Since sharing Tips for making homework fun, in which I said that I had taken on a tutoring role, I have had seven sessions with my 5th grader. He is a delightful child—sweet and eager. I have looked forward to every session and spent considerable time in between thinking about how to help him achieve the potential I know he has.

I've learned a lot in the past month, as I have endeavoured to make our get-togethers both interesting and educational. Here's what I've picked up so far.

I've realized that every encounter is an opportunity to teach something or to test comprehension. Since our second session, my young student has accepted my offer of a snack—a humble apple being his refreshment of choice. But an apple is more than an apple: it's a prop for learning fractions. Cut it in two and we have two halves, in four and we have four quarters. Put two one-quarter pieces together and we have two quarters or one half. Put two one-eighth pieces together and we have two eighths or one quarter.

One of our more memorable tutoring sessions was devoted entirely to baking. The recipe? Award-Winning Soft Chocolate Chip Cookies. The goal? Practise skills while engaging in a fun and rewarding activity. The task involved cutting a recipe in half. For example, 2 cups of flour became 1 cup (indeed 2¼ cups became 1⅛ cups), 2 eggs became 1 egg, 1 teaspoon of vanilla became ½ teaspoon of vanilla. I used multiple sets of measuring cups and spoons to demonstrate various fractions. My student helped with all aspects of measuring and mixing, showing much greater facility in the kitchen than I had expected. He read out the ingredients and the instructions. Together, we made 24 balls of cookie dough, which we placed on 2 cookie sheets in a 3x4 grid on two silicone baking mats. This provided further opportunity for counting and multiplying. Even the baking time could be used to demonstrate fractions and division, as I asked for his help in splitting the 10 minutes of baking time into two so that I could rotate the cookie sheets halfway through the bake. When I took the cookies out of the oven, I told my helper that I would give him half the cookies to take home. More division.

On another occasion, I used Astérix and Obélix figurines to help my student read an analog clock. Astérix (the shorter character) would read the small, hour hand, while Obélix (the taller character) would read the long, minute hand. I played Astérix, saying (in my best Astérix voice): "The short hand is after the 2, so it must be 2:00 or two something." My young friend would then take Obélix and move him around the clock face, count by fives to identify the minute, saying (in his best Obélix voice): "Five, ten, fifteen, twenty, twenty-five, thirty—it's 2:30!"

Astérix and Obélix have made several appearances in our tutoring sessions. When my student was reviewing angles, I suggested that acute angles were small and cute, like Astérix, and obtuse angles were big and broad, like Obélix. Coincidentally, acute and Astérix both start with A and obtuse and Obélix both start with O. How fortuitous!

Astérix and Obélix also served as main characters in a story I wrote expressly for my student. "The Magic Apple" told of the discovery of an apple that the two Gauls had found and decided to share. But before they could eat their halves, two more characters arrived: Joy and Sadness from the movie Inside Out (I happened to have the set of characters from the film). Now the apple would need to be cut in quarters. But before they could eat their quarters, four more characters arrived: Anger, Fear, Disgust and Bing Bong. At each point in the story, my student needed to fill in the blank to identify the fraction of the apple each person would receive. And, of course, he had a lot of text to read, while I moved the characters around to recreate the story with props.

For today's session, I introduced a new tool: a bingo card that I developed with various activities in four categories: Language, Math, Science, French. I gave my student the choice of activity, insisting only that he pick several from different categories. After he had completed each task, I let him choose a sticker to put on the appropriate square on his bingo card. Each task completed earned him two minutes of chess time, adding up to 10 minutes of the strategy game by the time we had finished today's session.

As much as possible, I try to say yes to requests, such as using Astérix and Obélix figurines as stand-ins for our kings in a game of chess, or starting our session with my student's favourite activity: a lesson of Duolingo in French. And when my charge said he liked trolls, I searched for a story about trolls, finding Bruce Coville's Trolled at the Ottawa Public Library. I decided to start with the first book in the series, Cursed.

I realized after presenting "The Magic Apple" to my student that my wall of text (one page, single sided) was probably overwhelming. So I decided to try an e-book, with its short line length and adjustable font, for our next reading activity. I've even considered using audiobooks, which—although they don't offer a chance for the student to read—could still be useful for testing comprehension.

Knowing that some people are more visual, while others are more auditory, and still others are more kinesthetic or tactile, I've added a variety of tools to my tickle trunk:

I'm hoping that the variety and breadth of tools will keep our tutoring sessions engaging and ensure that I land on approaches that will be the key that unlocks learning.

Most of our sessions have concluded with a game of chess. Little did I know 50 years ago when I played chess with my brothers or won the chess championship in my elementary school four years running that I would one day be very happy to have picked up the game in my youth. Chess is the fun reward for working hard during our hour together. But like the apple, chess is more than a game. It's also an opportunity—according to 8 Critical Thinking Skills Kids Learn at Chess Camp—to reinforce such skills as problem solving, abstract reasoning, calmness under pressure, patience, sportsmanship, creative thinking, pattern recognition and strategic thinking.

Learning something new and trying to remember something we studied a day or week ago can be daunting for all of us. But it can be especially challenging for a child to stumble in their learning in front of an adult who, to them, may appear very smart. So I try to empathize with my charge. When he makes a mistake in French, I say, "I understand. I make a lot of mistakes in Italian." Or when he tells me that he understands certain words but can't define them for me, I say, "I know how that is. I often see words that make sense to me but I can't provide a definition to someone else."

When he pauses an activity to tell me about something that went on at school, I allow the pause, validate his feelings, and ask questions. It's important that he knows that I see him as a human being, and not simply as a "human doing."

An oft-repeated bit of encouragement in Duolingo is this: focus on progress, not perfection. When I started learning Brazilian Portuguese in Duolingo, I hated making mistakes. I wanted to learn all the rules and memorize all the vocabulary as quickly as possible. If only I had known that the time I spent creating verb charts and vocabulary lists would have been better spent simply progressing through the lessons, making mistakes and learning from them. It was the repetition in the lessons that made the difference, not the studying of the language like a subject. As they say at Duolingo, practice makes progress.

My experience learning Brazilian Portuguese, and now Italian, is helping me in my tutoring. I recognize that my student doesn't need to be perfect or understand a concept in all its complexity from his first exposure to it. With repetition, his understanding will grow and the knowledge he builds over time will become second nature. Along the way, I will provide positive feedback and focus on what he's getting right.