The Great CEO Within

The Great CEO Within

The Great CEO Within is one of those books that I recommend to nearly every startup founder. If you are turned off by the title, don't be! It sounds incredibly corporate and business-speak, but is full of great nuggets on running yourself and running your company. The lessons are short, clearly stated, and full of actual examples. It's hard to imagine a more information-dense read.

If most founders read it 1-2x per year, I think they'd have a much easier time running their companies.

I started reading it again as part of my reading period. For anyone considering starting a company, I think it's worth a read. For anyone who is at a startup, I think it's also worth considering: "what if I were CEO?".

The Beginning

Mochary says the only good reason to start a company is to understand customers, their problem, and then solve it. He borrows this philosophy from Disciplined Entrepreneurship by Bil Aulet. I'm not sure I agree this is the only good one, but it does seem like it'll create the best outcomes.

It's better to have a co-founder (no kidding), and founding teams should not grow beyond six until there is true PMF. The three reasons: morale, communication, speed. Below six, people will meet chaos with glee. Above 10 employees, they expect stability.

All of your initial work should be focused on the prototype that gets you to PMF, not writing industrial level code. This tracks heavily with my experience.

Getting things done

Each day, process every single item in your inbox (email, slack, text). If it takes less than 2 minutes, do it immediately. If not, write it down and place it on a particular list...

  • Next Actions: tasks on your priority list separated by areas of context (Computer, Calls, Outside, Home). Make sure each next action should be written so clearly that you don't have to think about it, you can just do it.
  • Waiting For: the list of things you ask others to do and are waiting for a response. Add the date that you made the request, then you can scan them quickly
  • Agenda: the big idea here is not to worry about doing stuff as one-offs, but instead batch it up into agenda items to discuss. (like what I want to do with Leah and the family meeting)
  • Projects: list for projects that have to be done serially
  • Goals: the place where you have your 10 year vision or OKRs. Sort of like my 2021 Goals doc
  • Review: review everything above

Every day, you should review the following: Next Actions, Waiting For, Goals

Every week, review: Someday/Maybe, Agenda, Projects

Maintain inbox zero. Check email 2x daily, once in the morning, and once in the afternoon. If the email takes less than 2 minutes to address, do it immediately. If it takes more, add it to one of the other systems.

Spend the first 2h of each day on the #1 thing that you have to do (whatever it is). Having this time free of distractions will help you approach the task with energy and vigor.

Committing to agreements

Companies work via a series of agreements. If you ever realize you are going to break an agreement you have to let your stakeholders know. That way they can jump in and help you. If someone stops being able to honor their commitments, that is when they have to leave the company.

Honor everything: if you are going to be late to a meeting, let people you know you'll be late. If you won't hit your goal, let your team (or manager know).

Getting teammates to amazing execution

"Assume you were CEO for the next 90 days, what do you think are the top 2-3 things to do as a company."

Stages of running great meetings:

  • Stage 1: have teammates write up an agenda ahead of time, everyone reads it in the first 5 minutes, then go around to make a decision
  • Stage 2: circulate the document and ask for comments 24h before. do not allow any comments besides those that are in the document
  • Stage 3: only decisions are made.

Conscious leadership

There are only five primary emotions: joy, excitement, fear, anger, sadness. We make bad decisions when we are gripped by fear, anger sadness.

The real trick to leading an effective organization is that you have to approach each situation as a chance to learn with curiosity and exploration.

Exercise: at each quarterly offsite, ask members of the team to share feelings of joy, excitement, fear, anger, and sadness. For the last three, include “what the facts are”, and then “how you feel about them”. You can incorporate these anonymously.

Feedback and tough conversations

People only start feeling conflict if they feel like they aren’t being heard. The solution to this is laughably simple: you need to explain what you’re hearing from them and say “is that right?” If they say yes, you’re done. If not, keep trying to get there.


There should be three types of days:

  • one day of internal meetings
  • one day of external meetings
  • three days of no meetings at all

Which days you pick don't matter so much, but it is important that you have dedicated times for focused work.

For the days of internal meetings, the following order is recommended

  1. 1:1 meetings (read High Output Management)
  2. Leadership team
  3. CEO Open Office Hour
  4. All-hands
  5. Company-wide social event

This way you can adapt smaller format meetings to the broader ones later in the day.

Every meeting should have...

  • an agenda with the stated goal or outcome
  • updates from all meeting participants
  • someone who can lead the meeting and stick to the timeline

There's a pretty basic 1:1 template for each teammate, as well as a template for the leadership meeting. All of them are around "meta-work": giving & getting feedback, reviewing actions and accountability, and raising any issues at the company.

There's a great line for getting feedback from Lachy Groom: "What feedback are you afraid to give because you think it might hurt my feelings? Please tell me that."

Your job with feedback is to then act on it. Don't let it fall into the cracks!