How to Have a Great 1st Tutoring Session

By Learn To Be
December 31, 2023

I’ve been tutoring regularly for the past 2+ years, and the most common questions I hear from my fellow peer tutors all surround their very first tutoring session with their student — and understandably so! Regardless of whether or not you’ve tutored before, meeting and connecting with a new student is an exciting and slightly nerve-inducing task. While every student is different, there are a few overarching steps you can take to make your first meeting as successful as it can possibly be.

In this article, I’ll take you through:

  1. The ways you should prepare before the first session to set you and your student up for success, and
  2. Activities you can plan to complete during your session to help your student feel comfortable and to set the tone for future sessions!

While the below ideas can benefit almost all new students and tutors, the most principal takeaway is that, if you are going to be working with the same student regularly, your first session should be focused on relationship-forming, not solely academics. Yes, it’s important that you start to gauge your student’s academic levels and needs, but building connections with your student and with their guardian(s) is what will make you all more confident in your sessions moving forward.

Regardless of whether you choose to implement some or all of my suggestions, make sure that when meeting your student for the very first time, you open up a space for them to ask questions, share their interests and goals, and bond with you as a mentor.


1. Get to Know your Student through their Parent/Guardian (and maybe even their teacher!)

The best way to learn about your new student’s personality and tutoring needs is to speak to the people in their life every day; namely, a parent or guardian. Having a phone call or online meeting will enable you to 1) ask all of your questions and 2) start forming a relationship with your student’s family, both of which will be invaluable to you as you continue on in your tutoring journey. If you’re not sure what to discuss, here are some examples of useful introductory questions to ask:

  • Are there any additional details I should know about what material [student] needs help with?
  • Have you noticed if they have a learning style that suits them best (i.e. visual learning, auditory learning, or hands-on learning)?
  • What are their interests and hobbies?
  • What is the best way to communicate with you in the future — via email, call, or text?
  • Would you be open to sending me their teacher’s contact information so that I can learn a little more about what they’re working on in school?

If their guardian is willing to connect you with a teacher and that teacher is open to speaking with you, count yourself incredibly lucky! This is your opportunity to get more in-depth details on your student’s knowledge of the tutoring subject and what you should focus on to help your student thrive at school and beyond.

2. Have Backup Plans in Place

Based on your conversation with your student’s guardian (and/or their teacher) and any other information you have about the student, you’ll want to go ahead and make a plan for your first session (see the following section for ideas). However, as a new tutor, it’s incredibly important that you have some materials planned as backups if it turns out that your student isn’t at the learning level that you assume they are. If they are in the fourth grade, for instance, and you’re collecting some multiplication worksheets, you’ll also want to have a few backups on hand intended for second, third, and fifth graders. If you’re working on reading, make sure to have several different books available.

A huge purpose of the first session is to help your student feel comfortable, and part of that is ensuring that they’re not staring at material that is too difficult or easy for them, stuck feeling nervous or bored. By having backup activities, you guarantee that you will be able to support your student with the resources that they need, as well as getting a better sense of what lessons to plan moving forward.


1. Play icebreaker games!

You should set aside a few minutes every single week to simply chat with your student, but — particularly if they’re on the younger side — they may feel shy about speaking when they’re just getting to know you. An icebreaker game can never hurt to break the ice, so choose one that can be implemented virtually and make it one of the first activities that you complete with your student!

Charades, tic-tac-toe, 20 questions, or Pictionary can all make for great introductory games to get you and your student laughing and interacting. For older students, or students who are naturally more extraverted, you might also try including some icebreaker questions in your session, asking them about their friends, hobbies, learning styles…and anything else that pops up! Here are some ideas for conversation starters:

  1. What is one fun fact about yourself that people are always be surprised to hear?
  2. What are some of your favorite books, movies, and television shows?
  3. Do you play any sports? If so, which one(s)?
  4. What else do you like to do in your free time? What does a typical day look like for you?
  5. What’s your favorite class in school, and why do you like that subject?
  6. What specific topics that you’d like to work on together?

No matter which questions you choose to ask, make sure you intersperse them throughout the session so that your student feels less like they’re being interviewed and more as though they’re participating in a conversation.

2. Set goals with your student

Before you launch into academics, you want to ensure that you’re creating the right atmosphere for focused learning. I recommend asking older students — in middle school and above — to share the reason they signed up for tutoring.

  • Are they trying to increase test scores or receive a better grade in a class?
  • Is there a specific subject or unit in school that they’re hoping to improve in?
  • Do they love learning and simply want academic challenges that they are not able to receive in class?

Write down their “why” for tutoring and make a commitment to checking in on their goal every now and then. Younger students can absolutely participate in goal-setting, too! In fact, it’s a great way to increase their excitement and self-motivation for their studying. Instead of setting a larger goal that may seem more foreign to them, write down an overall goal only for yourself (for example, “learning how to read chapter books”) and work with the student to set short-term, easily attainable goals every month (for example, you could choose “learning the alphabet,” “learning 5 more sight words,” etc). Make sure the student is involved in this choice; by letting them help set the direction of their tutoring, they’ll become deeply invested in the material that they’re learning.

Lastly, don’t let goal-setting get in the way of highlighting their achievements! Whenever you pull out your goals, make sure you encourage your student by helping them describe what they have learned with you over the past few weeks. Not only will they be proud of their work, but by letting them think through and describe their accomplishments on their own, you’ll be teaching them a lesson in self-confidence and motivation that will stick with them for a lifetime.

3. Explore the online classroom

At this point in the pandemic, many of us are already familiar with Zoom and other virtual meeting platforms, but it can never hurt to revisit the features that you plan on using most often. If you plan to use the whiteboard feature, show them how to view it and make sure they’re able to write on it; if you are going to be sharing your screen, confirm that you both are seeing the proper screen…and so on. For younger kids, for whom this may be their first time navigating an online space on their own, having this practice time can be incredibly important. You can even try logging out and back in to make sure your student knows how to access the correct links and connect to the meeting!

You will save countless time by ensuring that you and your student are confident using all of the tools in your virtual toolbox. Spend just a few minutes on this during your first session, and see what a difference it makes next time!

For older students, you might try teaching them slightly more advanced strategies. For instance, show them how to split their screen so that they can see you on one side and another website — possibly a worksheet, or an online activity — on the other. Or, create a shared Google Drive folder to share any learning materials that you may want to pass back and forth. The sky’s the limit!

4. Introduce your subject!

The first session should be primarily focused on building a relationship with your student, whether that’s through goal-setting, ice-breaker games, casual conversations, or more. However, you’ll want to dedicate at least 10 minutes or so to introducing the subject you’ll be working on together. As I discussed earlier, you’ll want to have backup plans that you can pull from as the session progresses. You don’t have to really dive deep into the academics, but it’ll help set you up for the following week.

Don’t feel the need to stick to one specific subtopic in your first meeting, either; the goal is to get a better sense of what knowledge your student already holds and what areas they may need the most help in. So think big! If you’re teaching reading to a kindergartner, you might first see how she is with rhyming patterns and blending sounds together. Then, have her try reading the alphabet, or practicing sight words. You could even read a book to her to see how her comprehension is when listening to someone else read.

And that’s a wrap on your first session! With a little bit of preparation, you’ll be on your way to success in no time. It is so much easier to plan for future sessions after you have one already under your belt, so congratulate yourself on work well done and get excited for all of the memories you’ll make with your student!

By Learn To Be
December 31, 2023