This article from Selling Power offers suggestions for salespeople when questioning prospects.  The author makes some excellent points with one that stands out – number 9.  I have edited the content for length.

1. Qualify prospects
You can quickly establish if this “suspect” is a qualified prospect with a few questions. Many salespeople waste valuable sales time chasing the wrong company or talking to someone without decision-making power. Develop a profile of your ideal prospect. What criteria must a “suspect” meet to qualify as a bona fide prospect for your product or service?
2. Uncover needs
By asking questions and understanding the client’s needs you can determine which benefits the prospect will buy.
3. Help Your Prospect Clarify Needs
Some clients don’t really understand their own needs or may not have clearly defined their goals. They may not understand the many considerations in choosing products or services such as yours.
4. To Gain Respect
Sophisticated prospects will want to know that you know what you’re talking about. Knowing your market and your product or service and doing your homework about this prospect are important. 5. To Build Long Term Relationships
Many salespeople perform fine on the first call but what do you do for an encore? By continuing to ask intelligent questions you will deepen your understanding of your client and his company, along with your own industry.
6. Involve the Client
Asking clients a question involves them in the sales process. It also helps to limit your own talking. You know that a good salesperson does not deliver a monologue.
7. Learn How to Sell This Prospect
An involved client may tell you what you need to do to sell him. You want the client to have a chance to vent his feelings and ideas. You will learn how cooperative this prospect will be.
8. Establish Trust
Establishing rapport and a climate of trust and confidence can be better achieved through questioning rather than small talk and chit-chat. Asking questions shows clients that you are interested in them, their businesses and their needs. You are not there to give them a standard pitch to fulfill your sales quota.
9. Maintain Control
Asking questions allows you to control the sales interview without the prospect feeling he is being controlled. You are leading rather than pushing. By maintaining a friendly and open attitude and asking good questions, the prospect experiences you as an interested and well-informed expert. To the casual observer of such a conversation, it would appear that the prospect is leading the conversation. In reality, the salesperson is subtly leading. Imagine watching an inexperienced rider on a horse. In an often vain attempt to direct the horse, the rider pulls every which way on the reins and kicks the horse. The horse may rebel or resist these directions. In contrast, the expert horseman would appear as if he is not doing anything to direct the horse – he is simply sitting on the saddle. Yet, it is through subtle movements of the fingers and shifts in the pressure of his legs against the horse that the rider controls the horse’s movements. In sales, we might refer to this subtle control as a “soft halter.”
10. Get Minor Yesses
By asking some questions that you know the prospect will answer yes to, you can create a positive atmosphere filled with agreement rather than conflict.
11. Avoid Rejection
Asking questions lets you evaluate how much interest a prospect has and if she or her company is in a position to buy at this time. Through better probing, your expectations will be more realistic.
12. To Close the Sale
Ask questions to lead toward the close and to determine if the prospect is ready to take action. By asking questions you may find prospects ready to buy much earlier than you thought. Once you think they are ready to buy, ask a closing question and close the sale!

It is counterintuitive to think that the person listening is actually controlling the conversation, but it is true if they are the one asking the questions.  The horse-riding analogy describes it well.  Questions, followed by attentive listening, is one of the tenets of successful selling.

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A good article here from Selling Power titled Five Questions Every Sales Manager Should Be Able to Answer.  The questions are spot on, but pay special attention to number 3 (my editing):

1. Which lead sources result in the highest percentage of closed deals? Do you know where your best leads come from and what those leads look like? When you do, you can better direct your marketing efforts and dollars while boosting your conversion rate.
2. Are your reps selling the most profitable products? Often, reps will sell the products that are easiest to sell rather than the ones that provide the highest margin for the company. Face it: they’re going to get to quota the easiest way they can and if it means selling lower margin products, they’re going to do it.
3. What percentage of the time is your sales process being followed? This is an important question. Assuming, of course, that you have a process in the first place, do you know how often reps are adhering to it? Many sales executives have lamented that there are sometimes as many processes as there are reps. If your sales results are in need of a course correction, dig into this question. It may turn out that fixing those results is as simple as getting everyone to adhere to your established process.
4. Where do your reps tend to stall in the sales process? In other words, do you know exactly how deals move through the pipeline for all your reps and where in that pipeline reps tend to get hung up?
5. Which competitors do you lose the most business to, and why? All managers knows who their biggest competitors are, but do you know precisely how much business you lose to each one? And more importantly, do you know why?

I am always amazed at how many sales managers lead without a selling system.  Now, I’m not talking scripts, but a selling system with enough flexibility for each rep to adapt it to their natural strengths and styles.

We walk into many sales departments where each salesperson has their own approach to selling.  The reason this spells trouble is that you never have an accurate forecast, the sales manager has difficulty coaching the salespeople and new hires are often sent into the market without the right tools to succeed.

Much of this approach comes from sales managers who are unsure themselves about which selling system to use.  If they are using some form of a selling system, the next issue is holding the salespeople accountable to the system.  The best sales teams we see are the ones that use a system and the sales manager holds them accountable to it.

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