Leading Through the Unknown: Reflections from Three Years in a Startup Leadership Role

In the fast-paced world of startups, where change is the only constant, three years can feel like a lifetime. Last week marked the completion of three years in my journey as the Head of HR in my? current company, and it was a milestone that left me pondering the profound transformations I've undergone. This role wasn't just a career progression; it was an adventure into uncharted territory, and the lessons I've learned along the way are worth sharing.

A Little Background:

I've always been a high performer and have learned a lot from each role I have been in, even if at that point, it felt like a bad choice. Most of these roles had been individual in nature, where all I had to focus on was my own deliverables – which are, to be honest, fairly easy to control, right?

Coming back… I took this role as I saw it as an opportunity to apply all I had learned in the last 16 years. It was an opportunity to build something from scratch and take complete responsibility for the good and the bad that came out of it. It helped that the founders and my peers were equally excited about building a place that could provide meaningful careers to employees, a place built on fair and equitable principles; without the baggage of the past and with the promise of building a new future. Honestly, after I had my first chat about this role with one of the founders, I could see myself authoring the sequel to "No Rules Rules" or "Work Rules."

So here I was, joining a young startup with 60 people on September 1, 2020, from the comfort of my home as we were still working from home then. The crypto jargon hit me first, but that was manageable with my super helpful colleagues and my innate ability to grasp new concepts.

A reality check hit me at the first leadership meeting I attended on my second day when my peers asked me to talk about the HR function roadmap, of course with a wishlist of what all they thought we should focus on. That's when it really dawned upon me that I had several people looking up to me to build something concrete.

First Lesson: Defying Visionary Rush

There will always be "expectations of a vision" from you because of the role you are in. It's important not to come under the pressure of reacting, and it's okay to say so when you don't have clarity. Dig deep into what you want to build in the long term, understand what "this" organization needs from your function, and take your time to build a vision that will stand the test of time.

What did I do? I said, "...this is just my second day. I'd like to spend some time with all of you to understand what you want to build, and then I will work on crafting a people's agenda that will help you achieve that goal."

Needless to say, any big role comes with significant responsibility. And mine was to grow the teams "quickly" as we were planning to expand our business. Now, when you are in HR, it's not just enough to hire the right talent but also to create an ecosystem where they feel valued and can thrive. We were yet to answer the question - what kind of company do we want to build? It was also time to start working on meaningful compensation and performance philosophies as we brought more people onboard. And we were yet to build efficient processes that would make work simpler and our ways of working more transparent. I had very ambitious targets for the function, and all had to be done at the right time before we grew too large and it was too late to course correct.

It was time for me to accept that I needed additional hands.

I remember this moment very clearly. We were on an impromptu "work trip" in Goa. About 15 of us had traveled on our own just to get to know each other better. The first morning, we spent some time discussing the HR roadmap, where I could see our hiring goals skyrocketing and the need for us to expedite our function design. I was beginning to get anxious about how I would deliver on these expectations. We all took a break and went back to our respective rooms. I however, went back and knocked on my Founder's door asking if he had 5 minutes. We spent the next 60 minutes standing there discussing how I wanted to start building my HR team and why "just me" would not be enough to achieve what we aspire to.

Second Lesson: Building your Team - the art of timing

Onboard people who know something you don't. Bring them in soon enough when they have meaningful charters and also when they have the time to settle. Craft their onboarding thoughtfully and give them all they would need, and then even more, to excel in their role. Work dedicatedly on building camaraderie among them and tell them they either succeed collectively or don't at all.

Over the next 15 months, we matured our HR team structure, which was just right to manage a group of 600 employees. Yes, we grew 10 times!

What did I get out of it? The collective power of super brains with a diverse set of skills, all working towards the same goal. We took up charters we could deliver well and kept pace with the organization's speed of growth.

Another responsibility that came with this was that I was now responsible for not only my actions but also those of my team members.

Third Lesson: Conquering Decision Overload

One of the primary roles of a leader is to make decisions. The buck stops with us, and for those transitioning into leadership roles for the first time, it can be extremely overwhelming. In most of my earlier roles, my job was to assess a problem statement, figure out various solutions, and give my recommendation. The decision and hence the responsibility were always the leader's to make. This changed overnight when I took up this role. Honestly, it took me some time to come to terms with it.

What helped? Asking the right questions.

How to come up with the right questions? Get a clear understanding of the expected outcome, go back to fundamentals and then ask what can go wrong. One of the mantras I have inherited from one of my past managers is to think of ‘unintended consequences’. Sometimes it can send me into this spree of overthinking, but most of the time, I use my experience and first principles thinking to assess a choice from all angles and then make the right decision based on what I know then.

What about the things that I don't know? Well, be ready to learn from mistakes. It helps to know what is at stake and what's the appetite for failure. Once this is clear, it is simpler to make the decision and move on to the next one.

Fourth Lesson: Getting Over the "My Team" Mentality

As a leader, every team in the company is your own. When you can stop prioritizing your own team's interest over the others, that's when you transition from a manager to a leader and assume the role of a true leader, or as we call it, the "Co-CEO." A management team is nothing but a collective unit of leaders who make decisions in the interest of the company. This is the seed to a collaborative and cohesive culture of 'We Over Me.'

This for sure requires some practice. As humans, we are hardwired to put our family above the rest of the world. As managers, we are trained to fight for our team's interest. When transitioning into a leader, it's this definition that needs to shift from "my team" to "my company."

We've all grown up idolizing the greatest leaders in the world. We have studied the best leadership practices and what has made other companies successful. Somewhere along the line, we all go on to building a strong definition of how it needs to be done.

If there is one lesson that I would keep above every other: Being Yourself

Some of the best moments in which I have enjoyed my time at work, when I chuckled and thought, "I love working here," were my own goofy moments: when I was me. The word leader weighs heavily on many of us, and we try to adapt to what is expected. But history is made only when we challenge the status quo. So kick that imposter syndrome out of the window, know that you are here because you deserve it, and bring yourself to work, just the way you are, and not as who you need to be.