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If we don’t at least attempt to meet with the key executives proactively, but instead wait until an opportunity finds us, we are often stuck selling bottom-up. Once they call us, we lose the chance to be proactive, we end up reacting to opportunities, and it’s possible to lose a great deal of control over how we engage the client. They are in a position to dictate how we sell to them, if we allow it. One of the most common questions that salespeople struggle with is, ‘What do you do when you have made a connection or developed a relationship with a lower-level person, and you know you need to sell higher?’ Well, let’s face it. There are only three things that you can do . . .

Option #1: Just Sell at the Lower Level

One approach is to just do what they tell you to do. Show up, give your presentation, show the product, submit a proposal, and hope like crazy that they call you back. You know what, that’s a depressing way to live. That’s if you can live. You probably won’t sell much . . . Oh, maybe something here and there. But even if you could pay your bills on your base salary alone, that’s not what you signed up for, and your boss won’t be able to justify having you on the team for long.

Can you win some business selling low? Sure. You can play the numbers game. Put out ten proposals, and close one. Put out twenty proposals, and close two. Cut your price 40 percent and you might even be able to close three. But if you were happy with that approach, you wouldn’t be reading this book. Let’s just say that selling low is pretty risky. You could end up wasting a lot of time on deals that aren’t deals. You can’t build relationships with strategic decision makers you never meet. You may also never know what other products and services or other initiatives you are competing with, and therefore you can’t proactively do anything to be more competitive.

Option #2: Go over Their Head and Call Their Boss

Another approach is: When your prospect contacts you, you ask to meet their boss, they say ‘No,’ and you call her anyway. This is an even riskier approach! If you would have called in at a high level a week earlier, they probably wouldn’t even have known about it, let alone cared. But once they call you . . . too late! Now, you have to play by their rules. Or, at least they think you do.

There are circumstances where the ‘go over their head and call their boss’ strategy is the only option left. If you are called into an opportunity very late in the game, or if you simply aren’t given any opportunity to learn about their business, or meet with any of the people who will make the strategic decisions, there’s not much else you can do. You can either play by their rules, as in approach number one, or you can risk it all by calling high anyway.

There are several other techniques, which we will discuss, that should be tried first. I would suggest making this approach your last resort. Only use it if you have exhausted all other options and you are willing to risk damaging any relationship you may have, or may hope to have, with the lower-level person.

If you think the lower-level person won’t find out you called over their head, prepare to be surprised. More than once I thought I was being clever by leaving a voice mail, or sending an e-mail, to someone’s boss on the sly, only to have the boss forward it to the person who originally contacted me. The lower-level person then proceeded to lecture me on ‘how we do things around here.’

Option #3: Earn Your Way Up to the Higher Level

The third approach, which will come as no surprise to you as the one I recommend, is to earn your way past the gatekeeper to get access to higher levels. This is not as complicated as some would make it out to be. It’s relatively simple; it’s just not very easy. Even the most experienced sales professionals find themselves ‘stuck’ from time to time. It is this approach that we will explore here as we look at several techniques and tactics, as well as the psychology involved in making this work for you.