An Uncertain Trumpet

  • Gogi Gupta
  • Gupta Media
  • Apr 15, 2022

One of the scariest moments of my life was when I was laid off from my first job. It was June 2001, the bubble had burst 16 months earlier and I was sent wandering into the carnage of the dotcom bust.

I was young, poor, and alone.

It was awful.

19 years later, I found myself in a position that was worse.

In June 2020, I was the one writing the layoff lists.

I was older and wealthier but again, alone.

It was still awful.

Being a leader means making hard decisions, that is part of the contract. Only in the fine print do they tell you that what makes these decisions so hard is that they come at someone else’s expense.

We made the lists, went through the contingency planning, cut expenses, dipped into our rainy day funds, took the PPP, and begged clients to pay us. We pulled every lever and pushed every button.

Every task felt Sisyphean but, in the end, the gods granted us a reprieve.

No layoffs.

But, I still knew who was on those lists.

My innocence was gone, and I am still cursed by that knowledge.

Over the past two years, it feels like every decision has been a hard one. Every decision makes you squirm, makes you worry you made the wrong decision. Every decision makes you uncomfortable.

Do you reopen the office?

How do you support your staff, especially their mental health?

How do you give your new hires the tools & environment they need to grow professionally?

There is an innate tension in all of those decisions.

I am tired of having to make hard decisions, tired of being uncomfortable, but for leaders, the gods won’t grant a reprieve from that curse.

You have to be comfortable with being uncomfortable.

During this pandemic, I have adopted a few techniques that help me get comfortable, or maybe more accurately, become less uncomfortable.

I acknowledge that my early decisions will be wrong, which means that I change my decisions often

In statistics, this idea is encapsulated in the concept of Bayesian Inference. Colloquially (among the geeky set) it is sometimes referred to as “updating priors.” In even simpler terms, it means that as you encounter new data, your entire decision-making process is redone and your decision may change.

If you want to criticize, I am a flip-flopper. I lack conviction. I make decisions without waiting for “all” the data to come in. I rush into things.

While those barbs might have some amount of truth to them, I still believe that the humility in knowing that you will be wrong helps you more quickly arrive at the optimal decision.

If you find yourself on the receiving end of those barbs, keep this quote in your back pocket.

“When the facts change, I change my mind. What do you do, sir?” – John Maynard Keynes

I overshare

We have monthly Town Halls. I send agency-wide emails about the power of “yet.”  We survey everything. I write long-winded posts on LinkedIn… I let them in.

I know that some people will disagree with me on the principle and substance of any given decision, but I hope that my previous oversharing allows them to unpack the “why” behind those decisions.

Once you are in a position where your decisions impact many people, you owe (yes, owe) them a look behind the scenes into your thinking and reasoning. Taking that point further, you will be a better leader by letting them know you — a multi-dimensional, reasonable, and imperfect human.

I share half-baked ideas

I put forth 80% complete solutions and let my management team tear it down. I’m sure that some of them wish the ideas were more complete, but I’ve found that a complete idea gets a binary response.

An incomplete idea gets a fuller response. When my managers know they can influence the outcome, they get more deeply involved. They are no longer bound by agreeing or disagreeing with my decision; they are liberated to shape our decision.

I trust my emotional intelligence (“my spidey sense”)

I acknowledge pushback. I have become fluent in eyebrow furrows, tense shoulders, and side-eye.

I hear the difference between “Sure…” and “Sure.” and “Sure!” and know that the slight difference belies a bigger difference.

Being an uncomfortable leader has made me hyper-aware that others are also uncomfortable.

What I learned somewhere during this pandemic is that you can win them over. You can be a good leader. You can convince them with a sound argument and have them believe, but you have to do it slowly, openly, and with kindness.

Theodore Hesburgh once said that “the very essence of leadership is that you have to have vision. You can’t blow an uncertain trumpet.”

“Yet,” here I am, an uncomfortable leader, playing an uncertain trumpet but certain that my approach meets the moment.

Gogi Gupta Photo

Gogi Gupta Gupta Media

Gogi Gupta founded Gupta Media, a performance marketing agency, over 20 years ago. He saw where the digital world was trending and decided to start an agency that would shape a new media landscape. Gogi had never worked at an agency. He was an outsider with a vision for how companies could buy online ads more efficiently and effectively. Since then, Gupta Media has become a leading performance marketing agency, representing some of the biggest names in music, live entertainment, and tech. Gogi has shared his passion for efficient marketing at industry events, on CNBC, and with publications like the New York Times, Reuters, and CBS News. Gupta Media’s strategy for performance marketing in the digital age has also been the subject of a Harvard Business School Case Study taught to HBS students since 2017. When Gogi isn’t working, he’s spending time with his wife and three daughters and rooting on the Boston Red Sox and Buffalo Bills.
Category Leadership