When I was in day-to-day outside sales, I always hated going out on sales calls with my manager. I also didn't like taking the new guy out on sales calls with me. And, when I was the new guy, I always felt awkward tagging along with the experienced pro.
And I think that awkward feeling was the same on the other side of the table. I think most prospects (the non-sales oddly refers to them as "owners", "managers", "the boss" and other non-sales-designated titles) don't like being out-numbered.
Their defenses go up a notch. I know mine do if I am unexpectedly dealing with two sales reps instead of the one that I know or am expecting.
Be sensitive to how your customer is going to perceive a sales call with more than one sales person present. If you think it has any chance of hindering your efforts and hard work up to this point, go it alone.
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