Believe In You

In the last few years, I have come to identify myself as the “reluctant leader.”

The reluctant leader is not someone who goes seeking positions of power. Those positions have found me, time after time, even when I wasn’t looking for them. It started as early as high school, and it has only continued as a persistently annoying theme in my life. I don’t seek, covet, or hunger for power. Instead, it is the knowledge that I can bring something needed to the table that has propelled me upward and into positions of power, despite my reluctance. I know many managers and leaders actively seek power, mostly because I have observed it while being grouped together with other leaders at schools, companies, and teams through the years. I have worked in technology, design, publishing, retail, and food service. I have been able to jump from industry to industry because I embody qualities of a leader that are usually in short supply: listening to others, humility, and imagination. I stand apart, the reluctant leader, who has always begrudgingly accepted the challenge of leading.

In every new leadership role I take on, I learn something new. But the piece of advice that remains vitally relevant is a question that was posed to me by a mentor early on in my technology career: why not you?

I was taking on a new role within the company I worked for at the time, and the product I was asked to develop was a larger, more public-facing, and more intimidating task than I had ever taken on before. I had always been the odd duck in the ranks of the product managers at that particular startup: the one without a CS degree, the one who relentlessly referenced pop culture, and the one who put design at the center of every product challenge. I had experienced slow and steady wins over the course of a few years, but I thought my boss had made a mistake in naming me the new PM for our new product initiative. He must have made a mistake right? Why me?

I always had particularly open dialogue with this boss, so I brought my concerns to him. We tucked ourselves into one of those notoriously yellow, badly lit, and cramped conference rooms that is the hallmark of far too many office complexes.  I asked simply, “Why me?”

What I wanted him to do was tell me how fantastic he thought I was. How nobody could do the job but me. I waited impatiently for him to regale me with the thousand ways he thought I rocked.

But he didn’t.

Instead, he just calmly looked over the top of his glasses and asked, “Why not you?”

I sputtered, and backtracked, and pondered. It was an okay meeting. But the advice was something I would carry with me to this day.

Why not me? My lack of confidence, my inability to see my own talents, and my insistent reluctance was not his problem. It was my problem. I had to deal with it. I had to look it full in the face and grow from it.

And I had to learn to answer “why me?” to my biggest critic: myself.

He had already chosen me. He saw something in me, and given me opportunities, praised me when it was merited, and course corrected me when I strayed too far. I grew with him and showed him forward progress with ever increasing speed.

But I was plagued with self doubt. I doubted myself every step of the way. We are psychologically wired to forget ten compliments while holding on to that one criticism. It is hard not to be hard on ourselves, or to forget when others have treated us poorly. This has become an epidemic in Silicon Valley, where the “imposter syndrome” runs rampant. People who think they aren’t good enough are plagued with crippling anxiety, sometimes to the point of leaving their job altogether.

Looking at it a little differently, the question “Why not you?” could easily be expanded to, “Why don’t you believe in yourself?” This root principle is at the heart of any act of self-sabotage, the hundreds of doubts that can make you question your work every day, and prevent you from bringing your best, authentic self to your work. No one is going to believe in you for you. That is your solely your responsibility. And very often we forget to believe in ourselves. To cheer ourselves on. To own the situation we find ourselves in. To simply believe in the self.

I spoke with my new team recently--PMs full of promise and anxious to cut their teeth on challenging new projects. We had worked diligently together for months, training and educating in new ways, and I am excited about what is next for them. But I sensed they didn’t feel they were quite ready. What about more training? What about more education? What if we don’t do well enough? What if it isn’t enough?

What if?

The what ifs don’t matter to me. There will always be what ifs, and no matter how diligently you prepare, that feeling of not being ready doesn’t go away. Because it isn’t how much you’ve done, it is how much you believe, especially in yourself. What I told them was that what matters to me is that you try. That you give your best. That you learn. That you stay present. That you keep pushing yourself. Because you will never be ready if you add up all the ways you aren’t ready.

Instead, you must add up all the ways you are ready. And celebrate those qualities. Wear those positive qualities like a coat of armor.

The reluctant leader is ultimately someone who does not know their own strength. This is good because they don’t lead from a place of ego, or their perception of how great they are. Instead, they lead from another place. It is a place of humility, a place of service, and a desire to genuinely help others. Reluctant leaders are rare, and valuable, as they can help transform teams and companies. They disrupt peoples’ perceptions of what leaders are, and what a leader can look like, and how a leader can behave. They go about their day-to-day, trying to help and make things better, and tend to touch a lot of different dimensions of a company as a result. People take notice.

Essentially, the reluctant leader is a leader of the heart. One who knows the answer to the question: why not you? But who will never answer the question for you.

That is the journey you must make yourself.