Share Post:
Return to Blog
josh braun sales
December 12, 2021

Sales Leader Interview: Improving the Sales Process with Empathy and Milkshakes

josh braun sales

Is there any place for empathy in sales? How can we improve our sales process by understanding the buying process?

These questions were at the core of my conversation with Josh Braun, founder of SalesDNA, someone who, if you work in sales and spend any time on LinkedIn you will have heard of.

Josh and I brokedown what it means to truly understand how buyers buy, and what this can do to your sales skills. We dove into understanding why prospects buy, and why they don’t buy.

We also discussed:

  • Why old fashioned approaches to sales persist
  • How salespeople can reduce the tendency to use those approaches
  • Practical tips for using LinkedIn to develop your own authentic voice
  • Why Josh agreed to coach an 11-year-old to make cold calls
  • What the real job of a milkshake at breakfast is

Here’s a transcript of our conversation.

Rich: Welcome Josh! I think one of the things that I admire about what you’re doing on LinkedIn in particular with the content you put out is empathy. And I think that’s something I want to spend a bit of time in this conversation talking about. So yeah, just wanted to say straight off the bat. I think empathy seems to be such a big part of what you do. And if people are listening to this and they don’t think sales should involve any kind of empathy, then wrong podcast, pause or delete the podcast straight away. From your perspective that’s something that’s important to you.

Josh: Yeah. I think when we talk a little bit about outbound, one of the big mistakes that I often see people doing is creating messages that are what I call hype-y. So they typically will include, we’re increasing conversion rates by 67% or we’re 10Xing your revenue, or we can give you abs in six minutes. And these hype messages come across to people like a stereotypical salesperson. So they really tune you out. So the way out of hype is really through three different mechanisms. One of them is the one that you alluded to earlier, which is empathy. And specifically what I mean by that is you being able to describe your prospect’s struggles or desires better than they can using their language so that when they read it, it’s almost as if, as Robert Collier said, is a famous copywriter, you’re joining the conversation in their mind.

And when people feel like you really get them truly and you’re speaking their language, specifically their words, they’re more open to listening to what you have to say. So that is one of the three ways in which you can break through empathy is at the core of prospecting.

Rich: And one of the things, and we’ll come on to the other two. I’m keen to do that, but just in case there are maybe one or two people in the world who don’t know who you are. Give people a little bit of background. Who are you? What do you do? What are you involved in day to day when it comes to sales coaching?

Josh: Are you telling me there are people that don’t know who I am? This is news to me. I can’t even imagine. So my name is Josh Braun and I am a person in the United States in Florida who started out as a school teacher and also worked at Nickelodeon. So my roots are in education and entertainment and I combined both of those things to help sales teams start more conversations with people they want to get in front of, but in a way that doesn’t feel salesy, manipulative or gross.

Rich: So I do want to come back to those two other pillars, but this is something that really resonates for me. I’m not a salesperson, I’m in marketing, so I guess I’m in sales of sorts, but I’m a marketer by background and one of the things I think that people often are concerned about, alienated by, pissed off about, is that kind of old school cheesy, salesy mentality. Why does that still persist? Why is there these overhyped approaches, using these old outdated methods that I as, and I speak as one myself, completely turned off by. Why do those old stereotypes still persist?

Josh: Yeah, it’s a great question. And when I asked the question in my workshops, how did you learn how to sell? What I typically get is, I read some sales books, I learned through a sales mentor or I just did it by trial or fire. But what I never hear or very rarely hear is that I learned how to sell by focusing on why people buy and why they don’t buy. And I think that’s the fundamental disconnect is that we’re all taught a sales process, which is oftentimes very disconnected from a buying process. And when you focus on the buying process, it turns out it’s a completely different perspective.

And when you focus on the buying process, you don’t come across as a shady salesperson. The other big thing that I see that’s super critical and the reason why people are kind of coming across as stereotypical sales people is intent. And let me just explain a little bit what I mean by that. When you start a sale or a conversation or when you wake up in the morning and your intent is to book a meeting or to get a sale, prospects can feel that versus an intent that’s a servant intent. Meaning, I’m here to not assume that what I have is what someone wants. I’m here to present A idea to help them potentially, do something better or to see if they have a struggle that I could potentially help them with.

So coming in with an intent that doesn’t assume, and that doesn’t think that everyone I speak to needs what I have when I call, is a fundamental shift, but once you make it, prospects can actually feel that. When you come in with that assumptive energy and that and the energy to book a meeting and close a sale, prospects feel that, and they often retreat and repel.

Rich: And I speak as a buyer and I completely endorse that, 100% I can detect it almost instantly. That lack of empathy, that lack of interest, this focus on the buyer is one of a number that needs to be achieved in order to get the result. I can absolutely resonate with that. Yeah, that’s something that as a buyer, I just wish people would move on from, but as I said, it just persists. And obviously for many of the reasons that you’ve outlined there. Let’s take it in a practical direction then, we’ve talked about empathy as a way to reduce that level of hype, those alerts or those warnings that as a buyer, I’m very aware of. What are some of those other things? You mentioned two other pillars essentially that help reduces that overly hype sales approach. What can people do to reduce that?

Josh: Yeah, sure. So we talked a little bit about what you think. This is intent. The next piece is what you know about your market. And so a lot of people will not spend a lot of time on this. They’ll jump into cold email templates and cold email scripts and they’ll use marketing language that often sounds very hyped and generic.

People are very averse to these claims that seem really inflated and unrealistic because everyone’s throwing percentages around. And it turns out that when you actually talk to customers that bought and you use a framework called Jobs-to-be-Done, which we can get into, which is a framework that allows you to understand specifically why people bought. No one woke up one day and decided to buy your software. A lot of things happened before they started shopping and then maybe they decided, I shopped and I just don’t want to do anything right now.

Then some other things happened and then they eventually decided that enough dominoes tipped over that they were going to risk their job in their career and their reputation at work to buy your software. Those words and those journeys that they use, that language can be used from a prospecting perspective that often allows you to be more empathetic with your buyer and not have you come across as a stereotypical salesperson. So this idea of knowing your buyer.

The second way to differentiate yourself and get out of this trap is to demonstrate that you have a point of view. It’s what I’m doing right now on this podcast. It’s what I do on all my posts. So being able to demonstrate that you have a point of view about a topic that might be of interest to your prospects is going to differentiate yourself. Because instead of you talking about how great you are, you actually are showing them through your content or through your perspective on a topic. And then the final way is through your customer’s words. If I were to tell you that I’m the best sales coach out there, it wouldn’t really give any meaning. It wouldn’t be credible because I’m saying it. And of course, I’m going to say it because I’m biased. I have an ulterior motive to get your money, but your customers don’t. Your customers are better salespeople than you are.

So you’ll notice a lot of the things in my posts and on my site are the actual customers doing the bragging. And you can actually use your customer’s language that you had from your interviews in your cold email copy and in your sales message. So again, just to summarize this idea of empathy, getting to know your prospects, motivators, and struggles better than they do. The second piece shows your unique point of view. Third, getting to know your market really well and then the fourth and final one, using your customers as your salespeople through their language and testimonials.

Rich: Let’s focus on the opinion part of this because this is very relevant for me today. New SDR joining Allego, giving her an overview of the marketing work that we do, onboarding her into the business as part of her induction. She has low double digits in terms of LinkedIn connections, brand new to a business. How can you take somebody who’s so green in that regard and start to get them thinking about what they’re putting out there on platforms like LinkedIn? What are some of those early steps? Somebody who’s quite new to the business can do to start to generate some traction?

Josh: Yeah. Sure. The great news is nobody’s listening so it doesn’t really Richer. If you’re afraid, like Oh my God, I’m going to write something and it’s going to be terrible. So the idea here is that you have to create content based on what your audience is going to care about. So you have to have a little bit of a perspective on how you guys see the world. I mean, Richard over here at your shop does this really well. He has a definite perspective on how he used a world. Your SDRs should learn a little bit about the space and should form their own opinion about how they see it and communicate it in a way that’s going to be entertaining. And we’ll get into this a little bit later on, but just presenting information is not going to be enough. Because the domain expertise, you’ve probably been to college and seen people lecturing that are professors that have the domain expertise, but they’re boring and they put you to sleep.

So you have to have a point of view that’s a little bit different. And you have to present it in a way that’s a little bit entertaining. So that people will be like, “Who is that person?” And that’s an interesting point of view. And they’re presenting it in a way that’s a little different. That’s kind of like the idea behind the I Teach My Wife Sales piece, which I know we’ll get into, I could present that same information and a lot of different ways. But I chose to involve my wife in the presentation of that content for sheer entertainment purposes because I know how important it is.

Rich: Yeah, we’re going to get into that. And that reminds me as well we at Allego put out a video a couple of months ago of our CEO son Joe doing some cold calling. And we did a follow-up video to that last week, you were very generous in your time helping coach Joe, but in a sense, that’s what we’re doing as well. We’re saying, coaching is a craft, it can be taught, you can transfer those skills and knowledge to somebody, even if they’re 11 years old and completely green if they have a willingness to learn. So that’s our position in a sense for that video. We’re putting ourselves out there, we’re staking. We’re staking a claim, we’re putting a flag in the ground and saying this is what we stand for. And I guess that’s really what you’re saying is take a position, whatever it is, take a position and hopefully, it’s one that will resonate with your market.

Josh: Yeah. The Joe example is a fantastic example in a couple of ways. First, it’s a point of view. And second, it’s a little different, it’s an 11-year-old presenting it. And third, it’s presented in a way that’s entertaining. So if you’re a new SDR, just getting started, you might want to just flex the muscle by just talking about your experiences as new STR. This new SDR is selling to salespeople. So it doesn’t have to be anything related to Allego, it could be … One of my experiences is when I’m bumping into learning the SDR role and it could just be a two-minute video of him or her talking about their experiences and not just the fun glowy positive stuff, but also the negative stuff because when you share that you’re vulnerable a little bit, people connect with you. And when people connect with you, and they see that you’re a little charming, they’ll want more of you. So just reflex the muscle, just post stuff about what’s happening in your daily day, over Allego to get started.

Rich: Let’s have a quick chat about this coaching an 11-year-old, you were very generous last week. I think we all thought that this was going to be a mock cold call that Joe would call you, and you would perhaps give some feedback at the end. It ended up as close to an hour of coaching but we’ve recorded and I have the joyful task of editing that into a format that will makes sense, but it was fantastic input from you. Why did you volunteer to coach an 11-year-old how to cold call?

Josh: Well, I mean, it’s fantastic. I mean, you have someone who can be choosing to spend his time as an 11-year-old. I don’t know about you, but when I was 11, the last thing that I was thinking about doing with anything related to work, was up outside or playing Super Mario Brothers. So it became apparent very quickly that he was very interested. In addition to being a normal 11-year-old boy doing all sorts of interesting things outside of work. He was really curious about learning how to be a salesperson, maybe in part because he’s a learner. And so I really like volunteering my time with people that are invested in their own learning.

I mean, a lot of people I speak with, when I asked them, what’s your learning plan? What are you doing to improve your skills? Oftentimes, they don’t get an answer. We’re living in a time now where you don’t have to wait for someone to teach you anything. If you don’t have a great manager, you don’t have a great mentor, great, you can go on the internet, you can learn stuff on your own, you could read tons of books, listen to this podcast or do what Joe did, which is say I’m going to reach out to some people on LinkedIn, to see if I can get their perspective on something. And I think you’ll find that most people will give you their time.

And Joe really demonstrated to me the three magic things that you need to be able to improve your skills. One of them is information. So this is him learning, what a cold call is in the scripts. The other one, which is super important is doing something with that information, which is actually making the effing phone calls. So he actually picked up the phone and made the dials. And then the third piece, which is really key is reaching out to mentors that have done it for a while and synthesizing whether or not you want to take their advice into your mix. So that’s a very powerful way to improve.

Again, information doing and mentors, and because he’s doing all three of those things, and he’s also pretty charming and likable, I have no problem spending time with him. It would be happy to do it again.

Rich: So we’ve got the video, that’s going to be out by the time this podcast goes live, so I hope people will be able to check that out for themselves. I think I have an interesting or I have a question I think I’m interested to get your response to you. And that’s what did you actually take away from the experience of coaching Joe? Because I think sometimes we see coaching and I’ve interviewed so many coaches for this podcast, is almost like a one-way dialogue, yes this and two way, but it’s largely a one way. What do you as a coach take away from that experience? So maybe coaching more broadly, but specifically about that experience with Joe?

Josh: Yeah, so I took away one major thing. And the major thing that I took away with Joe is that he has a strong desire to improve and learn. And you can see that as evidenced by certainly our conversation, but also the drilling and the practicing that he’s been doing internally at Allego, it’s interesting like in sales. If you want to get better at pretty much anything, you have to practice and try stuff. But in sales, we often don’t do that. And I really admired his ability to be able to practice his skills with me and internally with Allego.

I do this thing at one of my workshops where I’ll hold up on math multiplication cards, and I’ll have people shout out the answer, six times five, 30, five times five, 25. Send me some information deer in the headlights. And why is that? Because we know these things are coming. And so Joe, which was great, we did some objection stuff and I threw some curveballs out of him, and if you didn’t know it, he kind of made note of it. We did some coaching around it but his strong desire to practice, off the court is going to make him so much better when he gets on the court.

Rich: Yeah, I was watching him for pretty much the whole day. We spend a lot of time outside of your conversation, a lot of time. And that’s the thing that impressed me is just the relentless desire to keep practicing. Yes, a little bit of frustration, but also able to manage that frustration, and recognize that it’s an inevitable part of the practice. That was what impressed me the most, and he just was absolutely relentless all day.

Josh: You make a great point, it’s like when you learn how to snowboard down a mountain, it’s going to suck, for a long time, it’s a steep learning curve. And I have the saying, just embrace the suck. It’s like, if you learn anything new, it might hurt your ego a little bit. You got put up. And that’s the other thing I’ll mentioned about Joe. There was no ego. There’s no ego with Joe. And a lot of times people are afraid to be vulnerable, and have their calls recorded and have their calls critiqued, because it can be hurtful. And people don’t like to feel bad, and they want to feel like what they’re doing is not the best. And so this idea of embracing the suck and appreciating it, and letting go of the ego, I think are also a couple of great attributes that he has.

Rich: It’s inevitable on a podcast like this, that we have a sports analogy. It’s just inevitable. We have to go there. So I think now is the right moment to introduce the sports analogy into the conversation. Josh, I know you are currently training for triathlon or Iron Man, what has doing the triathlon taught you about yourself in a way that could be applied to sales?

Josh: Man, there’s so many things, but I’ll talk about just one thing just to focus the conversation a little bit, we kind of touched on it. I think the thing that separates the great sales people that I know and actually the most successful people that I know outside of sales is really one thing. And that is this idea of being consistent and doing the mundane things over and over and over and over and over again. I use another analogy that is not a sports analogy, which is like, 401K plan. You can contribute $100 here, $100 there, you won’t really see any gains. But if you are consistent, and you do it every year every week and you don’t watch the market, going up and down, and after 15 or 20 years, you’ll have a really nice nest egg.

It’s the same thing with sales, oftentimes, people will say, “Hey, I made 20 calls”. But then they’ll skip three days and … you don’t ever get into a groove. And with training for triathlon it’s the same thing. There’s a lot of days where I wake up, and I don’t want to get in a pool at five o’clock in the morning. But I know if I skip a day, that it tells my brain, “You know what, I skipped the day and then maybe I could skip two days or skip three days”. And so this idea of making sure that even if you’re not in the mood for it, that you do it consistently.

And one of the tricks that I discovered to help me be more consistent is creating these habits for myself that were easy. So with the triathlon in the morning, if I have to run at 5:00 AM, I will have my shoes with the socks in the shoes, and the shorts laid out so that when I get out of bed, I literally step into the shoes. The way that translates into cold calling is before you leave work, I like to ask my team, do you have 60 people to call the following day and can I see that list. And when I see that list, I don’t mean hunting and pecking around in the CRM or looking around on LinkedIn, I mean, a fixed and finite list. I don’t care if it’s a spreadsheet, if it’s written on a notepad or if it’s in a CRM, but this idea of prepping so that you build the habit every day.

Rich: I’m just trying to imagine what sales coaching looks like with your team, with you there. I can’t even picture the scene. Give us a sense of what Josh Braun and his team, what coaching looks like for you guys.

Josh: Yes, so I’m a little bit different in one way. It’s a little controversial, and I kind of understand both sides of it. There was one side as a coach doesn’t necessarily have to be the one to do the work. Phil Jackson is not as good of a basketball player as Michael Jordan, but he’s a great coach. But I feel like especially with younger people, that in order to develop credibility, I actually do the work. I can’t expect them to make a cold call and have conversations and practices, intense stuff, the fusing objections things that I teach, if I’m not doing it myself, so I will teach through example. It’s kind of like how this guy, God, I can’t remember his name but this guy used to be on PBS. Used to show people how to paint. Bob something, it’s escaped-

Rich: Isn’t it Bob. Yeah. It’s Bob. I remember even in the UK, I think we got that. We got a massive haircut.

Josh: Yeah. He didn’t tell you how to paint. He actually showed you how to paint. And I think it’s a really great mechanism for learning, which is actually doing and you would pick up your brush and you would kind of do what he did. I have roots in education. That was certainly something that they taught us when we were becoming teachers called scaffold instruction, where you model it first, and then you gradually take away the control to allow the people to do it independently. That accomplishes another great thing which is it gives you as a new SDR manager if you’re coming in new.

I’m a tremendous amount of credibility. Because if you can get in there and strap in and start making calls and you’re going through the same rejection they’re going through, but you’re keeping a positive mindset. You’re organized, you’re making the dials, that’s going to go a long way toward them believing in you and following your lead.

Rich: So you’re giving them a model, that something like a model. It’s a person and behavior that they can model.

Josh: Totally, I’m going in, and I’m actually doing it. If we were to work together at Allego with your team, I would literally be making the calls and people would listen to me making the calls. We talk about tonality. I actually model in addition to writing the scripts and all the playbooks and everything, we actually go ahead and do the work and model and learn together because one of the things that I tell people is, this is not going to be all roses at the beginning. I don’t have any magic fairy dust that’s going to turn every connect into a meeting. We’re going to learn a lot of stuff together and I’m not going to reprimand you. You’re already setting meetings. I’m just going to teach you how to set more of them.

Rich: I love that. Love that. So you’re coaching teams, you’ve alluded to it, you’re coming into businesses, you’re coaching the teams. What’s sort of businesses do you typically work with or is there no typical? Is it just really, whoever expresses an interest in working with you?

Josh: Yeah. These are typically teams that have SDRs, I don’t know, anywhere from four to 10, 12, SDRs, and they’re doing well, they’re doing fine. They’re booking anywhere from seven to eight meetings, maybe a month at the enterprise level. And they are looking to do more of that. So they’ll bring me in, to be able to teach them some new ideas and strategies that maybe they haven’t thought of before, to accelerate primarily the number of sales qualified meetings that they book in the course of a month, but doing it in a way that’s actually not going to burn people out. And then the second scenario is usually in a time of change, where perhaps a manager is transitioning out and they need somebody to come in to ease the transition into a new leader.

Rich: When you go into businesses, what are some of the things that are red flags to you in terms of a business that claims that they want to do coaching. But perhaps you start to get little bit uneasy that maybe this isn’t going to be a sustainable thing? Are there any sort of red flags for you that a business might not be ready for external sales coaching?

Josh: Yeah, one of them, I guess you can call it red flags is that they don’t have a culture of coaching. And so I’ll explain you what I mean by that. Oftentimes, I see organizations that are really great at creating these awesome salesforce dashboards. And they have metrics upon metrics upon metrics, of dashboards and reports and all kinds of stuff like 12 widgets, like 14 widgets, hit the next page, see some more widgets. But the metrics are like a means to an end. The metrics are only supposed to be used to improve rep performance. I can’t say to somebody, I have a triathlon coach, and he can’t say to me, Josh, I need you to really run a little faster. I’m like, I don’t know how to do that.

What are the drills with tempo drills? What are the exercises that I need to do to be able to run faster? And what I see oftentimes in some sales organizations is that people kind of hide behind these reports. And they don’t necessarily spend the time on coaching. I think there are a couple reasons for that. I mean, just because you know sales doesn’t necessarily mean you can coach sales. I mean, I’ve hired guitar teachers plenty of times in my life that are awesome guitar teachers, but not good coaches. And teaching and coaching are separate skills.

I mean, I happen to have gone to school, to be a teacher and an educator. But coaching is not just an inherent thing that you have, because someone says you’re a coach. You have to learn how to coach just like you have to learn how to explain things. And just like you have to learn how to teach and again, getting back to that example of the college professors, they know their domain, but man, a lot of them can’t teach because you just fall asleep in the classroom.

Rich: I shared a post on LinkedIn the other day about, I have a coach. I’ve just started to get into shooting, it’s something that I’m very passionate about. And it’s something that I really enjoy. And my coach is very much a coach. He can teach, but he’s also able to do it in such a way that it’s highly responsive to my individual needs. He can model, he can produce results, I can model those results, but ultimately he knows what I need to take it to the next level. He knows what I need to improve my performance. Is that what you’re kind of alluding to with the difference between a coach and a teacher? It’s someone who has the flexibility and the adaptability to take the person in front of them, see what adjustments are required, help them implement those, and then allow them to realize the success?

Josh: So I’ll give you an example. And this rather than just talking about giving an example. So I as you mentioned doing triathlons, and I’m trying to get more efficient in the water. So swimming isn’t just about moving your arms real fast. If you do that, you can certainly go faster, but you have at the expense of getting tired.

So as a beginner swimmer, oftentimes we move our arms really fast, because we don’t have the technique. If you learn how to do the technique, then you can work a little less and go further faster without exerting the energy. So I hired a swim coach, obviously a gifted swimmer, but also a great coach. And he looked at me, and he said, we’re going to just do one thing for a while. And that one thing is you’re going to take your head, and you’re going to tilt it down, and I’m going to give you a little block, and you’re going to put it between your chin and your chest and I want you to as you’re swimming, hold up block into place.

Now think about that for a second, the power of that. It’s a very focused thing on one thing, and he gave me an aid and a tool that I could actually use to know if I was doing it right. He didn’t give me 20 things to look at. He didn’t give me 50 things, he gave me one thing. BJ Fogg, who’s a great behavioral economics, behavior guy over here in the States talks about this as well, building these tiny habits. If somebody was never flossing their teeth, he wouldn’t say, I want you to floss all your teeth tomorrow, you’d say, yeah, let’s just start with one tooth.

And so the great coaches are able to find one thing that has a massive gain, that they can actually show you how to do in a very concrete way. And it turns out, that when I made that change to my head tilting, my speed increased exponentially, just with that one change. So that’s the power of a great coach.

Rich: Anyway, how did that initial conversation come up. “Jenna, I think I’d like to coach you in sales”. How did that conversation start? What prompted that conversation initially for you to coach her?

Josh: So it wasn’t so much about me coaching my wife in sales as it is about this concept of audience. So today, audience is a currency. What I mean by that is, the number of people that you can connect with and that are reached by you on LinkedIn is a currency. The more people that are viewing your content, that are liking and commenting, the more opportunities you have to start conversations and the more conversations you start, the more money you make. And so I’m really big on figuring out how to reach more people through this particular platform LinkedIn.

So how do you do that? How do you go about doing that? And so there’s two ways. Way number one is I have to find a topic that people are going to be interested in. And I have to have a point of view about that topic, which we talked about. And a third kind of key thing is we talked a little bit about is I have to figure out how to present the information in a way that’s going to be entertaining and a little charming. So all that sales content that you saw, those lessons that could be presented with me, talking them through a PowerPoint slide. It could be a post, but what I did, and it was kind of a happy accident, when we were in the parking lot one day.

I turned the camera on, and I just said, my wife knows nothing about this stuff. What would happen if I just started asking her questions about this and would I have like a deer in the headlights kind of look and would that be kind of funny. And it just turned out to be like an accident and I posted one and the reactions were so overly positive. And my wife had a really good insight on this. She says, “It’s not so much about the sales lessons, as it is that you’re actually showing a little bit about your personal life, and about me and about us and whole foods, and it really is about connecting with people on an emotional level, so they see who you are. And they like you.

I mean, I took Jenna to Unleash which is Outreach’s big sales conference here. And it was like she was a little mini-celebrity. When I do discovery calls, people mentioned her, I bring her onto the camera, and people freak out. They just laugh, they want to talk to her. And it’s just a way of connecting with people and all things being equal. When you make people feel good, and that’s what this is all about. When you caring, you’re genuinely make people feel good. When they read your stuff or watch your videos, they’re going to want more of you.

Rich: And I think as well with what you’re doing is personalizing what you do, but it’s doing it in a really authentic way as a marketer. One of the things that irritates me particularly on LinkedIn as well, it’s very easy to get attention. It’s very easy to do something that’s a little bit outrageous, just to get attention, but where I’m really impressed and where I think most sophisticated marketers go is that they that yes, they get attention, but they’re doing it with a really coherent message. There’s something behind it that is authentic and is real. It’s not just about getting attention, its using it as a conduit to put a strong message across. So I think that’s why the videos with Jenna works so well.

Josh: Totally yeah. Plus, she’s easy on the eyes. Let’s not mention that in case she’s listening. We all know make sure we listen. Yeah, you’re exactly right. So the lessons are really good. But the lessons are couched often in scenarios that we bump into. So oftentimes will be around Boca or will be in different scenarios, and we’ll see something that’ll happen. And I’ll turn to her and I’ll say, what does this have to do with sales, and we just kind of riff off of it. So it’s almost taking like everyday things. And I think you can learn a lot about sales outside of the traditional business.

I mean, anytime you’re seeing anything, it’s all sales. You look at banner, advertising, online, but also look at billboards. Also look at what’s going on in the malls when you’re walking around. And when the kiosk people approach you, when you’re at the carwash, when people are trying to upsell you. I mean, sales is all around. And you can take those observations that you have, like a comedian does and sort of riff off of them.

Rich: We talked to the start about the jobs to be done framework. And I think now is a good point to bring this into the conversation. Give us a little bit of a sense, from your perspective about the jobs to be done framework, because I know there are going to be lots of people listening to this, who will have never heard of it, but are probably missing out by virtue of the fact they do not know what is jobs to be done. Give us a little bit of background on it.

Josh: Yeah. So I’ll give you guys a couple of examples because I think it’s the best way to describe it. In short, what the value it has for a salesperson or a marketer is it’s the only approach that I know that will allow you to get to the reasons why people bought. And it turns out, you can’t ask people why they bought things, because they don’t know.

I’ll give you an example. We were doing some jobs to be done interviews at base camp. My friend Jason Freebus, tell me about the story and there was, I don’t know 30 or 40 people at base camp and they asked the audience what was the last time you bought something and people sat well, I bought a car, I bought a piano. This one person bought a light for his book, the little lights that you clip on your book.

Jason asked him, why’d you buy the light is that I just wanted to read in my bed at night. It turns out when we brought this person onto the stage and actually started doing the jobs to be done interview, we learned that that’s not why he bought the light at all. He actually bought the light to save his marriage. What was happening was he had the light on in the bed at night, his wife wanted to go to sleep. So he would leave the bedroom or she would leave the bedroom. This was happening regularly. And it started having effect on their marriage. And so by buying this little nightlight, he was able to stay in the bed, she was able to stay in the bed and repair their marriage. And these are the insights that you get when you actually apply this job to be done, interview technique.

You actually start to understand the events and circumstances that took place that actually cause someone to buy what it is that you’re selling, and it’s oftentimes very different than the marketing language that you are given. And when you apply this language into your cold email scripts, and your cold emails, because people feel like oh my god, you really understand me. That’s exactly how I talk. That’s how I describe my struggles, or the opportunities or the desires that I have, they’re more likely to want to listen to you.

Rich: How can an SDR use their sales conversations with prospects to try and uncover this? Because in the example, you’ve given a great example, as it is, it was relevant to the context of that conversation, getting somebody up on stage, asking them those sorts of questions in it, how do you translate that into a sales scenario where the SDR may not fully understand what jobs to be done? Their prospects are typically doing. Yeah. How can we translate that into a sales context in particular?

Josh: It’s a great question. First thing we have to realize is everyone when they go to work every day has a job they want to get done. So when you go to work every day, there’s a job that you want to get done, you get to work at nine o’clock, you leave at five or six and you’re trying to get work done specifically. And the problem is, is that SDR is usually haven’t done the job of the person that they are contacting. And so they end up falling on this marketing lingo or generic lingo. It’s oftentimes disconnected. For example, the job of a barbecue for me is to cook salmon and the way I cook salmon is I take the salmon out, I put it on a grill, I flip it around, I season it so that I can actually serve it to my wife and that she can have a happy dinner and feel good and say, “Josh, that was awesome dinner”. So your prospects have these jobs too.

The way in which you understand their jobs, and this is a really, blatantly easy is you actually have to talk to customers that bought within the last 30 to 45 days and use a series of questions to be able to understand what was going on. If I bought a $10,000 mattress, I didn’t just wake up One day and buy a $10,000 Richress. So I might start by saying, “Hey, looks like you bought this mattress 15 years ago, tell me When was the first time you thought about buying a mattress?” And they might say, “Well, that was about four months ago”. What was going on four months ago that caused you to start thinking about buying a mattress?” “Well, my back started hurting. And I started to kind of look at mattresses”. “What happened next?” I didn’t really do anything because my wife’s back wasn’t really hurting. So I just kind of moved around a little bit and use some pillows and nothing really happened.

“Well, then what happened after that?” Well, then my back started hurting again. So we flipped the mattress over, and that worked for a while. So what you’re seeing here is a lot of events that are happening during the journey, before someone actually decides they want to actually start actively looking and actively shopping and actually ultimately buying. On the other piece of the framework is there are always things that are pushing people to stay with what they have. Because of a lot of anxiety of buying a new mattress. I’m not going to like it? What happens If I don’t, I’m not going to waste my money, is it going to be the same thing? Is it really going to fix my back problem?

In the context of work, the anxiety is if I hire your product, and I fire what I’m currently using, am I going to lose my job? Am I going to lose my reputation? There’s a lot of risk involved. And people are pretty risk-averse. And so generally when the anxiety is too high, and the pull of something greater is too low is when people start to have inaction. And so by understanding all of these forces, it forces an SDR or anybody to start thinking like a buyer, rather than a seller. The other huge advantage of this is, once you’re in the framework, you’ll know where someone is in a buyers journey. And you treat them differently. It’s not the same discovery call for everyone.

So if I asked someone, how long you been looking into this, and they say, well, three months, we’re finally at the end. I’m not going to go into a big discovery conversation, I’m going to say what do you need to know? So if I walked into an apple store, with a hard drive that was about to burn out and I need get my files transferred over immediately because I have a keynote next week, the last thing I want is for an apple rep to tell me how great the Mac is or asked me a bunch of questions. And they say, “What do you need?” I’m like, “I need to get my stuff off this drive on a new machine like ASAP” Versus someone that’s at the beginning, I would never ask that question. So it really helps you understand where someone is in the cycle. And so that you can have the appropriate conversation because oftentimes, it’s not a one size fits all.

Rich: And one of the examples you gave there with the mattress, you can see some of these newer startup companies now which are doing Richresses in the post in the UK, I’m sure you guys have them in the US, where you’re ordering a mattress online, is being delivered in the mail, and then you’ve got money-back guarantee. It’s de-risking some of those points that you’ve alluded to, by understanding the jobs to be done. There’s a huge risk element in making such a significant change. And some of the companies out there, in their marketing and in their sales method will de-risk that as part of the process.

Josh: You’re so right. We often talk about benefits in sales and marketing messages, but we never really start to focus on the risks and the anxiety and jobs to be done speak that people have of switching. I went through a similar thing with the bike. In the states, it’s normal to buy a bike when you go into a shop and you buy a bike, you can see it, you can ride it a little bit. But the bike I wanted was only available online, you have a lot of anxiety, like once if I get it, I don’t like it. And the company obviously did the research, they knew that and they said, hey, not only can you try it for 30 days, but if you don’t like it will come by, we’ll have a person come by, take it apart, put in the box and ship it back at no expense to you.

So that’s the same kind of idea there, which is understanding the anxiety people have and jobs is really good for this. Just shifting your whole mindset. I know we talked about this in the beginning, from the seller centric mindset to really understanding where the buyer is, because when you contact the buyer, spoiler alert, somehow they’re getting along just fine without you, somehow if they never talk to you again, they’re going to be fun. So when we come in with this, oh my God, they need this thing right now, it’s just not the case. We have to just understand that they’re probably getting the job done today, but they might not know it could be getting it done better.

And a really great example of this is a blender story I tell him. I had a Breville Blender which was awesome. And the job of that Breville Blender was to make smoothies so that I had something to carry on the way to work and the car, wouldn’t be too messy, it would satiate me and it would keep me full for a while. It was great at doing this job. You cold call me and start talking about my problems, my blender, I don’t have any. Until I walked into William Sonoma one day, which is a retail store here in the States. And I saw someone demonstrating a Vitamix blender and they were making soup in a blender that was hot and my mind was blown. I’m like soup in a blender like I love soup. But how does it get hot? Apparently, the blender heats it up and then they were showing me how to make nut butter I saw it was possible. So it’s not just about the problems. It’s also about possibilities. And once I saw it was possible with the soup and the nut butter, I was a buyer. Because I didn’t even know I could do that.

It’s the same thing with your buyers when you’re cold calling them. In addition to struggles, some buyers want to do things better but might not know what’s possible. And it’s your job to not only find problems or struggles, and have people relate to them, but also expose them to opportunities. Shine a light on what they could be doing better. Jobs teaches you there’s a lot, which is everyone wants to do things better. They want to get to point A to point B in a more efficient, better way. We all want self betterment. It’s why you’re listening to this podcast right now. It’s why you read books, and it’s why your prospects will be drawn to you, if you can show them how they could potentially be doing something better as well.

Rich: When you was talking about the blender example, I thought you might go to the McDonald’s milkshake example of this because that’s like the default. If you’re talking about jobs to be done, you’ve got to mention the McDonald’s milkshake example. So you didn’t do it. So I get to do this. So for those people who just … Okay, I think I understand this. Let me make this a little bit more real. So, Clayton Christensen, the guru behind Jobs to be Done if you like one of them at least, is doing this research projects and they’re talking to people about the McDonald’s milkshake. They want to try, and increase milkshake sales, and they can’t figure out what’s going to increase sales, what’s going to drive sales, what’s going to get more people to buy these milkshakes, they start to have these sorts of conversations with buyers of the milkshake.

Turns out, the job to be done with a milkshake is to alleviate the boredom of a long commute. They were talking to people in the morning, they were buying the milkshakes in the morning. And it turns out that the reason they were doing it was because they traveled for miles and miles every day. They just needed to have something in the other hand, steering wheel in one hand, something in the other, and they wanted a milkshake. And it was nothing to do with flavor, taste or anything like that. It was purely to alleviate the boredom of the community. McDonald’s tried changing the formula. It made no difference, until they started to understand what the function of that milkshake was. And I think that’s a really concrete example of just how powerful this can be.

Josh: And think about the implications for that. Because if you didn’t do that, your marketing messages would be about flavor, about fitness, about viscosity, about calories. But when you have this insight about boredom, the marketing message is completely changed because people say, you know that is why I’m drinking this milkshake. I am bored. And I do need something to satiate me and I can use a bagel, but the bagel is going to get messy, like the competition of the milkshake is a bagel and a banana. But the banana isn’t as easy to eat and it’s over with really quickly, it turns out the milkshake does the job better than the competition.

Rich: And as a marketer, immediately your mind goes to an advert of somebody in their car, really dreary commute. And then all of a sudden the milkshake appears, it changed it. It totally changed. If you’d have said that to somebody, they would have thought you were crazy.

Josh: That’s right.

Rich: But understanding the jobs to be done framework allows your sales and marketing messaging to be so much better. So huge fan of it. Is it something that you implement where you are right now in terms of the day-to-day? What are the jobs to be done of your clients? What are some of the jobs they’re looking to try to solve.

Josh: Absolutely, I learned it over at base camp. And when I engage with clients, it’s the first thing we do. I mean, I will interview, I can do it, or clients can do it using the Jobs to be Done framework. It’s something you can learn, myself some material on it. But there’s a lot of material on the internet as well and kind of glean. It’s a skill that you can learn and you actually interview your customers. And you get those insights. And those insights form the basis for your outreach, or even your website.

Rich: So we’re running up on 50 minutes, Josh, I really appreciate your time. There’s so much we could talk about, so many places we could go, really appreciate the value that you’ve delivered on the show. I knew you would. I’ve really enjoyed this conversation. It’s been fantastic. For people who want to find out a bit more about you, I’m guessing you’re going to point them in the direction of LinkedIn, but is your chance to put it in your own words, where can people go to find out more about you?

Josh: Yeah, LinkedIn is great. And if you’re interested in some of the materials that I talked about, I sell a guide called the Badass B2B Growth Guide. If you want to learn more about that, you can go to, and a lot of the concepts we talked about and some more detail are in that guide. And I also want to thank you for the opportunity. I know you have your pick of people to have on these podcasts. And I’m super grateful that you chose to spend some time with me. I’ve had a great time here and especially a chat with Joe as well.

Rich: Great stuff. I’m sure he will know about this. One thing before we go, I like to ask guests from time to time. Any book, any particular book that you would recommend, doesn’t have to be business, it can be on any topic. I know, people are listening to this in their ear buds, they’re going to be consumers, probably on audible. They’re going to enjoy learning, they’re going to enjoy reading. Is there any book that you would recommend to somebody listening to this podcast, be a business or otherwise?

Josh: I’m going to do two if I may, because it’s such a toss up between the two books. So one of them is called the Slight Edge. And this is a book on how you can have a proper mindset which can help you succeed in anything. It’s a great book. Another one that I really love is called Never Split the Difference by Chris Voss and this guy was an FBI negotiator, teaches you how to negotiate through the lens of an FBI hostage negotiator, which is super interesting and lots of great implications for sales.

Rich: Yeah, I love that book, massive fan of that book. That’s brilliant. Great stuff. Josh, thank you, once again, really enjoyed the interview and have a great day and send my best wishes to Jenna. She’s a star.

Learn More

Download The Complete Guide to Conversation Intelligence to learn how Conversation Intelligence can help improve sales coaching, content, and training.

See Allego in Action

Learn how to accelerate training and empower teams with modern learning that delivers real business results.

Demo Request
Gartner Market Guide to Sales Enablement Platforms
Gartner Market Guide for Sales Enablement Platforms

Prepare for the Future of Sales Enablement

Get Your Copy