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The Weekly CEO Update

Leonardo Federico · July 8th, 2020

Most startups are a hot mess.

Once an organization achieves a basic level of product-market fit, chaos dominates everywhere, and the single hardest problem is to keep the entire company aligned.

Before then, all of the employees fit into a single room, everyone knows what everyone else is working on, and founders can easily walk around desks telling everyone what to build and why.

But at around 50 employees, things change and this approach stops working.

Team and departments get formalized under org charts, all-hands meeting are reduced to the minimum, and all sorts of processes and proxies emerges.

All the new levels of hierarchy creates silos and a feeling of compartmentalization. Meanwhile, a lack of leadership for some functions creates a sense of disorganization and chaos.

The job of a great leader is not to resist this chaos, but to counterbalance it by frequently communicating with extreme clarity principles and priorities, so that everyone, no matter roles, department or seniority, knows the company's goals and direction. Good management is a perpetual anti-entropy device.

Most leaders use all-hands meetings as the de-facto tool in their arsenal to keep the company aligned and informed. During these meetings the entire company gets in a room or on a conference call and receives an update in a lecture-style format.

Meetings, more than any other written communication medium, allows the speaker to convey more information, but they can be hard to arrange at scale. This is especially true for remote or distributed organizations where employees work from different locations and time zones.

The most overlooked weapon to keep the company on the same page is a good-old internal weekly newsletter. The obvious example of the category is the Weekly CEO Update Email.

We'll see in this essay not just why every Founder/CEO should send a weekly CEO update email to the entire company, but also what elements are necessary to craft a great Weekly CEO Update.

Why An Internal Newsletter

Why isn't an all-hands enough? We're hyperconnected throughout the day, why should a Founder/CEO even bother adding a new piece to the puzzle? Meetings are a great tool because it's a nuanced medium of communication, but they can't replace a regular well-written email. Here's why:

  1. Written Communication is Personal

Written communication is one of the strongest forms of persuasion.

The wire that stretches from the writer to the reader is singular. The writer creates in solitude, and the reader reads in solitude. It's an intimate relationship. Everything happens silently in the brain as an intellectual dialog between the two parts.

  1. Better Historical References

References made in spoken words are weak.

On the other side, written communication allows you to pinpoint the exact piece of information that you want to reference to. This not only helps the author to write more extensively but also the reader to fully understand the global scope of the message.

  1. Permanent

Anything that's written in words is permanent and searchable. This means everyone sees the same thing, everyone hears the same thing, and everyone will know the same thing - including future employees who are yet to join your company.

Permanence of communication is the prerequisite to a shared truth.

  1. Writing is Costs Effective

Writing saves time.

If you already have a distributed team, you know how hard and time consuming it is to arrange an all-hands meeting.

Plus, as Basecamp puts it,

“Five people in a room for an hour isn’t a one hour meeting, it’s a five hour meeting.”

  1. Inclusiveness For Women and Introverts

Modern work gives extroverts a free power-up that introverts have to earn through time and practice. Meetings favor individuals who think out loud and are good at discussing things on the fly. They aren't fair to those who need time to think things through. It’s an unfair game for a large number of people. Yet, this rarely gets noticed.

How To Write a Great Weekly CEO Update

The outline of a Weekly CEO Update always includes three key elements:

  1. Summary
  2. Performance Update
  3. Misc: Ops and Culture Highlights

Summary

The summary is an introductory paragraph that summarizes what happened the latest week.

A good summary gets the reader's attention either:

  1. By answering a question the reader already has (ie. the company is acquiring a competitor and employees wants to know more about the progress on the deal).
  2. By raising a new question in the reader's mind for which the author is going to provide an answer to (ie reasons why the org chart was restructured and some teams were un-bundled).

If the reader already has a clear question, you can go straight to the point by answering it. Otherwise, you should build a compelling summary that naturally leads to it. Failing at both of these means not establishing the relevancy of your message.

Although not a weekly update, one of the best example of summary is the one sent by CEO Stephen Elop to introduce the call to action for Nokia's need to embrace a non-homegrown platform.

You can read the full memo here.

burning platform internal memo from Nokia CEO Elop

The summary is the most important section of the update.

Performance Update

The performance update is a reminder about how the organization is doing against its most important goals.

Every organization has a few critical top-level goals tied to a set of strategic initiatives. As a leader, you need to solidify this message by repeating it all the time.

So, here's a simplified version of the performance update:

Top-Level Goals:

  • Yearly Goals: current metrics for annual goals and how you’re measuring up against them
  • Quarterly Goals: current metrics for quarterly goals and how you’re measuring up against them
  • Quarterly Priority: percentage complete and any updates to the most important projects

Strategic Initiatives:

  • Activity #1 [commentary]
  • Activity #2 [commentary]
  • Activity #3 [commentary]

If you're thinking "Wait, do I really need to state our top level goals in every single update?", the answer is YES. The minute you start to get sick of hearing yourself to often, your people are just starting to internalize it.

https://twitter.com/rands/status/1278735543019270145

Misc: Ops and Culture Highlights

The end of your update is the perfect place to share details about people and operations.

Specifically, you want to cover with these three sections:

  • Operations: new processes or procedures (eg. a new Slack etiquette, a new remote work policy, new room procedure, or new habits that you are trying to inculcate generally)
  • Culture Highlight: share topos, stories or examples from the week that project the company culture
  • People spotlights: give exposure to members of the team and expose their work to the entire org

Feel free to adapt this section to your own needs and rituals.

The Cadence

The goal of the Weekly CEO Update is not just to inform, but rather to create an operational cadence for the entire company. Frequent, well-written updates = high-performing, intense pace. Occasional, poorly-written updates = low-performing pace.

A daily update can be too much information. A monthly update can be too little. A weekly update is usually what works best, but depending on the circumstances every cadence would work.

Pick a cadence that not only captures the rhythm of the organization but actually reinforces it.

The Medium

Don't send an email for the weekly update. Email is a decentralized form of communication. That means that there's no permanent record in a permanent place everyone can see.

Similarily, avoid Slack messages. Chat is great for quick and casual conversations, but it's not the best way to share interne memos and announcements that are more than one-line-at-a-time jousts.

Instead, you should post it in a place where the message can be easily retrieved if you wanted to. Everyone should see, hear and know the same thing – including future employees who are yet to join the company.

I shared here and here how companies like Automattic and Zapier are using tools like Async and the Wordpress P2 theme for asynchronous communication.

Using Pulse For Long-Form Updates

Pulse is a stripped-back async work tool that can help you do just that: share long-from updates to keep your team on the same page.

Pulse Editor With Internal Memo

We’ve specifically designed Pulse from the ground up to support updates across projects, processes, decisions, strategy and more. The type of comms that this product enables can range from global announcements, project proposals, and feedback on processes to welcoming new employees and discussions around long-term endeavors.

But let's go back to the Weekly CEO Update usecase.

The best way to share a Weekly CEO Update in Pulse is to start by creating a dedicated Stream.

CEO Weekly Update Stream in Pulse

People in your organization can follow the Stream and read your Weekly Updates directly from the Pulse Website or (once you installed the Browser Extension) anytime they open their browser's new tab.

Let's look at some real examples.

Jason Lemkin used to run an internal publication called The Daily Jason where he sent every morning an email to the entire SaaStr team. The Daily Jason's Update always included the top 3 priorities for the week and how the team was measuring up against them.

You can learn in this quick video Jason talking about it:

In Pulse he would have created a @daily-jason stream and shared there every morning an update. The team would have been notified either by Slack, Email or the Browser Extension.

What's benefit of using Pulse over Email, Slack or other decentralised communication channels?

  1. Updates are permanently recorded in a fixed place not just your current team members, but also for the future ones who are yet to join the organization. This approach makes it super easy for a new employees to immerse in the company tone and culture, and understand how your company operates. A much better experience than digging in organized Slack channels.
  2. You, as a leader, can reference updates previously published by your team, in the next weekly update. For instance, Jason could have linked all the individual accomplishments that the SaaStr team achieved in the previous days to hit the week's top priorities. People can click to expand the individual updates and read them beyond its title in case they missed something meaningful. See the quick video below for more.
  3. You can then backtrack where a specific pulse has been mentioned. In pulse we call these linkbacks. At the end of the update we show a list with of all the posts that contains a reference to it. This makes it very easy for leaders and individual contributors to always see the broader scope of every action and keep everything in perspective.

A short video with Pulse a Pulse Weekly Update and relative references & linkbacks

SaaStr is not the only company where leaders run internal publications. On a similar note, David Cancel at Drift and Mathilde Collins at Front both have been running similar weekly newsletters for quite some times now. I wrote about them in Operations and Internal Communication for Founder/CEOs.

Conclusions

The truth is that constant, relentless, well-written communication is hard.

You need to work hard to make it part of the daily routine for yourself and the stakeholders in your company.

As Gokul Rajaram at Square said in this great essay:

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.

If all goes well, six months later, you and the team will be celebrating a needle-moving win rather than trying to figure out what went wrong.