An annual check-in with your nanny is one of the most effective ways to strengthen your childcare partnership, support retention, and ensure everyone stays on the same page. While day-to-day communication is important, setting aside intentional time to connect once a year creates space for meaningful reflection, growth, and planning. An annual check-in helps prevent misunderstandings, builds trust, and shows your caregiver that their role is valued and respected.

Families who host annual check-ins with their nanny often find that small issues are resolved early, expectations stay clear, and the working relationship feels more collaborative and stable over time.

1) Why an Annual Check-In with Your Nanny Matters

Life with children changes quickly. Schedules evolve, developmental needs shift, and priorities evolve and grow. An annual check-in with your nanny allows everyone to pause and assess what is working well and what may need adjustment. It also gives your nanny a dedicated opportunity to share feedback, goals, and professional needs in a supportive setting.

When families skip this opportunity, frustrations can quietly build on both sides, long before you’ve even realized it’s happening. Hosting an annual check-in helps maintain transparency, encourages open dialogue, and supports long-term success for everyone involved (most importantly, your children!). 

2) Conducting a Successful Annual Check-In with Your Nanny

a) Step 1: Prepare Thoughtfully Before the Conversation

While extensive planning certainly isn’t required, a successful annual check-in with your nanny starts before you sit down together. Beforehand, take time to reflect on the past year. Consider what you appreciate most about your nanny’s work, where your household routines have changed, and what new needs may be emerging.

Encourage your nanny to prepare as well by letting them know the purpose of the meeting in advance. This ensures the conversation feels collaborative rather than reactive. Though there may not be anything you need them to prepare beforehand, preparation allows both parties to arrive with clarity, intention, and respect for one another’s time.

b) Step 2: Begin with Appreciation and Reflection

Start an annual check-in by acknowledging your nanny’s contributions to set a positive tone. Share specific examples of moments where their care made a difference for your children or supported your family’s daily life. 

Reflection should go both ways. Invite your nanny to share what they felt proud of this year and what challenges they encountered. An annual check-in works best when it feels like a conversation rather than a performance review.

c) Step 3: Review Roles, Responsibilities, and Boundaries

Over time, nanny roles can slowly expand without clear discussion. An annual check-in is the ideal moment to revisit responsibilities, schedules, and expectations. Review what tasks are officially part of the role and identify anything that may need to be adjusted moving forward.

This step is especially important as children grow older, start school, or develop new interests. Clarifying boundaries during an annual check-in helps prevent burnout and ensures everyone remains aligned.

d) Step 4: Discuss Growth, Compensation, and Future Goals

Professional caregivers value transparency around growth opportunities. Use your annual check-in with your nanny to discuss performance feedback, potential raises, benefits, or changes in hours if applicable.

This is also a time to ask about your nanny’s long-term goals. Understanding their aspirations helps families plan ahead and demonstrates respect for their careers. Or perhaps their long-term goal aligns with your future plans, like transitioning into a family assistant position. 

e) Step 5: Set Clear Goals for the Year Ahead

End your annual check-in with your nanny by looking forward. Discuss upcoming changes such as school transitions, new activities, travel plans, or schedule shifts. Set shared goals that support your child’s development and your household’s rhythm.

Documenting or outlining key takeaways from the meeting can be helpful for everyone. A brief summary reinforces clarity and ensures the annual check-in leads to actionable next steps rather than vague intentions.

3) Making the Annual Check-In a Lasting Practice

An annual check-in with your nanny is not about perfection. It is about communication, respect, and consistency. Families who prioritize this practice often experience stronger relationships, smoother transitions, and better continuity of care.

By treating your nanny as a trusted professional partner and creating space for honest reflection, an annual check-in becomes a powerful tool for long-term success. It’s a small investment of time that delivers meaningful benefits for your children, your household, and your caregiver.