#leadership

"This is moving too fast. We need more planning." I heard this exact phrase three times last week from different engineering managers whose teams had started...

When it comes to remote work, hybrid setups, and office mandates, most debates miss the real point. It's not about which model is _better_ in some universal...

Conflict Isn’t the Enemy—Fear Is It’s tempting to equate “healthy teams” with harmony. No arguments, no friction, no tension—just a constant chorus of agreement...

One of the most quietly corrosive things a company can do is overhire. Not because people are malicious or lazy.

You’ve probably seen this play out. Someone shares an idea—bold, certain, maybe even brilliant-sounding.

A while back, I came across a hiring philosophy from Varun Mohan, co-founder and CEO of Windsurf, that stopped me cold.

The Answer Is Obvious—You Just Don’t Like It: You’ve probably seen this happen. A smart, capable person presents a gnarly problem.

I've spent the last decade observing founders across every imaginable sector—from AI startups racing to define our technological future to direct-to-consumer...

The Magnificent Chaos of Founding: A Love Letter to the Startup Rollercoaster: The Dance of Euphoria and Despair 9:00 AM: You just closed a major client. You...

The best product managers have a superpower that's rarely discussed: they can spot the same underlying user need manifesting in completely different ways acr...

The most dangerous thing about startup advice isn't that it's wrong—it's that it's partially right. After years of building products and watching others do t...

When the Ask Feels Awkward, It’s Already Too Late: There’s a thing someone on your team is supposed to own. But you hesitate to bring it up.

Let’s talk about a particular flavor of leadership dysfunction: the passive-aggressive manager. You’ve probably worked with one.

For startup founders, sales isn't just another function—it's the lifeblood of your business. Early on, founders are usually the lead salesperson, passionately...

Few workplace rituals inspire dread quite like performance reviews. Employees brace for ambiguous feedback, and managers groan at the prospect of endless pap...

In the relentless push to build and scale, organizations often overlook a critical piece of infrastructure: how decisions get made.

OpenAI recently rolled back a GPT-4 update due to sycophantic behavior. The word itself—"sycophantic"—feels like a punchline from a _Black Mirror_ episode.

In my role leading cloud security integrations, I speak with dozens of CISOs every month. Before joining the product side, I spent seven years in security op...

"This isn't what we asked for." Five words that strike dread into every engineering team. Five words that signal a fundamental breakdown in the engineering-p...

The Executive Trap I've seen it happen a dozen times: A brilliant engineer becomes CTO and suddenly decides their job is "managing the engineering organization..."

In medical school, students take the Hippocratic Oath, pledging to "first, do no harm." As product managers, we'd do well to adopt a similar mindset.

In the rapidly evolving world of cybersecurity, organizations face an overwhelming array of security tools and solutions.

The most valuable code I've ever written was messy, quick, and written in response to an immediate customer need.

In the decidedly fast-paced world of product management, even breakfast needs a framework. After extensive user research (asking my colleagues on Slack), mul...

In my last post, I argued against perfectionism in startup environments. Today, I want to explore the other side of that coin: when quality really matters, a...

"If I had asked people what they wanted, they would have said faster horses." This quote, often attributed to Henry Ford, encapsulates one of the most challenge...

It's been exactly three months since I returned to San Francisco, and I'm finally starting to feel like I'm settling into a new rhythm.

It's become almost a cliché at this point: leaving San Francisco, writing a lengthy Medium post about why you're done with the Bay Area, only to find yourself...

The Weight We Carry There's a peculiar heaviness to modern existence. We wake each morning already bearing the invisible weight of emails unopened, messages...