Jill Konrath

Although I’m naturally an optimistic person, I truly believe in the power of pessimism. I don’t care what all those self-help gurus tell you. If you only see the world through your rosy glasses, you’re going to run smack dab into sales-derailing situations that could have been prevented.

That’s why it’s imperative today to take time to be negative when preparing your sales strategy. For every sales opportunity you have, you need to ask questions like:

The moment Karen walked into my office, I knew something was wrong. "I might as well be selling wastebaskets," she said. "No matter how much I try, customers just don't care about the differences between our system and the others. It's just pure price competition.”

Sound familiar? It’s happening everywhere. And, to make matters even more challenging, today’s customers have done tons of research online and think they know what’s going on.

How can two sellers from the same company calling on the same types of customers sell their services at totally different profit margins?

Here's a story of how two sellers, Kim and Jack, priced their consulting services projects at opposite ends of the spectrum. One had highly profitable sales, the other did not. Their typical project ranged from $60,000 to $80,000.

Nobody wants to make a bad decision. People don't like the unknown; they fear it. They're leery about making any change when there's the possibility of a career-derailing failure.

Your prospect's perceived risk can quickly turn into a sales objection. In order to prevent that from happening, you need to make them feel like they're in good hands.

I'll never forget my meeting with the VP of Sales for a hot telecom company. They'd loved my proposal, so I figured we were getting together to kick off the project.

"I'm afraid I have bad news for you," the VP said. "We think your training program is superior to the other ones we've looked at. Your pricing is fair. And your ability to tie it in with our new product launch is unsurpassed. However, we've decided to go with your competitor."

Should you ask a prospect, "What's in your budget?" You know, a lot of sales training programs tell you that it's very, very important to qualify your prospects. And if they don't have money in their budget, then you need move on because that's a sign of whether or not they are going to actually buy.

Let me give you an example that I think refutes this entirely.

What do you do with people who promise, promise, promise that they'll order for you, but just keep asking for more samples and additional time? That's the question that Helene posed for me the other day. Here's what I told her:

Just because you're a salesperson, doesn't mean you're a doormat. If you feel like you're being used, you probably are. You need to deal straight on with your prospect and say something like this ...

Can you really leverage sales questions to demonstrate your expertise? Absolutely. And, it's one of the best ways I know to show that you're a smart, savvy seller who could bring value to a relationship.

The way you do it is by wrapping the question with your knowledge. For example, I could ask a potential prospect, "What kinds of problems are your salespeople facing today?" It's a nice open-ended question and might get someone talking.