Start Here: The People, Systems, and Pressure You Live With

• Who are you and which finance role will we be partnering with most closely on this engagement? Options: CFO, VP Finance, Controller, Head of Shared Services, Other
• How large is your finance team (headcount) and how is it structured across AP, AR, GL, close and reconciliations? Options: 1–3, 4–7, 8–15, 16–30, 31+
• Which ERP and ancillary systems do you use today (select all that apply)? Options: NetSuite, Oracle EBS, Sage Intacct, Microsoft Dynamics, Workday Financials, QuickBooks/Online, Custom/Legacy, Other
• How well documented is your chart of accounts, transaction flows, and month-end playbooks today? Options: Comprehensively documented, Partially documented, Outdated documentation, Mostly tribal/undocumented
• If you had to name one immediate pressure driving interest in outsourcing or change, what would it be? Options: Long close cycles, Rising cost of finance headcount, Key-person risk/turnover, PE timeline for reporting, Quality/accuracy issues, Other

Are You Willing to Admit the Close Takes Longer Than It Should?

• How many calendar days does your typical month-end close take from period end to finalized financials? Options: 3–5 days, 6–9 days, 10–14 days, 15–20 days, 21+ days
• How consistent is that cadence month-to-month—do you hit the same timeframe, or does it swing significantly? Options: Very consistent, Some variability, Highly variable, Unpredictable
• Which parts of the close consume the most time or create the biggest bottlenecks? Options: AP processing, AR collections/reconciliations, Intercompany reconciliations, GL adjustments and journal entries, Manual reconciliations, Consolidation/reporting
• When the close slips, what is the single biggest operational or emotional consequence you see in the finance team or leadership? Options: Delayed investor/PE reporting, Cash decision delays, Fire-drill overtime, Stakeholder frustration, Regulatory/tax risk, Other
• Has turnover or a controller departure in the last 18 months exposed single-person dependencies? Tell us what changed and how long that has affected you.
• How often do close days require after-hours work or emergency fixes due to missing documentation or owner availability? Options: Never, Rarely, Sometimes, Often, Always

What Would a Delayed or Flawed Close Cost You—Really?

• If monthly reporting were consistently three business days faster, what decisions or outcomes would that change for your leadership or investors?
• Which of the following consequences feel most likely if reporting quality or timing deteriorated during a transition? Options: Missed covenants or PE deadlines, Late supplier payments, Erroneous external reports, Loss of stakeholder confidence, Cash forecasting errors
• Have you ever lost control of data lineage or found inconsistencies after staff changes—what happened and how long did it take to recover?
• Which senior stakeholders are most sensitive to month-end timing and accuracy (select all that apply)? Options: CFO, CEO, PE/Investor relations, Treasury, Audit/Compliance, Board, Business unit leaders
• When you imagine a negative audit finding or investor pushback tied to close timing, what keeps you awake at night?

Where Do Mistakes Keep Hiding—and Why Don’t They Get Fixed?

• What are the most common exceptions or errors you see in transactional processes (e.g., invoice coding, unapplied payments, reconciliation mismatches)? Options: Incorrect GL coding, Duplicate invoices, Missing backup, Unmatched payments, Cutoff errors, Intercompany mismatches, Other
• How often do those exceptions require escalation to senior accountants or leadership, and what’s the usual resolution time? Options: Rarely, Monthly, Weekly, Daily
• What percentage first-pass accuracy would you estimate your AP and AR processing currently achieves? Options: >98%, 95–97%, 90–94%, 80–89%, <80%
• Which parts of your chart of accounts or transactional rules are most customized or surprising to someone new? Give an example.
• What process knowledge lives in people’s heads today that we would need to capture to avoid corrupting data during handoff?
• When exceptions happen during the close, who typically owns the investigation and sign-off? Options: Controller, Senior accountant, Business unit finance lead, Outsourced/third party, Other

If You Could Protect One Thing During Transition, What Would It Be?

• Which of these is your highest non-negotiable during any outsourcing or transition effort? Options: Data quality/accuracy, Close continuity (no slip), Full chart-of-accounts fidelity, Tight security and access control, Retention of institutional knowledge
• What specific guardrails or governance would make you comfortable handing a process to an external team? Options: SLA-backed close days, Acceptance tests on pilot, Daily issue log and owner, Real-time access to ERP, Named escalation contacts
• How do you prefer responsibility to be split during pilot and rollout (we handle X, you retain Y)?
• Who must sign off on transition milestones in your organization, and what decision criteria do they use?
• If a provider failed to understand your chart of accounts quickly, how would you want that remediated—training, codebooks, shadowing, or something else? Options: Intensive training sessions, Detailed codebooks, Shadowing with side-by-side processing, Iterative accept/reject loops, Other

What Would Faster, Cheaper, or Safer Actually Look Like for You?

• Which outcomes would you prioritize if forced to choose the top two? Options: Reduce close days, Lower cost per transaction, Eliminate single-person dependencies, Improve first-pass accuracy, Faster month-end insights/reporting
• Can you put numbers to those priorities—for example a target close day reduction, cost savings goal, or accuracy improvement?
• Which KPIs will you use to judge whether a pilot or outsourced operation is successful? Options: Close days, First-pass accuracy, Cost per transaction, Exception rate, Time to resolve exceptions, SLA adherence
• How would achieving these targets change the CFO’s or PE owner’s view of the finance function?
• What would failure look like to you—and what would be the immediate consequence?

A Pilot Is Only Convincing If It Mirrors Reality—What Must We Include?

• Which process would be the best pilot to validate overall fit (pick one): AP, GL close entries, reconciliations, AR cash application, or another? Options: AP, GL journal entries/close, Reconciliations, AR cash application, Other
• What sample volume and timeframe would you consider statistically and operationally meaningful for a pilot? Options: 2–4 weeks, 1 month, 1 quarter, Other
• What pilot acceptance criteria would make you confident to expand (select all that apply)? Options: X days saved, Y% accuracy, Z% SLA adherence, No material reporting errors, Stakeholder satisfaction
• Who from your team will be responsible for running, evaluating, and signing off on pilot results?
• What ERP access and data extracts would we need to run the pilot realistically (e.g., AP invoices, chart of accounts, open AR items)? Please list any security constraints.

Timing, Communication, and the Close—How Do We Avoid Making Things Worse Before They Get Better?

• During which days of the month is your team absolutely unavailable for change work (blackout windows)? Options: Last 5 days of month, First 5 days after month, Entire close week, No blackout
• What time zone constraints or SLA hours are critical for you to keep during close periods? Options: Same business hours, Overlap with AP/US hours, 24-hour coverage needed, Other
• What cadence of governance and status reporting will reassure you—daily standups, weekly executive updates, or something else? Options: Daily standups, Twice-weekly syncs, Weekly updates, Monthly executive review, Ad-hoc escalations
• Who will be the day-to-day contact and who are the escalation contacts on your side? Please include role and email if possible.
• What documentation or samples can you share up front to accelerate onboarding (e.g., COA, last 3 months close checklists, vendor master file)?

Hidden Blockers: What's Lurking Under the Surface?

• Has your organization attempted outsourcing or major process change before? If so, what went well and what failed? Options: Yes—successful, Yes—partially successful, Yes—failed, No previous attempts
• What internal resistance do you anticipate from the finance team or business units, and why might they push back?
• Are there contractual, regulatory, or industry-specific constraints we should know about before designing a pilot? Options: SOX/controls, PE reporting covenants, Tax filing constraints, Industry compliance, None of the above
• Are there migration or integration risks (AP vendor portals, bank integrations, proprietary connectors) that have caused problems in the past?
• If you had to flag one potential derailment we should monitor closely during rollout, what would it be and why?

Deciding Together: When and How Do We Move Forward?

• What is your ideal timeline to make a decision about piloting an outsourced solution? Options: Immediately, Within 30 days, 60–90 days, 3–6 months, Undecided
• Who are the decision-makers and approvers we need to engage, and what will each person care about most?
• What budget or costing constraints will shape the scope of any pilot or phased adoption? Options: Fixed budget, Flexible within ROI, Requires business case, Undetermined
• Would you be open to a short proof-of-concept on a single process to validate core concerns (ERP familiarity, COA mapping, accuracy)? Options: Yes—ready now, Yes—within 30 days, Maybe later, Not interested
• What would be a comfortable next step after this discovery call—pilot scoping, executive briefing, or a technical deep-dive? Options: Pilot scoping, Executive briefing, Technical deep-dive, Share more documentation first

• Pilot Kickoff & Current-State Confirmation
• Pilot Design & Chart-of-Accounts Mapping Workshop
• Pilot Dry Run & Tool Configuration Validation
• Pilot Execution Daily Standup (template)
• Pilot Review, Validation & Acceptance Decision

• Log every exception with owner, root cause hypothesis, and remediation ETA.
• Prove technical readiness: connectors, mapping, and automation operate on customer data.
• Validate exception handling and escalation procedures work end-to-end.
• Identify and schedule fixes for any gaps found in the dry run.
• Seller to remediate configuration issues and deliver updated mapping/configuration package.
• Customer to re-run or approve corrected samples if remediation affects mappings.
• Confirm go/no-go date for live pilot start based on remediation completion.
• Quick Status Snapshot
• Keep pilot on target by removing daily blockers and enforcing SLAs.
• Rapidly surface systemic data-quality issues that require mapping or process changes.
• Ensure stakeholders are aware of any risks to acceptance and can act swiftly.
• Introductions & Objectives
• Seller to implement immediate quick-fixes and communicate impact to customer.
• If an escalation is triggered, assign exec sponsor and set a 24‑hour remediation checkpoint.
• Customer to deliver formal acceptance sign-off or a prioritized remediation list within agreed timeline.
• Executive Summary of Pilot Results
• Demonstrate measurable proof that the future state is achieved against the pilot KPIs.
• Obtain explicit customer validation for each acceptance criterion (force yes/no).
• Agree either acceptance sign-off or a prioritized remediation plan with owners and timelines.
• Establish next-phase scope, timeline, and governance if accepted.
• Seller to produce the final pilot report with KPI trends, exception analysis, and recommended remediation for any failures.
• If accepted, create phase‑1 rollout plan with owners, timelines, and parallel-processing dates.
• A single, validated current-state sentence that all participants accept.
• Explicit, quantified consequence (baseline metrics) documented for comparison.
• Clear, operational future-state definition and acceptance criteria for the pilot.
• ERP access and CoA extract responsibilities assigned with deadlines.
• Customer to provide CoA extract, sanitized transactions for sample period, and ERP read-access credentials.
• Seller to deliver proposed one-sentence current & future state summary for sign-off.
• Schedule Pilot Design & Mapping Workshop and designate SME attendees.
• Process Walk-through with Customer Context
• Detailed, signed-off CoA-to-process mapping for the pilot scenario.
• A complete exceptions matrix with owner and handling rules.
• Explicit KPIs and acceptance tests to be measured during the pilot.
• Customer confirmation that mappings and rules reflect real operational intents.
• Seller to produce the CoA mapping document and exceptions matrix and circulate for customer sign-off.
• Customer to flag any additional edge-case transactions and provide sample records.
• Agree and publish pilot KPI dashboard template and reporting cadence.
• Environment & Connector Verification
• Execute Mock Transactions Through Mapping
• Deep Dive on Exceptions & Root Causes
• Crystal Current-State Statement
• Top 3 Blockers / Exceptions
• Chart-of-Accounts & Mapping Exercise
• Escalations & Time‑sensitive Items
• Quantify Consequence / Baseline Metrics
• Tie Results to Consequences
• Exception Workflow Test
• Identify and Document Exceptions / Edge Cases
• Customer Validation & Forced Confirmation
• Monitoring & Dashboard Check
• Define Target Future State (one sentence)
• Define KPIs, Acceptance Tests, and Reporting Templates
• Data Quality Observations & Quick Wins
• Acceptance Decision & Next Steps
• Issue Triage & Remediation Plan
• Access, Data & Chart-of-Accounts Confirmation
• Validation Checkpoint
• Pilot Scope, Timeline, and Acceptance Criteria
• Next Steps & Responsibilities

• Accounts Payable Invoice Processing and Payment Execution
• Automated AP Exception Triage and Resolution
• Vendor Statement Reconciliation and Dispute Management
• Accounts Receivable Invoicing and Collections
• Cash Application and Lockbox Posting
• Bank Reconciliations and Cash Confirmations
• General Ledger Journal Entry Posting
• Month-End Close Execution and Journal Entries
• Balance Sheet Account Reconciliations
• Fixed Asset Accounting and Depreciation
• Intercompany Reconciliation and Settlement
• Monthly Management Financial Reporting Pack
• Payroll Processing and Statutory Filings
• Tax Compliance Support and Return Preparation

Accounts Payable Invoice Processing and Payment Execution

• What is your average monthly invoice volume? Options: Less than 500, 500-2,000, 2,001-10,000, More than 10,000
• Which invoice receipt channels do you actively receive? Options: Email/PDF, Paper/Mail, EDI/CSV, Supplier Portal, Other
• Which ERP(s) and version(s) are used for AP posting? (list all)
• Which payment methods do you use or require support for? Options: ACH, Wire, Check, Virtual Card (VCard), Supplier Portal Payment, Other
• What is your target SLA from invoice receipt to payment execution? Options: Same business day, 1-3 business days, 4-7 business days, Depends by vendor/term
• Are there special approval workflows, multi-approver thresholds, or delegated limits we should know about? Describe exceptions.

Automated AP Exception Triage and Resolution

• What percent of invoices typically trigger exceptions (e.g., missing PO, price variance)? Options: Less than 1%, 1-5%, 6-15%, More than 15%
• What are the top 3 exception types you see most often?
• Do you have an existing escalation path and owners for AP exceptions? Options: Yes, No
• How quickly must exceptions be resolved during close periods? Options: Same day, 1-2 business days, 3-5 business days, No strict SLA
• Do you permit automated resolution rules (e.g., match on partial fields) or require human review for all exceptions? Options: Automated rules allowed, Human review required for all, Hybrid — automated with human override
• Please describe any audit, approval, or documentation requirements for exception handling (e.g., retention, approval logs).

Vendor Statement Reconciliation and Dispute Management

• How many vendor statements are reconciled each month? Options: Less than 50, 50-250, 251-1,000, More than 1,000
• How often do you receive vendor statements vs. EOM reports from vendors? Options: Monthly, Quarterly, Ad hoc, We do not routinely receive statements
• What percentage of reconciliations typically result in disputes or open items? Options: Less than 1%, 1-5%, 6-20%, More than 20%
• Who currently owns vendor dispute communications (AP team, procurement, vendor reps)? Options: AP team, Procurement, Shared between teams, Other
• Do you require vendor-facing portals or standardized dispute templates? Options: Yes — portal preferred, Yes — templates only, No
• Are there specific cutoffs or aging buckets you use to prioritize disputes (e.g., 30/60/90)?

Accounts Receivable Invoicing and Collections

• Which billing types do you issue (e.g., subscription/monthly, project-based, PO-based, one-time)? Options: Subscription/Recurring, Project/Time & Materials, PO-based, One-time/Ad hoc, Other
• How are invoices created and delivered today? Options: ERP-generated / emailed, Third-party billing tool, Manual PDF uploads, Customer portal, Other
• What is your current DSO (days sales outstanding) target or typical range? Options: Less than 30, 30-45, 46-60, More than 60
• Do you require collections segmentation (e.g., automated reminders, high-touch AR reps)? Options: Yes — segmented approach, No — same process for all, Need recommendation
• How are credit memos and disputes routed and approved today?
• Which KPIs or reports do you need from collections (aging, promise-to-pay, dispute aging)? Options: Aging by customer, Promise-to-pay tracking, Dispute aging, Cash forecast, Custom KPIs

Cash Application and Lockbox Posting

• Do you use a bank lockbox, virtual lockbox, or direct remittance channels? Options: Bank lockbox, Virtual lockbox, Direct ACH/Bank file, No lockbox
• What percent of payments are electronic vs. check? Options: Mostly electronic (>75%), 50-75% electronic, 25-50% electronic, Mostly checks (>75%)
• What remittance file formats or standards do you receive (e.g., BAI2, CSV, proprietary)? Options: BAI2, CSV/Excel, ERP-specific format, PDF remittances, Other
• What match rate do you currently achieve for automated application? Options: >95%, 85-95%, 70-85%, <70%
• What is acceptable unapplied cash aging before escalation? Options: Same day, 1-3 business days, 4-10 business days, 30+ days
• Describe any exceptions that require research (e.g., unidentified remittances, partial payments).

Bank Reconciliations and Cash Confirmations

• How many bank accounts require reconciliation each month? Options: 1-5, 6-20, 21-50, More than 50
• What is the required cadence for bank reconciliations (monthly/weekly/daily)? Options: Daily, Weekly, Monthly, Quarterly
• Do you receive electronic bank statements (e.g., BAI2) or PDFs? Options: Electronic (BAI2/MT940), PDF statements, Both, Manual bank feeds
• Are there material outstanding items that require research (e.g., uncleared items, long-dated reconciling items)? Options: Yes, No
• Who approves reconciling items and adjustments and how are approvals evidenced?
• Do you require bank confirmations for audit or intercompany purposes? If yes, frequency. Options: Yes — annually, Yes — quarterly, Yes — monthly, No

General Ledger Journal Entry Posting

• How many manual journal entries are posted monthly on average? Options: Less than 50, 50-250, 251-1,000, More than 1,000
• Do you use recurring templates for journals (accruals, allocations) and what percent are automated? Options: Most recurring automated, Some automated, Manual templates only, No recurring journals
• Are there strict approval workflows or segregation of duties requirements for JE posting? Options: Yes — strict approvals, Moderate controls, Minimal controls
• What cut-off times or blackout windows exist during month-end for posting?
• Do journal entries require supporting schedules or source documents stored in a document repository? Options: Yes — repository required, Not required, Ad hoc
• Do you require automated recurring entries for allocations, chargebacks, or shared services? Describe frequency.

Month-End Close Execution and Journal Entries

• What is your current close-to-close cycle (days from period end to finalized books)? Options: Less than 5 days, 5-10 days, 11-15 days, More than 15 days
• Which activities are your top close bottlenecks? Options: Reconciliations, Journals & approvals, Intercompany, Sub-ledger reconciliations, Other
• Do you require a parallel-run period before full cutover for the close process? Options: Yes — one quarter, Yes — one month, No
• Which deliverables must be produced at close (trial balance, FS, management pack, commentary)?
• What acceptance criteria would you set for a pilot to validate month-end close support (e.g., reduce close days by X, zero recon discrepancies)?
• Are there blackout dates or PE reporting windows where disruption is unacceptable? Options: Yes — specific dates, No

Balance Sheet Account Reconciliations

• How many balance sheet accounts require monthly reconciliation? Options: Less than 50, 50-200, 201-1,000, More than 1,000
• Do you maintain minimum materiality thresholds for reconciliation items? Options: Yes — dollar thresholds, Yes — percentage thresholds, No
• What template or documentation does each reconciliation require (e.g., lead schedules, variance explanations)?
• Who performs sign-off and what is the expected sign-off cadence? Options: Account owner monthly, Controller review monthly, Quarterly sign-off, Other
• Do you have historical reconciliation backlog or long-open reconciling items that must be cleared during transition? Options: Yes — significant backlog, Some backlog, No
• Do you require reconciliation automation tools or integration with your ERP? Options: Yes — full automation, Partial automation, No

Fixed Asset Accounting and Depreciation

• Which fixed asset system or register do you use (ERP module, third-party FA software, spreadsheet)?
• Approximately how many fixed assets and active asset records do you maintain? Options: Less than 1,000, 1,000-5,000, 5,001-25,000, More than 25,000
• What is your capitalization threshold and are there multiple thresholds by asset type?
• Which depreciation methods do you use (e.g., straight-line, declining balance, unit of production)? Options: Straight-line, Declining balance, Units of production, Custom/multiple methods
• How frequently do you record asset additions, disposals, and transfers? Options: Real-time/monthly, Monthly, Quarterly, Ad hoc
• Do you require physical asset verification or tagging as part of the service? Options: Yes — required, Optional, No

• Master Services Agreement (MSA)
• Statement of Work (SOW)
• Service Level Agreement (SLA)
• Pricing & Commercial Schedule
• Payment & Invoicing Terms
• Acceptance Tests & Pilot Sign-off
• Data Processing Agreement (DPA)
• Security & Compliance Addendum
• Chart of Accounts Mapping & Data Migration Annex
• Transition Governance Plan
• Knowledge Transfer & Onboarding Plan
• Change Order & Scope Amendment Process
• Exit, Continuity & Transition Assistance

• Success Signals Validation
• Runbooks & SOP Handoff
• Shared Channel & Escalation Setup
• Close-Period War Room & Post-Close Retrospective
• Continuous Improvement & Quarterly Optimization Planning

• Publish a post-close issues log with root-cause analysis, owners, and remediation dates.
• Agree escalation paths and SLAs so issues during close periods are resolved within acceptable timeframes.
• Establish alerting and on-call coverage to eliminate time-zone gaps during critical windows.
• Provision the shared channel, add members, and publish channel use guidelines.
• Publish the escalation matrix and configure alerting to on-call responders.
• Document and distribute quick triage playbooks and link to runbooks.
• Pre-Close Readiness Check
• Ensure the close occurs with minimal disruption through a defined war room and role clarity.
• Capture factual post-close lessons and validate corrective actions with stakeholders.
• Ensure immediate updates to runbooks and a tracked backlog of improvements are created.
• Confirm war room schedule and on-call rosters for the next close and distribute to stakeholders.
• One-sentence Current State & Consequence
• Apply agreed runbook changes and notify the team of version updates before the next close.
• One-sentence Future State Target
• Prioritize a clear set of CI initiatives tied to expected reductions in close days, errors, or cost.
• Frame pilots with explicit acceptance criteria so each experiment proves the future state.
• Establish governance cadence and KPI owners for ongoing measurement and accountability.
• Publish the prioritized CI backlog with impact estimates, owners, and target dates.
• Kick off any approved pilots with documented acceptance criteria and checkpoints.
• Configure or update the KPI dashboard and assign dashboard owners for quarterly reporting.
• Confirm whether the engagement meets the predefined success signals and obtain formal customer acceptance or documented remediation plan.
• Ensure every KPI variance is tied to a clear cause and owner for resolution.
• Create an auditable record of acceptance decisions and follow-up actions.
• Deliver a KPI measurement pack (baseline vs current) including data sources and calculation logic.
• If gaps exist, produce a remediation plan with owners, milestones, and success metrics for follow-up validation.
• Capture signed acceptance or escalation to executive sponsor if acceptance criteria are not met.
• Runbook Overview & Version Statement
• Ensure runbooks map to real scenarios and explicitly prevent the previously documented failure modes.
• Obtain customer confirmation on runbook completeness and agree the training schedule and sign-off criteria.
• Establish clear version control and ownership for ongoing updates and audits.
• Publish the final runbook package to the agreed repository and notify stakeholders.
• Schedule and document knowledge-transfer sessions and collect attendee sign-offs.
• Log any outstanding edge cases to the backlog with owners and target resolution dates.
• One-sentence Communication Protocol
• Create an agreed shared channel with the right membership and permissions for real-time collaboration.
• Channel & Access Setup
• Trend Review & Opportunity Sizing
• Before/After KPI Presentation (Proof)
• Live War Room Protocol
• Walkthrough: Critical Close Processes (Proof/Tie-back)
• Prioritization & Roadmap
• Gap Analysis and Root Causes
• Escalation Matrix & SLAs
• Exceptions & Edge Cases
• Post-Close Retrospective (Diagnosis -> Proof -> Validation)
• Update Runbooks and Backlog
• Knowledge Transfer & Training Plan
• Acceptance Criteria Check
• Alerting, On-call Roster & Close-period Standby
• Pilot Planning & Acceptance Criteria
• Ongoing Maintenance & Audit Trail
• Operational Playbooks for Triage
• Decision and Next Steps
• Governance & KPIs for Next Quarter