Management

Fifteen Tics

Remember Manager Readmes? The idea was that a manager would take the time to write up their leadership style, what they valued, and their principles. A fad that started in 2017, hit its peak in 2018, and then faded.1 I wrote one in March 2018 and enjoyed the process, but while I published mine, I… more

August 10, 2026

R.I.P. Your Backlog

If everything is going to plan and your operating system is in dark mode, then randsinrepose.com is now dark for you. If you are a light mode person, you can click on the Moon in the upper right of the navigation and experience dark mode stylings. Click again to return. Why now? Well, I was… more

August 8, 2026 2 Comments

The Mario Meeting

Review season. You start your career thinking the review is the most important milestone of the year, but as an individual, you only see part of the picture. Everyone cares about the compensation (base salary, bonus, and stock). That’s the data they care about, but where did this pile of compensation come from? Who decided… more

July 6, 2026

So You Want to Fix Your All Hands

I will now explain why at least 50% of your team finds your current All Hands to be a waste of their time. They believe: Now, I will describe how to build an All Hands that will exceed their expectations. Let’s define the All Hands: Everyone. Together. There’s an important organizational inflection point when you… more

June 29, 2026 5 Comments

Here’s The Rub: We Don’t Believe You

Welcome, new leader. We’re glad that you are here. Your arrival fills a critical vacancy in our team, and we can’t wait to see what you can do at this company. We’re going to say that we’re not in a hurry and you should take your time, but we’re in a hurry. Before you arrive,… more

June 15, 2026 2 Comments

The Ask

Coffee in hand, I sit down in the Cave. Any Tuesday during the work week, a sip, and I parse the calendar. 1:1 — he’s fine. Status meeting — listen. Staff meeting — read the notes from last week. Exec review — figure out the biggest fire, have a defensible opinion. Wait — Mark Team… more

May 25, 2026 4 Comments

Barely Treading Water

Carolyn, my chief of staff, sat on the couch as I ran into my office. The Palo Alto building wasn’t built for tech; it’d been adapted to support the use case over the years. My office was in the center of the building, which had an inner atrium. Way too many windows. Maybe a salon?… more

May 19, 2026 1 Comment

Sometimes Your Job is to Get in the Way

The Head of Product, Customer Service, and the CTO of Slack were sitting in the front row at an important conference. This was peak Slack; we were all the buzz, the fastest-growing enterprise software company in history. The conference speakers were singing out praises, and at that precise moment, Slack was down. Again. I wish… more

April 27, 2026 1 Comment

The Slide

They don’t want to hear it. They don’t. It is legit good feedback. It is substantive, and it is 100% true, but they do not want to hear it. How do you know this? You’ve provided the feedback several times. Three different variants of the critical feedback, and each time, the response is one of… more

April 22, 2026