Career Coaching Secrets

Master Career Transitions and Leadership with Jacob Lehman

• Davis Nguyen

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In this episode of Career Coaching Secrets, we’re joined by Jacob Lehman, an accomplished career strategist and leadership development expert with a proven track record of helping professionals navigate complex career transitions and achieve lasting success. Drawing from his extensive experience in coaching high-performing individuals and leading impactful organizational development initiatives, Jacob shares a wealth of practical insights on how to thrive in today’s evolving job market. From building a standout professional brand to cultivating strong leadership skills and making confident, strategic career moves, Jacob offers guidance that is both inspiring and immediately actionable. Whether you're seeking clarity in your next career step or aiming to elevate your leadership potential, this conversation is packed with valuable takeaways.

You can find him on:
https://www.linkedin.com/in/jacobklehman/


You can also watch this podcast on YouTube at:
https://www.youtube.com/@CareerCoachingSecrets

If you are a career coach looking to grow your business you can find out more about Purple Circle at http://joinpurplecircle.com

Get Exclusive Access to Our In-Depth Analysis of 71 Successful Career Coaches, Learn exactly what worked (and what didn't) in the career coaching industry in 2024: https://joinpurplecircle.com/white-paper-replay

Jacob Lehman:

On the consulting side, I would say it could be leveling up, kind of getting a promotion, switching firms, something like that. Outside of consulting, it's more what I would think of as career pivoters. So people who've said, you know, I've built a career in this one space, but I'm looking for something different. Whatever reason, I'm not satisfied with where I am. I want to try and move, but I need a little help to get there. It's going to be a little less traditional than just send out applications or talk to recruiters who might be seeking exactly that background already.

Davis Nguyen:

Welcome to Career Coaching Secrets, the podcast where we talk with successful career coaches on how they built their success and the hard lessons they learned along the way. My name is Davis Nguyen, and I'm the founder of Purple Circle, where we help career coaches scale their business to seven and eight figures without burning out. Before Purple Circle, I started and scaled several seven and eight figure career coaching businesses myself and consulted with two career coaching businesses that are now doing over $100 million each. Whether you're an established coach or just building your practice for the first time, you'll discover the secrets to elevating your coaching business.

Rexhen Doda:

Hey everyone, welcome to another episode of Career Coaching Sequence Podcast. I'm your host, Regan, and today's guest is Jacob Lehman, a trusted advisor to leadership, former McKinsey consultants, startup mentor, and investor. With a unique blend of legal training, consulting acumen, and a deep commitment to help to human development, Jacob has helped everyone from Fortune 500 giants to scrappy startup navigate, growth strategy, and people decisions. He's also a stage combat instructor and five-time crossword competition champion. So yes, he's the rare mix of sharp mind, strategic heart and creative soul. It's my pleasure to have you on the podcast. Welcome to the show, Jacob. Thank you, Regin. Pleasure to be here. Tell me a little bit more about what inspired you to become a coach. I know you have many occupations, so you can talk about those as well. But I'm mostly interested on the coaching side of it.

Jacob Lehman:

So I started out going to law school immediately after undergrad, spent my second summer with a large law firm, realized I didn't want to do that. And the next sort of logical opportunity available to me then was to join McKinsey as a consultant. I went into that not knowing a lot about consulting and learning a lot as I went. Post-McKinsey, I had a couple of roles in corporate strategy. And then in 2015, I came to work with Cornell's MBA program, helping aspiring consultants get jobs at top consulting. So that's really where it started, was working with MBA students who in many cases were trying to pivot and explore. It started out with how do they get jobs at those firms? And that really sparked my interest more broadly in how do people make career decisions? How do they find the right role for themselves? How do they pitch themselves effectively for something that may not align sort of traditionally with their background? And that's really been my focus ever since is how do I help align talent with opportunities?

Rexhen Doda:

Cool. And how long has it been? How does your journey look like from like when you started doing this or let's say when you started doing this on the side to where you are at today?

Jacob Lehman:

So I first started working with coaching clients independently around 2020. So it's been about five years now and continued to spread. It started mostly with folks trying to go into or out of consulting, the spaces that I knew best. And then, you know, as you get to know more people, getting involved in the startup ecosystem, I had to do an executive search to sort of learn more about different roles and find more ways to be helpful.

Rexhen Doda:

You did mention that when you started working at Cornell, you were also helping people get jobs in consulting. But is there a specific group of people or target audience that you're usually working with as a coach? Or is there not

Jacob Lehman:

a specific target? Probably 50% still folks trying to get into consulting. consulting in one fashion or another, and then the other 50%. People, I would say, generally trying to do an, quote, unconventional search. I think that's really where my strength is in helping people tell the story, helping them identify areas that might be good opportunities for them that aren't just, you know, get a promotion, do kind of more of the same of what you've been doing.

Rexhen Doda:

So basically, your focus is on people who are already working or want to get the job in consulting?

Jacob Lehman:

Either. On the consulting side, I would say it could be leveling up, kind of getting a promotion, switching firms, something like that. Outside of consulting, it's more what I would think of as career pivoters. So people who've said, I've built a career in this one space, but I'm looking for something different. Whatever reason, I'm not satisfied with where I am. I want to try and move, but I need a little help to get there. It's going to be a little less traditional than just send out applications or talk to recruiters who might be seeking exactly that background already.

Rexhen Doda:

And we were talking earlier a little bit about how you kind of like find your clients or how clients find you. Could you share more about how you go about lead generation?

Jacob Lehman:

Yeah, so I'm active in alumni networks for Cornell and University of Michigan. So I get some folks there. I'm fortunate to get a decent number of referrals from people. And then as you alluded to, I do consulting work for clients as well on the corporate side, mostly focused on corporate strategy. And that's often been an area where we like the way we think, myself and a client, and then it becomes a network where either they know of somebody who is going through a transition and might need a little help, or they themselves following a project may we are thinking about alternatives and we can keep the relationship going that way.

Rexhen Doda:

And just for my curiosity, because I also have experience working in the field, is Cornell considered like a target school for consulting firms?

Jacob Lehman:

Yeah, the risk of claiming too much credit. You know, when I joined the MBA Career Center, we were sending about 15 students per year to McKinsey, Bain and BCG. And when I left, we were sending 50 plus per year. So we got to kind of parity with our peer schools during that time.

Rexhen Doda:

Wow, that's quite an achievement. And thanks for sharing. that. So right now, where is your focus mostly? And do you have any goals that you are working towards for the next one to three years, either with your coaching business or other initiatives that you'd like to share?

Jacob Lehman:

Sure. I'm always looking for ways that I can do more, share more ideas. So I started a sub stack about a year ago called Intellectual Odyssey, where I post reflections on a lot of different topics. And in many cases, they do tie back to career questions as well, because that's something that I spend a lot of time thinking about. So I'm hoping to increase kind of the reach and efficacy of the things that I write, the content that I'm producing, as well as continuing to find more, really, I would say more long-term clients. It's fun to help somebody land a job immediately, but a lot of the most rewarding relationships that I've built have been situations where I may have worked with someone now when they were an MBA student back nine years ago, and then we catch up a few years later when they're thinking about leaving a consulting firm they joined then. Now maybe we're talking because they're thinking about going and doing a startup and wondering if a team they could bring in or other things and seeing that evolution of someone's journey is really exciting. So hoping to do more of those.

Rexhen Doda:

Wow. So basically you're working with them throughout different stages of their life, right? Actually, when they're also thinking of exiting opportunities from consulting too, that's very like, it's so cool to be able to have that and people actually still keep the connection with you. And that just shows how much value they've gotten from you and your coaching perspective as well. So when it comes to an Another question I wanted to ask you is when it comes to investments, has there been any investment in helping you grow your coaching business? And by that examples I can think of is either like masterminds, coaching programs or communities or anything really that maybe investments on yourself that you feel that have made a difference for in terms of you growing your coaching business, even though it's on the side.

Jacob Lehman:

Yeah, so about two years ago, I participated in a mentorship training program through a group called the Portfolio Collective. That was really really helpful just working with a bunch of other independent professionals, understanding the leadership challenges they were working with people on and learning a little bit more about the specific kind of funding cycle for really early stage startups. It was just a different perspective to have. On the more operational side, I bit the bullet last year and started paying for a CRM. So I'm using Pipedrive probably not as well or as actively as I should, but it helps for the conversation where it's just not the right time, right? You feel like it's a good fit. There's potential here, but somebody has just made it. a move maybe and they're not going to look to leave for a little while later. I no longer need to worry personally that I'm trying to hold all of that in my head of when am I going to reach back out to this person. I can just kind of make a note and come back to it later.

Rexhen Doda:

Nice. Yeah, we actually have had that similar case also. So we moved into a similar platform to Pipedrive. Pipedrive is called Go High Level in our case that we're using. And yeah, it's been very helpful for us. So yeah, great tool to have like a CRM that can help you keep track of all of the relationships, especially when the time is not right for them to cultivate. And later on, yeah, they might even appreciate that you're actually getting back to them after so long. Yeah, it shows like an extra human touch there. I also wanted to ask you, and I also do ask this to other coaches as well. Is there something that you wish you had known when you first started growing your coaching business that was like unexpected lesson learned or even expected

Jacob Lehman:

maybe? So two, I think, really interesting insights that kind of emerged for me. One is recognizing how people's goals in the job search and the pressure they feel is not always individually driven, especially earlier stage. People may have parental pressure or friends have opinions, and that can create a lot of limitation in what they're looking at. They say, I only want X opportunity or Y opportunity. And trying to hear that and respect that, but also find the space to examine it and say, well, what really are your goals? And sometimes it really is tied to a particular brand name, right? I may have had a lifelong fascination with Ferrari as a company, and I just think working there would be the coolest thing ever. But it's personally driven, and I will continue to get extra normal satisfaction from working for them beyond the compensation on other things, no matter what. A lot of times, though, it's the momentary thing, right? It's you got an offer from, use my own employer, McKinsey, and people go, wow, for a minute. But if it's not driven from me, that has a very short half-life, and that satisfaction... So helping people unpack that and really understand what are you looking for and then where are those opportunities that will scratch the itches that you really have that will address what you are really solving for so that you're set up for long-term success and satisfaction there because every job is going to have its frustrations and you'll get through those better the more committed you are to the work. The other piece is recognizing that every individual is unique, right? Your goals aren't the same as mine. Your strengths aren't the same as mine. And so if I tell you, oh, in order to get your next role, You should go to a bunch of conferences and network with lots of people, but you're a very introverted person and you're not that comfortable. That may not be effective. It's just going to be frustrating. It's going to take a lot of energy and time away from the things that would let you shine. At the same time, if I'm telling you to do something that I wouldn't do myself, there's the risk of a credibility gap. So I want to be able to articulate why I think that's the right strategy for you, where I can say, look, based on what you've described, you don't need to script out all of your stories. You're a good storyteller. You've got that down. It'll feel more natural if you you can just go and show that to yourself. I scripted them out because I felt like I needed to do that to feel fully prepared. And owning and acknowledging those differences and what I might do personally from what I think is right for you can help lead to a really fruitful conversation. The third piece, the last one I'll say is sometimes I think my job is to tap the brakes, right? Especially when somebody gets an offer. If they've been going through a search for a while, it's really exciting. They can feel a huge amount of momentum kind of to just say yes. And And being able to take them back to that original list of, okay, well, what were your objectives? Is this really meeting, not necessarily every single one of them, because very few things will, but enough of them that you can be confident this is the right move for you and tap the brakes, slow it down a little bit and see where does this really make sense? And if it doesn't, but they don't have another offer in hand, part of the journey that I build towards with folks is balancing the immediate kind of, everybody wants to find a job quickly. Nobody wants to take longer than it needs to, especially if you're you've got financial urgency associated with it. But hopefully you've been balancing the applications and outreach to immediate opportunities and sort of the longer term skill building, storytelling, relationship building that will pay off for years to come. Because you had an interesting conversation with somebody now and five years from now is when that really comes to fruition. So that helps with that pushback. If we can say, well, look, you planted a lot of seeds a month ago and great that this one is coming up, but if it's not the best opportunity yet, maybe it's worth checking in on some of those other seeds if they are starting to bear fruit or if this really is the only option.

Rexhen Doda:

Interesting. So basically removing that emotional fog that is created by just getting that opportunity and giving them clarity and like thinking like objectively as opposed to obviously in your case, it's easier. So you're able to give them your perspective. That's so interesting. What would you say are some of the biggest challenges you faced with your coaching business, even though doing it on site? I know we talked a little bit about earlier, and your focus is also on other initiatives. But what would you say is the biggest challenge, even from the business perspective, but also from the coach's perspective, as you as a coach?

Jacob Lehman:

Well, the working world is changing rapidly all the time. And especially in different sub segments of it, you'll see different things we've seen, you know, first, it was reviewing kind of recorded interviews, then it's, you know, AI services doing screen calls and things like that. And so there's just a lot to stay on top of, but your clients expect it. They want you to know what's going on. They have questions about what AI may mean for these roles they're thinking about pivoting into or out of or where they're looking at going. You know, it's a challenge. I think all you can do is kind of keep an open mind and be humble about it and really try to read as much and learn as much as you can about what's going on and speak to those things. That's an area where actually being involved as a consultant has been really helpful for me too, because I can speak to the challenges that I see clients facing within their own organizations. It's a small sample size, may not be fully representative, but it gives me a little bit of a different perspective to say, okay, you're thinking about going into working for a company in the HR tech space. Here's what a client I'm working with is dealing with. Are you sure that's the direction you want to go? Or here are some things that you might want to study up on to be prepared for interviews in that sector.

Rexhen Doda:

Interesting. So that is basically the unfair advantage that you have because you have that knowledge from other people that you work with and you can give them an extra perspective. And again, kind of like removes their emotional thought. So, yeah,

Jacob Lehman:

you know, within the bounds of client confidentiality and those things, but just giving them a little bit of a perspective of the job search is always or almost always the number one priority for the person who's going through it. And from the perspective of an employer, sometimes it's the number one priority, but oftentimes it's like number two or three compared to the other things that they're thinking about. So giving them a little bit of that perspective and helping them understand what can you speak to? What are problems that are keeping them up where you can say, look, yes, you're you thought you needed to fill this role, but I can actually help you solve the big hairy problem on your mind. You know, that's in a lot of cases where they get really excited about a

Rexhen Doda:

candidate. Interesting. That's a completely different perspective. So thinking beyond just the role and like the high and cross, but also like being creative, maybe even changing the role that they're looking for. That's something I haven't thought about before. So quite interesting. Thank you for sharing that, Jacob. And we're going to that final question, which is like, what advice would you give to other coaches who are looking to scale their And this would be like the advice would give to yourself if you were looking to scale your coaching business.

Jacob Lehman:

I mean, coaching is heavily personal. It's an individual's journey and what you can bring out in them. So I think just spending a lot of time really reflecting on what have been your own priorities and motivations. How do those differ from other people in your life, your spouse, your siblings, your parents, you know, to really kind of get those perspectives and sit necessarily in judgment, but help them people understand where are they solving for, what are they solving for, how does that change what success looks like for them becomes a differentiator and helps you find that fit with more people who may have a different perspective than you. For me, I have two siblings, so it's very easy for me to think about, okay, this person reminds me of my sister, this person reminds me of my brother, and I know that I would speak to them differently than I might speak to myself to get the message across.

Rexhen Doda:

Thank you. Thanks so much, Jacob. It's been lovely having you on the podcast. For anyone who wants to connect with you or reach out to you, they can find you on your LinkedIn at Jacob Lehman. And basically we'll be able to reach out to you there. You also have your email and phone number within LinkedIn. So is there any other way people could reach out to you? Those are best. Thank you. Thank you so much, Jacob.

Davis Nguyen:

That's it for this episode of Career Coaching Secrets. If you enjoyed this conversation, you can subscribe to YouTube, Spotify, Apple Podcasts, or wherever you're listening to this episode to catch future episodes. This conversation was brought to you by Purple Circle, where we help career coaches scale their business to seven and eight figures without burning out. To learn more about Purple Circle, our community, and how we can help you grow your business,