Case Studies
Real leadership situations. No easy answers. Built for leaders who want to think harder about the decisions in front of them.
WHAT ARE CASE STUDIES
Most leadership books tell you what to do. Case studies put you in the room before the decision gets made.
Each study drops you into a real leadership situation — the kind that doesn't announce itself as a crisis until you're already in the middle of it. A team member everyone likes but nobody can rely on. A hire that looked right on paper and isn't working. A financial decision with no clean answer. You read the scenario, you feel the tension, and you decide what you would do. Then you find out what actually happened and what it cost.
These are not hypotheticals. They are drawn from real organizations — churches, businesses, nonprofits — with names and details changed. The dynamics are real. The costs are real.
How To Use them
On your own: Read the scenario. Stop before the outcome. Write down what you would do and why. Then read the rest. The gap between your answer and the outcome is where the learning lives.
With your team: Share the scenario in a staff meeting or leadership gathering. Read it to your team or give people ten minutes to read it independently. Then discuss. You will learn more about how your team thinks in that conversation than in most performance reviews.
Where To Find them
Substack
New Case Studies drop on our Substack, one for Church Leaders, one for Business Leaders. These stay exclusive to Substack — they never appear in a book or a bundle. Subscribing is free. Every new study lands in your inbox the day it goes live, and free subscribers also get "A Second Read," me walking through a chosen Case Study on my own.
In The Trenches - Ebook series
We've also built a second, completely separate set of Case Studies — never posted on the Substack — into ready-to-go ebooks for you and your team. Pick them up anywhere you buy ebooks, or grab the PDF directly here.
In the Trenches comes in Business Leadership and Church Leadership editions, with new volumes releasing regularly. Same format as the Substack drops — a real scenario, real questions, real commentary — just entirely different material.
In The Trenches - Ebook Series
Five situations, no easy outs — a standardization push that costs more trust than it buys, a bonus plan that splits the team it was meant to unite, a call made on the worst possible morning. Work the questions before you read what I think.
A church that runs beautifully and drifts anyway. A board vote that exposes who loyalty actually protects. A photo that asks who gets to be seen. Five situations built for the room you already lead, not a hypothetical one.
Every case here runs through the pressure AI and technical change are putting on how people actually lead. An engineer's exit that exposes what leadership never fixed. A restructuring that strips out managers faster than trust can follow. Five situations, tech focused, but will challenge any leader.
Six more, starting with a count that doesn't add up and ending with a complaint that never got made — and everything that silence cost. Different set, same six-part structure, nothing repeated from Volume 1.