The Founder's Communication Cadence: Weekly, Monthly, and Annual Habits That Drive Results
I believe it's critical for a CEO to be an effective communicator. They must convey their vision and strategies externally to customers, influencers, and investors, as well as internally to their teams. One of the most impactful ways to do this is through written communication, such as monthly investor updates, internal goals, project updates, or annual shareholder letters. This becomes especially vital during times of change when alignment and motivation are paramount.
I recently listened to an episode of the Founders Podcast (which I love), where David Senra reviewed Jeff Bezos’ now-famous shareholder letters. Bezos’ letters are a masterclass in clear, strategic communication and long-term thinking. You can find a comprehensive collection here: Jeff Bezos' Shareholder Letters
This topic has been on my mind even more lately, with the recent wave of CEO letters around AI—such as the internal memo from Tobi Lütke at Shopify, where he made it clear that AI adoption is now a core expectation for all employees. You can read it here: Tobi Lütke’s AI Memo at Shopify
Other great leaders write some great annual shareholder letters that outline where they think the market will go and how they and their companies will participate. Check out a few of my favorites here:
I’m a big believer in maintaining a consistent communication cadence—weekly, monthly, quarterly, and annually:
- Weekly: Keeps teams aligned on immediate priorities and moving toward near-term goals. For most of my teams, we do this in Notion or Coda, with the updates organized in reverse chronological order, the newest ones at the top. This also allows a new person on the team to see where we’ve come from over a short period.
- Monthly: Offers a chance to review progress, KPIs, and react to shifting market signals. Internally, this could be goal setting or realignment; externally, a good investor update with KPIs, accomplishments, and plans for the upcoming month. Externally, this is a good chance for investor updates. I particularly like the structure of;
- Business summary (what we do) (using CVFB) and notes if any major changes - this reminds the reader of over all focus
- KPIs - how is the business going (if sending to a big group, this can be more about customer traction, usage...vs. pure financials) but good to set the context of scale
- "Did" - what we achieved this month. (3-7 bullet points on customers, product (include video demos), team, GTM...
- "Doing" - what we plan to achieve the next month
- "Need help" - includes brief requests for an investor to take action. Make these easy. For example, if you are looking for customer intro's have a forwardable email body in the message. If you want input on a product, link to a survey form...you get the point.
- Draft this on the first Friday of every month! Send it on Saturday or Sunday morning, when most people get fewer emails and have the weekend to engage.
- Quarterly: Provides time for reflection to evaluate what's working and what needs to shift strategically. A good chance to review systems (how we do what we do) and tools (what we need to do it better), and even the team (who we need to do it better). This is also a good chance for board reflection and board meetings (I suggest using the 5Ds) to gather input. Additionally, it is a good opportunity to review the company using the CVFB method to ensure everyone is aligned.
- Annually: Lays out the vision, budgets, KPIs, and key company-wide priorities for the year ahead.
Great CEOs don’t just set the cadence; they also own the content. They communicate clearly, with purpose, and in a way that energizes and aligns people across the organization.