Night Train: Mission Driven Product & Community Creators

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The Sailboat Exercise

A brainstorming process for garnering honest feedback about the state of a team / product / company during team retreats.

Building an AI Grocery App After the Kids' Bedtime

A decade ago, I led a team that worked tirelessly to build the grocery app we wanted to see exist in the world. This year I set out to rebuild as much of it as I could as a solo developer using AI tools.

Grocery Shopping Product Management User Experience Technology Software Development AI

Explaining late projects

Several analyses have shown that roughly half of all projects will run late or never finish. Yet, many organizations continue to be blindingly optimistic when they plan projects. This visualization explains why.

Project Management Visualizations Organizational Culture Product Management

What kept a dorm-room project alive for 20 years

October 29, 2026 - 7 min read

Think like a storyteller, act like a scientist.

Storytelling Projects Community Product Management Public Speaking

$Family Math: Why Adding One More Person Changes Everything$

Family Math: Why Adding One More Person Changes Everything

July 10, 2025 - 5 min read

If two people create X amount of complexity, then surely four people should create 2X complexity, right? Right?

Parenting Storytelling Visualizations

The mosaic — how to build a healthy team

November 20, 2023 - 4 min read

As many managers know, it’s damn hard to create and cultivate healthy teams.

Management Teams Visualizations Organizational Culture Leadership

Making hard decisions

October 3, 2023 - 3 min read

Here are some prompts you can try asking yourself when you feel stuck.

Wellbeing Behavioral Psychology Mindfulness

Strategy via storytelling

August 24, 2023 - 4 min read

So many strategy artifacts. So little clarity.

Leadership Storytelling Strategy Organizational Culture Product Management

A universal planning calendar

July 10, 2023 - 4 min read

A framework and visualization for setting up a organization-wide operating cadence that accounts for the PITA that is the Gregorian calendar.

Leadership Management Product Management Teams Visualizations

What is the hiring manager looking for?

June 22, 2023 - 5 min read

Hiring processes suck most of the time and for pretty much everyone involved. Here are some ideas for how you can fare better next time by better understanding the hiring manager’s perspective.

Job Seeking Management Teams Leadership

Where did the time go?

May 31, 2023 - 3 min read

Many organizations have this peculiar condition where employees feel both exceedingly busy AND exasperated by the lack of tangible accomplishments that stem from all that work.

Organizational Culture Leadership Management Teams

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