Every year around the second week of January, a San Francisco family we work with sits down with their nanny for what they call their “annual reset conversation.” They’ve been doing it for six years now, ever since the nanny’s third year with them when small frustrations had built up on both sides but neither party felt comfortable bringing them up. That year, they stumbled into a January conversation about how things were going, discovered all kinds of minor issues that were easily fixable once discussed, and made adjustments that dramatically improved the relationship. Now it’s ritual. Each January, they review what worked well last year, what didn’t work as well, what needs to change, and what they want to accomplish together in the year ahead. Scope gets adjusted, compensation gets discussed, schedules get refined, and everyone starts the new year aligned and clear about expectations. It’s preventive maintenance for their nanny relationship, and it’s kept them together successfully through kids growing, family circumstances changing, and all the normal evolution of household employment.
Most families don’t have structured conversations with their nannies about how the arrangement is working. They drift along assuming everything’s fine or dealing with problems only when they become crises. January offers a natural checkpoint that makes these conversations feel appropriate rather than awkward. The new year creates psychological permission to discuss changes, make adjustments, and reset dynamics that may have gotten stale or problematic. We’ve been placing nannies in San Francisco and across major markets for over twenty years, and we’ve watched families who use January as a regular checkpoint build stronger, longer-lasting relationships than families who never create space for these discussions. Let’s talk about how to have productive annual reset conversations, what to discuss, how to make changes that serve everyone, and why using January this way can prevent the problems that end otherwise good placements.
Why January Works for These Conversations
The calendar change creates natural opportunity for reflection and reset. Everyone’s thinking about what worked last year and what they want to change this year. Having a conversation about your nanny arrangement in that context feels normal rather than coming out of nowhere mid-year. January follows the holiday season when schedules were disrupted, routines were off, and everyone experienced the household under stress. That recent experience often reveals what’s working well and what needs adjustment. Issues that were manageable during normal months become obvious during holiday chaos. Use those observations while they’re fresh.
The psychological fresh start that January provides makes people more willing to make changes. If something wasn’t working last year, the new year feels like the right time to do it differently. That openness to change on both sides creates productive conversations. Many families do financial planning and budgeting in January. Having compensation conversations about your nanny’s wages fits naturally into that broader financial review. It’s easier to discuss raises or benefit changes when you’re already reviewing household finances. Performance review cycles in many industries happen in January or early in the year. Bringing that same structure to household employment normalizes the conversation and makes it feel professional rather than awkward.
School schedules, childcare needs, and family routines often change in January as kids return to normal school schedules after holiday breaks. That’s natural time to discuss whether your nanny arrangement needs adjustment to match new routines. If issues have been building throughout the previous year, January offers a socially acceptable time to address them. Rather than bringing up problems that feel old and stale, you’re having a forward-looking conversation about the year ahead that allows addressing past issues in context of making the future better.
What to Discuss in Your Reset Conversation
Start with what worked well last year. Before diving into problems or changes needed, acknowledge what’s been good. What did your nanny do that you genuinely appreciated? What went smoothly? What are you grateful for? Starting positive sets collaborative tone and reminds everyone that the relationship has value worth maintaining. Then discuss what didn’t work as well. Frame this carefully. Not “here’s everything you did wrong,” but “here are some areas where things were challenging or where I think we could improve.” Focus on situations and outcomes rather than attacking character or competence. “The morning routine has been rushed and stressful” rather than “You’re disorganized in the mornings.”
Talk about whether the current scope and responsibilities still match what you actually need. Many nanny positions evolve gradually without explicit discussion. Children grow, needs change, families add responsibilities incrementally. Is the current job description still accurate? Has it expanded significantly? Do certain tasks need to be added or removed? Get explicit about what you’re actually expecting. Discuss schedule and hours. Are the current hours working for both parties? Does anything need to change? If you’ve been regularly asking for extra hours or flexibility, should those become part of the base agreement with appropriate compensation adjustment? If she’s working fewer hours than originally agreed, should you reduce guaranteed hours and compensation?
Have an honest compensation conversation. When did you last give a raise? Is her compensation keeping pace with cost of living increases and market rates? Has her performance warranted increase? Is there budget to provide one? Professional nannies expect annual compensation review at minimum. Even if you can’t provide increases every year, having the conversation shows you’re thinking about fair compensation. Review benefits and perks. Is the current benefits package adequate? Does she need health insurance if you’re not providing it? Is PTO sufficient? Are there other benefits or perks that would be valuable to her that cost you little to provide?
Discuss communication and how you’re working together. Is the current communication style working? Would she like more check-ins or fewer? Are there ways you could communicate more effectively? Are there things she needs from you that she’s not getting? This is two-way conversation, not just you evaluating her. Talk about goals for the year ahead. What do you want to accomplish together with your children’s care and development? What does she want to work on professionally? Are there skills she wants to develop, training she wants to pursue, ways she wants to grow in her role?
How to Structure the Conversation
Schedule it formally rather than having an impromptu conversation. “I’d like to sit down with you for an hour next week to talk about how things are going and what we want to accomplish this year. Does Tuesday evening work?” Give her time to prepare her own thoughts rather than ambushing her. Choose a time and place where you can talk without interruption. Not while she’s chasing your toddler around. Evenings after she’s done working, or a weekend coffee meeting if that works better. Somewhere you can both focus on the conversation.
Come prepared with specific examples and clear thoughts about what you want to discuss. Don’t wing this conversation. Have notes about areas you want to address, examples of what you’re referring to, and ideas about potential solutions. Your preparation shows you’re taking this seriously. Create safety for her to be honest. Start the conversation by explicitly saying you want to hear her perspective, that you value her input, and that the goal is making the arrangement work better for everyone. If she believes honest feedback will create problems for her, she won’t give it. Show through your response that you can handle honest conversation without getting defensive or punitive.
Listen more than you talk. This shouldn’t be you delivering a performance review. It should be collaborative discussion. Ask questions, listen to her responses, make space for her to share her own concerns and needs. Take notes during the conversation. Both parties should leave with clear understanding of what was discussed and what changes are being made. Written notes prevent later confusion about what was agreed to. End with clear action items and timeline. If you’re going to increase compensation, when does it take effect? If you’re changing schedule, when does that start? If you’re addressing communication issues, what specific practices will you implement? Don’t let the conversation end without concrete next steps.
Making Actual Changes
The conversation is worthless if nothing changes afterward. If you identified problems or areas for improvement, implement solutions promptly. Don’t have the conversation, agree to changes, and then continue doing everything the same way. That teaches your nanny that these conversations are performative and meaningless, which guarantees she won’t be honest in future ones. If you committed to compensation increases, process them immediately. Don’t let it drag out for weeks or months. If you said you’re giving her a raise effective February 1st, make sure that happens. If you agreed to schedule changes, implement them on the agreed timeline. If you discussed adding or removing responsibilities, update her actual day-to-day work accordingly.
If you identified communication improvements you’ll make, actually change how you communicate. If you said you’d do weekly check-ins, put them on the calendar and honor them. If you committed to providing clearer direction about certain tasks, follow through. Follow up a month later to check how the changes are working. “We made several adjustments after our January conversation. How are they going? Is anything working better? Is anything still not quite right?” That follow-up shows you’re serious about continuous improvement and gives opportunity to make further refinements.
Document the changes if they’re significant. If you’ve modified her schedule, adjusted compensation, changed scope, or made other substantial changes to the employment arrangement, update her employment agreement or create written confirmation of the new terms. That protects both parties and prevents future confusion. Be patient with adjustment period. Changes take time to implement fully and to evaluate whether they’re actually improvements. Don’t expect immediate perfection. Give new approaches a few weeks to settle in before assessing whether they’re working.
When the Conversation Reveals Bigger Problems
Sometimes your January reset conversation uncovers issues more serious than minor tweaks can fix. Maybe you discover she’s been deeply unhappy for months. Maybe you realize the fundamental fit isn’t working. Maybe she reveals she’s planning to leave. Maybe you realize you can no longer afford her or no longer need full-time childcare. When serious problems surface, don’t panic or get defensive. Take the information seriously and think carefully about how to proceed. If she’s unhappy enough that retention is questionable, ask directly whether she wants to stay and what it would take to make staying worthwhile. Don’t assume the relationship is unsalvageable until you’ve explored whether there’s any path forward. Sometimes big problems have solutions if both parties are willing.
If it becomes clear that the arrangement isn’t working and won’t work, have honest conversation about timeline for ending employment. Can you transition over two months? Three months? What works for both parties? Parting professionally and gracefully when fit isn’t right is better than forcing a deteriorating relationship to continue. If budget has changed and you can’t maintain current compensation, have that honest conversation. Maybe she’s willing to reduce hours. Maybe you can find middle ground. Maybe she needs to seek employment elsewhere. Either way, honesty is better than silently resenting the cost or trying to force her to accept less than agreed compensation.
If the children’s needs have changed significantly and you’re realizing you need different expertise or approach, acknowledge that. “The kids have gotten older and I think we need someone with different strengths” is honest and allows for graceful transition rather than letting frustration build. If your own circumstances have changed in ways that affect the arrangement, share that information. Job changes, financial changes, family changes, health changes, all of these can legitimately affect household employment needs. Your nanny deserves to know what’s happening so she can plan accordingly.
What If She Brings Up Compensation and You Can’t Afford Increases
This is one of the hardest scenarios families face. Your nanny has been with you for several years, she deserves a raise, you agree her compensation should increase, but your budget genuinely can’t absorb higher costs right now. How do you handle that conversation? Be completely honest about the financial reality. “You absolutely deserve a raise and I wish I could provide one. Our financial situation has changed and we’re not able to increase compensation right now.” Honesty shows respect even when the answer is no. Discuss timeline for when a raise might be possible. “I’m hoping by mid-year our finances will stabilize and we can revisit this. Can we plan to have this conversation again in June?” That gives her something to hold onto even if immediate increase isn’t possible.
Look for non-monetary benefits you can provide. Maybe you can’t increase pay but you could add PTO days, provide flexible scheduling she’s wanted, cover professional development costs, or offer other benefits that have value to her without significantly increasing cost to you. Be open to alternative arrangements. Maybe she reduces hours slightly to match what you can afford. Maybe you bring in a nanny share partner to split costs. Maybe there’s creative solution that works for both parties. Understand she might need to find higher-paying work if you can’t provide competitive compensation. Don’t take it personally or make her feel guilty. She has the right to seek employment that meets her financial needs. If she does leave over compensation, provide excellent references and maintain positive relationship. She didn’t leave because she’s ungrateful or disloyal, she left because she needs to support herself financially.
Building This Into Your Annual Routine
Once you’ve had one productive January reset conversation, make it annual ritual. Put it on your calendar for the second week of January every year. Make it normal part of how you manage your household employment relationship. Over time, these conversations get easier and more productive. The first one might feel awkward, but by the third or fourth year, both parties expect it and come prepared with thoughtful input. Regular reset conversations prevent problems from building silently. Small issues get addressed before they become relationship-ending problems. Resentments get aired while they’re still manageable rather than after they’ve poisoned the relationship.
Annual review and adjustment keeps compensation in line with performance and market rates. Your nanny knows she’ll have annual opportunity to discuss compensation, which reduces stress and job searching driven by feeling undervalued. Regular check-ins strengthen communication overall. The trust built through these conversations makes daily communication easier and more effective. You’re not just employer and employee going through routines, you’re partners working together toward shared goals with regular space to align and adjust.
Families who build reset conversations into annual routine maintain nanny relationships years longer than families who never create that structure. Those extra years of stability and continuity benefit everyone, especially the children who get consistency of caregiver rather than repeatedly adjusting to new nannies. The hour you invest in a thoughtful January conversation saves countless hours of dealing with problems that could have been prevented, recruiting new nannies to replace ones who left over unaddressed issues, and training new employees when the previous relationship could have been salvaged with better communication.
If you’re a San Francisco family or a family anywhere with a nanny you value, use January as your prompt to have this conversation. You don’t need elaborate performance review systems or complicated processes. You just need willingness to sit down together, reflect on the past year honestly, discuss what needs to change, and commit to making those changes. That simple annual practice can transform your nanny relationship from adequate to excellent and keep valuable employees in your household for years instead of losing them to preventable problems.
