing reason a top-performer would walk in month one after close? Options: Compensation misalignment, Role uncertainty / reporting changes, Loss of autonomy / culture clash, Customer account disruption, Unclear career path, Other
• Which employee groups are highest retention priorities (pick all that apply)? Options: Top sales performers, Product / engineering, Customer success / account managers, Critical ops / manufacturing staff, Finance leaders, Other
• Do you have existing retention levers (bonuses, offers, retention agreements) allocated for Day One? If so, what is the typical time horizon for those levers? Options: Yes — 3 months, Yes — 6 months, Yes — 12 months, No formal levers yet, Unsure
• How would losing 1–3 top sellers affect revenue over the next 6 months—give an example or estimate?
• What conversations have you had with target leaders about retention and role clarity so far, and how did they respond?

When Systems Go Silent

• Which single data gap would create the most dangerous blind spot for governance after close? Options: Consolidated financials, Sales pipeline visibility, Customer contract terms, HR/compensation data, Supplier commitments, IT access / security logs, Other
• What is your current plan (and timeline) for financial and operational cutover (ERP/GL, payroll, reporting)? Options: Cutover Day One, Phased over 30 days, Phased over 60–100 days, No firm plan yet, Other
• Which systems must remain live and synchronized across both organizations for the first 30 days? Options: ERP/Finance, CRM/Sales, Payroll/HRIS, SCM / MRP, Support / Ticketing, Other
• Who owns contingency decisions if an IT cutover misses its window (roles and escalation path)?
• Tell us about a past cutover that stumbled—what early warning signs would you want us to watch for here?

If Day One Went Perfectly

• Imagine Day One exceeded expectations—what single outcome would make you call it a success? Options: All retained top talent, Clean financial close & reporting, No customer churn, IT and payroll functioning, Immediate governance cadence in place, Other
• What are the three measurable signals that would prove Day One was successful (specific metrics or milestones)?
• Who must be visibly engaged on Day One to convey unity and prevent defections? Options: Acquirer CEO, Target CEO, PE operating partner, Integration lead, Functional heads (Sales/HR/IT/Finance), Other
• If we could guarantee one operational fix by Day One, which would you choose and why? Options: Compensation harmonization, Customer account owner continuity, Financial consolidation/reporting, IT single-sign-on / access, Retention payouts, Other
• How would achieving that Day One fix change your conversations with investors in week two?

Mapping the 100‑Day Win

• Which 100-day milestone do most teams promise and fail to deliver on in your experience? Options: Full cost synergies realized, Customer retention targets, IT consolidation, Org redesign complete, Supplier savings captured, Other
• What weekly evidence would convince you that the 100-day plan is on track (pick up to three)? Options: Actual $ synergy tracking, Completed deliverables vs. plan, Retention status of key people, Customer churn rates, IT cutover milestones, Risk register updates
• Who should chair the weekly synergy review—role, not name—and what escalation authority should they have? Options: PE operating partner, CFO, Integration lead / IMO, CEO, Steering committee member
• What dependencies (vendors, approvals, data) are currently most likely to derail a 100-day commitment?
• How would you like synergy delivery to be reported to the board—format and cadence (e.g., weekly dashboard + monthly deep dive)? Options: Weekly dashboard + monthly deep dive, Bi-weekly executive summary, Monthly only, Ad-hoc for issues

What Would Convince the Investment Committee

• What single piece of evidence would move your investment committee from skeptical to supportive? Options: Comparable deal case study, Pilot diagnostic showing risk reduction, Clear IMO & owner list, Committed retention funding, Initial week-one results
• Have you seen comparable deal outcomes from advisors you liked? What specifically proved persuasive? Options: Yes — methodology, Yes — outcomes / metrics, Yes — executive engagement, No comparable examples seen, Not sure
• Would your committee require a short pre-close diagnostic or pilot before approving an integration plan? If yes, how long is acceptable? Options: Yes — 2 weeks, Yes — 4 weeks, Yes — 6–8 weeks, No, not required, Unsure
• What format of evidence (quantitative model, client references, case videos, detailed plan) carries the most weight for your committee? Options: Quantitative model, Client references, Detailed project plan, Pilot outcomes, Other
• What previous advisory engagement caused the committee to push back—what were their specific objections?

Commitments and Next Steps — Where We Start Together

• If we agreed to partner, what early commitment would be non‑negotiable from your side? Options: Dedicated IMO seat / full-time integration lead, Budget for retention & pilots, Access to financial and HR systems, Executive sponsor time/week, Authority to bind certain decisions, Other
• What constraints (budget, people, legal, regulatory) should we be aware of before proposing a Day One plan?
• Which of the following immediate deliverables would you prioritize for a 4–6 week engagement ahead of close? Options: Risk heat map & mitigation plan, Retention & comp harmonization blueprint, Day One runbook & checklist, IT cutover schedule, IMO charter and RACI
• How soon could your team commit to a kick-off workshop if we proposed a pre-close diagnostic? Options: Immediately, Within 1–2 weeks, Within 3–4 weeks, Longer / need to discuss
• What would success look like for you at the end of a short pilot (2–6 weeks)? Please name 2–3 specific, measurable outcomes.

Quick orientation — where are we starting?

• Which best describes your role in this integration? Options: PE operating partner / fund representative, Chief Integration Officer, Corporate COO, Divisional President / business leader, Head of M&A, Other
• What is the transaction status today? Options: Closed, Imminent (within 30 days), Pre-sign / due diligence stage
• Which pressures are keeping you busiest this week? (pick all that apply) Options: Protecting top revenue producers, IT cutover and reporting deadlines, Retention and compensation harmonization, Customer account continuity, Regulatory or compliance timing, Board/investor reporting cadence, Other
• How were the deal synergies characterized in the model (brief summary of types and timing)?
• Who will be our primary counterpart for day-to-day work (name(s) and title preferred)?

If we don’t move fast, what dies first?

• Walk me through the worst-case Week 6 scenario—whose loss or which gap would make the deal story unravel?
• Which of these outcomes do you currently rank as highest risk (select up to three)? Options: Loss of top sellers / revenue producers, Quarter(s) of missing consolidated financials, Major customer churn due to account changes, Failure to deliver promised cost savings, Key systems migration failure, Regulatory or contract breaches
• How long has this primary risk been visible to leadership? Options: Less than 30 days, 1–3 months, 3–6 months, More than 6 months
• Have you already observed early warning signs (e.g., voluntary exits, customer complaints, failed tests)? Tell me what happened and when.
• How confident are you that existing internal teams can accelerate timelines without outside support? Options: Very confident, Somewhat confident, Doubtful, Not at all confident

Who decides what counts as success?

• When the board asks 'Did this acquisition deliver?', who has the final sign-off and what proof will satisfy them?
• Which stakeholders must be consulted before we change scope, timelines, or targets? Options: Investment committee / limited partners, CEO / executive sponsor, CFO / finance leadership, Business unit heads, Legal / compliance, HR / talent leadership, IT leadership, Other
• What are the non-negotiable KPIs or financial milestones tied to the investment committee's approval?
• How often does leadership expect formal progress updates during the first 100 days? Options: Weekly, Biweekly, Monthly, Ad hoc / as needed
• If a KPI misses target by 10–20%, what is the likely governance response? Options: Reforecast and continue, Renegotiate terms with investor, Pause or re-prioritize initiatives, Escalate to investment committee for remediation, Other

What’s living in the gray zone right now?

• Which roles, teams, or customer segments are currently stuck between the two organizations with no clear owner?
• Which functional overlaps worry you most today (pick all that apply)? Options: Sales / account coverage, Finance / close & reporting, IT infrastructure & apps, HR / compensation & benefits, Operations / supply chain, Customer service & retention
• Do you have up-to-date org charts and RACI (who-owns-what) for the combined entity today? Options: Complete and current, Partial — some functions only, Minimal — high level only, None available
• How are top-seller compensation and retention currently being addressed between the two companies?
• Which named customers would you consider concentration or reputation risk if account ownership changes? (list top 3–5)

I’m going to assume your synergy targets won’t wait — are they real?

• Roughly what portion of the modeled synergies depends on customer retention and revenue stability versus cost and back-office consolidation? Options: Mostly revenue / retention, Mostly cost and back-office, Roughly even split, Unclear / mixed
• Which initiatives in the model are labeled as 'Day One to 100 days' contributors versus 'long-tail' contributors?
• Do you have comparable integrations (vertical and deal size) we can benchmark against? If yes, which ones? Options: Multiple comparable deals, One comparable deal, No comparable deals, Unsure
• From past integrations, what was the single biggest initiative that failed to deliver and why?
• How confident are you in the timing dependencies (IT windows, regulatory approvals, contract novations) that the model assumes? Options: Very confident, Somewhat confident, Uncertain, Not confident at all

What would Day One look like if nothing broke?

• If Day One goes perfectly, who is still employed, where are revenues recorded, and which consolidated reports are available that week?
• Which Day One actions do you consider non-negotiable to protect deal value? (select all that apply) Options: Retention offers to named employees, Compensation harmonization for sales, IT cutover for financial consolidation, Customer account continuity plan, Immediate governance & decision forum, Other
• What is the earliest acceptable IT cutover window to avoid a reporting gap? Options: Within 7 days, 2–4 weeks, 1–3 months, Longer than 3 months
• How do you plan to communicate Day One changes to customers and key employees? Options: Executive-led joint comms, Account-level outreach by managers, Automated CRM communications, No defined plan yet, Other
• Who do you expect to lead Day One command — your IMO, an internal team, or a joint model? Options: External IMO / consultancy, Internal acquirer team, Joint IMO (shared), Undecided / other

Where could a small pilot prove the point?

• If we ran a 4–6 week diagnostic pilot now, which area would give the fastest and most reliable signal that the model holds? Options: Sales retention and account continuity, Finance close & reporting, IT migration feasibility, HR / compensation alignment, Supply chain / operations continuity
• What specific measurable outcome from that pilot would convince investors to stay the course? Options: Confirmed revenue run-rate, Closed financial reporting gap, Retention of named sellers, Validated cost savings estimate, Other
• Who on your side must be involved for a pilot to produce credible results (roles/names and time availability)?
• Which internal data sources or previous deal artifacts can we access quickly for benchmarking the pilot? Options: ERP / GL data, CRM opportunity & pipeline, HRIS / comp plans, Previous integration playbooks, None readily available, Other
• What would be a deal-breaker finding in a pilot that would force you to pause or renegotiate the transaction assumptions?

How do you want this to feel six months from now?

• If the board asks for evidence in six months, what tangible outcomes would make you feel proud — and what outcome would keep you up at night?
• Which governance cadence would keep you comfortable during the first 100 days? Options: Weekly executive reviews, Biweekly leadership syncs, Monthly board updates, Ad hoc dashboards only
• What level of handoff to BAU do you expect after 100 days? Options: Full handoff to BAU, Shared ownership with IMO for transition, External support continues 6–12 months, Undecided
• How would you prefer synergy tracking to be presented to the board? Options: Realized dollar impact, Run-rate impact, Both realized and run-rate, Narrative with milestone evidence
• What would make you decide to extend external support beyond 100 days (select all that apply)? Options: Missed KPIs / slow recovery, Leadership bandwidth constraints, Further acquisitions / roll-up activity, Unexpected regulatory or contract issues, Other
• Are you willing to commit named stakeholders to participate in a diagnostic pilot and Day One activities? If yes, list names/titles and expected weekly time commitment.

Before the Clock Starts: What You Already Know

• Where are you in the acquisition timeline and which immediate deadline feels most pressing? Options: Pre-close (<30 days), Close imminent (0–7 days), Closed within 30 days, Closed 1–3 months ago, Other
• Who will be the primary decision owner for integration outcomes and what level of authority do they hold?
• Which investor success metrics are non-negotiable for the fund or board? Options: EBITDA uplift, Cost synergies realized, Revenue acceleration/cross-sell, Cash conversion/working capital, Other
• What is the single-number deal model target (annual $ or % improvement) you are expected to hit, and how confident are you in that estimate? Options: Confident (>85%), Reasonably confident (60–85%), Some uncertainty (35–60%), Low confidence (<35%), We don't have a clear number
• If you already ran any pre-close diagnostic or pilot activity, what were the top three highest-risk findings?

Why Day One Will Make or Break the Deal

• What would it cost the deal if Day One didn’t stabilize within the first week? Options: Minimal (<1% of deal value), Small (1–5%), Moderate (5–10%), Severe (10%+), Can't estimate
• Which of the following risks do you believe are most likely to materialize in the first 90 days? Options: Key talent loss, IT downtime/data loss, Customer churn from account changes, Regulatory or compliance delays, Contractual liabilities, Supply chain disruptions, Other
• How frequently do you expect to require an executive-level escalation for integration decisions during the first 30 days? Options: Daily, Several times a week, Weekly, As needed, Never
• Which stakeholders on either side have veto or slow-path authority that could bottleneck Day One decisions, and how quickly do they typically respond?
• Thinking back to a recent acquisition you managed or observed that struggled at Day One—what went wrong and what would you change now?

Who Are We Losing If Plans Slip?

• Name the three roles or teams which, if they left on Day One, would most undercut revenue or operational continuity.
• Which customer segments or top accounts are most vulnerable to account team reassignment, and why? Options: Top 10 customers, Top 50 customers, Mid-market accounts, SMB/Long-tail, All segments equally at risk
• Which retention levers have been approved or are being considered (stay bonuses, retention agreements, equity, earnouts, etc.) and who signs them? Options: Stay bonuses, Formal retention agreements, Equity/earnouts, No retention plan yet, Other
• How confident are you that compensation harmonization will not trigger unintended departures? Options: Very confident, Somewhat confident, Neutral, Somewhat unconfident, Not confident at all
• How long have concerns about talent retention been on the radar for this deal? Options: Since deal origination, During due diligence, Only after LOI/definitive docs, Not considered until now

What Systems Could Trip You Up

• Which single IT dependency could prevent you from consolidating financials or reporting accurately next quarter? Options: ERP migration/consolidation, Payroll/HRIS cutover, CRM/billing continuity, Inter-company accounting interfaces, Data warehouse/reporting integration, Other
• What cutover windows, month-end or quarter-end blackout periods, or external deadlines constrain migration timing? Options: Specific month-end windows, Quarter-end only, No planned blackout, Multiple constrained windows, Other
• Which runbooks, test plans, or data-mapping artifacts exist today and which critical ones are missing?
• Who will sign off on data integrity and consolidated reporting after cutover, and do they have authority to pause rollouts?
• If a migration produces material reporting discrepancies, what fallback or rollback option do you have available? Options: Full rollback plan, Partial rollback, Manual reconciliation plan, No clear plan, Other
• How will IT dependencies affect customer-facing systems (CRM, billing, order management) in the first 30 days? Options: Major impact expected, Some impact, Minimal impact, No impact anticipated, Unsure

Hidden Costs: What’s Not in the Deal Model

• What recurring or dual-running cost has surprised your team in past integrations and could erode projected synergies here?
• Which of these hidden cost categories do you anticipate in this integration? Options: Dual payroll/operational costs, Parallel IT licenses and hosting, Contract termination or break fees, Temporary consulting/contractor costs, Regulatory/compliance remediation, Real estate/office consolidation, Other
• Which synergy lines in your deal model feel most optimistic versus well-evidenced? Options: Cost of goods sold (COGS) savings, SG&A rationalization, Sales cross-sell revenue, Procurement/vendor rationalization, Other
• How will you measure and attribute savings back to specific deal-model line items, and who must approve that evidence?
• What governance cadence and forum will you use to review synergy realization and cost run-rate in the first 100 days? Options: Daily standup/operational, Weekly executive steering, Bi-weekly review, Monthly board updates, No cadence established

If You Had a Crystal Ball: What Investors Will Want to See

• If investors asked for proof on Day 101, what single data point would make them stop questioning the deal?
• Which leading indicators will you track weekly to demonstrate progress against the model? Options: Retention rate of critical staff, Weekly revenue for key accounts, Cost run-rate vs baseline, IT system availability/Uptime, Customer churn rate, Order fulfilment or backlog, Other
• What acceptance criteria will you use to declare an initiative delivered and attributable to the deal model?
• Who will own the weekly synergy tracker, and how do you plan to transition ownership to BAU? Options: Integration team (IMT), Functional lead (Finance/Commercial), Corporate finance/controller, Hybrid shared ownership, Other
• How often do you want consolidated reporting to investors/board during the first 100 days? Options: Weekly, Bi-weekly, Monthly, Quarterly, Ad hoc

What Would Good Change Feel Like? Practical Next Moves

• What single small change we could make in the next 7 days would most increase your confidence in Day One readiness?
• Which quick wins could we pilot in a 2–4 week diagnostic to materially reduce immediate Day One risk? Options: Execute retention agreements for top talent, Run critical systems smoke tests, Freeze account ownership changes for top accounts, Establish temporary rapid-decision governance, Review/secure critical vendor contracts, Other
• How open are you to an external pre-close diagnostic or pilot specifically focused on Day One readiness? Options: Very open, Somewhat open, Unsure, Not open
• What resources (time, people, budget) can you commit in the next 30 days to shore up Day One readiness? Options: Dedicated full-time integration lead, Part-time functional SMEs, Budget for external consultants, No additional resources available, Other
• Who should sit on a short 'Day One' decision roster (names/roles) and what is their typical availability window?
• If we ran a short diagnostic and delivered one concrete outcome, which result would make you say 'yes, do it'? Options: Prioritized, evidence-backed risk list with owners, Signed Day One plan with owners and timelines, Costed retention package for critical staff, Sample weekly governance and reporting cadence, Other

Where Are We Starting From — a quick snapshot

• Briefly, what phase is your transaction currently in? Options: Pre-close (due diligence), Signed but not closed, Closed within last 30 days, Closed 1–3 months ago, Closed >3 months ago
• What is the headline deal model (total targeted synergies and the timeline you shared with investors)?
• Who will act as the primary internal sponsor for integration and who reports to them?
• Which functional areas carry the largest proportion of the synergy target? Options: Finance & Reporting, IT / Systems, Commercial / Sales, HR / Compensation, Operations / Supply Chain, R&D / Product, Other
• How confident are you today that your internal team can hit the model without external support? Options: Very confident, Somewhat confident, Unsure / mixed, Not confident
• How many weeks of runway remain before Day One actions must be executed to protect value? Options: <2 weeks, 2–4 weeks, 4–8 weeks, 8–12 weeks, >12 weeks

If This Deal Fails to Deliver, Who Loses Sleep?

• If you don’t hit the first 6 months of the deal model, what is the real, non-financial cost you worry about most?
• Which internal or external stakeholders will be held publicly accountable if targets slip? Options: PE operating partner / investment committee, CEO / Board, Divisional president, CFO, Major limited partners, Other
• Which investor or board deadlines create the shortest timelines and highest pressure? Options: Quarterly board review, Semi-annual investor review, Fund exit window, Debt covenant reporting, Other
• What headlines or questions from the board or LPs are you most trying to avoid?
• How would a missed quarter of synergy materially change your next strategic decisions (follow-ons, cost cuts, leadership changes)?

Who's Holding the Keys — Decision Rights and Velocity

• If a critical integration decision needed approval in 48 hours, who actually has the authority and availability to approve it?
• Please list the roles (names or titles) that must sign off on integration trade-offs and approvals.
• Which governance structure are you planning to use for integration oversight? Options: Integration Management Office (IMT), Steering Committee + IMT, Direct CEO/CXO ownership, Ad-hoc (no formal structure yet), Other
• How often will the steering body meet and what is the expected decision turnaround time? Options: Weekly steering / 48–72 hours, Biweekly / 1 week, Monthly / 2+ weeks, Ad-hoc / variable
• Are there any pre-defined veto rights or mandatory approvers that could block fast decisions? Options: Yes — legal/compliance, Yes — major investor(s), Yes — target leadership, No, Unsure
• How are escalation paths documented today for cross-functional disputes? Options: Formal escalation ladder, Informal (known orally), Not defined, Partial / under development

Where the Money Hides — Are Your Synergies Real?

• Which headline synergy lines do you suspect are most optimistic or highest-risk to realize? Options: Headcount / G&A reduction, Vendor consolidation / procurement, IT rationalization, Commercial cross-sell, Pricing alignment, Other, Not sure
• For each top-risk synergy line you selected, what tangible evidence do you currently have (contracts, pilot results, benchmarking)?
• Have these synergies been validated against comparable deals in your industry or by your team’s prior experience? Options: Yes — same industry comparables, Yes — different industry comparables, Partially validated, Not validated
• Which assumptions (volume, price, FTE reductions, vendor rates) create the biggest sensitivity in the model? Options: Volume / demand, Price / margin, FTE reduction timing, Vendor contract terms, Regulatory constraints, Other
• What contingency or confidence reserve (%) is currently allocated to the synergy target? Options: None, <5%, 5–10%, 10–20%, >20%, Unsure
• Who will be accountable for daily tracking and evidence capture against each synergy line?

People You're Afraid to Lose — Talent, Retention, and Knowledge

• Who in the combined organization, if they walked out tomorrow, would most threaten your ability to hit the plan?
• How long have those individuals or teams shown signs of being at risk (e.g., short-tenured, disengaged, fielding counter-offers)? Options: Weeks, 1–3 months, 3–6 months, 6+ months, Not applicable / unknown
• Which retention levers have you designed or deployed so far? Options: Stay bonuses, Equity continuity/refresh, Guaranteed roles/title, Counter-offer processes, No formal plan yet, Other
• What percentage of customer-facing or revenue-critical roles are currently unclear about their Day One reporting structure? Options: 0–10%, 11–25%, 26–50%, 51–75%, 76–100%, Not measured
• Have you mapped critical knowledge transfer points and backups for those roles? Options: Complete mapping, Partial mapping, Planned but not started, Not mapped
• How would you prioritize retention spend relative to IT cutovers or other investments if budget is limited? Options: Prioritize retention, Balance equally, Prioritize systems, Undecided

Systems That Break the Clock — IT, Finance, and Reporting

• Which system migration, if delayed by a quarter, would most jeopardize your ability to consolidate financial reporting or deliver synergies?
• Which systems are critical for financial consolidation and investor reporting? Options: ERP / GL, Billing / AR, Payroll, CRM, HRIS, Inventory / WMS, BI / Reporting, Other
• What cutover windows have been committed (Day One / 30 / 60 / 90 / >90 days)? Options: Day One, 30 days, 60 days, 90 days, >90 days, Not committed
• What is the maximum acceptable downtime for core financial systems without creating investor or regulatory breach? Options: None (real-time required), <4 hours, <24 hours, <72 hours, >72 hours / unacceptable
• Which third-party vendors or integrations are single points of failure for your cutover plans?
• Do you have runbooks, rollback plans, and clear owner checklists for each targeted cutover? Options: Complete and tested, Created but untested, Planned but not created, None

Culture, Customers, and Who Really Wins

• Which cultural shifts or account changes do you believe are most likely to push customers or key partners to leave?
• How will account ownership and coverage change on Day One? Options: No change, Minor reassignments, Major reassignments, Centralized account teams, Other
• Which top customers are on the highest churn watchlist and why?
• What communications plan is in place to reassure customers about continuity and service levels? Options: Executive letters, Joint account meetings, Dedicated transition contacts, No formal plan, Other
• Have you assessed cultural alignment between the two organizations using surveys, leadership interviews, or other diagnostics? Options: Yes — employee survey, Yes — leadership interviews, Partial / informal, No
• What emotional reactions (fear, uncertainty, excitement) have you observed in employees or customers that we should plan around?

Day One That Actually Works — Non‑Negotiables

• If Day One looks like business as usual, what critical protections would you consider failed?
• Which Day One items are absolutely non‑negotiable to protect deal value? Options: Retention communications, Payroll & comp harmonization, Customer communications, IT access & single sign‑on, Reporting consolidation, Compliance filings, Other
• Who will own the Day One command center, and who are the deputies for each major function?
• What acceptance criteria will you use to declare Day One successful for people, systems, and customers?
• Are there regulatory or contractual blockers that must be cleared before Day One actions proceed? Options: Yes — regulatory, Yes — contractual, No known blockers, Unsure
• How will you validate on Day One that employee pay, benefits, and access are correct?

Proof That This Is Working — Metrics, Evidence, and Cadence

• Which single metric, if it moved against you next week, would force an immediate escalation?
• What are the top 5 KPIs you want tracked against the deal model (list in order of importance)?
• How frequently do you want reporting and review cadence during the first 100 days? Options: Daily dashboard, Weekly deep-dive, Biweekly, Monthly executive summary, Other
• At what level of detail do you want evidence to be captured (enterprise, BU, workstream, synergy line item)? Options: Enterprise, Business unit, Workstream, Synergy line item, All of the above
• What types of evidence will you accept to mark a cost or revenue synergy as 'realized'? Options: Signed contract, Invoice/ledger reduction, Payroll change, Customer renewal, Operational KPI improvement, Other
• Who will own ongoing BAU measurement and where should responsibility transfer after handover? Options: Acquirer finance, Divisional ops, Shared services, Third‑party provider, Undecided

What Would Make You Confident to Handover — Next Steps and Mutual Commit

• What specific evidence or condition would make you comfortable transferring day‑to‑day accountability to BAU in 90 days?
• What residual risks must be explicitly documented and accepted before sign‑off?
• Which handover artifacts do you require for acceptance (select all that apply)? Options: Runbooks / SOPs, Dashboards & data definitions, Contracts and vendor lists, Open risk register, RACI & org chart, Audit trail of decisions
• What cadence of post‑handover check‑ins would you expect (and for how long)? Options: Weekly for 12 weeks, Biweekly for 12 weeks, Monthly for 6 months, Quarterly for 12 months, As needed
• Who must be present for the final acceptance review and what signatories are required?
• Looking to 12 months post-closing, what outcome would make you say this integration exceeded expectations?