Is There Anything You Wish You Had?

Last month I was out for a meal with a large group of admission leaders when our server asked a question that stopped me in my tracks.

All of our meals had arrived. This was the moment when you expect some version of “Does everyone have everything?” or “Need anything else?”

Instead, she asked: “Is there anything you wish you had?”

Dear readers, I’m not stopped in my tracks often. This question caught me so by surprise my brain glitched for a second. I asked her to hang tight for a second, caught the attention of the table, and asked her to say it again. I was sitting with people whose work depends on asking questions and helping families feel welcome. I wanted us all to hear that one.

Familiar moment, different invitation

Think about how often someone asks, “Need anything else?” And how often we answer without really thinking.

“Nope.”

“I’m all set.”

“All good, thanks.”

Sometimes we are all set. Sometimes we could use something, but it feels too small to mention. We don’t want to be difficult. The person asking looks busy. Or the answer comes out before we’ve even considered the question. Our server’s question interrupted that familiar exchange. I actually paused to think about what might make my meal better.

There was something so generous about the word “wish.” It gave us room to ask for something beyond what was strictly necessary. It conveyed to me that she was interested in our experience and had time to hear the answer. In a busy restaurant, that small moment made me feel like a real guest.

It made me think about how much care can be communicated through an ordinary interaction (do I have any Unreasonable Hospitality fans still reading?). Our meals were already on the table. She could have asked the expected question, received the expected answer, and moved on. Instead, she made space for us to consider what we wanted.

What do your questions make room for?

Naturally, my mind went to schools. We ask families questions all the time. At the end of a tour. After an interview. In a follow-up email. During an admissions event.

“Any questions?”

“Does that make sense?”

“Anything else we can help with?”

These are reasonable questions. I know I asked them plenty of times. But I wonder how often they produce the same automatic responses we give a server.

A parent says, “No, I think we’re good,” while still wondering whether their daughter will find friends.

A student says she enjoyed the visit, but hasn’t mentioned the part that made her wonder if she’ll be able to keep up in the classroom.

A family understands the enrollment process, yet still feels uncertain about whether the school is right for them.

We gave them an opportunity to speak. But did we ask a question that helped them find the words? 

There are other ways into those conversations:

“What are you still trying to picture about your daughter being here?”

“What (or Who) do you wish you’d had a chance to see today?”

“What feels clear, and what are you still working through before enrolling?”

Each invites a more specific answer. Each gives someone permission to have an unresolved thought, a concern, or a wish (you know, like any human would!) and for us to be the one who helps. And you know who people remember in the future? Yep, the person who helped them. Tell me that’s not true. 

The answer needs somewhere to go

Of course, changing the question only helps if we’re prepared to listen to the answer.

If a parent shares a concern and we immediately reassure them, we may miss the chance to understand it. If a student tells us what she wishes she had seen, we have to consider how to help her see it. If several families raise the same uncertainty, that deserves attention beyond the next follow-up email. The key is in listening, probing a little deeper, and not rushing to provide an answer. Keep the conversation going. 

And this is where a small interaction can inform larger decisions. What do families repeatedly need help understanding? Where does our process leave them hesitant to ask? What are we learning that should change the way we communicate, plan visits, or support students?

Those are questions worth bringing back to your team. The people having these conversations every day hold insight that can help your school improve the experience it offers.

A question worth noticing

I don’t know whether our server always uses that phrase or how she came to use it. I just know it caught my attention, and I’m still thinking about it nearly a month later. She took a routine moment and made it feel personal. With a few words, she helped me believe that whatever I might ask for would be welcome.

Schools put a great deal of thought into making people feel that way. Sometimes the next opportunity is in a question we ask so often that we’ve stopped hearing it.

“Is there anything you wish you had?”

I’m so glad she asked.