Quick Check — Where We Are Right Now

• What's the immediate trigger that brought us together today (select all that apply)? Options: Public undisclosed deal surfaced in media, Conference compliance inquiry, New state NIL law effective soon, Internal audit flagged gaps, Proactive review / upgrade, Other
• How recently did that trigger occur? Options: Today / within 24 hours, Within the last week, Within the last month, 1–3 months ago, Longer than 3 months
• Who first identified the issue and how did it surface (athlete, booster, public post, internal report, conference)? Options: Athlete report, Booster or collective, External media / influencer, Conference inquiry, Internal staff discovery, Other
• What immediate steps have you already taken in response (brief chronology)?

If This Went Public Tomorrow, What Keeps You Up?

• What would the worst-case headline look like for your program or institution?
• Which internal and external stakeholders would face the most exposure if that headline happened? (choose up to three) Options: Compliance Director / Office, General Counsel, Athletic Director, Conference Office, Institutional PR/Communications, Boosters / Collectives, Student-athlete(s), Other
• Have you experienced a similar public exposure before? Tell the brief story and outcome.
• Emotionally, what does that risk do to your ability to focus on other priorities? Options: Paralyzes progress across projects, Creates high, intermittent stress, Is manageable but distracting, Minimal emotional impact

Are Your Current Controls Illusions of Safety?

• How confident are you that your current spreadsheets and manual reviews would catch a high-risk undisclosed deal? Options: Very confident, Somewhat confident, Not very confident, Not confident at all
• Describe your disclosure workflow from athlete submission to final institutional record—who touches it and when?
• Which tools or systems do you currently use to track disclosures and monitoring (select all that apply)? Options: Spreadsheets, Custom internal app, Third-party compliance tool, Shared drives / folders, LMS for education, No formal tool
• How many full-time equivalents (FTEs) or staff hours per week are dedicated to NIL compliance and oversight? Options: <1 FTE / <10 hrs, 1–2 FTEs / 10–40 hrs, 3–5 FTEs, 5+ FTEs, Variable / shared responsibilities
• In the last 12 months, how many undisclosed or late-disclosed deals surfaced after-the-fact (estimate)? Options: None, 1–2, 3–5, 6–10, 10+

Where Are The Clever Ways Things Break?

• What clever loophole or blind spot worries you most—booster collectives, private intermediaries, visual-only content, or something else? Options: Booster-funded collectives, Third-party intermediaries/agents, Visual-only posts (no hashtags/captions), Private messages/deal channels, Contractual ambiguity with sponsors, Other
• Have you encountered booster collectives or intermediaries operating outside institutional oversight? If yes, describe one example. Options: Yes — documented example, Yes — suspected but undocumented, Not that I know of
• How do you currently detect visual-only social posts (images or videos without identifying text)? Options: Manual scans by staff, Keyword/hashtag monitoring only, Third-party visual scan tool, We don't reliably detect them
• Where has rule ambiguity (state vs. conference vs. NCAA guidance) caused confusion or inconsistent decisions recently?

How Would You Measure 'We Fixed It' in 90 Days?

• If we ran a focused 90-day pilot, what one outcome would convince you the greatest institutional risk was meaningfully reduced?
• Which KPIs should we track during the pilot? (pick up to three) Options: Undisclosed deal detection rate, Disclosure submission rate, Time-to-approval for disclosures, Rule engine accuracy, Social detection coverage, Audit-trail completeness, Athlete education completion
• What minimum thresholds would you require for success (e.g., detection accuracy ≥ X%, disclosure increase ≥ Y%)? Options: Detection accuracy ≥ 80%, Detection accuracy ≥ 90%, Disclosure rate improvement ≥ 20%, Disclosure rate improvement ≥ 50%, Audit-trail accepted by conference/GC
• Who inside your GC or conference team needs to sign off on those success thresholds? Options: General Counsel, Compliance Director, Conference Compliance Officer, Athletic Director, Other

Who Decides — And How Fast Can They?

• If the compliance director signs off but the general counsel pushes back, what typically happens next and how long does a resolution take?
• List the decision-makers and their role in a pilot (select all that apply, then name them if possible). Options: Compliance Director, General Counsel, Associate ADs (Compliance), Conference Officer, Athletic Director, Institutional IT/Data, Procurement
• What procurement, legal review, or institutional IT milestones commonly create the longest delays? Options: Legal contract review, Data privacy review, Security assessment, Procurement approval, None of the above
• What timeline would you consider immovable (e.g., conference review date, legislation effective date)?

Show Me a Week — Where Bottlenecks Hide

• Which recurring review, approval, or audit in your weekly cycle would cause the biggest disruption if it failed? Options: Weekly disclosure reviews, Sponsor deal audits, Education completions review, Social monitoring triage, Monthly compliance reporting
• Walk me through a typical athlete disclosure path and note where most delays or handoffs occur.
• How often do you update internal rule logic when laws or guidance change, and who makes the update? Options: Within 72 hours by in-house team, Within 72 hours via vendor, Takes days–weeks, Ad-hoc, no set cadence
• Which data feeds or integrations are missing today that would materially improve monitoring (social APIs, contract databases, booster registries)?

What Would Make You Trust a Pilot Enough to Expand?

• What single tangible result would turn a skeptical stakeholder into an active advocate for expansion?
• Which sport and approximate roster size would be the ideal pilot for meaningful signal without overtaxing teams? Options: Single high-profile sport (e.g., football, basketball), Mid-size sport (e.g., baseball, volleyball), Multiple small sports, Cross-sport sample
• What specific data access, feeds, or permissions must be granted before launch (select all that apply)? Options: Athlete social handles, Roster and eligibility feeds, Contract/deal uploads, Booster registry access, Institutional SSO/ID integration, None / minimal data
• What maximum duration would you accept for a pilot before deciding go/no-go? Options: 30 days, 60 days, 90 days, Longer than 90 days

What Could We Deliver Fast That Changes the Game?

• What is one small capability we could deliver in 2–4 weeks that would materially lower your exposure? Options: Automated visual social scans, Instant disclosure reminders for athletes, Rule engine update for a specific state, Audit-trail export for conference, Booster flagging dashboard
• Which of those quick wins would be hardest to get athletes to adopt, and why?
• Who would need to enable or sign off internally to deploy a quick capability (select all that apply)? Options: Compliance Director, General Counsel, Athlete Ops / Head Coach, IT / Security, Communications
• How would you want us to demonstrate impact of that quick capability in the first 30 days (reporting cadence, sample alerts, pilot user interviews)? Options: Weekly KPI reports, Sample detected cases with audit trail, Stakeholder demo calls, Athlete feedback survey

Agreeing Next Steps — Who Does What and When

• If we leave this conversation agreeing to two concrete actions, what must they be?
• Who on your side will be the operational owners for the pilot (select roles and optionally list names)? Options: Compliance Director, Associate AD (Compliance), General Counsel, IT/Data Owner, Athlete Education Lead
• What is an acceptable target window to launch the pilot (choose one)? Options: Within 2 weeks, 2–4 weeks, 4–6 weeks, 6+ weeks
• Are there procurement, contracting, or data agreements that must be completed before we begin? If yes, what is the expected timeline? Options: Yes — legal/procurement required (timeline provided below), No — ready to proceed, Unsure — need guidance

Start Here: A Quick Snapshot of Today

• How do you currently track athlete NIL disclosures day-to-day? Options: Spreadsheets (manual), Homegrown database, Third‑party platform, Shared drive + email threads, Combination of the above, Other
• Roughly how many active disclosure records or new deals does your office handle each month? Options: 0–25, 26–50, 51–100, 101–250, 250+
• Who is directly responsible for initial collection, verification, and filing of disclosures? Options: Compliance Director, Associate AD – Compliance, Compliance Coordinator, Graduate assistant/team of students, Athletics admin staff, Shared with Legal, Other
• Walk me through the typical lifecycle of a disclosure in your current process—from athlete submission to final record. Please include handoffs.
• Where do you store historical disclosure records and supporting materials (contracts, receipts, screenshots)? Options: Shared drive (eg. Google/OneDrive), Local spreadsheets, Institutional records system/CRM, LMS or training system, Paper files, Third‑party vendor portal, Other
• How confident would you be that your current records would withstand a conference or NCAA compliance audit? Options: Very confident, Somewhat confident, Not confident, Unsure

If One Missed Post Could Start an Investigation, How Would You Explain It?

• How often do undisclosed or questionable deals surface publicly (media, boosters, social posts) in a given year? Options: Never, Once, 2–3 times, Quarterly, Monthly or more
• Tell us about the most recent time a social post or media story created compliance exposure—what happened and what did it reveal about your process?
• When an undisclosed deal appears, what are the most common root causes you identify? Options: Athlete unaware of rules, Process too cumbersome, Booster collective involvement, Lack of monitoring coverage, Data/version control errors, Other
• On average, how long passes between a problematic post and your team becoming aware? Options: Same day, 1–3 days, 4–7 days, 8–30 days, Over 30 days
• What immediate evidence or documents do you wish you had available when responding to a public exposure? Options: Timestamped audit trail, Original disclosure form, Conversation logs/emails, Proof of education/training, Social post archive/screenshots, Other
• How does handling public exposures typically affect your team—operationally and emotionally?

Where the Spreadsheet Stops Being Enough

• If spreadsheets are central to your process, what three problems do they cause most often?
• Which day‑to‑day tasks tied to disclosures consume the most staff hours? Options: Manual data entry, Reconciling conflicting records, Chasing athletes for signatures, Generating reports for leadership, Responding to flagged posts, Other
• How frequently do you encounter version control issues or multiple conflicting copies of disclosure data? Options: Never, Rarely, Sometimes, Often, Constantly
• Have you missed deadlines or failed to capture key evidence because of manual tracking limitations? Options: Yes, multiple times, Occasionally, Rarely, Never
• If you could remove one manual step right now, which would deliver the most relief?
• What proportion of your compliance workload feels reactive (firefighting) versus proactive (prevention, education)? Options: Mostly reactive, More reactive than proactive, Balanced, More proactive than reactive, Mostly proactive

Blind Spots: The Things You Can't See Until It's Too Late

• Which social platforms and channels are you intentionally monitoring for athlete brand activity today? Options: Instagram, TikTok, X/Twitter, YouTube, Facebook, Snapchat, Third‑party sites/media, Other
• Are you using any automated visual recognition (logos, products) or are you relying on text/hashtags only? Options: Image/video recognition in use, Text/hashtag based monitoring only, Manual human review only, No active monitoring
• What blind‑spot concerns keep you up at night (booster collectives, surrogate deals, dark posts, influencer layers)?
• Approximately what percentage of flagged content is a true compliance concern versus false positive noise? Options: <1%, 1–5%, 6–15%, 16–30%, >30%
• Describe your current process for triaging flagged content—who reviews, what are timelines, and how are decisions documented?
• Which types of visual or indirect sponsorships are hardest for you to detect today? Options: Logos on products, Branded locations, Paid shoutouts, Event appearances, Collective‑funded deals, Cross‑platform campaigns, Other

When Rules Change Overnight, Who's Left Holding the Bag?

• How do you currently monitor and track state, conference, and NCAA NIL rule changes? Options: Dedicated staff/person, Legal/GC office, Manual monitoring of sources, Vendor/regulatory feed, We rely on ad hoc alerts, Other
• When a regulatory change occurs, how fast can you update internal policies and communicate to athletes? Options: Within 24 hours, 48–72 hours, 1 week, Several weeks, No reliable SLA
• Has a recent rule change ever impacted a signed or pending deal? Tell us how you handled it. Options: Yes—we adjusted or canceled deals, Yes—handled case-by-case, No impact to date, Not sure
• Who needs to approve regulatory interpretation and outbound communications (check all that apply)? Options: Compliance Director, General Counsel, Conference office, Athletic Director, External counsel, Other
• What SLA would you require from a vendor for updating rule logic after an official change? Options: Same day, Within 72 hours, Within 1 week, Standard quarterly updates, Flexible depending on change
• What is the single biggest risk to your program if regulatory rules are interpreted or applied incorrectly?

What Would True Confidence Look Like in 90 Days?

• Which pilot KPIs would prove the platform materially reduces your institutional risk? Options: Reduction in undisclosed deals, Increase in disclosure completion rate, Social detection coverage, Rule accuracy, Time-to-resolution for flagged items, Audit‑trail completeness, Athlete portal adoption
• Set a measurable target for undisclosed deals reduction or disclosure rate improvement you’d consider a success after 90 days. Options: 10% improvement, 25% improvement, 50%+ improvement, Specific numeric target (enter below)
• What is an acceptable false positive rate for social monitoring that still allows your team to operate efficiently? Options: <1%, 1–5%, 6–10%, 11–20%, I need guidance
• How many sports or teams would you include in an initial pilot to get a representative sample? Options: Single sport, 2–3 sports, Department subset (3–6 teams), Majority of teams
• Who should be on the pilot steering committee to approve go/no‑go decisions? Options: Compliance Director, Associate AD – Compliance, General Counsel, Athletic Director, IT/Security, Student‑athlete representative, Other
• What objective criteria would you require to greenlight full rollout after the pilot?

Ready to Change? What Support Would Remove the Friction

• What commercial, legal, or data‑privacy concerns usually slow vendor contracting for your office? Options: Data ownership, PII/FERPA concerns, Indemnity/limitation clauses, Integration costs, Length of contract, SLAs and uptime, Other
• Which internal stakeholders must be involved in procurement and implementation sign‑off? Options: Compliance, General Counsel, Athletic Director, IT/Security, Procurement, University Privacy Office, Other
• What system integrations are must‑haves for a successful deployment (eg. SSO, student records, LMS, analytics)? Options: Single Sign‑On (SSO), Student Information System, Email/calendar, LMS/training system, Athletics CRM, BI/reporting tools, Social API access, Other
• Which training formats produce the best athlete adoption for you—live sessions, recorded modules, in‑portal microlearning, or ongoing office hours? Options: Live workshops, Recorded on‑demand, LMS microlearning, Office hours/Q&A, Peer-to-peer champions, Combination
• What level of vendor transparency and reporting do you expect during a pilot (dashboard access, raw data export, weekly summaries)? Options: Full dashboard access + raw export, Weekly executive summary, Ad hoc reports on request, Minimal reporting (pilot only)
• If we proposed a 60–90 day pilot with agreed KPIs, what would be your single biggest hesitation to starting?

Small Wins That Prove Big Value

• If we could deliver one meaningful result in the first 30 days, what outcome would make you most comfortable to continue?
• Which specific processes could realistically be fully automated or simplified within the first month? Options: Disclosure intake form, Automated reminders to athletes, Social media scanning for logos, Rule‑based deal triage, Audit‑trail capture, Reporting exports
• What minimum reporting package would you need to show leadership immediate pilot value? Options: Weekly KPI dashboard, Incident log + root causes, Audit trail snapshots, Athlete adoption metrics, Executive 1‑page summary
• Who will own day‑to‑day operations of a pilot on your side (name/role) and how many hours per week can they dedicate? Options: Compliance Director (0–5 hrs), Compliance Coordinator (5–15 hrs), Dedicated resource (15+ hrs), Shared responsibility across team, TBD
• Are there any data access limitations, legal restrictions, or privacy considerations we must resolve before data sharing?
• What would be the ideal next step after this discovery call to get a pilot started? Options: Technical scoping session, Legal/data sharing review, Executive briefing, Pilot proposal with cost, Other

Starting Point — Tell Me About Your Program

• How would you describe the current maturity of your NIL compliance program? Options: Ad hoc / manual spreadsheets, Defined processes but manual, Partially automated with tools, Fully supported by a compliance platform
• Who is primarily responsible day-to-day for tracking disclosures and reviews? Options: Compliance Director, Associate AD for Compliance, Compliance Coordinator / Staff, Legal / GC team, Shared across roles
• Roughly how many active athlete deals do you track per year (estimate)? Options: <100, 100–300, 300–600, 600–1,000, >1,000
• Which tools or methods are you currently using to manage NIL activity? Options: Spreadsheets, Homegrown database, Commercial NIL platform, Email + shared drives, Paper / PDFs, Other
• When you think about the last time an NIL issue caused stress, what stands out—what happened and how did it feel?
• What event most recently triggered a change in your approach to NIL oversight (e.g., public exposure, conference inquiry, law change)? Options: Public media exposure, Conference review, State law change, NCAA guidance, Internal audit, Other

If One Undisclosed Deal Appeared Tomorrow…

• When an undisclosed deal surfaces publicly, what usually surprises you most about how it unfolded? Options: Timing of discovery, Where it was posted (visual vs. text), How many people knew, Gaps in documentation, Speed of media amplification
• How long does it typically take from when you suspect a missing disclosure to when you can confirm and document it? Options: Same day, 1–3 days, 4–10 days, More than 10 days
• Tell me about a recent example where an undisclosed relationship became a compliance issue—who found it, what evidence mattered, and what was the outcome?
• When these incidents happen, which consequence worries you most? Options: Regulatory penalties/fines, Conference/institutional reputational damage, Internal discipline challenges, Inability to prove oversight in review, Fan/booster backlash
• How confident are you today that your existing records would satisfy a conference or NCAA review? Options: Very confident, Somewhat confident, Uncertain, Not confident at all

Where Your Spreadsheets Secretly Break

• Do you believe your current manual processes are missing patterns that an automated system would catch? Options: Yes — frequently, Sometimes, Rarely, Not sure
• Which parts of the disclosure workflow are most manual or error-prone for your team? Options: Intake of athlete disclosures, Verification of sponsor legitimacy, Linking social posts to deals, Audit trail generation, Reporting to conference
• Approximately how many staff-hours per week are spent on manual NIL tracking, reconciliation, and reporting? Options: <5 hrs, 5–15 hrs, 15–40 hrs, >40 hrs
• Where do most errors show up—missing metadata, inconsistent naming, missed social posts, or something else? Options: Missing metadata, Inconsistent entries, Missed social posts/visuals, Duplicate records, Other
• If spreadsheets are creating blind spots, which blind spot worries you most and why?

Who Really Decides — and Who Gets Blamed?

• If institutional oversight failed and a regulator questioned your program, who internally would bear the brunt of responsibility? Options: Compliance Director, Athletics Director, General Counsel, Specific sport AD/coach, Shared across leadership
• List the stakeholders who must sign off on policy changes, vendor data access, or a pilot (select all that apply). Options: Compliance Director, AD/CEO, General Counsel, IT/Data Security, Finance, Student-Athlete Advisory Committee, Conference Office
• How aligned are those stakeholders today on priorities like speed of disclosure review versus thorough legal review? Options: Fully aligned, Mostly aligned, Some misalignment, Significant disagreement
• Describe any political or cultural dynamics—booster influence, coach pressure, athlete privacy concerns—that have shaped how NIL oversight is handled here.
• When decisions are made about escalation, who is the final decision-maker and how is that communicated? Options: Compliance Director, General Counsel, AD, Committee, No clear owner

What Would Regulatory 'Good' Actually Look Like Here?

• If a regulator audited you tomorrow, what single gap would you most fear they'd highlight? Options: Insufficient audit trail, Incomplete disclosures, Poor social monitoring, No formal workflows, Inadequate athlete education
• Which of these measurable success signals would have the biggest impact on your risk posture? Options: % reduction in undisclosed deals, Audit-trail acceptance by conference, Rule accuracy threshold, Detection coverage of social posts, Speed of disclosure review
• What targets would you consider a clear win for a pilot (select realistic ranges)? Options: Disclosure rate >90%, Detection coverage >80%, Rule accuracy >85%, Avg review time <48 hours, Audit-trail complete 100%
• How often would you want automated regulatory updates and why (frequency and rationale)? Options: Real-time/within 72 hours, Weekly, Monthly, On-demand with notification
• What evidence or artifacts do you need to feel comfortable that the institution could defend its oversight in a review?

What's Stopping a Faster, Safer Pilot?

• What's the single biggest friction that typically prevents pilots from launching or succeeding here? Options: Data access delays, Legal/commercial negotiations, Athlete buy-in, IT/security approval, Resource availability
• Which legal or commercial items still need resolution before a pilot (select all that apply)? Options: Contract terms, Data processing agreement, SLAs for regulatory updates, Liability/indemnity, Pilot length and acceptance criteria
• How long does your legal/contract review process normally take for vendor pilots? Options: <2 weeks, 2–4 weeks, 4–8 weeks, >8 weeks
• What approvals or signatures are absolute blockers if not obtained (name roles or committees)?
• If we shaved two weeks off the setup timeline, what would that enable for your department this quarter?

Data & Integration Reality Check

• How confident are you that the data feeds you rely on (roster, contracts, payments, social handles) are accurate and accessible? Options: Very confident, Somewhat confident, Low confidence, Not accessible currently
• Which of these data feeds can you provide for a pilot without IT changes? Options: Roster with IDs, Athlete contact info, Existing disclosure records, Booster/collective registry, Social handle list
• Who owns each integration or feed on your side (list roles and contact points)?
• Have you experienced missing or delayed feeds in the past 12 months? If yes, how often and what caused them? Options: Never, Rarely (1–2x), Occasionally (3–6x), Frequently (>6x)
• Are there regulatory data subscriptions (state law feeds, conference bulletins) you must subscribe to before a pilot? Options: Yes — already subscribed, Yes — need to subscribe, No required subscriptions, Unsure

Athlete Behavior & Education — The Human Wildcard

• How realistic is it to expect full, timely athlete disclosure without a targeted education and incentive program? Options: Unrealistic without it, Helpful but not required, Neutral, Not needed
• What formats are you currently using to educate athletes about NIL obligations? Options: Online modules, One-pagers/handbooks, Team meetings, Live Q&A sessions, In-person workshops
• What percentage of athletes typically complete required education within a season? Options: >90%, 70–90%, 50–69%, <50%
• Describe common athlete objections or blind spots that lead to missed disclosures (e.g., misunderstanding visuals, booster deals, privacy concerns).
• Have you used incentives, penalties, or gamification to improve disclosure rates? What worked or failed?

Pilot Design — What Success Actually Requires

• Could a two-month pilot truly validate your readiness for a full rollout—or are there outcomes only visible long-term? Options: Yes—short pilot sufficient, Mostly—need some extensions, No—requires longer pilot, Unsure
• Which sport would you pick for a representative pilot and why (capture risk profile and visibility)?
• Select the KPIs you’d require from the pilot to consider it successful (choose top 3). Options: Disclosure rate, Detection coverage of social posts, Rule accuracy, Avg review time, Audit-trail completeness, Athlete portal adoption
• Who will own pilot day-to-day responsibilities on your side (identify roles and backup owners)?
• What specific acceptance criteria would make you say 'go' or 'no-go' at pilot close?
• What would constitute a fatal flaw during the pilot (single item that would stop rollout)? Options: Data quality issues, Poor detection accuracy, Athlete non-participation, Security concerns, Unresolved legal terms

Next Steps & Commitments — Who Will Own This?

• What’s the most likely reason this project would stall after initial enthusiasm? Options: Lack of operational ownership, Legal/commercial delays, IT/security roadblocks, Insufficient athlete engagement, Budget constraints
• Which approvals need to be secured to begin Pre-Deployment Readiness (data access, athlete consent, legal sign-off, IT security)? Options: Data access, Athlete consent, Legal sign-off, IT/security approval, Budget approval
• Who would be the configuration and integration owner on your side and who is their backup?
• What is your ideal target date to start a pilot (month/quarter) and what internal dependencies must be resolved first? Options: Within 2 weeks, Within 1 month, Within quarter, Next quarter or later
• Which readiness items below must be in place before execution (select all that apply)? Options: Roster feed live, Athlete portal access, Legal/contract signed, Data sharing agreement, IT security sign-off, Regulatory feed subscriptions
• If we committed to a short joint-workshop next week, what would you most want to resolve during that session?

Start Here: What Brought You In Today?

• What immediate event or concern prompted you to explore NIL compliance tooling today? Options: A public undisclosed athlete deal, A conference inquiry or audit, Upcoming state law change, Internal capacity strain, Other
• Briefly describe the most recent example of a disclosure or monitoring issue you had (what happened, who saw it, and what the near-term consequence was).
• How frequently do incidents like that occur at your institution? Options: Weekly, Monthly, Quarterly, Rarely / Ad hoc
• How urgent is resolving this—what's your target timeframe for a meaningful pilot or mitigation (choose the closest)? Options: Within 30 days, Within 60–90 days, Within this quarter, No firm timeline yet
• Who on your team will primarily own follow-up conversations and pilot coordination (role/title)?

If Left Unchecked, How Bad Could This Get?

• Imagine a high-profile undisclosed deal goes viral—what institutional consequences keep you awake at night? Options: Public relations fallout, Conference sanction/inquiry, NCAA investigation, Loss of donor/booster relationships, Legal exposure, Other
• How many undisclosed or questionably disclosed athlete deals do you suspect exist right now (order-of-magnitude)? Options: None / confident, 1–5, 6–20, 20+
• When similar exposures have happened elsewhere, what were the ripple effects you noted (staff time, policy changes, compliance burden)?
• How long has this level of risk been building in your program? Options: Just started, A few months, 1–2 years, Several years
• What would be the single clearest signal that you’d categorize the situation as ‘out of control’?

What Are You Quietly Tolerating?

• What manual processes or spreadsheets are you still relying on for disclosures and why haven’t they been replaced?
• Which of the following current gaps cause the most daily friction for your team? Options: Missed disclosures, Slow review times, Fragmented audit trail, Poor social coverage (visual posts), Rule engine inaccuracies, Athlete portal confusion
• Quantify the compliance team’s current capacity—how many full-time equivalents (FTEs) support disclosures and monitoring? Options: <1 FTE, 1–2 FTEs, 3–5 FTEs, 6+ FTEs
• How do these tolerated problems make the team feel—frustrated, embarrassed, resigned, defensive, or something else? Options: Frustrated, Overwhelmed, Defensive, Resigned / Doing minimum, Motivated to change, Other
• Can you share a specific example where a manual process directly failed to catch an issue? What happened next?

Who’s Deciding—and Who’s Being Blamed?

• Who are the decision-makers and approvers for NIL compliance changes (list roles: compliance director, GC, ADs, conference officer, others)?
• Where have you experienced misalignment between legal, compliance, and athletics on disclosure expectations?
• Which stakeholder’s buy-in would be hardest to secure and why? Options: General Counsel, Athletic Director, Conference Office, Boosters/Donors, Head Coaches, Other
• Who outside your department (e.g., boosters, agents, camp directors) impacts disclosures or deal flows, and how cooperative are they? Options: Very cooperative, Somewhat cooperative, Reluctant, Adversarial / unknown
• If an external regulator asked for proof of oversight, who would be responsible for preparing that evidence today?

What Does 'Safe' Look Like in 90 Days?

• If we ran a 90-day pilot, which primary success signal would make you say it succeeded? Options: Significant reduction in undisclosed deals, Audit-trail accepted by conference, Rule engine reaches agreed accuracy, Athlete adoption rate meets target, Faster review/approval times
• Which KPI thresholds would feel materially successful to you (provide numbers where possible)?
• How tolerant are you of false positives from social monitoring in a pilot (how much extra triage is acceptable)? Options: Very low (<=5% extra triage), Moderate (5–15%), High (15–30%), Unsure
• What reporting cadence and format would you need to feel confident during the pilot (weekly dashboard, biweekly review, monthly exec summary)? Options: Weekly operational dashboard, Biweekly review with team, Monthly executive summary, Ad-hoc as issues emerge
• Are there specific sports, rosters, or athlete segments you want included or excluded in the pilot (e.g., revenue sport, high-profile athletes)?

What Would Make You Say 'No'—Deal Breakers?

• Which contractual or operational limitations would immediately prevent you from moving forward? Options: No data access, Vendor legal terms unacceptable, Insufficient SLAs for regulatory updates, Price exceeds budget, Inability to integrate with key systems, Other
• What minimum data access and integrations must be available for a pilot to be meaningful (roster feed, social handles, booster lists, payment records)?
• What security/privacy certifications or controls are mandatory for your institution (e.g., FERPA considerations, institutional security review)? Options: Yes—mandatory, Preferable but not required, Not applicable/unsure
• How flexible is your procurement team on contract length, pilot-to-production conversion, and renewal terms? Options: Very flexible, Somewhat flexible, Rigid, Unsure
• What timeline or milestone would you require before legal/commercial teams sign off on a pilot?

Who Will Run the Pilot—And Do They Have Bandwidth?

• Who will be the day-to-day pilot owner and who is the executive sponsor (role/title)?
• Do you have an internal configuration owner and IT contact available for a 4–6 week setup window? Options: Yes—both assigned, Partially—need to assign, No
• What internal systems should the pilot integrate with and how accessible are those feeds (easy, requires approvals, restricted)? Options: Student information/roster feed, Athlete portal/SSO, Payment/boosters record, Social account lists, None / manual
• What training and education will athletes and staff require during the pilot (live sessions, recorded modules, quick reference guides)? Options: Live training, Recorded modules, Quick reference guides, Office hours/support desk, No training needed
• What internal blockers (IT approvals, data governance, coach resistance) could delay pilot start and how long would each typically take to resolve?

What Would Success Change for You—Beyond the Pilot?

• If the pilot met your success signals, how would day-to-day operations look different in 6 months?
• How do you envision scaling beyond the pilot sport—phased by sport, full-dept rollout, or mixed approach? Options: Phased by sport, Department-wide after pilot, Hybrid approach, Unsure
• What governance or policy changes would you plan to put in place once the platform is trusted? Options: Formal audit trail policy, Regular booster reporting, Athlete disclosure mandates, Automated rule updates, Other
• Who else—outside compliance—would need to be convinced to adopt the platform long-term (list roles and likely objections)?
• What ongoing support and update cadence would you expect from a vendor to keep pace with fast-moving NIL rules? Options: Weekly regulatory alerts, 72-hour law change updates, Monthly rule reviews, Quarterly strategy check-ins

Are You Ready to Decide—and What’s Next?

• Where are you in the decision process today (just exploring, gathering quotes, ready for pilot, budget approved)? Options: Just exploring, Gathering options, Ready to pilot—need procurement, Budget approved—ready to sign
• Who else needs to be involved in the next meeting for this to move forward (legal, IT, AD, conference contact)?
• What would you like the vendor to deliver as the next step from this discovery (technical scoping, pilot proposal, legal terms outline, demo tailored to sport)? Options: Pilot proposal with KPIs, Technical integration scoping, Tailored demo, Commercial/ legal draft
• What are the top three things we should fix first if we run a pilot with you?
• Is there anything else you want us to know that would materially affect the pilot or evaluation (political dynamics, upcoming events, sensitive athlete situations)?