The Hard Thing About Hard Things
Laying off my own team haunts me. Ben shows how to gutless your way through the nightmare.
leadershipSpend zero time on what you could have done, and devote all of your time on what you might do. Because in the end, nobody cares; just run your company.
AQ's take: Dwelled on past fuckups. Killed progress. Future focus revived me.
Mar 11, 2026In good organizations, people can focus on their work and have confidence that if they get their work done, good things will happen for both the company and them personally. It is a true pleasure to work in an organization such as this. Every person can wake up knowing that the work they do will be efficient, effective, and make a difference for the organization and themselves. These things make their jobs both motivating and fulfilling.
AQ's take: Built trust org once. Pure joy. Chaos elsewhere? Soul-crushing.
Mar 11, 2026Andy Grove’s management classic, High Output Management, titled “Why Training Is the Boss’s Job,” and it changed my career. Grove wrote, “Most managers seem to feel that training employees is a job that should be left to others. I, on the other hand, strongly believe that the manager should do it himself.”
AQ's take: Skipped training my devs. Chaos ensued. Grove nailed it: bosses teach.
Mar 11, 2026In my mind, I was keeping everyone in high spirits by accentuating the positive and ignoring the negative. But my team knew that reality was more nuanced than I was describing it. And not only did they see for themselves the world wasn’t as rosy as I was describing it; they still had to listen to me blowing sunshine up their butts at every company meeting.
AQ's take: Bullshitted my team rosy lies. They saw through it. Honesty rebuilds.
Mar 10, 2026For example, consider the old management standard: “Don’t bring me a problem without bringing me a solution.” What if the employee cannot solve an important problem?
AQ's take: Told juniors 'solve it yourself.' Broke them. Leaders fix the unsolvable.
Mar 10, 2026If you run a company, you will experience overwhelming psychological pressure to be overly positive. Stand up to the pressure, face your fear, and tell it like it is.
AQ's take: Faked endless optimism. Burned out hiding pain. Truth frees you.
Mar 10, 2026“There are no silver bullets for this, only lead bullets.”
AQ's take: Silver bullets? Chased them broke. Lead bullets built my grit.
Mar 10, 2026An early lesson I learned in my career was that whenever a large organization attempts to do anything, it always comes down to a single person who can delay the entire project.
AQ's take: One asshole stalled my launch for weeks. Single blockers kill momentum.
Mar 6, 2026It turns out that is exactly what product strategy is all about—figuring out the right product is the innovator’s job, not the customer’s job.
AQ's take: Chased customer 'needs' blindly. Wasted years. Innovators decide the product.
Mar 6, 2026Note to self: It’s a good idea to ask, “What am I not doing?”
AQ's take: Forgot my blind spots. Asking this saved a sinking project.
Mar 6, 2026People always ask me, “What’s the secret to being a successful CEO?” Sadly, there is no secret, but if there is one skill that stands out, it’s the ability to focus and make the best move when there are no good moves.
AQ's take: No good plays in crises? Picked the least bad. Focus forged me.
Mar 6, 2026If we hadn’t treated the people who were leaving fairly, the people who stayed would never have trusted me again.
AQ's take: Screwed over leavers once. Lost trust forever. Fairness saves the stayers.
Oct 28, 2025The hard thing isn’t setting a big, hairy, audacious goal. The hard thing is laying people off when you miss the big goal.
AQ's take: Firing my first team crushed me. Hitting layoffs head-on? That's the real gut punch.
Oct 24, 2025It taught me that being scared didn’t mean I was gutless. What I did mattered and would determine whether I would be a hero or a coward.
AQ's take: Faced shutdowns terrified. Action proved I wasn't spineless. Still scares me.
Oct 24, 2025