In order to effectively scale as an executive, at some point you must hire a team of people who know things you don’t. Once your team has capabilities outside your area, you still need to effectively help, teach, and coach them in the areas outside your expertise. This can be especially difficult in technical areas where they may be literally speaking a different (programming) language than you. How can you develop your team in areas where their knowledge already exceeds your own? Finding and encouraging the use of training materials is one option, but how can you, as their leader, contribute to their development?

When you reach the point of needing to develop someone’s capabilities beyond your own expertise, the material in question is surely advanced. The most time-honored means of teaching complex material is the Socratic method. To utilize this method, a teacher assigns a complex reading he or she already understands well, feigns ignorance, and asks questions of the students. Follow-up questions then deliberately lead the students down the right path to fully exploring the question and determining for themselves the answer.

The Socratic method requires a teacher who understands the answer but pretends not to, who then asks leading questions until the other person also discovers the answer. That’s a great approach for law school and similar settings, but it doesn’t quite fit what we need to do here. Still, it sets a good example. How can we build on that example and make it more relevant for executives who need to teach something they don’t know?

The approach I use for developing people in areas outside my own ability or knowledge is what I call the “Double-Blind Socratic method.” In the Double-Blind Socratic method neither the teacher nor the student knows the answer, and the teacher asks questions of the student until both teacher and student have found the answer. If you’re the teacher, the challenge is in figuring out how to ask leading questions when you don’t know the answer you’re trying to lead someone toward.

Become the Student

To start, you need to confirm the person you’re attempting to teach has enough baseline knowledge to be able to get to a solution. I’ve long been a proponent of the idea that until you can explain something clearly and simply, you don’t understand it. A quick litmus test for this is: can you teach this effectively to a reasonably intelligent adult with no expertise in this area? More challenging, can you teach this to a 10-year-old?

In this scenario, you’re the reasonably intelligent adult who lacks domain expertise, so have them teach you the basics. This has three advantages. First, it forces them to refine their own thinking. Second, it introduces you to the building blocks of the domain in question. Third, it gives you a good idea of which elements this person understands well enough to teach you.

Thus, the first step to teaching someone something you don’t know is to have them teach you. Any time one person teaches something to another, the teacher must first re-teach themselves when designing their lesson. In this case, by asking your team member to teach you, you are covertly getting them to teach themselves.

The real skill here is in getting them to teach you what you need to know in order for you to determine whether they’re teaching themselves what they need to learn. You need to be able to learn what they’re teaching you while simultaneously applying that new knowledge to evaluate their knowledge of what they’re teaching you.

Define the Building Blocks

To get anywhere with this, you’ll need to learn what the building blocks are in this domain. By building blocks, I’m referring to the rules of the game and the elements from which everything else builds. Depending on the nature of the problem, the relevant building blocks can be down to minute details, or they can be larger conceptual elements.

Most people will not naturally teach or explain a complex topic in terms of building blocks. You need to ask clarifying and critical questions to get them to refine their teaching to a point of clearly specifying the relevant elements and rules of the game. When you develop the ability to do this artfully, you can help others impose order on and gain clarity from their own existing thoughts.

Next, you get to start questioning things. You can question their underlying premises, and you can ask about ways of assembling the building blocks you just learned about. When you ask probing questions about the building blocks you’ve identified and defined, and add questions about combinations of them, you get simplistic explanations of what is and is not possible. If you continue to do this over time, the repository of explanations you build up gives you a strong level of understanding of an area even though you still lack the detailed knowledge it would take to do the work yourself.

Propose new arrangements

Have them teach you what would happen if the building blocks were put together in ways you haven’t seen or heard of yet. This forces the student into higher-level thinking, where they now need to understand the fundamentals not just well enough to teach them to you, but to also extrapolate from them into new territory. Through repetition, you can develop the ability to tell how well someone understands what they’re teaching you, while also gaining the knowledge you need to ask more pointed questions each subsequent time.

It’s possible, once you become good at this approach, to help someone identify solutions they’d never have thought of on their own. Use the knowledge and insight you build up from continually asking these things to combine multiple building blocks in novel combinations no one’s asked about before. Your 10-year-old innocence in playing with these building blocks means you’re likely to propose impossible combinations. That’s ok, as not all “impossible” combinations are bad proposals, and your willingness to explore the impossible gives you the freedom to explore combinations others wouldn’t consider.

The fool didn’t know it was impossible, so he did it.

Mark Twain (apocryphal)

Practice this approach enough, and your willingness to ask foolish questions will pay off when you accomplish the impossible.

Ask Follow-up Questions that make you a good “Rubber Duck”

Even if you aren’t willing to risk being a fool who asks about the impossible, you can still become an incredibly effective and more general-purpose “rubber duck.” Rubber duck debugging is a term used by programmers to describe the practice of explaining their code line-by-line to an inanimate object- traditionally, a rubber duck. This forces them to think through details they’d otherwise gloss over, and it often reveals to them what isn’t designed right or isn’t working the way it should. Unlike a rubber duck, you get to ask insightful follow-up questions. You also get to initiate the process, which means you can use it for teaching all sorts of things rather than reserving it only for diagnosing known problems.

In the last Analytics team I built, my “rubber duck” abilities reached the point of a running joke. When someone was having a difficult time getting a particular query or model to work, they’d call me over to stand near them. My proximity became enough for them to internally trigger the questions they expected me to ask, and in many cases answering my unasked questions was all they needed to get past their hurdle.

Shift the Conversation Up or Down in Levels of Abstraction as Needed

The Double-Blind Socratic method uses targeted questioning to break complex things down to base components and re-assemble them in useful ways. These questions can force rapid movement up or down in levels of abstraction, giving the student new perspectives of their own knowledge. Each of these perspectives can be valuable.

Shift Down to Re-examine the Building Blocks

The purpose of bringing someone down one or more levels of abstraction is to get them to reconsider whether they’ve truly identified the relevant base-level building blocks. The candle problem is a famous cognitive performance test that directly demonstrates the benefit of thinking at a lower level of detail than someone may default to.

The candle problem is straightforward. You must fasten a candle to a corkboard on the wall above a table in such a way that the wax melt from the candle won’t drip onto the table. The only materials available to you are the candle, a book of matches, and a box of thumbtacks.

The solution that a surprising portion of people miss is to empty out the thumbtack box, use some thumbtacks to fasten the box to the cork board, and set the candle in the box. The mental blocker in finding this solution is that many people fail to recognize the box as an item separate from the tacks. This tendency is called functional fixedness. We are so used to knowing what things are normally used for that we forget what they can be used for.

I mentioned earlier the importance of gaining a 10-year-old’s understanding of the world. When dropping down a level of abstraction to address functional fixedness blockers, you may actually want to target a 5-year-old’s understanding. In one study, 5-year-olds were shown to perform demonstrably better than 6- or 7-year-olds on the candle problem, because they were much more likely to identify the box as an independent item. They hadn’t yet formed the mental habit of abstracting a box of tacks as a way of referring to a rough quantity of tacks. To them, it was a box that also had tacks in it.

When helping someone in an area where your own understanding is still limited, take advantage of your naivete and give them the benefit of perspective a 5-year-old would. Ask what things are made of until you’ve found any hidden potentially useful pieces. If you continually practice with this, you can actually increase your neuroplasticity and increase the rate at which you learn going forward.

Shift Up to See the Big Picture

Bringing students’ thoughts up to higher levels of abstraction is helpful when you suspect they’re failing to see the forest through the trees. When working on a difficult or complex problem, it’s common to get so engrossed in attempting to solve it that you forget what the actual problem is in the first place. Imagine someone struggling to get a horse and its rider through a thicket or past a guarded area. How would you advise them? What if they had simply forgotten they were playing chess and that in chess knights can jump?

My favorite example of this is of a time when I was the student failing to see the big picture. I was struggling with the model in my thesis, and I’d exhausted my ability to dig deeper into the math and find my error. I had various forms of the equation scribbled in dry erase marker on windows, mirrors, and even the shower door, and none of the approaches illuminated what was wrong. The standard theoretical model seemed correct in every way, except for the pesky fact that it didn’t at all reflect the real-world data.

I called my wife to talk through my frustration, and she very calmly asked me what the assignment was. I started to explain the theory behind the model, and she patiently asked again what the assignment was. I told her it was to write my thesis paper, then started off again on the model. She stopped me and pointed out that I was right- the assignment was to write a paper. So, why not write a paper, but on the reasons why the theoretical model wasn’t matching the data, rather than on why the model was right?

The idea seemed preposterous. To turn my thesis around in its final moments and write a paper arguing against it seemed insane. Out of options, I tried it anyway. In writing the paper with that new perspective, I was able to discern why the model didn’t reflect the real-world data. From there, I was able to write a paper that proved that hypothesis and went on to propose an enhanced version of the model that resolved the issue and did reflect real-world data.

One example in the workplace was even more absurd. An incredibly bright employee was building a forecasting model, and he’d run into an issue he couldn’t solve. He needed two parameters in his model to be equal to each other. He had solved one of them, and he was stuck trying multiple alternate approaches to solve for the other. He was looking for help with one potential solution when I asked why he couldn’t simply set the second parameter to equal the first one, rather than solving for it at all. He started to mention circular logic, stopped, made a face, and tried what I asked. The model worked instantly. In his earlier iterations of the model, the way those parameters had been set up would have made my suggestion impossible. Because of that, he hadn’t considered that in his new model it was not impossible.

The Double-Blind Socratic Method

1. Have the student teach you. Identify and question gaps in their teaching.
2. Define the “building blocks”.
3. Propose new arrangements. Be open to being wrong or proposing the impossible.
4. Ask follow-up questions that make you a good “rubber duck”.
5. Shift the conversation up or down in levels of abstraction as needed.

The Double-Blind Socratic method allows you to teach someone about areas that they already know better than you do, by asking them questions. Leaders in every organization can benefit from this approach. Even if you didn’t intentionally build a team capable of doing things you can’t do, just about every team has the need to do things outside the reach of what the leader can do alone. When you pair this teaching method with your own openness to being wrong, you can refine your critical thinking skills, streamline your questioning, and increase the rate at which both you and your team learn. You can provide value-add leadership to people who know more than you.