You’ve been engaging with a promising sales prospect, and suddenly, he’s gone completely silent.

He won’t answer your calls or emails, and even missed a meeting that you had set a few weeks ago. You’re frustrated, annoyed, upset, and — most of all — worried that you may not hit your number because you’ve lost this deal.

Despite all of these emotions, don’t get so desperate that you decide to do the worst possible thing: contact the prospect’s boss.

Going above your prospect’s head won’t solve your problems, and may in fact make things much worse. Instead of closing the deal, this tactic will just end in tears. Here’s why you shouldn’t make the mistake of trying to close deals behind your prospect’s back.

It’s Disrespectful

Nobody enjoys feeling powerless or insignificant at work, however this is exactly how you’re making the prospect feel. While you do want to eventually reach a decision-maker during the sales process, this isn’t the way to go about it. Just imagine for a moment how you would feel if someone was initially talking with you, and then decided to call your boss without telling you first. Wouldn’t you feel disrespected and devalued? Of course you would.

If you go above your prospect’s head without an introduction, he’s guaranteed to be upset and annoyed. The prospect will feel unimportant in the sales decision-making process, and may even feel as though you’re embarrassing him in front of his boss. Any trust you have built up with the prospect is immediately — and often irretrievably — lost when you go behind his back to try and close the deal.

You’ll Lose a Champion

A promising sales prospect is your road into the company and can act as your internal sales champion, pushing for your success. But if you try to get around this prospect, you will lose your champion in an instant. Before you decided to go behind his back, the prospect may have been considering looping in his boss to learn more about the product. But now — why would he want to help you out?

Even if you had a positive call with the prospect’s boss, it’s no guarantee that you’ll close the deal. Instead of advocating for you internally, the prospect is now unhappy with you. If the prospect is no longer on your side, he may even decide to try and sabotage your deal. A former champion could very quickly turn a promising opportunity into a dead end by telling his boss that your product is a complete waste of time.

Learn More About Becoming a Great Sales Rep »

It Won’t Work

Just because you haven’t heard from the prospect in a while doesn’t mean you have nothing to lose. Reaching out to his boss is something of a Hail Mary pass in the last 10 seconds of the game, but what if the game wasn’t really over? What if your prospect simply forgot to tell you that he’s going on vacation, or he is incredibly busy preparing for a big event? You have no idea what’s happening in his life to cause the radio silence.

If you’re impatient and decide to go above the prospect, you can’t recover his respect. Instead of getting desperate and reaching out to your prospect’s boss, take a deep breath. Stay calm, and try to think how you can re-engage him in a more creative way. Even if you can’t revive the prospect and do end up losing the deal, you never know what will happen down the line. Something could change, and that same prospect could re-engage with you in six months once he has the budget or the authority to make the purchase.


Instead of being the rep that went behind his back, he will still consider you a trusted advisor and decide to give you a call back. By keeping a positive relationship with this prospect, you could eventually turn a lost deal into a Closed-Won deal.
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