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Asking Questions That Lead to Success in Selling

I’ve said it many times with clients, at speaking engagements, and in my blogs, but the key to really connecting with a sales prospect or building on current relationships is to always remember: It’s NOT about YOU. Ever.

The simplest way to reinforce that behavior is to come equipped to any meeting at any stage in the selling process (or with any business relationship you are looking to improve) with lots of questions. By their very nature, questions tell a person you are interested in what they have to say, and they put you second. That is immediately engaging, because people love to talk about’s just our nature. But here, you are putting your own interests aside to hear about theirs.

That said, questions need to also tell someone you’re not just barraging them for information, but that, based on what they’re telling you, you’re getting to the heart of their interests, their concerns, their pain points. Smartly done, they build on what you’ve heard already, and tell your client or prospect that you’ve truly been listening to them.

So let’s look at the stages of selling, and see what questions will get you to closing, and build a solid, trusting relationship along the way.


This is the first step in selling that everyone agrees is the most key, and it’s where you gather information to determine if a company or client is a good fit for what you are offering. Their current place in the market, their size, their apparent needs, competition, opportunities — all of it — is information that will help you formulate the questions that tell them you’ve been doing your homework, and leading them to a conclusion that YOU are the person they need to work with.

Everyone is different, so questions should be customized, but should also fall under these basic formulas:

• What is your biggest pain point?

• What do you think this problem is costing you? (time, productivity or money)

• Have you tried to solve this problem in the past?

• What have been the obstacles that have prevented you from solving this problem?

• What would it mean to you personally to get this problem solved? How much better or different would it be for your business

Ideally you may already have these answers already if your research prior to the first meeting was thorough, but notice that none of these questions, or those to follow, will lead to a yes or no answer. That’s the point, because you can’t afford to be cut off at this stage.


As you determine whether or not you have the right person in front of you to get you closer to closing, your questions get more pointed. Still, they show an authentic interest in solving their problem and can lead you to the right connections to make the sale.

• Who is generally involved in the decision making?

• Where does this problem fall in the priorities for your company?

• How soon do you want to get this problem resolved? (Look for answers that are fairly specific. “Soon” is too vague, but “in the next 4-6 weeks is better.)

• What’s the best way to communicate with you and anyone else that is involved in the process?

• What will happen if the decision does not get made?


So you’ve listened to what the customer says they need, but during the presentation phase, you really need to make sure there isn’t something else that needs to be addressed or solved first. Perhaps the real problem isn’t that they need better marketing to sell their product, but that they aren’t responding appropriately to their competition because they lack awareness of who their competition really is.

So in turn, the customer gets to know you better as well, including what your company is about, how well you can work with them based on your interests and goals in the market. Your questions will help reveal the real issues, leading your customer to realize what next steps they need to take, and having also heard how your offering can help get them there, build a stronger trust.

• What’s important to you when making a buying decision on a product/service?

• Who do you feel is your biggest competition?

• What do you know about (name of other competitors)?

• How much do you know about our company?

• What have you found the most compelling about working with our company?

• What are your greatest concerns about working with our company?


Generally done together, this is your opportunity to show your customer or prospect what you’ve got that they can’t do without. So while you’re doing the demonstrating, also keep them engaged and feeling like you’re no longer selling (push), but they are buying (pull).

• How do you see this fitting in with your needs? Building your business?

• How have other (similar) products or services fallen short?

• What other applications can you see for this product?

• Given a trial period with this product/service, how could we help set you up for success?

• What obstacles can we help you overcome in purchasing this product/service?


The popular saying is A-B-C...Always Be Closing. If you’ve done your best with the above steps, closing should be much easier, but never depend on it or assume anything. This is your final chance to make a great impression and if you’re still talking with this customer, you don’t need to oversell, but still show that it isn’t about you, but about solving their problems. While we’ve been shying away from yes or no answers, Dale Carnegie talks about getting the yes from someone to start of on a positive footing. This leads them to more yes answers as you continue to ask questions and builds on a feeling of partnership and goodwill rather that one of hard selling.

• Are you still committed to solving this problem?

• In reviewing everything we’ve talked about, did you feel more strongly about using product X or product Y (or both)

• How did you feel about the fit for this product/service within your company?

• It does seem that our product or service will solve your problem, and I know delaying a solution is costing you money/time/productivity. How soon did you want to get started on resolving this pain point?

• How else can I help you?

• Who will need to review the contract?

As you build your own arsenal of questions, asking them early and often throughout the sales process becomes a natural habit. Think about children we asked hundreds of questions in a day, but somehow grew out of that. This is an exercise in rebuilding your own curiosity about others, really, and you may find it uncovers that desire for discovering answers that help broaden your whole world, and not just the world of your business.