How to contact a CEO of a company

When it comes to emailing your CEO or emailing the business owner, it makes no difference whether you work at a large or small agency. It can be a little intimidating.

Your CEO has a lot on his/her plate and when you send an email, you want it to get read, you’d like for your communication to somehow stand out, and best of all, you’d love to receive a response. Actually, the best response is if you received immediate praise and adulation in recognition of your email writing skills, but let’s be honest…thats probably not going to happen.

If you’re worried about sending an email to your CEO or to any important busy figure, you’ve come to the right place. This article will present 5 easy steps on writing an effective email to the busiest amongst us.

1. Write a short, yet descriptive subject line

If you’re in marketing or if you’ve ever spent any amount of time evaluating marketing emails as a consumer, then you’re probably familiar with the importance of crafting the perfect subject line for a client’s subscriber list. 35% of email recipients open email based on the subject line alone. Its ironic that many marketers for large businesses skip the process of subject line ideation when its one of the core principles to email marketing or blogging in general.

It’s should be no different for CEOs. If you want to catch their attention amid a mass of communications and during a busy day, your subject line is the place to do it. 

• Get straight to the point
• Your subject line should act like a mini-email containing the most important info
• Does your email contain a report with vital metrics? Say so. Are you writing with a specific proposal? Mention it in the subject line.
• The more concrete, short, and to the point you can be with the subject line, the higher your chances of the CEO opening your email are.

As a general rule of thumb, avoid using spammy buzzwords and/or marking your message as high priority. Every email a CEO looks at is probably in the high priority category. The biggest thing to remember is that an email is equivalent to you popping your head into someone’s office without any concern for what they might be doing and demanding 2 minutes of their time to listen to you.

Do everything you can to minimize the amount of time it takes to understand what you need while maximizing the amount of information communicated.

2. Keep it short

Besides the fact that your CEO doesn’t have a lot of extra time for an email that reads more like a novel, it’s important to remember most CEOs read emails on the go. In other words, they read emails on mobile devices. In fact, 35% of business professionals check email on a mobile device.

Aim to get your point across in as few words as possible. If you’re having a hard time gauging how long your email is, write it out on your own mobile device. That way, you can conceptualize exactly how long your email is and how it will look on your CEOs mobile device.

Bear in mind, when emails are short, it’s easier for CEOs to read and understand, which increases your chances that you’ll get a response.

3. Check for grammar spelling mistakes

This particular suggestion has some irony to it. If you’ve ever interacted with many CEOs and business owners, you’ll probably notice that the majority of their email communications (internally) have spelling mistakes. I’ve personally seen CEOs voice dictate emails or type with blazing fast speed to produce messages that revert to middle-English.

Just like doctors that sign prescriptions sloppily, its a signifier of their business. If you are communicating with a business owner or CEO, you are not to copy this habit. Clear. Concise. Well-spoken.

The unfortunate thing about email is once you’ve pressed “send,” it’s rare you can actually recall the message (due to my own recent unfortunate experience with this I found a way to undo Gmail messages within 30 seconds of sending).  That means you need to have your email proofread and polished before even thinking about pressing send.

Of course, you will want to re-read your email a few times and check it yourself. If you’re not a grammar buff, it’s okay. There are several tools on the market to help you clean up your writing. Run your email through spell check and/or use a tool like Grammarly.

When in doubt, or for good measure, ask one of your colleagues to give your email a quick read-through before pressing send.

4. Provide context for your question

If you are emailing the business owner or CEO because you have some sort of issue that needs to be resolved, then provide context to the issue. Tim Ferriss is both a CEO and serial entrepreneur. He’s given his own take on emailing busy people, which goes into this particular step in more detail.

The goal of providing context is to:

• State your problem clearly
• Mention what you’ve done to solve the problem (or attempt to solve the problem)
• Provide your recommendations for fixing the problem based on your own understanding

If you follow these three simple steps, you’ve basically enabled the CEO to just say “yes, do __, and add this.” No need for a back and forth. Honestly, this principle should be followed in all email correspondence, but CEOs should especially be receiving this style of email.

5. Include important reporting details

There are some emails that your CEO requires you to send them each week. For example, it’s common for marketing and digital advertising agencies to send a weekly executive report to the CEO.

The best news is with the right analytics and reporting tool (like TapClicks), you can set up an automated email. With direction from your CEO, you’ll learn exactly what type of information you need to include in the report. This can include a specific set of metrics, important milestones, and/or drawbacks you experienced during the week.

A tool like TapClicks will allow you to preset reporting parameters. This ensures you are pulling and sending the right data to your CEO each week.

Some CEOs will ask for a report if metrics fall below/above a certain level. With TapClicks, you can set up automatic alert notifications if this happens.

Sometimes the best way to impress your CEO in your emails is to automate them with the information they ask from you each week.

Conclusion

Remember, 86% of professionals prefer to use email when communicating for business purposes. It’s not out of line to send your CEO an email. Just remember when you follow the best practices listed above, you have a higher chance of eliciting a response.

Did we miss anything? Is there anything you would include in the list that helps you write effective emails to your leadership team? We would love to hear from you in the comments.

Written by Jeff Hoffman | @mjhoffman

Imagine you’re a pilot landing a plane. A long runway is obviously better than a short one since it gives you more wiggle room to adjust your approach. When you are tasked with landing on a short strip of runway, you must be far more meticulous about your movements to bring the plane down safely. 

I often use this metaphor to describe the difference between reaching out to a manager- or junior-level buyer as opposed to a C-level executive. When a salesperson sends a message to a lower-level prospect, they can afford to try a stronger ask at first, and then tweak it or scale back as necessary. But when you’re pitching to a CEO, you really only have one shot to engage them. Bungle the ask and you miss the runway entirely.

With this in mind, salespeople must be deliberate and thoughtful in how they approach CEOs if they hope to receive any kind of response. Here are five tips that can help your pitch land smoothly with the chief executive officer, and maximize your chances of getting a reply. 

How to Get a CEO's Attention

1) Use a gentle ask.

CEOs are extremely busy, so in my outreach, I’m not going request a meeting or a conference call. Deploying an overly strong ask in the initial email or call will pretty much guarantee never getting a call back. And at this stage, a response is all I’m after -- not a signed contract.

CEOs aren’t usually willing or able to give of their limited time. So instead of trying to think of the magical sentence or statistic that will prompt the executive to drop everything and meet with you, I encourage salespeople to consider what CEOs are willing and able to give. In general, CEOs are friendly and outgoing since they’re constantly representing their companies to a variety of audiences. They’re extremely savvy when it comes to social dynamics and credibility.

Take this information and play in their wheelhouse. Rather than a meeting or call request, soften and socialize your close by asking the CEO for a referral or a connection to more information. Not only do these asks require significantly less time and attention, CEOs actually like giving references and information.

For example, an email using this approach might read something like this: “I want to make sure I don’t sound foolish when I call your organization about X issue. Where/from whom can I get the best information on this topic?”

Instead of coming to the CEO as a credible sales rep, you’re now approaching them as a curious student, and you’ll likely find that they’re much more willing to engage on this level. And once they start to engage, you can ramp up the relationship bit by bit.

Another benefit of making it ridiculously easy for the CEO to respond to your message: Getting any sort of response automatically boosts your credibility with others in the organization. Maybe you're trying to book a meeting with the VP of HR. You think it's more likely they'll agree to your call when you say "Well, I got in touch with your CEO last week, and she said X ... "? Instant credibility earned.

2) Write emails on your phone.

CEOs are constantly on the go, which means nine times out of 10, they’re reading email on a tablet or smartphone. If an email from an unknown recipient requires them to scroll, it’s not getting read.

Bearing this in mind, write any email intended for a CEO on a smartphone. That way, you see exactly how it will appear to them when they read it. Salespeople often make emails to C-level buyers overly long and complex, because they think they need to sound smart and impressive. But when it comes to getting a response, short and simple is always better.

Don’t sit in front of your desktop computer and fill up the screen with a novel. Get out your phone, type out a few brief sentences, and send.

3) Don’t dismiss the EA.

The common perception among salespeople about executive assistants is that they handle C-level professionals’ calendars and block others’ access to them. End of job description.

Maybe that was the case 20 or 30 years ago. But in 2016, executive assistants are extraordinarily competent in a plethora of areas, and their duties extend far beyond administrative tasks. Beyond keeping their boss’ calendars, EAs also represent their managers at internal and external meetings and sometimes even make decisions on their behalf.

Because of this, I think of the executive assistant as the CEO by proxy. Instead of trying to bypass the EA, work with them to get the information you need and indirectly engage the CEO. Sometimes interacting with and posing your ask to the EA is more beneficial then accessing the CEO. For example, if I was building an ROI calculator to strengthen a presentation and needed data from the CEO to complete it, getting it from the EA is just as good -- and much faster. When it comes to any other ask besides signing the contract, I don’t distinguish between the CEO and their EA due to how closely they work together. 

It's also a good idea to call the EA and pick their brain before you reach out to the CEO -- after all, they know more than anyone else what works with their boss and what doesn't. However, EAs are busy people too, and they won't just give you the information you want simply because you asked for it.

Keeping in mind that EAs get countless calls from salespeople pitching "value and benefits" for the CEO, differentiate yourself from other reps by showing your vulnerability. For example, here's how you might kick off your call with the EA:

"Hi, Mike. I'm going to be reaching out to Wendy soon, and I don't want to look stupid ... what's the one thing I definitely shouldn't say?"

Ah -- now you've got their attention. The EA can be critical in your campaign to reach the CEO, so don’t shoot yourself in the foot by dismissing them.

4) Draw on the college connection.

Salespeople often try to find common contacts, interests, or employers when reaching out to prospects. This is a smart technique, but it can be tailored even further with CEOs.

The most powerful connection you can use with the chief executive isn’t their current company, their former company, or any of their colleagues past or present. It’s their college. In general, CEOs are extremely involved with their alma maters, and if you went to their school or know someone who did, use that as an in. Reminiscing about college days can quickly become talking about current business.

5) Call late.

Common sales wisdom holds that salespeople should call executives early in the day, before they get too busy. But in my experience, connect rate (which I define as a phone call over 60 seconds long) is notoriously low in the morning hours. Why? When a CEO gets to their office, they might not have gotten in the swing of things quite yet, but they're distracted -- thinking about all the tasks they have to get done that day. Not the ideal time to hear from a salesperson.

The end of the day tends to be a better time to call the C-suite -- think 5 to 8 p.m. local time. Later in the day, you'll find that the person on the other end of the line is less distracted, a little tired, and in an overall better mood.

You might be concerned that a late call will be a bother to an executive. But to me, this is a non-issue. If your call comes at a bad time, they simply won't pick up. Not to mention that what a CEO finds "bothersome" has little to do with your timing and everything to do with your message. If you have a good message, they'll be interested in what you have to say -- even if it's a bit late.

Want more sales tips? Come to one of our Public Workshops in Boston and San Francisco in October!

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Imagine you’re a pilot landing a plane. A long runway is obviously better than a short one since it gives you more wiggle room to adjust your approach. When you are tasked with landing on a short strip of runway, you must be far more meticulous about your movements to bring the plane down safely. 

I often use this metaphor to describe the difference between reaching out to a manager- or junior-level buyer as opposed to a C-level executive. When a salesperson sends a message to a lower-level prospect, they can afford to try a stronger ask at first, and then tweak it or scale back as necessary. But when you’re pitching to a CEO, you really only have one shot to engage them. Bungle the ask and you miss the runway entirely.

With this in mind, salespeople must be deliberate and thoughtful in how they approach CEOs if they hope to receive any kind of response. Here are five tips that can help your pitch land smoothly with the chief executive officer, and maximize your chances of getting a reply. 

How to Get a CEO's Attention

1) Use a gentle ask.

CEOs are extremely busy, so in my outreach, I’m not going request a meeting or a conference call. Deploying an overly strong ask in the initial email or call will pretty much guarantee never getting a call back. And at this stage, a response is all I’m after -- not a signed contract.

CEOs aren’t usually willing or able to give of their limited time. So instead of trying to think of the magical sentence or statistic that will prompt the executive to drop everything and meet with you, I encourage salespeople to consider what CEOs are willing and able to give. In general, CEOs are friendly and outgoing since they’re constantly representing their companies to a variety of audiences. They’re extremely savvy when it comes to social dynamics and credibility.

Take this information and play in their wheelhouse. Rather than a meeting or call request, soften and socialize your close by asking the CEO for a referral or a connection to more information. Not only do these asks require significantly less time and attention, CEOs actually like giving references and information.

For example, an email using this approach might read something like this: “I want to make sure I don’t sound foolish when I call your organization about X issue. Where/from whom can I get the best information on this topic?”

Instead of coming to the CEO as a credible sales rep, you’re now approaching them as a curious student, and you’ll likely find that they’re much more willing to engage on this level. And once they start to engage, you can ramp up the relationship bit by bit.

Another benefit of making it ridiculously easy for the CEO to respond to your message: Getting any sort of response automatically boosts your credibility with others in the organization. Maybe you're trying to book a meeting with the VP of HR. You think it's more likely they'll agree to your call when you say "Well, I got in touch with your CEO last week, and she said X ... "? Instant credibility earned.

2) Write emails on your phone.

CEOs are constantly on the go, which means nine times out of 10, they’re reading email on a tablet or smartphone. If an email from an unknown recipient requires them to scroll, it’s not getting read.

Bearing this in mind, write any email intended for a CEO on a smartphone. That way, you see exactly how it will appear to them when they read it. Salespeople often make emails to C-level buyers overly long and complex, because they think they need to sound smart and impressive. But when it comes to getting a response, short and simple is always better.

Don’t sit in front of your desktop computer and fill up the screen with a novel. Get out your phone, type out a few brief sentences, and send.

3) Don’t dismiss the EA.

The common perception among salespeople about executive assistants is that they handle C-level professionals’ calendars and block others’ access to them. End of job description.

Maybe that was the case 20 or 30 years ago. But in 2016, executive assistants are extraordinarily competent in a plethora of areas, and their duties extend far beyond administrative tasks. Beyond keeping their boss’ calendars, EAs also represent their managers at internal and external meetings and sometimes even make decisions on their behalf.

Because of this, I think of the executive assistant as the CEO by proxy. Instead of trying to bypass the EA, work with them to get the information you need and indirectly engage the CEO. Sometimes interacting with and posing your ask to the EA is more beneficial then accessing the CEO. For example, if I was building an ROI calculator to strengthen a presentation and needed data from the CEO to complete it, getting it from the EA is just as good -- and much faster. When it comes to any other ask besides signing the contract, I don’t distinguish between the CEO and their EA due to how closely they work together. 

It's also a good idea to call the EA and pick their brain before you reach out to the CEO -- after all, they know more than anyone else what works with their boss and what doesn't. However, EAs are busy people too, and they won't just give you the information you want simply because you asked for it.

Keeping in mind that EAs get countless calls from salespeople pitching "value and benefits" for the CEO, differentiate yourself from other reps by showing your vulnerability. For example, here's how you might kick off your call with the EA:

"Hi, Mike. I'm going to be reaching out to Wendy soon, and I don't want to look stupid ... what's the one thing I definitely shouldn't say?"

Ah -- now you've got their attention. The EA can be critical in your campaign to reach the CEO, so don’t shoot yourself in the foot by dismissing them.

4) Draw on the college connection.

Salespeople often try to find common contacts, interests, or employers when reaching out to prospects. This is a smart technique, but it can be tailored even further with CEOs.

The most powerful connection you can use with the chief executive isn’t their current company, their former company, or any of their colleagues past or present. It’s their college. In general, CEOs are extremely involved with their alma maters, and if you went to their school or know someone who did, use that as an in. Reminiscing about college days can quickly become talking about current business.

5) Call late.

Common sales wisdom holds that salespeople should call executives early in the day, before they get too busy. But in my experience, connect rate (which I define as a phone call over 60 seconds long) is notoriously low in the morning hours. Why? When a CEO gets to their office, they might not have gotten in the swing of things quite yet, but they're distracted -- thinking about all the tasks they have to get done that day. Not the ideal time to hear from a salesperson.

The end of the day tends to be a better time to call the C-suite -- think 5 to 8 p.m. local time. Later in the day, you'll find that the person on the other end of the line is less distracted, a little tired, and in an overall better mood.

You might be concerned that a late call will be a bother to an executive. But to me, this is a non-issue. If your call comes at a bad time, they simply won't pick up. Not to mention that what a CEO finds "bothersome" has little to do with your timing and everything to do with your message. If you have a good message, they'll be interested in what you have to say -- even if it's a bit late.

Want more sales tips? Subscribe to my quarterly newsletter "The Deal Doctor™" to receive my latest tips, techniques, and strategies to achieve greater sales.