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The Opinionated Daily of Technology & Code
GARRY'S TAKE
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| Tuesday, March 3, 2026 · Playbook |
PLAYBOOK |
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STEP-BY-STEP GUIDE
The Nanny Interview Playbook
A research-backed guide to hiring household childcare in San Francisco, from first interview to signed contract.
By Garry Sandcastle
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1
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Prepare Behavioral and Situational Questions
Focus on past behavior as a predictor of future behavior. Ask about discipline scenarios they've actually handled, communication cadence with parents (daily logs, photos, notes), and conflict resolution. For situational questions: choking response, public tantrums, differing rules vs. nanny beliefs. Ask for step-by-step plans, not vague answers.
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2
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Screen for Red Flags During the Interview
Watch for: late arrival or taking calls during the interview, thin or unverifiable references, resistance to background checks (especially TrustLine in California), negative talk about prior families, and pushing for under-the-table pay. The biggest red flag? Poor engagement with the child during the meeting.
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3
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Run a Structured Trial Day
Set clear expectations and a written routine in advance. Be present the first 30-60 minutes, then leave the home for a block to assess independence. Observe warmth, initiative, safety instincts, and calm under stress. Pay fairly for trial hours. Debrief at end and solicit open-ended feedback from the child.
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4
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Complete Background Checks
In California, TrustLine is the gold standard -- state-authorized fingerprint check accessing CA DOJ, FBI criminal databases, and the CA Child Abuse Central Index. Supplement with a national FCRA-compliant screening (Checkr, GoodHire, or Sterling). Include: identity/SSN trace, multi-jurisdiction criminal, sex-offender registry, and MVR if driving.
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5
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Understand Legal Requirements
California Domestic Worker Bill of Rights: overtime at 1.5x over 9 hrs/day or 45 hrs/week. Workers' comp is mandatory. Federal: obtain EIN, issue W-2, file Schedule H. CA EDD household employer registration when wages hit $750/quarter. SF paid sick leave: accrual 1 hr per 30 hrs worked, cap 40-72 hrs. SF minimum wage: $19.18 as of July 2025.
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CHECKLIST
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| ☐ Prepare written interview questions (behavioral + situational) | | ☐ Verify CPR/First Aid certification is current | | ☐ Request and call 3+ phone references (not just letters) | | ☐ Run TrustLine background check (CA-specific) | | ☐ Run national criminal + sex offender screening | | ☐ Check MVR if nanny will drive with child | | ☐ Draft written work agreement with scope, hours, pay, PTO | | ☐ Set up payroll (Poppins Payroll, HomeWork Solutions, or GTM) | | ☐ Obtain workers' comp coverage (homeowner's policy endorsement) | | ☐ Schedule and pay for a trial day |
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WATCH OUT |
PITFALL
Skipping TrustLine Because "They Seem Nice"
TrustLine accesses databases that standard commercial background checks cannot -- including the CA Child Abuse Central Index. It is not optional for California families hiring in-home childcare.
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PITFALL
Paying Under the Table
Besides being illegal, it exposes you to back taxes, penalties, and loss of dependent care FSA benefits. It also leaves your nanny without unemployment insurance, workers' comp, or Social Security credits.
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PITFALL
Vague "Light Housekeeping" Expectations
Define concretely what housekeeping means: child's laundry only? Kitchen cleanup after meals? Time-box it. Ambiguity here is the top source of nanny-family friction.
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