Start Here — Who’s in the Room?

• Help us place you: what best describes your firm right now? Options: Independent Registered Investment Advisor (RIA), Broker-dealer / Hybrid, Bank wealth management division, Family office, Other
• Roughly how many licensed advisors and total client household relationships are you supporting today? Options: 1–5 advisors, 6–20 advisors, 21–75 advisors, 76–250 advisors, 250+ advisors
• Who would be the ultimate decision-maker for a platform choice like this? (name or role)
• Who else must sign off before you can pilot or purchase? (select all that apply) Options: Head of Technology/CTO, Compliance Officer, Head of Advice/COO, CFO/Procurement, Advisor pilot group lead, Other
• How soon are you realistically prepared to start a pilot if the right solution is identified? Options: Immediately (0–30 days), 1–3 months, 3–6 months, 6–12 months, Undecided

If Nothing Changes, What Slips Through the Cracks?

• When you step back, what's the single biggest thing your advisors lose time to because systems aren’t connected? Options: Double data entry between systems, Reconciliation and exceptions, Manual client reporting, Custom proposal generation, Other
• Tell us about a recent example where a workflow failure cost time, revenue, or client trust—what happened and who felt the pain?
• How often do mismatched data or integration gaps create compliance or suitability questions for you? Options: Weekly, Monthly, Quarterly, Rarely, Not sure
• Which parts of your current toolstack feel like fragile handoffs rather than reliable systems? (select all that apply) Options: CRM, Financial planning engine, Portfolio accounting / custodian feed, Rebalancing tool, Reporting / client portal, Billing, Document management
• When these friction points occur, what’s the emotional impact on advisors and leadership (e.g., frustration, avoidance, workarounds)?

Who Holds the Keys — Decision, Compliance, and Champions

• Which role currently has the loudest voice in technology purchases—and why do they tend to take the lead? Options: Firm owner / CEO, Head of Technology, Head of Advice / COO, Compliance Officer, CFO / Procurement, Other
• Share one example of how compliance has previously influenced implementation timelines, features, or data handling—what was the non-negotiable?
• Which stakeholders would champion the platform internally, and who is most likely to push back? Please name roles and their primary concerns.
• What evidence or assurances do each of those decision-makers typically need to feel comfortable approving a pilot or purchase? (select all that apply) Options: Custodian connectivity proof, Data migration plan and sample, Compliance approval letter, Advisor adoption plan, Published security certifications (SOC2, ISO), ROI/cost-savings analysis, Other
• How has prior vendor selection gone—smooth and fast, prolonged with stalls, or somewhere in between? What usually causes the stalls? Options: Smooth and fast, Moderate with a few delays, Prolonged with stalls, Never completed

The Migration Mountain — What Would Break the Move?

• What single technical or business constraint would make you abort a migration project?
• Which legacy systems hold the most critical historical data you cannot lose (select all that apply)? Options: CRM (client notes, relationships), Performance history from legacy reporting, Tax lot history, Model portfolios and allocations, Billing and fee schedules, Other
• How clean is your data today on a scale from ‘ready to go’ to ‘needs heavy remediation’? Options: Ready to go, Minor cleanup needed, Significant remediation required, Data integrity unknown
• Walk us through any custodian or clearing relationships that have non-standard connectivity or known issues—who are they and what fails most often?
• What internal windows (e.g., fiscal quarter close, audits, advisor busy seasons) do we need to avoid when scheduling migrations or cutovers? Options: Quarter-end, Tax season, Open enrollment/benefit season, Major product launches, No major constraints, Other

What ‘Good’ Actually Means for Each Person

• If the platform succeeds, what are the top 3 measurable outcomes the firm owner will use to declare victory?
• From the head of technology’s perspective, what technical KPIs would prove the integration is sustainable? (select up to 3) Options: API uptime, Data latency, Error/exception rate, Time to resolve integration issues, Number of manual fixes per month, Other
• What adoption or behavioral signals would make advisors feel the change is ‘worth it’? (pick the most convincing) Options: Less login time across systems, Faster client meeting prep, Automated proposals delivered, Fewer compliance flags, Improved client NPS
• What compliance outcomes would make your compliance officer sign off on a rollout (e.g., audit trail completeness, surveillance capabilities)?
• Which timeline matters most for measuring success after a pilot—30 days, 90 days, 6 months, or 12 months—and why? Options: 30 days, 90 days, 6 months, 12 months, Other

The Advisor Experience — From Login to Client Meeting

• Imagine an advisor’s day: what single repetitive task drains their time most and keeps them from client-facing work? Options: Preparing client reports, Reconciling account data, Building investment proposals, Updating client plans, Billing and admin
• Which advisor workflows must remain uninterrupted during a pilot (select all that apply)? Options: Client meeting prep, Performance reporting, Rebalancing models, Billing run, Client communications
• How do your advisors currently prefer to learn new tools—self-paced, classroom, one-on-one coaching, or shadowing—and how quickly do they typically adopt? Options: Self-paced, Classroom training, 1:1 coaching, Shadowing / peer mentoring, Combination
• Tell us about an advisor who resisted a previous change—what convinced them eventually, or what kept them resistant?
• What advisor-level metrics would signal healthy adoption during a pilot (select up to 3)? Options: Number of client reviews completed in platform, Login frequency, Proposal completion rate, Use of branded client portal, Reduction in admin hours

Pilot That Proves (or Fails) — Designing a Pilot That Matters

• What would a failed pilot look like to you—what signals would make you halt and reassess?
• Which pilot scope gives you confidence—narrow (specific workflows), broad (full advisor experience), or hybrid—and why? Options: Narrow workflow pilot, Full advisor experience pilot, Hybrid phased pilot, Undecided
• What concrete acceptance criteria should the pilot meet to be considered successful? (pick all that apply) Options: Data accuracy within X%, Advisor adoption threshold met, No showstopper compliance issues, Migration completed for pilot accounts, Positive advisor feedback, Other
• Which sample accounts or client segments should be included in the pilot to be representative and low-risk? Options: High-net-worth only, Mass-affluent only, Mixed household types, New clients only, Clients with complex tax lots
• What internal owner(s) will be accountable during the pilot for daily decisions, escalations, and acceptance?

Risk, Compliance & Guardrails — Red Lines We Can’t Cross

• What are the absolute regulatory or policy ‘red lines’ that would prevent platform use under any circumstance?
• Which compliance tools or workflows must be demonstrably available (select all that apply)? Options: Recordkeeping/audit trail, Trade surveillance, Suitability checks, Supervisory workflows and approvals, Data retention policy controls, Other
• How do you currently handle escalations when an advisor’s activity triggers a compliance question, and how fast must a new system support the same process?
• Are there data residency, encryption, or third-party vendor restrictions we need to honor for your firm or clients? Options: Yes—domestic only, Yes—specific vendors restricted, No special restrictions, Unsure
• What ongoing evidence (reports, dashboards, or audits) would you need to receive regularly to keep compliance comfortable? Options: Weekly exception reports, Monthly audit summaries, Real-time alerts, Quarterly governance reviews, Other

Commitment & Next Steps — What Would Make You Say Yes?

• If we demonstrated the integrations, migration plan, and pilot success metrics you just described, what would be the single remaining barrier to a go decision?
• What commercial models are you open to discussing for a pilot and rollout? (select all that apply) Options: Fixed-fee pilot, Per-advisor subscription, Per-account pricing, Usage-based pricing, Hybrid model, Other
• Who should be on a governance cadence post-pilot (roles and meeting frequency) to make go/no-go decisions?
• What would a realistic timeline to firmwide rollout look like if the pilot meets acceptance criteria? Options: Immediate (within 3 months), 3–6 months, 6–12 months, 12+ months, Undecided
• Before we finish, what worries you most about changing platforms that we haven’t covered?

Walk Me Through an Advisor's Day (Start Simple)

• In one short sentence, how would an advisor at your firm describe their typical workday?
• Which tasks regularly consume the most of an advisor's time (select up to three)? Options: Client meetings, Data reconciliation / logging in to custodians, Financial planning and proposal creation, Portfolio rebalancing and trade input, Performance reporting and statements, Administrative billing / billing collection, Compliance and documentation
• What fraction of an advisor's day is spent switching between systems versus interacting with clients? Options: Almost all switching, About half/half, Mostly client-facing, Varies widely by advisor
• Which specific systems does each advisor regularly log into? (select all that apply) Options: CRM (e.g., Salesforce, Redtail), Financial planning (e.g., eMoney, MoneyGuidePro), Portfolio platform (e.g., Orion, Black Diamond), Custodian portal (e.g., Schwab, Fidelity), Performance accounting, Document storage (e.g., SharePoint, Dropbox), Spreadsheets / Local files, Proprietary/internal tools, Other
• Tell me about one recent day where the tools you use directly affected a client outcome—what happened and how did it feel to the advisor?

What If Your Tools Are the Real Bottleneck?

• If your tech stack were intentionally designed to slow advisors down, where would you find the evidence?
• How often do advisors have to manually move data between systems (daily/weekly/monthly)? Options: Multiple times per day, Daily, Weekly, Monthly or less, Rarely
• Which handoffs between systems create the most mistakes or rework? Options: Client profile / household data, Account holdings and positions, Cost basis and lot data, Performance history, Fee/billing data, Trade instructions, Other
• How do you currently detect and resolve integration failures—who owns it and what’s the time-to-resolution?
• On a scale from 1–10, how confident are you in the integrity of the data feeding your advisor-facing tools? Options: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10

Where Data Quietly Breaks Everything

• When data is wrong, which business outcome is most likely to follow (revenue loss, compliance risk, advisor distrust, client churn, etc.)? Options: Client churn / lost relationships, Regulatory/compliance exposure, Advisor distrust in systems, Incorrect billing / revenue leakage, Operational backlog and overtime, Other
• Which custodians and clearing firms feed your systems today? (select all that apply) Options: Schwab, Fidelity, Pershing, TD Ameritrade / Schwab Advisor Services, Envestnet / UMA, Interactive Brokers, Other / multiple, We do not have direct custodian connectivity
• What recurring data mismatches do you see (pick all that apply)? Options: Missing or delayed balances, Stale prices, Incorrect cost basis / lot data, Unexpected account consolidations / duplicates, Broken account identifiers, Partial transaction histories, Other
• How long do mismatches typically persist before being caught and fixed, and who notices them first? Options: Minutes/hours, Same day, Several days, Weeks, We don't have a reliable detection pattern
• Share an example of a data failure that blocked an advisor from doing their job—what downstream work did it create?

Why Adoption Keeps Failing (Even When Tech 'Works')

• If advisors regularly resist new workflows, what's the likely unspoken reason they give up within the first 90 days?
• Which advisor segments are least likely to adopt new systems (select all that apply)? Options: Tenured advisors with large books, Junior advisors / teams, Advisors who bill hourly/percentage, Hybrid advisors with external tools, All are equally resistant
• What incentives or KPIs currently exist to encourage advisor adoption of new tools? Options: Compensation change, Operational support / delegation, Time-savings targets, No formal incentives, Other
• Describe the training and support you’ve offered during prior rollouts—what stuck and what didn’t?
• How do advisors typically voice frustration—through formal channels, private conversations, or quietly switching back to old tools? Options: Formal helpdesk/tickets, Manager escalation, Peer conversations, They quietly revert to old tools, Other

If Migration Were Safe, What Would You Migrate First?

• What’s the riskiest single data element or migration step that could stop a cutover?
• Which data sets are mandatory to migrate for a pilot to be meaningful (select up to four)? Options: Client demographics / KYC, Account holdings & positions, Cost basis / lot history, Account transaction history, Model portfolios & allocations, Billing and fee schedules, Document history / signed forms
• Do you have retention or archival requirements that prevent bulk migrations (e.g., copies of historical reports, signed documents)? Options: Yes - strict archival policies, Some requirements but flexible, No formal retention constraints, Unsure
• If a migration required staged cutovers, what window lengths and blackout periods are acceptable to your advisors and clients? Options: Overnights / weekends, Multi-day windows, Weekend + evening support, We cannot tolerate any blackout, Other
• Where would you place your absolute rollback trigger—what condition would force you to revert to the old system?

Picture a Seamless Advisor Workflow—What Changes?

• Imagine advisors never had to copy/paste or rekey client data—what specific behaviors would that unlock?
• Which measurable signals would prove advisors are adopting the new workflow (select all that apply)? Options: Weekly active users, Proposals created per advisor, Advisor NPS / satisfaction, Time spent in client-facing activities, Reduction in manual reconciliations, Number of client meetings logged
• What minimum uplift in productivity or retention would justify the migration cost in your view (percentages or absolute targets)?
• Who must feel the benefit first for change to spread (select one)? Options: Frontline advisors, Operations team, Firm leadership / owner, Compliance, Clients
• If you could automate one end-to-end advisor scenario tomorrow, which would it be and why?

Hard Compliance and Integration Questions We Can't Skip

• What single compliance requirement would stop a pilot cold if unaddressed (e.g., trade surveillance, record-keeping, signatures)?
• Which compliance controls must be auditable within the platform (select all that apply)? Options: Advisor communications logging, Trade approval workflows, Document access logs, Retention of signed disclosures, Access controls / SSO logs, Other
• Do you have internal IT/security requirements for vendors (SOC2, penetration test, encryption at rest, SSO) that we need to meet before integration? Options: SOC2 + pentest required, SOC2 preferred, Specific encryption / SSO requirements, No formal vendor security checklist, Unsure
• What custodian credentials and technical resources will we need to collect / coordinate for connectivity?
• Describe any previous integration or API projects that failed—what was the root cause?

How Will You Decide This Was Worth It?

• If the project had to earn a net promoter-style score from leadership at 6 months, what would they need to see?
• Which KPIs do you track today that we should use as baseline comparisons (select all that apply)? Options: Revenue per advisor, Assets under management per advisor, Client retention rate, Time-to-onboard new clients, Operational ticket volume, Compliance incident count, Advisor NPS
• Who will be the executive sponsor, the technical owner, and the pilot lead for this program? (name + role for each)
• What cadence and format of updates will convince stakeholders progress is real (weekly dashboard, monthly steering, demo sessions)? Options: Weekly dashboard, Bi-weekly demos, Monthly steering committee, Ad-hoc as issues arise, Other
• What would constitute an acceptable 'go/no-go' condition at pilot completion (specific targets or showstoppers)?

What Small Experiment Would Make You Believe?

• What is the smallest, fastest pilot we could run that would meaningfully reduce your top pain (hours, sample accounts, single advisory team)?
• Which advisors or teams would you nominate for a pilot and why (select all that apply)? Options: A high-volume team open to change, A tenured advisor with influential peers, A junior advisor team that will easily adopt, Operations/implementation team, Compliance / risk as an observer
• What explicit success criteria should we agree for a pilot (select up to four)? Options: % reduction in manual steps, % of accounts successfully migrated, Advisor weekly active usage, Improved time-to-proposal, Zero major compliance exceptions, Positive advisor feedback
• What timeline feels realistic for a pilot from kickoff to results review? Options: 2–4 weeks, 1–2 months, 3 months, Longer than 3 months
• What would make you hesitate to greenlight even a small pilot—what concerns should we address upfront?

Kickoff: What's Driving This Conversation Right Now?

• What's the primary reason you’re exploring a new wealth management platform at this moment? Options: Other, Support growth/scale, Improve advisor productivity, Consolidate multiple tools, Fix custodian/connectivity problems, Meet compliance requirements, Reduce operating cost
• Which one or two outcomes would make this effort clearly worth it to you (be specific—revenue, time saved, retention, risk reduction)?
• Who on your team is most frustrated with the current setup and what does that frustration look like day-to-day?
• If nothing changes in the next 12 months, what do you expect will get harder for the firm? Options: Advisor hiring/retention, Compliance burden, Operational costs, Client experience, Scalability of service, Other

Why Keep Living with Multiple Logins?

• What are you losing today by tolerating disconnected planning, reporting, and portfolio tools? Options: Time (advisor/admin hours), Client experience consistency, Accurate performance reporting, Compliance traceability, Scalability, Other
• Tell me about a recent moment where disconnected systems directly caused a missed opportunity, error, or escalation—what happened and who felt the impact?
• Which daily tasks consume the most advisor time because of tool friction (pick top 3)? Options: Reconciling account data, Preparing proposals, Rebalancing models, Generating client reports, Billing/invoicing, CRM updates, Other
• How do advisors currently hand off work to compliance, ops, or paraplanners, and where does that handoff most often break down?
• How would your firm’s competitive position shift if advisors reclaimed 20% of the admin time they currently spend on manual tasks? Options: Significant advantage, Moderate benefit, Minimal change, Unsure

Where Are Assets, Attention, and Risk Slipping Through?

• Which specific integration or data gap keeps you up at night because it creates operational or compliance risk? Options: Custodian data delays, Incomplete account mappings, Model portfolio misconfigurations, Missing historical P&L, Third-party planning engine mismatch, Other
• Approximately how many advisor- or ops-hours per week are spent manually reconciling or migrating client data today? Options: < 10 hours, 10–25 hours, 26–50 hours, 51–100 hours, > 100 hours, Don't know
• How frequently do data issues trigger a compliance review, exception, or client-facing error? Options: Weekly, Monthly, Quarterly, Rarely, Never
• Which systems must play perfectly together for adoption to be realistic (select all that apply)? Options: Custodian feeds, CRM, Financial planning engine, Portfolio accounting, Reporting engine, Billing system, Single Sign-On/IdP
• Give a concrete example of a historical migration or integration that went well or poorly—what made the difference?

Who Actually Holds the Keys—and What Would Make Them Say Yes?

• If one person could stop this project today, who would it be and what would their top objection likely be?
• Which stakeholders need to be engaged and satisfied before you can run a pilot (choose all that apply)? Options: Firm owner/CEO, Head of Technology/CIO, Head of Compliance, Chief Operating Officer, RIA office manager, Lead advisors, Custodian/clearing rep
• What are the non-negotiable acceptance criteria each of those stakeholders has (list by role)?
• How do procurement, legal, or vendor risk processes typically influence your project timeline? Options: Adds months, Adds weeks, Minimal delay, Depends on vendor, Unsure
• Describe the perfect approval path—who signs, in what order, and what evidence they need to feel comfortable?

If This Project Succeeds, What Will Change About Daily Work?

• How will advisor behavior look different three months after a successful pilot? Options: Less time in admin systems, More client-facing time, More proposals generated, Fewer data reconciliation tasks, Higher client engagement via portal, Other
• What specific adoption metrics will convince you (choose up to three)? Options: % advisors actively using platform, Number of proposals per advisor, Reduction in advisor admin hours, Client portal adoption rate, Number of reconciled accounts, Compliance exception rate drop
• What adoption threshold would you set for pilot success (pick one)? Options: > 80% active usage by pilot advisors, 60–80%, 40–59%, < 40%, Unsure
• Which advisor segments are most critical to convert for firm success—describe their characteristics and why they matter.
• How would you measure client impact from advisor adoption (select all that apply)? Options: Retention/attrition, Net new assets, Client satisfaction/CSAT, Time to proposal, Cross-sell rate, Other

Designing a Pilot That Leaves No Excuses

• What must happen in the pilot for you to confidently say 'scale it'—what are the 2–3 non-negotiables?
• What’s the ideal pilot size and composition for your firm? Options: Small core team (3–5 advisors), Representative mix (10–20 advisors), Large cohort (20+ advisors), Ops-only pilot, Compliance-only validation, Unsure
• How long should the pilot run to demonstrate true outcomes (pick one)? Options: 4 weeks, 8–12 weeks, 3–6 months, 6+ months, Depends on scope
• Who will own pilot success day-to-day and who is the escalation point for blockers?
• What pilot acceptance tests are absolute must-passes (select all that apply)? Options: Accurate custodian account mapping, Report parity with legacy, Advisor workflow end-to-end, No critical compliance exceptions, Data migration integrity, SSO and access controls
• What internal resources are you willing to commit during the pilot (time per week, named roles)?

Compliance, Security, and Custodian Red Lines

• When compliance reviews vendors, what single issue has caused the most rejections historically? Options: Data residency concerns, Insufficient audit logs, Weak access controls, Lack of encryption at rest, Custodian integration risk, Other
• Which security or compliance artifacts will you require before pilot kickoff (select all that apply)? Options: SOC2 report, Pen test summary, Data processing agreement, Encryption and key mgmt details, Custodian attestation, Third-party risk questionnaire
• Are there regulatory workflows we must support out of the box (e.g., suitability recording, branched supervision, audit trails)? If yes, list them.
• What custodian(s) and clearing firms must be validated during the pilot (select all that apply and add specifics if needed)? Options: Charles Schwab, Fidelity Institutional, Pershing, TD Ameritrade/Schwab Integration, Other custodians, Multiple custodians—details in notes
• What are your minimum expectations for data migration safety and rollback capability during pilot? Options: Full rollback capability, Incremental reversible imports, Read-only migration first, No rollback required, Unsure—need guidance

Decision Roadmap: Money, Timing, and the Unsaid Risks

• If this project misses your target window, what happens to firm priorities or risk exposure?
• What's the budget range you’re prepared to commit for a successful pilot and initial rollout? Options: Under $25k, $25k–$75k, $75k–$200k, $200k–$500k, 500k+, Undecided
• What procurement or contracting steps typically take the most time in your organization? Options: Legal review, Security/IT approval, Budget sign-off, Vendor risk assessment, Executive approval
• What would be a realistic go/no-go decision date for the pilot based on your internal calendar? Options: Within 30 days, 30–60 days, 2–3 months, 3–6 months, TBD
• Who needs to be present for a final decision meeting, and what evidence will each person require to sign off?
• What unresolved doubts or hidden risks would make you delay a decision even if pilot metrics look promising?

Next Steps: What Would Make This Feel Manageable?

• What’s one small, low-risk step you’d like to try first to build momentum? Options: Proof-of-concept with 1 advisor, Read-only custodian feed validation, Sample report comparison, Joint workshop with compliance, Other
• What support style would give you the most confidence from a vendor during pilot (pick up to two)? Options: Hands-on implementation team, Dedicated customer success manager, Self-service docs + periodic check-ins, Train-the-trainer model, Embedded ops support
• How would you like us to present a proposed pilot plan—high level timeline, a detailed RACI, or a compliance-first checklist? Options: High level timeline, Detailed RACI, Compliance checklist, All three
• Who else should we include in the next meeting to ensure progress (names and roles)?
• Finally, what would make you feel excited—rather than merely comfortable—about moving forward with a pilot?

Getting to Know Your Firm’s Day-to-Day

• How many advisors will be directly affected by this platform in the first 12 months? Options: 1-5, 6-20, 21-50, 51-150, 151+
• How would you describe your firm’s current client segment focus? Options: High-net-worth / UHNW, Mass affluent, Retail wealth, Institutional / Advisor of advisors, Mixed
• Walk me through a typical advisor workflow today — from client intake to reporting. Where do you see the most handoffs or tool-switching?
• Which systems do advisors currently log into most often (select all that apply)? Options: Traditional CRM (Salesforce, Redtail), Financial planning engine (e.g., eMoney, MoneyGuide), Portfolio management / OMS, Reporting tool, Custodian portal, Other
• When you think about daily advisor time spent on admin vs. client-facing work, what proportion feels accurate? Options: >70% admin, 50–70% admin, 30–50% admin, <30% admin, Not sure
• Tell us about one recent client interaction where the current toolset either helped win the meeting or made it harder — what happened?

Why Do You Keep Wrestling with Multiple Tools?

• What is the single biggest cost—financial, operational, or emotional—you accept by keeping fragmented systems? Options: Time/efficiency loss, Compliance risk, Client experience inconsistency, Migration cost fear, Advisor resistance, Other
• How often do tool-related problems (broken integrations, stale data, duplicate entries) materially delay client work? Options: Weekly, Monthly, Quarterly, Rarely, Never
• When integration or data problems occur, who on the team ends up owning the firefight and how does that feel for them?
• Give an example of a recent project or migration attempt that stalled — what were the root reasons and what was the emotional impact on leadership?
• Which of these would you say hurts your ability to win new clients the most? Options: Slow onboarding, Inconsistent proposals, Limited reporting sophistication, Lack of branded client portal, Operational errors
• How long has your firm tolerated these frictions? Has any specific event accelerated interest in change? Options: <6 months, 6–12 months, 1–2 years, 2+ years, No specific event

Who Really Calls the Shots (and What Do They Value)?

• Who are the decision-makers we need to convince for a pilot and final rollout, and what outcome does each person care about most?
• Which stakeholder group do you expect to be the hardest to convince and why? Options: Firm owner/CEO, Head of Technology, Head of Compliance, CFO/Operations, Lead Advisors, Other
• For each of these roles, what does a successful pilot look like to them (e.g., ROI, regulatory proof, advisor satisfaction)?
• What is your desired decision timeline from pilot to rollout, and are there fixed windows we must respect (e.g., fiscal calendar, busy seasons)? Options: Immediate (1-3 months), Near term (3-6 months), 6-12 months, 12+ months, Tied to fiscal/seasonal window
• Who will be the single point of contact for implementation decisions, and who will own internal change management and communications?
• Are there any internal politics, previous vendor failures, or personal stakes we should be aware of to design the pilot for success?

Where Data Goes to Die (and Why We Should Care)

• How confident are you in the accuracy and completeness of custodian account data arriving in your systems today? Options: Very confident, Mostly confident, Somewhat confident, Not confident, Unknown
• List the custodians and clearing firms you currently work with, and note any you anticipate adding in the next 12 months.
• Which of these integration problems have you seen in the wild (select all that apply)? Options: Missing positions, Out-of-sync balances, Broken authentication / credential expirations, Slow API performance, Mapping mismatches (account IDs, asset classes), None of the above
• Describe your last data migration experience — what took longest, what surprised you, and who was most impacted?
• How do you currently detect and remediate data issues? Is this process automated, manual, or hybrid? Options: Automated monitoring, Manual reconciliation, Hybrid, Ad hoc / reactive
• If we had to prioritize integrations for a pilot, which are must-have vs nice-to-have (custodians, reporting, planning engine, CRM)? Options: Must-have, Nice-to-have, Not needed

What Would Advisor Adoption Actually Look Like?

• If advisors were truly excited about this platform, what behaviors would you see three months into a pilot?
• What adoption threshold would make you comfortable moving from pilot to broader rollout (e.g., % of pilot advisors hitting usage metrics)? Options: >90%, 75–90%, 50–75%, <50%, Not sure
• Which incentives or support have historically moved advisor behavior here — time-savings, compensation, compliance simplicity, or something else? Options: Time-savings, Comp incentives, Compliance ease, Dedicated support/training, Peer champions, Other
• Who on your team would be the most credible internal champion for advisors, and how do advisors respond to them today?
• What training cadence and formats do advisors prefer — hands-on workshops, on-demand videos, peer mentoring, or shadowing during real client meetings? Options: Hands-on workshops, On-demand videos, Peer mentoring, Shadowing sessions, Documentation only, Other
• Describe any advisor cohorts (by AUM, tenure, or tech-savviness) that should be included or excluded from the pilot and why.

If Success Were Visible in a Dashboard

• Which three business metrics would prove this platform is delivering value to your firm? Options: Net new AUM, Advisor productivity (meetings/client hours), Client retention, Time to onboard a client, Operational error reduction, Fee revenue per client
• What baseline numbers do we need to capture now so we can measure pilot impact (please list known values where possible)?
• How quickly do you expect to see measurable change after a successful pilot (choose the timeframe you’d find convincing)? Options: 30 days, 3 months, 6 months, 12 months, Depends on metric
• What financial or qualitative ROI would make leadership say ‘we should invest to scale this’?
• Are there regulatory or audit metrics that must be captured alongside business KPIs for your compliance team to sign off? Options: Activity logging, Suitability history, Document retention, Access controls, All of the above, Other
• Who will own ongoing measurement and reporting during and after the pilot (title/function)?

What Could Make This Rollout Fail (So We Avoid It)?

• If you had to name one scenario today that would make you halt deployment, what would it be?
• What compliance or governance requirements are absolute deal-breakers unless satisfied during pilot (e.g., recordkeeping, encrypted messaging, approval workflows)?
• What rollback or remediation triggers do you want documented up front (examples: data discrepancies >X%, advisor adoption <Y%, security incident)?
• Who gets the final go/no-go authority on the pilot acceptance criteria and escalation paths if issues arise?
• How would you like us to run simulated failure drills (frequency and scope) before the pilot cutover? Options: Full dry-run with sample clients, Targeted scenario tests, API & credential failure tests, Compliance audit simulation, No drills requested
• What budget contingency or timeline buffer are you willing to accept to manage unexpected blockers? Options: None, 1-2 weeks, 1 month, 1-3 months, Flexible as needed

Ready to Commit to a Pilot That Feels Safe?

• Which pilot scope feels realistic and high-impact to you: small technical validation, advisor-facing pilot, or full end-to-end production trial? Options: Technical validation only, Advisor-facing pilot (subset of clients), End-to-end production trial (full workflows), Phased approach
• What are the non-negotiable acceptance criteria we should include in the pilot agreement (list specific metrics or conditions)?
• Who do we need in the kickoff workshop from your side (roles and availability)?
• What would make you say ‘this pilot exceeded expectations’ when we finish — describe the headline result you’d want to share internally.
• How would you prefer we communicate progress during the pilot (weekly email, executive summary, real-time dashboard, etc.)? Options: Weekly email, Biweekly executive summary, Real-time dashboard, Ad hoc meetings, Combination
• On a scale from 1–10, how ready is your firm to begin a pilot now, and what would move that number two points higher? Options: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10