How to Ask Great Drill Down Questions

Open ended questions that connect and get buyers talking are essential. And they have to be asked in a skillful way, with good framing and value statements embedded to have the greatest effect. But drill down or follow-up questions are where the true art of great questioning begins. They separate the great sales people from the good ones.

Drill down questions require a higher skill level than open ended questions. You have to listen carefully to what the buyer is saying, and then be quick on your feet to ask good, relevant follow-up questions that demonstrate understanding, convey insight and deepen the conversation.

When it’s done right

When drill downs are asked effectively by a salesperson with the right skills, it’s a beautiful thing to watch. The conversation flows with the buyer pouring out critical information needed by the seller to help the buyer move forward. Buyers feel completely understood and respected, and the relationship strengthens.

When it’s done wrong

On the other hand, and I’ve seen this far too often, drill down questions asked by under skilled or poorly trained sales people are hard to watch. It’s painful. Abrupt changes in conversation direction, awkward silences as sellers check their notes and mounting buyer impatience damage rapport and stifle dialogue. It usually doesn’t end well.

How to become good at drill down questioning quickly

First, what not to do.

The biggest, most misguided complaint I hear from sales people struggling to become good at drill down questions is:

“I need more product knowledge. I don’t know enough about our products to ask good drill down questions.”

This is absolutely wrong. Product knowledge is not the key—it’s understanding the buyer: their situation, their goals, their fears and challenges, and their aspirations.

Is product knowledge important? Yes, but it pales in comparison to demonstrating understanding to your buyer. Understanding your buyer and the outcomes your products bring is far, far more important. In fact, if you start spouting product related questions and statements, the dialogue will go right to the weeds before you’ve ever had the chance to convey understanding and value.

Now, let’s discuss a quick path to better drill down questioning.

1. Focus on buyer personas

Come prepared to the discussion knowing your buyer’s persona: their key business drivers, goals and objectives, main challenges, common obstacles to change, etc. Every prospective company and buyer is different, but there is much common ground you can leverage to ask very relevant questions, convey insight and demonstrate understanding.

For more on personas, see my previous article "Why buyer personas are so powerful".

2. Create a drill down question map

Around each of your open ended questions, map high level drill down questions that relate to the overall topic. Don’t get too detailed, just add keywords and phrases to the map that prompt your follow on questions. A great technique is to use one PowerPoint slide per topic, with the open ended question in the center, and drill down phrases and keywords surrounding the main question.

3. Practice using role play

The best sales training for just about any situation is role play. This is especially true for questioning skills. Nothing can replace role play practice.

Practice by starting with an open ended question, and then see how well you can keep the role play partner engaged with good follow up questions.

Here’s an example of a good drill down question:

“Jill, you mentioned you’re worried about how limited your team’s visibility is into how sales is using your marketing materials in the field. This is something we hear quite a bit and can definitely help you improve. Could you talk about some of the specific areas or scenarios that concern you the most?”

Practice this technique and you’ll be amazed at how a little improvement in drill down questioning dramatically deepens conversations and improves your understanding. Once you becoming really good at questioning, B2B sales becomes a lot easier, and a lot more productive. It’s one of the main reasons why great sales people are great.

Hope you have your best year ever.