An Achilles Heel for Leaders in Tech Startups

Jack of None Master of One

Most people perform at least one thing well. Some people are good at many things. Few people perform exceptionally at many things. No one is exceptional at everything. Whichever of these categories we fall into has to do with the diligence we have applied in learning skills and the depth of knowledge required in order to master a given skill.

When I think about the various degrees of mastery people have over certain skills, my youngest daughter comes to mind. When she was about eight-weeks old, a pediatrician detected a faint heart murmur. After being referred to a pediatric cardiologist, it was discovered that she had a number of large holes in her heart that would require surgery in order to repair. As my wife and I nervously awaited the day that our infant child would undergo an open-heart operation, we met with the surgeon. The surgeon was a calm man who exuded confidence. He explained that during the operation, my daughter’s heart would be stopped temporarily and she would be placed on a heart-lung machine that would provide the necessary oxygen to her blood. He then told us that after patching her heart, he would remove her from the heart-lung machine and return the flow of blood to her heart, at which point her heart would begin to beat on its own again. I was in awe of this man’s abilities. The surgeon assured us that our daughter would be fine, and indeed she was.

The surgeon, who was probably in his 50s, had performed hundreds of surgeries during his career and was clearly exceptionally good at his job. One of the lessons I took from that experience was that for all the years this competent surgeon had spent honing his skills and perfecting his craft, had my daughter been afflicted with perhaps an injury to her brain, he would have been incompetent to perform brain surgery on her. In other words, even very minor degrees of variance in terms of the skills required for a task can render an otherwise exceptionally skilled person at best mostly incompetent, and at worst totally useless.

The Humility Factor

Since at least the Age of Enlightenment, the amount of knowledge available has continued to grow exponentially. The ever-increasing amount of knowledge has necessitated that individuals spend many years studying and practicing some skills in order to be proficient at them. For example, while they certainly share some common knowledge, a chemical engineer and a mechanical engineer could likely not do each other’s jobs. There is nothing especially revelatory about this. What is important, however, is how this factor plays out in organizations where a multitude of different skills are required at an exceptional level of expertise in order to produce products and services. This is especially salient for tech startups.

Having worked in five different startup organizations over 14 years, I’ve observed firsthand how this need to have different people exceptionally skilled across a number of fields has the potential to play out for good and bad in the context of decisions made by leaders. A leader cannot be expected to be an expert in all fields over which he/she has responsibility. So how can leaders in tech startups be effective when they maybe know little or nothing about all the skills of those whom they lead? Mercifully, the answer is not complicated and is something that a leader can develop­–humility. The cultural narrative in the West tells us that leaders are strong, decisive, knowledgeable people. The concept of humility seems, on its face, to be incompatible with the above-described shape of a leader. And yet, in order for leaders to be effective, especially in tech startups, I submit that humility is an absolute prerequisite. Humility is often interpreted as being analogous to inferiority and weakness. But in my experience, if properly practiced, humility is often perceived as a strength.

Finding the Sweet Spot

I once worked in an organization with a leader for whom I have deep affection. Never before and never since have I met such a kind and humble man. But his kindness and humility manifest as indecisiveness that made him appear weak and opened him up to being manipulated. To be fair, this man never asked to be in a leadership position and it was more or less thrust upon him. But the point remains that his constant wavering with every bit of new information did not serve to help him make better decisions, which undermined his authority, and he was perceived as weak.

On the other end of the spectrum, I later worked in a tech startup with exceptionally skilled people in a variety of fields, where the leadership­–who did not have the depth of technical acumen of their subordinates—were totally impervious to input from the individuals with technical expertise about the products and services the organization was producing. The leadership made decisions in a bubble, and their behavior was perceived as arrogant. Of the two scenarios—i.e. the weak leader and the group of arrogant leaders—the latter was far more corrosive to the organization. I do understand the group of seemingly arrogant leaders; they were leading people who were extraordinarily intelligent, skilled, and experienced. These individuals likely calculated that in leading such a group of people, they would need to be the prototype of the Western leader—strong, omniscient, and decisive. This fear-based response was the worst thing they could have done.

Their arrogant behavior left in its wake a deep disrespect for them and their decisions, low morale, cynicism, attrition—things that startups cannot easily absorb—and the ultimate demise of the organization. To be sure, these leaders were not bad people. Good people can be very bad leaders. They were simply listening to their fear that if they did not appear smarter, wiser, and more capable, that they would be disrespected, when paradoxically the opposite was true.

So where is the sweet spot between behaving in a way that causes you to be disrespected because you overly vacillate and capitulate and being disrespected because you puff yourself up with pride and behave as omniscient beings? The answer lies in the simple concept of authentic curiosity. Why authentic? It’s not about being curious for the sake of being curious, and it’s not about feigning curiosity. It’s about coming to terms with the simple fact that even a heart surgeon, with years of training and practice, and decades of experience, need only take one slight step to the left or right of his highly refined skills to find himself incompetent. I don’t mean incompetent in a pejorative way. I simply mean that he would lack the competency to perform tasks even marginally outside of his skillset.


Ultimately, genuine curiosity is about self-knowing—having an accurate confidence in what you know, an acceptance of what you don’t, and a willingness to be vulnerable by being constantly curious about the things you don’t know that should factor into the decisions you make as a leader. Being authentically curious does not mean punting on hard decisions; it means opening your mind to the knowledge and wisdom of those whom you lead so that you can use your judgement to make informed decisions.

This mindset of genuine curiosity is essential in leading today’s workforce of exceptionally skilled individuals across myriad disciplines. Leaders who display genuine curiosity will find themselves respected and followed, despite the little voice inside their heads that insists omniscience is the path to respect. As leaders, seek first to understand. To put yourself in a frame of mind to do this, be humble and let that humility manifest as authentic curiosity, so that your decisions will lead your organizations to higher levels of profitability, productivity, innovation, and competitiveness.