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Critical Thinking Skills Examples in Sales: Asking Questions

This is part three in a series of posts about why and how to build critical thinking skills you can use to excel in selling. Be sure to bookmark the CONNECT2Sell Blog or subscribe to our weekly newsletter so you won’t miss these posts. Each one offers additional ways to build your mental might. 

The critical thinking skill we’re focusing on in this post is asking more purposeful questions. Sure, anyone can ask questions. In the typical sales process, there’s a step dedicated to asking questions. But asking quality, high-value, effective questions is a whole other story. Not everyone can do that. Successful sellers work to perfect the questions they ask, using critical thinking skills to craft questions that advance the sale and to know what to do with the responses given to questions asked.

Critical Thinking Skills ExamplesWe first wrote about the importance of purposeful, high-quality questions in the 2013 bestseller DISCOVER Questions® Get You Connected.  That book has been named one of “The Top 20 Most Highly Rated Sales Books of All Time” by HubSpot because it makes it plainly lays out what sellers can do differently to make every question they ask more effective. The book is based on research with buyers and examples of questions asked by real sellers.

When it was released, it wasn’t directly connected to critical thinking skills. That competency and phrase aren’t in the book at all. Only in hindsight, with sellers around the world sharing their experiences after reading it, did it become clear that the shift wasn’t just in crafting questions. It’s all about thinking critically about how you gather information and what you do with it.

There are eight purposes for asking questions (not just in sales, but anywhere!). Understanding the purpose for asking a question is, in and of itself, an exercise in critical thinking. The acronym, DISCOVER, provides a way to remember these eight purposes for asking questions:

  • Data Questions: the purpose is to gather facts and provable information. How many employees do you have?
  • Issues Questions: the purpose is to check on your relationship and find out how to improve it. What can we do to improve our service to you?
  • Solution Questions: the purpose is to plant seeds about alternate ideas. What are your thoughts about bundling these products for an enterprise-wide solution?
  • Consequence Questions: the purpose is to probe pain points. What happens if you don’t reach that revenue target?
  • Outcome Questions: the purpose is to understand hopes, dreams, plans, goals. What are your division’s goals for the new fiscal year?
  • Value Questions: the purpose is to zero in on what matters most. Of the three goals you’ve shared, which one is most urgent and important for you to achieve?
  • Example Questions: the purpose is to make something more relatable or tangible. What’s the difference between your typical customer’s experience now and two years ago before you first implemented a full tech stack for customer success?
  • Rationale Questions: the purpose is to learn about the decision process. What will your top two criteria be as you compare vendors and select a new provider?


I Didn't Know that Asking Questions Was a Critical Thinking Skill! 

The Foundation for Critical Thinking says that “the key to powerful thinking is powerful questioning.”

They go one to describe the process of thinking and conclude that “questions define the agenda of our thinking. Our thoughts can take us in an infinite number of directions. The path of any conversation can also take detours and any number of turns. What steers a conversation and focuses our thinking is questions.

Questions determine the focus and direction of a conversation. That’s the first link between questions and critical thinking.

In sales, questions are also vitally important for extracting information that will be used to understand and meet each buyer’s needs. It takes critical thinking skills to craft effective questions that efficiently extract precisely the right information. Critical thinking and well-crafted questions yield solid, actionable information quickly. This powerful combination replaces discovery calls that sound more like aimless  and meandering fishing expeditions, one-sided qualifying, and survey-sounding lists of questions.

All of this is enabled by purposeful questions (which come directly from the process of critical thinking). That’s the second link.

Once a seller has asked questions and extracted information, the next link between those questions and critical thinking is knowing what to do with the information received. It takes strong critical thinking skills to piece together the bits of information, to ask incisive follow-up questions for clarity or magnification, and to connect the dots between the buyer’s needs and your solutions.

Finally, asking questions is essential for learning That’s why asking quality questions is not just a critical thinking skill. It’s THE critical thinking skill that will help you acquire all the other ones.   

These Critical Thinking Skills Examples Will Help You Be More Purposeful with Your Questions 

Consider these examples where critical thinking would have changed the outcomes. These are both real and recent examples from the field.

EXAMPLE 1: Seller misses a huge clue about what the buyer values (and loses the sale)

Seller: What are you expecting to see changing over the next quarter?

Buyer: We’re launching our ERP implementation and I’m going to be working some long hours

Seller: Oh? I’m surprised you don’t already have an ERP. When does that start?

Buyer: In 2 weeks, I’m taking a vacation first because I don’t expect to see much of my wife in the next few months. But if I manage this well, I think there’s a promotion in it for me.

Seller: Congratulations! I’m sure you’ll nail it. Back to your other need, though, for LMS content you can use for credits in your corporate university… What topics do you want to see?

Buyer: Well, we haven’t really mapped that out yet… In fact, I think we should wait until the ERP is in place. Why don’t you give me a call in 3 months?

Critical thinking about this vs. a narrow focus on making a sale would have prompted three realizations: this buyer is highly motivated to succeed and make a good impression on others, there’s likely a linkage between the ERP and the LMS systems we should explore, and time is precious to this buyer so they may appreciate a resource who can take some of the workload.

Questions that reveal this understanding and change the course of the conversation could include:

  • To get that promotion, what do you feel you have to demonstrate to others?
  • Tell me more about the ERP and how you want to see it working with your LMS.
  • What are your thoughts about saving time by working with a partner who can handle the LMS side for you?


EXAMPLE 2: Seller responds to the first need mentioned and never hears the bigger need

Seller: What do you hope to achieve with your advertising campaign?  

Buyer: We noticed today that our weekend traffic declined over the past two weeks…

Seller: We should heavy up your presence on Thursday and Fridays to get people thinking about  you even before the weekend.

Buyer: Right. But that sounds pricey when you say “heavy up.”

Seller: Let me run the numbers and find something that works for you. What’s your budget?

Buyer: I’m not ready to make a commitment or set a budget. We have a regional director’s meeting next week, and I have to develop a strategy for bringing in younger shoppers…

Critical thinking almost always includes asking questions for confirmation and micro-commitments before leaping to solution. A hasty response to a top-of-mind, peripheral need will always end in disappointment. No matter how amazing your solution, it won’t be compelling if there are other larger needs looming. And, in this case, that leap took the conversation off course and set off red-flag warnings about price for this buyer.

Questions that would have kept the conversation on course include:

  • What’s the impact of that decline in weekend traffic?
  • At this time of year, are these declines typical or is something more going on?
  • How critical is it to address the issue of weekend traffic right away?
  • How much of a decline did you experience?
  • In addition to boosting weekend traffic, what else do you need your advertising to do for you?


What both examples have in common is a lack of applied critical thinking. In the moment, each seller failed to look at the situation objectively, maintain composed and logical thinking, and let themselves get carried away by artificial urgency or adrenaline.

You can do better than that! All it takes is critical thinking so you can ask purposeful questions. In each example, a simple “Tell me more about….” would have changed everything. 


Next Steps for Using Questions Wisely

Just because questions come easily, naturally, or from sales training doesn’t mean they are purposeful, quality questions. Crafting high-yield, high-impact questions requires learning, practice and mastery.

The best questions come from knowing the purpose of the question. Why are you asking it? What do you hope to learn or understand or stimulate with the question? What will you do with the information you receive? Instead of merely asking questions, you have to invest time and thought into what you’re trying to achieve.

Don’t take question-asking for granted or treat it like it’s a no-brainer skill. It’s not.

Sellers who ask quality questions advance their sales faster and create value for their buyers just by asking questions. Buyers report positive experiences with sellers when they’re asked thought-provoking questions. The advantages of asking better questions include positively differentiating yourself and becoming more effective in selling.

It all hinges, though, on the critical thinking behind the questions.

Be sure to subscribe to the CONNECT Community newsletter for sales professionals so you’ll receive weekly access to this continuing series on critical thinking in sales. If you prefer to accelerate your learning about critical thinking skills, subscribe to our YouTube Channel and check out the full playlist for videos about all 40 facets of critical thinking.

You can also pick up a free chapter from DISCOVER Questions® Get You Connected. This book will teach you how to ask questions that set you apart. It will also explain the purposes of questions so you can put the critical thinking behind them. 

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Topics: Critical Thinking Skills Examples

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