Before the offer: a tax and payroll scorecard for a senior household or office hire

A family deciding between candidates for a senior financial role, such as a household chief financial officer, controller, or office lead, will usually score them on competence, fit, and integrity. That evaluation belongs to the family and its advisors. But there is a second scorecard worth running before an offer goes out: a tax and payroll checklist for the role itself. Senior hires often handle the household's tax records, payments, and IRS correspondence. The terms of the job decide who files what, who can sign, and who is responsible if a payroll deposit is missed.

This post is a pre-offer tax and payroll checklist for a senior household or office hire, and a short list of tax-related questions a family can ask any candidate about how they handle tax records. It does not evaluate candidates, it is not hiring or employment law advice, and it does not recommend any person or firm.

Part one: the role checklist

Score each item before the offer. The answers go to your preparer and payroll provider.

Employer and classification

• Which entity employs the person, and does that entity have an EIN and payroll accounts?
• Is the role clearly an employee role under the common-law control test? A full-time senior role that reports to the family is generally employment, not a 1099 engagement.
• In which state will the person work, including remote days? Each work state may need withholding and unemployment registration.

Pay structure

• Base salary and the entity that pays it.
• Bonus terms in writing, with payment timing. A bonus paid within two and a half months after year end is generally a short-term deferral.
• Any deferred pay, retention payments, or incentive tied to investment results, flagged for counsel review under IRC Section 409A.
• Any profits interest or equity, flagged for tax counsel.

Authority

• Will the person sign tax returns for any entity? Only an officer, partner, trustee, or other authorized person can sign an entity return. The role's title and the entity documents should match.
• Will the person authorize tax payments? Anyone with authority over payroll tax deposits can be a responsible person for the trust fund recovery penalty under IRC Section 6672.
• Will the person need a Form 8821 to receive IRS information, or a Form 2848 to represent the household? A Form 2848 can only name eligible representatives such as attorneys, CPAs, and Enrolled Agents for full representation. A non-credentialed employee generally needs an 8821.
• Will the person access IRS and state online accounts? Each person should use their own credentials where the system allows, rather than a family member's login.

Data and records

• How will the person receive and send tax documents? An encrypted channel is consistent with the safeguards in IRS Publication 4557.
• Where will records be kept, and what happens to access when the person leaves?
• Will the preparer share return information with this person? That requires written consent under IRC Section 7216.

The role scorecard

Score each item 0, 1, or 2. Zero means missing. One means partial or out of date. Two means current and documented.

Item	0, 1, or 2
Employing entity, EIN, and payroll accounts in place
Classification as employee documented
Work states identified and registered
Bonus timing written and within short-term deferral where intended
Deferred or incentive pay reviewed by counsel
Signing authority matches entity documents
Payment authority and responsible person named
Forms 8821 or 2848 planned for the right people
Section 7216 consent for preparer information sharing
Secure document channel and offboarding plan written

A total of 16 to 20 means the role is ready. A total of 10 to 15 means finish the setup before the start date. Below 10, the tax side of the job is not defined yet.

Part two: tax questions to ask any candidate

These questions do not test tax knowledge. They test whether the candidate's habits will keep the household's records sound. A family can ask them alongside its own interview questions.

1. How do you track K-1s and 1099s each year? A good answer names a tracker with expected dates and a follow-up routine.
2. How do you handle a tax notice? A good answer includes logging it, sending it to the preparer the same week, and tracking the response deadline (often 30 or 60 days).
3. How do you send documents to a preparer? A good answer names an encrypted method, not plain email.
4. How do you make sure estimated payments are made on time and applied to the right year? A good answer includes saving confirmations and checking the IRS account after posting.
5. What do you do when you are asked to pay a personal expense from a business account? A good answer is that they record it correctly or decline, and tell the preparer.
6. How do you verify a payment request that arrives by email? A good answer includes calling back on a known number. Payment fraud often targets the person who moves money.
7. What records would you hand to your successor? A good answer is a written list, not "it's all in my head."

A candidate's credentials, references, and fit are the family's judgment. The answers to these questions show how the tax records will be kept under that person.

Families sometimes worry that asking these questions signals distrust. It is closer to the opposite. A strong candidate for a role that touches tax records expects to be asked how they handle notices, payments, and documents, and usually has a clear answer. Vague answers to these seven questions are worth noting alongside whatever the family learns from references.

The questions also work for existing staff. Asking a long-serving employee the same seven questions once a year shows where habits have drifted, especially on document security and payment verification.

Background checks and tax records

Some families ask candidates about their own tax compliance. Employment law limits what can be asked and how, which varies by state. That is a question for employment counsel. A related point is within the tax world: if a candidate will represent the household before the IRS as a credentialed professional, their status can be checked. Enrolled Agents, CPAs, and attorneys have public licensing or enrollment records, and the IRS maintains a public directory of federal tax return preparers with credentials.

Illustrative: authority without a title

Illustrative: A household hires a senior administrator who will run payroll for two household employees and pay estimated taxes for the parents and a trust. The offer letter gives her the title "Director of Finance" but no role in any entity. She is given the parents' IRS online login.

The preparer's concerns: she cannot sign the trust's return because she is not a trustee, she is using someone else's IRS credentials, and she will control payroll deposits, which makes her a possible responsible person if deposits are missed. The fixes are a Form 8821 for her, her own payroll provider access, a clear written statement of who is the employer for the household staff (the parents, on Schedule H), and a documented approval process for payments.

Part three: the first 90 days

A new senior hire's first months are when tax handoffs either happen cleanly or get lost. Set three checkpoints with the preparer:

1. Week two: the new hire receives the filing map, the entity list, the K-1 tracker, the carryforward list, and the payroll calendar from whoever held them before. Gaps are written down, not assumed away.
2. Day 45: the new hire confirms that every payroll deposit since their start date has posted in EFTPS, that each estimated payment made for the household was applied to the right tax year, and that any open IRS or state notices have been sent to the preparer.
3. Day 90: the new hire and the preparer review the year-end plan together: fourth quarter estimates (due January 15, 2027 for the 2026 year), Form 1099 and W-2 preparation for January, the expected K-1 list, and any gifts that will need a Form 709.

These checkpoints are not a performance review. They are how the household confirms that tax responsibilities transferred with the job. A hire who starts in September and has no checkpoint before January often learns about the year-end filing calendar from the first notice.

Who owns what

The family and its advisors evaluate candidates. Employment counsel drafts the offer. The preparer and payroll provider check the role setup against the scorecard.

Next step: fill out the role scorecard for the open position and send it to your preparer before the first interview, not after the offer.

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Educational only. This is not tax or legal advice for your situation. Consult your own CPA, EA, or attorney before acting.