Three Emails Beat Fifty-Two

At the offsite dinner, three senior people admitted it: sometime in the first year, they had stopped reading the CEO's Monday email. The CEO had sent 52 a year for three years, the same shape every time. A paragraph on last week, a paragraph on the week ahead, a paragraph on values. Opens stayed high, because nobody ignores mail from the boss. Reading had stopped. What the CEO wrote the following December is the reason they started again, and it cost the CEO more than any Monday email ever had.

The weekly cadence fails for a plain reason. A CEO who writes every week has to find something to say every week, and most weeks the real content is thin. The team learns that CEO email averages to filler and sets its attention there. Then the one email that carries weight lands in the same skim. Moving the update to a Slack channel changes nothing; the habit travels with it.

The next year the CEO sent three. March, after a board decision that changed the team's comp structure: what was decided, why, which parts were hard to hear, and follow-up dates. August, after a senior departure that rippled through the company: what the exit conversations taught, and what was changing. December, after a quarter that missed plan. That one did the work.

The December email named the strategic call behind the miss and said it was the CEO's. In a company of 30, a sentence like that reads something like: "We missed the quarter. In June I hired two people ahead of contracts I expected to sign. The contracts slipped. That was my call, not the sales team's. Nobody's role changes because of it, and by January 15 I'll show you the revised plan."

That sentence is expensive for the person who signs it. A 30-person company has no layer between the CEO and the readers. The person who made the bad hire-ahead call is the one writing, and every reader knows it. Admitting it in writing costs the CEO standing with the team and, in the next board meeting, with the board.

The vague version, "a tough quarter, lessons learned, onward," keeps that standing and moves the cost onto someone else. Say the operations lead earns $110,000 and reads the vague email as a hint that cuts are coming. She returns the recruiter's call. Say she leaves and the seat sits empty for three months: that's about $27,500 of salary-worth of work that either lands on the CEO or doesn't get done, before the search fee and the training of whoever comes next. That bill is larger than a bruised ego, and a different person pays it. The people with the best options act on a guess first.

So the email that gets read has a fixed shape. What happened, concretely. Which decision was the CEO's, including the wrong ones. What the CEO still isn't sure about. What it means for the reader's job and pay, which is the question everyone opens it to answer. Specific actions with specific dates. No motivation. It's the same reason the board update that worked was three paragraphs.

Timing follows the event, not the calendar. The Monday email goes out Monday whether or not Monday has anything in it. The real one goes out when the thing has happened, which might be a Thursday at 4pm. Draft it in a Google Doc and sleep on it first; the email you wrote at 11pm is rarely the one to send.

Before the next planned company email, ask:

• Did something happen that needs my voice, or does the calendar say it's time?
• Does it name my own call, if the call was mine?
• Does it answer what this means for each reader's job and pay?
• If I sent only three emails this year, would this be one of them?