8 Learnings from Leaders for a Successful Career

Karthick Natarajan
6 min readJan 30, 2022
“Clock — Success” by flazingo_photos is licensed under CC BY-NC 2.0

Over the course of my career, I’ve had the privilege of reporting to some really elite leaders who were not just strong performers in their own domains but also had the knack of building and nurturing a team of rockstars. My journey from a college graduate with very little corporate world exposure to where I am today was guided immensely by the interactions with them and the learnings from those interactions. What’s interesting is that I’ve reported to managers who were one level above me to those who were seven levels above, and this has added its own dimension of learning to the mix — observing someone close to your role helps understand what are the immediate areas you need to do better in to advance, while observing someone multiple levels higher enables you to get a sneak peak into the kind of big picture decisions they take every day and more importantly, the strategic lens through which they view everything.

While it’s obviously impossible to provide an account of all the good stuff these leaders have taught me (and are teaching me), I’ve tried summarising the top 8 along with my realisations.

  1. Learn to say NO unapologetically.

This isn’t new but it was refreshing to see this put to work. Traditionally we’ve been taught not to hurt others, and just because we connect saying no to hurting someone, this is one of the most challenging things to do. What I’ve seen though, is that saying no up front and setting the right expectations is much better than taking on more than one could deliver and disappointing others. Some of the leaders I have seen are ruthless in this aspect, and they and their teams are better because of this. And whether it’s obvious or not, this is a major source of respect — primarily because this signifies care. Someone saying a firm NO cares not just about themselves, but also their team, their product, their customers and also the person who they are saying no to.

2. No decision is perfect, but make them anyway.

The simple fact that the effect of a decision we make today is going to be in the future should indicate that we have no control over it, but that doesn’t stop us from overanalysing decisions. This leads to constant procrastination as we keep running every scenario in our head and don’t stop until we are either up against a deadline pushing us to act or someone gives us the confidence that it will work. Truth is, we are amazing at imagining bad outcomes and more often than not, outcomes turn out to be better than we imagined. Leaders I’ve worked with have realised that perfection sometimes hinders progress and just move forward, clearly documenting the possibilities and having a backup plan in place in case something goes awry.

3. Opportunity? Take it. You’ll figure it out.

There used to be a time when you needed every skill and qualification as per definition to get into a role, and anything different was termed putting the cart before the horse. Guess what? That cart was dragged away years ago. If you see an opportunity coming up where you may not check all the boxes, go for it. It’s coming to you because someone trusts you to figure it out and you will. We live in an age where lucrative degrees don’t guarantee success and dropping out of school doesn’t mean you’ll be a failure. But one thing is sure — giving up on opportunities is a crime. As long as you don’t have something that’s as good as or better than it, take it. Many of us figured out how to walk when we were barely 1, so this shouldn’t be a big deal.

4. Team first. Personal growth next.

This doesn’t mean the leader lets his growth stagnate while those on the team flourish, but a lot of emphasis is given to the latter. In line with the great proverb “Give a man a fish, and you feed him for a day. Teach a man to fish, and you feed him for a lifetime”, a leader who delegates, teaches and coaches their team has a massive positive impact on their career compared to someone who shields them from difficult tasks. Putting them in challenging situations with enough support helps them learn and expand their horizon. As Kim Scott rightly puts it in her classic Radical Candor — it is as important to care deeply as it is to challenge directly. When your team grows and is able to take on bigger challenges, your growth just follows.

5. Trust people and they’ll repay with loyalty.

Even 5 years ago, managers in several organisations were reluctant to let employees work from home. The reason? The notion that having them right in front of you is a sign of control — control over what they are working on and how they are performing. Obviously the pandemic changed all of this upside down. Where’s this perceived control when your team’s working from across the country or even the world from their homes? What’s heartening to see though, is that the outcome’s gone up. Everyone’s coming to the realisation that trusting team members does have its own advantages. Besides, money’s not all that an employee cares about — they need to be recognised, motivated, challenged and more importantly, trusted. What you spend in the currency of trust, you get back in the currency of loyalty. And surprisingly, both sides gain in this exchange.

6. Make your point, and move on.

As we become more experienced and comfortable in a setting, we start to challenge decisions. Sometimes, when a project is close to our heart, we tend to become to attached to it and our opinions about it are stronger than usual. This makes it difficult to have assertive arguments with those who have opposing views, and this ends up souring relationships. It’s important to extricate yourself from the attachment and look at all these views objectively. Ask yourself this simple question — is there 0% possibility that the other person’s idea will make the project better? Remember, the question is not if it’s better than your idea — that will only lead to ego clashes. Once you realise there’s some merit to the idea, it’s easier to move forward. It is also possible that it’s your boss who’s making the other point and doesn’t seem to listen at all. So if you can’t move forward, move on.

7. “How are you doing” is more important than “what are you doing”.

Another aspect that’s gaining centre stage of late is empathy at the workplace. Simply put, this is the ability to understand someone’s situation and being sensitive to it. The word may sound complicated, but in truth it is not — it just requires one to be open minded and listen. Paying attention to how others are talking, expressing views over video, responding over chats, replying to mails, etc can reveal a lot. There’s a difference between prying, which would be crossing a line and paying attention to show care. A couple of the leaders I’ve worked with can easily sense when something is not right, and will follow it up with a “let’s take a walk and chat”, which is a gesture that makes a world of difference to the team member’s morale. But to make this happen, it’s important to shift the focus from what they’re doing to how they’re doing.

8. Accountability transcends all textbook role definitions.

By far the most common lesson I’ve learnt from all of them is to not be bound by job definitions and role boundaries. Yes, they’re there for a reason, but don’t work well in a crisis or when things aren’t going as planned. There are going to be innumerable situations where someone isn’t available to finish their portion of a work that’s approaching its deadline, they don’t have the competency to do it effectively, have done a bad job that can’t just be taken forward or just needs help because it was underestimated in the first place. It’s easy to sit back and let them handle it because it’s just not your job, or step in and help directly or indirectly by getting the right people in who can directly help. This also ties back to #4, where you provide support when needed. I’ve seen engineering leaders get down to coding, product leaders doing discovery and drafting requirements, and even CEOs reviewing data integrations. If you want to grow, want your team to succeed, want your customers to be happy, there should just be no boundaries for your accountability.

Conclusion

Whether you are just starting your career, or someone who’s spent years in different roles, these learnings will apply to you. Try to choose a few from these and try implementing — you’ll clearly see a difference in how others see you, and in how you see yourself.

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Karthick Natarajan

Passionate product manager with years of diverse experience in product and project management, business analysis and digital product ownership