The Startup Toolkit blog, though I’m not personally starting up a new business venture myself right now, is always a wealth of valuable insight on the “entrepreneurial spirit” and how to succeed at building new businesses. Generally, it’s a very good blog worth following for anybody in business.
In a recent post, Rob Fitzpatrick, whose mission with the Startup Toolkit blog is focused on improving fluency in talking about, thinking about, and acting upon young businesses, addresses something that I’m pretty certain affects every sales professional in the beginning of their career, getting over the awkward “please say yes” element of sales. Fitzpatrick admits:
Getting comfortable with sales was truly, deeply painful for me. It was almost certainly the worst year of my life, which I endured only because the alternative was to fire my friends and default on my investors’ trust.
As Fitzpatrick learned in his year of unsuccessful, awkward sales conversations, the outgoing personality and “please say yes” persistence he was sure would serve him well fell painfully short. He found that the real most valuable tools for a new sales person are specific knowledge of the prospect or customer’s industry, and a real understanding of how business-to-business sales really work.
He just needed to gain some expertise, he learned, in his case regarding the advertising industry, which had up to that point been totally foreign to him. Why would knowledge of the customer’s industry matter? So that he could provide some real insight when it came to the all-important sales question, “how can I help?” and ultimately pave the way for sales that would grow that start up into a full-fledged operation.
In fact, he stopped hating sales, he tells us, only when he had talked to enough potential customers that he felt he really understood the market segment he was working in. That’s when he finally felt that he was qualified to sit at the table and offer real help and insight.
All this leads to one important, clear conclusion: though some rejection in sales in inevitable, the best way to avoid awkward, uncomfortable sales situations is always to begin prepared with knowledge about the business the person you’re talking with is in and an understanding of the sales process, coupled with a “how can I help?” mindset.





