How I Plan My Week as a CEO

Editor’s Note: How My Planning Has Evolved Since 2017

Last updated: February 2026

I wrote this article almost nine years ago. Reading it back, I can see how much my planning has changed, but also how much has stayed the same.

The five metrics I mentioned (Thinking Time, meeting influencers, customer research, recruiting, deep work) are still the foundation. But the way I track and act on them is completely different now.

Back in 2017, I was tracking everything manually in OmniFocus and a spreadsheet. Now I use a combination of Notion for high-level quarterly planning and a simple weekly template that takes me about 20 minutes to fill out every Sunday night. The template has three sections: what went well last week, what needs to change, and what’s the one leading indicator I’m pushing this week.

The biggest lesson I’ve learned since writing this: leading indicators matter more than outcomes, but you have to pick the right leading indicators. Early on, I tracked “number of meetings with influencers” as a metric. That was fine, but I eventually realized that the quality of those meetings mattered far more than the quantity. Five meaningful conversations with the right people beat 20 surface-level coffee chats.

I also added AI to my planning process recently. I feed my calendar data and task completion history into an AI tool and ask it to identify patterns. Things like: which days am I most productive? Which types of meetings generate the most follow-up actions? When do I tend to skip deep work? The patterns it surfaces help me plan better weeks.

The core advice in the article below still holds: your planning process should evolve as your role changes. What got you here won’t get you there. And the only constant is change.

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[Original article starts: “Let’s talk nerdy today…” and continues]

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Let’s talk nerdy today. One of the quirky things about me is that I love my boring Sunday nights.

Don’t you just love doing weekly reviews on Sunday night?

Don’t you just love building and fixing systems right before an episode of Game of Thrones?

What about planning your ideal week ahead?

I love all that stuff. The only thing I don’t love is Game of Thrones.

Before you kill me, it’s because I’ve never watched an episode of GoT.

I’m sure I’d love it but I have an irrational fear: with my addictive personality, I’m afraid I’ll binge watch it and never get anything productive done.

Am I crazy?

I know we all have our irrational fears. My ex-girlfriend would never close the door of a fitting room because she would be afraid being trapped and dying from hunger.

I know, makes no sense! But that’s what irrational fears are.

Now let’s get back to being nerdy because that’s the rational stuff you and I can talk about. Specifically, let’s talk about planning the perfect week.

I used to be a huge nerd about this. Every Sunday, after my weekly review in OmniFocus, I would put on my Asian conical hat and plot world domination for the upcoming week.

It used to be a really simple process:

– After my weekly review, I would know all my tasks that needed to be done for the upcoming week. – I would put those on my calendar. – Review everything else on my calendar.

As a productivity nerd, I have literally tried every approach under the sun. I knew that if I could nail down a productive day…then I could repeat that for another day. Before I knew it, I would have an uber productive week and over time be superhuman.

I’ve literally tried everything such as:

– Make certain days focused on specific themes, e.g. Monday = writing, Tuesday = learning, Saturday = only fun etc. – Schedule every 30 minutes on my calendar. – Not scheduling anything at all and see what happens. – The 12 Week Year with weekly check-ins

You name it, I’ve tried it.

After trying so many things, I don’t think there’s a right or wrong approach.

If there’s one theme or pattern that might be “wrong” it is to NOT use a calendar. I can’t imagine being able to plan ahead without a calendar.

(If you’re not using a calendar or have trouble sticking to one, here are a couple resources for you:

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How to Use Your Calendar – 7 Tips for Using Your Calendar More Productively – How To Use a Calendar and Task Manager Together

Seriously, get on it as if fried rice was about to run out.)

Based on my own experience and observation of people involved within the AE community, it’s normal that your planning routine changes as your life changes.

When you grow, you’re faced with different challenges and opportunities. The problems I was dealing with 3 years ago are different than what I’m dealing with now.

My “role” has changed quite a bit. In 2010, I was still cracking the code on making rituals consistent and one of the ways I worked on that was scheduling them on my calendar. Today I don’t have that challenge anymore so it’s not part of my weekly planning process.

Today as the CEO of a growing AE company, I’m dealing with totally different challenges and opportunities that require for me to change my planning. My main challenge right now is spending enough time thinking and meeting influencers. When I’m planning world domination on Sunday night, I’m figuring out ways to spend more time thinking about where AE is going and who I need to spend time “networking” with to make that happen faster.

In the past, a lot of activities that I would plan for would be tied to a certain goal or outcome. If I wanted to lose 20 lbs by summer I would plan to exercise four times a week on my calendar.

What I’ve noticed now is as the CEO most of the planning I do aren’t tied to outcomes at all. The planning is focused on the 80/20 activities that don’t have short-term results but long-term impact. Such as:

– Thinking time – Meeting with influencers – Customer Research – Finding and recruiting people to come work for us – Deep Work

These are five metrics I will track and review on a weekly basis. On Sunday night, I will pick one of the five to focus on for the upcoming week. I will spend about one Pomodoro thinking about ways to improve the metric.

Let’s say it’s meeting with influencers. The metric I have for this is “number of meetings”. This could be a coffee, lunch, dinner, Skype call and such. The more face-to-face meetings I can have, the more value I can create down the line.

However, there are many activities that can lead to successful meetings. For a week, I might do one of the activities:

– Go to my Facebook and try to reconnect with people I haven’t talked to in a long time – Cold email 25 people I don’t know personally but I want to connect with – Research which seminars, conferences or masterminds I can attend to meet people

As you can see, not all of these activities will directly lead to increasing the number of meetings with influencers. I do know that the more time I spend on “outreach”, the more likely I will increase my metric of “meetings with influencers”.

This is essentially what a leading indicator is. They’re activities you can push and influence to increase a metric.

Most of my planning revolves around pushing all the lead indicators as much as possible. Every week my intention is to push one of the leading indicators as much as possible.

On a monthly basis, I’m looking for every metric to improve as much as possible over time. A lot of months the metrics look the same and then sometimes I’ll see a spike in one of them. When you hear people say “Trust the process” (not the 76’ers fans – go Lakers!) this is an example of that. As long as I keep pushing the leading indicators, over time the metrics will improve.

Think of it as losing weight. When you start exercising a lot you often times don’t see the scale move at all even though you’ve been exercising four times a week! If anything, sometimes it goes up. This can be frustrating and discouraging. When you just look at the scale, you’d be frustrated. But if you look at the leading indicators, in this case number of times you workout, you just have to trust the process. As long as you keep working out, the excess weight will go away.

It’s the same thing with planning my weeks. Most of the time my metrics don’t improve at all but I know as long as I’m putting in the work on my leading indicators, good things will happen.

It’s a very different mind-shift I had to make. I used to be obsessed with hitting targets and achieving certain numbers. Now I sometimes feel like I’m shooting in the dark. I had to learn that as long as I trust the process and push my leading indicators, things will be okay.

As I said earlier, this planning system is still raw and needs some tweaking. Eventually, I’ll make this system public inside the Dojo (our private training library and community). This is where release all our best, cutting-edge materials that our community gets access to.

I hope this gave you some insight on how my planning has evolved over the years. As my role and work has changed, so has my planning.

This will apply to you too. Seriously, this productivity pr0n never stops. As you grow, you’ll run into new opportunity and challenges. What got you here, won’t get you there.

The only constant is change.

And that’s why Kaizen is one of our core values at AE – we’re always growing, improving and making things better. You will too.

Let’s glow green this week.