How to Ask Good Discovery Questions While Maintaining Your Authenticity

Preserving authenticity is fundamental for generating a sale. Ask these simple discovery questions in your next client meeting. 

Today’s post is by Jeff Kirchick, Vice President of Enterprise Sales at Next Caller, and author of Authentic Selling: How to Use the Principles of Sales in Everyday Life (CLICK HERE to get your copy).

In traditional sales programs, you are typically taught to ask certain questions. The problem with being taught to ask certain questions is that you are fundamentally changing your behavior when you ask them. Generally speaking, you are probably changing your behavior out of self-interest – to generate a sale – rather than asking in the interest of the customer. And the thing about sales is that you should always be focusing on the needs of the customer. Why? Because sales is not about you. Sales is about them. So what questions would you normally ask someone when you are trying to figure out what is best for them?

In my new book, Authentic Selling: How to Use the Principles of Sales in Everyday Life, I discuss the importance of authenticity relative to the usual tips and tricks you might learn in a formal sales training program. The rationale for this is two-fold: first, people just register authenticity easily. and authenticity is the key to building trust, which is fundamental for generating any sale; second – and perhaps more importantly – machine learning and artificial intelligence have teamed up to create a wave of automation which is trickling into the sales world, and salespeople will need to embrace what makes them human in order to preserve advantages over machines.

We can start with what ‘not’ to do. For me personally, I am not particularly fond of the “BANT” model: Budget, Authority, Need, Timing. This is where the seller asks a series of questions to “qualify” the lead to ensure that it is worthwhile to even have a dialogue. Qualifying leads is a good thing in theory. But when people give you their precious time to learn about a product, chances are that they do not want to be interrogated about whether or not they have authority to make a purchase. When these questions are asked right out of the gate, it renders an impression that the seller is only interested in fulfilling their own agenda.

What I have found in my career is that you often earn the right to the information you need by building strong, authentic relationships with the client. In order to do that, you need to really care about them the way you care about a friend. What questions do you ask your friends when they need your help? This is a good thing to ask yourself when you are considering what questions to ask a client. Without further ado, I’ll offer a few simple suggestions for great, authentic discovery questions:

What is something that could happen that would make this a good (or bad) experience for you?

I like asking this question when I interview people. It’s really two questions: one good thing, one bad thing. On one hand, it gives me insight into the thing the person is really hoping for. At surface level, you might get an answer like “I want to advance my career,” but asking this question forces someone to tell you what tangible action step would have to happen to signal to the individual that they accomplished that. The same goes for the “bad” thing. What is their greatest fear? This is really the best way to find out what reservations someone has working with you – there is no nicer way to ask than this.

How does it make you feel when X/Y/Z problem happens to you?

It’s one thing for someone to have a problem that you can solve. It’s another to understand how their pain point makes them feel on a day-to-day. If you are fixated only on selling your solution to solve someone else’s pain, you are missing half the opportunity to build the relationship. What is truly at stake for the individual? You do not know until you ask. This question makes the conversation less about a problem and a solution and instead makes it more emotional and personal, a conversation between two people about feelings and how to improve their lives. Much of good selling is about peeling the onion as much as possible. There is no better way to quantify someone’s struggle than by seeking to understand how their struggle is making them feel.

Why are we here?

No, not the existential question. More the literal question: “What brings us here today to have this dialogue?” It can feel strange sometimes to be so bold, but I like to be self-aware and get it out of the way so we have a common language to work off of on what we are looking to accomplish. Are we here because you have a white-hot pain point you need to solve, or because someone on my team has been bugging you for months to take a meeting with us? The context matters. In the situation of the former, I need to learn more about the pain point. In the situation of the latter, I probably need to cut to the chase a bit and be mindful of the other person’s time.

And there you have it – a few simple questions to ask that can go a long way for you in understanding how to help others. Next time you sit down for a sales pitch – or next time someone just solicits your advice – ask yourself how you can ask great questions that ultimately serve to help the other person more than they serve your wallet. Chances are, actually helping the other person will come back to you in a positive way.

Jeff Kirchick is Vice President, Enterprise Sales and an early employee at Next Caller, a Y-Combinator backed technology company that sells authentication and fraud prevention technology to Fortune 500 brands across the United States. He has had unparalleled sales success for over a decade and enjoys the opportunity to help mentor and coach younger sales professionals looking to get their start. He is a big believer in saying what you have to say whether it is going to be popular or not.

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