A Quick Welcome: Who's in the Room?

• What's your name, title, and the team you represent for this engagement?
• Which function will be our primary contact for contract decisions during evaluation and pilot? Options: General Counsel / Legal Ops, VP / Head of Procurement, Chief Procurement Officer (CPO), Head of Sales Operations, IT / Security, Other
• Who else should we include or be aware of (titles or roles) when we talk about decisions, timelines, and legal buy-in?
• How would you prefer we run discovery sessions with your team—single workshop, weekly checkpoints, or role-specific breakouts? Options: Single workshop (2–3 hours), Multiple short sessions (3–5 x 45–60 mins), Weekly checkpoints, Role-specific breakouts, Flexible / we'll decide after kickoff
• What outcome from this discovery would make you say the session was time well spent?

Who Really Decides — and When They Step In

• If a high-value contract stalled in review today, who in your organization would escalate it—and why would they escalate?
• Which of these roles typically signs off at each stage: commercial terms, legal redlines, and final approval? Options: Sales/Rev Ops (commercial), Legal (redlines), Procurement (vendor terms), Finance (commercial/PO), Business unit leader (budget/strategy), Other
• How often do decision roles change between rounds of negotiation (e.g., new stakeholders joining mid-cycle)? Options: Rarely, Occasionally, Often, Almost every deal
• Which stakeholders will be required to validate extraction accuracy or sample migrations during the pilot? Options: Legal reviewers, Procurement analysts, IT / Data Governance, Business owners, No one assigned yet, Other
• Tell us about one recent deal where stakeholder handoffs broke down—who missed what deadline and what happened as a result?
• What is your internal timeline expectation for engaging legal and procurement in pilot decisions (e.g., immediate, after initial demo, after sample load)? Options: Immediate (same week), After initial demo, After sample contract load, During pilot validation, Unclear / TBD

Where Contracts Break and Money Leaks

• When you look back at the last 12 months, which single contract failure cost you the most (time or money), and what was the exact failure mode?
• How often do these failure modes occur in your business? Options: Multiple times per month, Monthly, Quarterly, A few times a year, Rarely
• Which of these outcomes have you observed as a consequence of contract failures? Options: Missed termination/auto-renewal, Lost negotiated pricing, Revenue leakage, Regulatory non-compliance, Contract disputes/escalations, Other
• How do missed renewal or termination windows typically get discovered in your org? Options: Manual calendar reminders, Email escalation, Quarterly audits, Owner happens to notice, We don't have a reliable method
• Share a concrete example where an automated alert would have changed the outcome—what would that alert need to have said and when?

The Black Box: How You Store, Find, and Lose Contracts

• If someone asked right now where your executed contracts live, how would you answer? Options: Single shared repository (e.g., CLM), Multiple systems (network drives, SharePoint, emails), Local drives & email threads, Combination but unmanaged, We don't know
• Which systems or locations currently contain significant contract volume we should consider for sample migration? Options: Shared drives (network), SharePoint/OneDrive, Salesforce attachments, Email folders, Third-party repos (Box/Dropbox), Other
• How are executed agreements currently indexed or tagged for retrieval (if at all)? Options: No consistent indexing, Manual spreadsheet tracking, Metadata in repo, CRM links, Other
• What percentage of your contracts would you estimate are missing clear owners or renewal dates today? Options: 0–10%, 10–25%, 25–50%, 50–75%, 75–100%
• Describe a recent search for an executed agreement that failed—what did you try, and how long did it take?
• Which file types or formats are most common in your portfolio (helpful for extraction planning)? Options: Scanned PDFs (images), Native Word docs, Mixed PDFs with Word origin, Signed PDFs with attachments, Other

What 'Good' Actually Looks Like for Legal and Procurement

• If legal could wave a wand and change one contract-related metric immediately, what would it be (and why does that metric matter)?
• Procurement: if you could guarantee one operational outcome after pilot, which would move the needle for your leadership? Options: Enforce negotiated pricing, Prevent auto-renewals, Faster PO-to-execution, Standardized supplier terms, Other
• Which of these measurable success signals matter most to you for pilot evaluation? Options: Cycle time reduction (days), Extraction accuracy (%), Missed renewal avoided ($), Number of contracts migrated, User adoption rate
• What are acceptable targets for those signals (be specific — e.g., reduce avg redline cycle from 28 to __ days)?
• Who in your organization will sign off that the pilot met those targets (name/role)?
• Which legal or procurement controls must remain in place—non-negotiable items we must model in the demo or pilot? Options: Clause approval workflow, Two-step sign-off for certain terms, Audit trail & versioning, Retention policies, Data residency constraints, Other

The Change Barriers No One Admits

• If someone said 'we could cut redline cycles in half' — what's the most common internal argument you'd hear against it?
• Which of these has been the biggest real-world barrier to adopting a new CLM or workflow tool in your org? Options: Migration effort, Lawyers prefer Word email redlines, Integrations/IT risk, User adoption & training, Budget/Procurement cycle, Other
• How curious or skeptical are your legal reviewers about AI-based clause extraction on real contracts? Options: Very curious/open, Cautiously optimistic, Skeptical but willing to test, Strongly skeptical/not allowed
• What concerns would your security or data-governance teams raise about uploading sample contracts for evaluation? Options: PII exposure, Data residency, Third-party access, No concerns, Other
• If migration effort is the blocker, what size of pilot (number of contracts, formats) would make stakeholders comfortable to validate value without a full migration? Options: 10–25 contracts, 25–100, 100–500, 500+
• Who internally would need to champion this project to overcome organizational inertia?

Proof That Will Convince Your Team

• What evidence would make your GC or CPO say 'this is safe and effective' after the pilot? Options: Extraction accuracy benchmarked, Successful signed workflow, Demo with our contracts, Low effort migration plan, Cost avoidance calculation
• Which sample contracts should we load first to prove the most critical capabilities (pick up to three)? Options: High-value vendor agreements, Master Services Agreements (MSAs), NDAs, Purchase/Procurement contracts, Subscription SaaS agreements, Other
• Do you have recent PDF scans or OCR-blocked files we should know about? If so, how many? Options: None, A few (1–10), Some (11–100), Many (100+)
• How would you like us to demonstrate obligation/renewal alerts against your missed-deadline examples? Options: Side-by-side historical case study, Live demo on sample contracts, Automated report vs. manual tracker, All of the above
• Who will validate extraction accuracy alongside our team (names/roles) and what acceptance threshold should we hit?
• Are there any confidential or MSA clauses we should exclude from the sample set for legal or privacy reasons? Options: No exclusions, Exclude financial terms, Exclude customer-identifying data, Exclude specific MSAs (we will list)

Deciding Together: Timelines, Approvals, and Risks

• What's your ideal decision timeline for moving from pilot to production (select one)? Options: Immediately after pilot, Within 1–3 months, 3–6 months, 6+ months, Undecided
• Which internal approvals are gating steps for procurement and legal to sign a pilot SOW or contract? Options: Budget owner approval, Legal sign-off, Procurement sourcing committee, Security review, Executive sponsor
• What are the non-starters for your team in a commercial pilot (e.g., indemnity, data exposure, trial length)?
• If we present a pilot that reduces redline time but requires two weeks of migration prep, how likely are you to prioritize it this quarter? Options: Very likely, Somewhat likely, Unlikely, Not this quarter
• Which measurable risk would cause you to pause a pilot mid-flight (select up to two)? Options: Low extraction accuracy, Security concerns, User resistance, Integration failures, Cost overruns, Other
• Who should receive a short decision-ready summary at the end of discovery (names/roles)?

Commitment & Next Steps: What We Need to Move Forward

• If we agree to a small proof of value, what resources can you commit from your side (roles and estimated hours)?
• Which of these should we prioritize in the pilot scope to prove immediate ROI? Options: Authoring & clause library, Redline collaboration, Repository migration & extraction, Obligations & renewal alerts, Signature flow and versioning
• What is the minimum pilot length you believe would be credible for evaluation? Options: 2 weeks, 4 weeks, 8 weeks, 12 weeks
• Are there compliance windows or blackout periods we should avoid for migration or pilot work? Options: Quarter-end close, Annual audits, Contract renewals season, No major blackout, Other
• Finally, what's the best way to share sensitive sample contracts with us for extraction testing (upload portal, secure SFTP, in-person transfer)? Options: Secure upload portal, SFTP, Encrypted email transfer, In-person/secure handoff, We'll follow your security process

Who’s Here and What Keeps You Up at Night?

• Which role best describes you in this engagement? Options: General Counsel, VP Legal Operations, Chief Procurement Officer, Head of Procurement, Contracts Manager, Legal Ops Analyst, Commercial Counsel, Other
• How large is the core team that will be working day-to-day with contracts (legal + procurement + ops)? Options: 1–5 people, 6–15 people, 16–50 people, 51–200 people, 200+ people, Not sure
• Which types of contracts will we focus on for this conversation or pilot? Options: Sales/customer contracts, Supplier/vendor contracts, Master service agreements, NDAs, SaaS/subscription agreements, Procurement/purchase agreements, Other
• What specific incident or metric led you to explore a CLM solution right now? (briefly describe the trigger)
• What are the three business outcomes your leadership cares about most from fixing contract workflow problems?
• Who else outside legal and procurement needs to be in the room for decisions about tooling or pilot success? Options: Head of Sales, CFO/Finance, IT/Infrastructure, Compliance/Risk, Business unit leader, Other

If Contracts Could Talk, What Would They Complain About?

• If your contracts could honestly describe how they're handled today, what single sentence would they say that would make you wince?
• Walk me through the authoring path for a typical contract: who requests it, who drafts it, and which tools are used at each handoff?
• Which systems or tools are involved during drafting and negotiation today? Options: Microsoft Word + email, SharePoint, Box/Google Drive, Salesforce, ERP (SAP/Oracle), Dedicated CLM, E-signature only (DocuSign/Adobe), Other
• How frequently do negotiation drafts leave Word/email into another silo (e.g., chat, folder, third-party tool)? Options: Almost always, Often, Sometimes, Rarely, Never
• Tell me about a recent negotiation that stalled or exploded in cost—what specifically in your process contributed to that outcome?
• How do people feel during redlines—do they feel in control, confused about versions, or stretched thin? Give an example.

Where Do Deals Stall and What Does That Cost?

• When deals sit in legal review for longer than expected, what unseen costs show up that rarely make it into a report?
• On average, how many calendar days does a contract spend in legal review or negotiation today? Options: < 3 days, 3–7 days, 8–14 days, 15–28 days, 28+ days, We don’t track
• What are the top three specific bottlenecks that most commonly extend review time? Options: Lack of clause library/templates, Multiple internal reviewers, Undefined approval paths, Slow counterparty response, Manual redline merging, Signature delays, Other
• Which stakeholder group typically causes the longest delays (legal, procurement, sales, finance, other)? Options: Legal, Procurement, Sales/Account Execs, Finance, IT/Compliance, Counterparty
• How are stalled deals escalated internally and what usually triggers that escalation? Options: Automated alerts, Sales escalates to Legal Ops, Weekly review meeting, No formal escalation, Other
• Share one concrete example where a timing delay changed the commercial outcome (lost revenue, reduced margin, cancelled deal). What happened?

When Deadlines Slip, Who Pays the Tab?

• If a missed termination or auto-renewal had to be blamed on one process gap, what would you point to?
• In the last 24 months, how many missed renewals, unnoticed auto-renewals, or missed termination notices produced measurable loss? Options: None, 1–2, 3–5, 6–10, 10+
• Describe how renewal and termination deadlines are currently captured, assigned, and validated.
• Who is accountable for renewal decisions and what system do they rely on for reminders? Options: Legal owner, Procurement owner, Business owner, Finance owner, No single owner, Other
• Have you ever received alerts that were ignored or never reached the right person? If so, why did the alert fail?
• What financial or operational impact would you estimate a single avoided auto-renewal or recovered negotiated savings would deliver?

Where Do Executed Contracts Disappear To?

• If I asked you to fetch an executed contract and the signed version doesn’t sit in an obvious folder, how long would it take and how many people would you need to involve? Options: Under 5 minutes, 1 person, 5–30 minutes, 1–2 people, 30–120 minutes, 2–4 people, Half a day or more, several people, We often can’t find it
• Where are executed contracts currently stored? Options: Central CLM, SharePoint, Shared network drive, Local drives, Email attachments, Box/Google Drive, Contractor portal, Other
• How consistent and reliable is your contract metadata (counterparty name, effective dates, renewal dates, contract values)? Options: Very consistent, Mostly consistent, Patchy, Poor, We don’t capture metadata
• How do people today search for clauses, pricing, or specific obligations when they need to enforce or verify terms?
• How often does procurement fail to enforce negotiated pricing because the executed agreement cannot be located? Options: Never, Rarely, Occasionally, Often, Always
• Have missing executed copies ever caused regulatory, audit, or compliance issues? Describe one instance.

Who’s Responsible — And What Happens When They Don’t Know?

• Is there a single accountable owner for lifecycle outcomes, or has ownership become a hand-off with nobody truly accountable? Options: Single accountable owner, Shared responsibility with clear roles, Ambiguous handoffs, often unclear, No defined ownership
• List the teams/roles that currently perform these activities: request intake, drafting, negotiation, legal approval, procurement approval, signature, post-signature obligations tracking.
• How often are approval paths bypassed and what typically motivates people to skip steps? Options: Never, Rarely, Sometimes, Often, Always
• What SLAs or turnaround expectations exist for each handoff (e.g., legal review within X days)? Options: We have documented SLAs, Informal expectations only, No SLAs today, SLAs exist but are ignored
• When ownership fails, how is the error usually detected (audit, escalation, customer complaint, financial variance)? Options: Automated report, Manual audit, Sales escalates, Executive review, Too late / discovered externally
• Would a clear single owner for post-signature obligations change behavior—why or why not? Options: Yes, significantly, Somewhat, Marginally, No

How Will You Judge Success — Before We Start?

• If we ran a 6-week pilot and you had to decide pass/fail on day 42, what single metric would you hang your hat on?
• Which of the following success signals matter for your leadership? (select all that apply) Options: Average legal cycle time reduction, Clause extraction accuracy (%), Number of avoided auto-renewal losses, Time-to-first-signature, Repository search time, User adoption rate, Other
• What are the current baseline numbers for the metrics you selected (provide best estimates)?
• What target improvement would constitute a clear win for each metric you care about?
• Who must sign off on pilot success (titles), and what artifacts or evidence will they require? Options: GC, VP Legal Ops, CPO, CFO, Head of Sales, IT/Integration Lead, Other
• Would you require a manual validation sample to verify clause extraction accuracy? If yes, how many contracts or clauses would be convincing? Options: No manual validation needed, 10–25 contracts, 26–100 contracts, 100+ contracts, Unsure

If Automation Could Do One Thing Overnight, What Should It Be?

• If you could automate just one repetitive contract task today that would free up the most time, what would it be?
• Which of these automation candidates would deliver the highest immediate value? (choose up to 3) Options: Clause extraction, Template-driven authoring, Automated redline suggestion, Obligation extraction & alerts, Repository classification/migration, Signature workflow automation
• Which specific data points are most valuable to extract automatically (e.g., termination date, renewal terms, pricing, indemnities)? Options: Termination/renewal dates, Pricing/fees, Notice periods, Liability caps/indemnities, Service levels/SLAs, Payment terms, Other
• Are there any clauses or contract types you explicitly do NOT want automated extraction or suggestions for? Explain why.
• How comfortable is the legal team with AI/ML assistance in drafting or clause classification? Options: Very comfortable, Somewhat comfortable, Cautious but curious, Skeptical/averse, Unsure
• What guardrails would you require before adopting automated redlines or clause suggestions (human review, audit log, version control, training)? Options: Human-in-the-loop review, Immutable audit trail, Version comparison tools, Limited scope rollout, Transparency on model confidence, Other

What Will Stop This From Working — Let’s Name the Resistance

• What would make your legal team say 'we’ll stick to Word and email' even after seeing a polished demo?
• How often do lawyers insist on working in native Word redlines today? Options: Always, Often, Sometimes, Rarely, Never
• Which objections do you expect from stakeholders (control over text, auditability, learning curve, risk of AI errors, integrations)? Options: Control concerns, Audit/compliance worries, Steep learning curve, Accuracy/fidelity concerns, Integration complexity, Cost/budget, Other
• What level of migration effort and classification accuracy are you willing to accept for a pilot (e.g., partial dataset, manual validation, phased approach)? Options: Full migration of all contracts, Sample portfolio (100–500), Targeted sets (high-value accounts), No migration—demo only, Unsure
• What training and enablement model has historically worked to win lawyer adoption (hands-on workshops, train-the-trainer, recorded micro-lessons)? Options: Hands-on workshops, Train-the-trainer, Recorded micro-lessons, Office hours/support desk, Blended approach, Other
• Which integrations are mandatory from day one to consider a pilot viable (Salesforce, DocuSign, SharePoint, ERP, SSO)? Options: Salesforce, DocuSign/Adobe Sign, SharePoint, Box/Google Drive, SAP/Oracle ERP, Single Sign-On (SSO), Other

Agreeing on the First Pilot — Concrete Commitments

• If we commit to a pilot, what is the smallest scope that would still prove value for your organization?
• Which pilot components do you want included (select all that apply)? Options: Repository ingestion & classification, Clause extraction & accuracy report, Template-driven authoring, Redline collaboration workflow, Obligations & renewal alerts, Signature flow validation
• How many sample contracts can you provide for the pilot and in which formats? Options: < 50 (PDF/Word), 50–200 (PDF/Word), 200–1,000 (mixed), 1,000+ (mixed), We need help exporting samples
• Who on your team will own ingestion, validation, and pilot training (names/titles)?
• What target timeline do you expect from sample upload to pilot review meeting? Options: 1–2 weeks, 3–4 weeks, 5–6 weeks, 7–12 weeks, Flexible/depends
• What approvals, legal reviews, or security checks must be completed before we can begin ingesting any contracts?

Let's Make the Pilot Tangible

• Who will be our primary day-to-day contact for the pilot? Options: General Counsel, VP Legal Operations, Head of Procurement/CPO, IT Lead, Project Manager, Other
• How many sample contracts can you share immediately and which types are they (high-level)? Options: < 25, 25–100, 100–500, 500–2,000, More than 2,000
• Which systems currently store your executed contracts that we need to touch for the pilot? Options: Network shared drives, SharePoint, Box/Dropbox/Google Drive, Procurement system, CRM (e.g., Salesforce), Local drives / desk folders, Other
• Do you have a firm or flexible target date to begin repository ingestion for the pilot? Options: Within 2 weeks, 2–4 weeks, 1–3 months, 3–6 months, No target yet
• From your perspective, what would make this pilot feel clearly successful at close?

Are We Sure the Right People Will Be in the Room?

• Who in your organization benefits most when contracts are found and obligations executed on time—and why aren't they always at the table today?
• Which stakeholders must explicitly approve access to contract repositories or PII before ingestion? Options: IT Security, Data Privacy/Legal, Procurement, Business Unit Owner, Finance, Other
• Who will validate extraction accuracy and redline workflows during the pilot (titles/teams)? Options: Legal Operations, Line lawyers/counsel, Procurement managers, Contract administrators, IT/Integration lead, Other
• How do these stakeholders prefer to be engaged for decisions—weekly demos, asynchronous reports, or executive checkpoints? Options: Weekly working sessions, Ad-hoc demos, Asynchronous reports/dashboard, Executive steering meetings, Other
• Are there known political or ownership gaps between teams that could slow approvals or access?

What Happens When Contracts Go Missing?

• Think of the last time a missed deadline or lost executed agreement caused damage—whose day did it ruin and what were the tangible consequences?
• How many missed renewals, missed termination notices, or un-enforced pricing events occurred in the last 12 months? Options: None documented, 1–2, 3–5, 6–10, More than 10
• Which contract types have historically caused the largest financial or operational issues? Options: Supplier/vendor contracts, Customer contracts/SOWs, Licenses/Software agreements, Facility/lease agreements, NDAs/Master agreements, Other
• Do you maintain a manual tracker or spreadsheet today? If yes, where and who updates it? Options: Excel/Google Sheets (shared), Procurement system, Internal Legal Ops tool, No tracker / ad-hoc, Other
• How did those contract failures affect your team emotionally and operationally (e.g., trust, morale, overtime, executive escalation)?

What Would Healing the Workflow Actually Unlock?

• If legal review cycles were reliably cut in half, what tangible priorities would you reallocate time and budget toward?
• Which measurable signals should the pilot prove to convince your execs this is worth scaling? Options: Cycle-time reduction (%), Extraction accuracy (%), Missed renewal reduction (count/$), Reduction in attorney review hours, Repository search time decrease, Other
• What minimum extraction accuracy threshold would make the pilot credible to your team? Options: >90%, 85–90%, 80–85%, <80%
• What acceptance criteria—beyond raw accuracy—must be met before we move from pilot to broader migration?
• Are there compliance or regulatory requirements we must maintain or demonstrate during the pilot (e.g., retention, redaction, audit trails)? Options: GDPR/data residency, HIPAA/health data, SOX/financial controls, Industry/regulatory specific, No special requirements, Other

What Exactly Lives in Your Repository?

• If you estimate the legacy pile we’ll touch for this pilot, what hidden surprises should we expect (scanned images, split versions, redactions)?
• Roughly how many documents would you like included in the pilot migration? Options: <100, 100–500, 500–2,000, 2,000–10,000, >10,000
• Which file types and formats will we encounter during ingestion? Options: Native PDFs, Scanned PDFs/images, Word (.docx), Excel, Emails (.msg/.eml), Other
• Do you currently capture metadata (e.g., counterparty, effective date, contract owner)? If so, which fields are most relied upon?
• Who currently maintains contract metadata and who will be responsible for validating migrated metadata during pilot? Options: Legal Ops, Procurement, Individual lawyers, IT/Records, No one / ad-hoc, Other

Rules That Save Time, Not Create More Work

• Which of your current classification or approval rules actually create friction or manual rework today?
• Which automated classification/extraction rules would you want us to prioritize in the pilot? Options: Contract-type detection, Clause-level extraction (e.g., liability, indemnity), Renewal/termination date detection, Monetary terms extraction, Obligation and SLA extraction, Counterparty normalization
• How many custom rules or mappings (e.g., preferred clause variants) would we need to create for a valid pilot test? Options: 0, 1–10, 11–50, 51–200, 200+
• Who will own tuning classification rules during the pilot—your team, ours, or a shared model? Options: Your Legal Ops, Your Data/ML team, Vendor team, Shared responsibility, Other
• How will you want to measure and report false positives and false negatives during the pilot?

Clearances, Approvals, and the People Who Can Stop the Train

• Who has veto power to delay or stop repository ingestion and what specific evidence or safeguards would they require to say yes?
• Which formal technical approvals are required before we can begin (select all that apply)? Options: IT Security review, Data Privacy/Legal review, Procurement/vendor onboarding, Compliance approval, Business unit consent, Other
• Do you require any third-party or vendor security attestations (e.g., SOC 2, ISO 27001) or a DPA before access is granted? Options: Yes — SOC 2 / ISO required, Yes — DPA only, No formal attestations required, Unsure / need to check
• Which authentication and access methods will we need to support for ingestion (e.g., SSO, service account, VPN)? Options: SAML/SSO (Okta/Azure AD), Service account with scoped permissions, VPN with specific IP allowlist, Local accounts, Other
• Are there blackout windows, quarter-end periods, or scheduled maintenance times we must avoid for migration? Options: Quarter close/financial reporting, Major product releases, Company holidays, No known blackout windows, Other

Pilot Success: Small Wins, Big Signals

• What single pilot result would make you the platform's strongest internal advocate?
• Which metrics will you share with executives to tell the pilot story? Options: Time-to-signature, Extraction accuracy, Missed renewals prevented (count/$), Search time reduction, Cost savings, User satisfaction / adoption
• Who holds the final decision to expand from pilot to full rollout? Options: General Counsel, VP Legal Operations, CPO/Head of Procurement, Finance, Cross-functional steering committee, Other
• What artifacts do you need at pilot close to make a go/no-go decision (reports, migration logs, user feedback)? Options: Validated extraction report, Migration summary and logs, User feedback and adoption metrics, ROI/impact estimate, Legal/compliance sign-off, Other
• If the pilot surfaces unexpected issues, what remediation or rollback approach would you consider acceptable?

Quick Ground‑Check: Who’s In This Room (and What Do They Own)?

• Who will be the primary approver of the validation results (title/role)? Options: General Counsel, VP Legal Ops, Head of Procurement, CFO, IT Lead, Other
• Which teams must be available during the validation run (select all that apply)? Options: Legal / Contracts, Procurement, IT / Security, Sourcing, Sales Ops, Finance, Other
• How many sample contracts do you plan to load for validation (ballpark)? Options: <100, 100–500, 500–2,000, 2,000–10,000, >10,000
• Which contract types will be included in the validation set (select up to 3)? Options: Master Services Agreements, SOWs / Statements of Work, NDAs, Purchase Agreements, Sales Contracts, Lease / Real Estate, Other
• What file formats will you upload for validation (e.g., native Word, scanned PDF)? Options: Native Word (.docx), Digital PDF, Scanned PDF/Images, Plain Text/HTML, Other
• When would you like to schedule the validation run (date or range)?

If This Fails, Who Feels The Pain—and How Bad Is It?

• Imagine the validation misses key obligations—what tangible impact worries you most (choose one)? Options: Financial loss (missed termination/auto‑renewal), Regulatory/non‑compliance risk, Contract performance disputes, Operational disruption, Reputational harm, Other
• How many concrete incidents in the last 12 months involved missed deadlines, lost agreements, or failed redlines? Options: None, 1–2, 3–5, 6–10, More than 10
• Tell us about the single worst incident—what happened, what was missed, and how did it surface?
• Who gets pulled in when a missed deadline appears (roles and escalation path)?
• How quickly must a validation failure be resolved before it becomes a business emergency? Options: Within hours, Same day, 48–72 hours, One week, Longer

Can Clause Extraction Actually Stop That $1.2M Leak?

• If our extraction had to prevent your top financial miss, what exact clause or deadline should it always get right?
• What extraction accuracy would make you comfortable moving from manual tracking to automated alerts? Options: >99%, 97–99%, 95–97%, 90–95%, <90%
• Which fields are non‑negotiable to extract correctly in validation (select all that apply)? Options: Effective/Start Date, Termination/Notice Deadlines, Auto‑renewal clauses, Pricing / Discount terms, Renewal Notice Owners, Governing Law / Jurisdiction, Other
• Do you have a ‘gold standard’ (manual spreadsheet or annotated set) we can use to measure extraction accuracy? Options: Yes — annotated set ready, Yes — needs formatting, No — but we can create one, No — we rely on memory/manual tracking
• What languages or localization issues should the extraction model be tested against? Options: English, Spanish, French, German, Portuguese, Multiple/Other

Where Do Redlines Really Break Down (and Who Is Blamed)?

• When a redline cycle stalls today, what’s the usual root cause (pick the most common)? Options: Unclear owner for clause changes, Multiple editors in email/Word, Lost latest version, Legal/Business disagreement, Late stakeholder responses, Other
• How do you expect version history to look in the validated workflow (what audit details matter)? Options: Full per‑edit history with user/time, High‑level version snapshots, Change highlights with comments, Signoff records per party, Other
• Which redline behaviors must be enforced during pilot validation (select all that apply)? Options: Single source of truth editing, Simultaneous editing with merge, Line‑item comment threads, Change accept/reject workflow, Role‑based edit locks, Other
• What tools are your lawyers most comfortable using today during redlines? Options: Microsoft Word Track Changes, Email with attachments, Google Docs, A CLM or contract tool, PDF annotated, Other
• Describe a recent negotiation where versioning caused confusion—what happened and how long did it take to resolve?

Signature Flow: Is It Reliable—or Just Getting Lucky?

• What percentage of your executed contracts today have a complete, auditable signature trail? Options: >99%, 95–99%, 90–95%, 75–90%, <75%
• Which e‑signature providers or methods must the validation support or integrate with? Options: DocuSign, Adobe Sign, OneSpan/EsignLive, In‑house/Custom, No eSign — wet signature workflow, Other
• Have you experienced failed or disputed signatures? If so, what was the root cause?
• What signature behaviors are required in the validated flow (select up to 3)? Options: Sequential signing, Parallel signing, Conditional signature routing, Automated reminders, Embedded sign in portal, Audit log export
• Who must be able to independently verify an executed contract’s signature chain (roles)? Options: Compliance, Legal, Finance, Audit/Internal Controls, IT/Security

Alerts That Would Have Actually Stopped Your Missed Deadlines—Do They Exist?

• When a renewal alert fires, who should receive it and what action should be triggered immediately? Options: Contract Owner + Legal, Procurement + Finance, Business Owner only, Escalate to management, Create a task in workflow, Other
• What lead time do you require for renewal/termination alerts to be useful? Options: >180 days, 90–180 days, 60–90 days, 30–60 days, <30 days
• Which channels should alerts use (pick all that apply)? Options: Email, Slack/Microsoft Teams, Tasking system (Jira/Asana), SMS, In‑platform dashboard only, Other
• How do you currently confirm that an alert would have prevented a missed deadline—what evidence do you need? Options: Audit trail + timestamp, Simulated timeline comparison, Manual sign‑off confirmation, Cost avoidance estimate, Other
• Give an example of a missed renewal that an alert would have needed to catch—what date, owner, and action would have prevented it?

Design the Test That Makes Legal Stop Arguing

• If you could run one validation test that would prove readiness, what single use case would you pick (describe briefly)?
• Which validation tests must pass before pilot sign‑off (select all that apply)? Options: Clause extraction accuracy threshold, Obligation + renewal alert timing, Redline versioning and merge behavior, Signature trail completeness, Repository search and retrieval speed, Other
• For each selected test, what is the pass/fail metric or acceptance criteria you will use?
• How many contracts per test case do you want the platform to process during validation? Options: 10–25, 25–100, 100–500, 500–1,000, 1,000+
• Who will be responsible for manually reviewing and adjudicating differences during validation (names/roles)?

If Things Go Sideways: Escapes, Fixes, and Rollbacks

• If validation reveals systemic extraction errors, what is your tolerance for rework vs rollback? Options: Fix in place with retest, Pause pilot and remediate, Rollback to prior repository, Abort project
• What rollback window (time) would you require to restore prior state without business impact? Options: Same day, 24–48 hours, Up to one week, Longer / case by case
• Who is the escalation owner if an unplanned data or privacy issue emerges during validation? Options: CISO / Security Lead, IT Director, Legal Ops, Vendor Success Manager, Other
• What support level do you expect during validation (select one)? Options: Dedicated on‑site support, Daily remote check‑ins, Weekly reviews, Ad hoc support only
• Describe any compliance or data residency constraints that would block a remediation or rollback option.

Sign‑off, Metrics, and Building Long‑Term Trust

• Which KPIs will determine pilot success (pick up to 4)? Options: Cycle time reduction, Extraction accuracy, Renewals avoided / cost saved, User adoption rate, Reduction in lost agreements, Time to signature
• Who must sign the final validation certificate to greenlight production rollout (roles)? Options: GC, VP Legal Ops, CPO, CFO, IT/Security Lead, Other
• How often should we measure and report these KPIs during the pilot? Options: Daily, Weekly, Biweekly, Monthly
• What sample artifacts do you want included in the validation deliverable (select all that apply)? Options: Annotated gold standard, Extraction accuracy report, Alert simulation log, Redline version history export, Signature audit export, Migration summary
• After validation, what governance or review cadence would make you feel confident the platform won’t regress? Options: Quarterly reviews, Monthly KPIs, Ad hoc on incident, Annual audit

Commitment & Next Steps: What Do You Need From Us Right Now?

• What are the top three blockers to starting validation this month (choose up to 3)? Options: Lack of sample contracts, Stakeholder availability, Security approvals, Integration access, Budget/PO, Other
• What specific accesses do we need to complete validation (e.g., SFTP, SharePoint, Doc repos, eSign API keys)?
• How soon can your team provide the annotated gold standard or the first batch of sample contracts? Options: Immediately, Within 1 week, 1–2 weeks, More than 2 weeks
• Who should be the single point of contact for scheduling, escalation, and artifacts delivery (name and role)?
• On a scale of readiness, how confident are you that validation will demonstrate the platform meets your needs? Options: Very confident, Somewhat confident, Unsure, Not confident