Here’s a classic mistake newbie professionals, as well as newbies at adulthood, often make: when people ask them silly, stupid or minor questions, they assume that those people are silly, stupid, or minor. And let’s be frank: almost all questions you receive are silly, stupid, or minor, right?
But there’s an open secret that is worth not being a secret: it’s only a good thing—a very good thing—for you to assume that there is a good and important reason why those silly, stupid, or minor questions are being asked in the first place.
Let’s take an example as simple as just chatting with a taxi driver. When I get into a taxi and tell him where I want to go, the taxi driver, almost always (and always in my hometown of New York) asks me if I have a preferred route. I always thought it was a stupid question. “You’re the professional driver, and you spend your whole days driving around the city, not me! Why are you asking me? As a professional, you should know better than me where to go!” Until an article I read long ago—Ba’al only knows where that link is—that explained why this is considered to be a best practice among New York City taxi drivers. The reason is that the vast majority of people going on taxi rides are people going to their home or their office. Both of those are routes which the passenger takes constantly and thus knows inside out, including the amount of traffic they usually encounter—and therefore has strong opinions as to which route has the most or the least traffic. As a result, it’s a very common situation for a taxi driver to take a passenger onto a route that the passenger knows well, but the taxi driver happens to chooses a different version of the route than the passenger’s preferred route (the driver goes down this street, not that one) while the passenger (preferring his favorite route) gets angry at the driver for taking a “purposefully slow” route, accusing the driver of going on a stroll to rack up the meter and charge the passenger more—and thus the likelihood of a tip for the driver is decreased and the likelihood of a stressful fight, possibly even resulting in the passenger not paying, is increased. As such, it’s a New York taxi driver’s best practice to just ask the passenger if he has a preferred route to avoid any such risks.
But the key—and most interesting—point is: the taxi driver’s route is often faster and better than the passenger’s preferred route! Your preferred route is the one that you think and feel is better, but it may not be. The passenger hasn’t analyzed whether his preferred route is exactly faster or not, and he certainly didn’t do a real-time analysis to see which the best route is at that particular moment. It’s just his preferred route that in his heart he thinks is the best one. And from the taxi driver’s point of view, he just wants to make the passenger happy, have a smooth ride, and hope to get that tip. Not worth fighting over the optimal route. As a result, just asking the passenger for his preferred route and following it is a win-win (even if in many cases it will be the slightly slower route).
In other words, the taxi driver knows something you don’t. In particular, he has a theory of client management he is following in his head when he asks that question. So even on this simple level, always remember: there may be a motive behind their question beyond mere silliness or stupidity. That motive may not be Machiavellian scheming, perhaps it is just a different interaction model with others or some assumption they have that you don’t.
This insight applies deeply to professional interactions. Just out of college, I once had an interview in which the interviewer looked out onto the river from the fancy office on the top of the tower (it was the Hudson River, beside Manhattan) and he observed the company had another office on the other side of the “Kearney River”. I thought he made a mistake or was a bit stupid but only 20 years later, a memory sparked that interview and I realized that it was a test of whether I would correct him when he was wrong, or not.
Now, I do the same when I work with people. I’ll often write or say ridiculous things to see if it raises a red flag. That’s a good sign because it will tell me that if there is a real situation in which I need them to correct me when I’m wrong, how likely they are to do so.
It also shows if the people you work with have done their work or not. Remember the classic Van Halen concert contracts that snuck in a tiny clause about removing brown M&M’s in a bowl in their backstage, so that when the band arrives, they’ll immediately know if the contract has been read or not. That’s an instantaneous sign as to whether they’re paying attention to all the other little details—the ones that matter.
And if I’m doing this when we talk, and the taxi drivers also are… wouldn’t it make sense for those who have much more at stake than I do—that is, your client—to do the same? Perhaps even without realizing it, they are.
The generalized pattern here is to assume that every question is a test, and there is always a purpose behind it. All intelligence operations start with the assumption that “there are no coincidences” and it’s a useful assumption to keep in mind—even in terms of the randomness of the ridiculous questions people ask you. Or lack of randomness in them, as the case may be.
