AI Coach: find and fix deal issues before they result in closed-lost using AI

Discovery Questioning

Sales Questions That Impress Executives

14 min
Average Score

Chris Orlob


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In this session, we will delve into the art of initiating meaningful discovery conversations with buyers who may not be actively seeking solutions. As a sales account executive, you'll often encounter situations where your potential buyers have latent or active pain points but are not yet exploring options. This presents a unique challenge in the sales process – how do you uncover and develop their pain points while warming up a somewhat resistant prospect? Let's explore three effective techniques to address this challenge.

1. Context-Led Questions: The Power of Preceding Questions with Insights

Definition: Context-led questions are those preceded by sharing an observation or insight based on pre-call homework. These observations provide context for the question, demonstrating your commitment and expertise.

The Tim Ferriss Technique

Tim Ferriss, renowned author and podcast host, excels at this technique in his interviews. He doesn't ask generic questions but rather shares astute observations before posing questions, leading to richer responses from his interviewees. You can employ a similar strategy in your sales conversations.

Applying Context-Led Questions in Sales

You can draw insights from three key areas:

  • Company: Share observations about the prospect's company, such as recent developments or decisions.
  • Industry: Discuss broader industry trends that relate to their business challenges.
  • External Factors: Consider external factors like the economy, financing, or market conditions that might impact their business.

Now, let's see how this works with examples from each category:

Company Observation: "John, I noticed your company's recent move into the sales engagement category. Could you tell me what drove this decision?"

Industry Insight: "Emily, it seems the customer success technology industry is shifting towards expansion. How does this trend affect your team, especially in terms of product development?"

External Factors: "Vanessa, with the current economic situation affecting hiring, how is your sales approach adapting? What changes are you considering?"

Remember, these observations should lead to discussions about problems you can solve.

Keys to Success

  • Relevance: Ensure your question ties back to the problem you can address.
  • Gain Permission: Seek consent to explore specific areas.
  • Avoid Tunnel Vision: Stay open to redirecting the conversation if needed.

2. The Discovery Prompter Technique

Stay tuned for an upcoming video lesson that will delve into the Discovery Prompter technique, another powerful method to warm up cold buyers and trigger meaningful discussions.

3. Jump In When the Buyer is Ready

Sometimes, you may sense that your buyer is already receptive and open-minded. In such cases, it's okay to skip the fancy techniques and dive right into discussing their pain points in areas you can resolve. Trust your judgment and adapt your approach accordingly.

Your Exercise: Applying Context-Led Questions

Now, it's time to put theory into practice. Follow these steps:

  • Choose an Upcoming Call: Select a forthcoming discovery call where you'd like to employ the context-led question technique.
  • Plan and Write: Craft a context-led question based on your research about the prospect's company, industry, or relevant external factors. Keep it simple if you're new to this technique.
  • Try It Out: Use this question in your call with the customer. Reflect on what went well and where improvements can be made.
  • Assessment: Document your experience and self-assessment. Analyze what worked and what didn't. Consider how you can refine your approach for future conversations.

In conclusion, mastering the art of starting discovery conversations with buyers who may not be actively seeking solutions is crucial for sales account executives. Context-led questions, as demonstrated by Tim Ferriss, can be a game-changer in engaging your prospects and uncovering their pain points. Stay tuned for the next video lesson on the Discovery Prompter technique, and remember to practice and refine your skills to become a more effective sales professional.

Watch this session to learn more about this topic and enhance your ability to warm up cold buyers and drive meaningful discovery conversations. Your success in sales hinges on your ability to connect, engage, and address the unique needs of your prospects.

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