The CEO's Personal Management System
Welcome entrepreneurs. I’m so glad you’re here.
A perk and privilege of my work is I get an intimate look into the habits and systems of leaders from across the world. When I began coaching, I expected to see as many variations as there are leaders and companies, as leadership is such a personal journey. But after coaching hundreds of CEOs, I’ve learned that despite differences in geography, stage, and sector, many effective CEOs approach their days very similarly.
I thought it a worthwhile endeavor to catalog that pattern, not as a prescription that you must follow, but as an aggregate datapoint of the similar conclusions that many CEOs have come to on their own.
I have found myself following a similar pattern to the one I will outline below, and I have come to recommend these two tools to leaders I work with. That said, like all advice about building something that matters, leaders, the following is yours to accept, reject, or steal from as you see fit.
The scale-up CEO’s Personal Management System
The CEO role takes place at the frontier. Every day, leaders of companies seek out the areas of their businesses that are the most uncertain, and apply their work there. To manage this degree of uncertainty, the top CEOs add systems two specific areas of their days: their calendars and the way they manage their to-dos.
Calendar
The most common schedule I see is one that is split into three parts: Saw sharpening, Deep work, and Meetings.
7-8:30am – Saw Sharpening (Prioritizing self-care for CEO’s)
It is uncommon these days for a CEO to report that they have no form of regular self care. In fact, when someone says they don’t have a set of regular practices dedicated to ensuring they’re on the top of their game, that’s generally the first thing we work on.
But it’s more than just walking through the practices. The most successful CEOs I’ve worked with prioritize this part of their day. They sharpen the saw first, and they generally don’t miss a day.
What I most often see is a period of time, usually immediately after waking, in which they go through a patterned series of practices that can take anywhere from 30-90 minutes, independent of how early they wake up. The most common practices are exercise, meditation, and journaling, but I also see any number of other practices, from reading, to breathwork like Wim Hof, to walking the dog without a phone. The specific patterns are varied. What’s consistent from leader to leader is the presence of a highly patterned and regularly repeated series of practices.
9-11am – Deep Work (Mastering deep work for growth)
I know many CEOs who lament the fact that they rarely get a chance to work on the growth of their businesses, because they’re so inundated with the reactive crap that gets thrown at them all day. Meetings, fires to put out, emails, etc. As a CEO it’s endless.
But the best CEOs deal with the same or higher volume of inbound noise, and as a rule make time to work on the growth of their businesses. How do they do this? They consciously prioritize their own deep work over firefighting by carving out a dedicated block of hours every week to only work on their own most important, growth oriented things.
My clients have experimented with many versions of this. Some prefer to have a single, meeting-free day, and some prefer to have a bunch of smaller chunks of dedicated time. But the schedule that seems to work the best for most people is to carve out 2-3 hours, every day, immediately upon getting to work, and dedicate this time to working on only the thing that is most important to the growth of your business. Two hours - before email, before meeting prep, before employee issues. Period.
Implementing a structure like this can take work, particularly if you have a large team that is still somewhat dependent on you. Which is why the rigor of it is so important. It’s easier for teams to adjust to clear rules like “I’m only available for emergencies from 9-11” than it is to ask them to read your mind, do it ad hoc, or completely ignore you for an entire day.
11-EOD – The Rest
There’s a reason the military has every soldier make their bed first thing every morning. It sets the tone for a productive day. Having similarly set the tone with their early work on the most important thing, the rest of the day is spent on meetings, calls, strategy sessions, firefighting, and everything else.
Parkinson’s law states that the work will expand to fill the available time and space. When I bring up the idea of packing all the reactive and logistical stuff into a little over half a day to someone who hasn’t thought like this, it’s common for people to push back. “That’ll never work,” they say. “I just have too much to do.”
Trust me. They’re wrong.
One of the things you learn as you grow in your leadership career is that your workload never decreases. You just get better at delegating and leading. Having less time is an incredibly effective forcing function to cause you to level up your leadership, empower your people, and build your organization (rather than your ability to work ever harder).
To-dos
Leaders use all sorts of tools for todo management—from sticky notes to holistic frameworks like Pomodoro or GSD—so it doesn’t appear that one toolset is generally better than another. Different strokes for different folks. But what I have seen is that the CEOs who are the most effective at managing their own output 1) take care to separate the planning of their to-dos from the execution of them, and 2) are generally way more rigorous about planning their to-dos than your average leader.
Separating planning from execution (Strategies for effective to-do list management)
The most effective to-do planning process typically has two components: a weekly triage and a daily triage. The goal of the weekly triage is to identify and stack rank the tasks that are the most important to fit in during the week, and the goal of the daily triage is to identify and stack rank those tasks that are the most important to fit in during the day. No surprises there.
But the best CEOs do something very particular with their tasks, during both of those planning processes. Once they’ve stack ranked the tasks in order of importance, they also choose which of those tasks will NOT fit within the given time frame. And then they remove those tasks from that week’s/day’s list, to be triaged during the next cycle.
Whereas many people simply allow their to-do list to become infinite and check off what they can, these founders are regimented at trimming their to-do list to fill up only the time they have available, allowing them to actually, believe it or not, reach a point at which their work is done for the day, more days than not.
That’s worth repeating. By following this method, you have the opportunity to be done with your work at the end of the day.
The most effective process generally works like this.
Weekly:
Stack rank your to-dos for the week
Look at your calendar and identify which windows you have available to work on those to-dos (hopefully at least 2 hours per day, if you’re following the system above)
Slot the most important to-dos into the windows where they fit, resisting the urge to cram more than will fit.
Move all todos that do not have a dedicated and adequate time slot for their completion to the next week’s triage
Daily:
Stack rank your to-dos for the day
Consciously move all to-dos that do not fit within the time slot available during the day to the following day’s list
Complete the to-dos during the windows allotted for them. If you finish, you are done.
If you do not finish, roll remaining to-dos to the next available day
Then you execute, and you find out that you either estimated well, or estimated poorly. And that gives you data to iterate on the planning process for the next week. Planning your to-dos realistically is a learned skill that many top founders have become incredibly good at.
I can hear some of you thinking: “yeah that’s some wussy shit.” And I see you with your neverending todo lists and your hustle. And I’m here to tell you that this method will allow you to get more important things done, more quickly, and more sustainably, than the way you’re doing it now.
Firstly, by forcing yourself to do the hard work of cutting certain todos that don’t fit within the week, you develop the competency and comfort with making hard decisions regularly between worthwhile efforts. Through this method, you must say “no” to important projects each day and each week, forcing you to be disciplined with your prioritization, and ensuring you’re only working on the most important things.
Secondly, in the marathon that is building a company, it turns out that EOD downtime, combined with a consistent sense of accomplishment at the end of each day, actually increases your feeling of momentum. It seems that feeling like you’re winning actually causes more motivation than feeling like you’re behind and failing all the time. Who knew?
Conclusion and next steps
The CEOs I work with are as varied as any other group of people. They’re human beings, and what works for one human being won’t necessarily work for another. The model above doesn’t remove your obligation to think critically about which methodology works for you, and to iterate on processes until you find and create one that fits.
That said, the journey from founder of a company to CEO of a scaling startup requires a great deal of change on the part of the individual, and it would be silly not to learn from best practices.
I hope you found this useful, and would love to hear about any other techniques or strategies that you’ve found useful for yourself. If you are using any of these methods, I’d love to hear how it’s working for you. And, if you’d like support in implementing this, we’ll be releasing a Notion template for that soon. Shoot me a reply and I’ll make sure you get it when it’s ready.
Want to dive deeper?
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Executive Coaching for Entrepreneurs
There’s a reason every elite athlete in the world works with a coach. You need more than one perspective to see your best work.
I’m an executive coach and the founder of Inside-Out Leadership, a boutique leadership development agency that supports entrepreneurs to step fully into their lives, and transform their companies into their masterpieces.
Leveraging 15-years as a founder/CEO, along with deep training in mindfulness, psychology, Neurolinguistic Programming, psychedelic integration and more, I have helped leaders from some of the fastest growing companies and VC funds in the world design a more conscious life and make key changes to improve their performance and satisfaction.
I coach leaders how I want to be coached:
Focused on the person, not the role.
Focused on results, without the fluff.
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