New to leading people?
Start the 12-month plan in January. One book a month, one action a month.
The 2027 Leadership Reading Plan
You can't debug people. Trust me, I tried.
I read a lot of books trying to figure out why being a manager was so hard. Some were amazing, others… not so much. Here are the ones worth your time.
How to use it
Leadership is universal.
None of these books are written for MSPs, and that's the point. Leadership works the same in an MSP, a bank, or a plumbing company. The people problems don't change because the tickets do.
Already running the show?
Start with the executive five below. They're the ones I'd hand you first.
Don't just read.
Every month has a "do this." The book is the input. The action is where you actually get better.
Top 5 for existing executives
Already running the business?
These are the five I'd hand you first.
The Advantage
Most companies don't fail from a lack of smart people. They fail from a lack of organizational health. This is the operating manual for fixing that at the top.
The Hard Thing About Hard Things
For the decisions no framework covers: layoffs, firing a friend, holding the company together when the plan falls apart. Honest about how lonely the job gets.
Thinking in Bets
Stop judging decisions by how they turned out. A good decision can have a bad outcome, and a lucky one can teach you exactly the wrong lesson.
Good to Great
Discipline, the right people in the right seats, and the humility to face the brutal facts about your business.
The Infinite Game
Business doesn't have a finish line. Leaders who play for the quarter burn out their people and their clients. Leaders who play for longevity build something that lasts.
The 12-month emerging leader plan
One book a month. One action a month.
Built in the order I wish I'd read them. Q1 is intentionally the easiest reading of the year, because most plans die in February.
Q1 You're not an engineer anymore
Managing Humans
Written by an engineer for engineers. It's the bridge from "I'm the best at the work" to "the work is now people," and it speaks your language while it does it.
Do this Write down the three things you did as an individual contributor that you need to stop doing. Hand one of them off this month.
Extreme Ownership
The mindset flip. Everything on your team is yours now, including the parts you never touched. No excuses, no blaming the client, no blaming the last guy.
Do this Pick one thing that went wrong on your team this month and own it out loud in your next team meeting. No "but."
The Motive
Are you leading because you want the title, or because you're willing to make the hard and unpopular decisions for the greater good?
Do this List the decisions you've been putting off because they'd be unpopular. Make one this month and explain your reasoning to the team.
Q2 Build the team
The Five Dysfunctions of a Team
What a team actually is, and why yours probably isn't one yet. Everything else this year builds on trust and healthy conflict.
Do this Score your team honestly on each of the five dysfunctions. Fix the bottom one first, since it's the foundation for the rest.
The Ideal Team Player
Hiring is the single most important decision you'll make as a manager. Every other problem on your team gets easier or harder based on who you let in the door. Humble, hungry, and smart gives you a real filter instead of gut feel and resumes.
Do this Rate yourself on all three, then every person on your team. Add one question for each to your interview process.
Turn the Ship Around!
Stop being the smartest engineer in the room. Push decisions down to the people closest to the work and stop being the bottleneck.
Do this Pick one decision that always routes through you and give it to your team. When they come to you, have them say "I intend to" instead of "What should I do?"
Q3 Have the hard conversations
Crucial Conversations
The conversations engineers avoid are the ones that turn into resignations, escalations, and lost clients. This is the playbook for having them before it gets to that point.
Do this Have the one conversation you've been putting off. Prepare for it using the book, then have it this month, not next.
Radical Candor
Feedback that's honest without being a jerk about it. Most new leaders are either too nice to be useful or too blunt to be heard. (Can you guess which I was? =D)
Do this Give every direct report one piece of specific praise and one piece of specific criticism this month. Then ask each of them for feedback on you.
Dare to Lead
You don't have to have every answer. Teams trust the leader who admits what they don't know, not the one pretending.
Do this In your next team meeting, name one mistake you made this quarter and what you learned from it.
Q4 Lead like you mean it
Death by Meeting
Your calendar is your job now. Bad meetings are a tax on the whole team, and you're the one setting the rate.
Do this Audit your recurring meetings. Kill one, shorten one, and give the rest a clear purpose.
Necessary Endings
Growth requires pruning: the project that's going nowhere, the process nobody follows, sometimes the person who isn't working out. Decide what to cut before next year starts.
Do this Write down one thing your team should stop doing in the new year, and end it before January.
The Dichotomy of Leadership
The graduation book. Lead but follow, be confident but not cocky, own it but delegate. It only lands after a year of feeling those tensions yourself.
Do this Look back at the year. Write down where you overcorrected, then build next year's plan around balance instead of swinging back the other way.
Now what?
Read one. Then do the thing.
Got a book you think belongs on this list? Tell me why I'm wrong. Best answer gets a free beer at the next show.