You sound like a wonderful employer OP!

If your gut is telling you these things - then you are probably correct in your intuitions.

However it would not be your call to make overall.
It is up to your Nanny to let you know that she is burned out and/or is ready to move on.

I personally think you should be careful in what you tell her.
While I know you would mean entirely well > your Nanny may take your comments in a way where she may feel like she is no longer wanted any longer.

I would just keep the proverbial ball in your Nanny’s court & leave it up to her to let you know her future plans.
Hope this helps!

If you've tried to start the conversation and been unsucessful, then I would not bring it up any further. And do not ask questions about her personal health except as they are relevant to the job (e.g., if she's asking for time off or accommodations), though if she offers those details, listen thoughtfully and ask if there's anything you can do to help.

I understand you think involving the nanny gives her more options or flexibility, but any "benefit" (if the nanny even sees it that way) is offset by the weirdness and pressure of being involved in your employer's family decisions. What you can do to be nice without being weird in this case is:
1) if nanny has proactively brought up her plans (like she is applying to grad school now and wants to start a program next January), then do your best to accommodate what she's envisioning (preferred end date, scaling back to PT/occasional babysitting, whatever)
2) make your own intentions known -- tell her you'd love her to stay until Larla goes to pre-K in X years and that you're always open to conversations about what it would take to make that work for her. But at the same time, you'll be supportive if she decides she would like to make a career change. And leave it at that with no pressure for her to respond.
3) if you decide at any point you'd rather do some other form of childcare, then give her a good amount of notice so she can start making other plans

I have quarterly check ins with my nanny, ask her if she happy, are the girls too much for her and if we should consider daycare fulltime (our girls currently go part-time) and what we can help with, reinforce.

Anonymous wrote:We've had our nanny for a long time (5+ years). Our youngest is a bit of a handful (she's not terrible though, takes 2 hour naps, and is generally well behaved) and I'm getting the impression that the nanny would like to move on. She's a bit burnt out (she has health issues) and I know she wants a career change.

How can I start this topic with the nanny? I want her to know that we're okay with any decision she makes. We would keep her on until Pre-K if she would like to stay with us, but we understand if she wants us to use a daycare instead. She is wonderful and is very conscientious/dutiful. I think she feels like she can't abandon us. We're willing to work with her schedule so she doesn't have a gap in pay, or maybe she wants a break between jobs.

I'm sure this is just me being awkward, but I've tried to start this conversation a few times and haven't been successful.

If I'm correctly reading in between the lines, you want her gone. Right?

She’s going to think you are prodding her to leave.

She’s not enslaved. She can leave if she wants

Anonymous wrote:We've had our nanny for a long time (5+ years). Our youngest is a bit of a handful (she's not terrible though, takes 2 hour naps, and is generally well behaved) and I'm getting the impression that the nanny would like to move on. She's a bit burnt out (she has health issues) and I know she wants a career change.

How can I start this topic with the nanny? I want her to know that we're okay with any decision she makes. We would keep her on until Pre-K if she would like to stay with us, but we understand if she wants us to use a daycare instead. She is wonderful and is very conscientious/dutiful. I think she feels like she can't abandon us. We're willing to work with her schedule so she doesn't have a gap in pay, or maybe she wants a break between jobs.

I'm sure this is just me being awkward, but I've tried to start this conversation a few times and haven't been successful.

This is such a contradictory statement.

Anonymous wrote:When her annual comes up, you can talk to her about it.
Find out what’s been bothering her, find out about her recent health issues. Find out if there’s anything your family can do for her.

That's none of OP's business. Even nannies are entitled to privacy! If my employer ever started asking me personal questions, I would, not so politely, tell them it's none of their effing business!

When her annual comes up, you can talk to her about it.
Find out what’s been bothering her, find out about her recent health issues. Find out if there’s anything your family can do for her.

Anonymous wrote:This is not your place to do this. She's a grown adult. If she wants to leave she'll give you notice.

This. The entitlement of these parents is unreal.

This is not your place to do this. She's a grown adult. If she wants to leave she'll give you notice.

We've had our nanny for a long time (5+ years). Our youngest is a bit of a handful (she's not terrible though, takes 2 hour naps, and is generally well behaved) and I'm getting the impression that the nanny would like to move on. She's a bit burnt out (she has health issues) and I know she wants a career change.

How can I start this topic with the nanny? I want her to know that we're okay with any decision she makes. We would keep her on until Pre-K if she would like to stay with us, but we understand if she wants us to use a daycare instead. She is wonderful and is very conscientious/dutiful. I think she feels like she can't abandon us. We're willing to work with her schedule so she doesn't have a gap in pay, or maybe she wants a break between jobs.

I'm sure this is just me being awkward, but I've tried to start this conversation a few times and haven't been successful.