The Week That Tells You Everything
Here’s something we hear often at Seaside Staffing Company: “I’ve never had household staff before, and I don’t know what I don’t know. How can I tell if this is going to work out after just one week?” You’ve hired your first nanny for your Chicago family. It’s Friday afternoon after her first full week, and you’re trying to process everything you’ve observed. Some things feel right. Other things make you uncertain. You’re wondering which signals actually matter and which are just normal adjustment.
After two decades of placing Chicago nannies with families, from Lincoln Park to Winnetka, we’ve learned that the first week reveals almost everything you need to know about long-term success. Not in obvious, dramatic ways. But in patterns of behavior, communication style, problem-solving approaches, and relationship building that predict whether this placement will thrive for years or struggle within months.
The work we do at Seaside Staffing Company is never automated, and it’s never one-size-fits-all. We believe in helping families understand what the first week actually reveals so they can recognize success signals, address minor concerns before they become patterns, and trust their observations. When you’re evaluating your new nanny’s first week in Chicago, you need to know which signals indicate you made an excellent choice and which warrant immediate attention.
Green Light: They Ask Clarifying Questions Without Seeming Helpless
The first positive signal during your nanny’s first week is when they ask clarifying questions that demonstrate they’re trying to learn your family’s specific preferences without seeming unable to function independently. They’re not asking how to change a diaper or make a sandwich. They’re asking which park you prefer, how you handle screen time, or what your approach is to discipline.
These questions show your nanny respects that every family operates differently and wants to align with your specific approach. They’re not assuming they know better than you about your own children. They’re also not so insecure that they need constant hand-holding for basic childcare tasks.
At Seaside Staffing Company, we tell Chicago families to welcome appropriate questions during the first week. Your nanny is learning the unique ecosystem of your household. Questions about routines, preferences, and expectations are signs of conscientiousness, not incompetence.
Here’s what this looked like for a Lincoln Park family recently. Their new nanny’s questions during the first week included “I noticed Emma seems tired around three o’clock. Is that her usual naptime or should I try to keep her awake?” and “You mentioned limiting sugar. Does that include fruit juice or just candy and treats?” These thoughtful, specific questions showed the nanny was observing carefully and wanted to align with the family’s approach. Three years later, that nanny is still with them, and the mother told us those first-week questions revealed the thoughtfulness that has characterized the entire relationship.
Conversely, red flag questions during the first week sound different: constant basic inquiries that suggest the nanny lacks fundamental childcare competence, or complete absence of questions that suggests the nanny isn’t trying to learn your preferences or assumes their way is the only way.
Watch what your nanny asks during the first week. Thoughtful, specific questions predict success. Either too many basic questions or suspiciously zero questions predict problems.
Red Flag: They’re Consistently Late or Call Out
The second critical signal appears if your nanny is consistently late or calls out sick during the very first week. Yes, legitimate emergencies happen. Transportation issues occur. People genuinely get sick. But arriving late multiple times or calling out during the first five days of a new job demonstrates either unreliability or lack of commitment that will only worsen over time.
The first week is when people are presumably on their best behavior. They’re trying to make good impressions. They’re being extra careful. If someone cannot manage punctuality and reliability during this period, what happens when the job becomes routine?
At Seaside Staffing Company, we’ve learned that patterns established in the first week tend to continue or intensify. A nanny who’s late twice in the first week will likely be late regularly. A nanny who calls out on day three probably won’t improve in attendance.
Here’s a story from our Chicago placements. A family hired a nanny who called out sick on day two and arrived thirty minutes late on day four. The family, trying to be understanding and give grace, didn’t address it directly. By month three, this nanny was consistently unreliable. When the family finally raised concerns, the nanny was shocked because they’d never been told it was a problem. The family later told us they should have recognized those first-week patterns as dealbreakers.
We don’t expect perfection. One genuine emergency or one late arrival with excellent communication and valid reason isn’t concerning. But patterns of unreliability in the first week rarely improve. If you see this red flag, address it immediately and directly. If it continues, restart your search quickly before you’re more invested.
Green Light: Your Children Are Warming to Them
The third powerful signal comes from your children’s responses to their new nanny during the first week. You’re not looking for instant, deep bonding. That takes time. You’re looking for signs that your children feel comfortable and are beginning to trust this new person in their lives.
Watch for small moments: your toddler reaching for the nanny’s hand during a walk, your preschooler showing them a favorite toy, your school-aged child voluntarily sharing a story about their day. These small overtures indicate your children sense safety and warmth from this person.
Watch also how your children respond to your departures. Some protest is normal and healthy. But watch whether your nanny can effectively comfort them. Do your children settle relatively quickly? Do they seem genuinely engaged by the time you return? These patterns indicate your nanny has the emotional skills to help children feel secure.
At Seaside Staffing Company, we take children’s responses very seriously. Children are honest evaluators who can’t fake comfort. If your children are showing signs of warming to their new nanny within the first week, that’s a strong predictor of long-term success.
A Evanston family told us about their six-year-old son who was initially resistant to having a nanny. By day three of the first week, he was asking when she’d arrive and showing her his Lego creations. That early connection predicted the strong bond they’ve maintained for four years.
Conversely, if your children seem consistently uncomfortable, withdrawn, or scared by the end of the first week, investigate immediately. While some children need more time to adjust, persistent distress warrants serious attention.
Red Flag: They’re Not Following Clear Instructions
The fourth concerning signal appears when your nanny consistently doesn’t follow clear instructions you’ve provided, even after you’ve explicitly outlined expectations. Maybe you specified no screen time and you discover they’ve been using the TV. Perhaps you explained your approach to snacks and they’re doing something completely different. Possibly you gave detailed instructions about nap routines and they’re ignoring them.
We’re not talking about minor variations in approach or one-time mistakes. We’re talking about patterns where your nanny either isn’t listening to your preferences or doesn’t think your preferences matter enough to follow.
Here’s what makes this particularly concerning during the first week: if someone won’t follow your instructions when they’re supposedly trying to make a good impression, they certainly won’t follow them once the job becomes routine. This pattern indicates either poor listening skills, lack of respect for your authority as the parent, or fundamental disagreement with your approach that they’re acting on despite your clear direction.
At Seaside Staffing Company, we tell families that while some flexibility in method is fine, alignment on major approaches is essential. Your nanny doesn’t need to do everything exactly as you would, but they do need to honor your clear instructions about important matters.
A Chicago family recently discovered during the first week that their nanny was giving their toddler sugary treats despite explicit instructions about limiting sugar due to behavioral impacts they’d observed. When addressed, the nanny dismissed their concerns, saying “a little sugar won’t hurt.” That fundamental disrespect for parental authority ended the placement immediately. The family’s only regret was not addressing it on day one when they first discovered it.
If you observe this red flag during the first week, have a direct conversation immediately. If the pattern continues after clear redirection, end the placement. Someone who won’t follow instructions in week one won’t magically start following them later.
Green Light: They Communicate Proactively and Appropriately
The fifth positive signal appears in how your nanny communicates with you during the first week. They’re not overwhelming you with constant texts about minor details. They’re also not leaving you completely in the dark about important information. They’re finding the right balance of keeping you informed without making you micromanage.
Good communication during the first week includes brief updates about how the day went, heads-up about anything notable (good or concerning), questions about preferences when situations arise, and responsiveness when you reach out. They’re not defensive when you provide feedback or ask questions. They’re not oversharing inappropriate details. They’re professional and warm in their communication style.
At Seaside Staffing Company, we’ve learned that communication patterns established in the first week tend to continue. A nanny who communicates well from the start will likely maintain that throughout employment. A nanny who’s hard to reach or defensive during the first week will probably continue those patterns.
Here’s what good first-week communication looked like for a Naperville family. Their nanny sent a brief text each afternoon with highlights of the day and any relevant information. “Great day! Sophie ate all her lunch, we went to the park, she’s been a bit fussy this afternoon but I think she’s teething. See you at 5:30!” This balanced, informative communication style has continued for two years.
Conversely, red flag communication during the first week includes no updates unless specifically asked, defensive responses to simple questions, oversharing inappropriate details about the nanny’s personal life, or constant texting about minor decisions that interrupt your workday.
Pay attention to communication patterns in the first week. They reveal how this relationship will function long-term.
Red Flag: They Don’t Clean Up After Themselves
The sixth concerning signal appears if your nanny consistently leaves mess behind, whether that’s dishes in the sink after children’s lunch, toys scattered everywhere without attempting to tidy, or general disorganization in spaces they’ve used. While you’re not expecting perfection, you should see basic respect for your home and effort to maintain order.
This matters because it indicates their approach to the job. Professional nannies understand that part of their role includes maintaining reasonable tidiness in child-related areas. They’re not leaving chaos for you to handle when you get home. They’re teaching children to clean up. They’re modeling organization.
At Seaside Staffing Company, we tell families that while deep cleaning isn’t typically a nanny’s responsibility, basic tidying of spaces they and children occupy throughout the day is standard professional practice. If your nanny isn’t doing this during the first week when they’re theoretically trying to impress, they won’t start doing it later.
A Wilmette family discovered during their nanny’s first week that they were coming home to kitchens full of dirty dishes, play areas explosion of toys, and general disorder. When gently mentioned, the nanny seemed surprised, saying “I’m just here for childcare.” This fundamental misunderstanding of professional standards ended the placement. The family later told us the first-week mess was a preview of the lack of initiative they would have faced indefinitely.
Basic tidiness during the first week predicts professional standards. Consistent mess during the first week predicts ongoing frustration.
Green Light: They Show Initiative Appropriately
The seventh positive signal appears when your nanny demonstrates appropriate initiative during the first week. They’re not waiting to be told every single thing to do. They’re noticing needs and addressing them thoughtfully. They’re not overstepping by making major decisions without consulting you, but they’re handling situations that clearly fall within their realm of responsibility.
Appropriate initiative during the first week might look like: noticing you’re running low on diapers and mentioning it, organizing the diaper bag for the next day without being asked, starting to establish a toy rotation system to keep play areas manageable, or suggesting a new park they discovered that seems perfect for your children’s ages.
This balanced initiative shows your nanny is thinking about your family’s needs, taking ownership of their role, and using good judgment about what requires consultation versus what they can handle independently.
At Seaside Staffing Company, we value initiative as one of the most important qualities in excellent nannies. The difference between someone who just follows instructions and someone who thoughtfully anticipates needs is enormous in terms of actual household support.
A Gold Coast family told us about their nanny who, during the first week, noticed their toddler was consistently frustrated during art activities. Without being asked, the nanny researched age-appropriate art projects and implemented some modifications that transformed frustration into engagement. That proactive problem-solving has characterized the entire four-year relationship.
Watch for appropriate initiative during the first week. It predicts the level of engagement and support you’ll receive long-term.
Red Flag: They Bad-Mouth Previous Employers
The eighth concerning signal appears if your nanny speaks negatively about previous families during the first week. Whether it’s during casual conversation or in response to questions, if they’re criticizing former employers, speaking unprofessionally about past situations, or blaming others for everything that went wrong, recognize this as a significant red flag.
Here’s why this matters: if they speak negatively about previous employers to you, they’ll speak negatively about you to future employers. Professional discretion works both ways. Moreover, people who blame everyone else for problems typically lack the self-awareness and accountability that healthy working relationships require.
At Seaside Staffing Company, we tell families that while brief, neutral mentions of why previous positions ended is normal, extended negativity or blame is concerning. Professional nannies can discuss previous experiences without disparaging former employers.
A Lake Forest family heard their new nanny making multiple negative comments about a previous family during the first week. Red flag ignored. Six months later, that nanny left their employment and they later discovered she was telling prospective employers terrible things about them, most of which were exaggerated or false. They learned too late that the first-week pattern of negativity predicted how she’d eventually speak about them.
If your nanny bad-mouths previous employers during the first week, consider it a preview of how they’ll discuss you later.
Green Light: They’re Building Relationships With Your Whole Family
The ninth positive signal appears when your nanny makes appropriate efforts to build relationships not just with the children but with your whole family during the first week. They greet your partner pleasantly. They acknowledge older siblings. They’re friendly with your dog. They’re respectful of your space while also becoming part of the household ecosystem.
This doesn’t mean overfamiliarity or inappropriate boundary-crossing. It means professional warmth that recognizes they’re joining a family system, not just managing children in isolation.
At Seaside Staffing Company, we’ve learned that nannies who naturally understand how to integrate into family systems create the smoothest, longest-lasting placements. They build rapport with everyone, making their presence feel like support rather than intrusion.
A Chicago family told us about their nanny who, during the first week, made a point to learn everyone’s names including their elderly grandmother who visited frequently, asked respectful questions about family preferences, and demonstrated awareness of household rhythms. That social intelligence created a foundation for a five-year relationship where the nanny truly became part of the extended family.
Watch how your nanny navigates your family system during the first week. Natural integration predicts long-term harmony.
What To Do With What You’re Observing
So what should you actually do with the patterns you’re observing during your nanny’s first week? At Seaside Staffing Company, we recommend a balanced approach that addresses concerns while allowing appropriate adjustment time.
For green lights you’re observing, acknowledge and appreciate them. “I’ve noticed how thoughtfully you ask questions about our routines. I really appreciate that” or “I can see my daughter is already warming to you. Thank you for your patient approach.” This positive reinforcement encourages the behaviors you want to see continue.
For minor concerns that aren’t dealbreakers, address them directly and kindly. “I noticed the kitchen was pretty messy yesterday afternoon. Part of the role includes basic tidying of areas you and the kids use. Can we make sure that happens going forward?” Direct communication prevents small issues from becoming big problems.
For serious red flags like dishonesty, consistent unreliability, or children showing signs of fear, act immediately. Have a direct conversation if there’s any possibility of resolution. If the red flag is severe or continues after being addressed, end the placement quickly. The first week exists partly to identify deal-breakers before you’re more invested.
Here’s what we tell Chicago families: trust what you’re observing during the first week. These patterns are real. While some things improve with time and familiarity, fundamental issues with reliability, integrity, or professional standards rarely do.
A family recently told us they saw several concerning patterns during their nanny’s first week but talked themselves out of taking them seriously. “We thought we were being too critical” and “We wanted to give her more time.” By month two, those first-week concerns had intensified into serious problems. When they finally ended the placement, their biggest regret was not trusting their first-week observations.
The first week reveals patterns. Trust what you’re seeing and act accordingly.
The Seaside Support During This Critical Week
While you’ll never see us trying to become the biggest household staffing company, you’ll always see us working hard to remain the best. Part of what makes us best is the support we provide during that critical first week when families are figuring out whether they made the right choice.
We check in actively during the first week. We help families interpret what they’re observing. We distinguish between normal adjustment patterns and genuine concerns. We provide scripts for addressing issues directly. We support families who need to end placements quickly when serious red flags appear.
When you work with Seaside Staffing Company, you’re not alone during your nanny’s first week. You have experienced professionals who’ve seen thousands of first weeks and know which patterns matter, which concerns warrant immediate attention, and when to trust that things will improve with time.
Let us help you navigate that crucial first week with confidence, knowing what you’re observing and what to do about it.
