EPISODE 498: Become a More Vulnerable Sales Leader Thru Smart Storytelling with Mike Bosworth

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[EDITOR’S NOTE: This is a replay of the Optimal Sales Mindset virtual learning session sponsored by the Institute for Excellence in Sales on February 17, 2022. It featured an interview with sales training legend Mike Bosworth. He’s the author of multiple books including the classic Solution Selling and is now teaching storytelling for sales with StorySeekers

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MIKE’S TIP: “Find a connective listening course because we all can be better listeners and listening is really hard work. It seems like most extroverts are good storytellers but most introverts are better story listeners. If you look at the very best leaders, they’re both storytellers and story listeners. But in the sales profession, a lot more of us are better at storytelling than we are at listening. Find some coaching, some help on becoming a connective listener, not an active listener, but a connective listener.


Fred Diamond: It’s a big honor Mike to have you on the show. Mike Bosworth, you’re one of the legends of consultative selling, of B2B and enterprise sales and you’re the author of Solution Selling. You wrote that back in 1993 and was published by McGraw Hill, which is actually where I started my career.

You also wrote Customer Centric Selling in 2003. It’s an honor to have you on. You probably get tons of accolades every day from people who are familiar with the work and you really provided a lot of the framework for what our listeners, Mike, are struggling with today which is how to be effective B2B enterprise sales professionals with all of the challenges that comes with that job. Then all the challenges, of course, in the last couple of years.

First off, you look great. It’s great to see you and we’re going to be talking about something a little bit different. It’s basically how sales leaders can be more effective by connecting more effectively and intimately with their team. Great to see you, I’m excited to have you here. First question, Mike. What do young sales professionals want? What do they really want? What do they expect from their leaders?

Mike Bosworth: I think what they expect from their leaders is enough rope to be themselves and to integrate their own personality with what the leader wants them to do. Being a first-line sales manager, it’s probably one of the toughest jobs in corporate America for me and I’ve met so many people over the years that share my experience of, “I was a top sales rep, number one in the company. They moved me from LA to New Jersey and made me a sales manager and I went from hero to zero. I went from the number one salesperson to the number last first-line sales manager. “

One of the biggest issues here is that most great salespeople sell intuitively. Management promotes them because they have this vision, “God, this guy is so great. If we could have him manage eight other people, he’d train them all to sell as well as he does.” Well, how do you coach somebody else to do something that you do intuitively? That’s with great difficulty. Part of the problem is that they have to learn to codify what worked for them personally and maybe even figure out what codification other great salespeople have done too, because 80% of the people, it’s not just in sales but in all professions, aren’t so intuitive.

If you really look at the greatest people, politicians, leaders, executives, teachers, doctors, whatever, they have an intuitive ability to connect with strangers and build trust, but 80% of humanity doesn’t have that intuitive ability. My challenges with becoming a sales manager was figuring out how to codify what I did intuitively so I could teach it to other people and that wasn’t easy, and that took years. Solution Selling was the codification of the discovery process as a B2B high tech enterprise salesperson.

Even with that codification of intelligent discovery, if you will, because the learning curves are so long for salespeople who enter some of these complex product organizations that the whole idea of solution selling was, let’s harvest the brains of the best diagnostic people in our business and have them write the discovery questions for the salespeople to use face-to-face. The whole idea was if you go to a doctor for the first time, the way that doctor builds their credibility with you is asking you intelligent diagnostic questions and pretty soon you go, “Oh, wow, this doctor is pretty smart.”

That was the whole idea with salespeople but what I missed, Fred, when I wrote Solution Selling was that the vast majority of human beings have what I call discovery resistance against salespeople. They can go to a lawyer for the first time, a doctor for the first time, they’ll start asking discovery questions, they’re fine. But on a first encounter with a salesperson, if that salesperson starts asking discovery questions before that buyer has connected and decided to trust that salesperson, it goes south.

I’ve had 20 Vice Presidents of Sales over the years share with me that the top 20% of their salespeople loved Solution Selling and reached a new plateau of performance because they weren’t selling vaporware anymore. They were actually in intelligent discovery. But the bottom 80% quit using it within two weeks of the workshop because – it took me a long time to figure this out – they did not have the intuitive ability to go in and meet a stranger, connect emotionally and build trust intuitively, so they took out their discovery questions prematurely.

They were good questions written by the smartest people in the company but the buyers would go, “Whoa, I don’t trust you enough to answer those questions. I don’t know you well enough to answer those questions.” My latest endeavor using the power of story was to teach the 80% of salespeople who don’t connect intuitively how to use pure curiosity and what we call a customer hero story. If I was sitting next to you on a plane, Fred and I said, “Fred, what do you do?” How would you answer me?

Fred Diamond: Well, I would probably say I run an organization for sales leaders helping them attract, retain, motivate and elevate top tier sales talent.

Mike Bosworth: If I said back to you, said, “Oh, so you’ve got an organization for sales leaders? Can I share a story with you about another guy I know who runs an organization for sales leaders?” What would you say?

Fred Diamond: I’d be very interested in hearing that story.

Mike Bosworth: Pure curiosity. In other words, with a stranger, in 10 seconds you can ask them if they’re curious about their peer. If they say yes, which 99.9% of the time they do, now they have granted you 60 seconds of story time. Now I can tell a stranger a 60-second story that has a setting, has a struggle, a before-they-had-my-product struggle, his or her vision of what they needed to do to solve their problem and 18 months ago they bought our products and today the results are A, B and C. But enough about me, Fred, what’s going on with you? That 60-second story converts the pure curiosity to pure envy.

Fred Diamond: I’m going to ask you a question. We’re going to get to that, but I want to go back to where sales leaders struggle, and specifically where they struggle with the people that report to them. You and I were talking before about how when you observe that sales leaders are struggling, the hardest job is a first-time sales leader for a bunch of reasons we talked about, but when you see that they’re struggling, you have said that it’s frequently because they’re oblivious to the emotional responses of the people to their behavior. We’re going to get to how storytelling can make them more effective but talk a little bit about that. Talk a little bit about why that is.

Mike Bosworth: What great salespeople have is the ability to influence people they have no authority over to take action. That’s why they’re great salespeople. But when you become a manager, now your company gives you authority. This whole authority thing is a killer especially of new managers. Then on top of that, the only thing my management could define for me as a new sales manager is, “Mike, you got to get their expenses in, you got to audit them. You’ve got to make sure they’re making so many calls, so many demos.” They’re giving me all these rules they want me to enforce.

Most salespeople are free spirits anyway, they don’t like rule enforcers. If the first-line rookie manager who knows nothing more than ‘here’s a list of rules to enforce’, it’s not a way to gain trust and connection. One, we need a way for managers to gain trust and connection. The typical best way is vulnerability. We teach a leader or a salesperson – basically, if you’re in sales or if you’re in leadership, if you really want to emotionally connect with that other human being, you’ve got to be vulnerable first.”

Fred Diamond: It’s interesting, we’ve spoken a lot over the years about vulnerability and of course over the last couple of years authenticity and transparency, things like that but it’s really hard. We do a show every Tuesday for Women in Sales, men versus women. A lot of the women that we’ve been working with, women leaders, they’ve embraced the vulnerability. They’ve embraced the transparency and the authenticity.

A lot of male sales leaders who especially are brand new, they feel good, they got recognized, they had this promotion, if you will. Especially if they’re working with a high charging type of a team, it’s a challenge to be vulnerable. I like what you said there, you need to admit maybe even publicly that you’re deficient in certain of those things.

Mike Bosworth: If I were a rookie manager now or if I knew one, I’d coach him to get in front of your team and say, “You know what? This is all new to me and I’m not sure really the best way for me to manage each of you, you’re all individuals and I’m struggling here with how we go about this.” There’s the human relationship part of it but the other part of it is, does that company have a sales process that honors the buyer, that’s authentic, that isn’t pushy, that isn’t high pressure?

In a lot of cases, if you join a company with a high-pressure culture, you’re screwed. Over the years, I think Oracle has just… the whole thing is high pressure from top to bottom and it’s a horrible place to work. They hire new people and they don’t groom them and 30 or 90 days later, if they haven’t sold anything, they fire them. There’s really toxic cultures too. Two things for sales manager success, one is how they become vulnerable and authentic with their people and earn their trust. Then the second thing is, is do they have a non-toxic defined sales process for honoring the buying cycle of their prospects and not being pushy to their prospects?

Fred Diamond: Talk about that for a second. When people say to me, what’s the first thing I’d recommend to them? I say, know everything about your customers industries. Really focus on a vertical. Know all the challenges that are moving on, if you will. I’d like to have your insights. Again, you’ve written some of the most classic books in sales

Mike Bosworth: I think it’s a little more complicated than it has to be. Around your product, how do your happy customers use your product to make money, save money, solve problems, achieve goals? That’s the critical knowledge for all salespeople. In Corporate America today in the high tech industry, they hire a new salesperson and who do they have train that new salesperson? Product marketing. Product marketing is teaching features, advantages and benefits and demos and stuff like that, and product marketing is product expertise. What salespeople need is customer expertise. They need customer user expertise. How are our best, smartest, most successful customers using our stuff to do better in their jobs?

Fred Diamond: Let’s get back to the managers here. Let’s say that we educate the managers that they need to be vulnerable, they need to be transparent, and they need to let their leads know, here’s where I am and here’s what we’re going to be working on. How do they then shift? You talk about the concept of connective listening. Talk a little bit about how you become a didactic manager, for example, to a connected leader by connective listening?

Mike Bosworth: Well, connective listening is really difficult. I don’t know if you saw that paper John Kratz and I recently published. One of the Big Four consulting firms did a survey of like 3,600 American managers and executives and 97% of them graded themselves as great listeners. That’s completely crazy. It’s delusions of listening competence. The first step in getting better at anything is to admit that you aren’t that good in the first place.

I think the first step in becoming a better listener is to get some feedback from the people around you. Typically, the people who love you the most will give you the best feedback about how good a listener you are or you aren’t. The difference between active listening and connective listening is emotion and feelings. Active listening, I can play it back. You got this many of this, you started in 1984, all the facts, boom, boom, boom. That’s active listening.

But connective listening is Fred, you told me when you changed from this company to that company for this first two months you couldn’t get out of bed? I said, “What was that like?” In other words you’re peeling the emotions behind the facts. That takes practice and expert coaching feedback. There’s no way you can learn connective listening from a book or a video.

Fred Diamond: Interesting. What’s the role of the company with the sales leader? A lot of times and you might have even mentioned this before, we’re thrown to the wolves, right? A company says, “Gee, this guy is really great. You should be managing eight people to get them to the level of where you were.” We talked about some of the challenges. What are some of your recommendations?

Then I want to get to storytelling. I don’t want to miss the opportunity because you’ve written so many amazing things and of course, you founded Story Seekers to teach sales professionals how to build their inspirational connective leadership skills through story. We talk about storytelling a lot but I want to get your insights. Last question before we move into that is what is the company’s responsibility? We have a lot of senior sales leaders who listen to the Sales Game Changers podcast who are members of the Institute. What are your recommendations for them to help this first line manager really become effective?

Mike Bosworth: Well, I think most senior sales leaders, vice presidents of sales, CROs, Chief Revenue Officers, they’re former star salespeople who made it through their first sales manager job, because a lot of them don’t. But if you go back and look at how did they really get through their first sales manager job, they realize that they didn’t understand their own process well enough to teach it, so they had their eight salespeople go out and shake trees and anything that looked like a live one, “Call me in, then I’ll go in.” They’d go in and help them close it.

It became the eight tree shakers and the chief closer. That’s how they survived their first sales manager job, but they make their nut. Then if you make your nut as a sales manager, you get promoted again. But boy, that first one is lethal because didactic people don’t want to work for somebody they don’t trust.

Fred Diamond: Let’s move into storytelling for the remaining part of today’s podcast. We’ve had some storytelling as topics and a lot of times people will ask me another thing that I recommend, and I always say, have a pocketful of stories. Have a pocketful of 30-second, one-minute stories. Because something like what you just said, you meet somebody for the first time and then you don’t go into a 10-minute story but something that’s appropriate and valid.

Give us some of your insights. Again, you’ve made the shift, you provided so much value in that side, give us some insights into how the sales leaders and the sales professionals listening today should be thinking from a story perspective. A lot of times, the junior ones say, “Well, I don’t know, I just started up. I don’t even know what to say to begin with.” Give us some of your insights Mike Bosworth.

Mike Bosworth: Well, as a salesperson, the three types of stories you need are your company story and why you joined them. Your personal story of how you ended up being here in 2022 carrying a bag for the ABC Company. In other words, your personal story of your career growth. “Back in college, I thought I wanted to be this and then I went this way and then this way.” There’s one each of those two stories but the third category are what we call customer hero stories.

You might have dozens of customer hero stories by buyer persona, by industry, whether you’re insurance or manufacturing, or medical, and what job title. You’d have the different customer hero story for an IT person than you would for an HR manager, or a CFO, or whatever. The customer hero stories are the way young salespeople gain credibility with older buyers. I’ll tell you, my personal experience from Xerox put me into sales at the age of 28. Luckily for me, I’d been on the support side for two and a half years.

I did it intuitively, took me years to figure out how to teach it but I’d go into a manufacturing company and say, “Hey, I’m Mike Bosworth with Xerox Computer Services, I’d like to speak to your materials manager.” Eighty percent of the time they come up because they’re curious but they’re 48, 50 years old, I’m 28. Invariably, when they’d walk up to see me in the lobby, they’d look at their watch, which is telling me that “I’m going to be polite to you, but we’re going to end this quickly.”

But I confirm the job title, you’re a materials manager, you say yes and I say, can I share a quick story with you about another materials manager less than a mile from here that I’ve been working with for the last 18 months? I never, ever had a rejection to that offer of a story. Now the key is, no matter how good your story is, if you’re a stranger, you can’t go up and start telling a stranger a story. You have to get permission to tell that story. In 10 seconds, can I share a story of one of your peers? Once they say yes, now they’ve granted you 60 seconds.

The thing about stories is we raise our kids on stories. My grandkids, boy, if I say, you want grandpa to read you a story? They’re all over it, they’re in my lap, they’re ready to go. They’ve actually put people in MRI machines where they would introduce the idea of anticipating a story. When a human being anticipates a story, the critical left brain shuts down, the right brain, the channel of all of the five senses and the feelings and everything opens up. That anticipation. It’s not only important to get permission to tell a story, but their permission triggers that human anticipation for a story. It provides just a perfect place for you if you can pack into your message in the form of a story, 60 seconds, enough about me, what’s going on with you?

Fred Diamond: Mike, I want to follow up something which you just said and this has been a cause for contemplation. Typically, if you’re in sales, you’re most likely selling to someone who’s older than you especially if you’re in your first or second job, if you will. If you’re an SDR, if you’re even the first level of account executive. Because people who’ve reached the decision-making ability have had a 15, 20, 30 year career and the people who are DC level people, they’re probably going to be 20, 30 years old than you.

Again, we’re doing today’s show in February of 2022, probably going to be in their late 40s, 50s, some cases 60s. You have to talk to them a certain way. That’s a great observation which you just made there. You got to provide something that’s going to be valid to them, not just the value, but valid to them about where they are in their career.

Mike Bosworth: At the end of that 60 second story, I want my suspect to come to a couple emotional conclusions, not logical conclusions, but emotional conclusions. The first emotional conclusion is, “Oh, yeah, this guy looks really young but boy, it sounds like he understands how hard my job is and it seems like he has helped one of my peers solve my biggest problem which I haven’t been able to solve yet, and so I’m interested in learning more.”

Fred Diamond: That is a brilliant point. One thing we tell people all the time is your customer is not looking to jump places for the most part. They’re probably going to be there, especially if you sell into industries like government or education, they don’t want to leave. Yeah, they want to have a career ascension. I like what you just said, you show me that you understand what’s really emotionally important to me right now.

Mike Bosworth: The best way for me to do that is to tell you a story about one of your peers that I’ve already worked with because I’ve learned from your peer how hard your job is.

Fred Diamond: Mike, we have a couple questions here that are coming in. I want to get to them before we ask you for your final action suggestion. We got a question here from Gerry. Gerry says, “How do I build more trust with my team? I’m trying to be vulnerable but I don’t think I’m coming across that way as much as I would like to.” It’s a long question but thanks, Gerry. Talk about that for a second.

Mike Bosworth: I’ll tell you a quick story for Gerry that a sales manager I was coaching on accidentally discovered how important being vulnerable was. He had a salesman who’d been failing for about 90 days and he had the three o’clock in the afternoon on Friday come to Jesus meeting scheduled. Somehow right before he started the talk with his employee, he personally said, “I’m sorry, I just got off the phone with my kids’ school ad I’ve got a kid with ADHD and he is struggling in school and it’s really making me sad, I’m not sure what to do.”

The salesperson who’s not making it came back and said, “Well, you know, the primary reason I’ve been failing for the last 90 days is I’m having a problem with my kid too.” There’s emotional issues and stuff like that. Just the fact that the manager shared, “I’m struggling with one of my kids,” allowed the seller to open up with the real reason he’d been performing so badly. Most salespeople don’t trust their manager enough to share the real reasons.

Fred Diamond: That’s actually a great point. Someone sent me an email this morning where he’s using the expression, EGS, everyone’s got stuff. Especially over the last two years, and I know prior to this call you and I were trading some stories of things that we’re both going with. We got time for one more question and then your action step. Let’s just take Stephanie’s question. This is a request.

She says, “Thanks Fred, thanks Mike. Can Mike tell us his best story of all time?” I’ll put you on the spot there, Mike, before you give us your final action step. You’ve had so many experiences in your career. Again, the book Solution Selling is one of the bibles for a long time of enterprise corporate B2B sales, complex sales. Do you have one go-to story that will send our listeners off on an up note and then we’ll get your final action step?

Mike Bosworth: You know, I really don’t. I would say to Stephanie, come out to Orcas Island and we’ll have a glass of wine. In an hour I can tell you a couple of those stories but there aren’t any quick stories that are the best of all time. I know that we have a finite amount of time here. I love to tell stories but that’s a request I can’t really grant well in the short amount of time.

Fred Diamond: Got you. We put you on the step there. Stephanie actually says, “That’s no problem. I’ve been to Seattle.” I guess maybe she knows where you are. Mike, I’ve genuflected a couple of times today on today’s show, but I just want to acknowledge you for the impact you’ve had on tens of thousands if not hundreds of thousands of maybe even millions of sales professionals, helping them take their career to the next level with Solution Selling and Customer Centric Selling and all the great work you’ve done. Now over last decade or so with Story Seekers, and really focusing on storytelling, which you’ve given us a little bit of a taste of today, so good for you and for all the lives you’ve impacted. Give us your final action step. You’ve given us so many great ideas, but give us one specific thing that you think people should do right now to take their sales career to the next level.

Mike Bosworth: Well, it would be to find a connective listening course because we all can be better listeners and listening is really hard work. It seems like most extroverts are good storytellers but most introverts are better story listeners. My wife’s a therapist, not a storyteller, but boy, she can peel the emotional onion of any human being. If you look at the very best leaders, they’re both storytellers and story listeners. But in the sales profession, a lot more of us are better at storytelling than we aren’t listening. The advice would be, find some coaching, some help on becoming a connective listener, not an active listener, but a connective listener.

Fred Diamond: Very powerful. Once again, thanks everybody for listening today and thanks to the great Mike Bosworth for sharing your insights. My name is Fred Diamond and this is the Sales Game Changers podcast.

Transcribed by Mariana Badillo

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