Which classes should you pick for the upcoming college (or high school) semester? Millions of students deal with this question twice a year. Many of us have asked this question at some point in our lives, some of us have even helped our kids or younger mentees navigate this question. One way to choose classes is to focus on the topics or subjects you’re interested in or want to learn more about. A better method is to pick the classes with the best teachers for you. 

A “good” teacher, with their enthusiasm, patience and resonant explanations can make you fall in love with any subject, no matter how hard or esoteric you initially conceive it to be. Similarly, millions of people have been put off from a subject or had their spark for it extinguished by a “bad” teacher.

Picking classes with great teachers is a hack I stumbled upon during my time as an undergrad at Princeton and greatly increased my happiness in an intense academic environment. I still use this method today to better navigate self-guided learning in topics I’m interested in, every time I pick a book to read, course to enroll in, or podcast to listen to. Thanks to the internet, we’re spoiled for choice with myriad sources of information to choose from about any topic we could be interested in. With so many options of who to learn from, picking the right teachers for you is more important than ever. How do we pick the best ones for us?

In this essay I want to explore two questions. First, “How do we find the best teachers for us?” Second, “What makes a good teacher?” I’ll do this by examining what I call “The Five Pillars of Great Teaching”.

The Five Pillars of Great Teaching

From my experience, I’ve noticed that the great teachers all have 5 things in common. They are:

1. Expert Knowledge

2. Skin in the Game

3. Beginner’s Empathy

4. Embracing Many Paths to Greatness

5. Long Term Focused

Pillar 1: Expert Knowledge

Imagine a maths teacher who was bad at maths or a swimming teacher who was bad at swimming? Their students are gonna have a bad time! Great teachers must be proficient in the things that they teach. You can’t teach something if you yourself don’t understand it.

Clarity of explanation is the hallmark of expert knowledge. When conveying new concepts, they know when to zoom in, to focus on technical details, and when to zoom out, to focus on the thematic and the abstract.

Teachers with expert knowledge of their topic carefully lay the foundations for their students to understand the topic. They do so brick by brick, ensuring that they don’t take leaps of logic or “handwave” away things that don’t make sense to their students. They understand all the steps they went through and are able to explain why something is the way it is and not resort to “the book says it’s like that” or “that’s what’s in the syllabus”. Teachers with expert knowledge don’t just teach to a syllabus or to the test. 

Teachers with expert knowledge have developed several mental models of their field that they can pass onto their students, so that they can serve as starting points to building their own maps of the topic. They know several different techniques to do one thing (e.g for doing long-division, brainstorming an essay, structuring an argument). This enables their students to use the methods and tools they like best, in order to explore the topic in the way that resonates most with them. 

The teacher who exemplifies Expert Knowledge for me is Benjamin Morison, a professor of Philosophy at Princeton, who taught classes on Plato and Aristotle during my time there. Ben is probably the best ‘teacher’, in the traditional sense, I’ve ever had. He introduced concepts which still shape my life to this day, like the idea that “All knowledge can be framed as answers to questions” and the concept of Akrasia, doing something despite knowing it is the wrong thing to do. Ben was a master explainer thanks to his clear and methodical way of making points, and his entertaining lectures and sense of humor turned ancient philosophy from a dry topic into one that was practical and colorful. 

However, expert knowledge, by itself, is not enough. Experts in a field can sometimes be so familiar with a topic and so deep in the weeds, that they forget what it’s like to not know basic concepts. This makes such experts difficult to relate to, leaving their students feeling alienated and guilty when they have trouble understanding. 

Moreover, experts, who are removed from the day-to-day practice of their chosen topic, can sometimes be disconnected with the reality of being a practitioner and applying the knowledge they share. Therefore, expert knowledge must be accompanied by practical knowledge about the topic they teach, gained by having Skin in the Game and Beginners Empathy.

Pillar 2: Skin in the Game

Skin in the Game acts as a balance against teachers being too theoretical, academic, or otherwise out of touch with reality, thus making the knowledge they impact less practically useful to their students. We can separate who to learn from and who to avoid based on whether they’ve successfully applied their expert knowledge in the real world.

Skin in the Game is important because it shows that a teacher has tested their expert knowledge in an environment where there is accountability and consequences for being wrong. It helps us be wary of teachers that teach about things that they’ve never actually done. Unfortunately, we see these types of teachers all the time in the modern world  -- people teaching courses about business who’ve never run a successful business and people who’ve never worked as software engineers teaching people how to code in coding bootcamps.

Teachers with Skin in the Game have developed richer understanding and more complex mental models from their time as a practitioner. This helps us ensure that teachers we follow pass the Chauffeur Test, to see whether their knowledge is true or is just memorized with no underlying understanding.

During my high school days at UWC Costa Rica, I was fortunate to have an IB Physics teacher who was previously a biomedical engineer. She had Skin in the Game from her actually being a practicing engineer. This enabled her to relate to physics in a way different from someone who was just a career physics teacher -  she would weave in anecdotes from her time doing car crash safety testing while we were studying motion and momentum and give us examples from her career about the application of physics in medical devices. Similarly, I was fortunate to have an IB Economics teacher who worked in finance as a banker for 10+ years, as she also brought much real world context to the subject.

Skin in the Game teaches students that it’s better to be a person in the arena, not an armchair professor, and that it’s better to learn from people in the arena. What does it mean to be in the arena? Theodore Roseveldt, defined the man in the arena in his iconic speech, Citizenship in Republic:

“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.” - Theodore Roseveldt, Citizenship in Republic

Tim Ferriss and Josh Waitzkin call this the difference between a “philosopher” - the person doing philosophy (or some other discipline) and the “philosopholigist” - the person that studies other philosophers, rather than doing it (or some other discipline) themselves. You want to learn from philosophers, not philosopholigists. That means learning writing from a prolific writer, rather than a person who studies writing theory. I learned this first hand while co-founding and operating a startup fresh out of college. I found that my team and I received consistently more useful and actionable feedback from investors and advisors who were practitioners - people who had either run a company before or worked at the sort of company we were aiming to build -  than we did from those with ‘business’ expertise but who lacked the context of operating the type of business we were building.

Pillar 3: Beginner’s Empathy

Skin in the Game alone is not enough to make a great teacher. Often, practitioners with expert knowledge are so in the midst of competition or practicing their craft that they aren’t able to translate that into useful knowledge for others. Those with Expert Knowledge and Skin in the Game have probably deeply internalized the skills and mindsets that make them great. Therefore, they might struggle to deconstruct their knowledge and explain it to others in a relatable way, or they might forget what it’s like not to know the fundamentals. Another reason is that these teachers over-emphasize the final 10% of the learning curve when they should be focusing on the first 90% - this can lead to people obsessing about ‘morning routines’ and pre-game rituals of great practitioners, rather than focusing on the fundamental principles in a domain. 

Beginner’s Empathy is the skill of being an expert in a topic while still remembering what it’s like to be a beginner. Such teachers remember what it’s like to not know things. They’ve deconstructed why they excel and are able to explain it to others in a relatable way.  Teacher’s with Beginner’s Empathy also know that different tactics and methods are required at the beginning of the learning curve, than at the middle and the high end. Josh Waitzkin, former US National Chess Champion and Tai Chi Push Hands World Champion, might be the best example of such a teacher. In his book, The Art of Learning, he presents the deconstruction of what made him so great from both a technical perspective and an emotional and psychological perspective in the fields of Chess and Tai Chi Push Hands by looking at the interconnecting themes in his approaches to both disciplines.

Unfortunately, this phenomena of top performers lacking Beginner’s Empathy is rampant at top universities. There you have professors and graduate students digging deep into one topic during their careers and then getting placed to teach classes, many of them introductory or survey classes. They zoom through topics, as the material seems elementary or obvious, leaving students confused and opting to self-study instead. I felt this at times during my freshman year in college, where it seemed better to skip class and read the textbook (or watch Khan Academy) than to go to lectures (the good news is I still passed). 

Beginner’s Empathy is important because it enables the teacher to relate to a topic from both an insider’s and outsider’s perspective. To beginners, who are still outsiders to a topic, teachers can focus on conveying principles and fundamental concepts, using analogies that a lay person could understand,only bringing in technical terms as needed. As students progress and become insiders, the teacher can start using technical terms and jargon more frequently and explore nuances and details of topics.

In college, I enjoyed Computer Science classes from Ed Felten and Arvind Narayanan, two fantastic professors at Princeton. They both had Skin in the Game, with Felten previously holding the positions of US Deputy Chief Technology Officer and Chief Technologist for the US Federal Trade Commission during the Obama administration. They were also able to approach topics from zero, remembering what it was like not to know something, and then build from the ground up. They embodied Expert Knowledge, Skin in the Game and Beginners Empathy and that’s what made them fantastic teachers. They helped me understand key topics in security and cryptography. That feeling, of concepts being familiar and not foreign, gave me confidence, which led to my becoming more interested in cryptocurrency and blockchain technology, and eventually my first startup.

Pillar 4: Embracing Many Paths to Greatness

There’s a tendency among those with Skin in the Game (Pillar 2), to see their path as the only path to success. They teach things as if the way they did it is the only way to do it and all other paths are wrong. Great teachers embrace the truth that there are many paths to greatness. They don't mold students into their own image or try to create an army of robots that speak, act and sound the same. The best teachers help their students not only achieve success in a domain, but help them express themselves in the artform. They help students find their own way.

We often see people teach things the way they got taught and then get surprised when their students don’t understand like they did. The best teachers use their expert knowledge to find unique ways to explain concepts to different types of students.

There’s also the danger that the teacher will try to portray their intuitions and experience in the field as the true way of relating to that field. The problem with that approach is that they developed those intuitions because they had certain psychological, physical and personal characteristics that colored the way they saw the topic. When a teacher tries to impose a way of thinking or relating to a subject on a student, or the student forces themselves to adopt the way of a teacher with very different psychology, physicality and personality, the student often alienates themselves from the topic. When this happens their students’ results drop and their love for the discipline drops as well, as they no longer relate to it in an authentic way. Take the case of  a very creative student in maths, who likes elegance and clever solutions, who has a teacher who’s extremely pedantic and prefers complex proofs and calculations, or a football (soccer) coach that loves to defend and suffocate teams, with a team full of players who love to create and play attacking, flowing football.

Now, this is not to say that teachers with different characteristics can’t benefit students. Teachers who embrace many paths to greatness are attuned to their students personality and way of relating to their domain. These teachers turn students into well rounded top performers, not by stifling their natural way of relating to the discipline, but by allowing the student to tackle their weaknesses or learn a different philosophy of playing while still preserving their natural approach, allowing students to integrate new material that might conflict with their current intuitions in a way that makes sense to them. In this way, the very creative math student can become more rigorous in his approach and the flair football player can learn to track back and defend when the team needs them.

Teachers who embrace the truth that there are many paths to greatness allow their students to develop their own learning style and love for the discipline. I experienced this first hand during my time in competitive high school debate. I used to think that great debaters had to fit a certain mold: be very emotive, fast talking, always use certain words in their speeches and, of course, have lots of hand movements. I had the good fortune of working with three coaches during my formative years (Alex De Jager, Thomas McLennon and Quintin Moodley) who helped me find my own way. They saw that I had a natural way of presenting persuasively:  when I was calmer, more relaxed, not rushing through lots of material and not trying to be overly energetic or loud. They helped me embrace my own way of debating and speaking that led to a relatively successful debating career. It also gave me confidence in my public speaking abilities, which has benefited me to this day, as I don’t try to “put on a show” or be someone else, but rather I stick to my own style when I speak in front of crowds or in meetings.

Pillar 5: Long-Term Focused

Great teachers are focused on long term outcomes for the students. They help students cultivate curiosity, creativity and a love for the learning process in their chosen discipline, so that students become aware of their progression and the barriers reaching their next level.

Teachers who are long term focused empower students to teach themselves, eventually rendering the teacher unnecessary.

Many teachers set their students up for failure in the long term by teaching with the objective of success in the short term. In school, examples of short term success would be teaching students to do well on tests, like the SATs, or to gain college admission. In the sporting world, this may be coaches teaching students tactics that work on low-skilled opponents in order to win an upcoming tournament (e.g openings traps in chess, stock arguments in debate), but would fail in the future against high-skilled opponents.

I saw this first hand, during my time as a Learning Consultant at Princeton. My job was to help other students design personalized strategies to help them achieve their academic goals. I consulted many freshmen and sophomores who came to me complaining of their struggles to adapt to the demands of academics in college. In many cases, the problem turned out to be that students didn’t understand how to prioritize topics in their classes and therefore didn’t understand which things were worth focusing on. It turns out that in high school, their classes had well defined syllabi and the teachers would tell them exactly what to focus on for the test.

Now, these students were good students --they managed to get into Princeton after all. However, they were brittle, as they had never encountered unstructured learning environments and were never forced to develop their own muscle of mapping the relative importance of topics and seeing how they fit together. Their high school teachers succeeded at doing their job of helping them get into college, but failed at developing them as independent learners. Fortunately, these students were self-aware enough to seek help, and many of them developed their own learning systems that served them well. 

Great teachers prepare students to be independent learners. I was fortunate to have one such great teacher during my time in college, Robert (Bob) Dondero. He embodied teaching for the long term and taught the most useful Computer Science class I took, called “Advanced Programming Systems”. He didn’t just focus on skills to pass the class, like syntax of programming languages or how to use a specific library or tool, but helped us see different ways of thinking around developing software, learning new technologies, language and tool selection and thinking in systems. Before his class, I was low in confidence around my programming abilities, from taking classes that moved too fast or were badly taught. However,  Professor Dondero’s patience and care, coupled with his long term focus on helping us become successful at building software for our own purposes -- whether it was for a career as a software engineer or just building side projects and MVPs -- rekindled my confidence in programming and building software.

How to find the right teachers for us? 

We should strive to find teachers that fulfill all five pillars of great teaching. From examining the Five Pillars of Great Teaching above, I hope you have ideas of teachers or coaches from your own life who embodied (or didn’t embody) each particular pillar. To further assist you to vet potential teachers in each of the Five Pillars of Great Teaching, here’s a non-exhaustive list of questions and methods:

1.Expert Knowledge

• In what way has the teacher demonstrated mastery in their topic?

• What do others say about that teacher’s expert knowledge?

• Are their explanations clear? 

• Do they build up foundations step by step, or do they skip steps in their explanations?

• Do their explanations resonate with you?

2.Skin in the Game

• Has the teacher done it (the thing you’re looking to learn) in the context that applies to you? For example, if you want to build a SaaS startup in the enterprise tech space, look to learn from people who’ve done so before or are doing it now.

• Is the person in the arena? Don’t take advice on parenting from people who’ve never had kids, or startups from someone who’s never started and ran one, and so on...

• You want to copy the rigor of the thought process and not just the actions of the practitioner. Often their experience isn’t the magic path, but serves as guideposts for what a successful path may look like.

3.Beginner’s Empathy

• Does the person start at basics or make assumptions about what you already know?

• How have other students who were also beginners under that teacher fared? 

• Does the teacher remember what it’s like not to know things?

• Do you feel scared or feel like you’re over your head? Probably a bad sign.

• Does the person have both an insider’s and outsider’s perspective on the topic?

4.Many Paths to Greatness

• Does the teacher claim to have the magic system? Or do they see the pros and cons of many systems?

• How is the teacher attuned to the personality and unique characteristics of the students?

• Pick teachers or role models suited to your unique characteristics at first, in order to build your intuition. For example, studying players who play like you do or think like you do, rather than just the ‘best players’ that everyone likes. 

• Watch out for teachers who try to take you away from your natural way of playing or relating to your discipline.

• Pick teachers who move at a pace you can handle, but not those that move too fast. 

5.Long-Term Focused

• Seek out teachers who understand that “what got you here, won’t get you there”. They balance methods to achieve short-term goals, with instilling habits that are healthy for long term development in a domain.

• Teachers that teach a single system or use templates to mold their students are not bad teachers per se. Systems and templates can be good starting points.

• Look for the ones that help you transcend the system rather than relying on it like a crutch forever.

• Does the teacher prioritize test scores or other short term outcomes? Do they claim to help you game the system? If so, red flag.

• Long term oriented teachers value the learning process and helping students understand where they lie in the learning curve above all else.

Which part of the article did you find most interesting? Let me know on Twitter (@avthars) or email me (avthar at avthar dot com) if you’d like to discuss it!