The Audible-Ready Sales Podcast

Episode: Avoid Getting Overwhelmed with Technical Discussions
Date: December 6, 2022
Host: Rachel Clapp Miller
Guest: John Kaplan

Episode Overview

This episode of The Audible-Ready Sales Podcast tackles a key challenge many sales professionals face: confidently selling complex, technical solutions—especially when their buyers are industry experts. Rachel Clapp Miller and John Kaplan discuss strategies for balancing technical details with business relevance, leveraging internal resources, and remaining effective (and confident) even when operating outside one’s comfort zone. The conversation offers practical, actionable advice for any seller navigating high-stakes, complicated sales conversations.

Key Discussion Points & Insights

1. The Challenge: Selling Complex Solutions to Experts

• Selling technical, complicated solutions—often in unfamiliar industries or to expert buyers—can feel intimidating, especially for new sellers.
  • Rachel Clapp Miller shares: New sellers often feel overwhelmed by the expertise of their buyers or the complexity of the solutions they offer (00:44).

2. The Importance of Being Both Technical and Business-Oriented

• Success requires knowing when to focus on technical details and when to focus on business outcomes.
  • Quote (John Kaplan, 00:01):

    "You need to understand when to be technical, you need to understand when to be business oriented, and you need to be good at both."

• Sellers should focus first on understanding the buyer’s key business problems—not just product features.
  • Quote (John Kaplan, 02:50):

    "The key components that will matter to these buyers or experts...I’m constantly looking to make it just more about them and to understand them. Not just about the features and functions and differentiation...I need to understand the challenges that the buyer is facing."

3. Structured Approach to Grounding Yourself

• Step 1: Identify and understand the customer’s business problems (“What is the problem?”).
• Step 2: Examine the implications of the problem—the negative consequences—by asking, “So what?”
• Step 3: Understand and influence the decision criteria with your solution’s technical differentiation.
  • Quote (John Kaplan, 04:04):

    "When you find out this is a problem...write down on a piece of paper, 'so what?'...Understand how big of a problem that is. Then...focus on getting that into the decision criteria."

4. When to Get “In the Weeds” (and When Not To)

• There is a right time for technical deep-dives; just as important is knowing when to elevate the discussion.
  • Quote (John Kaplan, 05:28):

    "In this podcast, there is a time to get in the weeds, and there's a time to rise above the weeds...You get delegated to those that you sound like. So you need to get technical with technical people...and you got to get business focused with business people."

  • Key Point: Get technical with technical buyers, stay business-focused with business stakeholders.

5. Leveraging Internal Resources

• Don’t hesitate to lean on product, marketing, or sales management colleagues for clarity—especially when trying to connect technical challenges to business outcomes.
  • Quote (John Kaplan, 06:54):

    "There are people inside your company that understand this very, very well—marketing people, product marketing people, your sales management team...If you're struggling to attach to the biggest business issue, just call it out, don't try to hide it, just call it out."

• John’s principle: admit knowledge gaps and proactively seek help.
  • Quote (John Kaplan, 09:06):

    "They tell you a lot, hey, fake it till you make it. You don't want to do that here...You want to be clear and open and honest about what you know and what you don't know and let others around you coach you."

6. The Value of Openness and Asking for Help

• Creating a culture of vulnerability accelerates growth and learning.
  • Quote (Rachel Clapp Miller, 09:47):

    "When I have, like, come far in my career, it's always been starting from a place where I've said, 'I don't know how to do this. Can you help me?'"

• Slowing down to fill gaps in understanding leads to greater success in the long term.

7. The Bottom Line: Bridging Technical and Business Worlds

• Top reps position themselves at the intersection of technical issues and business outcomes, connecting the two for the customer.
  • Quote (John Kaplan, 10:11):

    "The most elite reps position themselves right in the middle...You have to position yourself in the middle between technical issues and business outcomes...That's what the most elite sellers do—they connect technical issues to business outcomes."

Notable Quotes & Memorable Moments

• "You get delegated to those that you sound like."
  • John Kaplan, 05:28.
    (Meaning: Technical talk for technical people, business talk for business stakeholders.)
• "It's okay not to know the answer...but it's not okay not to be doing anything about it."
  • John Kaplan, 07:55.
• "Fake it till you make it? You don't want to do that here."
  • John Kaplan, 09:06.
• "Top reps clasp technical issues and business outcomes together—they don't choose just one."
  • Paraphrased visual from John Kaplan, 10:11.

Timestamps for Key Segments

• 00:44: Rachel introduces the challenge of selling to technical experts.
• 01:28: John’s personal story—selling complex software with no technical background.
• 02:50: How to use enablement to focus on buyer problems.
• 04:04: Breaking down problem, implication, decision criteria, and differentiation.
• 05:28: When to get technical vs. business-focused.
• 06:54: Leveraging internal resources and being honest about knowledge gaps.
• 09:06: The importance of authenticity over “faking it”.
• 10:11: The “middle ground” that elite sellers occupy.

Final Takeaway

Elite salespeople excel at both technical depth and business relevance. They don’t shy away from complexity, but instead...

"...connect technical issues to business outcomes. This is a must if you want to rise above the noise or get out of the weeds."
(John Kaplan, 10:11)

Above all, honest self-assessment and the willingness to seek help are key to mastering complex sales situations.