Guide for first-time leaders to deal with leadership paradoxes


I felt like an impostor, broke my back working long hours and developed an abnormal sleep pattern when I became a leader.

Leadership is brutal. There isn’t a question that everyone who starts leading dreads it initially. The burden of carrying the trap to please everyone is too hard to carry.

Especially people like me who were comfortable with certainty of swimming in binary world before signing up for the chaotic uncertain waters of managing other humans.

Leading people made writing programs in assembly look like child’s play.

I wish now that someone could have held my hand and guided me through this transition. I had good managers, read lot of insightful books but the advice I read or heard was so divergent that it was difficult to wrap my head around it.

If you got promoted to be a leader and are baffled, like I was, with some of the common leadership paradoxes, then please read on. This wouldn’t answer all the questions but might help you think critically about the leadership paradoxes. Or, sometimes the divergent advice that would be thrown at you.

So, who is a “leader”?

A leader has to deal with ambiguity yet bring in clarity. To share decisions with full conviction even when she has half-baked information. To manage shifting and conflicting priorities at the speed of light. To give her people the vision for future when her own foresight be hazy. To be the beacon of hope and uplift people when she might be drowning in despair. To be the chief excitement officer even when she is depressed. To coach and mentor people when they might be taking potshots at her. To take blame for all failures while giving away the entire credit for the success to the team.

Phew, sounds like a thankless fucking job, doesn’t it? Makes you want to wonder why so many people still sign up for it!

Because, there isn’t a better job where one can have a phenomenal impact despite the above description. A probable life changing impact on other people and the future of that leader’s group. That is, when it’s done right.

Leadership is the position where you can enable or influence people to make a dent in the universe. 

If the right kind of leadership can help influence greatness then what’s the recipe to become the best? What should be the advice for the first time leaders who are trying to make a difference?

Here is some of the common yet conflicting advice to become an inspiring leader –

  1. Be Transparent. Like a mirror. Always.
  2. Be your team’s shield. Be their Captain America.
  3. Fail fast. And while you are at it, break shit as well.
  4. Never ever give up. Yup, don’t even think about it.
  5. Be consistent. Like the sunrise.
  6. Constantly learn. Also, unlearn.
  7. Don’t sweat the small stuff.
  8. God is in the details, yo! If you were to stay in the temple of details, you might find your salvation.

Oh boy! Is it only me or do you also see some contradictions in this advice too?

It’s a horrid tale of incongruence which can throw anyone in a tailspin. And, if you swim long enough in this sea of incongruence, it wouldn’t take time to go from leadership to leadershit.

So, what can one do? Is there help available? What is one to make of these contradictions?

All I can do is attempt to reconcile the divergent advice so that you can be judicious about when to do what.

Be transparent yet shield your team

Transparency is the dope that lets you get high on trust. 

How can one be completely transparent yet shield one’s team from bad news, inter company politics, or any other shit storm?

Yeah, you got that right — 100% transparency is a myth. But who said that you can’t be as transparent as possible?

You never have to dress up the facts. You can share facts about the project’s health, company’s direction, or your people’s performance. Your people don’t have to second guess where you are coming from. You say facts as they are and everyone in the team knows your world views.

You might piss people off when you let them know transparently about their shitty work. But, hey, at least they know how you feel and how they can always count on you to share things as they are.

The only time that you might not want to be transparent is when divulging the details would lead to an irreparable motivation damage. You must find a way to either contain the situation or share the details at an appropriate time and place.

Like, if you are running a services organization, you don’t want to share if a client is being difficult or unprofessional. Once you transparently share your feelings about the client then your team might eventually lose the motivation to work on the project.

So, be transparent but shield the team temporarily only from the facts that can have a severe repercussion on their motivation.

Never ever give up but fail fast

One of the best paradoxes of leadership is a leader’s need to be both stubborn and open-minded. A leader must insist on sticking to the vision and stay on course to the destination. But he must be open-minded during the process — Simon Sinek

You must have heard this pure unadulterated bullshit cliche — Impossible means I’m possible.

There are things in life that aren’t possible. Period.

“It works on my machine” — try getting anything else out of a developer when you share a bug with them.

Impossible 🙂

Everybody loves a leader who doesn’t take no for an answer. Someone who has a bowl of tenacity for breakfast every morning. Someone who never ever gives up despite adversity.

But we often hear, especially in the startup world, fail fast. How on the earth can the same person who doesn’t know how to give up fail fast? Baffling! I agree.

To be honest, it’s not that confusing. Let me explain.

When I hear these kinds of divergent advice, I just interpret it as never giving up on the goal, per se. Be stubborn. Try out different things, ideas and strategies without ever losing the focus on your goal. If an idea or strategy has been proven unworkable then quickly move on to the other.

Thus, fail fast is in the context of achieving one’s goal, not an overarching advice. Overall, leaders must be tenacious or stubborn.

Be consistent yet constantly learn

Leadership and learning are indispensable to each other — John F. Kennedy

How can one be consistent yet constantly evolve? Is that even possible?

Everyone expects their leader to be consistent and predictable. Especially in decision making and their behavior. But, if a leader is to judged on predictability then how does she learn? Or, unlearn the bad habits. Or, simply evolve.

Consistency should always be expecting the best from your team, upholding high standards of execution and your core values.

Apart from that, as a leader, you should constantly learn new skills. Read a lot. Challenge your thinking. Unlearn the techniques that hold you back. Unlearn your bad habits.

Last but not the least, I hope the pessimistic sounding lines of your team — “She has changed” should bring out only one response. Fuck yeah!

Thus, be consistent in constantly evolving.

Don’t sweat the small stuff but practice attention to detail

It’s the attention to detail that makes the difference between average and stunning — Francis Atterbury

Either I don’t understand the saying of “don’t sweat the small stuff” or the guy who came up with the phrase merely dished out some crappola.

There shouldn’t be any paradox here.

As a leader, it’s your job to sweat the small stuff. God is in the details, you know.

Whether it is design, engineering, manufacturing, customer experience, or anything which your group is responsible for — you need to make sure that you have the right people, process and culture to deliver exceptional products and services.

And, like they say, “culture flows from the top”. Thus, you need to make sure that you sweat the small stuff and bring about the best outcome for anything that your group touches. Period.

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