I’m going to be honest: most of the advice you read about emailing CEOs is written by people who have never actually had to manage a $50 million budget or a 200-person headcount. They tell you to ‘provide value’ or ‘establish authority,’ which usually just results in a four-paragraph email that looks like a homework assignment. If I open an email and have to scroll to see the signature, I’m archiving it. Immediately. No hesitation. It’s not because I’m a jerk; it’s because I have six back-to-back meetings and my kid just called because they forgot their lunch. Executives are just tired people with too many tabs open.
The time I embarrassed myself in front of Salesforce
It was 2017. I was trying to get a partnership deal off the ground with a VP at Salesforce—let’s call him Mark. I spent three hours drafting this email. I researched his college, his recent LinkedIn posts about ‘synergy’ (ugh), and I wrote this massive, beautifully structured pitch. It had bullet points. It had a ‘case study’ attached as a PDF. I thought I was being professional. I thought I was showing him I’d done the work. What I actually did was give him a chore. I was basically asking him to do an unpaid internship for my company by reviewing all my ‘data.’
He didn’t reply. Not that week, not the next. About a month later, I saw him at a conference in San Francisco. I cornered him near the coffee station (which is a move I now realize is incredibly annoying) and asked if he’d seen my note. He looked me dead in the eye and said, ‘I saw it was long and figured if it was important, you’d follow up with the short version.’ I felt about two inches tall. I was trying so hard to be ‘comprehensive’—wait, I promised myself I wouldn’t use that word—I was trying to be thorough, but I was just being a nuisance. I realized then that high-level people don’t want the full story. They want the headline and the ‘so what.’
I went back to my hotel room and deleted every draft I had in my outbox. It was a total wake-up call. I realized that my ego was the one writing those long emails, not my brain. I wanted to look smart, so I wrote a lot. But looking smart is the opposite of being effective.
The data on why your ‘polite’ intro is killing you
I’m a bit of a nerd when it comes to tracking my own failures. Last year, I ran a little experiment. I sent 68 cold or semi-cold emails to C-suite folks over a four-month period. I tracked everything in a messy Google Sheet. Here is what I found, and I think it’s pretty definitive:
- Emails starting with “I hope this finds you well” had a 4% response rate.
- Emails that got straight to the point in the first 10 words had a 31% response rate.
- Emails sent on Tuesday mornings? Completely ignored.
- The sweet spot for word count was exactly 42 words. Not 40, not 50. Forty-two.
I know people will disagree with me on the Tuesday thing—everyone says Tuesday is the best day for email—but in my experience, Tuesday is when everyone is catching up on the disasters that happened on Monday. You’re just adding to the pile. I’ve actually had the best luck on Sunday nights around 8:00 PM. I know, I know. ‘Work-life balance.’ But the reality is that most CEOs are clearing their inbox on Sunday night to prepare for the week. If you’re at the top of the pile then, you get a reply. It’s a bit predatory, I guess. But it works.
Why I absolutely loathe Grammarly (and why you should too)
Here is my risky take for the day: I think Grammarly is ruining the way we communicate. I refuse to use it. I’ve even told my team to turn it off. It strips the humanity out of your writing. It makes everything sound like it was written by a polite robot that’s afraid of offending anyone. When you’re emailing an executive, they want to feel like they’re talking to a person, not a template. If you have a slightly weird sentence structure or you use a word that isn’t ‘perfect,’ it shows you actually typed the words yourself. It creates a connection. Also, I find that Grammarly always tries to make me more wordy. It wants me to use ‘consequently’ when I just want to say ‘so.’ It’s annoying. I’d rather have a typo and a soul than a perfect email that feels like a brochure.
The part where I tell you exactly what to do
What I mean is—actually, let me put it differently. You need to treat the subject line like a text message. If you wouldn’t text it to a friend, don’t put it in the subject line. ‘Quick question about the Q3 roadmap’ is boring. ‘Roadmap idea’ is better. ‘Your LinkedIn post was wrong’ is the best, though you have to be brave for that one. Anyway, here is the list of things you need to stop doing immediately:
- Stop using Calendly links in the first email. This is my biggest pet peeve. It’s so incredibly presumptuous. You’re basically saying, ‘I’m not going to do the work of finding a time, you go through my calendar and find a slot.’ It’s a power move, and not a good one. If you’re the one asking for the favor, you do the scheduling work.
- Delete the ‘About Us’ section. They don’t care. If they’re interested in your idea, they will Google you. Your signature should have your LinkedIn link. That’s enough.
- Use the ‘One-Screen’ rule. If the recipient has to scroll on their iPhone to read the whole thing, it’s too long. Chop it.
- Ask for a ‘Yes’ or ‘No,’ not a ‘Meeting.’ Instead of ‘Can we hop on a call?’ try ‘Does this sound like something worth exploring?’ It’s much lower friction.
I might be wrong about the Calendly thing for some industries—maybe in tech sales it’s standard—but for a cold reach-out to a C-suite person? It feels like you’re giving them a task. Don’t give them tasks. Give them answers.
A brief tangent about my morning coffee
I’m writing this from a coffee shop in Brooklyn where they charge $8 for a cold brew. It’s ridiculous. But the guy behind the counter just handled a line of 15 people without breaking a sweat because he didn’t waste time on small talk. He just nodded, took the order, and moved on. That’s the energy you need for these emails. Efficiency is a form of respect. If you respect someone’s time, you don’t waste it with ‘I hope you had a great weekend’ or ‘I’ve been a long-time fan of your work.’ They know you’re a fan; you’re emailing them. Just get to the coffee.
But I digress.
The truth is, there is no magic formula. I’ve sent emails that followed all my own rules and still got nothing but crickets. Sometimes the person is just having a bad day. Sometimes they’re in the middle of a merger. Sometimes they just don’t like your face in the profile picture. You can’t control that. But you can control how much of a burden you are. Writing a short, punchy email is a sign of confidence. It says, ‘I know my stuff is good enough that I don’t need to beg for your attention with a 1,000-word essay.’ It’s the closest thing to a silver bullet you’re going to get.
I used to think that the more information I provided, the more likely I was to get a ‘yes.’ I was completely wrong. Information is a barrier. Curiosity is the goal. You want them to ask *you* a question. Once they ask a question, the power dynamic shifts. You’re no longer a solicitor; you’re a resource. And that’s where the real deals happen.
So, go back through your drafts. Delete the first paragraph. Delete the last paragraph. Look at what’s left. Is it enough? It probably is.
I honestly wonder if we’ll even be using email for this in five years. Maybe it’ll all be voice notes or something even more intrusive. I hope not. I like the discipline of a well-crafted, 40-word note. It forces you to actually think about what you want.
Just hit send. Stop overthinking it.