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Preparation Is Key to a Successful Sales Questioning Strategy

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Asking good sales questions is a derivative of good preparation. That’s a given in my book. And I’ll give you a personal example that proves the point.

I was working on a sales opportunity with what has become one of Richardson Sales Performance’s largest clients. We were nearing the final presentation and would be going head-to-head against a major competitor in our industry. Our team would be presenting to a dozen people, and so we focused considerable energies on preparation. Before we even entered the room, we wanted to know what those 12 were thinking so that we could be sure to address their expectations in our questioning and presentation strategy.

I contacted each one of the 12 and was able to speak with ten people. In these individual conversations, I thanked them for their time and assured them that it would be time well spent because what is important to Richardson Sales Performance is what is important to them. I told them that I wanted to hear their individual views before meeting en masse so that I could understand their critical objectives for the meeting, what would be important for them to hear, and what they needed to walk away from the meeting knowing in order to make their decision.

When we all sat down together, our team had a good idea about the level of questions that we needed to pose and the insights that we needed to bring. We weren’t flying by the seat of our pants; we weren’t throwing out trial balloons; we were addressing what they told me they wanted to know. Our presentation was laser focused, and we were able to link different points to the specific issues raised by individuals. We won the business, largely because we talked about what was important to the customer, not by talking about what was important to Richardson Sales Performance. We won because of thorough preparation that informed our questioning and presentation strategy.

At Richardson Sales Performance, our model for preparation has three layers:

  1. Strategic preparation — thinking about the objectives of the meeting and visualizing the meeting at every stage, from Opening to Need Dialogue through to Solution and Close
  2. Client preparation — understanding the client’s objectives, strategies and political dynamic, which involves understanding the individuals involved in the meeting and their company
  3. Technical preparation — knowing the features and benefits of your products and company, the industry and the market
As I prepare for any client meeting, I always have a collection of questions that are top of mind. But, my plan is to be in the moment and ask what’s relevant at that point rather than sound scripted. If I show up with a list of set questions and ask them one after another, then I’m an order-taker. Anyone can do that. Instead, I prepare questions in basic categories that are designed to get to the client’s root issue. Some key questioning areas include strategy, infrastructure, culture, knowledge, attitude and skills.

With thorough preparation and a carefully crafted questioning strategy, salespeople are better positioned to conduct a dialogue with clients in which they sound well-informed, thoughtful and credible.

Clients can see through a lack of preparation. They spot when salespeople are winging it. They dismiss those who “show up and throw up,” just doing a data dump on their own company, often with a generic presentation.

The analogy I use is trying to build an airplane while flying it. It can’t be done. You have to build it on the ground and then fly. With client meetings, you have to prepare thoroughly before each one. That’s the only way to craft an effective sales questioning strategy that adds insights and builds credibility.

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