Win the week

Yesterday, I had a meeting with Andrew. (Sadly, on Zoom.)

We’re about six months into his tenure as CEO of Bootstrapped Giants, and he's doing a fantastic job.

In that time, he's added ~10 sponsors and he’s done tons of work with them. We have 60 people in our first accelerator. From what I can tell, it's getting rave reviews - and we’re just getting started.

One of the things that makes Andrew great is he is Mr. Get Shit Done.

He’s one of those people with endless energy. He dives in and grinds.  He cares deeply about doing great work and jumps from thing to thing.

In the early days, this is SO important to get things working.  You just have to blitz things in front of you until you crack them open.

We launched the Accelerator with little more than a video that he recorded on his Mac’s Photo Booth app.

He got Superhuman to partner with us on their launch promotions because he picked up on a random tidbit their Marketing Lead mentioned when she said how her day was going.

While I'm applauding Andrew now, our meeting had a different tone.

I spent some time pushing him to get organized.  Specifically, to "win his week."

I'm guessing like Andrew, you are an energetic doer who can move heaven and earth by digging in.

This can be a challenge because it becomes tough to scale/build a machine that will grow continuously. 

Entrepreneurs get tired/stressed, teams feel confused and things stop working. 

It's often the difference between a frantic 7-figure business and a calm 8-figure one.

There's a ton written on the importance of a thoughtful communication infrastructure.  Here is my favorite article by my friend Gokul Rajaram.

I want to get even more tactical.  Here’s what I suggest!

Dedicate at least 2 hours of work time. Here’s the way I’d break that down.

Spend ~1 hour to get to inbox zero. Be sure to catch up on everything and see it all. Use a defer/remind feature when needed.

Then, take 30 minutes to write out your top weekly priorities. 

Ideally, this is in the format of "What I want to be true by Friday."

Then, for another 30 minutes, ensure your calendar aligns with those items.

Ideally, by late morning you have all critical reporting from your team across marketing, sales, customer service, recruiting, etc. 

You have some infrastructure to tell you whether that is "good or bad" (ie.. are you tracking or not to where you want to be?).

Outside of your 3 priorities from yesterday, this will inform how you spend time that week.

In the afternoon, I want you to meet with your leadership team and potentially any other meetings that serve your top 3 priorities.

Focus on your priorities and the issues that need attention.

Some people like standing team meetings for marketing, sales, etc.  You can deep dive into creative/new initiatives and go deeper. 

I recommend letting the teams have standing times. BUT - you choose whether or not to attend based on if something is tracking or not.

If something isn’t tracking, attend to it. If it’s one of your priorities, attend to it.

If not, spend your time on things that are included in those priorities. 

I'd also try to organize external vendor/recruiting meetings during these two days.

This can be a good day to take a “slow thinking morning.”

This could mean "deep work" (I've never been good at deep work, but I'm trying!)

Maybe do vision work with yourself or the team.

Whatever it ends up being, make sure you blocked out time for this in your schedule.

Thurs afternoon can be for your direct reports 1x1 - learn how to run great 1x1s first in a formal way and then over time, let them become more informal.

These touch points are important, so prioritize them!

I like to keep this day open for exactly 2 things:

1) Communication

Checking in on teams, sharing information across teams, seeing how the week is closing up, and an extra nudge…

2) Offense

Meeting people who don't fit in my priorities but seem interesting. It could mean extra offense on an idea.

That is my 80/20 direct suggestion for a CEO on how to organize their week.

People THRIVE on schedules and predictability.

It's true for babies and kids. It’s true for adults and true for companies.

Knowing what to expect and having a rhythm helps things get done in a more orderly and consistent fashion. Create this rhythm and honor it.

One of my favorite Steve Jobs stories was that Apple was entirely organized around him.

He would meet execs on Monday, product/engineering on Tuesday, sales/marketing on Wednesday, ops/logistics on Thursday…

This created an entire system that played into people reporting to Steve knowing those were the days he'd focus on that item.

Adriane (GrowthAssistant co-founder + CEO) often tells me I give advice that seems conflicting, but it’s important to allow for nuance.

So following up on the importance of honoring a routine, I’ll say this: sometimes you need to blow up the routine.

That might mean there's a huge opportunity that needs everyone's attention. Or something is on fire, or something just isn't working.

Honoring is important, but it's not set in stone. Your job is to know when/how to evolve it.

I love all tools. 15/5, EOS/90, OKRs… all are great.

My rule with software/systems is THE BEST ones are the ones YOU WILL USE.

Sometimes, a whiteboard is better than a CRM software. But other times, you do need that CRM!

The same goes for all these tools. 15/5 can work. But so can a 5-minute phone call on Friday morning to check on how people are doing. There’s no right or wrong here.

One of my favorite ones is a weekly email from the CEO internally recapping everything that is happening.

It can be co-written with the COO/chief of staff. But I find it to be a great alignment/reflection mechanism. I've included old examples of mine.

Last, but not least, the Sprint.

It comes from the old engineering paradigm. But it's a VERY effective way to get a lot of work done while remaining flexible and reflective.

It won't ever be perfect, but it's a great system to leverage!

That's all from me - go win your week!

-jesse