6 min read

The Tailor & The Tutor: How to Make Each Session A Perfect Fit

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Tutoring is a lot like tailoring a suit:

Imagine the week before a big event (or a huge exam). You think you’re prepared to dress your best (or ace that test). You give your suit a try (or start your study time), and it turns out you could use a little help.

In order to be a successful tutor, understanding the specific needs of your tutees, both in and out of a tutoring environment, is crucial to the establishment of a strong tutor-tutee partnership and the success of your tutee. This not only consists of recognizing tutees’ learning behaviors and habits, but also getting familiar with what fosters a comfortable, productive space for every tutee.


This blog post will offer a step-by-step guide, modeled after the steps of tailoring a suit, to maximize the effectiveness of every session, from previous to new tutees. Through this, tutors can be intentional with planning their sessions, and tutees can benefit from faster, and more consistent, goal achievement.

Let’s begin with an outline of our steps:

  1. Ill-fitted areas - How/What does the current learning environment lack
  2. Take measurements - What “works” for this student?
  3. Tailor the suit - Design the session
  4. Trial run - Find and fix mistakes

1. Ill-fitted Areas - Something’s Not Right…

Just as you would go to a tailor, your tutee is coming to you, as a tutor, for a reason. It's because something’s just not right; the sleeves are too long, the hem’s coming loose, etc.

Students may find their current learning environment not a perfect fit as well; maybe the professor covers material too fast for their pace, or maybe the way the material is presented doesn’t align with how the student learns.

Hence, your first step when starting a session with a new tutee is to identify areas of the typical learning experience that fall behind.

Use the benefits of tutoring to your advantage:

  • Tutoring is uniquely more personalized than a college classroom setting, so reassure that tutees’ specific needs will be addressed during the session.

  • Additionally, tutoring offers a control of pacing and highlights certain aspects of material that tutees choose, which allows for a more student-led feel to lesson plans.

  • Finally, with peer tutoring specifically, there is a level of relatability that professors can tend to struggle with, so being able to foster a comfortable learning environment where students are less intimidated or anxious about their concerns is one of the best ways to be a successful tutor.

Listen to what your tutee needs. If your tutee is having trouble identifying what they lack in their current learning environment, you can use these categories as a guide to ask prompting questions to figure out the root of the issue.

2. Take Measurements - What “Works”?

This is where you begin to learn about your tutee, and what makes them the most comfortable and successful.

Here are three questions that provide a breakdown to understanding the typical student learning experience:

  1. How do you understand information best?: Is it through visuals? Step-by-step explanations? Example problems?
    The answer to this question might differ between courses, but this will begin your understanding of your tutee’s thinking process.

  2. How do you remember information best? Mnemonic devices? Flashcards? Self-quizzing?
    Sometimes, a student might be confused about exactly what helps them, or might not have a set way to study. My best suggestion for this is to tell them what works for you, no matter how unconventional it may be. This allows students who are a bit more unsure to have a “starting point” to begin figuring out their studying style.

  3. How do you retain information best? Are you the type to review a subject little by little everyday until an exam, or do you plan an all-day review session?
    This ensures that whatever methods you employ will actually benefit your tutee outside of the tutoring environment and continue to benefit them in other scenarios, classroom and beyond.

3. Tailor the Suit - It’s Tailoring Time!

Now it’s time to apply everything you’ve learned to your sessions. Remember, you want your student to look their best (or ace that test), so be as careful and specific with your solutions as possible.

This table provides examples of “tailoring” methods to make you an expert at identifying tutee needs, as it covers some general areas of student issue:

Tailoring (Issue) Tutoring (Method)
“The straps are too loose”
The learning environment isn’t structured enough for the student.
Create and share an outline for the session with your tutee, giving them more control over your time together.
“The waist is too tight”
The learning environment is too restrictive for the student.
Suggest a fun, engaging study method to encourage learning behaviors that aligns with your tutee’s studying style.
“The hem is too short”
The learning environment is too fast paced.
Take time to highlight exactly what in the material is confusing to your tutee and why it is confusing.
“The garment is too long”
The learning environment is not very engaging.
Ask questions throughout your session to gauge your tutee’s comprehension and reception of the material’s presentation.


Again, methods are also dependent on your tutee, but this establishes how to create tailored solutions from the students’ problem areas.

However, it’s not always the case that you will have the perfect solution for your tutee immediately…

4. Trial Run - Try It Out!

This is why evaluation is important!

Evaluation goes both ways, as your tutee is able to address what works, and doesn’t work, for them, in order to foster the best possible outcome of the tutoring session. For you, as the tutor, you are able to get insights on your abilities and, most importantly, begin building your tutor-tutee partnership.

For example, asking your tutee, “Have you utilized any methods outside of these sessions?”, assesses the applicability of each session to real-world scenarios, such as the classroom setting.

Asking, “Have these sessions made classes easier?”, evaluates the effectiveness of your sessions.

Finally, asking earnestly what a student prefers and doesn’t prefer about a session builds that tutor-tutee loyalty and encourages communication.

Evaluation is a tool, not an enemy, so don’t be afraid to take critique because it makes you a better tutor, which makes your tutee a better student.

By following these four areas of interest, tutors seeking to strengthen their tutor-tutee partnerships, in hopes of building future mentorships, or just increasing the effectiveness of their sessions, are one step closer towards a perfect fit!