The CEO's Email Reality Check
Week 4 of the Email Mastery Mini-Series
Read Time: 3 minutes
TLDR: Email success requires CEO-level commitment to frequency and resources. Half-hearted email programs don't move the needle. All-in programs build relationships and revenue.
Hi Timeless Leaders,
Over the past three weeks, we've covered the 8 email types, why email is your business backbone, and how to prioritize with the 2x2 framework.
But here's what determines whether any of this actually works:
The CEO's level of commitment to email.
The $10,000 Lesson
Ian Stanley, in his book Just F*cking Send It, shares this story:
A few years ago I ran an in-person email workshop for high-level business owners. Each person there was making at least 7 figures per year. About half of them were doing 8 or 9 figures per year. Each company paid $10,000 to be there in person.
Every single one of those companies was sending daily emails. Some of them were sending two a day.
I don't think it's a coincidence that the companies that emailed most often were the ones making the most money (and as a by-product, helping the most people).
Think about it this way... How often do you talk to your best friend? Or your significant other or your spouse? Or your children?
…You hear from the people who matter most more than the people who don't matter. Deep bonds aren't formed through random communication once a week or once a month.
Your email list matters to you, and the hope is you matter to them.
Frequent communication is essential for establishing these “deep bonds.”
The Leader's Real Role
A CEO’s role isn't to write every email (unless it’s a one-person business—then it might be). Instead the CEO’s job is to make the strategic decision: Are we all-in on building strong relationships, or are we treating it as an afterthought?
If your organization is all-in, it means building a robust email program:
Budget for proper tools and talent
Obsession with adding new high quality subscribers
Set sending frequency standards (even daily emails aren't crazy for engaged audiences)
Develop a differentiated perspective—be willing to take a stand
Focus on storytelling and genuinely helping your audience
Segment your list based on interests and behavior
Integrate email with sales, marketing, customer success, and product
Review performance on business outcomes, not just open rates
If building these relationships isn’t a top priority right now:
Accept that you're choosing slower relationship building and lower revenue
Invest whatever you can in email: you’re going to need it, sooner or later
Build consistency and quality in one or two email types
Develop your ability to evaluate what's working
Commit to continuous improvement
The Half-Hearted Problem
Most business leaders treat email like a nice-to-have rather than a must-have. They:
Let their list(s) grow stale
Send boring, infrequent messages
Lack a strategy for platforms and tools
Measure success by vanity metrics (if at all)
Let email run in isolation from other channels
Wonder why their "email marketing" doesn't work
Meanwhile, their competitors are building daily relationships with the same prospects.
Your Reality Check
Ask yourself:
Am I committing my organization to building real relationships at scale?
If yes, email is your essential channel. Allocate the resources to do it right, lean into increasing your frequency, and pack your messages with value, stories, and a unique POV. Connect it to your other systems, keep learning and improving, and watch the numbers go up.
Not committed? Or not sure?
You can still make progress. Pick one email type and focus on a consistent practice of writing and sending. Make sure there’s at least one way that you can grow you list, and one way to measure improvement, and over time you can start to see the potential emerge.
What’s your next move?
Talk soon,
-Joe
The Email Mastery series is a teaser of the upcoming Making Time season—exploring how leaders design time allocation for their teams. The series is an experiment and a teaser of the kind of practical insight we’ll explore when we get more into organizational leadership (including, but not limited to, “Business Growth”). Let me know what you think by leaving a comment or send me a message / email! I’m always happy to hear from you. You can also change your subscription settings for the Business Growth section here.