Teaching matters for business because learning fuels modern day organizations and entrepreneurs. It's not surprising, for example, to find that Adam Robinson is not only the cofounder of a successful test‐prep company, but also a chess master. He's a masterful learner, and most likely, through a combination of hard work, intuition, and natural aptitude, he cracked the codes of these two complicated systems and then mapped the fastest routes through them. His operating principle? “Outflanking and outsmarting the competition” (Robinson, 2018).

Folks like Robinson build off the parallels between the art of teaching and good business practices. One of his key insights originates with a behavioral study by psychology professor and decision researcher, Paul Slovic. Slovic studied the effects of information on eight professional horse handicappers, that is, people who bet on the outcomes of horse races for a living. Would knowing more help them to perform better?

In the first round of the experiment, they were given five pieces of information that they deemed most useful for their line of work and were asked to make predictions, based on the information, on the probable outcome of races. In the last round, they were given 40 pieces of information, and likewise, asked to use it to bet on horses.

Here's what happened:

[The] average accuracy of predictions remained the same regardless of how much information the handicappers had…Three…showed less accuracy as the amount of information increased, two improved their accuracy, and three were unchanged. All…expressed steadily increasing confidence in their judgments as more information was received. (Heuer, 1999)

The variance in accuracy is interesting, but the real story begins, as all good con jobs begin, at the point where confidence is built up in the mark. More information, more facts, more supposed insight, did not lead to better outcomes for the horse handicappers. Those inputs only led to increased certainty for them, only led to a situation in which they could con themselves into behaving in a way that would not, ultimately, help themselves.

The same ruts hold for investors, according to chessmaster Robinson. In a Q&A he did for the Tim Ferriss Podcast, he expounds upon Slovic's study, taking some swipes at human nature in the process. If, for example, he sees certain investors touting the fact that it “makes no sense” that a particular sector, say, energy, is trading at increasingly lower prices, he often concludes that the sector has lower to go because those same investors are “probably doubling down on their original decision to buy energy stocks.” Eventually, as a result of their confidence in their own narrative, “they'll be forced to throw in the towel and have to sell those energy stocks, driving prices still lower” (The Tim Ferris Show, 2018).

Robinson, importantly, is not saying that he can read the market or predict the future. He's simply stating that he himself prefers to bet on the fact that human reactions to the world are often based on their models of the world. Like some poker players, he prefers to play the people at the table rather than the cards in his hand. He prefers to watch where the people are likely to go wrong, and then work with that.

Add Yourself to the Situation

In a business relationship or transaction, we're likely to go wrong when we remove ourselves from situations that require our presence.

Allowing a robot to answer your phone might save you money, but it can also cost you customers if they begin to feel alienated and so go looking for a company with a touch more like their own. Sending an email blast to hundreds (or thousands) of prospective customers for your software, even if it's personalized with their names in the salutation, may increase your yield of meetings, but it can also create a negative association with your name or company when you send your second or third touch point. Automatically scoring a check for understanding following a training on a new home insurance offering is easy to measure and convenient for sharing results, but it may certify too soon someone's readiness to use that training knowledge in the field.

While there may be reasons to automate certain transactions or business interactions, ineffective automation – or too much – reduces essential components of business relationships, making them inauthentic.

Authenticity, in an increasingly networked world, is an essential starting point for the ways in which we design our business interactions. And, admittedly, it's a bit squishy. Ask a neighbor, and she'll be likely to define it as “being yourself” or “a means by which you can establish trust.” Ask an academic, and you're likely to hear a long litany of words like “sincerity” and “irony,” along with their historical underpinnings. Ironically, if we're tracing authenticity's academic lineage, we'll find that it can be manufactured. We'll find that it can be fake. That, sincerely, it can be insincere.

For us, focused as we are on the interactions that drive sales, service, training, and leadership in companies large and small, authenticity happens for others when they know that a person – not a machine – is overseeing a transaction in which they are involved. A machine might help to move that transaction along; a machine might make that transaction more efficient; ultimately, though, in an authentic exchange, a human has oversight.

Bust Up Bias to Build Understanding

Robinson is not the only one who has the market cornered on watching where people are likely to go wrong. The best teachers do the same thing, and seeing it their way can help business professionals to cultivate deep and meaningful relationships.

The best teaching science suggests, as pro forma practice, uncovering flaws in learners' approach to material. It is one of the reasons successful teachers prefer to ask questions, offering plenty of “wait time” before calling on someone, rather than simply lecturing students on a topic.

From a learning science point of view, if you want to help people or change their minds or inspire action in them, you first have to find ways to disrupt their misunderstandings or biases, especially, and most critically, when both seem to be right or when both seem to be, for the most part, working tolerably well.

Here is something counterintuitive. The truth of a discipline is important, but it is nearly impossible to bring students – or clients, colleagues, customers, or managers – to that truth if you are only pointing at it or, worse, pounding them over the head with it with an insistence that the truth is worth knowing. When you are trying to teach people something, and you really want them to understand it, remember this: you learned whatever you're teaching because it became personal for you or stirred up an interest and commitment. Others will only learn it from you if they can access a similar well of motivation – enough to help them sidestep and even overcome their own baked‐in cognitive flaws.

To move a student toward the truth, then, as any good teacher will tell you, you have to be looking at the student, at the person in whom you are trying to build understanding. You cannot just reduce the person to a type; you have to be close to him or her. From educational literature, we recommend the analogy of peering “inside the black box” of understanding (Black & Wiliam, 1998). You need access to the box in order to figure out how to move people to knowledge, skills acquisition, or action.

For example, an effective math teacher knows that a student often has to overcome his or her own certainty. In mathematics, students have to learn to use valid procedures and to understand the concepts that underpin them. Difficulties can arise when students learn strategies that apply only in limited contexts and do not realize that they are inadequate elsewhere.

As such, a skillful teacher relies on one of the oldest technologies know to humankind: the artful question.

Questioning must then be designed to bring out these strategies for discussion and to explore problems in understanding the concepts so that students can grasp the need to change their thinking. (Black, Harrison, Lee, Marshall, & Wiliam, 2004)

Questions help effective math teachers to create space, or intellectual legroom, for a successful learning transaction. Walk across the hall to a science classroom, and you'll see something similar:

There are many features of the natural world for which science provides a “correct” model or explanation. However, outside school, many students acquire different ideas. For example, some students come to believe that animals are living because they move but that trees and flowers are not because they don't. (Black et al., 2004)

In addition to the line of questioning described above, good teachers use two other simple human innovations to break down misconceptions. First, they aim to anticipate “alternative conceptions,” especially ones that have been well documented. Second, they exhibit restraint in working with understanding, which can be delicate:

[More] presentation of the “correct” view has been shown to be ineffective. The task in such cases is to open up discussion of such ideas and then provide feedback that challenges them by introducing new pieces of evidence and argument that support the scientific model. (Black et al., 2004)

Consider a challenge you are likely to face. Perhaps you are stuck in a business transaction wherein you've identified a solution but cannot convince your client or customer to take a step that you feel is in his own best interest. Or, perhaps you've identified a necessary solution during a service visit and you simply cannot convince the customer to act, again in her own best interest. You are stuck – because someone in whom you are trying to build understanding is stuck.

If you want to lead people to the truth, you have some options. Repeatedly telling them the truth, even in an impassioned way, is not as effective as approaching them with a teaching mindset. That is:

• Seeking to understand the broader landscape in which they operate and the other challenges or considerations of importance on their end.
• Analyzing their understanding.
• Noticing any possible misconceptions that might be clouding their judgment.
• Talking with them and asking them questions.
• Meeting them where they are.
• Slowly rebuilding their understanding by giving them targeted feedback and the right information at the right time.

August Van Eepoel, a tax lawyer who has also taught in a variety of settings for several decades, puts it this way:

As to teaching, I soon discovered that covering the material did not produce visible results or participation by the students in a class discussion. I learned to bring a simple, real‐life case to the class, but a case at the lowest level for comprehension by all the students. Thereafter, once discussion began, I could change the case to add complicating facts and allow the discussion to be guided by me to a higher step in comprehension…and then another step. Then, I would discuss with the students one or more possible solutions. (Personal statement, 2018)

Interestingly, he sees a direct through‐line to his work with clients:

Transferring this teaching experience to the business conference room, I learned first to listen to the client, not only to understand his/her concerns and the desired goal(s), but also to gauge his/her knowledge of the legal matter in general, as well as the issues of importance. Using the same classroom process of a step‐by‐step discussion, informed by my client's understanding, I could then layer in a number of other issues to consider, one‐by‐one, to develop a plan or strategy that I would present at the conclusion of the conference. (Personal statement, 2018)

You've heard about the difficulty of making a horse drink once you've led it to water. As Van Eepoel suggests, as the horse handicappers proved earlier in this chapter, and as all good teachers know, the horse is often operating from a flawed understanding of the water (i.e., discipline) with which to begin. Any educator would bet that if the horse understood the water and its benefits, it would not only drink the water but also find its own way there, with or without assistance.

Win‐Win‐Win

If the horse ultimately does drink the water, the horse benefits by being properly hydrated, but the trainer benefits, too, because his or her horse has a chance of performing better. A good horse and a good trainer benefit the context in which both exist, whether that's competitive jumping, racing, or training young riders. We're used to hearing about win‐win scenarios, but this is something different. This is win‐win‐win. A win‐win‐win scenario begins, often enough, with assessment, which is essential to all learning experiences.

When you look up the etymology of the word “assessment,” you may find that it is derived from assidere, which is in turn derived from ad sedere, which in Latin means “to sit near.” The context of “sitting near,” it seems, was that a judge would sit near a citizen to determine the value of a property, business, and so on. The word's meaning evolved from the idea of “sitting near” in order to build understanding. The value judgment that arrived as a result of the proximity was folded into the broader and current definition of “assessment.” Today, assessment, at least in education, is often thought about in terms of evaluation or measurement of learning – but the closeness or context in which the learning takes place is often, and unfortunately, left out of the thinking.

In schools and businesses, an individual's performance is usually measured under some formal assessment or evaluation instrument. Humans, generally speaking, operate comfortably and effectively when they understand the boundaries and expectations in a given situation or set them, collaboratively, in advance. The authority in the situation (a teacher, one's boss, a salesperson) can help both determine the boundaries or expectations and then assess or evaluate an actor's performance within them, amplifying both sides of the experience.

Think back to a spelling test when you were in elementary school. The authority (the teacher) probably gave you a list on Monday of words you needed to memorize by Friday. When Friday came, the teacher probably instructed you to pull out a piece of paper. He or she would then say each word, one‐by‐one (and not necessarily in the order of the original list), with the expectation that you would listen, recall the correct spelling of the word, and write it on the paper. At the end, you would turn in your paper, and maybe the next Monday, you would get it back with an indication of how many words you spelled correctly and how many words you spelled incorrectly. For the incorrect ones, the teacher might indicate the correct spelling.

Merits of this kind of exercise for today's modern, Google‐fluent learner and worker aside, the process itself is completely acceptable. The assessment – the building of mutual understanding of where the individual is within the offered boundaries and expectations and what needs to be done next to operate better within those same boundaries – is sound. If the teacher enters the score into a grade book, and the exercise is done weekly, and so on, even that is acceptable.

But the authority, who has access to that information not only for the one individual, but also for the class as a whole, is able to do much more for the individual, and this is where both educators and businesspeople should take note.

By either detecting patterns in an individual's progress or noticing a trend across the class, effective teachers can elevate the experience of the taught, and in so doing, the experience of the teaching itself (a core tenant of all great teachers is that they want their students to succeed). If all those students do better, the school does better. And not to put too idealistic a gloss on it, but society does better, too, when its students and teachers succeed. Maybe if everyone misspelled the same word (or type of word), the problem isn't with the individuals, but rather with the way in which the concept was taught. A good teacher would not let himself or herself off the hook in this moment. Even something as simple as a weekly spelling quiz would lead a more progressive (better) formative assessor to gear future exercises toward helping both the authority and the actor improve within the context.

The problem is true assessment of learning and progress is very difficult to scale, because only humans are really good at it. Computers might be good at aggregating data, finding correlations and causality that are too difficult for a human being to notice, but that information is best used by a human, who can then apply judgment and intuition – and other immeasurable dimensions – as a lever for someone else's learning. What's more, the human can buy more time and room for humans to reach a mastery that will transform them.

If you're adopting a teacher's mindset, the challenge is to be this good – to assess this well.