The weekly CEO e-mail

I got this email recently from a CEO:

“Hey Gokul, I want to start a biweekly newsletter to the entire co. I read your blog post on all hands. Was super helpful. Do you have any guidance or examples on how to best structure a regular written update?”

In a previous post, I talked about a company’s communication architecture being the CEO’s most important operational responsibility.

Spurred by the CEO’s request and following up on the earlier post, I’d like to deep dive into a specific element of a company’s communication architecture: a weekly or fortnightly email from the CEO to the entire organization. Most CEOs send emails to their organization on a one-off basis — for instance, to announce an acquisition. However, relatively few CEOs use emails to communicate many-to-one on a regular cadence.

Let’s talk about why the weekly CEO email matters and what it entails.

Why

Why should the CEO send out a regular email to their organization? Aren’t All-Hands enough?

All-Hands are amazing and help an organization accomplish a number of things, but they absolutely cannot substitute for a regular CEO email.

First, All-Hands are not personal enough. The CEO plays a part in All-Hands, but All-Hands are not in the CEO’s voice — they involve many presenters and voices. Employees yearn to understand what the CEO is thinking about, to get inside their heads. Only a few employees do regular 1:1s with the CEO and actually have a sense of what the CEO’s true priorities are, in their voice. CEO emails, if done right, help the CEO “speak” directly and authentically to every person in the organization. It’s almost like doing a virtual 1:1 with every single person in the organization. Every week.

Second, All-Hands are not permanent enough. Some All-Hands are recorded so one can go back and replay them, but in general, they go by quickly, making it’s hard to easily remember later exactly what was said, and to ruminate and chew over the key messages. The email format lends itself to more permanence, something that can be remembered and referenced, something that can be easily forwarded or followed up on.

To summarize, CEO emails trump other forms of one-to-many communication in authenticity and permanence. Period.

Outline

A weekly CEO email has three segments:

• Top of Mind
• Performance update
• Miscellaneous

Section 1: Top of Mind

Weekly CEO emails should always start with a bulleted list of what’s top of mind for you: two to five items. Too many items feels like a laundry list; too few items looks like you didn’t care to put enough thought into the email.

I know what you’re thinking.

Half the things that are top of mind for you are too sensitive to talk about broadly. Our competitor is gaining market share. Our best sales person quit. We don’t have a line of sight to our next round of funding. How the heck do I share those with the team?

Two words. Set expectations.

Let people know ahead of time what is off limits in these emails (and in general, in broad company communications). And then stick to it. But once you’ve defined the boundaries, everything else should be on the table to discuss transparently with your team. You’ve got to trust them.

For example, you might state that you won’t talk about M&A or specific people exits in your missives. That’s a perfectly reasonable boundary to set; both topics are sensitive, deservedly so. However, you need to be candid and transparent on all other topics in your Top of Mind. Your sagging growth numbers. The difficulties you’re facing in retaining top sales talent and what you’re doing about it (without naming anyone specific). Competition. In short, anything that’s Top of Mind.

Don’t worry just about projecting strength. Don’t paper over things that are obviously not working. Your people can smell BS from a mile away. It’s OK to be vulnerable. Ask for — no, welcome — their help, ideas, suggestions.

This is the most important section of the email. Make it count.

Section 2: Performance Update

Every organization has a few critical top-level goals established on a specific cadence (likely quarterly or annual). Every organization also has a handful of strategic initiatives that are critical to the company’s hitting its goals. (If you don’t have these goals or initiatives at your organization, stop reading this article and go set them now.)

The CEO email should give an update on how the organization is doing against these goals and initiatives, in an unvarnished way. In terms of format, I prefer a Red / Yellow / Green grade for each item, with commentary on progress since the last update. If you are unable to assign a grade to something, it needs to be rephrased.

At 100+ person organizations, it’s rare that the CEO has this info at their fingertips. Therefore, this section almost certainly needs to be informed by the people responsible for each of initiative. (Again, if it’s not clear who’s responsible, stop reading and figure that out). Edit these submissions to ensure consistency of tone across these updates, since self-reported commentary can sometimes be overly self-congratulatory or too self-critical.

You’ll also need to put a weekly process in place where you receive grades and commentary from the relevant people far enough in advance, so you can read and synthesize these into a cohesive whole for your email.

Section 3: Miscellaneous

The first two sections are mandatory, and as long as you include these, you will have a strong update. However, I’ve seen a few other items in these emails. These can sometimes be interspersed within the first two sections (especially in the Top of Mind) or can merit their own section.

• Kudos / Props: Collecting kudos from team members and including them in the weekly update can be a high-visibility way to recognize people on an ongoing basis. Definitely its own section, unless it’s a one-off Kudo, in which case it can fit within Top of Mind.
• Questions: This email is a good channel to periodically pose a question to the team, a question you want broad input on. For example: What should we be doing on the partnerships front that we’re not doing today? Fits nicely in Top of Mind.
• New team members: Acknowledging new folks who’ve either started on the team, or will join before the next email. Separate section.
• Customer quotes and stories: If you’ve spoken to customers or have shadowed teams whose job it’s to interact with customers, think about including select quotes (praise or constructive criticism) in your email. This can be a powerful forum to highlight to the company what truly matters — the customer the company serves. A customer quote could be a great way to start off the email, even ahead of Top of Mind. Or it could highlight and emphasize one of the Top of Mind bullet points.
• Review summaries: Any summaries, notes or takeaways from product or business reviews (this is for companies that do formal reviews).

Cadence

I personally prefer weekly emails for two reasons. First, you get more opportunities to “speak” to your team and thus to reinforce the messages you want to get across. Second, in a fast moving company, things do change regularly, though with an undercurrent of foundational things that don’t change much. A weekly email captures both transient and semi-permanent things.

If weekly is not possible for some reason, fortnightly works too. Anything less frequent (eg: monthly) won’t be impactful — twelve emails a year isn’t enough.

Not a CEO (yet)?

Though I’ve used the word CEO so far, this practice doesn’t just apply to them. It’s a good practice for any leader of an organization that is either distributed or larger in size than a few dozen people. If your org is 100+ people, you should absolutely be sending these emails. But you should start evaluating from 25+ people onwards, whether a weekly email makes sense to add to your communication repertoire.

What it looks like

Here’s a sample CEO email template to give you an idea of how such an email might look in practice. Don’t use this exact template slavishly — the tone should reflect your style, and it’s good to mix it up once in a while.

From: <CEO>

To: <Organization>

Subject: <CompanyName> Weekly Update, <Date>

Team:

Happy Monday! Hope everyone had a great fourth of July. I spent the 4th in Austin, Texas, where the temperature hit 110. (Inject customer story)

Here’s what’s top of mind for me this week:

1. Top of mind A: Description. Shout out to (Person) for their analysis on this project.
2. Top of mind B
3. Top of mind C: I know we’re not doing well here, so let me ask all of you — what should we do differently? Please little-r me with the answer this week, and I’ll summarize and send out next week. I am hopeful we can come up with something powerful and radically different.

Now let’s look at how we’re doing against our top-level quarterly goals and our strategic initiatives.

Top-level goals

Goal 1: [Status: Red] Commentary

Goal 2: [Status: Yellow] Commentary

Goal 3: [Status: Green] Commentary

Strategic Initiatives

Initiative 1: [Status: Yellow] Commentary

Initiative 2: [Status: Yellow] Commentary

Initiative 3: [Status: Red] Commentary

As always, feel free to email / Slack me with any questions or feedback, or to set up a quick walking meeting to chat about anything in this email, or anything else at all.

Here’s to a great week — see you all at the All-Hands on Friday.

Thanks

(Name)

Summary

Ultimately, what matters is for your team to hear from their leader — you! — on a regular basis. So: stop procrastinating, and start your updates.

It will take a couple of weeks to get into a groove, to find the right mix of things to highlight, to get comfortable with sharing more and being vulnerable, to put the relevant processes in place, and most importantly, to find your authentic voice. But I promise it’s something that will pay off many times over, through your organization feeling better informed, more aligned and a high sense of camaraderie, trust and confidence.

What are you waiting for?