11 Things I Learned Selling to the C-suite

  1. Don’t be intimidated. The C-suite is people. They watch Netflix. They go to the supermarket. They like to laugh. So do you. So does everyone.
  2. Poke the bear. When you reach out to the C-suite (or anyone), they’re secretly asking themselves, “What do you know that I don’t know?” To get and keep their attention, you need to be the bearer of bad news. What do you know that they don’t know that can hurt them?
  3. Be a matchmaker. I once learned that a CEO’s daughter was looking to start a career as a graphic artist. I introduced her to a few of my contacts. When you put other people’s interests before yours, they want more of you. The opposite is also true.
  4. Let go of assuming. Sure, you have a theory as to how you can help, but it’s a theory. When you’re arrogant, you’re off-putting.
  5. Downshift. The sales cycle is a straight line. You’re paid to get people from point A to point B as fast as possible. However, buyers don’t buy that way. The buying journey is more like a zig-zag line. Be patient. Water the flowers and provide sunlight. You can’t make flowers grow fast because it’s the end of the quarter.
  6. Treat “gatekeepers” like kings/queens. Many execs spend more time with their admins than with their families. Focus on little things. For example, anytime a “gatekeeper” provided me with information, I’d send them a handwritten thank you card. Gratitude forges a solid emotional connection between two people.
  7. You’re the prize. Money is a commodity. Companies can always make more. What you sell isn’t. Approach the C-suite with equal business stature.
  8. Learn how to speak C. Triathletes have their lingo. So does the C-suite. When you talk C, you’re an insider. Read/listen to trade info. Mention something you read and pass the potato back by saying, “How does that compare to your experience?” Example “Josh, many triathletes I work with say they’re spending 20+ hours a week training for an Ironman. I call the divorce by triathlon :-). If you don’t mind me asking, how are you striking the right balance between training, family, and work?”
  9. Compliment. Everyone likes a genuine compliment. Don’toverdo it. “John, as someone with a long and successful career selling, I’m curious, what’s your take on . . . “
  10. Follow up on unanswered emails.
  11. Detach from the outcome. When you’re attached to the outcome, you get too excited. You send five emails In 5 days. When people feel the push, they pull away.