Attaching to the Biggest Business Problem

Summary

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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

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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.

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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.

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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.”

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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

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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.

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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.”

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Transcript

[A]

When you wake up in the morning, not only do I want you to say, my job is to attach myself to the biggest business issue, your job is also to bring technical requirements and connect them to business outcomes.

[B]

You're listening to the Audible Ready podcast, the show that helps you and your teams sell more faster. We'll feature sales leaders sharing their best insights on how to create a sales engine that helps you fuel repeatable revenue growth. Presented by the team at Force Management, a leader in B2B sales effectiveness. Let's get started.

[C]

Hello and welcome to the Audible Ready sales podcast. I'm Rachel Klepp Miller. Today we are going to talk about finding the biggest business problem in the company, in your customer company. John Kaplan is a master, as you all know, at coaching reps to do this, and he joins me today. Hi, John.

[A]

Hey, Rachel. I'm excited about this one because for whatever reason, it's coming up for me every day. So it's a really common topic right now, so I'm glad to talk about it.

[C]

Yeah, and this topic has been coming up in our Ascender community. That's our online platform for sales reps and teams. We have a community there where people ask questions and it comes up frequently. All reps know they need to get to the biggest business problem. Right? That's not a challenge. You know you need to do that. However, the execution of doing that and the push to get higher often trips them up. And so let's try to provide some additional how in the conversation today.

[A]

That's awesome. So we're still in the context setting piece here, but for me, everybody listening to this, you have to wake up every morning and tell yourself that your job is to attach yourself to the customer's biggest business issue. So before we go on to some hows, I want you to just sit with that and say to yourself, I either believe that or I don't. And if you don't believe it or you don't think you have to. And maybe your job, I can't think of any jobs that don't need that. So I think you should be listening to exactly what we're talking about today. So we're going to be talking about getting to the right people and with the right information. And we're going to talk about doing that through discovery. And ultimately your job is to. I want you to think about this, too. I want you to think about two circles where they come together and there's an intersection in the middle, and that intersection is between where the technical problems and challenges for a Company connect to business outcomes, alleviate business problems and challenges. And when you wake up in the morning, you got to say, that's what I do for a living. I stand right in the middle of technical problems and business outcomes. And so I'm excited to talk to you a little bit more about that as Rachel leads us through some good navigation here.

[C]

Yes, my goal for the day. So let's talk a little bit about the who in these conversations. That makes a difference when you're trying to attach to the biggest business problem. What happens when your initial contact lacks a perspective of how they relate to the broader company. I know a lot of reps run into this like you're. You're asking the right questions as a salesperson, but the person doesn't know the answers. What do you do?

[A]

Yeah, that's such a good question. And I think it is. That kind of thing's coming up all the time is like, if I'm talking to somebody, they don't have the answers. You know, what do I do? There was an old saying when I was growing up in sales, if you're asking questions to somebody who can't answer them, go find someone who can. And I really like that. When I was younger, I liked that it gave me confidence and conviction, meaning I'm not going to suffer and stay with somebody that is unwilling to give me answers, that has tried to be a gatekeeper. But that's not the question you asked. So I want to be very clear. I think that that advice is not bad advice. I just want to tweak it a little bit. The best discovery questions are when you're asking people questions that they have not already thought about. So think about that. My goal is to ask people questions that they don't have the answer to or that they haven't thought about. And I don't want you to immediately run out of room just because they don't have. They haven't made that connection. Now you have to prepare yourself to ask questions that people haven't already thought about, and then you have to make a decision. Because sometimes you'll ask people questions that they won't have the answer to, and you have to think about, I still need the information now, why would I not try to figure out how to take that person with me? If it's a good question and you would expect that that person should be able to answer it, they're not answering it because they might not know the connection. This opens up the door for you to move in the account. But always consider bringing that Person with you on the move, I always like to say to myself, and I said it to customers too, before I ran out the door, I'd look back at the customer, I'd say, hey, you need to, you know, we established that I needed to go talk to so and so and blah, blah, blah. And I didn't just run out of the room. I said, hey, you need the answer to this too. Why don't you come with me? And here's what I learned, Rachel, is I found that when I brought people along while I was moving or they were actually bringing me along while we were moving, multi threaded in an account, the conversations were warmer. There was always someone who had context in the conversation. It was easier for me to get appointments for these next calls because I utilized those people that didn't have the answer to help me get to the next meeting. So again, I find that scenario happening a lot with technical sales, if you will. So we're asking technical people, typically business implication problems, and they struggle with it. And it's just, you know, there's no doubt, like your job as a seller is to connect technical problems to business outcomes. Don't miss an opportunity to bring somebody along with you. Make the call warmer.

[C]

Yeah. And you know, the political landscape is at play here as well. You know, you talk about bringing them with you. I'd love to hear your tips about how to do that. And then also like, do you ask for an intro to a higher up employee or do you just go around and see if you connect with somebody, which could have other implications. What's your advice there?

[A]

Yeah, it's really good because this is a, this is, we're talking about kind of skill and art a little bit. Look, 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. So I always first try to move around with people on the inside because that, it might not necessarily mean that, you know, you're bringing everybody along in a conversation, but you should always consider it. Again, I talked about warmer context, champion building. I've brought technical people to business outcome conversations and I've made it their idea. And you know, like my grandmother used to say, you don't need the credit, you need the money. And I think the people that are very, very savvy on relationships and how power and influence works inside of an account, you should always look to bring people along with you. Now, if you decide not to utilize somebody from a previous conversation, for example, there's gatekeepers that'll tell you you're going nowhere inside this company without me. Or I don't want you calling on that individual. Or they're just an idiot. Sorry, they're just an idiot. Or they're an enemy, which is somebody else's champion. You have to be savvy enough to figure that out. And sometimes you have to go alone, look to bring people along. But if people are trying to stiff arm you and keep you out of places, it tells me a lot. It tells me either they don't trust us or they don't understand what we're doing. Or the worst possible scenario is they understand very well what we're doing and they're trying to protect one of your competitors. And you just got to be savvy enough to figure that out. So I'm always careful not to tell you that you have to ask for permission for moving around an account because at the end of the day, I don't believe that. I don't believe I have to ask anybody's permission. I think it's common courtesy to let people know. And I think the smartest sellers figure out a way to get people emotionally connected to helping them move in the account. So again, when you ask a question they don't have the answer to, that they need to know, figure out a way to get help moving on, which includes stopping talking to them if they're purposefully holding the information from you. So I know that's kind of a ball thrown up in the air there a little bit, Rachel, but I think it's really, really important. I find that it's easier to move in an account when you're moving with hall passes, when you're moving with consideration, when you're moving with people inside the company. But I'm not telling. You can't be successful if you didn't bring somebody with you.

[C]

Yeah. And, you know, you mentioned the technical sale. Right. Which sometimes in those conversations they're important, but they can get us stuck too. So I think it's also important to say that you don't want to ignore the value that you can bring to the person with that technical solving a technical problem. But if you're solving technical pain, you're only doing one part. Right. It's still valid. But you want to multi thread the deal.

[A]

I really like the way you said that. I think it's a really, really good way to put it. And I want to use that analogy. I want you to look if you're listening right now and you have the ability to see your feet, I want you to look down at your two feet on the ground. And one of those, you know, one foot needs to be in the technical part of the organization and conversations, and the other foot needs to be in the business part of the organization. Your job is to stand in both worlds and bring them together. So when you wake up in the morning, not only do I want you to say, my job is to attach myself to the biggest business issue. Your job is also to bring technical requirements and connect them to business outcomes. Let's just use the simple fact. Every year they do a cio, and the big consulting firms will, you know, you can just Google it. Top CIO concerns. And for me, the last 20 years that I've been looking at it, they're asked the same question every year, and their top priorities are surveys. AI will be in there, blah, blah, blah. What's always in there in the top three to five is they always come back with align it to business as a top challenge. This is exactly what you do for a living. If you are selling technical sales or IT software that's connecting IT solutions to business outcomes. And that should tell you something. The average CIO will say, one of my biggest challenges is connecting it to the business. And that tells you something.

[C]

Yeah. John, I also want to go back to a sales fundamental that's related to this that we often talk about. You want to make sure that you're also digging enough with each contact right during your discovery and not just assuming that they don't know.

[A]

Yeah. So I love that, because you'll hear me say, and you've done this in some of the interviews we've done is that I say, go deeper, go deeper. And what we mean by that is to. It's our job to implicate the pain. And when we're talking about that, sometimes people jump off the pain. They don't ever get to the pain, Rachel. They get to a challenge or a concern, but they don't get to the pain. Let's talk about how to do that. This conversation we're having, there's a couple of ways to do it, or there's a couple of things we need to do. We need to implicate problems and challenges to real pain. And the way that you do that is you help the customer stand in the moment of the pain by asking them about real scenarios and find out who cares about it. So a lot of times what I'll find is sellers will jump off. Somebody will say, yeah, you know, that's a challenge for Us. And then all of a sudden the, you know, the seller gets excited and says, oh, that's the pain. That's not the pain. That's the challenge. The only way for you to understand the pain is to ask questions. You've heard us talk about TED questions before, and they're really not questions, they're more statements. But we call them TED questions. Tell me about, explain for me, describe for me. Because you got to make that customer sit in the moment of a real life example to get to the pain and ask questions like, who cared about that? So it was late and it was over budget. Who gave you feedback that that was a problem? How did you communicate that back to the customer? My favorite question is, what are you doing to make sure that that never happens again? And like those three questions right there, Rachel, you could be an unbelievable seller because you make that customer stand in the moment of pain. And a lot of times I'm just quiet and I look at the customer and basically they're telling me nothing. We're not doing anything. And they know they should be. So it just helps them stand in their moment of pain. Like we say, Rachel, it's like the more you tell me I have a problem, the more I'm going to resist you. But the more you ask great discovery questions that make me stand in my moment of pain, I'm going to convince myself I have a problem with urgency. So then we take that technical pain and we implicate it further into business pain. So we're always going to ask ourselves, what's the biggest business issue facing this customer? And we're going to force ourselves to find the answer and then attach to it. But it typically starts with technical challenges, which turns into real life pain with specific examples, which turns into business opportunities and business outcomes. For me, that's the how.

[C]

Right? That's it. That's it. There's a lot here, John, in this discussion today, critical skill for sellers to have. I think my goal with these podcasts, and I know probably for you too, is for people to just listen to them in the morning or whenever and just get like one nugget that's going to help you be a better seller that week, that day. And I think you've done that. You've definitely done that here today. Maybe a couple of golden nuggets for people. I'd love for you to wrap us up with a bottom line.

[A]

Okay? So for me, you have to accept the fact that in today's world, you have to be multi threaded on sales campaigns. It's really rare. If you're not multi threaded. I can't really think of any of them that I'm involved with or any of them that I've heard, any of the people that I interact with. If they're not multi, threaded, I guarantee it's a red flag. So just know that you got to move in these accounts. You got to move up and down. You got to move down and up. You've heard us talk about M and W before. You got to move. You got to ask questions that they've not thought about. And if they don't have the answers, you got to go get them. But try to bring people along with you. Get people emotionally connected to the problem and give them the credit for helping you connect to somebody who can connect it to the business implication. Give them all the credit. You just need the money. Implicate challenges to real life pain. Go deeper. Use those TED questions. Tell me about. Give me an example. Describe for me. Those are great ones to do that and then the Uber thing that we've been talking about all this podcast is you need to connect technical pain to business outcomes. You must bring those two worlds together. If I'm on an airplane, somebody says, hey, you know, what does your software do? It creates opportunities for technical challenges to connect to business outcomes. I mean, at the very basic fundamental you have to believe that's what you do for a living. That's it.

[C]

Thank you, John.

[A]

You're welcome. Go get them.

[C]

All right. Thank you to all of you for listening to the Audible Ready Sales podcast. At Force Management, we're focused on transforming sales organizations into elite teams. Our proven methodologies deliver programs that build company alignment and fuel repeatable revenue growth. Give your teams the ability to execute the growth strategy at the point of sale. Our strength is our experience. The proof is in our results. Let's get started.

[B]

Visit [e-mail] youm've been listening to the Audible Ready podcast. To not miss an episode, subscribe to the show in your favorite podcast podcast player. Until next time.