The Paradox of Leadership

Vinita Gupta
5 min readJul 17, 2024

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It’s not about standing out but standing in

When I was in 5th-6th grade, my mother once said to me, “You do Netagiri in school.” She meant, in a slightly insulting way, that I tried to be the leader of the pack and win influence. Neta, in my mother tongue, Hindi, means leader. I used to do stupid things to win the admiration of my classmates. In 6th grade, I imitated our math teacher onstage during a school function. My classmates admired my guts and thought I was funny. Not surprisingly, my teacher was offended.

Thankfully, I outgrew some of the childish things that I did back then. In retrospect, this might have been my first lesson in leadership studies. Little did my mother know that I would one day become the first woman of color to take a company public on NASDAQ. Little did I know that my skills as a leader would become essential for my entrepreneurial success. Along the way, I learned a lot about leadership — much of it counterintuitive.

Ironically, I didn’t even realize I was studying leadership until well after I was a CEO. And that may have been a key to my success. Because true leadership must be genuine and from the heart. It cannot be planned or put up on stage when necessary, turned on and off in different situations. The best leaders have the qualities that make them great leaders deeply embedded in their way of being.

So, I think the first lesson of leadership I learned was to don’t think of it as leadership. Think of it as studying situations and reacting in the way that makes the most sense to you. The question often asked about leadership is whether it’s innate — you are born with it — or learned through practice. I say neither and both.

Overthinking Leadership

There is something of a cult of leadership in business, with executive coaches charging $1000 an hour. Most of the time, those coaches have never taken a company public, and many have never held an operational role in a fast-growing firm. Yet executives obsess over leadership. I remember when, just after hiring the full executive team at my company, one of them said about another vice president, “He does not demonstrate leadership.”

It was an honest comment; truthfully, I did not know then what he meant. I told him so. He did not explain, perhaps out of courtesy. Or perhaps he was thinking I was being modest or trying to avoid the issue. What he never could have known was that his CEO did not explicitly think of leadership as a definitive quality. He could not have imagined that the founder, the CEO of a company about to go public, was so naive. That brief comment awakened me, and I started a long journey of trying to understand what leadership means. It’s a journey I am still on.

What Does Leadership Really Mean?

In the modern business environment, a leader has to make things happen through others and produce results. But this is not as simple as winning over followers, like a preacher giving a church sermon. A leader must communicate the vision and instill the passion but also recognize, with humility, that maybe their employees have a better way to achieve the goal. When appropriate, a leader must follow. Also important, when appropriate, a leader must course correct their team when discord emerges of things go off the rails. There are no set rules. Leading is both from the gut and from recognizing patterns — learning, in other words.

Building a successful business also requires leaders who are great thinkers and can generate creative solutions and ideas. Sometimes, great thinkers have an easier time motivating people because they can more easily earn admiration. If you start a company, being a clear, compelling thinker, especially when the going gets tough, is essential. In the early days, you are selling merely your idea and then steps of success, nothing else.

Many people admire the conviction to take a leap based on your vision, and it can draw like-minded followers. In my case, at my farewell lunch, after I had quit my job at BNR, I could tell that I had won the admiration of my co-workers. This gave me confidence that I could win the admiration of others when I needed them to invest in my company and my vision, either by working for me or providing capital.

Other leadership qualities that build loyalty are as simple as the Golden Rule. Employees like you because you treat them with respect. They also like you if you are not afraid to call them on the carpet and demand performance. In my experience, high performers prefer this. But it only works if you demand that from yourself, too.

The Never-Ending Journey

Leadership is a journey that is never over. You must always be experimenting and you will make mistakes. My correction and experimentation with my leadership style were sometimes too timid. This gave my employees the feeling that they did not have to listen to me. Other times, I expected too much from them, and people left. I once initiated incentive bonuses to engineers for on-time completion. That did not work well because they still missed the deadlines and had worked much harder. That irritated them, and many started leaving the company. In principle, my tactic should have worked. In reality, in my company and in the culture we all created, it didn’t work at all.

A startup leader has to be a great thinker. At Digital Link, one time, we had to present a proposal to Boeing, one of our large customers. My VP of Engineering drew a solution that looked complicated to me. I diagramed a simpler solution and asked if my version would work. He was skeptical at that moment. The next day, he came to my office and said that, upon reflection, my proposed solution was better than what he had suggested. He further added, “I don’t know what I was thinking.” My admiration for him went through the roof. The only thing I remember from that incident was how can I be like him. Learning from what you admire in others can be a powerful way to evolve as a leader.

Counterintuitively, true leadership is not about fitting into a pre-defined role or possessing certain traits. It’s not about having a coach or learning specific methods. It’s about studying people and constantly tuning in.

https://guptavinita.com/

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Vinita Gupta

Tech Entrepreneur, Business Woman, Writer/Journalist, National Bridge Champion