A Miami family we know interviewed a candidate who seemed perfect on paper. Great references, solid experience, warm personality with their kids during the trial. They hired her. Three weeks in, they discovered through a casual conversation that she’d been fired from her previous position for repeated lateness and unreliability, not that she’d “decided to pursue other opportunities” as she’d claimed. The family was furious. If they’d known, they never would have hired her. But they’d never asked directly why she left her last job. They’d accepted her vague explanation because pressing for details felt uncomfortable and potentially rude. That discomfort cost them three weeks of settling in with someone who ended up repeating the same patterns that got her fired before, leaving them right back in recruiting mode with disrupted childcare.
Every experienced placement coordinator has dozens of stories like this. Families who skipped questions they needed to ask because the questions felt awkward, intrusive, or potentially discriminatory. Then they discovered information after hiring that they absolutely should have known beforehand. The questions families avoid often reveal the most important information about whether a candidate is truly appropriate for the position. Asking hard questions isn’t rude if done professionally, it’s responsible hiring. We’ve been placing nannies in Miami and across major markets for over twenty years, and we’ve learned that the families who ask thorough, sometimes uncomfortable questions during interviews make better hiring decisions than families who stick to only the comfortable surface-level discussions. Let’s talk about the questions families are afraid to ask, why those questions actually matter, how to ask them professionally, and what the answers tell you about candidates.
Why You Specifically Left Your Last Position
This is the big one families dance around constantly. Candidates offer sanitized explanations, families accept them at face value, and everyone avoids the awkward follow-up questions that would reveal the real story. You need to know specifically why someone left their last position, especially if they had a long tenure and then suddenly it ended. “The family no longer needed me” could mean the children aged out of needing a nanny, or it could mean they let her go and she’s framing it as mutual. “I wanted new opportunities” could mean she’s ambitious and ready for new challenges, or it could mean she was about to be fired and left before that happened. “It was time for a change” tells you absolutely nothing.
Ask directly: “Can you tell me specifically what led to you leaving your last position?” If the answer is vague, follow up. “You mentioned the family no longer needed you. Can you elaborate on what changed?” If she says they let her go, ask why. “What did they tell you when they ended the employment?” Most candidates are honest if asked directly. The ones who keep dancing around the question with vague non-answers are often hiding something. Cross-reference her explanation with what references say. If she claims she left for better opportunities but the reference says they let her go for performance issues, you’ve caught a significant lie that should end her candidacy immediately.
Don’t assume you can’t ask about termination. You absolutely can. How and why previous employment ended is directly relevant to hiring decisions. What you’re listening for: Consistent story across multiple telling. If her explanation changes, that’s a red flag. Specific details rather than generalities. Real explanations include specifics. Vague stories are often covering problems. Willingness to be honest about mistakes or difficulties. The candidate who can say “I struggled with their schedule expectations and we mutually agreed I should find a better fit” is being more honest and more self-aware than the one who insists every past position was perfect until she decided to leave.
Gaps in Your Employment History
Most candidates have gaps. That’s normal. What’s not normal is being evasive about what happened during those gaps. “I took time off” for six months could mean anything from recovering from health issues to dealing with a family crisis to being unable to find work after termination. You’re entitled to understand employment gaps, especially recent ones or patterns of gaps. Ask clearly: “I notice you had a gap from March 2023 to September 2023. Can you tell me what you were doing during that time?” If the answer is personal and legitimate, most candidates will tell you. Health issues, family caregiving, maternity leave, relocation, education, these are all reasonable explanations that candidates typically share if asked respectfully.
If she’s vague or uncomfortable, that might indicate she was unemployed because she was fired and couldn’t find new work quickly, or she had personal problems that affected her employability, or something else she’s not comfortable disclosing. You get to decide how much detail you need, but persistent vagueness about gaps is usually concerning. Watch for patterns. One gap? Could be anything. Multiple gaps in similar patterns? That’s data. If someone has repeatedly worked for families for 8-12 months and then has 3-4 month gaps afterward, she’s either leaving positions frequently or being let go frequently. Either way, that pattern should concern you.
Be reasonable about what you’re asking. “What were you doing between jobs?” is fair. “Can you account for every single month of the past decade?” is excessive. Focus on recent history and significant gaps, not minor timing overlaps between positions. Remember some candidates, especially those new to professional childcare, might have been in other careers or in school during gaps. That’s fine. What matters is understanding the gap, not punishing people for having them.
Have You Ever Been Terminated from a Nanny Position
This question terrifies families because it feels accusatory and because they worry about legal implications of asking about past employment. It’s actually a completely legal and appropriate question. You can ask if someone has been fired from previous positions. What you can’t do is discriminate based on protected characteristics, but termination history isn’t a protected characteristic. The question matters because patterns of termination suggest someone who struggles in household employment for reasons that will likely repeat. One termination? Could be bad fit, unreasonable family, or legitimate mistake the candidate learned from. Multiple terminations? That’s a pattern indicating the problem is probably with the candidate.
Ask directly: “Have you ever been let go or terminated from a nanny position?” Give her opportunity to explain context. “It happened once. The family and I had very different ideas about discipline and after trying to make it work for several months, they decided to find someone whose approach aligned better with theirs.” That’s an honest, specific, reasonable explanation that shows self-awareness. Compare that to “No, I’ve never been fired, all my positions ended because I chose to leave or the family moved.” Then you check references and discover she was actually fired from her last two positions. That lie should end her candidacy immediately.
Some candidates will try to reframe terminations as mutual decisions or claim they quit right before being fired. Push gently for clarity. “It sounds like it wasn’t working for either party. Who initiated the conversation about ending employment?” The truth usually comes out if you ask follow-up questions. What you’re assessing: Whether she can be honest about difficult experiences. Whether she takes responsibility or blames everyone else. Whether she’s learned from past situations or is likely to repeat them. A candidate who can discuss termination honestly, explain what happened, and articulate what she learned from it is often safer to hire than one who insists she’s never had any employment problems ever.
Your Financial Situation and Reliability
This is the question families fear most because it feels invasive and potentially discriminatory. But financial stress directly impacts employment reliability, and you need to know if the candidate is in a financial situation that will create problems. You can’t ask about credit score, bankruptcy, or specific debt amounts. You can ask about financial stability in ways that relate to job reliability. What you’re really trying to assess: Can she afford to take this position at the offered compensation? Is she desperate for any income and likely to leave the moment something paying better appears? Does she have reliable transportation? Does she have stable housing?
Frame it professionally: “This position pays $X annually. Will that compensation meet your financial needs and allow you to maintain stable employment with us long-term?” You’re not asking for financial details, you’re asking if the job meets her needs. If she hesitates, probe gently. “I want to make sure this position makes sense for you financially. Is the compensation in line with what you need?” Watch for red flags: Accepting significantly below-market rates because she’s desperate. Likely to leave quickly for better pay. Multiple questions about when she’ll be paid or whether payment is guaranteed. Might indicate financial crisis affecting reliability. Vagueness about current housing situation or mentions of housing instability. Could affect her ability to get to work reliably. Requests for advances or early payment before even starting. Serious financial stress that will affect employment.
What’s reasonable to know: Whether she has reliable transportation to get to your home. Whether the compensation allows her to support herself sustainably. Whether financial stress is likely to affect her ability to work reliably. What’s not your business: Specific debt amounts, credit problems, family financial details. Keep questions focused on job-relevant financial stability.
Childcare Philosophy That Might Clash With Yours
Many families don’t directly ask about discipline approaches, screen time views, feeding philosophies, or other areas where misalignment creates daily conflict. They assume they’ll communicate their preferences and the nanny will follow them. Sometimes that works. Often it doesn’t, because deeply held beliefs don’t disappear just because an employer disagrees. If your nanny genuinely believes spanking is appropriate discipline and you absolutely oppose physical punishment, that fundamental disagreement will create tension even if she agrees not to spank your children. Her underlying belief will affect how she views your parenting and how she relates to discipline situations.
Ask specifically about areas that matter to you: “How do you typically handle discipline when children are behaving inappropriately?” Listen for alignment with your approach. “What’s your view on screen time for young children?” See if her philosophy matches yours. “How do you approach feeding, especially with picky eaters?” Understand whether she’ll follow your guidance or push her own beliefs. You’re not looking for perfect alignment on every parenting opinion. You’re looking for fundamental compatibility on issues that affect daily childcare and willingness to work within your framework even when her personal views differ.
Red flags: Strong opinions delivered with certainty that don’t match your approach. Judgment about alternative viewpoints. Unwillingness to consider different methods. Watch her face and tone when you describe your approaches. If you explain your gentle discipline philosophy and she looks skeptical or dismissive, she’s unlikely to embrace it genuinely even if she verbally agrees to follow it.
Criminal History and Background
This is legally complex and varies by state, but in general you can ask about criminal history for positions involving childcare. Many states allow or encourage background checks for household employees working with children. How to approach this: “We conduct background checks on all finalists for this position. Is there anything in your history that would appear on a background check that you’d like to discuss?” This gives her opportunity to disclose and explain rather than you discovering through the background check.
Some offenses are absolute disqualifications for childcare positions. Anything involving children, violence, theft, or substance abuse should end candidacy. Some offenses might be old enough or minor enough to not be disqualifying depending on context and how the candidate has addressed them. What matters is honesty, not perfection. A candidate with a minor offense from a decade ago who discloses it and explains what happened is often safer to hire than a candidate who claims a perfect record but you discover had undisclosed issues. The dishonesty is the disqualifying factor.
Understand the legal limits in your jurisdiction. Some states restrict when you can ask about criminal history or what types of convictions can be considered. Consult with an employment attorney if you’re unsure about your rights and limitations. Never skip background checks for childcare positions just because you feel awkward about them. Your children’s safety is more important than avoiding uncomfortable conversations. Professional agencies conduct these automatically. If you’re hiring independently, use reputable background check services.
References Who Might Not Give Glowing Recommendations
Candidates provide references they think will speak well of them. But sometimes they’re forced to include references they know might be less than stellar, usually their most recent employer who they left on less-than-great terms. Pay attention to which references she offers and which she avoids. “I’d like to speak with your three most recent employers. Can you provide contact information for them?” If she readily provides all three, good. If she tries to skip one, dig into why. “I notice you didn’t include the family from 2022-2023. May I ask why?”
Legitimate reasons for not providing a reference: The family is deceased or unreachable. Privacy concerns if the family is high-profile and unreachable through normal means. Ended truly mutually with no hard feelings but they’ve moved internationally and are difficult to contact. Less legitimate reasons: “We didn’t part on good terms.” Then you definitely need to talk to them. “I don’t think they’ll say nice things about me.” All the more reason to hear their perspective. “They were crazy and unreasonable.” Might be true, might be her explaining away termination.
Push back when references seem incomplete: “I understand the relationship didn’t end perfectly, but I need to hear from recent employers to make an informed decision. Can you provide their contact information?” If she absolutely refuses, that’s information. She’s hiding something significant enough that she won’t let you talk to people who directly observed her work. For positions involving children, thoroughness on references matters more than avoiding awkwardness. Insist on speaking to recent, relevant references even if the candidate is uncomfortable. Her discomfort is less important than your children’s safety and your family’s needs.
How to Ask Hard Questions Professionally
Frame questions neutrally without accusation. “Can you walk me through exactly what happened?” feels different from “Why were you fired?” even though you’re getting at the same information. Explain why you’re asking. “I ask all candidates about gaps in employment to understand their full work history” feels less targeted than just demanding explanation. Give context that you ask everyone the same questions so it doesn’t feel personally attacking. Stay calm and matter-of-fact. These are business questions about employment, not personal attacks. Professional tone makes them less uncomfortable.
Listen more than you talk. Ask the question, then be quiet and let her answer fully. Don’t jump in with follow-ups until she’s finished. Take notes during the interview so you can review answers later and check for consistency. Follow up on vague answers. “Can you be more specific about what you mean by that?” or “Help me understand that better” when answers aren’t clear. Watch body language and tone as much as words. Discomfort with certain topics, defensiveness, inconsistent details, these non-verbal signals tell you a lot.
End interviews with opportunity for her to add anything. “Is there anything about your background or experience we haven’t discussed that I should know?” Sometimes candidates volunteer important information when given open-ended opportunity. Thank her for being straightforward even when answers revealed concerns. You want to encourage honesty, not punish it. Even if you’re not hiring her, appreciating her candor maintains professional relationship.
What To Do With Concerning Answers
If interview reveals red flags, don’t ignore them hoping they won’t matter. Trust your assessment. A pattern of terminations, multiple lies about employment history, significant concerning answers, these should typically end candidacy. One concerning answer might warrant more investigation before deciding. Multiple concerns together are usually disqualifying. Check every piece of information you can verify. References, employment dates, certifications, anything she’s told you should be confirmed. Candidates who are dishonest about one thing are often dishonest about others.
Be willing to keep looking rather than hiring someone you have concerns about. Desperation for childcare leads to bad hiring decisions. It’s better to extend your search than hire someone whose interview raised legitimate concerns. Sometimes concerning answers have good explanations. Give candidates opportunity to address your concerns before making final decisions. “You mentioned X and I want to make sure I understand correctly. Can you elaborate on that?” If clarification resolves the concern, fine. If it deepens it, that’s information.
The Cost of Not Asking
Families who avoid hard questions during interviews pay for it after hiring. You bring someone into your home who’s caring for your children. You deserve complete information about who they are and their work history. The awkwardness of asking tough questions is minor compared to the disruption, stress, and potential danger of hiring the wrong person because you didn’t want to be uncomfortable. Professional nannies expect thorough interviews. They understand that good families ask hard questions because they’re taking hiring seriously. Your willingness to ask difficult questions signals to quality candidates that you’re a professional employer who’s thoughtful about childcare.
The candidates who get defensive or offended by reasonable interview questions are often ones who can’t handle appropriate professional scrutiny. Strong candidates welcome thorough interviews because it shows you care about finding the right fit. After twenty years placing nannies in Miami and everywhere else, we can tell you with certainty that families who ask comprehensive questions including the uncomfortable ones make better hires than families who stick to surface-level friendly chit-chat. Your children are too important to protect someone’s comfort at the expense of thorough vetting. Ask the questions you need answers to. Ask them professionally. But ask them.
