Why You Should Send Friday Updates

The One CEO Habit That Builds Trust Every Week

Friday updates became one of the most valuable habits I ever built as a CEO. I first learned about them from Scott Dorsey, who was a board member at Castiron. He suggested I start this practice. At first, I thought it would be overkill: too much information, not enough new content week to week. But once I tried it, I realized how powerful it was. It became one of the best tools I had to drive clarity, focus, and urgency, the three things I cared about most.

Friday updates also built trust, which was just as important. I cared deeply about being aligned with my team, up and down. If we were all on the same page, we were far more likely to win. By showing up consistently, sharing both the good and the bad, and hitting send every week, I was training my team and investors to expect candor and accountability. No one ever had to wonder what was happening or be surprised by news. That consistency closed the gap between me and my stakeholders. I never wanted an investor to say, “I had no idea” or “That’s the first I’m hearing of this.”

The most effective updates are authentic and in your voice. Don’t copy someone else’s format, make it yours. For me, the structure looked like this:

• Intro note: This is where I stepped into the balcony. I used it to share the big problems I was thinking about, the things that went wrong, or the strategic questions that kept me up at night. I was honest about what mattered most to the business and I wrote it in my own words. My team got these too, so it doubled as an alignment tool.

• Customer story: A win, a loss, or a learning. Our first value was “customers first,” and I wanted to reinforce that every week by starting here.

• KPIs: I kept it tight, usually 4–6 top-level metrics. Sales and pipeline, conversion rates and new logos if we were PLG or self-serve, core product usage, churn, and maybe one or two others depending on our stage. The point wasn’t to overwhelm with data, it was to show the levers we looked at every day and week. If a number was crooked — off weirdly in one way or another, I’d add color. Why did it move? Was it unexpected or on purpose? Anticipate the questions any reasonable person would ask.

• Operational updates: Product launches, upcoming events, or the top priorities for the company. These are the things that we’re working on and those that wehave planned for the next week. Only the things that truly mattered.

• Team wins: I made sure to call out team achievements by name. This turned the update into a recognition tool, not just a status report. It showed investors and the company that we were building a bench of leaders, not just chasing numbers. CEOs build winning teams, and these notes were a way to show how we were doing it.

• Ask for help: This was critical. Every update included a way people could lean in, whether introductions, key hires, or connections to target customers and partners. Your team and investors want to help, give them the chance.

This rhythm didn’t just keep investors in the loop, it made my exec team sharper week to week.

One pro tip: I tracked who was reading them. I used Bitly links (thank you, Bitly) so I could see who clicked through. If I sent the update to 20 people and only 10 clicked, I knew where engagement stood. Yes, I tracked who read them, of course I did. It helped me learn what was working and what wasn’t, and how I could get better.

And always share the bad news, not just the wins. Too many CEOs only send updates when things are going well, and that’s a red flag. The best CEOs communicate consistently, especially when things are hard. Investors tell me all the time, especially in 360s, that their favorite CEOs are the ones who communicate regularly, openly, and ask for more.

One trick that helped me stick with it: I blocked off Fridays from 2pm on. I kept an open draft email all week where I’d throw notes and ideas. By the time Friday rolled around, the update usually took about 20 minutes to pull together. But I always gave myself the time to push back from the day-to-day and look at the business from the balcony. And honestly, no good meetings happen after 2 on a Friday anyway.

This simple weekly ritual delivered outsized returns. It kept everyone aligned, gave me control of the narrative, and reinforced a culture of transparency and accountability. It’s good governance, it’s good hygiene, and it’s good leadership.

If you’re a founder or CEO and you don’t have a consistent update rhythm, start with Fridays. Put it on your calendar. Make it yours. And stick with it.

For inspiration, Visible.vc has a strong library of update templates: https://visible.vc/templates/

Thanks for reading. I write How to CEO as a collection of practical, real-world guides for first-time and early-stage CEOs. If this was useful, please share it with another founder who might benefit. You can subscribe for future posts here: blog.markjosephson.net.

And, if you’d like, I’m happy to read your first draft of your first update. Share with me as a Google Doc at mark <at> markjosephson.net.

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