Sending an email to your CEO can feel like approaching a celebrity — exciting and nerve-racking all at once.
That's because, while you could impress your CEO with your knowledge of the company and passion for your job, you could also turn them off with signs of carelessness or stepping out of line.
To help you figure out how to craft the perfect message, we consulted career experts to get their best advice on how to reach out to executives. Amanda Augustine, career advice expert for Talent Inc., outlined key steps to sending a thoughtful, readable email — and getting the feedback you need.
1. Consult your direct manager first.
Unless the CEO is your direct manager or you're responding to a direct request from him or her, it's wise to let your boss know that there's something you'd like to email the CEO about.
That way, your boss can decide whether it's something that really requires the CEO's attention.
Your manager "probably has better insight into what makes sense and what doesn't make sense," Augustine said. "You want to go through the right chain of command and the right lines of communication."
It doesn't matter if you have the most wonderful idea for the company, Augustine added — you'll want your boss to vet it first. Once you get confirmation that an email to the CEO is appropriate, you can CC your boss or add him or her to the message.
2. Write a short and action-oriented subject line.
You should always write your subject line before you write the body of the message. Otherwise, you might forget to include one.
Augustine advises that you limit your subject line to eight or fewer words, especially since your CEO may be reading the email on a mobile device that cuts off part of the text.
You'll also want to indicate if you need a response by a certain date, so your boss can prioritize the requests he or she is receiving that day. Augustine suggested setting the deadline a day or two before you actually need your CEO's response. That way, if your CEO gets really busy and responds late, you won't be in trouble.
Here's an example of an ideal subject line: "Project XYZ proposal — please reply by EOD."
And unless you have a really good reason, avoid marking your message high importance or high priority. "That's almost as bad as putting everything in caps," Augustine said.
3. Keep your greeting concise.
Barbara Pachter, a business etiquette expert, suggests using a general greeting such as, "Hi, name," instead of "Good morning" or "Good evening." Or if you're sending an email to the CEO and their assistant, "Hi everyone."
4. Use a salutation and sign-off that's appropriate for your company culture.
If you're uncertain how to address your CEO, Augustine suggested asking coworkers on your level how they've addressed him or her when they've sent emails in the past. You could also ask your direct boss for advice.
Another option is to look for email threads between the CEO and other employees and see which salutations they used.
But if you still can't figure out what's appropriate, Augustine said you should always err on the side of formality (e.g. "Dear Mr. Smith").
Your sign-off should be similarly short and simple. "Best, [your name]" generally works well. If you've already established a rapport with your boss, you can also use your initials.
5. Keep the text short and specific.
You definitely don't want to send an email with blocks of text, Augustine said, especially since your CEO could be reading the message on a mobile device.
In order to make the email more easily readable, Augustine recommends using a short opening paragraph and then outlining each topic using bullet points. You may also want to bold or highlight the call to action (e.g. "Please reply by EOD").
Though you don't need to adhere to a specific word count, Augustine said, "use just as many words as you need to get your point across and not a sentence or a letter more than that."
Think of the email as being a summary, or the CliffsNotes version, of the topic you want to discuss.
Ultimately, Augustine said, keep in mind that "if they want more information, they'll be sure to ask for it."
6. Review your message for misspellings and grammar mistakes.
Always re-read your email before you send it, especially since there are words that your computer's spell-checker doesn't automatically pick up.
In many cases, Augustine said, this message will be your CEO's first impression of you and your professional brand. "You don't want to be thought of as the person who can't spell correctly and can't string a sentence together without making a mistake."
7. Avoid jokes.
Because we're so accustomed to communicating via texts and social media, we might be less formal than we should in important emails.
Specifically, Augustine said, "sarcasm can often be lost in [email] translation," so be careful not to include anything that can be misconstrued.
"Don't leave your message up for interpretation," she said.
8. Follow up politely.
Your email should include a call to action, or a deadline when you need a response by. Set a reminder in your calendar to follow up the day after that if your CEO still hasn't gotten back to you.
Here's an example of an appropriate follow-up (you can tweak as necessary): "I'm following up on [whatever issue] and wanted to make sure you saw this item. Please let me know if you need any additional information from me before you can respond."
9. Throughout the process, remember email etiquette.
All professional emails you send should be filtered through certain standards that apply more intensely when you communicate with someone higher up. For example, use exclamation points sparingly in your message to your CEO to avoid appearing overly emotional or immature. When you're drafting your message, consider your audience and the time they have to spend looking at your email. Make sure to tailor your message accordingly.
A useful tip is to add the recipient's email last, after you've gone through your email thoroughly and checked it for errors. You don't want your CEO to receive a half-drafted email you didn't mean to send.
Sherin Shibu contributed to an earlier version of this piece.
by Theo Strauss
The Emailer’s Guide To The Galaxy: Part II
As I explained in my last post, I’m 17, so my network isn’t too big just yet. For me, cold emails are the easiest and most direct way to reach a founder. Over the past year, I’ve sent over one hundred emails to CEO’s, founders, and heads of design, and have gotten a response from over 80% of them.
My emails started out unconventionally — filled with long paragraphs, massive intros, and frankly, very little about the recipient. But, with A/B tests, just the right amount of analytics, and persistence, I was able to notice what stuck.
Most people just assume they’re bad writers, others think it takes a degree in communications. Not me. In this post, I’m going to give you a play by play handbook on what I learned in the past year. And, by the end, you should be able to lock down a meeting with whomever you want.
The email address
Depending on whom you’re emailing, the address you choose to send your email to can decide your fate.
Why? I get into this in the first post of this series - How to find any CEO’s email address in minutes. I touch on deciding which email address to use in the first part of that post. You should probably read that before getting into this one.
Composing the email
In the world of email, the battle starts before your message is even opened.
It’s your subject line against the rest in their inbox. You’re a mere peasant among the hundreds of others vying for the king’s attention. To get in front of the throne, to have the king hear your thoughts, the subject line of your email has to be perfect. There are two ways of going about this:
- The trojan horse
- Knocking on the front door
The trojan horse strategy is another name for camouflaging. Here’s an example:
What do you think?
Remember, with hundreds of emails coming in a day, the CEO you’re emailing skims their email for the ones that need the most attention. This subject line blends perfectly into the myriad of other work emails they’re receiving.
“What do you think?” can apply to a proposal that needs looking over, a meeting that needs confirming, or a random question. Consistently clicking on subject lines similar to this one might get your email opened.
Knocking on the front door is the complete opposite of the trojan horse. These types of subject lines are perfect for a pitch or if you stand out and can take advantage of that. Here’s an example:
$10 million in revenue 1 month in, now I need your help
This is complete clickbait, but it can pay off in big ways. The rest of this post will guide you in keeping their attention now that you’ve grabbed it.
The greeting
“Hi,” “hey,” “hello,” “what’s up,” “yo,” “dear,” “good morning,” “whomever it may concern”. The first two words of your email set the tone for your entire note.
That’s why deciding which greeting to use is crucial. The one I’ve found the most success with is “Hi [first name],” and Business Insider agrees. This is because it’s not too casual (For example, “hey” or “what’s up”) and it’s not too formal such as “dear” or “whomever it may concern.”
It’s ultimately up to the person you’re emailing, though. When they respond, they might use a different greeting than you. From then on, use their greeting while emailing with them. If they respond with the same greeting, you hit a home run.
The first line
You’ve convinced the person you’re emailing into looking at your note and you set the tone with the greeting. Now, it’s time to grab their attention.
Here’s a look at the line I use:
I’m not a normal kid. I’m 17, go to the Dalton School, right uptown from [insert their company here], and I’d love to ask a question.
Let’s break that down. In one sentence, I’ve said:
- Who I am
- Why I’m different
- How we’re distantly related
- What my purpose is with this email
CEO’s don’t have much time, and they have even less for people they don’t know. Captivating them in the first sentence is key.
The bolded words are the most important. Being 17, a kid, sets up who I am and what makes me differenct. Because I’m local to where they are, it gives them an incentive to learn why I’m reaching out to them. And, instead of just saying “Hi, nice to meet you”, I’m declaring that I have an intention.
Let’s look at an example opener:
I’m a junior at Stanford, 95% of the campus is on my app, and I wanted to talk about YC.
The same four keys appear in this sentence. The sender is a Stanford student, they’re different because of the number of users they have, the example recipient is a Stanford alum, and has gone through YCombinator.
The first sentence is setting the stage for the rest of the email and offers a quick preview from the inbox. On that topic, here’s how much preview space there is for different email clients.
Apple Mail: 140 charactersGmail: 110 charactersAOL: 75 characters
Outlook: 55 characters
The example above has 88 characters, and if you include the subject line, it’s 109, just below Gmail’s cap.
Here’s one thing to keep in mind while writing an email: just like it was a fight to get your email clicked on, it’s still a fight to have them read line after line of the body. Captivating your reader with every paragraph is essential.
The key to making the CEO read each line is to draw connections between the two of you. With more in common, the recipient will want to keep reading, just to see what sets you apart. It’s exactly like how getting a job is easier if you went to the same school as the founder of the company.
The bio is the place to do that. While making connections, you’re also touting everything you’ve done that’s impressive and how you’ve gotten to where you are.
The trick to making those connections in each paragraph is research. I recommend you find five links about the founder, CEO, or person you’re reaching out to before even starting your draft:
- 1 interview with them
- 2 articles covering them
- Their website / about page
- Their LinkedIn (past companies, education, volunteer work, and contact info)
On each page, you’re bound to find one piece of information that helps your case. Whether it’s a shared city or school, or even if you have a friend who worked for a company they did, it’s helpful to put that in your bio.
Here’s an example of the bio I used for my last email:
New York has taught me to take a deep interest in the world around me: the energy, the innovation, and the perspectives.
A couple years ago I started to brand companies, one of which Hillary Clinton Instagrammed about, which led me to start designing apps, creating solutions to New Yorkers’ daily problems.
To bring them to life, I taught myself to code, which landed me at WWDC as a scholar.
Meeting founders there, I started to conduct case studies, looking at how design can help solve problems the future poses, looking at how ride-hailing can be made more accessible.
After WWDC, during the summer, I Citi Biked across the Brooklyn Bridge every day to intern at a startup in DUMBO.
And last fall, I trained to run a marathon, running every day in Central Park. In November, I crossed the finish line in Cape Cod.
You’re probably thinking, “that’s one long bio.” In reality, the more in common you two have there, the more they’re willing to read.
Let’s break this bio down. The person I emailed 1) lives in New York and was on the former mayor’s communications & marketing team, 2) worked on Hillary’s campaign, 3) had tagged WWDC on her Instagram, 4) is at Citi Bike right now working on alternative transit, and 5) is a runner.
Five things in common from five websites, all in chronological order. This makes the email flow, progressing from the past to the present.
The flattery and the ask
After making the connection between the founder and yourself, now is the point to make the connection between you and the company they founded/run.
Showing why you love their company so much is the perfect stage to deliver your ask. This section is short, but it is impactful. Before getting into why this is so successful, let’s look at an example:
Your work and mindset, frankly, inspire me. As a co-founder of a startup and an aspiring designer, I look up to you, your past work, and [company name].
Your platform has changed the way people communicate, but in a way none has before: it’s done so with design.
Now, I want to help [company name] inspire more people by joining your interaction team. With my background being intertwined with the word design, itself, I’m positive that I can truly help make a difference. I know both sides of the coin, the engineering, and the design side, and I hope to bring that with me.
In three short paragraphs, I explain why I think the CEO is so special, why I think their company is so special, and why I’m emailing in the first place.
This works because, in the first paragraph, the flattery makes the recipient excited. In the second, the CEO sees a true understanding of their company. And by the third, the quick acceleration has brought the reader to the ask in a good mood, allowing them to absorb why it was worth getting to the point of this email and what separates the writer from the average.
As you might’ve noticed in this email, and this Medium post, paragraphs are kept to two or three sentences max.
The shorter paragraphs make the email feel shorter as a whole. Instead of endless scrolling, the reader feels as if they are making progress after each paragraph ends.
Longer paragraphs also lead to skimming, and somewhere in the middle sentences, the reader loses focus.
Finally, as most CEO’s read their email on a mobile device, long paragraphs look long, and short paragraphs look normal.
The conclusion
Just how the email accelerated to its apex quickly, it needs to decelerate quickly as well. Once the reader knows the point of your email, they don’t care much about the rest. So in the conclusion, you need to wrap up and get out.
I’d be thrilled to hear your thoughts and would love to continue this conversation. My resume is attached and reference letters are included in it. My portfolio is just my website, so that’s linked as well. Let me know what you think.
This sums up everything you need, you can even copy and paste. The reason this works is that it continues the positive attitude and excitement while offering further reading, like a resume or portfolio.
The signature
Similar to when talking about the first line, many options are available to sign off with.
“All the best,” “best,” “thanks a ton,” “thanks,” “cheers,” “sincerely,” and a simple dash are some examples.
Full disclosure, I use “cheers,” but Business Insider recommends “thanks.” Look at their do’s and don’ts for this one.
Just like five links were recommended in research, five links are recommended for the signature. After testing as few as one link to as many as six, I’ve found it’s a in perfect balance. You should add your:
- Website/portfolio/Github
- Resume
- Phone number
Formatting tip: put a space between the first three and the last two, in order to separate your personal links from contact info.
The send button (don’t press it yet!)
One last thing: before pressing the send button, you need to prepare the war room.
If you send an email without a tracker or the right analytics, your odds of getting a response go down significantly. So, in my next post, I’ll cover how to ensure a response by seeing when they read your email, what they click, and how that can inform what your follow up should look like.
If you liked this post, hold down that ? icon (you can go up to 50, you know). Stay tuned for the next post and the one after that, which will go into tracking the progress of your email.
Follow my Medium to learn more about design from a new perspective, literally. For the next few months, I’m diving into how design will intersect with the future. On this page, you’ll see case studies looking into self-driving cars and posts highlighting interfaces that are breaking boundaries in the world of UI/UX.
You can also catch me on Instagram and Twitter!
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