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How to Get a CEO to Answer Your Million-Dollar Question

How to Get a CEO to Answer Your Million-Dollar Question
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Anyone who has tried to launch a new business, knows that it’s not for the faint of heart. That’s why I’ve always tried to put myself out there, as an entrepreneur who’s more than willing to lend a hand to a budding inventor, or take a phone call from someone who is running into obstacles as they try to scale their business.  

So I’m never surprised when I get a random email, from a perfect stranger, asking for my help. But last week, I opened my laptop at 5 a.m.. and found a request I simply couldn’t answer. It’s not that I didn’t want to help. It’s that the email was so long, it looked more like a book, than an introduction.

It was easily 2,000 words. Imagine a four-page, single-spaced letter landing on your desk -- from someone you didn’t know -- before you’ve had your first cup of coffee.

It made me think of a quote I’ve often heard repeated, “I didn't have time to write a short letter, so I wrote a long one instead.”

Related: Master These 4 Simple Pitching Concepts to Capture a Room's Attention

You might be surprised at the number of successful entrepreneurs who are happy to offer advice to someone just starting out. I’ve heard it time and time again from my colleagues -- some very prominent ones even adding, that people rarely ask. So I feel comfortable saying, that as a group, most accomplished CEOs welcome your questions. All we ask, is that you do it respectively.

A successful CEO can receive 300 to 800 emails a day. Typically, the majority are asking for some sort of help -- direction on a project, budgetary allowances, creative input and notes like the one I received last week -- from an entrepreneur struggling to find his or her way.  

It’s much easier just to spill words on a page, than to take the time to think about the reader on the other end. But the reality is, when you’re asking for advice, you have to look at that person as a potential customer and ask yourself these questions:

Why would they want to engage with me?

How can I get their attention in the shortest amount of time?

What’s in it for them?

It’s not that a request for help has to be something that will ultimately benefit the person you’re reaching out to financially. But it does have to touch their soul and break through the clutter of other things on their mind. Being concise and crystal clear will help them help you -- and also increase your chances of receiving a response.  

Related: The Secret to Pitches That Nail It Every Time? Brevity.

Not long ago, I had a conversation with an award-winning journalist who receives hundreds of pitches each day. She knows instinctively when she hears a story she wants to tell, but via email, the message often gets a bit more muddled. She has a standard reply she sends off when she opens an email like the one I received that morning -- asking people to sum up their story in three very short paragraphs, without links to websites or attachments. She does that in the hope that the people who have done their homework and know exactly how she can help them -- will take some time and come back with a targeted pitch. Until then, those emails go to the bottom of her pile.

Are there some jewels that never come to the surface? Sure. But every hour is precious when you’re working on a daily deadline -- whether you’re a journalist or a CEO.

Treat your email like an elevator speech.

Begin with the subject line and assume you have three seconds to get inside that elevator, or in this case, inside your reader’s mind. “Got A Minute?” isn’t a real reason for anyone to reach over and press the open button.  But “Would you mind answering a question about supplier diversity?” would have gotten my attention that morning -- because I knew it was an area where I could offer some help.

Then imagine, as you’re crafting your email, that you’ve made it inside the elevator door. You’ve got from the first floor to the tenth, maybe 60 seconds with a captive audience, to ask your question.

Here’s what would have worked for me:  

“Congratulations on your success working with Lowe’s supplier diversity team. Great to see your product on the shelves! I’m talking with them, but not making much progress. Would you be willing to lend some advice?”

All he would have required were a few additional bullet points telling me what his product was and the obstacles in his way. I would have hit reply and set up a call for that night. Instead, his pain became mine, when he shared every single detail of his slow progress.

Related: 6 Essentials for Making Your Elevator Pitch Unforgettable

Know your story.

So often we go into presentations, all buttoned up with a PowerPoint presentation. And while that might be standard protocol, if you look up from your computer screen long enough to notice -- you may find a few eyes closing in the room. The same thing happens when you attach a long document in an email with a request for help.

Last summer, I was honored to be invited to President Obama’s Global Entrepreneur Summit in Kenya and that “pitch” whether it was in an actual elevator, a virtual one or with a venture capitalist was a subject that a lot of us were interested in.

Shark Tank investor, Daymond John, suggested that you get your story down to five words or less. That’s not simple, but simplicity is exactly what it’s all about. Spend some time summing up how your product or service can solve people’s pain. Pretend you’re pitching an idea for a movie. If you can come up with a great title, chances are your audience will stick around to hear more of your story.

Airbnb’s Brian Chesky mentioned that he looked for more of a mission statement. What would convince your audience to believe in your passion as much as you do? Are you solving a problem 90% of people in the world face? Disrupting a market that hasn’t changed in 100 years? When passion drives your purpose, you’ll find it’s pretty difficult for a wise investor to look away.

Given that advice, if I were approaching either of these highly successful entrepreneurs, this is the way I’d pitch them:

The one sentence story: I’m an inventor and I’ve found a way to eliminate the need for poisons in the home.

My mission: 50 percent of the world struggles with rodent issues. I invented the first botanical repellent to meet federal EPA standards for professional use. It’s guaranteed effective and safe for use around kids and pets. My products keep rodents out -- and in turn, save millions of dollars in damages to homeowners. We’re on the shelves at Lowe’s, ACE and TSC stores nationwide and we’re disrupting the 2 billion dollar retail pest control industry. 

Before you ask for money, ask for advice.

Julie Hanna is the Executive Chair of Kiva, a non-profit lending organization that allows individuals to lend as little as $25 to help create opportunity around the world. She knows the importance of a brand’s story and she also knows what it takes to find funding. If you’re going in for the big ask -- dollars to scale your business -- follow Julie’s lead. Ask for advice over coffee and you’ll get money. Ask for money, and you’ll get advice.

Whatever it is you’re asking for, the most important thing you can do, is honor the other person’s time. Do your homework before you try to connect, to be sure that person has the expertise to guide you, and then know exactly what you need before you reach out. If you want someone to invest their time in you -- you have to invest your own time first.