Dear Growth Molecules: As a CSM, how do I ask effective probing questions to uncover a customer's intended business outcomes?

By: Hailey Mahoney & Sabina M. Pons

Asking effective probing questions is a critical skill for Customer Success Managers (CSMs). When it comes to understanding a customer’s intended business outcomes, the right questions can help you uncover valuable insights that will allow the tailoring of solutions to meet their needs. Meeting their needs is the way to provide value which is the primary goal of a software-as-a-service technology solution. When Alison Wood Brooks of Harvard Business school studied conversations, a foundational insight was uncovered: people don’t ask enough questions. If we’re not taking the time to ask our customers effective probing questions – how can we ensure our customers are successful? Presented below are six best practices for asking probing questions that will help CSMs get to the heart of what their customers are trying to achieve. 

Understand Your Customer’s Needs and Background

Before you start asking probing questions, you need to have an understanding of your customer’s organization, history and needs. This ensures that you arrive prepared for calls, ready to ask appropriate and relevant questions.

Do you know your customer’s problem? Seventy percent of purchasing decisions are made to solve a specific problem. In order to understand the current problem, review past interactions to gather information on their company, industry, goals, achievements, and/or reasons for choosing your solution. A quick LinkedIn search when a new contact is introduced, or a Google search of the company news, can yield insightful results for understanding the person and/or the organizational climate of the customer with whom you’re speaking. If applicable, also analyze their system usage and specific use cases in your product to understand whether they are demonstrating high or low adoption, or on track to achieve their goals. 

Start With Open-Ended Questions

According to the Nielsen Norman Group (NNG), a global UX research firm, planning properly structured questions is key. For example, their studies have found that open-ended questions with words such as “how,” “what,” “when,” “where,” “which,” and “who” are most effective in soliciting meaningful responses. Conversely, The NNG suggests avoiding using “why” questions, as people tend to come up with a rational explanation, even if they don’t have one. “Why” questions are typically appropriate when seeking feedback or ratings. Instead, it’s better to ask for more information with a prompt such as “Please tell me more about that.” It’s also recommended to aim for collecting stories rather than one- or two-word responses. 

The open-ended style questioning typically results in healthy discussion, which in turn, yields shared insights and problem solving. This is a win-win for both you and the customer. Examples of open-ended questions include:

  • What are your business objectives for the next year?
  • What do you hope to achieve with our product/service?
  • How do you envision our solution fitting into your overall strategy?
  • Have there been any shifts in the reporting structure at your organizations?
  • What new problems are you tasked with solving this year? 

Follow Up With Specific Questions

Once you have a general sense of what the customer is trying to achieve, it’s time to dig deeper. By asking follow-up questions that are specific, and perhaps tied to the most intriguing parts of a customer response, additional clarity will be gained. According to a Forbes article, asking follow-up questions can encourage individuals to delve deeper into their thoughts and convey the reasoning behind their viewpoints. Another byproduct of follow-on discovery questions shows your customer that you value their opinions and are engaged in active listening. 

Examples of specific questions that can help people elaborate on their ideas include:

  • Can you give me an example of a problem you’re currently experiencing?
  • How do you measure success in this area?
  • What challenges have you faced in achieving this goal in the past?
  • How do you see our solution fitting into your overall strategy?
  • What specific features or capabilities are most important to you?
  • Can you walk me through how you currently approach this problem and what’s not working?

Once you have a better understanding of the customer’s intended business outcomes, CSMs will be poised to drive toward enablement of those key customer goals.

Use Reflective Listening

Reflective listening is a powerful technique that involves paraphrasing what the customer has said to confirm your understanding and show that you are actively listening (also known as “mirroring”). This technique can also help you uncover any misunderstandings or areas where you need to clarify your understanding. Examples of reflective listening include:

  • If I’m understanding correctly, your main goal is to increase revenue by 20% in the next year. Is that right?
  • It sounds like you’re really looking for a solution that will help you streamline your operations and reduce costs. Am I correct?

Summarize And Confirm

At the end of the conversation, it’s important for CSMs to summarize what was learned and confirm their understanding of the customer’s inputs. This can help ensure that there is mutual understanding and that a solution can be provided. A Forbes leadership contributor advises to begin with the “I” perspective. This demonstrates responsibility for the perception of the customer’s words, which may differ from what they actually said or meant to convey. This approach fosters transparency, strengthens trust, and enables a CSM to adjust any incorrect assumptions that may have been made. In this case, it’s okay to ask a closed-ended question to receive a “yes” or “no” answer.

Examples of summarization and confirmation include:

  • To recap, I’m hearing that your main goal is to increase revenue by 20% in the next year, and you’re looking for a solution that will help you streamline your operations and reduce costs. Is that correct?
  • Based on what you’ve told me, it sounds like the most important features for you are X, Y, and Z. Am I correct?

In conclusion, asking effective discovery questions is essential for uncovering a customer’s intended business outcomes and in turn, showing how your solution can make them successful. By starting with open-ended questions, following up with specific questions, using reflective listening, and summarizing and confirming, CSMs will have a strong understanding of their customer’s needs and provide them with a solution that meets their goals.

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About The Authors:

Sabina is the Operating Partner at Growth Molecules™, a consulting firm that helps B2B SaaS companies simplify customer success with actionable processes and scalable programs. With a 20-year career in global CS and CX, Sabina is known for building teams from start-up to grow-up, for scale via client adoption, expansion, retention and loyalty programs. She has earned her MA in Communication & Leadership from Gonzaga University, and her BA in Public Relations from the University of Southern California, and is co-writing a book about working moms in technology. 

Hailey is the Manager of Customer Success Success at (SurveyMonkey). As a tenured Customer Success professional, Hailey has a track record of consistently improving customer retention through the implementation of effective strategies and programs. In her current role, she directly manages two teams of Customer Success Managers, focusing on driving adoption, maturity, and growth for our customers. Hailey has  strong communication skills and the ability to build relationships with clients, which has allowed her to exceed performance goals and drive positive business outcomes. 

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