What I learnt working for a young boss

What I learnt working for a young boss

Monday June 26, 2017,

6 min Read

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 at that point of time.

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 much like Uber, by Sanjeev Aggarwal, the Managing Partner at Helion Ventures (and investors at TFS).

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! I went for 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 about 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 join us and help us accelerate our journey.”

Obviously, the short conversation WAS the interview, but nevertheless, 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!

As far as learning is concerned age is no bar. (Image: a still from the Hollywood movie, 'The Intern'.)

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

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

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 Monday morning TED talk videos are the norm, 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 change.

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 realise that you can’t schedule meetings on the fly at 10 pm, 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!

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

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.

Young leaders could be outstanding at solving some very complex problems but might trip over some fairly simple problems. You can help address these insecurities and problems by helping him/her deal with them. Board issues, tricky team issues, and difficult conversations are some of the common ones.

Youth and experience make a great team. (Image: a still from the Hollywood movie, 'The Intern'.)

Every age group is associated with certain stereotypes. Don’t live up to these stereotypes. Normally, in corporate life, age is associated with not being hands on, a tendency to pontificate, low energy, and ignorance about the cool new trends, amongst others. Break these stereotypes. Firstly, it will help you earn some respect, and secondly, you will genuinely reinvent yourself and begin having fun all over again!

Share your experiences in an understated way. Never make experience too much of a virtue. While experience is helpful, more often than not, the key to effectiveness is about being able to think correctly from zero-base in every situation, and youth does not suffer a handicap when it comes to this.

Don’t jump in with your lessons at the drop of a hat. Let the team discover a few things for themselves while you watch, unless the stakes are high. In addition, at a startup, you need to earn your stripes every day. You can’t rest on yesterday’s laurels. Yesterday is history.

Today is a new day. You won’t be excused for not doing what is expected of you today because you were walking on the water yesterday. If history is irrelevant, experience counts for very little. Credits cannot be carried forward. They expire by end of day!

Don’t just share lessons from experience. It doesn’t help and is not valued. Use your experience in helping others solve some of the difficult problems they are grappling with. They will begin to appreciate the usefulness of asking you for help rather than wasting time reinventing the wheel.

Acknowledge and praise those younger than you for what they are really good at, and genuinely learn from what they are good at.

Above all, this experience reinforced what I suspected all along, but was never really sure of: Life is all about not letting success get into your head, having your feet firmly on the ground, having a child-like curiosity, willing to learn from anyone, ability to discuss an idea with anyone without prejudices, and an ability to easily say, “I don’t know this” or “Can you tell me more about this.”

If you truly believe this, you can liberate yourself from some of your self-imposed constraints and start enjoying life all over again.