This is the One Email Every CEO Should Send…Every Week

Here's How To Craft a Weekly CEO Update Newsletter That Builds Trust, Creates Alignment, and Keeps Everyone In the Loop On What Actually Matters Most
bad internal comms

“I’m a crappy communicator. There, I said it…”

That was the opening line to my very first CEO Update Newsletter

It was embarrassing to write those words, but I knew they needed to be said if I was going to have any credibility with my team. The fact is, I had failed…badly.

At the time, our company was experiencing rapid expansion.

In a matter of months, we went from a small team that could fit around a meeting table to a large organization where I wasn’t even on a first-name basis with everyone who worked for me.

In short, we were no longer that nimble little team that could gather in a conference room for ad hoc meetings every time something needed to be said.

Our team was growing and our communications were crumbling.

The day-to-day tasks were still getting done, but somewhere along the way, we (and by we, I mean I) lost track of the overall strategy and vision. All the big picture stuff was getting lost under a mountain of tasks, meetings, and distractions, and no one was quite sure what they were supposed to be doing and why it mattered.

This was a big problem, because as CEO, it’s quite literally my job to drive and communicate the vision.

I think Ben Horowitz, said it best…

“Perhaps the CEO’s most important operational responsibility is designing and implementing the communication architecture for her company.”

– Ben Horowitz

…and the fact is, I was failing at this critical duty.

So, as a way to help you learn from my mistakes, I want to share the single most important tool that helped me communicate better—The Weekly CEO Newsletter.

In this post, I’ll walk you through…

  • How I build out our internal newsletter
  • What I include in each issue, and
  • How often I send it out

Let’s dig in…

How to Build a CEO Newsletter

Before I get into the recommended format for the weekly CEO Newsletter Update, I need to give credit to the three people who inspired it.

The first David Cancel who demonstrated the value of a weekly CEO newsletter. The second is Gokul Rajaram whose medium post inspired the overall structure of my newsletter, and the third is Mathilde Collin, Founder and CEO of Front, who inspired me to be more transparent and to use the weekly CEO Update Newsletter as a mechanism for discipline and accountability.

Big, big thanks to you, all.

Now, let’s get into the structure.

There are 4 main sections I include in every week’s issue…

  • The “Top of Mind” section
  • The “How We’re Doing” section
  • The “What Your Working On” section
  • The “Encourage Feedback” Section

Let’s break them down…

The Top of Mind Section

I like to start out the newsletter by talking about what’s been on my mind. That may sound a little arrogant, but chances are, if it’s top of mind for the CEO, it should be top of mind for the team.

This section can be written in paragraph or bullet points, but the idea is to highlight only the most important and critical topics, such as:

  • New product/feature launches
  • Major policy changes
  • New executive hires
  • Changes/pivots to stated goals and strategies
  • Big wins and accomplishments…

…you get the idea. Just keep it short and keep it sweet.

And remember, if everything is important, nothing is important. So pick the 1 – 3 most important things your team needs to know, and leave the rest for the next section…

The How We’re Doing Section

Next, I like to review how the company is doing as a whole.

This is the part that your team will really care about it, because whether you realize it or not, “How are we doing?” is the question that’s always on everyone’s mind.

My advice: Just tell it like it is and avoid spin.

Nothing…I repeat NOTHING…will kill a culture faster than a delusional or dishonest leadership.

So while you can certainly add context, try to keep it to the facts. For example, here’s how I updated the company recently when we fell behind on one of our stated quarterly objectives…

GOAL #1: Add $50k in new MRR by the end of Q3.
STATUS: Behind (but still able to catch up)
– COVID had us playing catchup, but things are back on track
– The new onboarding flow is showing promise…activations are up 35% MoM
– 3 webinars planned for Sept. should close the gap, but I won’t sugarcoat it…we may miss this one

NOTE: Hopefully, this goes without saying, but your company should have stated goals, rocks, key initiatives, or whatever you like to call them. If you don’t, check out this article to learn more about how we do strategic planning and goal-setting at The Scalable Company.

The What You’re Working On Section

This is your chance to get a little personal.

Every once in a while, My team asks me what I’m reading, or what podcasts I consume.

I also often find myself reading an article that provides a key insight or breakthrough and think “YES! Everyone on the team should read this!

This section is the place where I answer those questions and share those articles.

The Feedback Section

I always like to include a request for feedback, even if it’s something as simple as…

Please pass any questions or thoughts onto me, personally. Whether you grab me in the office, or drop me an email or Slack message, just know that I’m here. 🙂

It can be true that a request from the CEO for feedback doesn’t always elicit the most honest responses, but by asking for feedback, you’re laying the foundations for a culture of trust.

For a deeper dive into each section, check out this post.

Oh, and while we’re at it, you’re probably wondering…

What Software Do I Use to Build Out The CEO Newsletter?

Funny you should ask…

I’m very happy to say that we’ve built out our own Remote Communication Software, called Recess.

For the sake of transparency: Yes, we own this brand, but we’re also a very happy customer. 🙂

You can learn all about Recess and get access to the CEO Update Template, here. This is the exact template I use every week to build our own newsletter, and now my template is your template.

Ok, now for the big question everyone always asks me…

How Often Should You Send Your CEO Newsletter?

This one is pretty simple…

Weekly is best. Monthly is the absolute minimum.

But you must be consistent if you want to be effective, so pick a send frequency (even if it’s monthly at first) and stick with it.

And with that, you’ve got everything you need to build out a CEO newsletter that keeps you focused on the big picture, and your team in the know.

Don’t forget to check out Recess and get the deep-dive review of the CEO Newsletter Template here!

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