Quick Grounding: Who Are We Talking To?

• What's your title and which team are you representing today? Options: General Counsel, VP / Director Legal Ops, Chief Procurement Officer, Head of Contracts / Contract Manager, IT / Integration Lead, Other
• Which business units will feel the biggest impact from contract changes (pick all that apply)? Options: Sales/Commercial, Procurement, Legal, Finance, IT, HR, Operations, Other
• Roughly how many active agreements are you managing today? Options: < 500, 500–2,500, 2,500–10,000, 10,000–50,000, 50,000+
• What was the immediate trigger that brought this project up the priority list? Options: Missed auto-renewal, Regulatory audit, New CPO / GC arrival, M&A / divestiture, Failed past CLM rollout, Other
• What's one tangible outcome you'd need this quarter to feel like progress?

Who Holds the Keys?

• If someone asked you to name the single person who can green-light this project, who would it be—and why might they not already be pushing for change? Options: General Counsel, Head of Legal Ops, CPO / Head of Procurement, CFO, CEO, Board / Audit Committee, Other
• Please list the key decision-makers (name & role) across Legal, Procurement, and IT who will be involved in approvals or budget sign-off.
• What kind of decision authority does each stakeholder hold? Options: Final approval (budget & legal), Budget approval only, Technical sign-off (IT), Recommend only, Operational owner (pilot/rollout)
• Where do these stakeholders usually resolve disagreements—formal governance committee, exec one-on-ones, or informal hallway conversations? Options: Formal steering committee, Executive leadership meetings, Peer working groups, Ad-hoc conversations, Escalation to finance/CEO
• When past contract initiatives stalled, which role has most often been the bottleneck and why?

When Does Time Become a Threat?

• How many missed deadlines or renewal failures would push this from an operational problem to a board-level crisis? Options: One material miss, 2–3 misses, Several recurring misses, Inevitably critical due to regulatory exposure, Unsure
• What is your target timeline for a pilot and for enterprise rollout? Options: Pilot in 4–8 weeks, Pilot in 8–12 weeks, Pilot in a quarter, Pilot later than a quarter, Enterprise rollout within 2 quarters, Enterprise rollout within 4–6 quarters
• Are there hard external deadlines (audits, contract expirations, regulatory reports) that create immovable launch dates? Options: Yes — audit/regulatory, Yes — material renewals, Yes — board / investor deadline, No hard deadlines, Unsure
• Which internal calendar events most influence your timing (budget cycle, fiscal close, product launches)? Options: Budget cycle, Year-end close, Product launch, M&A calendar, Compliance reporting, Other
• What would be the consequences if the pilot slips by one quarter?

What Does 'Success' Actually Mean Here?

• If someone asked you in six months whether this project succeeded, what headline would make you proud?
• Which metrics will you use to prove success (select up to three primary measures)? Options: Contract cycle time reduction, Extraction/accuracy rate, Renewal avoidance dollars saved, Repository coverage (%), User adoption (% active users), Time to signature, Reduction in legal review hours
• For the metric you care most about, what is a realistic target you’d accept at pilot completion? Options: 10% improvement, 25% improvement, 40% improvement, 60%+ improvement, We haven't set a target
• Who will own measurement and reporting for these success metrics? Options: Legal Ops, Procurement, IT / Integrations, Finance / FP&A, Product Ops, Other
• Which system will be the single source of truth for reporting these metrics (CLM, CRM, ERP, BI tool)? Options: CLM, CRM (Salesforce, HubSpot), ERP (SAP, Oracle), Business Intelligence (Tableau, PowerBI), Other

Who's Going to Carry Adoption On Their Back?

• Who will be publicly accountable if end-users ignore the new system? Options: Head of Legal Ops, CPO / Procurement Head, IT Director, Business Unit Leader, No single owner / shared accountability
• Who are the likely internal champions who will promote day-to-day use (name & team)?
• Which groups will require formal enablement and training? Options: Legal reviewers, Procurement buyers, Sales reps, Finance, IT admins, Executives
• What has made past rollouts succeed or fail here (e.g., incomplete data migration, poor UX, no incentives)?
• What incentives, KPIs, or governance nudges would align teams to consistently use the CLM? Options: Incentivized KPIs (time to sign), Approval gating (no execution without CLM), Manager scorecards, Training + certification, None / unsure

Where Do Your Contracts Hide—and Why Can't You Find Thirty Percent?

• What structural habit or process most explains why contracts get lost or overlooked in your organization?
• Which repositories currently store executed agreements (select all that apply)? Options: Shared network drives, Box/Dropbox/Google Drive, Email inboxes, CRM (deal records), ERP / Procurement modules, Hard copy / filing cabinets, Third-party vendor portals, Other
• Do you have a single canonical identifier for contracts today (contract ID, PO number, deal ID)? Options: Yes — consistently used, Partially — varies by team, No — multiple identifiers, Unsure
• Which percentage of your active contracts do you estimate are not searchable or lack an execution record? Options: < 5%, 5–15%, 15–30%, 30–50%, >50%
• Which types of contracts are most frequently missing or problematic (vendor, customer, NDA, SOW, labor)? Options: Vendor / supplier, Customer, NDA, SOW / Statement of Work, Master services agreement, Employment / contractor, Other

If Everything Went Right—How Would Work Feel Different?

• Picture a year from now where missed renewals and hidden obligations are history—what daily workflow difference would your team notice first?
• Which integrations are absolutely required for this vision to be realized? Options: CRM (e.g., Salesforce), ERP (e.g., SAP, Oracle), E-signature (DocuSign, Adobe), Identity (SSO), Ticketing / Workflow (ServiceNow), Other
• Which extraction or clause-capture priorities must be right in the pilot (e.g., auto-renewals, pricing, termination windows)? Options: Auto-renewal clauses, Pricing/fee schedules, Termination/cancellation, Notice periods and obligations, Liability/indemnity, Other
• What tradeoffs would you accept to hit your timeline—more manual review upfront, narrower pilot scope, or phased integration? Options: Manual review during pilot, Narrow pilot scope (one contract type), Delayed integration cutover, Full automation only, Unsure
• What would a minimally viable pilot look like (teams, contract types, success criteria)?

Quick Snapshot: Where We Stand Today

• Roughly how many active agreements does your organization manage today? Options: < 500, 500–2,499, 2,500–9,999, 10,000–49,999, 50,000+
• Where are the contracts currently stored (pick all that apply)? Options: Network shared drives, Email inboxes, Local desktops, CLM/contract system, ERP/CRM attachments, Paper/filing, Third‑party repositories (e.g., vendor portal), Other
• Who is primarily responsible for owning the contract repository day‑to‑day? Options: Legal Ops / Contract Manager, General Counsel / Legal, Procurement / Sourcing, IT, Business unit owner, No single owner, Other
• Do you have a canonical list or index of all active contracts today (e.g., a master spreadsheet or system)? If yes, where is it and how reliable is it?
• How would you describe the version/formats of your agreements today (select all that reflect your portfolio)? Options: Mostly native digital (Word/PDF), Scanned images/OCR only, Mixture of native and scanned, Heavily templated with consistent clauses, Highly bespoke with many unique clauses, Other

Are We Losing Contracts Without Knowing It?

• What percentage of executed agreements do you estimate are currently unfindable or missing when you need them? Options: <5%, 5–15%, 16–30%, 31–50%, >50%
• Tell us about a recent incident where a missing or buried contract caused measurable harm (auto‑renewal, failed audit, missed obligation, financial penalty). What happened and who noticed it?
• How are missing contracts typically discovered in your organization? Options: During renewals, Internal audit, Vendor dispute, Sales/CRM reconciliation, Random search, Regulatory request, Other
• How does it feel internally when the team can’t locate an agreement that matters—panic, compliance risk, finger‑pointing, quietly tolerated? Options: Panic/escalation, Operational stress but resolvable, Blame between teams, Accepted as normal, Other
• Who is held accountable when a critical contract is missing or a renewal is missed? Options: Legal, Procurement, Business unit owner, IT, No one / blurred accountability, Depends on contract

What’s Causing Renewals and Deadlines to Fail?

• When a renewal is missed, what root causes tend to surface most often—poor metadata, no owner, human error, system gaps, or something else? Options: Missing metadata/expiry, No assigned owner, Late change in deal, Manual calendar tracking failed, System integrations broken, Other
• Walk me through your current renewal cadence: how do you detect upcoming expirations and who signs off on renewal decisions?
• How often do auto‑renewals lock you into unfavorable commercial terms, and how material are those costs? Options: Never, Rarely (inconsequential), Occasionally (low millions), Regularly (material impact), Unknown
• How much lead time do your teams typically need to decide whether to renew, renegotiate, or exit a contract? Options: >90 days, 60–90 days, 30–59 days, <30 days, Ad hoc / last minute
• Have you quantified missed renewals or renewal avoidance opportunities in the last 12–24 months? If so, please summarize the impact.

How Do Contracts Actually Move Through Your Team?

• If I watched a contract from request to signature, what would surprise me about how many people touch it and how long each step takes?
• Which tools are part of your current approval and negotiation workflow (select all that apply)? Options: Email threads, Redline in Word, SharePoint / network drive, CLM system, E‑signature provider, CRM (e.g., Salesforce), Ticketing system (Jira/ServiceNow), Other
• What is the average contract cycle time for the core contract types you care about (sales, supplier, SOWs, NDAs)? Options: <1 week, 1–3 weeks, 3–8 weeks, 2–4 months, >4 months, Varies widely
• Where do approvals most often stall—legal review, commercial negotiation, procurement approval, signatory availability, or integration with sales ops? Options: Legal review, Commercial negotiation, Procurement approvals, Signatory availability, SalesOps/CRM sync, Other
• How consistent are templates and clause usage across teams and regions? Options: Highly consistent, Mostly consistent with exceptions, Highly inconsistent, No templates used, Unknown

Where Does Contract Data Fall Apart?

• Which of your systems currently need reliable contract data to operate effectively (pick all that apply)? Options: CRM (e.g., deal records), ERP/finance, Procure‑to‑pay, GRC/compliance, HR, Custom internal apps, Other
• Which fields or terms do you most need extracted and machine‑readable (e.g., effective date, renewal terms, notice periods, pricing, obligations)? Options: Effective/termination dates, Renewal/notice windows, Pricing/fees, Service levels/penalties, Termination rights, Obligations/milestones, Confidentiality/PII clauses, Other
• Do you currently have any automated integrations moving contract data into CRM/ERP? If yes, which ones and how reliable are they?
• Where does manual re‑entry happen most often and why (e.g., poor mapping, missing metadata, timing mismatches)?
• How quickly does contract data need to appear in downstream systems (real‑time, daily, weekly) for teams to operate without workarounds? Options: Real‑time, Within 1 hour, Daily, Weekly, Ad hoc / acceptable delay

Migration and Extraction Reality Check

• If we attempted to extract key terms from a random sample of your agreements today, how confident would you be in the accuracy (think: first‑pass extraction)? Options: >95% confident, 80–95% confident, 60–79% confident, <60% confident, No idea / never measured
• How many representative agreements could you reasonably provide for a proof‑of‑concept (POC) and do they include high‑complexity clauses (e.g., multi‑tier pricing, supplier SLAs, nested renewals)? Options: <50, 50–199, 200–999, 1,000+, Cannot provide representative set
• Are your historical contracts primarily digital originals or scanned images, and do you have OCR pipelines already in place? Options: Mostly digital originals, Mostly scanned images, Even mix, OCR in place, OCR not available
• Have you attempted a previous migration or extraction project? What went well, what failed, and why?
• Which clause types or nonstandard terms do you anticipate will require manual review during migration (e.g., bespoke indemnities, multi‑party agreements, local law addenda)?

Who Decides and Who Actually Uses the System?

• If a CLM were introduced and not adopted, who would you expect to stall or bypass it—and why? Options: Legal reviewers, Sales reps, Procurement, Business units, IT, Finance, Other
• Who would be the executive sponsor(s) for a contract repository project and who are the day‑to‑day champions?
• What past technology rollouts did your teams embrace or resist? What made the difference?
• How do you measure user adoption and what thresholds would make you feel comfortable to expand beyond a pilot? Options: Login frequency, Transactions processed, Search success rate, Reduction in email attachments, Manual workaround decline, Other
• What training, governance, or rewards have worked historically to change document handling behavior?

What Would ‘Safe’ Migration and Short Wins Look Like?

• If we had to pick three minimal success criteria to prove this platform works for you, which would you prioritize (e.g., extraction accuracy, renewal avoidance, CRM sync integrity)? Options: Extraction accuracy (specific fields), Renewal alerting & avoidance, CRM/ERP integration integrity, Workflow cycle time reduction, User adoption in pilot BU, Data quality and deduplication, Other
• What data quality thresholds would feel acceptable to move from pilot to rollout (e.g., 90% of dates correct, 95% of pricing cases flagged)?
• What would be an acceptable pilot scope and length to build confidence (number of users, business unit, or contract subset and duration)? Options: Single business unit, 1 quarter, Cross‑functional pilot, 1 quarter, Single BU, 2 quarters, Multi‑BU staged pilot, 2–3 quarters, Other
• What internal approvals and stakeholders must sign off before a migration or POC can begin?
• What is the smallest meaningful outcome we could deliver in 4–8 weeks that would reduce your risk or workload?

Immediate Next Steps We Can Take Together

• Which of the following documents can you share within two weeks to accelerate discovery and a POC? Options: Representative agreements (sample set), Current repository index or inventory, Renewal calendar/export, Example workflows or SLAs, Integration specs/API docs, None available
• Who are the three people we should meet next (name, role, and what they own related to contracts)?
• What timeline would you be comfortable committing to for a short POC (start window and duration)? Options: Start within 2 weeks, Start in 1 month, Start in 1–2 months, Unsure / need internal alignment
• What would make you hesitate to proceed with a POC or migration in the next 60 days? Options: Budget constraints, Resources unavailable, Legal concerns, Security/compliance review, No hesitation, Other
• Finally, what single question should we answer in our next meeting to make progress for you?

Quick Orientation — Who We’re Talking To

• Which of these best describes your primary role in this project? Options: General Counsel / Legal Head, VP / Director Legal Ops, Chief Procurement Officer, Contract Manager, IT / Integration Lead, Other
• How many active agreements do you expect to migrate in the initial phase? Options: Fewer than 1,000, 1,000–5,000, 5,001–25,000, 25,001–100,000, 100,000+
• Who is the executive sponsor for this CLM initiative?
• What outcome would make this migration an obvious success to your leadership? Options: Reduce cycle time, Prevent auto-renewals, Centralize repository, Improve compliance visibility, Accelerate procurement, Other

If We Move Forward Tomorrow, What Breaks First?

• If we attempted a migration this month with your current state, what single operational failure would you most fear? Options: Missed renewals, Lost agreements, Data corruption, Integration outages, User pushback, Other
• How often have missed renewals or lost contracts caused financial or compliance impact in the last 24 months? Options: Never, Once, 2–3 times, 4–6 times, More than 6
• Tell us about the most recent incident: what happened, who discovered it, and what was the fallout?
• Which of these would be the biggest reputational or regulatory risk if it occurred during migration? Options: Exposing PII/PII leakage, Losing executed signatures, Failing audit trails, Breaking contractual obligations, Incorrect renewals processed

Where Your Contracts Actually Live — and Why That Matters

• Is there a single source of truth for executed agreements today—or are they spread across places everyone assumes someone else owns? Options: Single central repository, Multiple known repositories, Scattered across drives and emails, Unknown / no single owner
• List the top three locations where executed contracts are stored today (e.g., SharePoint site name, network drive, cloud storage, CRM attachments).
• Which file types and formats make up the bulk of your portfolio? Options: PDF (scanned), PDF (native text), Word docs, Signed images, Emails/attachments, Other
• Approximately what percentage of agreements are missing metadata (party names, effective date, contract type)? Options: 0–10%, 11–25%, 26–50%, 51–75%, 76–100%
• Are there known pockets of 'lost' agreements (teams, geographies, or BU) we should prioritize?

Who Pulls the Levers? Ownership, Templates & Decision Rights

• Who currently owns clause libraries and contract templates—and is that ownership consistent across the business? Options: Legal / GCs team, Procurement, Business Unit owners, No clear owner, Shared ownership
• Describe the approval chain for new or updated templates—who must sign off and how long does sign-off typically take?
• Which roles will be responsible for acceptance testing of migrated templates and clause libraries? Options: Legal reviewers, Procurement leads, IT / Security, Business stakeholders, External counsel
• How many approved templates do you expect to bring into the system at launch? Options: Fewer than 10, 10–50, 51–200, 201–1,000, 1,000+
• Are there high-risk templates or clauses (e.g., renewals, indemnities, data residency) that require special validation? If so, list them.

Wiring the Systems — Integrations, Endpoints, and Data Flows

• If your CRM or ERP went read-only during cutover, what revenue or operational processes would immediately suffer? Options: Sales contract generation, Billing / invoicing, Renewal workflows, Procurement orders, Reporting & analytics
• Which systems must be actively integrated for the migration to be considered minimally viable? Options: Salesforce / CRM, SAP / ERP, Workday, Procure-to-Pay, Document storage (SharePoint/Box), Other
• Provide the status for each required integration: available API, existing connector, or custom build required. Options: API available, Existing connector, Requires custom integration, Not scoped yet
• What are your non-negotiable SLA windows for integration cutovers (maintenance windows, nightly batch windows, blackout dates)?
• Who will be our technical point of contact for each system integration (name, role, email)?

Data Cleanliness & Extraction Confidence — Is It Ready to Meet Our Accuracy Claims?

• If extraction accuracy dips below 90% on day one, which business processes will be most impacted and how will you detect it? Options: Renewal alerts, Obligation tracking, Reporting/analytics, Contract drafting pre-fill, Other
• Describe any known OCR/scanning issues in your portfolio (e.g., scanned PDFs, multilingual documents, handwritten signatures).
• What percentage of your repository is scanned (image-only) versus native text documents? Options: 0–10%, 11–25%, 26–50%, 51–75%, 76–100%
• Do you already have standardized metadata definitions (e.g., party, effective date, renewal clause ID)? If yes, are they documented? Options: Yes—documented, Yes—but informal, No
• Would you be willing to allocate SMEs to a rapid QA cycle to validate extractions during pilot? If so, how many FTEs and estimated hours/week?

People, Change, and Adoption — Who Will Use It and Why They Might Resist

• Why do you think people avoided the last CLM attempt—and what would need to be different this time for them to adopt it?
• Which user groups must be active participants in pilot acceptance (legal reviewers, procurement ops, sales reps, contract admins)? Options: Legal reviewers, Procurement ops, Sales reps, Contract admins, Finance, Other
• Who are the natural champions or skeptics we should engage early, and what influence do they hold?
• Which enablement formats work best for your teams: live workshops, recorded modules, office hours, or embedded in-app guidance? Options: Live workshops, Recorded modules, Office hours / Q&A, In-app guidance, Train-the-trainer
• How will adoption be measured after launch (e.g., % of agreements created in CLM, time-to-execute, user logins)? Choose up to three. Options: % agreements in CLM, Cycle time reduction, User activation / logins, Error/exception rates, Renewal avoidance, Other

Cutover, Validation & Rollback — The Safety Nets You Need

• If the migration causes workflow disruption, what's the immediate rollback or mitigation plan? Options: Pause migration and remediate, Re-open legacy systems, Run parallel systems, Manual patches, Not defined yet
• What window(s) do you prefer for cutover work to minimize business impact (weekend, nightly batches, month-end avoidance)? Options: Weekend maintenance window, Nightly batches, Business hours with limited users, Month-end blackout avoidance
• Which test cases must pass before we approve final cutover (examples: extraction accuracy, renewal alerts, signature integrity, CRM sync)?
• How will we document and approve migration exceptions (e.g., documents requiring manual re-key or legal review)? Options: Tracked in ticketing system, Spreadsheet + owner, Migration tool exceptions log, Not defined
• Who has authority to halt cutover if critical issues appear, and what is their expected SLA for decisions?

Measures, Milestones & Signoff — How We’ll Know We’ve Succeeded

• If leadership asked you for three measurable outcomes to sign off the pilot, what would they be?
• What target thresholds should we use for initial acceptance (e.g., extraction accuracy %, user adoption %, reduction in cycle time)? Options: Extraction ≥ 90%, User adoption ≥ 60%, Cycle time reduction ≥ 25%, Renewal alert accuracy ≥ 95%
• What governance cadence would you prefer post-launch to review issues and improvements (weekly, biweekly, monthly, quarterly)? Options: Weekly, Biweekly, Monthly, Quarterly
• Who will sign the final acceptance: name, title, and what criteria do they require to sign?
• What are the top three unknowns that, if resolved early, would make the rollout low risk?

Quick Snapshot — a five-minute truth check

• Roughly how many active agreements does your team manage today? Options: Less than 500, 500–2,500, 2,500–10,000, 10,000–50,000, 50,000+
• Which phrase best describes how confident you feel about locating an executed contract when someone urgently asks for it? Options: Always confident, Usually confident, Sometimes confident, Rarely confident, Never confident
• Tell me about the last time a contract couldn’t be found — what happened, who was affected, and what was the real cost?
• Which of these best describes why you're exploring contract tooling today? Options: Missed auto-renewal(s), Audit found missing contracts, New leadership mandate, Contract cycle time is too slow, Integration/data disconnects, Other
• Which teams will feel the biggest change if we improve contract visibility and automation? Options: Legal, Procurement, Sales, Finance, IT, Operations, Compliance, Other

Where Your Contracts Really Live (and Why That Matters)

• If I asked you to pull every executed contract with a named vendor right now, how long would it take — and why isn't it faster?
• Where are your contracts currently stored? (select all that apply) Options: Shared network drives (e.g., file server), Cloud storage (Box/Dropbox/Google Drive), Email inboxes/attachments, CRM/Deal attachments, ERP/Procurement attachments, Existing CLM or contract system, Paper/filing cabinets, Local devices/laptops, Other
• How consistent are file names, metadata fields, and tagging across those repositories? Options: Highly consistent & standardized, Mostly consistent, Inconsistent, Nonexistent or random
• How often do duplicates or multiple conflicting versions create operational confusion? Options: Very frequently, Often, Occasionally, Rarely, Never
• Walk me through the usual steps someone takes to find an executed contract today — who initiates it and what tools do they use?
• How confident are you that signatures and execution records across your repositories are legally defensible? Options: Very confident, Somewhat confident, Not confident, Unsure
• Estimate: what percent of agreements are missing one or more critical metadata fields (expiration, renewal terms, counterparty ID)? Options: 0–10%, 10–25%, 25–50%, 50–75%, 75–100%, Unsure

Are Renewals Silently Deciding Your Future?

• How many contracts in the last 12 months do you suspect renewed without explicit, recent human agreement to the new term? Options: None that I'm aware of, 1–5, 6–20, 21–100, 100+
• Has your organization experienced measurable financial impact from missed renewal notifications? Options: Yes — > $1M, Yes — $100k–$1M, Yes — <$100k, No known financial impact, Unsure
• Describe the current renewal monitoring process: who watches deadlines, how are alerts issued, and what typically fails?
• Where do renewal and expiration dates currently live? (select all that apply) Options: Spreadsheets, Calendars (Outlook/G Suite), CRM/Deal records, CLM/contract system, Email threads, No centralized tracking, Other
• What are the most common failure modes that lead to missed renewals in your environment (process, ownership, technical gaps)?
• How acceptable is the current renewal risk level to your executive sponsors? Options: Unacceptable — urgent fix required, Concerning but tolerated short-term, Acceptable for now, Leadership unaware/unsure

Who's Actually In Charge (and Who's Left Picking Up the Pieces)

• If we had a contracting emergency that required approvals within 48 hours, who would we call — and would they be able to act?
• Which roles will be the primary decision-makers for selecting and approving a CLM platform? Options: General Counsel, Legal Operations Director, Chief Procurement Officer, CFO, Head of IT, CEO, Head of Sales, Other
• Who are the day-to-day operational owners responsible for template governance, metadata standards, and user onboarding?
• How clearly documented are approval roles and escalation paths today? Options: Well documented and enforced, Partially documented, Informal/tribal knowledge, Nonexistent
• Have people bypassed your formal contract process? If so, tell me one situation and why it happened.
• How involved will IT need to be for security, SSO, and API approvals on a CLM project? Options: Fully responsible and hands-on, Consulted/approving only, Shared responsibility with Legal Ops, Minimal involvement, Unsure

When Your Systems Don’t Talk — What Breaks First?

• If your CRM or ERP suddenly couldn't access contract terms, what business processes would immediately slow or stop?
• Which systems must integrate with a CLM for this project to be considered successful? (select all that apply) Options: CRM (e.g., Salesforce, HubSpot), ERP (e.g., SAP, Oracle), Procurement/PO system, eSignature provider (DocuSign/Adobe), Identity/SSO provider, BI/Analytics or Data Warehouse, Custom applications, Other
• Describe a past integration attempt that failed or created pain — what went wrong and who fixed it?
• How much contract metadata needs to flow into CRM/ERP to make day-to-day decisions (renewal dates, pricing, obligations, approvals)? Options: All key terms and dates, High-value clauses and dates, Only renewal/expiry dates, Minimal or none, Unsure
• Who in your organization currently owns API keys, integration endpoints, and production change approvals?
• What SLAs or uptime requirements must integration points meet for your business-critical processes? Options: 24/7 critical with fast recovery, Business hours with fast recovery, Standard enterprise SLA (e.g., 99.9%), No formal SLA required

Workflows That People Actually Use (vs. Workflows on Paper)

• Roughly what percent of your contracting steps happen outside formal workflows (email threads, spreadsheets, or ad-hoc drafting)? Options: 0–10%, 11–30%, 31–60%, 61–90%, 90–100%
• Which phases of contracting cause the biggest time sinks today? (select all that apply) Options: Request intake/triage, Clause/template selection, Drafting/authoring, Redlining/negotiation, Approval routing, Execution/signature, Post-signature obligations capture, Renewal management, Other
• Share a specific example where the workflow added friction rather than removing it — what would you change first?
• How often do users bypass the system because email or direct messaging is faster? Options: Very often, Often, Sometimes, Rarely, Never
• What training, incentives, or governance actions have you tried to improve platform adoption and which had the biggest effect?
• What level of additional process overhead is acceptable if it significantly reduces legal or financial risk? Options: Low — must not slow teams down, Medium — some overhead ok, High — prefer process for control, Depends on the team/process

Data & Extraction — How Close Are You to Truth?

• If an AI extraction returned 95% accuracy today, would your teams trust that output to drive renewals and compliance without human review? Options: Yes, fully trust, Trust with spot checks, No, need higher accuracy, Depends on clause type
• Have you run any prior extraction or AI pilots on your contracts? Options: Yes — successful, Yes — partial success, Yes — failed, No, Planned but not started
• Which fields are highest priority to extract for business value (select all that apply)? Options: Renewal/expiry dates, Notice periods/cure periods, Pricing/payment terms, Auto-renewal clauses, Termination rights, Key obligations/SLA terms, Counterparty identifiers, Other
• What minimum accuracy threshold would stakeholders require before trusting automated extraction for decision-making? Options: ≥98%, 95–97%, 90–94%, <90%, Unsure
• How do you currently validate extracted data and who is responsible for final sign-off?
• How many representative agreements can you reasonably provide for a proof-of-concept or pilot? Options: Less than 50, 50–200, 200–1,000, 1,000+, Unsure

What Success Actually Looks Like (and Who Will Celebrate It)

• If we proved a 40% reduction in contract cycle time, what would that change about your team's credibility, budgets, or executive priorities?
• Which success signals matter most to your executive sponsors? (select all that apply) Options: Cycle time reduction, Fewer missed renewals, Improved audit/compliance outcomes, Cost savings, User adoption and reduction in bypass, Improved deal velocity, Reliable contract data in CRM/ERP, Other
• What specific acceptance criteria must be met for a pilot to be considered successful?
• How quickly would you expect a pilot to show measurable results that matter to leadership? Options: Within 1 month, 1–3 months, 3–6 months, 6+ months, Unsure
• Which stakeholders must sign off to move from pilot to enterprise rollout and what are their biggest blockers?
• After rollout, how would you like governance and ongoing support to be structured? Options: Dedicated customer success + governance cadence, Periodic health checks only, Self-managed with support portal, Hybrid model with managed services

Deciding to Move — What Would Make This Easy to Say Yes To?

• What single unresolved fear would stop you from committing to a CLM project today?
• Which commercial or licensing models would make procurement simpler for you? Options: Subscription/SaaS (annual), Per-seat, Per-contract/volume-based, Consumption-based, Hybrid, Unsure
• What pilot scope would you view as low-risk but still meaningful enough to prove value?
• What budget cycle or procurement windows should we align with to make contracting straightforward? Options: Immediate/this quarter, Next quarter, Fiscal year planning, Dependent on another project, Unsure
• What would make your legal ops and procurement teams genuinely excited to adopt this system every day?
• Select the top three obstacles that could block starting now. Options: Budget, Executive alignment, IT resources/priority, Data readiness/migration, User resistance, Integration complexity, Procurement/legal terms, Other

Commitment & Next Steps — Concrete First Actions

• If we did nothing after this conversation, what would still be broken in 12 months that you wish would change?
• Which of the following actions would you be willing to commit to in the next 30 days? (select all that apply) Options: Share representative executed agreements, Introduce our team to IT/security, Define pilot success criteria, Allocate budget or issue PO, Schedule POC kickoff meeting, Assign a project owner
• Who will be our single point of contact for the pilot and what decision authority will they hold?
• What is your preferred timeframe to kick off a proof-of-concept or pilot? Options: Immediately/This week, Within 2 weeks, Within 1 month, 1–2 months, Later
• Before we start, what are the top concerns you want us to address in the kickoff materials or demo?