Getting Oriented: A quick snapshot of where you are now

• Tell me briefly about where you are in your athletic career right now and what prompted this conversation
• How many years remain on your current contract, including team options and guaranteed salary years Options: 0 (free agent now), Less than 1 year, 1 year, 2 years, 3+ years, Unsigned/college player
• When did you last negotiate a professional contract or a major endorsement, and who led that process for you
• Who currently makes the first call when a team or brand reaches out about you Options: You, Family member, Current agent, Manager/representative, Legal counsel, Unsure
• Which parts of representation feel most important to you right now, rank priorities Options: Contract negotiation, Endorsements and sponsorships, Financial planning and tax, Media and public relations, Post-career planning, Legal review, Other
• Would you say your primary career goal this season is proving performance, earning a long-term deal, increasing marketability, or something else Options: Prove performance, Secure long-term deal, Maximize current earnings, Build brand/marketability, Prepare for post-career, Other
• How ready are you to switch representation if an offer aligned with your goals appears within the next 30, 60, or 90 days Options: Immediately (within 30 days), Within 60 days, Within 90 days, Not looking to switch, Unsure

Where Current Representation Falls Short

• If the next contract cycle leaves you financially exposed, what part of your current representation would you blame first
• Describe the last negotiation or endorsement where you felt under-supported, and what specifically went wrong
• Who in your current advisor group first hears about offers and public inquiries Options: You, Family member, Agent, Manager, Legal counsel, Unsure
• On average, how often do you receive clear status updates during an active negotiation Options: Daily, Every few days, Weekly, Only at milestones, Rarely
• Which past missed opportunities still feel unresolved and why
• Would losing control of your brand in an endorsement deal be a deal-breaker for you Options: Yes, Maybe depending on the deal, No
• Tell me about a negotiation that felt mishandled and what you would change if you could do it over
• What single contractual issue, if unresolved, would make you walk away from signing with your current representative

How You Know You Are Winning, and What Counts

• What career signal would have to move before you considered a new representation strategy
• List the three metrics you or your team track most closely Options: Guaranteed salary and guarantees, Total compensation including incentives, Playing time and starts, Marketability (social reach, engagement), Endorsement revenue, Post-career preparation
• How often do you review those metrics with your advisors Options: Weekly, Monthly, Quarterly, Only before major decisions, Never
• Describe a recent data point that changed how you thought about your next contract or endorsement
• Which timeline matters more to you right now, the next contract year or the next three years, and why Options: Next contract year, Next three years, Both equally, Depends on health/performance
• Would a clear plan to achieve a specific guaranteed salary target make you more likely to change representation Options: Yes, Maybe, No
• If a projected contract model showed a 20% higher guaranteed value from a different approach, what would stop you from moving forward within two weeks

Brand & Endorsement Compass: what you will and will not do

• Name a type of brand or endorsement that would damage your long-term reputation even if it paid well
• Which parts of your personal brand do you want to protect or amplify this season Options: Performance excellence, Community work, Family values, Style and image, Entrepreneurship, Other
• How many current endorsements do you have and which revenue band best fits most of them Options: None, One, 2-4, 5+
• Tell the story of the last brand partnership you were proud of and what made it a good fit
• Would you prefer a few larger partnerships or many smaller deals that align closely with your values Options: A few large, high-value deals, Many smaller, tightly aligned deals, A mix
• Which person or role approves brand fit decisions for you and what are the top three criteria they use
• What single concern about endorsement exposure would make you decline an otherwise lucrative offer

Advisor Network and Decision Rights

• If there is a conflict of interest among your advisors, what outcome would you accept and what would be unacceptable
• List everyone on your advisory team and their primary responsibilities
• How often do you meet with your financial planner and legal counsel during contract negotiation periods Options: Weekly, Monthly, Only for major decisions, Rarely
• Which advisor do you trust most for contract strategy and why
• Share a specific example of when advisor advice cost you an opportunity and what you learned from that
• Would anyone on your advisory team object to signing a new representation agreement within 30 days Options: Yes, No, Unsure
• Which person(s) must sign off internally for you to change representatives immediately

What Alternatives Are You Weighing Right Now

• What's the most persuasive reason you've heard to stay with your current representation or to handle deals yourself
• Which external options are you actively considering right now Options: Keep current agent, Switch to another agent or agency, Negotiate without an agent, Manage deals with family, Hire a brand manager only, Unsure, Other
• Have you requested proposals or interviewed other agents, and if so who led those conversations Options: Yes, multiple agents, Yes, one agent, No, but planning to, No
• What would have to be true about your current representation for you to decide to stay
• Is anyone inside your circle proposing that you manage deals without an outside representative Options: Yes, family, Yes, financial advisor, Yes, team or coach, No
• Would a written performance promise or demonstrable case studies change your inclination to switch Options: Yes, Maybe, No
• If another representation offered to guarantee a timeline for a specific outcome, would you be willing to sign before seeing a full contract Options: Yes, Maybe with conditions, No

Operational Readiness and Constraints

• If we need immediate access to your contracts, medical clearance, or financial statements, what could prevent you from sharing them within 7 days
• Which documents are already digitized and ready to share Options: Current team contract, Endorsement agreements, Existing agent contract, Financial planning documents, Insurance policies, Medical records, None of the above
• Which person or role holds final signatory authority on your existing contracts or endorsements Options: You, Parent/guardian, Manager, Current agent, Legal counsel, Other
• Estimate the number of people from your side who would need to be involved in onboarding and list their roles
• Are there league or governing body approvals, registrations, or restrictions that could delay a change in representation Options: Yes, registration required, Yes, waiting period applies, No major approvals, Unsure
• Would your financial advisor require a formal data access agreement before we integrate planning tools Options: Yes, No, Unsure
• Is there any document or approval that, if unavailable, would prevent onboarding within 30 days, and if so which

Decision Moments and Next Steps

• If we can deliver a clear plan that increases guaranteed earnings and protects brand fit, what would make you sign within two weeks
• Which timeline feels realistic for you to make a decision Options: Immediately, Within 2 weeks, Within 1 month, 2-3 months, Undecided
• Provide the names and roles of people who need to be involved in the final decision and their availability
• Would you accept a two-week pilot focused on endorsement outreach and contract modeling to evaluate fit Options: Yes, Maybe, No
• How should we document success on the first 90-day engagement and what single metric would convince you to continue
• Name any non-negotiable terms you require in a representation agreement
• If everything lines up, are you prepared to sign a representation agreement within your stated timeline Options: Yes, within timeline, Only after final review, No, need more time, Unsure

• Representation Strategy Walkthrough

• Confirm the current state and its cost to your career
• You confirm the presented negotiation pathway preserves your negotiating power and timing for offers.
• Prepare a draft negotiation timeline with target milestones and contingency triggers based on today's agreed scenario.
• You confirm the endorsement plan aligns with your personal brand and identifies conflict boundaries you will not accept.
• Walk through the proposed negotiation pathway using your real scenario
• Provide copies of all existing contracts, endorsements, and advisor agreements for audit.
• Run a modeled earnings and cashflow projection for the demonstrated contract scenarios and deliver before the follow-up session.
• You confirm the financial planning scenarios address post-career solvency and show how fees and cashflow will be handled across outcomes.
• Walk through the endorsement approach against your brand and pending opportunities
• Walk through the financial planning response tied to outcome scenarios
• You agree on the remaining evidence and deliverables required before a mutual commitment decision.
• List any endorsement brands or industry categories you want explicitly excluded due to conflict or personal preference.
• Prove the integrated timeline and owner map
• Validate alignment with what you told us

• Representation Strategy Walkthrough
• Representation Strategy Deck
• Representation Strategy Brief

• meeting
• slides
• document

• Execute Representation Agreement
• Negotiate Team and League Contracts
• Manage Free Agency and Contract Extensions
• Secure Endorsement and Sponsorship Agreements
• Activate Endorsement Deliverables and Compliance
• Establish Financial Trusts and Disbursement Accounts
• Implement Cashflow and Payment Management
• Procure Insurance and Disability Coverage
• Coordinate Media, PR, and Personal Branding
• Manage Brand Licensing and Merchandising Deals
• Negotiate Release from Prior Representation
• Execute Post-Career Business and Speaking Contracts

Execute Representation Agreement

• Do you have an existing representation agreement that we must review before drafting a new retainer? Options: Yes, No
• How long do you want the initial term of the retainer to be (months or years)? Options: 6 months, 12 months, 24 months, Custom
• Which commission structure do you prefer for team contracts and separate endorsement deals? Options: Percentage of contract value, Flat fee per negotiation, Tiered percentage, Hybrid
• What specific prior-contract clauses (termination notice, buyout amounts) must be preserved from any existing agreement?
• Who will be the athlete's authorized signer for the retainer and can you provide the signer name and ID type?
• What evidence will validate that the representation agreement execution is complete (for example, fully signed retainer, league agent registration filed, e-signature audit)? Options: Signed retainer in system, League agent registration confirmation, E-sign audit trail, All of the above

Negotiate Team and League Contracts

• Do you currently have an active player contract that will affect negotiation timing for extensions or free agency? Options: Yes - active contract present, No - contract expiring, Unsigned/undetermined
• What contract elements are highest priority: guaranteed money, signing bonus structure, roster guarantees, trade protections, or termination language? Options: Guaranteed money, Signing bonus structure, Roster guarantees, Trade protections, Termination language
• Which league collective bargaining agreement (CBA) provisions must we reference for bonuses, per-game pay, or injury guarantees?
• Who should be the primary contact for medical clearance records and official injury reports used during negotiation? Options: Athlete, Team doctor, Athlete's medical advisor, Other
• When negotiating, what is your minimum acceptable guarantee threshold in the next contract (dollar amount or percentage of total)?
• What evidence will confirm a successful team contract negotiation (for example, executed league contract and cleared league approval)? Options: Fully executed league contract, League payroll registration confirmation, Payment schedule in escrow, All of the above

Manage Free Agency and Contract Extensions

• How many active free agency windows do you anticipate during the representation term (e.g., immediate, next season, two seasons)? Options: Immediate (this window), Next season, Within two seasons, No anticipated free agency
• What timeline milestones should we use for extension talks (pre-draft visit, 60 days before contract expiry, post-injury recovery)? Options: Pre-draft visit, 60 days before expiry, Post-injury recovery, Custom timeline
• Which negotiation levers are acceptable to you during free agency: multi-year guarantees, incentives, signing bonus front-loading, or option years? Options: Multi-year guarantees, Incentives, Signing bonus front-loading, Option years
• Who on your team should be notified of offer sheets or franchise-tag decisions (attorney, financial advisor, family member)? Options: Attorney, Financial advisor, Family member, Other
• What prior roster conflicts by position or existing client overlaps should we avoid when approaching teams or other clients?
• Describe any salary-cap considerations or previous team obligations (e.g., guarantees owed by prior team) that will constrain offers.

Secure Endorsement and Sponsorship Agreements

• Which existing endorsement deals must be disclosed and audited before signing new sponsorships (provide contract names or brands)?
• What brand categories are off-limits for the athlete (alcohol, gambling, politics, competing sportswear) and must be enforced in deal selection? Options: Alcohol, Gambling, Politics, Competing sportswear, None
• What deliverable cadence do you expect in activation schedules (number of posts per month, appearances per season, content rights duration)? Options: Monthly posts, Seasonal appearances, Per-campaign schedule, Custom
• Who will approve creative assets and brand messaging: athlete, athlete's family, or a designated brand manager? Options: Athlete, Family member, Designated brand manager, Agency creative lead
• Which compensation mix do you prefer for endorsements: guaranteed fee, performance bonuses, product equity, or revenue share? Options: Guaranteed fee, Performance bonuses, Product equity, Revenue share
• Provide any sample term sheet or recent endorsement contract clauses you want replicated or avoided (attachment or summary).

Activate Endorsement Deliverables and Compliance

• Do you have brand guidelines and logo usage rules we must enforce for each endorsement (upload or summarize)? Options: Yes, No
• Which social media handles and login credentials will you provide for activation tracking and content posting?
• What approval SLAs do you require for creative deliverables (e.g., 48 hours for social posts, 5 business days for video)? Options: 24 hours, 48 hours, 5 business days, Custom
• Who will be responsible for compliance tracking and reporting for exclusivity windows and non-compete clauses? Options: We handle tracking, You provide a compliance contact, Shared responsibility
• List any measurement metrics that must be reported to sponsors (impressions, engagement rate, click-throughs, attendance figures). Options: Impressions, Engagement rate, Click-throughs, Attendance figures, Other
• Identify any legal approvals required from league or team prior to activation (uniform usage, sponsor conflicts tied to the collective bargaining agreement). Options: Team approval, League approval, No external approvals required, Unknown

Establish Financial Trusts and Disbursement Accounts

• Do you require a dedicated fiduciary trust account for guarantee deposits and endorsement holdbacks? Options: Yes, No, Maybe - need recommendation
• Which bank account details and tax ID will be used for disbursements and can you provide ownership verification documents?
• What beneficiary designations or payee splits must be configured on the trust for family members or advisors? Options: Single beneficiary, Split payments with percentages, Trustee-managed distributions, Other
• Who will be the authorized signers on disbursement accounts and what dual-approval thresholds do you require for transfers? Options: Athlete only, Athlete + financial advisor, Two-authorizer threshold, Custom
• What evidence will validate that financial trust setup is complete (for example, bank confirmation letter, EIN assigned, verified signers)? Options: Bank confirmation letter, Assigned tax ID (EIN/SSN verification), Verified signer list, All of the above
• Describe any escrow or milestone payment requirements from teams or sponsors that must be reflected in trust terms.

Implement Cashflow and Payment Management

• Which recurring payments do you want automated from athlete income (tax withholdings, agent fees, family distributions, savings contributions)? Options: Tax withholdings, Agent fees, Family distributions, Savings contributions, Other
• How frequently should cashflow reports be generated and delivered to you (weekly, monthly, quarterly)? Options: Weekly, Monthly, Quarterly, Custom
• Who will provide the athlete's payroll and 1099/contractor payment records for reconciliation each season? Options: Team payroll, Agency finance team, External accountant, Other
• What payment rails do you authorize for endorsements and guarantees (ACH, wire transfer, escrow provider)? Options: ACH, Wire transfer, Escrow provider, Other
• Specify any cashflow thresholds that trigger alerts or manual review (e.g., incoming payment above $50,000). Options: $10,000, $25,000, $50,000, Custom
• Are there third-party payees (coaches, trainers, legal counsel) who require auto-pay schedules from athlete income? Options: Yes, No

Procure Insurance and Disability Coverage

• What existing insurance policies does the athlete have (disability, career-ending, loss-of-value) including policy numbers?
• Which coverage levels do you need for career-ending injury, short-term disability, and personal liability (dollar amounts)? Options: Standard league minimum, Custom higher coverage, Insurer recommendation needed
• Who is the preferred broker or insurer we should contact for quotes and medical underwriting? Options: Your broker, We can provide broker options, No preference
• When must new coverage be in force relative to contract signing or season start dates? Options: Before signing, By season start, Within 30 days, Custom
• List any pre-existing conditions or prior medical findings that affect underwriting or require disclosure to insurers.
• Are you open to payor-share arrangements where teams sponsor part of disability coverage versus full athlete-paid premiums? Options: Yes, No, Depends on terms

Coordinate Media, PR, and Personal Branding

• Do you have an existing press kit (headshot, biography, season highlights) we should use for opportunities? Options: Yes - provide kit, No - need us to build one
• Which social platforms require managed posting and community response (Instagram, Twitter/X, TikTok, YouTube)? Options: Instagram, Twitter/X, TikTok, YouTube, Other
• Who approves quotes and interview scripts before media appearances (athlete, PR lead, legal counsel)? Options: Athlete, PR lead, Legal counsel, Other
• What crisis protocols must be included for reputation events (injury, legal issue, brand controversy)? Options: 24-hour response team, Prepared holding statements, Escalation to legal, Custom
• Specify desired frequency for proactive media outreach and sponsor-aligned storytelling (monthly, per-campaign, seasonal). Options: Monthly, Per-campaign, Seasonal, As-needed
• Provide any existing brand voice guidelines or sample messaging that must be preserved in public communications.

Manage Brand Licensing and Merchandising Deals

• Which product categories are you willing to license your name or likeness for (apparel, trading cards, video games, collectibles)? Options: Apparel, Trading cards, Video games, Collectibles, Other
• What minimum royalty rate or guaranteed advance do you require for merchandising licenses? Options: Standard market rate, Minimum advance required, Revenue share only, Open to negotiation
• Who must approve final product mockups and packaging (athlete, brand manager, legal)? Options: Athlete, Brand manager, Legal, Other
• Are there manufacturing or distribution channels that are unacceptable (price-point conflicts, overseas manufacturers, certain retailers)? Options: Certain retailers, Overseas manufacturing, Price-point conflicts, None
• Describe any pre-existing licensing deals or merchandising exclusivities that will affect new agreements.
• Would you like us to manage royalty accounting, audit rights, and periodic sales reports from licensees? Options: Yes, No, Partial (audit rights only)

• Representation Agreement (MSA)
• Statement of Work (SOW)
• Fee Schedule & Payment Terms
• Exclusivity & Conflict-of-Interest Addendum
• Onboarding & Milestones Schedule
• Authorization to Act as Agent
• Financial Access & Data Authorization
• Existing Contracts & Endorsements Audit Consent
• Termination & Transition Plan

• Go-live Health Check (Week 1-4)
• First Outcomes Measurement (Week 4-10)
• Acceptance Gate Review (Day ~90)
• Quarterly Career Success Review

• Document any agreed changes to the review cadence or escalation path and publish to the stakeholder list.
• Restate acceptance criteria from Representation Scope
• Produce a documented acceptance decision based on the Representation Scope criteria.
• For any unmet criteria, capture a remediation plan with clear milestones and target resolution dates.
• Ensure the acceptance outcome and supporting evidence are published to the shared channel for auditability.
• Publish the acceptance decision and attach the outcome evidence in the shared channel and project record.
• Open remediation tickets for any failed or conditional criteria with target resolution dates and required evidence for re-evaluation.
• Outcome progress versus Representation Scope targets
• Confirm progress on contract guaranteed value secured and endorsement annualized revenue relative to Representation Scope targets.
• Close or reassign persistent blockers and document updated remediation timelines.
• Validate financial-planning integration progress and list next quarter priorities for activation.
• Update the outcome forecast and endorsement pipeline based on closed deals and near-term prospects.
• Close or re-categorize open issue tickets older than 30 days and publish status updates to the shared channel.
• Re-confirm Representation Scope success criteria and owners
• All onboarding milestones are marked complete or have documented remediation dates.
• Access to financial-planning portals, endorsement trackers, and negotiation calendars is confirmed for named owners.
• If applicable, incumbent representation is confirmed retired or retained read-only with migration tasks logged.
• Publish the onboarding completion summary and outstanding remediation items to the shared channel.
• Open tickets for each blocker with target resolution dates and required artifacts.
• Document incumbent wind-down status and any remaining closeout steps in the shared tracker.
• Present first outcome data versus Representation Scope targets
• Confirm whether contract guaranteed value secured and number of endorsement agreements signed are trending toward the Representation Scope targets.
• Document root causes for any shortfalls and agree specific corrective actions with target dates.
• Agree the exact data package and timeline required for the acceptance gate.
• Publish the outcome dashboard showing contract guaranteed value and endorsement deal counts against Representation Scope targets.
• Create remediation tasks for each root cause with target completion dates and link to the shared tracker.
• Prepare the acceptance gate data package with signed contract extracts and executed endorsement agreements.
• Schedule follow-up checkpoint(s) to validate remediation completion prior to final acceptance closure.
• Financial-planning integration and status
• Onboarding and access validation
• Present outcome evidence for each criterion
• Root cause diagnosis for any gaps
• Agree corrective actions and owners
• Early adoption signals review
• Issue log review and persistent blocker burn-down
• Document pass, conditional pass, or fail per criterion
• Incumbent representation wind-down check
• Agree remediation items and closure timeline for any failed or conditional items
• Confirm timeline to Acceptance Gate
• Feedback collection and shared channel health
• Blockers and immediate remediation actions