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Are You Using Speed Dating to Woo the C-Suite? Try Courtship Instead.

Lee Demby
by Lee Demby on Jun 11, 2018 1:59:32 PM

How to build a relationship with executive decision makers (2)


One of the hardest things about enterprise sales is keeping your own sense of urgency in check. Customers don't care that you have a quota or that your executives are pressuring you and your team to close more sales before the quarter ends.

Moving too far, too fast is bad enough in dating—especially if the interest is all on your side. Putting the sales moves on a CIO or other C-Suite decision maker is potentially the kiss of death.

How to build relationships with a CIO (1)

Don't Rush Things

What you need to do is court your potential customer. Don’t rush things. Instead, slowly build your relationship.  Keep in mind that C-Level engagement is an outcome-driven endeavor. Early in your efforts, the CXO has to believe that spending more time with you will result in a business outcome that accomplishes her strategic objectives.

Use Knowledge to Court the C-Suite Effectively

Now what do you need to court them effectively? Knowledge. You want to prove to an executive decision maker that you understand their priorities—both professionally and even personally, if you can. Have you taken the time to research their business strategy and priorities?

Improve Your Engagement With the C-Suite Download the Ebook: Best Practices for C-Suite Selling


What Are Their Professional Priorities?

For example, are they undertaking a comprehensive transformation project across the organization? Or do they have a very specific problem, like security, that they’re trying to tackle? Do you know who their other vendor partners are? What’s their company’s strategic focus for the next year or two? Are they expanding markets, acquiring companies? Are they facing headwinds? Knowing this can help you better understand how your product or service can help them—and let them know you’re in it for a long-term partnership, not just a quick win.

Who Are They as Individuals?

It also helps to know something about who these decision makers are as individuals. Remember, people buy from people. How helpful would it be to know a little about what they like to do in their spare time? Armed with this information, you could invite them to attend a tennis tournament or a wine tasting with your company’s C-Suite leaders.

"To Be Interesting, Be Interested"

Like our friend Jill Rowley says, “to be interesting, be interested.”  Become a pro at asking smart, and sometimes challenging questions. Show you have done your homework and given some thought to what you have learned. Busy decision makers who are hocked all the time by eager vendors are sophisticated; they’ll see right through a sales rookie who asks generic, qualifying questions then jumps right to the product pitch.  In my experience, this is what separates A-level enterprise sales pros from B-performers. Those who have mastered the art of questioning have also typically mastered the art of exposing unconsidered needs to decision makers. Imagine how your target executive will view you after you help them visualize an unconsidered need, challenge, or opportunity.

How long should I wait to meet with a CIO or executive_

C-Level Relationships Need Nurturing

All this takes time, of course.  One you’ve built a solid foundation, that C-Level relationship needs nurturing. And remember, a CXO does not suffer attention from your competitors.  It’s up to you to stay on top of the changing business conditions they are operating in, send them relevant articles they’d be interested in, invite them to be your guest at a conference or a fundraiser for a cause they love…providing value and insight at each turn.

A C-Level decision maker may not need a new friend--but who doesn’t want a trusted advisor whose company they enjoy and who helps them do their job better, makes them look good, and helps solve their problems?

It’s the business version of a perfect love match.

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Lee Demby
Written by Lee Demby
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