On knowing

When I was a senior in high school, a teacher asked me to join the impromtou speaking team. In this competitive speech event, you received a question from a predefined category–for the category “transportation”, it might be something like “Should seatbelts be mandatory?”–and had just 6 minutes to prepare and deliver a speech on it. I had previously acted in drama events, and even improv comedy, but never spoken seriously without preparation.

The first time I tried it, alone with the teacher, I nearly cried. Standing in front of the room, I stumbled through a few points loosely related to the question, forgot to express an opinion, and trailed off to silence after only a minute or two. Undeterred by my failure, my teacher showed me a few tricks to help connect my thoughts and pace my speech better. After a lot of practice and a few competitions, I began to feel more comfortable and deliver better responses. Eventually I made it to the state finals, alongside competition who had much more experience than me.

The most interesting thing I learned from my impromptou experience was the power of nonsense spoken with conviction. I found that with just 5-10 unique stories or data points on a category (e.g. “transportation”), I could string together a compelling argument for almost any question. It wasn’t important that I believed what I was saying, or even that my arguments were consistent across questions. In fact, I would frequently use a single anecdote or data point multiple times in a single day to argue completely opposite things–and as the judges were different for each question, my shifting opinions were no problem. The important thing was that what you said sounded believable on the first pass, which was influenced as much by how you said it as what you said. My bar for “knowing” something was lowered to pass anything that received superficial approval and sounded confident.

As you might expect, this taught exactly the wrong lessons to a self-centered and overconfident teenage boy, which I’ve spent years painfully unlearning in the real world. As I progressed through university and various jobs, working on increasingly difficult and complex topics, it became clear that falsely knowing–and acting as such–was a liability, not an advantage. My polished speaking skills, and the belief in my own ability to spin believable solutions out of thin air, combined to set me up for a bigger fall when I encountered situations I wasn’t actually prepared for. The questions I worked on now demanded real, not postured, solutions, and the critiques I received were not from sympathetic teachers at weekend student events, but from brilliant and exceedingly logical friends, mentors, and colleagues searching relentlessly for the truth.

This problem actually gets worse as you gain experience. It’s natural to believe that your years of experience have given you an instinct for “what works” and what doesn’t; that because you’ve been around for a while you can skip some of that boring background work. But in a rapidly-changing world–and anything worth working on seems to be “rapidly-changing”–the facts themselves are shifting so fast that prior experience can also be a handicap. The more you learned on the last project, the more you need to unlearn on the next. It’s the cognitive equivalent of the Innovator’s Dilemma: as soon as you get good at something, it becomes useless and your investment in it becomes a burden.

What’s the alternative to this? For me, the solutions have all involved humility and patience: learning to say “I don’t know”; asking for advice; listening more than I speak. Practicing mindfulness through reflection and meditation, to recognize when things have changed and require new approaches. Recognizing that knowing takes time, especially when you’re experienced, and planning extra time to figure things out.

People often think leadership is about personality; that no one knows the right answer, and that you just need to act like you do. Steve Jobs said early in his career, “Pretend to be completely in control and people will assume that you are.” With his recent geek-beatification, people are taking this statement as gospel, and acting confident despite not knowing a thing. I’ve personally watched an entire generation of product managers and designers turn into wannabe-Pied-Pipers based on this advice.

But that’s exactly the wrong lesson to learn from Steve’s work. Instead, look at what he actually did–continually disrupt his own past successes. Apple under Steve Jobs was a place that repeatedly cancelled successful products and replaced them with new ones; Steve himself would make outrageously opinionated statements about product features and then completely change his mind with the next generation. In some cases this may have been calculated misinformation, but in others he clearly made an about-face on something he had strongly believed.

Don’t act like you know when you don’t. It’s ok to not know right now. Wait and work until you do know, and recognize that what you knew yesterday may be holding you back today.