Author and Expert Dan Freehling on Leadership and Career Coaching for Millennials

Today, we’re talking with author Dan Freehling. Dan is a leadership and career coach who has really compelling ideas around career planning, - especially for millennials. He is the author of the recently released book The Career Design Map.  Let’s dive in. Visit his site at contempusleadership.com

Clinton Henry: Dan, I'm so excited that you're here for a multitude of reasons. The first is you get to finally settle a debate between my wife and me. What is a millennial? What's the age cut off? Who's an elder millennial versus a xennial? How do you view it?

Dan Freehling: It's such a great question and the definitions are all over the place. I basically see it as anyone currently in their late 20s to early 40s. So about 27, 28 to somewhere around 42 or 43. I think the exact age cutoff is less important than that general generational zeitgeist that comes along with it.

Clinton Henry: That's really a smart way of looking at it. Thank you. That's wide enough to where my wife wins the argument, I think just fine. So in your book, congratulations on publishing, by the way.

Dan Freehling: Thank you.

Clinton Henry: You make the argument that old school career advice no longer works. What is old school career advice and why is it no longer effective?

Dan Freehling: Yeah, thanks for that. It's such a great question. I think how I define old school career advice is this linear approach to career that was really designed to work well in the industrial era. So this idea that you would understand what schools you should go to, what types of careers you should enter, and your main job was to fit in slot in to pre-existing jobs, pre-existing career paths, keep your head down, follow those. That was the way to win in career. It was basically how can I fit into the industrial era working world? I think we're at the late stages of a transition into this next era. So this innovation era, knowledge economy, passion economy, it goes by a number of different names. I think it's all getting at the same thing, which is you're now tasked with figuring out something that's both highly adaptable. You have to be ready to change, adapt, continuously, learn, experiment, grow, and at the same time highly personal. You have to be doing differentiated work that's uniquely you, that's purpose driven, that's meaningful. Because you're no longer in this economy where conformity is rewarded. You're in an economy where unique differentiation is rewarded more and more, and the sort of low hanging fruit benefits of maximizing output and minimizing anything that's going to get in the way of that output is waning. I think this new economy is what can we create, what can we build, how can we have relationships, all of these new ways of looking at work. So that's the difference I see in it.

Clinton Henry: So how should millennials think about career and leadership development if they're not going to have that old mindset?

Dan Freehling: Yeah. That's the crux of my book, is this strategic way of thinking about it. I have a lot of coaching clients who are millennials. They're getting into managerial senior specialist, director, VP, even founder type positions. And what they always run into is basically, I know I have to be ready to change. I have to be ready to adapt, but at the same time I want to be intentional and purposeful. What I did was put together this framework called the career design map. And it's a way, instead of looking at what specific jobs should I be looking at doing, what specific career paths should I be looking at doing? Because we know that five years out, ten years out, things will likely be changed and the job might not even exist that you're looking to do or it might change in such a fundamental way that this pulls back and looks at it a more strategic level of what type of meaningful work do I want to be doing? I can get into the for meaningful career types. Then also equally importantly, what type of dangerous seas I call them, do you want to avoid and think looking at both of those in a really high level strategic way is helpful in giving people a framework, giving people a grounding in a really confusing era of career and leadership development.

Clinton Henry: Yes. Let's hit both of those. Can you kind of walk through the meaningful four career types there are?

Dan Freehling: Absolutely. So there's the contributor, the go getter, the expert and the executive. Just pulling back overall the career design map basically has an X-axis and a Y-axis, and X-axis is career advancement. So starting over on the way left hand side of the graph, you'll have too little career advancement. And then on the way right, you'll have too much like when you're experiencing everyone around you saying how great you are all the time. So basically for the meaningful for the contributor is the type of person who enjoys their job. They contribute to the team, they show up, they do a good job, but other areas of their life are more important to them. The go getter is higher up on their leadership. So they're both in that lower to mid level of career advancement, but they're much higher on the leadership axis. And the go getter is basically leading above what would be expected of their level. So this is the kind of person who's really going above and beyond day in, day out on the team. They're the up-and-comer. They're that go getter. The expert is further to the right. It's higher on career advancement, but lower on that leadership. So this is someone who's has a strong career. They make a lot of money. They're highly valued at their organization or even as a freelancer or as their own entrepreneurship venture. But they're not focused on leading others so much as they're focused on being an individual contributor in a very strong way. And then the executive is the pinnacle of the career design map. It's both well advanced in career and well advanced in leadership, but not to these extreme levels that we'll get into in a moment. And the executive is really where people can make their greatest impact. You're leading is a sustainable clip. Your career is advanced to a degree where you're really accomplished, where people respect you, where you're able to bring people together, get things done, but you're not in this arrogant bubble as well. So that the executive is really the pinnacle of this map.

Clinton Henry: Gotcha. And you mentioned briefly the dangerous seas. Can you just briefly touch on what those are?

Dan Freehling: Absolutely. Those are invisibility. This is the one that is the extreme low end of career advancement. This is when no one is noticing you, when you're not able to express what you do uniquely well, when people are not listening to you. I think a lot of people in long term job search unemployment modes find themselves in this invisibility camp, and it's basically that career axis is defined as confidence in yourself and from relevant others. So it's when you're too low in self confidence to really put yourself out there and at the same time, those around you are not really understanding why they should bring you onto their team, why you should be a part of their organization. On the other end, the other extreme of career advancement is what I call arrogance. So this is another dangerous see and it's kind of counterintuitive, but you're actually too advanced in your confidence in yourself and from other people around you to a degree where it makes it really, really hard to welcome in new ideas to get honest feedback. You're surrounded by yes People. That's a really dangerous sea to find yourself in. The other dangerous sea is so too low on leadership. So that's the y axis of the graph. Too low on leadership is what I call disengagement. So there's these Gallup statistics that are out there on the level of disengagement in the workforce, and they're always shocking. They're always 60 something percent of US workers are actively disengaged in the workplace. This is when there's too little leadership. And by leadership, I mean enabling others to achieve a common purpose. So you're just disengaged, you're pulled back from finding meaning and purpose in your work and helping your team succeed. And that's that disengagement one too high on leadership. The other extreme is what I call burnout. And it's when you're basically shouldering the responsibilities of your organization, of your team on yourself in a really unsustainable way. And that's leading to you feeling like you're personally responsible for saving the organization, saving your team. And that's what I think leads to this burnout epidemic that we're facing as well.

Clinton Henry: That's fascinating. Yeah, the Gallup Q12 is always interesting to look at.

Dan Freehling: Absolutely.

Clinton Henry: And the level of engagement levels throughout organizations. And then when people make changes, how drastically an engagement levels of your talent can change as well. So that's really interesting.

Dan Freehling: Spot on.

Clinton Henry: Do you have advice for millennials on how you can act with purpose and be adaptable in your career planning?

Dan Freehling: I think that's exactly the crux of this crater design map. So it's basically doing this ongoing deep work of figuring out what drives you, what impact do you want to make in the world, what gives you meaning, what gives you purpose? I really like to focus on that impact portion of it as well, because there's so much of this self-help advice out there that's very sort of self centered. That's like, I want to do this. That's I'm passionate about it, so I'm going to do it for me. And that part of it's important, but I think it's even more important to have a purpose that also has an impact on others. And it's something that you obviously grow and develop and refine over time. But it really requires you trying things out, taking on different types of roles, working with mentors, coaches, sponsors, trusted family and friends in your life, just all kinds of people to really get honest feedback along the way figuring out where your unique strengths and gifts lie and then how you can maximize those also stretching out of those so you're not just continuously in the same sort of cycles. So that's the meaning and purpose piece. I think it combines really well with the adaptability piece of again this experimentation, this continuous learning, this continuous growth. I think to thrive in this emerging economy that we're going into this innovation economy, this knowledge economy, that you need to be doing both that deeply you, deeply human, deeply personal work and that deeply adaptable work as well.

Clinton Henry: When I was going through some of the literature around stuff you produced, the one thing that kept coming to mind was brand. And I think people didn't talk about their brand 15 years ago, and now you are your brand and you own your brand. Do you talk to people? The people that you coach about being strategic, about the efforts that you have within the work environment to bolster your brand. So if you want to be an executive, don't do the things that make you an expert, really do the things that sell you as an executive. Does that ever come up or people just kind of flailing and being not strategic and just trying to do too many things?

Dan Freehling: I think it's such a great point. I really do think the branding is critical. I think that branding in a non trivial way, that branding in a non sort of performative way is a lot of where I see my clients going and needing to go is it's less of like I'm going to be a TikTok influencer or something, or I'm going to have this sort of shiny brand that doesn't have any real depth or meaning to it. It's really that brand in the sense of that career development axis, that having that confidence in yourself, having a clear message of what type of work you're aiming to do, what value you bring to it, and then building that confidence of other people being so key. So I definitely think that branding, but in a real, genuine, authentic way is going to be key. And especially as AI automation, all of these other new technologies start to really take off. I think it's going to be more imperative than ever to really have a brand that's deeply you and deeply human and not something that's easily replicable or easily replaceable with any of these new technologies.

Clinton Henry: Yeah, I think being unreplaceable and unanswerable is critical and having a strong brand is part of that. The reason I know that so well is because I made that same mistake. I had a coaching conversation with one of my mentors and I was talking about like, Oh, I just don't feel like I'm doing all these things, but I'm not getting noticed. And he asked [] a question. He's like, well what do you want to be? You want to be this type of leader or this type of person? And he basically said two different people with both executives, both strong leaders. But one was very technical and one was more of like a people leader. And I'm like, oh, I want to be that one. He's like, well all the stuff you're doing is is not strategic. You're just kind of []. So having a plan, a goal and then working towards that is massively important. I'm so happy that that I wasn't the only one and that there are other people that make that mistake. What other mistakes are people making in their career strategy that you see from a coaching perspective?

Dan Freehling: That's huge. Thanks for sharing that, first of all. I couldn't agree more. I think a lot of coaching really boils down to what do you really want? And helping people to articulate that and then providing the relevant framing and helping them to come up with their own next steps of how they want to achieve that. I think that's really great. Other mistakes that I see people seeing, one that's very recently coming to mind is I have a career design quiz that's part of this book. So it's a careerdesignquiz.com. It's a companion to the the book and the framework. It can be really helpful. I've seen a lot of people who would get their current state as a go getter. So they were in that leading above what would be expected of their level and then getting their future state, their desired state, as arrogant. I was wondering if there was something going on with the quiz for a bit and I refined this quiz over a year now of really honing it in and running people through it and changing it around and all of that. It happened a few times recently and I realized that there is this mistake that people are making now, where they're just going full on into being driven and they're going full out and they're more and more and more and more is always better. The hustle and grind kind of a mindset. What I think that leads to is a lot of what you were experiencing when you were talking with your mentor and getting those coaching conversations is this sort of idea that you're throwing everything at everything you have at career advancement and trying to just be the best and be an executive and be this higher level without having that really strategic. Like what do you actually want and what lifestyle do you want? What work environment do you want? What impact do you want to make? What do you find meaningful? How do you want to contribute to that? And giving some of that thought rather than that sort of just straight climber mentality, that's straight ambition mentality is really critical. I think on the flip side of that, there's also this quiet quitting phenomenon that is seemingly popular. I'm not sure how popular it actually is in practice, but it seems like it's a social media trend largely. And I think that's also equally damaging and dangerous to buy into this idea that you're going to do sort of the bare minimum and that everyone is out to get you and companies are out to get you, and you have to just really protect your own time and not put yourself out there and not do that. I think that's sort of a flip side of this hustle and grind, this achiever mindset is this sort of quiet, quitting, disengaged, what have you mentality. I think it's just key, both in my coaching and in the career design map of striking that balance that works for you. It's not going to be the same for everyone, but really finding out what do I really want and how can I strategically go after that?

Clinton Henry: That's great. Yeah, I've been in leadership for almost 15 years and I can tell you that they call it quiet quitting now, but it's been around for a long time. It boils down to disengagement. And just not engage and that's really about not being aligned with like having autonomy, mastery, purpose aligned to your work and just being focused on something else. So from a leadership perspective, a lot of listeners here are leaders. They lead millennials. I remember millennials are the worst generation. This is the worst. And now it's the worst. Everybody is the worst generation. What advice do you have for leaders on how to engage with millennials if they have like you said, the late 20s or early 40 seconds, that's a significant portion of the entire workforce. So do you have specific coaching or advice for leaders who have a lot of millennials on their team?

Dan Freehling: Yeah, you're so right. It's a huge chunk of the workforce. It's over 35%. So I think this this sort of idea of these are a terrible generation that can't work with. That's just a non-starter. You can't not work with a third of your generation, a third of your entire workforce generationally and similarly to the Gen Z, you can't also dismiss an entire incoming generation in the workforce. I think what it really comes down to for working with millennials is realizing that age range and career range is now getting them into manager, director, VP, high level leadership positions. Some are in executive roles, but I think it's really working in partnership with them and not trying to fix them, not trying to be condescending or patronizing to them, but really working in a partnership capacity with these leaders and realizing that they're very purpose driven. I think that's the key of understanding. The millennial drive is this real desire for purpose and meaning. And it's something where there's going to be all different working styles across generations and there's different people within a generation that have different working styles. But I think if you can tap into that true partnership and ensuring that the work is actually genuinely meaningful and purposeful, you have an unbelievable generation of leaders to help move your organization forward and advance your mission and purpose as an organization.

Clinton Henry: Yeah, I couldn't agree more. That's a wonderful thought and I think a great spot to end it.