You hear it all the time, "Don't be afraid to fail."
As a sales trainer, I don't disagree with that statement. Reps who aren't afraid to fail tend to be more creative, aren't afraid to anchor high during pricing negotiations, and maybe most importantly, are able to recover from a bad month or a lost deal better than others.
However, I think that fear of failure can also be a huge tool for the best reps to use. This doesn't mean "play it safe," it means that you are so scared of losing every deal that you've already figured out every possible reason that you might lose and then come up with a plan of action to combat those potential roadblocks. The majority of the best reps I've come across share this trait while mediocre reps are more overconfident and then miss signs of a deal going south.
Use your pessimism and fear of failure to over-analyze every aspect of your deal. That way, you can plan ahead for objections and complications that you're sure to come across.
When a consistent top performer complains about how they're not going to hit quota that month, you may laugh and tell them to relax because they always hit. Instead, listen to what they're afraid of, listen to their strategies to combat their fear, and utilize that same pessimism the next time you look at your pipeline and forecast. Don't get hung up on the positive aspects of your deals, look at the weak points and address them first. I guess you could say embrace the scary parts.
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