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 six 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.
6) Use a 45-day cadence.
Industry standard is five touches in 30 days. For CEOS, I advise five touches in 45 days.
CEOs' schedules rarely exist on a monthly cadence. They think about quaters, not months. Most prospects are available sometime within a month. No matter when I reach you, there will be sliver of time in four weeks that you're available -- even if for two of those weeks you're on vacation, sick, off-site, working on a major proect, and so on.
But many CEOs will disappear for an entire three weeks at a time, depending on what they're doing.
A CEO can’t stay away from her company for an entire 45 days, which is why I recommend an extended calling schedule.