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Change Your Outcomes Using Problem-Centric Selling w/ Keenan {Hey Salespeople Podcast}

Episode 6 of the Hey Salespeople podcast features a lively discussion between Jeremey Donovan, SalesLoft’s VP of Sales Strategy and self-proclaimed sales nerd, and Keenan covers everything from the right approach to sales training to when to break up with a prospect.

Keenan was born selling. As Chief Antagonist at A Sales Guy Inc, he’s showing others how to find the same success in sales. In this unfiltered interview, Keenan unapologetically calls it as he sees it.

Don’t miss the segment about what is broken in our approach to sales training. It’s undeniable that most sales education focuses primarily on the close. But why aren’t we doing more training about the beginning of the sales process?  Keenan argues that the sale is won or lost at the beginning, and explains the consequences of that approach.

Keenan sales podcast

Listen to this episode for answers questions like:

  • Why should you focus on the problems vs. features?
  • How is being in sales like being a doctor?
  • Should you have different solutions based on the root cause of the problem?
  • Is it ever appropriate to fire a prospect? (Hint: You can’t fix everything.)
  • Why won’t Keenan hire a salesperson who says their motivation is money?


Partial transcription:

Jeremey:  Welcome to the Hey Salespeople Podcast, where we focus on delivering immediately actionable best practices for sales professionals. I’m your host, Jeremey Donovan from SalesLoft. Today, it’s my great pleasure to have as a guest, Keenan. Keenan, welcome to the show.

Keenan: What’s up, man? Looking forward to it.

Jeremey: Okay, you’re definitely gonna raise my energy level cuz I have boring corporate dude voice. This should be a blast.

For those who don’t know Keenan, he is the CEO of and he likes to describe himself as the Chief Antagonist of A Sales Guy. You’ll find out why pretty soon. He’s also the author of a book that I just finished reading and really thoroughly enjoyed, despite having read basically every sales book on the planet. His book is called Gap Selling, and I highly recommend it.

You can pretty much find Keenan everywhere. If you browse the pages of HBR, Forbes, MIT Sloan Management Review, Fast Company, and probably many more, I’m sure I would lose track of it. But he is all over the place. Welcome, Keenan.

I always start with a couple of questions to help people get to know you a little bit better. The first question is, what’s your favorite sales or leadership book of all time?

Keenan: Execution by Lawrence Bossidy and Ram Charan.

One of the things that’s really important to me – and depending on who you ask and when you ask, I’m really really good at it or I suck at it – but I focus on self-awareness constantly.

Really evaluating who I am – did I do a good job, did I not do a good job? I’ve done it my whole life in my relationships and work as a leader, everything. When I was younger, I realized that all of these great ideas, and I was like a little Labrador Retriever running, we can do this, we can do this, we can do it. But I had a hard time actually getting shit done.

I remember I was in a bookstore. And I was very keen on this idea that I struggled with – execution. And there was Execution. And so I got it. And it was amazing. It changed my life. Because now and I think it changed my selling as well. Because if you remember how it went down, it forces you to basically asked how to everything? How are you going to do that into my new detail? And when I started changing my mindset and looking at everything, like that’s great, but how does that get done? How are we going to do that? How’s it going to happen? It just changed my whole perspective on how to execute and how to break problems down. And I uncovered problems. And it just changed who I was as a person.

Jeremey: I remember when I read that book, I just like probably everyone, I feel like I had this great business idea once every so often, right? once a year, once every couple of years. And then you become so protective of that idea. But I think reading that book made me realize that those ideas, indeed are just a dime a dozen, right? There are so many ideas. And it truly comes down to execution in every way. Right? Not just product marketing, sales operations, everything.

Keenan: Relationships, partnerships, friendships, planning a vacation, everything.

Jeremey: Are you a big planner? Will you just go in and show up? I like to do this thing where I just basically book a flight somewhere. And I book a flight back and I just figured out in between,

Keenan: I’m in between. So no, I’m not a big planner. But at the same token, the certain things I’ve realized by being too reactive, it makes life difficult. So I’ll plan the trip. I just got back from Ecuador. Right. I planned that in December, all I did was got the flights, new the hotels, so it looked like a framework. And you were I was going and when you when I was leaving, and I knew what I wanted to see. After that I figured it all out after

Jeremey: Folks are probably chomping at the bit to know what was your favorite sales book?

Keenan: I would say it was The Challenger Sale because I am not a fan of tactical selling tips. I think they’re all stupid, right? I’m not a fan of sales books that really aren’t sales books, but they’re like productivity books within themselves and sales books.

Jeremey: It’s a repackaging of the Seven Habits of Highly Effective People into a sales format, right?

Keenan: I find most sales books to really not offer much value. A lot of people asked me for a long time, are you gonna write a sales book or you gonna do sales training? I wanted to, but I didn’t feel I had anything unique yet. I hadn’t taken all my ideas and productized them and organized them to sit down and say, ‘Okay, what do we have here?’

Until I did that, I wasn’t going to write another sales book. I am not going to do this unless I can offer something unique that isn’t out there. Now, obviously, there’s nothing that’s truly new, right? But I knew that there were a lot of things missing in social. Finally, I sat down one day and I went through all my writings. I went through everything I’ve been teaching, I got through everything I was working with my clients. It was no small effort… and I’m usually not that. I don’t work that hard.

Jeremey: I’ve written a couple of books myself. I know that writing is a blessing and a curse. Indeed, some days you are able to organize your thoughts very effectively. On those good days, it feels wonderful when you’re in a state of flow. But on the bad days, it is a pain.

Keenan: Oh, truth. So that’s why I did it. That’s why I love the challenge. So the original question. It was a sales methodology; a set of ideas based on data and facts about what sales people were actually doing. It also highlighted some things that I wasn’t paying attention to.

Jeremey: I have a love-hate relationship, I guess, as many people do, with The Challenger Sale book. One is because there is not enough tactical in there, but I can appreciate it if you don’t like the super tactical stuff. For me, the big takeaway is it’s teaching you to take control. But you mentioned Challenger a few times in Gap Selling.

One thing that you mentioned was that people who are Challenger sellers are basically extremely direct. You didn’t use the word aggressive. Do you think to be a successful Challenger seller you have to have the Keenan-style of in your face?

Keenan: No, not at all. If you listen to me on a call, I’m not really in your face. I am when I’m on social because I have to get your attention. You don’t know me, I’m not sitting across from you. I have to do something that’s going to capture and hold you.

When I’m talking to you on the phone, we’re in a meeting. I’m direct, but I’m not aggressive. You don’t need to be. I think in one of the chapters, I talked about the different types of questions. One of them is provoking questions and provoking questions as a way to challenge your question and the way you’re thinking.

Another way to do it is to just challenge them when there are inconsistencies. You don’t have to be aggressive. Let’s say you’re selling a gym membership. Someone says to you, ‘I’m 75 pounds overweight. My doctor told me I’m close to diabetes.’ Then you say, ‘Great, I can help you with training. I can help you in the gym.’ And they say, ‘I don’t know; it’s too expensive.’

You don’t have to be aggressive to say, ‘I’m confused. You said your life is terrible. You said you’re unhappy. You said you’re almost gonna have diabetes. I’m confused why you think 80 bucks a month is too expensive.’

Jeremey: Something I thought was actually one of the more novel ideas in the book, which is how to handle objections. That almost every sales trainer, or even everybody’s manager, basically says, ‘You listen, you acknowledge, you empathize, and then you ask clarifying questions.’ Once you’ve clarified, then you respond, and then check in at the end to make sure that the objection was handled. You have a bit of a different approach, but it does rely on some of those questions. Can you expand on that a little bit?

Keenan: I always say the sale is won or lost in the beginning, hands down, end of discussion. And unfortunately, most sales trainings and education focus is too far in the middle and the end. The reason being is this: if I can figure out why you’re trying to buy, the impact of the current environment on you, how it’s negatively affecting you… whatever those all those reasons are. When I get to the end, and you challenge – a particular lack of a feature or you challenge the price, your push back – I don’t have to overcome your objection. I have to get you to recognize why your objection is stupid.

I should see an objection coming. If I understand all of that stuff I just shared with you – we talked about in the book, current state, future state, and the five elements underneath them, the physical and literal, the problem, the impact, the root cause, and the emotion. If I understand that in depth, I should have gotten my ass out weeks or months ago. It allows me to qualify the value of impact that I can deliver. If I’m still in the game, I know that I can deliver for you the outcome you’re trying to get.

Therefore, when you come up with an objection, to me it means you misunderstood something. I just have to challenge you back. That’s why it’s important that you’ve explained the problem to me, not me explain it to you.

Jeremey: I think it actually is quite brilliant to actually throw their ultimate end objective back at them when they launch an objection at you. I do think that’s a super effective thing.

You just previewed a little bit of what your definition of gap selling is. Can you go into that in a little bit more depth?

Keenan: We were talking earlier about why it took me so long to write the book and why I didn’t offer sales training or anything. I didn’t want to just be another has been, didn’t want to put something out there that looks like everybody else’s. And I was looking for that hook or that trigger. I knew my stuff was different. But it’s hard, right?

It finally hit me that traditional sales training is not layered on top of the psychological way in which we make decisions. We make decisions to change. That is, at the end of the day, at the core of all sales is a desire or the thought of change.

So let’s break down. What does change mean? Change means I want to move from where I am today to a new place. And every single time we buy something – whether it’s a pack of gum in the store or it’s an enterprise ERP system for a $7 billion company – it’s still change.

If we’re going to be changing, we’d better build a sales methodology that mirrors someone’s change process, whether it’s conscious or subconscious, and the psychological elements that come with that. When you’re looking to change or looking to buy something, what’s the first thing you do? You either consciously or subconsciously evaluate where you are today. You’re like, ‘I don’t like this, this hurts, I’m tired of doing this, this sucks, it takes too long, it hurts, it’s painful.’

You start spending all this time evaluating where you are. Then somehow, some way you start comparing that to who you could be. ‘Man, it would be nice if I could get this done faster. It would be nice if I could make that happen. It would be nice if…’

All this stuff is in the future state. Between those two is a gap. The bigger the gap, the more money you’re willing to pay, the more effort you’ll put into it, the greater the impact it will have.

So I was like, ‘Well, shit, if that’s how people buy consciously or subconsciously – then we better build a selling methodology that mirrors that.’ And that’s what Gap Selling is about.

Jeremey: One of the biggest issues with even being able to do that is the ability to get people to trust you enough to share that much information with you. How do you start the sales process in order to gain that trust?

Keenan: I talk about a term called product-centric selling versus problem-centric selling. If you run a search term ‘problem-centric selling,’ I think me or A Sales Guy own the entire phrase. No one really thought about this.

When you look at your company’s sales trainings, they’re product-centric, They bring you in and they teach you about the product. I argue no, no, no!

Teach them about the problems your customers and buyers are having in their business, the ones that you actually solve. Your product only solves a handful of major business problems.

THERE’S A LOT MORE AFTER THIS! Listen to the full episode for the rest of the conversation between Jeremey and Keenan.


If you have a passion for the art and the science of sales, are looking to further your career, or just want to hear some great, practical tips, ‘Hey Salespeople’ is the podcast for you. Subscribe so you can follow along as Jeremey interviews the brightest minds in modern sales to bring you immediately actionable advice. Listen and subscribe here.

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