Success Mindset, Winning Deals

[Video] The Power of a Pessimistic Sales Strategy


Although I’m naturally an optimistic person, I truly believe in the power of pessimism. I don’t care what all those self-help gurus tell you. If you only see the world through your rosy glasses, you’re going to run smack dab into sales-derailing situations that could have been prevented.

That’s why it’s imperative today to take time to be negative when preparing your sales strategy. For every sales opportunity you have, you need to ask questions like:

  • What could go wrong in this meeting?
  • Where are our weakest spots?
  • Who  might not want us to be successful?
  • Why would they decide to stay with the status quo?
  • How could our competitors beat us?

If you can visualize these obstacles happening, you can do something about them – before they create problems for you.

For example, let’s be pessimistic about your prospects deciding they’d rather not change. And why does it usually happen? Because they don’t see enough value in doing it. Are you hurting your chances of success by being so brutally realistic?

No. You’re actually increasing them because now you can create a sales strategy to address that issue. That’s why pessimism is so darn important today. It prepares you to deal with reality much more effectively.

So go ahead – be negative! It makes a difference.

Power of Pessimistic Sales Strategy
After a successful career in the sales world, writing five books, and speaking internationally, Jill is now tackling an even bigger challenge. She's focused on bringing the "millions in the middle" together to solve some of the biggest issues facing our country and the world. Jill truly believes so much more is possible if we can work together.