Getting Comfortable — Tell Us About You

• How many active leases does your team currently manage? Options: Fewer than 50, 50–150, 151–300, 301–500, More than 500
• What types of properties make up the majority of your portfolio? Options: Office, Retail, Warehouse/Distribution, Industrial, Mixed-use, Other
• Which regions or states contain most of your leases?
• Who on your team is primarily responsible for lease tracking day-to-day? Options: Lease Administrator, Director of Real Estate, Corporate Real Estate Ops, Accounting/Finance, External Consultant, No single owner
• What was the trigger that pushed you to look for a system of record for leases now? Options: Missed critical date, Audit finding, ERP accounting requirements, Scaling growth, Merger/Acquisition, Other
• Briefly describe a recent moment when lease tracking caused stress or an emergency for your team.

Are We Quietly Running Toward a Bigger Problem?

• Which single recurring issue causes you the most pain—missed options, overpayments, audit surprises, or something else? Options: Missed renewal/termination dates, Overpaid rent/escalations, Audit/lease accounting findings, Invoice/PO mismatches, Lack of centralized records, Other
• How often do these issues surface in a way that requires executive attention? Options: Weekly, Monthly, Quarterly, Annually, Rarely
• Tell us about the most costly example in the last 24 months—what happened and what was the impact?
• When problems occur, how do they typically get discovered? Options: Internal review, External audit, Vendor notice, Tenant/landlord dispute, Random catch by staff, Other
• How does it feel inside the team when a critical lease issue appears (e.g., embarrassed, blamed, panic, resigned)? Options: Panic/urgent, Embarrassed/defensive, Blame/point fingers, Resigned/used to it, Motivated to fix, Other

Where Process Turns Into Risk

• Why do critical dates and calculations routinely fall through the cracks in your current process?
• Which tools or systems are currently used to track leases and critical dates? Options: Excel/Google Sheets, Shared drives, Custom database, Point lease software (name), ERP/Accounting only, None
• Who is the single source of truth when someone questions a lease term today? Options: Spreadsheet owner, Lease administrator, Finance contact, Legal, No single source
• How frequently do you reconcile rent and liability calculations today? Options: Monthly, Quarterly, Annually, On audit only, Never
• What manual steps in your current process consume the most time or cause the most errors?

Who Holds The Keys — Decision & Approval Dynamics

• If this project fails to deliver, whose career or budget is most at risk?
• Which of the following roles will influence or approve a purchase decision? Options: Head of Real Estate, CFO/Controller, Lease Administrator, Procurement, Legal, IT/Security, External Auditor
• Who is the ultimate decision-maker for purchasing new lease software? Options: Real Estate Director, CFO, Procurement Head, IT Director, Committee/Steering Group, Unsure
• How long is your typical procurement/approval cycle for software of this size? Options: Less than 1 month, 1–2 months, 3–4 months, 5–6 months, Longer than 6 months
• Which internal stakeholder is most likely to block or slow the project, and why?
• Do you have an internal champion already willing to drive the project across teams? Options: Yes — named person, Yes — unnamed, No

What Would Real Success Actually Feel Like?

• If the new system solved one big thing for you, which outcome would you care about most? Options: Zero missed critical dates, Accurate lease accounting outputs, Reduced time spent on reconciliations, Single searchable lease record, Fewer audit findings, Other
• Which measurable KPIs would you use to judge a successful implementation? Options: % missed dates eliminated, % error reduction in calculations, Hours saved per month, Audit findings reduced, User adoption rates, Other
• What timeline would make the outcome feel urgent versus acceptable? Options: Immediate (30 days), Short (2–3 months), Normal (3–6 months), Flexible (6+ months)
• What financial or reputational constraints shape how big a success looks to your leadership?
• Who needs to see which metrics and how often to feel confident the program is working? Options: Real Estate Ops weekly, Finance monthly, Executive quarterly, Audit on-demand, Other

Can Your Accounting Sleep at Night?

• How confident are your finance and audit teams in the current lease liability numbers (ASC 842 / IFRS 16)? Options: Very confident, Somewhat confident, Unsure, Not confident
• Which accounting or ERP systems must this solution integrate with? Options: Oracle, SAP, NetSuite, QuickBooks, Workday Financials, Other/Custom
• Have auditors in the past required a system of record for lease accounting or presented findings tied to manual processes? Options: Yes — formal finding, Yes — informal recommendation, No
• How do you currently produce lease accounting outputs—manual spreadsheets, scripts, ERP module, or third-party service? Options: Manual spreadsheets, Custom scripts/tools, ERP lease module, External consultant, Other
• Describe any recurring calculation issues you've experienced (e.g., misapplied escalation caps, incorrect CPI indexing, wrong commencement dates).

Data Reality Check — What We Can Actually Work With

• If we asked for a representative sample of leases today to validate abstraction, how long would it take to assemble? Options: Less than 48 hours, 3–7 days, 1–2 weeks, More than 2 weeks, Not possible right now
• Where are your lease documents currently stored? Options: Local file servers, SharePoint/Drive, Email inboxes, Property manager files, No central repository
• What percentage of your leases do you believe have complete, signed documents available? Options: 0–25%, 26–50%, 51–75%, 76–90%, 90–100%
• Which file formats and annotations should we expect (PDF scans, editable PDFs, redlines, scanned signatures)? Options: Searchable PDFs, Scanned images, MS Word, Redlined documents, Signed PDFs, Other
• Who owns lease document collection and validation inside your organization? Options: Real Estate Ops, Legal, Property Management, Third-party vendor, No clear owner
• Are there confidentiality, data residency, or security rules that would affect how we handle your lease files? Options: Yes — strict, Yes — moderate, No

Constraints, Non‑Negotiables, and Deal‑Breakers

• What single non-negotiable would stop this project outright (e.g., audit compliance, security certification, budget ceiling) if unmet?
• Within these areas, which constraints are most binding for you? Options: Budget limits, Implementation timeline, Security/compliance, Integration complexity, Staff bandwidth, Legal/contract requirements
• What is your approximate budget range or internal price expectation for a per-lease solution and implementation? Options: Under $10k, $10k–$50k, $50k–$150k, $150k–$300k, Flexible/undisclosed
• Are there contract terms or SLA needs that would be deal-breakers (e.g., uptime, data deletion, liability caps)?
• How important is vendor-provided abstraction and migration versus in-house handling? Options: We need full vendor abstraction, Prefer vendor help + our validation, We will handle abstraction ourselves, Undecided
• What internal timing constraints (e.g., fiscal close, audit window, lease seasonality) must the project respect?

Small Steps That Build Trust — Pilot and Acceptance

• What would a low-risk pilot look like to you—a small subset of leases, a single region, or one property type? Options: Sample 10–20 leases, Single region/state, One property type (e.g., retail), Full accounting reconciliation pilot, Other
• How many leases would you consider sufficient to validate abstraction accuracy and alert fit? Options: 5–10, 11–25, 26–50, 50+
• What acceptance criteria would you require before declaring a pilot successful? Options: >95% abstraction accuracy, No missed dates during pilot, Reconciled accounting outputs, Stakeholder sign-off, Other
• Who must sign off on pilot acceptance and what is their expected timeline for review?
• What internal resources can you commit to a pilot (time in hours/week, named owners, IT access)?
• Would you be open to a brief technical demo populated with a few of your sample leases before committing to a pilot? Options: Yes — ready now, Yes — in a few weeks, Maybe, No

Taking The Next Small Step Together

• If we agree on a small pilot, what is the earliest realistic start date for your team? Options: Immediately (within 2 weeks), In 1 month, 2–3 months, Later than 3 months, Undecided
• Who should be our single point of contact for coordinating sample collection, technical access, and pilot logistics?
• What would make you say 'this was worth it' after the first 30 days of working together?
• What concerns would you want us to address before moving from pilot to full implementation?
• How do you prefer we communicate progress during discovery and pilot (email summaries, weekly calls, shared dashboard)? Options: Email summaries, Weekly calls, Bi-weekly meetings, Shared dashboard, Ad-hoc messaging
• Any final context, documents, or sensitivities we should know before we request sample leases or schedule the next meeting?

• Pre-Experience Alignment (Pre-Work Confirmation)
• Lease Abstraction Validation Workshop
• Alerts & Workflow Fit Session (Scenario Simulations)
• Accounting Integration & Calculation Validation
• Solution Experience Review & Go/No-Go Decision

• Identify and assign fixes for any mapping or calculation gaps with timelines.
• Confirm crystal-clear current state, explicit consequence, and defined future-state outcomes.
• Introductions & Objectives
• Brief Recap: Problem → Consequence → Outcome
• Prove abstraction accuracy against real leases and reach agreement on per-field acceptance or required remediation.
• Identify and prioritize systematic extraction errors and assign remediation owners.
• Produce a short remediation plan and timeline that, when executed, will achieve the future state for abstraction completeness.
• Seller: Deliver an exception register listing affected leases, root cause, proposed fix, and ETA for each item.
• Customer: Provide missing pages/clarifications for specific leases flagged during walkthrough.
• Seller: Implement agreed rule updates or schedule manual abstraction passes and notify customer of changes.
• Context: Which missed-deadline or approval failures are we preventing?
• Validate that alerts trigger correctly for representative scenarios and tie directly to the customer's stated consequences.
• Confirm approval workflows map to the customer's org and SLAs, or capture required changes.
• Produce a list of configuration changes and test cases to close any gaps before deployment.
• Seller: Update alert configurations and workflow routing based on agreed changes and provide a retest timeline.
• Customer: Confirm role owners and escalation contacts for the workflow test cases.
• Seller & Customer: Create a prioritized test-case list to validate post-config changes.
• One-sentence Accounting Problem & Desired Outcome
• Validate that calculations and mapped outputs meet accounting expectations and support auditability.
• Agree on reconciliation method and pass/fail criteria for migration cutover.
• Seller: Deliver updated mapping documentation and corrected export files for the sample leases flagged.
• Customer: Provide sample sandbox credentials or ledger import test window and expected result files for reconciliation.
• Seller & Customer: Run a reconciled test import and sign off on journal-level acceptance before deployment.
• Summary: Current State, Consequence, and Future State
• Obtain explicit customer confirmation that the solution achieves the future state or agree an acceptable remediation plan.
• List all remaining risks and owners with timelines sufficient to proceed to Solution Scope.
• Schedule the Solution Scope meeting and align on required inputs for contractual/commercial discussions.
• Customer: Provide formal acceptance or conditional acceptance with documented outstanding items and priority.
• Seller: Produce a concise Solution Experience report summarizing evidence, remediation plan, and recommended Scope items.
• Both: Book the Solution Scope meeting and circulate pre-read materials aligned to the accepted remediation plan.
• Agree and collect the exact sample lease set and representative scenarios to be used in validation.
• Set concrete success metrics and logistics so live validation proves outcomes rather than demonstrates features.
• Assign owners and pre-work to ensure readiness for the workshops.
• Customer: Share the confirmed sample lease files and a brief 'ground-truth' spreadsheet mapping expected key terms and values.
• Seller: Prepare the abstraction outputs for the sample leases and a mapping of fields to be demonstrated.
• Customer & Seller: Confirm meeting schedule, access credentials, and test data transfer by X date.
• Proof Digest: Key Evidence
• Abstraction Summary Metrics
• Current State Statement (CRYSTAL CLEAR)
• Review Configured Alert Rules
• Mapping Review
• Simulate Scenario A: Renewal Window Miss
• Consequence Quantification
• Live Walkthrough: Representative Lease 1 (Complex Escalation)
• Open Items & Remediation Plan
• Calculation Demonstration
• Acceptance Checkpoint
• Future State Definition
• Simulate Scenario B: Escalation Cap Breach
• ERP Import Simulation / Export Review
• Live Walkthrough: Representative Lease 2 (Options/Renewals)
• Reconciliation & Acceptance Criteria
• Role Mapping & Approval Hierarchy
• Exception Pattern Review
• Decision & Next Steps
• Sample Dataset Review & Scenario Selection
• Remediation Path & Timeline
• Open Discrepancies & Remediation Plan
• Success Criteria, Acceptance Thresholds, and Logistics
• Gap Identification & Quick Fixes

• Collect and Index Lease Documents
• Scan and OCR Lease Paperwork
• Professional Lease Abstraction into Database
• Import and Clean Spreadsheet Lease Data
• Configure Critical Date Alerts and Notifications
• Set Role-Based Approval Workflows
• Configure Rent Schedules and Escalation Rules
• Automated Rent and CAM Charge Calculations
• Generate ASC 842/IFRS 16 Accounting Reports
• Integrate with ERP and Accounting Systems
• Export Journal Entries and Amortization Schedules
• Train Real Estate and Finance Teams on Platform

Collect and Index Lease Documents

• How many active and archived leases will need to be collected and indexed? Options: <50, 50-100, 101-500, 501-1,000, 1,000+
• Where are your lease documents currently stored? Options: Local file shares, Google Drive/Workspace, SharePoint/OneDrive, Lease closets/physical boxes, Multiple locations, Other
• Do you have a standardized naming and folder structure for lease documents today? Options: Yes, No, Partially
• Are scanned images and PDFs for each lease complete (e.g., all exhibits, amendments, riders)? Options: Complete, Partial, Mostly missing exhibits, Unknown
• Who will own collection tasks and provide physical/virtual access to documents?
• Are there confidentiality or redaction requirements before indexing (PII, tenant-sensitive clauses)? Options: Yes, No, Unknown

Scan and OCR Lease Paperwork

• Approximately how many pages of physically held lease paperwork require scanning? Options: None, <1,000, 1,000-5,000, 5,001-20,000, 20,000+
• What document quality do you expect (handwritten, typewritten, poor photocopies)? Options: High quality digital PDFs, Mixed (handwritten + typed), Low quality/photocopies, Unknown
• Do leases include non-English text that requires OCR language support? Options: English only, Spanish, French, Other, Multiple languages
• Do you require automated redaction of sensitive data during OCR processing? Options: Yes, No
• Would you like OCR output to be validated by humans before indexing? Options: Yes, full QA, Spot check QA, No, automated only
• Are there preferred file naming or metadata fields to capture at ingestion (e.g., lease ID, location, landlord)?

Professional Lease Abstraction into Database

• How many leases should be professionally abstracted as part of this engagement? Options: <50, 50-100, 101-250, 251-500, 500+
• Which abstraction model do you require (full term-level abstraction, summary-level, or hybrid)? Options: Full (all clauses/exhibits), Summary (key terms only), Hybrid (key terms + select exhibits)
• Who is responsible for abstraction: your internal team, vendor professional services, or a hybrid approach? Options: Customer-led, Vendor-led, Hybrid
• What SLA and accuracy acceptance threshold do you require for abstractions (e.g., 98% field accuracy)? Options: 95%, 96-97%, 98%, 99%+, Custom/Discuss
• Do you need capture of historical amendments, options, and exhibit-level dates and clauses? Options: Yes, all historical items, Yes, but limited to last X years, No, only current effective terms
• Are there custom fields or business rules we must capture during abstraction (e.g., internal asset codes, cost centers)?

Import and Clean Spreadsheet Lease Data

• Do you currently maintain lease data in spreadsheets that must be imported? Options: Yes - single spreadsheet, Yes - multiple spreadsheets, No
• How many spreadsheet line items or lease records will need import and mapping? Options: <50, 50-100, 101-500, 501-1,000, 1,000+
• What common inconsistencies exist (missing fields, duplicate leases, inconsistent IDs)? Options: Missing fields, Duplicates, Inconsistent IDs, Incorrect dates/values, All of the above, Other
• Do you require data normalization (e.g., standardizing landlord names, address formats)? Options: Yes - full normalization, Yes - partial, No
• Do you need help mapping spreadsheet columns to platform fields? Options: Yes - full mapping assistance, Yes - occasional guidance, No - we will map
• Who will be the point of contact for spreadsheet validation and sign-off?

Configure Critical Date Alerts and Notifications

• Which critical date types should trigger alerts (e.g., renewals, options, rent escalation effective dates)? Options: Renewal, Option Exercise, Notice to Vacate, Rent Escalation, Commencement, Other
• What default lead times are required for each alert type (e.g., 90/60/30 days)? Options: 7 days, 30 days, 60 days, 90 days, Custom
• Which delivery channels should be used for alerts (email, in-app, SMS, Slack)? Options: Email, In-app, SMS, Slack/Microsoft Teams, Other
• Who should receive and own these alerts (role names or individual emails)?
• Do alerts require attachments or contextual lease excerpts to be included? Options: Yes, No
• Do you need configurable escalation or acknowledgement tracking for missed alerts? Options: Yes, No

Set Role-Based Approval Workflows

• How many distinct approval roles or levels exist in your lease decision process? Options: 1-2, 3-4, 5-6, 7+
• Do approvals depend on thresholds (e.g., rent increase > X%, lease value > $Y)? Options: Yes, No
• Should external parties (lawyers, landlords) be included in workflows? Options: Yes, No, Sometimes
• Do you require parallel approvals (multiple approvers same stage) or sequential only? Options: Sequential, Parallel, Both
• Do you want audit trail and time-to-approve SLAs captured for each workflow action? Options: Yes, No
• Are there site- or region-specific workflow variations we must configure? Options: Yes, No, Unknown

Configure Rent Schedules and Escalation Rules

• What types of rent schedules exist in your portfolio (flat, step, CPI-indexed, percentage of sales)? Options: Flat, Step/Fixed Increases, CPI-indexed, Percentage of Sales, Other
• Do escalations include caps, floors, collars, or complex calculation clauses? Options: Caps, Floors, Collars, Complex/legal clauses, None
• How should free rent, rent abatement, or rent holidays be modeled? Options: As explicit rent schedule lines, As offsets/credits, Manual adjustments only, Other
• Do you require tenant percentage rent triggers and reconciliations? Options: Yes, No, Not applicable
• Are there bespoke escalation calculation examples we should test during configuration? Options: Yes - will provide examples, No
• Who owns approval of configured rent schedules and escalation rules?

Automated Rent and CAM Charge Calculations

• Which charge types need automated calculation (base rent, CAM, taxes, insurance, utilities)? Options: Base Rent, CAM, Property Taxes, Insurance, Utilities, Other
• Do CAM calculations require reconciliations to landlord statements or detailed expense ledgers? Options: Yes - full reconciliation, Yes - summary reconciliation, No
• How should proration, retroactive adjustments, and backbilling be handled? Options: Auto-calculate and post, Calculate for review then post, Manual only
• Are there tenant-specific caps or exclusions (e.g., excluded expense categories)? Options: Yes - many, Yes - few, No, Unknown
• Do you require reconciliation reports that compare system-calculated charges to historical billed amounts? Options: Yes, No
• What tolerance thresholds should trigger review flags (e.g., variance > 2%)? Options: 1%, 2%, 5%, Custom

Generate ASC 842/IFRS 16 Accounting Reports

• Which accounting standard(s) must reports comply with? Options: ASC 842, IFRS 16, Both, Other/Custom
• What level of detail is required for journal support and disclosures (portfolio summary, lease-level, cash flow projections)? Options: Portfolio summary, Lease-level detail, Both, Custom
• Do you require audit-ready export packages and reconciliations for auditors? Options: Yes - full package, Yes - summary only, No
• How do you expect lease classification decisions and assumptions to be documented in the reports? Options: Automated notes with rationale, Manual documentation uploaded, Both
• Who will validate accounting outputs: internal finance, external audit, or both? Options: Internal finance, External auditors, Both
• Are there required reporting frequencies (monthly/quarterly/yearly) or close schedules to support? Options: Monthly, Quarterly, Annually, Custom

Integrate with ERP and Accounting Systems

• Which ERP/accounting systems must be integrated? Options: Oracle, SAP, NetSuite, Workday, QuickBooks, Other
• What integration method do you prefer or require (file export/import, SFTP, API, middleware)? Options: API, SFTP/flat files, Middleware/EDI, Manual export/import, Other
• What data elements must flow to ERP (journal entries, amort schedules, payable invoices, charge lines)? Options: Journal entries, Amortization schedules, Payable invoices, Charge lines/GL detail, Other
• Who will manage mapping to your chart of accounts and GL structure? Options: Customer finance team, Vendor services, Hybrid
• Do you need real-time sync or scheduled batch transfers for accounting data? Options: Real-time/API, Daily batch, Weekly batch, Monthly batch
• Are there security, VPN, or IP whitelist requirements for integration? Options: Yes, No, Unknown

• Non-Disclosure Agreement (NDA)
• Master Services Agreement (MSA)
• Statement of Work (SOW)
• Order Form / Commercial Terms
• Service Level Agreement (SLA)
• Software Licensing Agreement
• Data Processing Agreement (DPA)
• Security & Compliance Addendum
• Implementation Timeline & Project Plan
• Migration & Data Validation Responsibilities
• Acceptance Criteria & Cutover Signoff
• Change Order Agreement
• Termination, Data Return & Exit Support
• Support & Ongoing Services Addendum
• Governance & Escalation Matrix

• Success Metrics Review — Outcomes vs Agreed Success Signals
• Lessons Learned Workshop
• Shared Backlog & Prioritization — Issues and Enhancements
• Operational Escalation, SLA & Support Review
• Executive Value Review & Expansion Planning

• Identify preventative actions to reduce recurring incidents and assign owners.
• Owner to update deployment runbooks and training materials reflecting agreed improvements.
• Schedule targeted follow-ups (data cleanup, training refresh, workflow tweaks) with assigned owners.
• Current Backlog Snapshot
• Prioritize backlog items by business impact and technical feasibility with a committed next-step for each top item.
• Assign clear owners, acceptance criteria, and target delivery windows to prioritized items.
• Ensure transparency on roadmap implications for customer operations and any interim mitigations.
• Update the shared backlog with prioritized ranking, owners, and acceptance criteria within 2 business days.
• Product/Engineering to produce a high-level delivery timeline for top 3 customer-priority items.
• Customer to confirm business-impact priorities or re-score items where needed.
• Support Performance Summary
• Close or agree actionable next steps for all critical open escalations.
• Confirm or update the SLA, reporting cadence, and escalation RACI to match operational realities.
• Introductions & Meeting Objectives
• Support team to provide a remediation plan with target resolution dates for all P1/P2 tickets within 48 hours.
• Update the escalation RACI document and publish the revised SLA and reporting cadence.
• Implement one preventative/configuration change in the platform pilot and monitor impact for 30 days.
• Executive Summary of Outcomes
• Secure executive alignment on the value delivered and a decision path for renewal or expansion.
• Obtain approval to fund top-priority enhancements or additional licenses where ROI is demonstrated.
• Confirm executive sponsor and cadence for future business reviews.
• Deliver an executive one-page value memo (metrics, ROI assumptions, recommended next steps) within 3 business days.
• Prepare an expansion proposal with cost/benefit analysis for approved enhancement candidates.
• Schedule the next executive business review and confirm sponsor attendance.
• Confirm which success signals are met, partially met, or unmet against objective evidence.
• Agree an ownership-driven remediation plan and timeline for any unmet signals.
• Document acceptance status (accepted, accepted-with-conditions, or not-accepted) to move to formal closeout or remediation tracking.
• Deliver a reconciled metrics packet (CSV + short narrative) for each success signal within 3 business days.
• Owner to create remediation tasks with owners, acceptance criteria, and target completion dates for unmet signals.
• If accepted-with-conditions, schedule a re-check meeting date to validate remediation outcomes.
• Context & Timeline Review
• Create a prioritized list of operational improvements and process changes drawn from real examples.
• Assign owners and timelines for each improvement so changes are actionable and tracked.
• Deliver updated onboarding/runbook artifacts to reduce similar risks in future waves.
• Compile workshop notes into a 'Lessons Learned' document and distribute to stakeholders within 5 business days.
• Recap of Agreed Success Signals
• Open Escalations Deep Dive
• Business Impact Scoring
• What Worked Well
• ROI & Cost Avoidance Analysis
• Adoption & User Health
• Process & RACI Review
• What Didn’t Work / Pain Points
• Technical Effort & Dependencies
• Presentation of Measured Outcomes
• Impact Assessment
• Expansion & Roadmap Opportunities
• Prioritization & Roadmapping
• SLA Adjustments & Reporting Cadence
• Gap Analysis & Root Cause Summary
• Improvement Actions & Owners
• Preventative Actions
• Acceptance Criteria & QA Plan
• Key Decisions & Next Executive Steps
• Customer Validation
• Documenting & Sharing
• Owner Assignment & SLAs
• Decisions & Next Steps