Three challenges of leadership

Uncomfortable aspects of leading

Abhinit Singh
3 min readJul 6, 2023
Photo by Markus Spiske on Unsplash.

The popular perception around leadership if attractive yet flawed; it is far from someone posing puff-chested on a mountain peak with the sun rising behind as a halo. But I get the point: it is meant to sell the idea that taking troubles you could do without is a good choice. Smart.

There are perks, sure. Someone offers you their chair when there’s none available; you get the proverbial name on the wall and an enhanced quota of chai-samosa. Euphoric; until La La Land comes crashing down, and you realize there’s stuff that you need to get done. Just like lunch, no chai-samosa is free.

I’ve had my fair share of troubles dealing with disillusioned teammates, grumpy stakeholders, and, rarely, workplace romantics. Here are three things that I found the most challenging:

Appearing confident when you’re not

Photo by Towfiqu Barbhuiya on Unsplash.

It doesn’t sound cool, I know. But for all the talk of celebrating vulnerability, few would take instructions from confused leaders. When push comes to shove, you wear the bright face regardless of what’s cooking inside your mind.

Decisions carry uncertainty; time doesn’t give you forever to decide. Yet, it is far-fetched to inspire action from the team until you appear to have clarity over the execution. The downside is that failure is all on you.

Everyone knows the objective, but you are the only one juggling with all that could go wrong. Your name on the plaque signifies stature, but it also means that the pitchforks come for you when they do.

It’s frustrating sometimes, but it comes with the job.

Fielding universal discontent

It’s impossible to keep everyone happy, and leading reminds you of that daily.

Every decision has a challenger, everyone thinks they are overworked, and a few think they could’ve done a better job than you. The point is everyone is capable of something that serves the objective. So, even as you fume inside, you wear a calm face and pacify the disgruntled.

It is especially tough at the beginning when you are new to the position and haven’t dismounted the high horse of self-righteousness. Experience makes it easier with time.

Everyone has their truth, and you need to make peace with disagreements.

Unseen triumphs

Leadership isn’t always exciting; most work is about keeping everything from exploding. Unfortunately, the effort is only visible to those that work closely with you, while failures make for public debate.

“It’s bad, but it could’ve been worse” never makes a good argument.

Popular opinion doesn’t celebrate efforts toward maintaining order. No wonder ‘change,’ ‘revolution,’ and ‘disruption’ make buzzwords for all elections. So, why bother?

Because it is worth something to be consequential, to know that things taken for granted were built by you, to understand that your impact would be felt long after you’ve moved from that place.

Impact trumps popularity, always.

Three is too small a number to quantify leadership’s challenges; I’ve only included the ones that I experienced, the ones that are the least discussed in the subject.

I hope you found the article helpful!

You might also like to read about the curse of minimalism. Cheers.