The classic story of nice guys who can’t sell against cutthroat competitors is a perfect illustration of the fundamental dilemma most founders eventually face:
Does the company serve the needs of the founders? Or do the founders serve the needs of the company?
If you’re lucky to be in business long enough, you’re going to discover that many times, what the business needs and what you’re comfortable doing will often diverge.
At that point, you may have to choose between your own comfort and the company’s success.
The tough part is that there’s no guarantee that sacrificing your own comfort will work. And that’s especially true if you do something like hire a new VP Sales without learning for yourself how the sales process actually works.
After years in the business, I’ve learned what I can and can’t do. I’ve teamed up with a VP Sales who knows how to sell. And I know when to ask questions, and when to get out of the way and let him go for the kill his way.
(This post originated as a comment on Steve Blank’s blog)