Are You a Kanye? Do’s and Don’ts Selling Software.

What a bozo…interrupts sweet Taylor Swift’s award and proceeds to make a fool of himself in front of millions.  Ever done something like that?  If you answer no to that question, well then you’re a fibber – and that’s worse than being a bozo.  This, my friends, is a classic case of a lack of situational awareness.  SA is perhaps the #1 attribute of a great software seller.  So, gonna lay out some common scenes in a software seller’s life that will help you not be a Kanye.


  1. Reach for the check within 10 seconds when at an event with a prospect.
  2. Give your coach the credit for your ideas when the prospect’s entire audience is present. Make sure those ideas are socialized with your coach in advance.
  3. Communicate your win-themes early and often.
  4. Always…always remind your prospect why she should buy from YOU vs. your competition. Hint, read my blog entry on the personal win.
  5. Over-communicate internally. This includes but not limited to your next steps, win themes, everyone’s roles clearly defined, and your open holes still seeking to fill.
  6. Tailor your pitch to your customer’s business. Yep, had to say that….
  7. Be a good manager of your customer’s time. This means always finish your meeting under the allocated time.
  8. Always engage tons of people in your deal…that way if there’s a murder, there are more finger-prints on the knife.
  9. Engage people from your company based on their personalities, not their skills.
  10. Be authentic. Desperation is the world’s worst cologne.


  1. EVER deliver a generic corporate overview slide. You will lose your audience before you begin.
  2. Deliver donuts…that’s boring. Cater in breakfast tacos from a up and coming food truck.
  3. Discuss politics, religion, or anything other than what the prospect wants to talk about. If they start talking about a taboo subject, ask where the bathrooms are.
  4. Argue with a prospect publicly. Politely tell them there’s a different lens to look through and that you see both sides of the equation.
  5. Make your product the “point.” No product is that good.
  6. Over or under-dress your prospect coach. Wear what he or she wears.  If it’s different than the buyer, too bad.  She’s your gal and let the world know it with how your dress.
  7. Go to prospects where you’re wanted, but spend time at prospects where you’re needed. Sophisticated sellers know the difference.
  8. Let your ego get in the way of your W-2. This usually means shutting your mouth and asking questions when forced to speak.
  9. Be the guy who plays fetch with prospects. You’ll lose almost every time.
  10. Be the person who “checks the box” with the boss.  It’s easy to tell who those are and they never last long term.

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