Day One: The First Tutoring Session

I’ve been a professional tutor for ten years, but the first day with any new family still scares me. I get irrationally nervous, eager to justify the expense and, to be quite frank, the awkwardness. In the end, I am a stranger coming in to spend an hour or two in the family room or at the dining room table. I want to make everyone feel at ease with the relationship. And make them feel at ease RIGHT NOW!

But this is a challenge because at ease for a parent and at ease for a student usually mean very different things: a parent is often looking for someone non-threatening but impressive, a credible and effective educator; a student usually wants someone who isn’t going to bore them to death for 90 minutes each week for the rest of the year. And, of course, I am also my own audience. I want to see improvement, evolution, increased sophistication and mental agility from myself. I also have to spend 90 minutes weekly with me, the tutor, for the rest of the year. And after ten years, if “Tutor Me” is just repeating himself, he’s tedious company. Each first day with a new client is therefore a moment where I can create a chance to stretch myself.

There’s a lot of pressure and a lot of conflicting impulses. But one consideration will always outweigh the others: my first responsibility is to the student. With that in mind, parents, here are my priorities for day one. Sometimes, maybe, it may not look like I’m doing what you want, but this is the way it’s got to go.


  1. I will waste time outright at the beginning. I need to chat with the kid. I will never ask about Math or English or History initially. In the first five minutes or more, I don’t care about those subjects. A lot of tutoring is about rapport, and first-impressions are key. I need to make sure I am someone your child feels comfortable talking to. I will ask about life at school, about interests, about TV shows, anything. I will add wry commentary -- never goofy, clowny distraction, but the kind of humor that lets the student know that I am listening and thinking about the things that interest them. I want to laugh with them and laugh at myself in the first fifteen minutes.

  2. I will spend time inefficiently. When we get to the subject at issue, I want the conversation to be very general. I want my students to do most of the talking. I want to hear what sort of language they use to talk about where they’re struggling and where they’re comfortable. If a student tries to redirect toward a specific homework problem or test result, I will redirect back to general challenges. The homework or test is a symptom. I want to know how it fits in the student’s self-concept. This is fuzzy stuff. It’s also important.

  3. I will not help your child complete an assignment. I want to make sure that my students do not look at me as someone who solves problems. I am someone who helps them help themselves solve problems. We may work through a couple of specific problems together, but they will not go quickly. We will digress to discuss context and methodology. My priority isn’t to get tonight’s assignment done. I want to orient my students toward underlying concepts and, even more so, toward process. These foster independence. And that is my ultimate responsibility. Your child will still have homework to do after I leave.

  4. I will not come with a lesson plan. No matter how much a parent and I might talk about a student and his or her challenges beforehand, in reality I know virtually nothing going in. Time spent prepping is time wasted and time that will only distract from the interpersonal stuff that day one is all about. The most important thing we need to know at the end of day one is whether we can work together.

  5. I should only stay an hour. In my experience the ideal tutoring session is 90 minutes. But on day one, we should spend just an hour. Day one is about the fit. Setting it up as something else (unless we’re in last-minute emergency test-review mode) is delusion.

These priorities are part of the reason I dread day one. I simply know that the best work I can do often isn’t going to look like the best work a parent (or even a student) expects to see. My hope is to make parents happy in the long run. But that’s the long run, and what I need to do in service of that at the outset is different. I’m always afraid I’ll let someone down on the first day. I lose sleep over it. I just can’t do it differently. A good tutor can change an academic life, but on day one, we should just talk.

Tags: Tutoring tips, Tutoring philosophy, subject tutoring, test prep, homeschooling
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