Dear Leaders,

Every now and then · by Hamza Shayk

Judgment

Twelve Hours Isn't Twelve Hours Anymore

Sometime in the 1920s, the psychologist Kurt Lewin was sitting in a Berlin café with his students when he noticed something odd about their waiter. The man could recall every unpaid order at every table without writing anything down.

Oct 9, 2026

A Players, B Players, C Players

A few decades ago, I heard Bill Gates give an interview about Microsoft's success. People think Microsoft is a technology company, he said. It isn't. It's a company that hires.

Jul 24, 2026

Management Has a Public Relations Problem

In 1911, two men raced to become the first to reach the South Pole. Robert Falcon Scott led the British expedition. He viewed the journey as a noble test of human courage.

Jun 13, 2026

What Are You Waiting For?

Last weekend I read Waiting for Godot (pronounced “good-o”) for the first time. It’s a short play, 109 pages, that Samuel Beckett wrote in 1953. A story of two men, Vladimir and Estragon, sitting by a barren tree waiting for a man named Godot to arrive.

May 21, 2026

How Our Labels Become Our Identity

I have a friend who is chronically late. Not occasionally late. Structurally late. Everyone who knows her automatically assumes she’ll arrive ten to X minutes after the agreed time.

May 7, 2026

That Dirty Word: Micromanagement

I hear it more often now, which usually means a word has begun doing damage. A highly successful executive sits across from me, lowers their voice, and confesses: “Hamza, I think I’m a micromanager.”

Apr 23, 2026

How to Play the Game

By now, two things are clear. Merit gets you in the room. Politics determines how high you go once you’re there. And the power driving those outcomes isn’t necessarily on the org chart — it flows through relationships, informal structures, and contexts you must map.

Mar 12, 2026

When Hitting the Numbers Still Means Losing

In the waning days of the British Raj, Delhi had a cobra problem. Venomous snakes were everywhere. The colonial government, staffed by men trained at the finest institutions in Britain, devised a perfectly rational solution: a cash bounty for every dead cobra.

Feb 10, 2026

Why We Avoid Simple Solutions

In 1847, a Hungarian doctor named Ignaz Semmelweis made a discovery that should have made him a hero. Instead, it destroyed him. Working in the obstetrics clinic of Vienna General Hospital, Semmelweis noticed a horrific trend.

Dec 4, 2025

The Abilene Paradox

It is a stifling July afternoon in Coleman, Texas. 104 degrees in the shade, and the wind is blowing dust. A family is sitting comfortably on a porch, drinking cold lemonade and playing dominoes.

Nov 28, 2025

Are You Self-Aware or Just Self-Absorbed?

A couple of months ago a CEO told me, “I know I’m not great with people. I’m very self-aware about that.” Then, in the next twenty minutes, he proceeded to interrupt his CFO twice, dismiss a perfectly reasonable concern from his head of sales, and check his phone while his CMO was mid-sentence.

Nov 21, 2025

How to Run a Company in a Culture War

Welcome to business in 2025, where cultural illiteracy is more expensive than financial illiteracy, and a single Instagram post can erase decades of brand equity in a day.

Nov 13, 2025

The Only Way Leadership Quality Actually Improves

Leadership quality is the single most valuable, and least measurable, asset a company has. It’s the only one that compounds across every other dimension simultaneously.

Nov 7, 2025

To All My Confused CEOs

Jensen Huang was on stage at GTC explaining NVIDIA’s strategy when an analyst interrupted: “But what exactly ARE you? A gaming company? A data center company? An AI company?”

Oct 28, 2025

Hiring Today: You Fool Me, I Fool You

I just spent a half hour reviewing resumes for a simple analyst position. One candidate claimed to be “fluent in leveraging cross-platform ecosystems to drive holistic value creation.”

Aug 15, 2025

The Myth of Authentic Leadership: Why ‘Be Yourself’ Is Often Bad Leadership

We’ve convinced ourselves that good leadership means showing up as our “authentic selves.” That vulnerability builds trust. That transparency creates connection.

Aug 6, 2025

Smart People, Bad Decisions, and What To Do About It

The most dangerous people in an organization aren’t the obviously incompetent ones, because they can be identified easily. The real danger is the brilliant people who make terrible decisions while sounding completely reasonable.

Jul 30, 2025

Being Right Vs. Being Effective: A Leadership Dilemma

Would you rather be right or effective? Every one of us has fallen in love with the idea of being right. It’s so tempting: facts, logic, data. “The numbers don’t lie.”

Jul 23, 2025

When Emotional Intelligence Goes Too Far

Being able to read a room, handle difficult conversations, and connect with people on a human level is leadership gold. No debate there. But somewhere along the line, EQ stopped being one tool in the box and became the whole toolbox.

Jul 16, 2025

Executive Dilemmas: The 3 Brutal People Decisions Leaders Face

Every senior executive reaches a point where hard skills don’t matter anymore; only judgment does. The hardest leadership decisions then aren’t about operations or strategy.

Jul 9, 2025

The Key to Decision Velocity: “I Disagree and Commit”

In executive decision-making, few phrases are more effective, or more underutilized, than “I disagree and commit.” It means: I’m mature enough to speak up, clear-headed enough to let it go, and committed enough to execute without hesitation.

Jul 2, 2025

The True Cost of Self-Deprecating Language

I’m seeing more and more leaders hedge in conversation. Often to the point of self-deprecation. You’ve heard lines like these: “I’m probably way off here...” “This might be a dumb idea...” “I’m no expert, but...” “I’m such an idiot.”

Jun 26, 2025

The Relationship Between Commitment And Fulfillment

What is the relationship between commitment and fulfillment? Can we truly experience fulfillment without committing to something? To be clear, commitment isn’t necessarily working 60 hours a week.

Jun 12, 2025

Feel Like An Imposter? You’re Doing It Right

The higher you climb, the better people get at masking it. But I’ve yet to meet a serious leader who doesn’t, at least occasionally, feel like a fraud.

Jun 2, 2025

Is It Just Growth or Also Progress?

We love to talk about growth. Revenue growth. Headcount growth. Market share growth. Growth sounds impressive because it is measurable. It’s easy to put on a slide.

Apr 30, 2025

BY GENRE

Executive isolation

Organizational drag

Incentives and measurement

Judgment

People decisions

Power and politics

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ABOUT HAMZA

I advise CEOs and senior investment professionals on difficult decisions, executive development, and organizational performance. My clients lead public, private, PE-backed and family-owned companies, or hold senior roles at investment banks, asset managers and private equity firms.