Understanding Job Moves and Talent Management featuring Bob Moesta
16 Aug 2025 · 30 min
Bob Moesta explains why people change jobs using Jobs To Be Done thinking. Most moves aren't about money but about being pushed out of a bad situation or pulled toward something that matches your energy and strengths.
Welcome to the Selling from the Heart podcast on the from the Heart Business Network. You've joined a global movement of sales professionals who are dedicated to being authentic and building trust. We call it Selling from the Heart. Together, we're on a mission to bring sincerity and substance to the sales profession we all love. Get ready to be inspired and equipped as we join our hosts, Larry Levine and Daryl Amy.
If you love the Selling from the Heart podcast, then you know how much we value authentic leadership and building relationships with heart. But here's the thing. Great leadership doesn't stop with sales. It starts at the top with CEOs who inspire trust, create meaningful cultures, and lead with purpose.
That's why we're excited to invite you to get involved with the Culture from the Heart podcast. On Culture from the heart, we celebrate CEOs who are transforming their companies by putting people first. And we're asking you to help us find them.
Do you work for an incredible leader? Know a CEO who builds culture from the heart? Nominate them to be interviewed on the show. Together, let's spotlight the leaders who make businesses thrive by leading authentically.
So head over to culturefromtheheart.com to submit your nomination today. Because when leadership starts with the heart, culture and success, follow. Hello and welcome back to the Selling from the Heart podcast. Your co host, Darryl Amy, here today with Larry Levine. What's going on, Larry?
All kinds of great things for those of you who are watching us on YouTube. Daryl's got a great Selling from the Heart shirt. I'm repping red. He's got Selling from the Heart shirt on. We're going to have a fantastic time here today, Daryl.
We've got a job to be done and that job is to have a great conversation with our friend Bob Mesta. Just wait. This is going to be a lot of fun. We're having fun. We said we're going to keep it hot all summer, and as summer keeps going, we're definitely keeping it hot. And one of the things we love to do is to stay in touch with all of our friends around the world who are in the Selling from the Heart community.
I just want to give a special shout out. I just recently had a conversation with a great, great leader by the name of Chad Udy. Eudy. Great guy. I was introduced to him by a listener of our podcast. I had a great conversation with Chad. Great leader. Wears his heart on his sleeve. But he does know what Selling from the Heart is all about. Chad, I appreciate you.
Yeah, shout out, man. And we love to hear from you. If you're listening in and we're not connected to you, reach out to us on LinkedIn. We'd love to get to know you. Well, today's guest is truly remarkable. He's a pioneer, an innovator, and an advocate for uncovering what really moves customers. We're honored to welcome Bob Mesta back to the studio. He's the co creator of the groundbreaking Jobs To Be Done framework. He's the best selling author of one of my favorite sales books, Demand Side Sales 101. And he's the author of his newest book, Job Nine Steps for Making progress in your career. Bob is the president of the Rewired Group. He's a research fellow at the Christensen Institute, and he's a respected thought leader who has literally helped launch over 3,3500 products. His insights have helped audiences at Northwestern, Kellogg School, Harvard, mit. Look, Bob is a true thought leader. He's passionate about sales. He loves selling from the heart and he's here with us in the studio again today. Bob, welcome back. It's great to have you here. Thanks, darl.
I like that. I'm always humbled by what you say because it's kind of like when you say those things, it's kind of like, did I do those things? Yeah, kinda. I'm just a regular guy. I'm from Detroit. I just like to build shit. That's, that's the way I put it. I'm a tinkerer and I love to do it. And I learned some things early in my career that really helped me kind of take it off.
So I love it. We're glad to have you back here with us today, Bob. And as we get started, you know the question that every guest on Selling from the Heart answers, you get another stab at it here today. What does it mean to you to sell from the heart?
So I think the sell from the heart is actually what my book Demand side Sales is a lot about, which is about. It's not. Selling is not about selling a product. Selling is about helping people make progress. And ultimately it's more about finding out when are they ready for my product or service. And ultimately selling from the heart is, is helping other people, period.
Oh, this is, this is so good. And this is. Peel this back on. You use the phrase helping people make progress.
Yeah.
Dig into that a little bit more.
Okay. So, so the, the notion is this, is that we, we, we are as human beings, we're actually creatures of habit. We don't really like change. And ultimately change is a hard thing. For us to do. And so when people want to buy something new, that means they want to change. And ultimately nobody buys something to be worse. They always buy something to be better. And that's what progress is, is what progress are they hoping for? 9 times out of 10, we're trying to sell them progress. That's like way up here and the reality, whoops, sorry, way up here. And they just want to make progress right here. And so part of it is being able to understand where do they want to go, not where can I take them.
Well, and I think this is such a great parallel into your new book, but I got to say to our listeners, if you haven't heard the first episode, when Bob talks about Demand Side Sales 101, you got to go listen to that. Where he unpacks these concepts around. People don't buy products, they hire them for a job to be done. And just incredibly powerful. But we want to talk today about your latest release. And by the way, congratulations on job moves. Nine steps for making progress.
Sixteen years in the making. Yeah, so this started back in almost 2010, when I've been asking entrepreneurs like, what are the top three biggest struggling moments you have in your company? And it kept coming back. Talent, boy. How to manage talent, how to figure out talent, what to do with talent. How do I hire the right people, how do I retain people better? And so, like, let's be clear, of all the people in the world, the last thing I want to do is dive into hr. Right? My little joke is HR is when legal and was it legal and finance have a baby, it's hr, right? And so, and so part of this is to realize that. So what I did is I went off and just started talking to people about what caused them to say, today's the day I'm leaving this job or leaving this company and going to that company or leaving this job and going, taking this promotion to go to there. Like all of them are just basically understanding what causes people to switch. And what's so interesting is there's like. So we did over a thousand interviews almost over 15 years. And, and ultimately we've been able to kind of distill it down to some patterns. And at the same time, we've been able to kind of help both employees figure out who they are and what they want to do and actually interview way better. And we'll talk about how to do that. But, but I've also been helping employers realize, like, they need to write better job descriptions. They need to actually talk about the challenges that are ahead for them. They need to talk about how to, how to attract people who want to actually step up to the challenge. And so it's a, it's a, I consider it like a two sided market problem. We've got, we've got employees who basically talk about themselves like they're superheroes. And I've got the employers who are making job descriptions that are like unicorns and they're trying to fit each other together. And AI is just making 10 times worse because the lies just get bigger. Right? So true. So good.
The lies just keep getting bigger. So here's the question. Go ahead.
The one other thing I would say is that most people write the resume about what they did, but it doesn't mean that's what they want to do. And the job is not about a position, it's not actually about a title. It's about what you want. What work gives you energy, what, what things can you go do where you get energy more than the energy sucks out of you because of the work you have to do. And so it's this real balance between what I call energy drivers and energy drains and being able to realize what are those things that are doing that for you? Because the moment you actually realize that, that you can actually get energy from work, it actually isn't work anymore.
Yeah.
This is so good. Hey, I got a question for you, Bob. Of all the thousand people that you interviewed over this span of time, 15 years, what are like two or three things that just like stood out that were, aha. Moments that slapped you across the face and you go, really? Come on.
Yeah, so, so, so for example, I remember interviewing a gentleman who was a lawyer and became a judge. And as a lawyer he was making like, like high, high, high six figures, right? And as a judge, he'd make low six figures. I'm like, what would cause you to take a job with less money? And he goes, I have so much more fulfillment of helping the community. And so you start to realize that money is not the primary driver of people switching. And you start to realize that. So one of the stats is, is so the way the method works is what we ask people say, oh, I switched jobs because of money. I'm like, okay, well how much more money did you get? And you know, and you start to dig into it and like, why did you want more money? And you start to realize that money's not the motivator, it's respect or it's, I have responsibilities or this is how I measure how making progress. And so Money is one of those things that, that really I like 53% of the people who told their previous employer they made more money did not. They actually made the same or even a little less to get out of the situation they were in.
Interesting.
So you start to realize that it's not just like we all, we all make it about money because it's what I call the surface level problem that people talk about. But when you get down to the root causes, I'm leaving because I get more respect here or I'm leaving because like at some point you, you, I don't trust you anymore. And so you start to realize a bad manager, like everybody's heard this a bad manager. Most people don't fire a company, they fire a bad manager. Well, you start to see the real toxicity that a bad manager can bring to a situation and how it can actually destroy your organization.
Well, this is so powerful and I want to look at both sides of the coin here. You talked about superheroes trying to take job. It would rid of unicorn.
Like everybody's like, hey, I can do this, I can get this done. What's your calling exactly? We need you to do this. And if you actually look at how they make the job description, the first thing they do is they go to LinkedIn or they go to chat GPT. They basically run up some, some things. They like what's a product manager do? Or what's a VP of sales responsibilities? And they put them out there and then, and then what they do is they pass it around and everybody then takes all the that they don't want to do go like they should be doing this too. And then it ends up being this long list of stuff that they have to do that at the end of the day, it's like, it's like, like the only way you can find somebody who wants to do all of that stuff is a unicorn. Right? Like, I need somebody who's very, very creative and an out of Botox thinker and very detail oriented and can handle budget. It's like, okay, that's, that's a unicorn. There's nobody who can do both of those things well. And so this is where we end up with mediocrity. And so part of it is, is we've been actually kind of framing the, the job market by function in a wrong way. And that over time I think they've actually all melded together. And the reality is get people. We need to have the job descriptions reflect the people more than just the position that we need to actually have filled because it's getting too hard to find the right people. And sometimes a job, a job. What's interesting is there's times where people, somebody leaves and they need to hire two people to actually do that job. And they didn't realize it till after the person left. Right. And so you realize that they're just pushing people so hard. And again, it's one of those things where, you know, there's, we have, you know, we only have one life and you have to realize that we can't think about it as like there's a work life and a home life and a golf life, if you will. But the reality is like, no, you have one thing, one life and you have to make trade offs between all of them to actually kind of live your real life.
Oh I like to say as it relates to the book, Bob, somebody picks the book up, they start reading it, they finish reading it, they close the book, they leave you a really great review on Amazon.
Yeah.
What are you hoping they get out of reading this book?
So to be honest, there's really two reasons why I wrote the book is one is I love you guys know me well enough, I love to help people but like it's very hard to scale me helping people. And so what this does is this book actually allows me to help a lot more people and at the same time be able to actually help help people without actually ever interacting with them. And so to me, I did this for both my children because I felt like them finding their way like the notice the notion of when you get to a position and you don't want your boss's job, there's no one there to navigate help you navigate what to do next. That's what this is really for. And so to me, it's those people who kind of go like, yeah, I don't want to be a VP and I don't really want to go do that, but I don't really like where I'm at. What do I do now? And so as I said earlier, this is really a reflection book that allows you to look at you and understand who you are really and what you're good at. But also what do you suck at? Most people don't want to take inventory of what they suck at because everybody's like, oh, you need to get better at this. And I would tell you like, no, you don't need to get better at it. You need to actually negotiate that part of the job out of or that part of the work out of your job description. And you start to realize that this way is really, really helpful for people. So. So I'm really hoping that to be. To be honest, it helps people take the time and not have the regret of. So the other stat we have is that the number of people, the. The moment when people know if they made the job move, whether this job is going to work or not. Do you know how quickly they know when it's going to work or not? Two weeks.
Two weeks.
Two weeks. And then if they know it's not a fit, it takes them two years to get out. Because I can't quit too soon because that looks bad. So I'm going to try to do this, and then I try that and you start and like. But I'm trying to prevent them from making a bad decision up front of going to the wrong place. Nine times out of 10, people leave places and literally go, like, I'm good at finance and I've been in the, in the manufacturing business, so I got to just go to another manufacturing business. And so they. They end up going from one place to another place and it's worse, right? And so part of it is to say, let's take a step back and take an assessment of what are your skills, what gives you energy, where are you at? And it might be the fact that you just like to analyze things. Well, I can take analysis and put it in three other industries and three different positions. So part of it is we get stuck, by the way that we've kind of organized companies through marketing, sales, et cetera. And we start to realize, like, some of the best salespeople started as customer success people, right? And eventually how do they make that transition from customer success to sales? Or some of the best salespeople become great customer success people, but they don't even think about making that move, right? And so part of it is to realize what this is about. Taking is. So people talk about strength finders, right? And I have them take a strength test when I facilitate people through this. And strength finders comes back with 34 traits that you have. And what I've realized in analyzing all this is that, like, my top 10 strengths have been the same for me for the last 20 years. So I've been taking strength finders since 2005. And my weaknesses are the same thing. But what happens is when I have hr, come to me and tell me that, oh, you've got this weakness of like. So one of the. One of my biggest weaknesses is harmony, which is where you're supposed to be able to get Everybody to get along. And basically, you try to minimize all the friction that's in the possible. The fact that what makes me a great innovator is actually I create friction. I need friction because the best ideas come out when we argue. So if they want me to be more harmonious, they actually strip me of my superpower. And so what happens is, when I'm really good at this, the fact is, then they try to make me better at this. And I try to bring that up, it brings this down. And so I just become mediocre. And so what it's trying to do is actually help you see what are your unique abilities, what do you really love to do, what gives you energy. Right. So one other last. There's a lot of learnings in this, but one of the last learnings I'd say is that Most people spend 90% of their time doing work they hate for the 10% of the time the. The work they love. And if you just change that ratio to 50, 50, you don't even think you're working. Wow, that's just a kind of amazing kind of insight to me.
I think that's extremely powerful. And of course, we've got sales leaders listening in. You've got people on your sales team. And I think the question is, do you understand, do you know the people on your sales team? Do you know what their strengths are? Do you know what their weaknesses are? Do they know their working genius? Do you know what their why is? Do you understand the people on your team? Or are you just looking at them like a production machine? And then you wonder why the engagement's so low and the turnover so high? I think this is extremely powerful. What else would you say to leaders?
Yeah, so a couple things. One is, so again, if you pick up the book, the first eight chapters are really about the, you know, kind of the process to. To do this. And so one things that we've been doing for leaders is we're actually having them use the book as actually the, The. The recruiting process. So if you want to apply for a job, we want you to go through this process. And so, for example, I prototyped that with myself when I was hiring somebody. Hiring somebody. And to be honest, I, I end up going through 10 candidates. I found jobs for. For seven of the 10 candidates, and I hired one of them because I. When you get to it, it's like, yeah, you're not a fit, but you're. Oh, my God, you're so awesome thing, right? And this is where you're awesome and to be honest, you. You would be miserable here for this and this and this reason. Like, you're right. I'm like, okay, but here's where you can go. And so most people try to morph themselves to fit the job because they want the job so well. And it literally is. Is is one of the word. Like, this is kind of the opposite of selling from the heart. They're. They're literally not being themselves, not being true to themselves. And this allows you to kind of do that. And most people say, I don't know how to do it. My thing is, is if you say, like, look, look, I'm really good at these things. This is the stuff that gives me energy. And oh, by the way, these things probably take me a little bit more time than everybody else. So if you. If you want me to do it, I'll do it. But the reality is, if you get that off my plate, I can do more of the stuff I'm really good at. And people are negotiating. Instead of negotiating salary, they're negotiating scope of work, and it's allowing them to be way more satisfied.
Oh, interesting.
So then, so then what do you suggest people start doing then?
So the first thing is, can I share my screen?
Yeah, I think so.
I think I could do that.
Absolutely.
This is why, okay, if Bob shares his screen, this is why you got to tune in and watch Selling from the heart on YouTube.
That's right. That's right. Yeah.
I just gotta find it. Here it is. So this is the slide I want to show.
Can you see that? Good. It'll come. And it's coming up.
Think of the last time, almost the job you had before you started this. Right? And these are the things. These are the. There's like 14 poll or pushes that basically, if there's no push, you're not looking for a job. But ultimately you have to have four of these. So I can't read them, but if you could read them. And so for the audio portion. But how many of these are actually part of your reason why you left your previous job to start this?
Well, I'll just hit a couple. I mean, have more time to spend with others in order to carry my weight. My values and beliefs are aligned with the company and the people I work with.
Oh, wait, I'm sorry, I'm sorry, I'm sorry. I have the wrong ones.
Oh, there we go. Pushes I don't respect. This is a push to get you out of.
That's a push to get you out. Those are the polls. I'll Tell you about the polls.
Don't respect or trust the people I work with. Feel like the work I'm doing has little or no impact on the company or the world. The way I manage is wearing me down. My current company is struggling and the end feels near. I feel disrespected. I can't see a place for me to grow. There's a great list.
I think if I look at the last one. I'm sorry, just real quick, Bob. The last one is so spot on because how many people have experienced this? They feel like I'm on my own, ignored and not supported at work.
Yep.
And so what happens is, it's interesting. I always. So I have four children and I always ask them, how was your day? How was work? And what I'll tell you is if I sense four of these, right, I know they're looking for a new job. And so what we've done is we've taught. We've taught managers to sit down with their direct reports and say, like, all right, like, how's it going? Let's talk about the progress you made in the last three months. Let's talk about the progress you want to make in the next three months. And then you throw this on the table. Go like, are any of these things happening that we need to talk about? And it's the uncomfortable conversation, but because it's research based, it's like, yeah, let's talk about, you know, I don't feel really respect. I don't respect or trust some, some of the people on team. Well, let's talk about that. Like, why don't you. And how do we actually manage that and what do we do to, to earn the trust back? Right. Because here's the thing, if there's no push, they're not looking.
Yep.
Right. And now the other part, though is this is how you retain people. Is. The thing is, is, is the, the reason why people stay is these things. Right. I get to spend more time with my family. I get to have. I. I'm more aligned with the values and beliefs of how you guys run your business. I want somebody who, who values my experience. Like all of these things, I'm, I'm randomly seeing words. So just. Yeah, if you want, if there's others you want to highlight, you can do that. But this list helps you basically understand, like, why are you here? What am I helping you do? And the more you can actually have more of these as part of the job description and part of the job review or the position review, you can start to realize, like, okay, this is how I'm going to retain people. And so it started out of, like, just helping people figure out how to switch jobs. But what it actually turns in is it's an insight to not only how to recruit people, but how to retain. So I have a talk I'm working on right now, which is how to hire and retain top talent for your amazing team. And so it's like the first book, Job Moves one was really about the employee. Job Moves two is going to be more about how do we actually help employers. And so I have, like, probably five or six companies. I'm prototyping different ways in which to do this. So, like, we've had some companies basically take the book and like, I think I've already said, use this as, like, if you're going to be a candidate and you make it through the second round, then you have to read the book and come talk to us about what you learned from the book.
Wow.
And so it allows them to have such a transparency into what people really want. And then they end up. And this is the craziest part to me is because job descriptions are like, I never knew this. Job descriptions are made up. They're just made up. Right. And so the fact is, if they're made up, I can change them. And so people who go through the book are allowed to basically, or learn how to negotiate to change the job description so they can actually be more satisfied. And they don't. And to. Here's the other part. There are people out there who love to do the stuff that you suck at.
Yes.
Right. So, like, I ran a sales group. I ran a sales group when I sold homes, right. And one of the things I realized really early here. So I'm gonna stop. How do I stop sharing?
Oh, it's good. You're good.
I go back here and X. Right, There we go. Now we're back. When I ran a sales group, what I realized is the fact is, is that most people, like, like a salesperson had to be really good, like, all the personal stuff. And then when you're building a house, they had to be really good at the paperwork. And it was almost impossible to find somebody who was good at managing a project and knowing how to sell and close houses. And you started to realize, like, at some point you were always yelling at them like they weren't selling enough or they weren't closing enough or they weren't actually. They sucked at kind of the selections and all that other stuff. And so I realized, like, this isn't one job. I need to actually create two groups. People who, who love to do the project management part of it and the people who love to do basically the selling part of it. And by just breaking that apart, I quadrupled sales because not everybody had to sell. Like, I got people who could sell, they could sell anything. They didn't have to sell just in their development. They could sell in any development. And so now all of a sudden, the salespeople could sell and the sales assistants could actually help with all the paperwork. And they were more customer success people. Back then, we didn't even know that customer success was a word. That was so long ago. But ultimately it's the notion of learning, like why, like when you have a job that's really hard to fill, typically it's not actually, you're not gonna. It's. It's got contradictions in it. So you gotta analyze to say, like, why can't I fill this position? Right. And. And so part of it is being able to figure out how to actually find the right people to do the most essential things where it's actually important.
Fascinating.
Hey, Daryl. Misalignment of the heart.
Yeah, yeah, absolutely. Well, absolutely. This is incredibly. I knew. You see, anytime Bob shows up, there's an incredibly powerful framework. It's got push and pull. It's got the same stuff that's in the demand side, sales.
It's just for hr. I mean, I'm trying to cover the whole organization. I've done a sales book, I've done a product development book. I've done a customer success book. I've done an HR book. I'm not doing a finance.
I was going to say we'll have you back for an accounting 101.
No, no, no, no, no.
I think this is incredible.
I'm a creative guy and I. I have no concept of creative accounting. And creative accounting usually lets you.
Not a good idea.
That's not a good one.
Hey, Bob, I just want to say, first of all, thank you. I think this framework we've talked about today, I want to encourage really everybody listening, all the sales leaders, all the company owners and sales professionals. This is a type of conversation you want to be having. This is some of the deep reflection you want to be doing on yourself and also on the roles in your company if you're a leader. So Bob, how can, how can folks get more.
Bob Messing, I would say for the topic, there's a jobmoves.com is the website. We have some free resources on it. I think we have the first chapter in the book. There's stuff that can kind of get you started. I also have built a platform off of this called My Next Chapter. And so I have an AI agent that actually mimics me to actually interview you about why, like, what do you love, what don't you love, what gives you energy, what sucks? Your energy. It just helps you through the process of self reflection.
Cool.
And then like, if you really want to interact with me, I would say LinkedIn is the best place for it. But if you want to learn more about. The company I have is called the Rewired Group and we do basically projects and consulting around these kinds of topics.
I love it.
So good. I appreciate you, Bob. You're awesome.
Always fun. Thank you. What a pleasure.
Always thinking out of the box. You can count on that.
I love it.
We appreciate you, man. And what a great conference. It's always fun. I love talking to Bob Nesta and I think the framework here is, is something that literally like, you got to go grab this book and you need to be thinking about this, especially if you're a leader. Incredibly, incredibly powerful concepts.
Yeah. You know, and I just flip the script on this and just say, you know, for the. For salespeople that are out there or actually anyone who's out looking for that next, whatever that next is, however you define it, don't settle. Look inward. Find out what you're really good at and passionate about. Then find the company who aligns to your thinking. They're out there. Just don't settle.
I love the concept of making the candidates read the book too and talk about it. It's brilliant. Really, really cool. While you're at it, grab this. I'm telling you, demand side sales 101. You're going to thank me and definitely thank Bob for this book. So all the links will be in the show notes. Larry. We promised everyone we're going to keep it hot during the summer and it's definitely hot outside. It's hot in here. At Selling from the Heart, we got good stuff coming up. Great things are going on. So thank you for tuning in. Thank you to everyone who's liking and leaving reviews for this show. It's helping us spread the message of Selling from the Heart all around the world in the profession we all love.
Yeah. And we just encourage you tune in because when you tune in, you get to hear great people with great thoughts, like Bob Mesa, our commitment, fresh ideas, new ideas, sometimes even push you out of your comfort zone.
And there you have it. Well, thank you everybody. For joining us today. Till next time, keep being genuine, keep being authentic, keep building trust. Do the work around what you really want from your job, and most of.
All, sell from the heart.
Thanks for listening to the Selling from the Heart podcast. If you enjoyed the show, make sure to hit the subscribe button so you don't miss an episode. We appreciate your encouraging reviews as it helps us spread the word. As always, we would love to connect with you, so look for us on LinkedIn, Facebook, Instagram and your favorite podcast platform. This podcast is produced by our friends at Salescast. Learn more at www.salescast.co. we look forward to seeing you next time.
More from Bobby
A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals)
How to find work you love | Bob Moesta (Jobs-to-be-Done co-creator, author of "Job Moves”)
556: 9 Steps for Making Progress in Your Career with Michael B. Horn and Bob Moesta
Decoding Customer Insights, Trust, and the Jobs-to-be-Done Framework with Bob Moesta | E1943
Getting real with jobs to be done – Bob Moesta (President, CEO, The ReWired Group)
#38: Shaping up to deliver big and meaningful software products | Talk with Ryan Singer - Author of the book Shape Up, founder of Felt Presence, and former Head of Strategy of Basecamp