I was asked to give a commencement speech to an MBA class, and it made me think back about all the decision points in my career, and what guided me that I could share with these students at the start of their careers. I landed on an operating principle that evolved for me over time. Early in my career, I was pretty naive, and there were a lot of things I knew I did not know, and even more things I did not even realize were holes in my knowledge. I cofounded a software company while I was still in graduate school, and we barely knew enough to make a go of it. We relied on guidance from a couple of professors, and the kindness of our accountants and lawyers to help us muddle through.
Eventually, we sold the business to a small public company, and I ended up in a somewhat senior-level role working for an experienced entrepreneur who had also sold his business to the same company. About that time, I started to develop the operating principle I shared with the graduates. Coming from a tiny venture-backed company into a small, but established, public company, I was suddenly faced with all sorts of policies and procedures and rules that were totally foreign to me. I constantly heard “we do it this way,” or if I asked a question about some procedure, the answer was “that is just the way we have always done it.” A lot of things seemed set in stone, even though the market and the tech industry were changing very rapidly at the time.
Our tiny startup company was attractive to the much larger company because we were part of the new wave of tech, and the older company said it wanted to adopt what we were doing to help it shift its business. The reality was ‘the way things had always been done’ carried a lot of inertia. Like a giant cruise ship, the business resisted changing direction. I found myself constantly asking why the business did things the way it did. Fortunately, I was working for another ‘outsider’ whose business was acquired for similar reasons. My questions were at least heard, and we could commiserate about the slow moving bureaucracy of the larger business.
What I was learning was that ‘the way we have always done things’ is not a good enough reason to continue to do the same. One of my favorite examples that lasted for decades until someone questioned the premise, was the way the army staffed a cannon. There were always four people assigned to staff a cannon. One person cleaned the barrel, one loaded the projectile, and one fired the cannon. For decades, nobody asked why there were four people? Finally, someone questioned the practice and researched the history of ‘the way we do it.’ The answer was simple: The role of the fourth person was to hold the reigns of the horses. Times evolved to eliminate the use of horses, but ‘the way we do it’ had not evolved to eliminate the fourth person. It took someone to question the premise in order to bring about an obvious change.
I began to develop a practice of questioning the premise whenever someone told me ‘how things worked.’ The concept of always questioning the premise grew into a deep rooted principle for me. It opened my entrepreneurial thinking to be more creative about looking at markets and products and thinking about ways to disrupt the status quo. It led me to become much more skeptical of projections and forecasts, which helped me to become more analytical. Questioning the premise means holding others accountable to fully support their positions, rather than blindly taking their word for it. Questioning the premise does not mean becoming a jerk or just a skeptic. You can question the premise in a positive manner, and actually use the process to foster deeper understanding or brainstorm alternatives. Questioning the premise is often an exercise of curiosity. It can start by saying “help me understand…” One lesson I learned was that starting with “why?” Typically fosters defensiveness, but active listening and asking for clarity or depth drives engagement.
From a personal career perspective, it fostered introspection. Questioning my own choices helped me avoid career traps, and gave me the confidence to question any premise that is standing in the way of achieving my goals. What I told these graduates was not to let anyone, including themselves, put them in a box as their careers progressed. Question the premise of the box. When someone explains the limits that define the box, question why the limits exist, and do not simply accept ‘this is how we do it’ as a valid answer.