What Are You Optimizing For?

How often do you catch yourself in the middle of some fight only to realize it doesn’t really matter? Or, how many of your opinions are “strongly held” even though they’re no longer serving you (if they ever have)? A prevalent leadership fallacy I come across is seeing clients who are optimizing the wrong metric. […]

Miscommunication Plan

It’s funny, I expected geeks-turned-managers to be better at communicating changes to their teams. After all, they often have years of experience thinking about meticulous database migrations, feature rollout plans, and just thinking about how things will play out. Frequently enough, though, we don’t seem to apply these skills to how we talk to our […]

Permission to Take the Lead

For many, a nontrivial leap has to occur when transitioning to senior leadership roles. Most of the formal education and prior work experience people have inculcates a necessity to follow directions, being told what to do, getting permission. If you continue waiting to be permitted to do what needs to be done in your new […]

Preventive Plans and Contingencies

If there’s one thing that you can count on most tech executives being very attuned to, it is the risk management of the different product engineering work in their organizations. They are often equipped with years of experience as technical ICs and have become calloused enough to think about all the different things that can […]

Forming Alliances

Every senior leadership role gets lonely from time to time. It is natural and yet extremely exhausting. Even the most energetic people I worked with, when truly alone, see their resolve slowly abrade with time. I’ve got good news, though, you don’t have to accept this loneliness! First, I’ll start with my basic premise for […]

Pop Quiz: Objectives Inspection

This is an excellent time of the year to flush out a lot of faux processes. Less than two months have passed, and already I bet many of you have lost track of the fancy roadmaps, goals, or OKRs that you worked so hard on creating. Let’s quickly review your goals upkeep and assess how […]

People Over Processes

People are not software, no matter how hard we try. That means that some plans and approaches that might seem nice on paper are doomed even before you send the first Slack message to talk about them. It might seem trivial at first pass, but I routinely see people try and do things in a […]

Courage Over Fake Niceties

A malady across tech worldwide seems to be the sanctity of amicability, even at the cost of harming the work we came to do. Many people tend to avoid arguments, but I’m talking about something that takes this to a whole other level. We see leaders with nicely laid out copies of “Radical Candor” on […]

The Void of Empowerment

A recurring issue for people as their position in a company becomes more senior—either due to being promoted or having the organization grow under them—is the feeling that they are slowly being moved away from influencing the team. We all talk about empowered teams, but what happens when you actually achieve something that resembles such […]

Team Empowerment Alignment

I’m a big advocate of empowered product teams and have helped many companies make a healthy transition towards such a culture. However, I regularly come across executives who think they have already achieved this while, in fact, having created expensive Jira resolution machines. There are also scenarios where I believe a shift to empowered product […]