What I learned working for a boss 16 years younger than me

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It was sometime in December 2013, after Moody’s acquisition of AMBA (the startup I worked for) was a done deal, that I began evaluating options. I was 48 years old.

Working for a large company wasn’t a choice; I was too much in love with startups. While I was contemplating my next move, I was introduced to Raghu, the 32-year-old founder of Taxi For Sure (TFS), a taxi aggregator like Uber.

While I had always loved working with youngsters, working for a much younger boss would have been a first time experience.

Though I had heard very good things about TFS and Raghu, I did have some concerns working for someone who was 16 years younger than me! I went to the meeting with an open mind. The meeting was interesting. He told me everything that TFS was trying to do. After a short game of brain tennis on the industry and the startup ecosystem, he told me, “I have heard of you and I don’t know if I am competent to interview you. We would be delighted if you’d join us and help us accelerate our journey.”

Obviously, the short conversation was the interview but I liked the way he put it. I was there in the TFS office at 8 am the next morning. For the next 12 months, until TFS’s merger with Olacabs, I was there in the office every day at 8 am.

Here are some of the lessons I learned during the 12 most exciting months of my professional life:

Age is a strength and a weakness

Age equips you with knowledge of the common points of failure, but it also numbs you to the fact that each situation is unique and the mode of failure is not the same. Therefore, while knowledge is helpful, don’t take it too seriously especially if the prevailing mood is to experiment and take risks.

Do more, criticize less

You need to adapt to the culture very quickly. If responding to emails at 1 am is important, start doing it. Don’t start with being critical. If TED talk videos are the norm on Monday mornings, be a part of it. If beer parties after review meetings are a way of bonding, don’t find reasons to skip them. You may have a family to go back to, but find a way of achieving a balance without making your younger colleagues feel that you don’t see yourself as a part of this culture.

The bottom line is you need to genuinely start enjoying being a part of the team and what it stands for. Once you’ve established your unquestioned membership in the culture club, you can take a few liberties and also try and introduce some changes.

But speak out about the important stuff

You should, of course, put your foot down when it comes to things that are fundamental and non-negotiable. For instance, young startups may not realize that you can’t schedule meetings on the fly at 10 pm and expect the women in the team to participate whole-heartedly and not give a serious thought to their safety on their way back home.

If you see such a culture, you need to rapidly educate everyone on the importance of building practices that will create a more inclusive and diverse environment and why it matters for the business!

Take the back seat

Never forget that the 32-year-old is the boss. You don’t have to step in to add or correct everything—despite the temptation—or communicate messages that need to be communicated by your boss. If you do need to do it, do it delicately.

But help your boss when they need it

But don’t forget that everyone has their insecurities, and they tend to be a little more pronounced—though hidden—in young leaders. Because they don’t know who to go to or how to address the problems they are faced with on their own, the problems fester.

Break the age stereotype

Know that experience isn’t everything

Use experience to solve actual problems

Be willing to learn