ROBS Professional-Advisor Question Generator

Start with lifecycle stage, topic concerns, existing team roles, and meeting objective. Unknown is acceptable; it creates foundational questions instead of pretending the facts are settled. Bring the output to the meeting and ask each professional to identify written assumptions, responsible owner, evidence needed, fee/scope boundary, and follow-up owner.

The generator deliberately asks “what facts support,” “who owns,” “what written evidence,” “what assumptions,” and “which professional decides.” It does not ask advisers to promise audit-proof, IRS-approved, guaranteed, tax-free, or risk-free results.

ROBS issues often cross legal, tax, qualified-plan administration, employer-stock valuation, custody, payroll, corporate, lender, and insurance boundaries. DOL fiduciary guidance identifies discretionary authority over plan management, assets, administration, and compensated investment advice as fiduciary functions, while IRS ROBS materials flag separate plan status, participant, rollover, stock valuation, business, Form 5500, and Form 1120 records [1] [5].

Credentials, directories, licenses, or titles can help identify a starting point, but they do not guarantee competence or create privilege automatically. Ask for the engagement letter, scope exclusions, conflict disclosures, fee basis, secure communication process, and when another professional must be involved [6].

• Initial setup: select considering, eligibility, funding, plan design, employer stock valuation, and initial screening.
• Operating with payroll error: select setup-operating, payroll/contributions, employee participation, audit/correction, employees yes, prior error yes, and problem escalation.
• Related-party transaction: select fiduciary/conflict, prohibited transaction, valuation, related-party yes, and second opinion.
• Audit notice: select audit/correction, reporting, records, time-sensitive notice yes, prior notice yes, and problem escalation.
• Business sale or exit: select business sale, closure, plan termination, distribution/tax, employer stock yes or unknown, and handoff.

• Anyone promises audit-proof, IRS-approved, tax-free, guaranteed, or risk-free treatment without written assumptions and source basis.
• Fee, affiliate, referral, compensation, security, or conflict terms are unclear.
• An adviser opines outside the written scope of engagement or refuses to identify who owns another lane.
• No one will provide written assumptions, evidence requests, responsibility matrix, or handoff instructions.
• Sensitive plan, tax, participant, payroll, or account information is requested through an insecure channel.

The tool runs in your browser and uses only selected fields. It does not collect freeform sensitive narrative, names, firm names, prices, account numbers, EINs, SSNs, balances, uploads, documents, clipboard data, email, print, or downloads. It does not set tool-local cookies or save generated status after you leave the page.

Question status markers are only on-page meeting aids. Counts show questions, roles, and high-priority questions; they are not risk scores, adviser rankings, pass/fail results, or endorsements.

1. IRS ROBS compliance project — checked Aug. 14, 2026.
2. IRS retirement plan assets and valuation — checked Aug. 14, 2026.
3. IRS EPCRS overview — checked Aug. 14, 2026.
4. IRS Form 5500 corner — checked Aug. 14, 2026.
5. DOL fiduciary responsibilities — checked Aug. 14, 2026.
6. IRS choosing a tax professional — checked Aug. 14, 2026.