The Audible-Ready Sales Podcast

Episode Title: Attaching to the Biggest Business Problem
Air Date: September 24, 2024
Host: Rachel Klepp Miller (Force Management)
Guest: John Kaplan

Overview

This episode explores the critical sales skill of “attaching to the biggest business problem” within customer organizations. Rachel Klepp Miller and John Kaplan break down what it means, why it’s essential for B2B reps—especially in technical sales—and, most importantly, the tactical “how” behind executing on this best practice. The conversation emphasizes the intersection of technical requirements and business outcomes, actionable strategies for deeper discovery, and the importance of multi-threading in enterprise sales.

Key Discussion Points & Insights

1. Defining Your Mission as a Seller

• Reps must focus on surfacing and attaching to their customer’s most pressing business issue, not just technical details.
• Quote [01:31]:
  John Kaplan: “You have to wake up every morning and tell yourself that your job is to attach yourself to the customer's biggest business issue.”
• Relevance extends to all sales roles; if you don’t believe this is your job, reconsider your approach.

2. The Who: Identifying the Right Contacts

• Often, initial contacts can’t provide perspective on company-wide business issues, presenting a challenge.
• If a contact can't answer key questions, reps shouldn’t immediately move on—dig deeper and attempt to bring these contacts along as allies.
• Quote [03:12]:
  John Kaplan: “If I'm talking to somebody, they don't have the answers... The best discovery questions are when you're asking people questions that they have not already thought about.”
• Bringing initial contacts along when navigating the organization leads to warmer conversations and helps in building internal champions.

3. Navigating Internal Politics & Multi-threading

• Assess internal political dynamics before moving higher or across the organization.
• Balancing courtesy and effectiveness: inform contacts as you expand your network, but don’t let fear of “going around” paralyze you.
• Quote [06:27]:
  John Kaplan: “Your job is to not piss anybody off. Your job is to not make anybody feel bad. Your job is also to map customer requirements to your solutions and sell stuff.”
• Sometimes you need to move on without certain contacts (e.g., gatekeepers or blockers), but always aim for collaboration where possible.
• Quote [14:19]:
  John Kaplan: “You have to accept the fact that in today's world, you have to be multi-threaded on sales campaigns... If they're not multi-threaded, I guarantee it's a red flag.”

4. Bridging Technical and Business Worlds

• Reps must “stand in both worlds”—with one foot in technical discussions and one in business conversations.
• This is especially significant in technical or IT sales, where aligning technical solutions with measurable business outcomes is often a CIO-level concern.
• Quote [09:32]:
  John Kaplan: “Your job is to stand in both worlds and bring them together... connect technical requirements and connect them to business outcomes.”
• Being able to bridge this gap remains a consistent, high-priority challenge for decision-makers.

5. Discovery: Going Deeper to Find Real Pain

• Reps often stop at the level of challenge or concern, never reaching the real business pain.
• Use “TED” discovery questions: Tell me about…, Explain for me…, Describe for me… to unearth specific, real-world scenarios of pain.
• Quote [11:15]:
  John Kaplan: “It's our job to implicate the pain... Sometimes people jump off the pain. They get to a challenge or a concern, but they don't get to the pain.”
• Example follow-ups: “Who cared about that?”; “How did you communicate that back to the customer?”; “What are you doing to make sure that never happens again?”
• The goal is for customers to “stand in the moment of pain” and self-identify urgency for change.

Memorable Quotes & Notable Moments

• [01:31] John Kaplan:
  “You have to wake up every morning and tell yourself that your job is to attach yourself to the customer's biggest business issue.”

• [03:12] John Kaplan:
  “The best discovery questions are when you're asking people questions that they have not already thought about.”

• [06:27] John Kaplan (on multi-threading):
  “Your job is to not piss anybody off. Your job is to not make anybody feel bad. Your job is also to map customer requirements to your solutions and sell stuff.”

• [09:32] John Kaplan:
  “Your job is to stand in both worlds and bring them together... connect technical requirements and connect them to business outcomes.”

• [11:15] John Kaplan (on deep discovery):
  “It's our job to implicate the pain... Sometimes people jump off the pain. They get to a challenge or a concern, but they don't get to the pain.”

• [14:19] John Kaplan:
  “You have to accept the fact that in today's world, you have to be multi-threaded on sales campaigns... If they're not multi-threaded, I guarantee it's a red flag.”

• [14:19] John Kaplan:
  “Give them all the credit. You just need the money. Implicate challenges to real life pain. Go deeper. Use those TED questions.”

Timestamps for Critical Segments

• 00:00 — Framing the episode: Focus on connecting technical requirements to business outcomes
• 01:31 — The central seller’s mindset: Attaching to big business issues
• 03:12 — How to handle contacts who don’t know broader business issues
• 06:27 — Navigating internal politics, bringing people along, multi-threading
• 09:32 — The two-foot analogy: Standing in both technical and business conversations
• 11:15 — Going deeper in discovery: From challenge to pain using TED questions
• 14:19 — The power of multi-threading and making change happen in accounts

Actionable Takeaways

• Anchor every sales conversation to the customer’s biggest business issue.
• Move beyond technical pain; always seek the downstream business implication.
• Proactively “multi-thread” inside customer organizations—move up, down, and across, ideally with allies or champions.
• Use deeper, real-world scenario questioning (TED) to implicate pain and create urgency.
• Don’t hesitate to move past non-collaborative contacts, but aim for courtesy and inclusion where possible.

Bottom Line

• Sellers must believe their role is to unite technical challenges with business outcomes.
• Real sales progress comes from going beyond the surface—deep discovery, multi-threading, and emotional engagement of multiple stakeholders.
• [15:54] John Kaplan:
  “You need to connect technical pain to business outcomes. You must bring those two worlds together... you have to believe that's what you do for a living. That's it.”