Focusing on the "Person" in Salesperson. Just as much as the Sales

What up, everybody? Welcome to another episode of the live Better Sell, Better podcast. This is your host, Kevin Dorsey, AKA kd. And today we're gonna talk about reinventing yourself, Right? How can you reinvent yourself? How can you reinvent your career? So often we might fall into a career. So often we might fall into a job, we might fall into a company that maybe doesn't connect with us, maybe isn't our forever job, maybe has us miserable, burnt out, worn down, whatever else. But so often we feel stuck. How do we change? How do we navigate the career path? How do we find and ideally create the career and the role that makes us happy, allows us to live the lifestyle we're looking to live and honestly just have more joy in life. And that is why I'm so happy to have Heather Feidaart on the show with me today. She's the director of sales at Fidelity Labs and a startup incubator with infidelity. And she is going to talk about how to do this because she coaches reps, she coaches leaders, she coaches people on how to navigate and reinvent their careers. Heather, welcome to the show.

Thank you so much. It was quite the intro. I got to try to match that energy now.

I mean, that's kind of why I do it. I've been told it's the only reason some people show up to be a guest on the show is just to hear their intro and then they're like, I love it. That was good. So as we dive into this, right, because, you know, we don't do a lot of prep for these shows, I pretty much just ask someone, what is the topic? And we go from there. And this was the topic you picked, like, how to reinvent your career, how to build a career you love. Because why? Why is this so top of mind, like, why? If you get to pick one thing and this is it, why is this where you're putting so much energy and focus right now?

Yeah, I think, you know, it's been a topic that's been near and dear to my heart forever. It's something that I've had to do kind of throughout my career. I've been in sales for about 15 years, sort of oscillated between startups and large companies and individual contributor and leaders. And now I have the opportunity to work with a lot of sellers and aspiring leaders today. And the bottom line is really just that sellers are unhappy. Like you said, workers in tech are burnt out. And in my opinion, it really is just boiling down to so many people making career decisions based on the perception of, you know, quote unquote, what they should do rather than what they love to do and rather than what they're great at. So really it's a topic that I'm passionate about. You know, just before we kind of hit record, I was on LinkedIn and I saw, you know, very top of mind, very topical today that the LinkedIn top story was that 47% of workers surveyed over the last six months are planning to change jobs this year in 2024. And if you look at the stats just across, you know, tech in general, it stays 47%. That's a lot of people who are really unhappy with where they're at and wanting to make a change. So you know, at the end of the day, I think, you know, we've all been there, maybe some of your listeners or a bit earlier in their career and at that point in time you might just have to take kind of whatever comes along and be opportunistic and walk through any doors that, you know, might appear open for you. But at some point there comes kind of a bit of that rub where you have to really start being intentional about what it is that you want in your career. And more importantly, what I'm seeing not happening is being really honest about kind of what makes you happy and what aspects of your career on a day to day level is it that you enjoy? I think at the end of the day, you know, we spend so much time with our co workers and in our careers and that comes home with us. It impacts our mental health and our sense of purpose and our sense of well being. So it's so important that we start to be really intentional about our careers and putting ourselves in situations where we can use our strengths on a day to day basis and feel kind of proud about what it is that we do.

So you've been in the game for a minute like I have now, have you noticed a shift? Like I don't feel like it's always been this way. Like you're talking about 50% almost are not just looking for a new job but like unhappy. To me those are also very different categories. Right? Of like they're unhappy. Like have you noticed a shift? Has it always been this way? You feel like, like what is your observation been?

I think so. I've been coaching folks for several years and I think my observation is really just around you kind of get this, that midpoint of your career kind of like I said earlier, where you know, you decide that want to have kind of a career in sales and Then all of a sudden you're thinking like, do I go into leadership? Do I do a different kind of sales? Do I change industries? And now we have kind of so many choice and so many different options. Like I know when I think back to when I started out my career in sales, there was full cycle account executives and that was it. Like there was no, there was no rev ops, there was no so many of these specializations that we have now, which is incredible. I think there's just been this rapid pace and change in terms of innovation and now ongoing with AI that there's who new career paths that we're not even aware of. And so I think at some point people stop and kind of reflect and look around them and think, you know, I don't know if I'm in the right seat anymore.

So let's kind of keep going down that path there then. Right? Like what are the signs or what are the questions you have people ask themselves to know, like whether they're in the right seat for them or is it a, you know, because there's a. There could be a role issue, it could be a company issue, it could be just maybe not a role fit issue. Like what are some of the things people should be looking at, listening for, like asking themselves to know, like is it time for a change or is this actually worth kind of sticking out?

Yeah, I think one of the things that's top of mind for, for me, and maybe it's just a lot of the folks that I'm working with from a kind of a coaching perspective is kind of when you're at the inflection point and you're saying to yourself, you know, maybe I should move to say you're a BDR and maybe you're thinking account executive, or maybe you're a emerging account executive and you're thinking enterprise, or maybe you're about ready to think about leadership. Start to really think about what it is you want for yourself and what are the types of activities that you want to be doing kind of on a day to day basis. And for me, I bring up those examples. It's because when people start to think about their careers as a very linear kind of progression that somebody else is predefined, you're not defining and you're doing it because you again, should do it. That word should is always coming up, take a step back and take a beat back and say, why should I do that? You know, why is it this important to me? What is it that I'm looking to gain or to learn, you know, I'll give you an example. So one of the things I constantly hear is people think, oh, I've been in sales for a few years, you know, made some good money, you know, I like doing it. Maybe I should get into sales management. And the first thing, and it's the, you know, common story. I've seen it a million times. You know, you see your best seller get promoted into a leadership role and then they're miserable. And you have that high turnover in sales leadership, one of the highest, I think, in any corporate positions. And so I like to just start with one question. And it's my favorite question to ask because people always have like a really strong, almost like visceral reaction to this question. And then they say, I'm thinking about getting into management or should I get into management? The question really is, would you rather do a job yourself or would you rather be responsible for other people's work? And it's fascinating to see people's body language because it's almost this visceral reaction where you can see it right away. They're like, oh, no, I don't know. I like to have control of things. I like to own the outcome. I like to be in the driver's seat. That might be an indication that you might not be best suited for a leadership role, but maybe you can use your leadership aspirations in a different kind of role. Maybe you'd be better suited to say, enterprise sales, where you are leading, but you're kind of leading through influence, but you're not ultimately responsible for other people's work. So it's starting to ask yourself kind of some of those, those questions. The other one I hear often is, so if a seller's doing really well, you know, they're hitting quota, they're liking what they're doing, maybe they're in like an emergency or a mid market, for example, and they say, okay, well I got to get to that rung. Because that's what you do, that's what sellers do. And there's this, you know, linear progression that people laid out for me. But sometimes those skills aren't always transferable. Right? So continuing on through that example, maybe if what it is that you love to do kind of day in, day out is like, you love the thrill of the win. Like there is no better point in time in your day than to see, you know, docusign completed in your inbox. Like, that's your heaven, that's your nirvana thrilled. And that's what you're proud to tell your Friends and family about at the end of the day. So maybe for you, going into enterprise isn't going to make a lot of sense because you're really only going to have those moments a handful of times throughout the course of a year. You're not going to get those little like dopamine hits that you really love and like that you really love about your job. So that's, I think the first place to start is kind of really understanding what it is you love and really kind of getting into the nuance of some of those details. And I can tell you a little bit more about a couple of other examples there as well.

So how do you coach people on. I'll say like, like the balance. Because there has been. I'll say. I don't know if it's a shift or not, but like the, the narrative got really heavily pushed. Like, you know, do what you love, do what you love. You gotta love the, the process. Whereas it's like there's parts of any job that aren't always the most enjoyable thing. Right. And I think sometimes people get lost in that. Sometimes like they're in a job where it's like they're focused on the things they don't like in it versus the things that, that they do. Like. But it's almost hard to find like this role that's like the I'm only doing what I love type thing in terms of the activities. How do people like navigate that or balance maybe the trade offs of like. Because as like I'm an svp, there are things I love about it. There are things that drive me absolutely insane.

Yeah.

If I was like, like, do I love everything I do? The answer is no. It's just there's the parts that I do love offset it. Like how, how do you help people navigate that? Because I think especially for people early on, I feel like they sometimes make, they take, do what you love too far and like they miss out on, you know, some of the things that would have gotten to them to where they want to be. I hope the question makes sense.

Yeah, it does. There's. I'd love to answer that question. There's a couple of resources actually that come, you know, kind of top of mind a couple of books that kind of help maybe answer a couple of those questions that I would recommend to anybody who's sort of having. That is a bit older now, but it's a great book. I think it's a Mark Manson book. The Subtle Art of Not Giving F word. And that's a Great book. Because, you know, he'll talk a little bit about kind of, you know, every job has, you know, horrible components, the things that we don't want to do, but you just have to kind of find your own brand of the things that you don't mind doing. Like, you're never really going to love everything that you do. I think that's an unreasonable expectation. It's more about getting grounded in the reality of what the day to day activities of the role is going to entail. I think that's kind of the key thing. And then maybe striving for a balance. So maybe, you know, getting to do the things that you love kind of maybe 50% of the time versus those things that you loathe doing. Listen, just in the world of sales in general, nobody wants to be in their CRM all the time making activity updates. You don't want to be running reports for your team. Like nobody really ever wants to be doing that. It's just a nature of the role. And so probably put that in the load category. But one of the things, there's a second book recommendation actually I'd love to make too. It's a book that's recently actually come out called Love and Work by Marcus Buckingham. And he has this concept of talking a little bit about. He refers to them as red threads. But really what he's talking about is kind of honing in on the specifics of the things that you really love to do. And when we say love, let me just break that down a little bit because when we talk about love, really we're talking about like, how can you do more of the things that you enjoy and that you're naturally great at every day. And one of the good ways to think about that is like the activities where maybe you lose track of time or where you naturally enter a bit of a flow state or where your colleagues come to you and they're like, hey, you're really great at this. Can you kind of teach me that or coach me on that or share with me kind of your tips and tricks? It's, it's those activities. It's the. And sometimes it can be really getting into like the crux of what it is. And so like an example that I can even give for myself. So I love giving presentations. I think it's a blast. I'm one of these people, you know, maybe occupational hazard. I love to give sales presentations, but it's not asking the question of like, what is it that you love about that presentation? I get really jazzed up after it goes well. But if I really break it down, was it the designing of it? Not really. Was it the storyboarding of it? Yes, absolutely. I love storyboarding a great presentation. I love using client examples. Was it the execution or the flawless delivery? No, I'm not motivated by perfection. Was it maybe that the presentation kind of resonated with the audience? Yes, that's something I absolutely love, like, knowing that my presentation resonates. And more importantly, I'm really motivated by momentum. So if I deliver a great presentation, at the end of the day, what it is that makes me feel so good is that I moved others to act, and maybe it's that I got a yes to my next steps. That's specifically what I love. It's not about the presentation. It's not about the PowerPoint. It's a little bit about the storyboarding, but it's mostly about kind of that aspect of kind of momentum and that forward movement that really jazzes me up. And so it's kind of really getting into. Getting deep into those activities. And so one of the first things that I'll have my clients.