Mentorship used to be the career cheat code. Now it's a form you fill out in Q1 and forget by March. Ryan and Daniel dig into why the mentorship inside most companies stopped working, why the version that happens organically still does, and whether an AI chatbot can do any of it.

Spoiler: it can help you write the email. It cannot notice that you already tried the thing you're about to try again.

In this episode:

• Mentor, coach, or sponsor — three different jobs everyone keeps calling the same thing
• Why the people best suited to mentor almost never volunteer for the program
• The phone book story: how technology turned a mentorship into an insult
• What ChatGPT actually did well when Ryan ran a real workplace conflict through it, and where it fell flat
• Why remote work quietly killed the hallway mentorship nobody scheduled
• How to ask someone to mentor you in a way they'll say yes to

00:00 — AI Mentorship Is Fast Food

02:00 — Broken, Evolving, or Both?

07:00 — Mentor, Coach, Sponsor: Nobody Agrees

13:00 — 76% Want It. 37% Get It.

17:00 — Blind Dates and Free College Credits

21:00 — The Guy Who Ripped the Phone Book in Half

27:00 — Can ChatGPT Mentor You?

33:00 — Zoom Killed the Hallway Mentor

38:00 — Vision: Clarity Is the Mentee's Job

43:00 — Journey and Culture: Set the Rules Before the Coffee

48:00 — Results: What a Working Mentorship Looks Like

52:00 — Last Word: There's Always Someone You're Ahead Of

Daniel: AI mentorship is a lot like fast food. It's quick and easy, but at the end, you'll still be hungry for a real meal.

Ryan: That was better than I thought you were gonna say. I thought you were gonna compare it to Taco Bell. Quick and easy, but it doesn't come out fun.

Ryan: Mentorship is a vital component to personal growth, especially in the workplace. If you've got ambition to do great things, grand things, or you want a career that provides a lot of income so you can do things for your family and build a legacy, you're not gonna be able to do it alone.

Ryan: I think what started the rift and the disruption was when the older generation was trying to mentor a younger generation and it just didn't make sense. While you were seeing younger people, especially millennials, getting elevated faster, you're going, "Wait a minute. You're sending proposals sitting at your desk and you're getting the same close rate as the guy driving around town and submitting mileage? I'm gonna make you the sales manager." You're more efficient. It was literally that dynamic, that rift that technology created, where it created a divide even in the mentorship. And then you compound it even further now because you've got AI. Do I bother dealing with a human when I can just prompt ChatGPT and get an answer that's probably more neutral, less emotional, and faster than dealing with a human?

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INTRO

Daniel: Welcome to the Make Work Not Suck podcast. Mentorship used to be considered the ultimate career cheat code, but it seems like today's employees are feeling more and more disconnected. Obviously remote work makes that harder. The disconnect between generations is making it harder. And maybe we don't need mentors anymore because we've got AI bots. So is mentorship in the corporate context broken, or is it just evolving?

Ryan: I think the answer is both. But I'm gonna start with: it's broken more than it's evolving, because that is still one of the legacy paradigms we hang onto today. Not that it should die, but I think we still do mentorship in a very legacy manner and it's not evolving fast enough, which is why it's broken.

Daniel: I think most mentoring programs are a corporate checkbox. Well-intentioned, poorly executed, and very disconnected from the actual needs of the employees.

Ryan: I would definitely say mentorship programs built inside the quote-unquote four walls of a business are definitely broken. Mentorship that happens more organically in society, those are probably still the most valuable growth connections you could make. But those inside the business, especially when you have a small business owner who's grown big enough that they want to be in that mentor seat but they're not good mentors, that is where it is absolutely broken.

Daniel: Absolutely. All right, so let's break this down. Today we're gonna dive into the current state of mentorship. Where's the disconnect? Let's talk about generations and the differences and expectations between the mentors and the mentees. I'm gonna mess that up. At some point I'm gonna call them manatees, and I'm not gonna mean that. It's mentees. Let's talk about remote work and COVID and how that influences mentorship, as well as the whole AI emergence. Do you need a human? Can't you just ask ChatGPT? And then let's land the plane around practical advice for people who either want to mentor or want to be mentored in the world as it exists today. How would you go about doing that in a way that doesn't suck?

Ryan: I like it. Also, I'm gonna give you some bonus points here, because when you were reading that line, I was reading the outline and I read it as Mentos, like the candy.

Daniel: Mentos and manatees.

Ryan: So we'll have Mentos and manatees on this episode. That's a guarantee.

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WHAT MENTORSHIP ACTUALLY IS

Daniel: All right, let's jump in at mentorship. I hear coaching, I hear managing, I hear mentoring. I hear a lot of different words. I don't think anybody really knows what those words mean. In my experience, a lot of the emerging workforce want guidance, they want help, but the words they choose to describe that are very different, and it doesn't seem like anybody's getting what they really need. So I'd love to hear your take. What do you believe mentoring really is?

Ryan: To me, mentoring is when you're helping someone better themselves in their career or their goal without any goal of your own. But too often what we call mentorship today is just telling people how to do something. We think telling them what to do is mentorship, whereas it's helping them get to the conclusion on their own, or giving examples and helping them evolve. It's almost like professional teaching. Like learning math. It's a problem, but instead of having a textbook and a formula, mentorship is more tailored toward the individual and the circumstance. It's something you can't teach out of a book.

Daniel: I would go with a different definition. What you're describing, I would call more of a coach, right? Somebody who is helping you discover your answers to various questions. I've always thought of a mentor as somebody who is currently where I want to be. They have been there, they have done that, and they're giving me advice on how to get to where they are.

Ryan: Okay. Yes, I agree with that. And I see that mentor-coach thing, there are some blurry lines there.

Daniel: There can be some overlap, absolutely. But I always thought of a mentor as somebody who has to be ahead of you. With a coach, think about Tiger Woods. Tiger Woods had a golf coach. The golf coach was not a better golfer than Tiger Woods, but he knew how to coach, he knew how to motivate and analyze his swing. I'm not a golfer, but he had a coach who was clearly not as good a golfer as he was. So he wouldn't call that guy a mentor. Tiger Woods, if he had a mentor, was probably somebody like Jack Nicklaus or some other famous golfer who's won lots of tournaments. So they're probably similar, but I do think a mentor is somebody who has been there, done that in a way that you want to in the future.

Ryan: Okay, by that definition, yes, I totally agree. The mentor is the person who is where you want to be, or they have been where you want to be, and they can share their stories and tell you their experiences and give you insights and help you better yourself to get to that spot.

Daniel: What about your personal experience with mentors? What mentors have you had over the years?

Ryan: It's crazy, because I've had dozens, but I blur the line with coach as well. I guess I can go back to my most foundational one, my business mentor in high school. She was actually my business teacher in a business class, but then she started helping me outside of school on special projects. She literally started mentoring me outside of the program I was in in high school. That's where I learned about the book Seven Habits of Highly Effective People. She handed me that book and said, "You have to read this book." Nobody else in the class was reading the book, but I had to read the book. If you want to be a good business person, you start with reading this book.

Daniel: Wow, that's great. How old were you?

Ryan: Fifteen.

Daniel: Geez, that's fantastic. I didn't find that book until I was 20 or 21. I was well into college by the time I found that book.

Ryan: That should be required reading in high school for everyone.

Daniel: I have a mentor now, but over the course of my career I've certainly had lots of sponsors. Sponsor might be the best word. Somebody who's maybe a level or two above you, who is guiding your career, helping you make those career choices, giving you feedback. Maybe they're inside the company, maybe they're not. There was a guy I worked for for several years who was a very good mentor to me, but more of what I've had has been that sponsor. They're not necessarily where I want to be, but they are ahead of me and they can open doors for me. That's sometimes called a mentor, but I think those are incredibly important, especially in large organizations.

Ryan: I don't have much experience working inside a large organization with a mentor. Typically I was the mentor, or I was brought in to mentor. As far as being mentored inside a business, where I got more mentorship in my later days would be my Vistage group. I'm the younger business executive in the room, and a lot of the guys could be anywhere between 15 and 20 years ahead of me or older than me. Some of these guys, I'm at their level career-wise, but some of them may have been 20 years into it. So there was a lot of peer mentorship. Maybe that's another one. There's a difference between a coaching mentor and a peer mentor.

Daniel: I went to grad school and I got assigned a mentor. He was not in the organization I was working for. I was working for a Fortune 500 company. He was working for a different Fortune 500 company. He was a big deal. We had the same alma mater. He was a general manager at Delta. We never met. We never spoke. We got matched up at something and then we both got busy, and I think I'm still connected to him on LinkedIn. For me, that shines a spotlight on the error of so many of these mentorship programs. They're mandatory fun. It's like being set up on a blind date by somebody who doesn't know you. They go, "Oh, you're gonna love her. She's great, she's beautiful." And you get there and you're like, "What? Why did you think I would like this person?" That's what a lot of corporate mentorship programs look like. They're mixing and matching, and it rarely creates the spark.

Ryan: It's funny, because as you were saying that I was thinking about my son, who's about to go off to college. He joined a mentor program before move-in day. One of the things is he gets a full college credit for doing this one-week program. At the end of the day, what it is, is kids who want to move in early get a free credit. And then any sophomore, junior or senior students who want to earn an extra credit and get some perks out of it. So what are they motivated to do? I'm sure there are young adults going into the program who want to actually be that mentor. But is everybody doing this for the free credit? I can tell you, that's the cheapest credit I'll pay for, because it was only $125 for the program. And I guarantee you I'm paying like four grand a credit hour otherwise.

Daniel: You should see if he can take it twice.

Ryan: But I assume that's very similar to these corporate programs.

Daniel: It is. There's a recent study that came out that showed 76% of employees want to be mentored, but only 37% actually experience it regularly. Some of that comes down to the title, right? Mentoring feels very formal, just using that word. And as you're talking about your son, I'm thinking about my son. He went to a smaller private school and they had buddies. But the buddies were always multiple grades above you. So in fourth grade, my son had a buddy who was in eighth grade, and he was a buddy to a kid in first grade. It set it up as being a peer relationship, but it was clearly not peers. It's a first grader with a fourth grader, a fourth grader with an eighth grader. And so the dynamic worked itself out. I wonder if that's actually a better idea. Maybe you should call them career buddies instead of career mentors, if that would reduce some of the awkwardness.

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THE PEOPLE WHO VOLUNTEER

Ryan: Maybe I'm jumping ahead into the problems here a little bit, but part of the problem is that the people who would make good mentors either don't think they would, or they're too humble, or they lack the confidence. Whereas I actually think you get a lot of people who want to sign up for the mentor program, but it's really to boost their own stats. They want to put it on their resume. They want to say they're a mentor. They do it for more self-serving reasons. If you get into a mentor program and your mentor is just talking about how awesome they are and all the great things they've done, that's not a mentor. That's where it falls apart. Because they're volunteer programs, the people who volunteer, there's a chunk of them doing it for self-righteous reasons. And the people who would make great mentors are probably mentoring people around them organically, but they're not being part of the program. They're not signing up to be a mentor in the program. I think that's part of it being broken.

Daniel: I think the more you want to be a mentor, the least qualified you are to be one.

Ryan: Yes. And look, the only exception I'll make to that rule is, I do think when you get late in life and you hit that age where you're wanting to give back, because everybody hits that life cycle, right? Early in life you just want to be the solo person, prove your worth and that you're capable. Once you clear that hurdle, you get into the stage where you want to do this with people and friends. And then you get to the stage where you want to give back to the younger generation. At that point, I think the majority of them want to do it for the right reasons. Whether they're good at it or not is a different story. But I agree with you that the people below that threshold are probably the least qualified for it.

Daniel: Right. If you're under 50 and want to be a mentor, you're not qualified.

Ryan: Probably.

Daniel: Probably, yeah. Because most people don't get to "I want to give back to the next generation" until they get a little bit older.

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GENERATIONS

Daniel: Speaking of older, let's talk about generations. How do different generations think about mentorship?

Ryan: I think it was a big deal. While less formal, it was a bigger deal for boomers than it has been for Gen X and millennials. This is also where the generational gap comes in, the technology generational gap that we've talked about on several episodes. It's probably a lot harder for a boomer to mentor at least a millennial, probably a Gen X, because of the dynamic of the technological relationship and how far advanced millennials and Gen Z were, even to a degree Gen X. When you go from the boomers back, there was just a way of life that worked. Unless you have a boomer with a high EQ who's capable of bridging that gap, I think boomers mentoring millennials was a disaster. It was the wrong kind of mentorship. That's why millennials got more peer mentorship than they got mentorship from older generations at large, because of that dynamic and change. What I see now is millennials mentoring Gen Z and finding success, but I'm not seeing success with boomers to millennials and Gen Z. What I don't know is where X fits in the middle there. Maybe 50-50. The older Xers are probably closer to the boomers and the younger Xers are probably closer to the millennials. But that generational dynamic is what created the disruption.

Daniel: I wonder if some of it is also just the work experience. Given the pace of change in the world today compared to 50 years ago, people 50 years ago had to pay their dues. You have to stay in this seat for several years before you're ready for a management seat. In the world today, you're seeing people jump roles and jump levels in months, not decades. That's a very different world. If you grew up in a world where everyone had to pay their dues, and you look at this young whippersnapper who wants to get promoted every 18 months, that looks arrogant, entitled. But that's not crazy. Eighteen months is a very long runway for a tech startup. We've seen companies go from not existing to worth billions of dollars in 18 months. So the world has changed. That life experience creates a hugely different set of perceptions and expectations between the generations, which makes the Gen Zs and the Gen Alphas really not interested in the war stories of the older generations. Which probably upsets the older generations, because there's wisdom there, but they're not viewing it that way.

Ryan: No, it didn't stop. But you had another younger generation enter in, where you started seeing this "I didn't have it as a millennial, or it sucked, and I want to help mentor the younger generation." So we kind of saw the wheel be reinvented. And then you compound it even further now because you've got AI. Do I bother dealing with a human when I can just prompt ChatGPT and get an answer that's probably more neutral, less emotional, and faster than dealing with these humans?

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CAN AI MENTOR YOU?

Daniel: So let's go there. Let's go to the AI one. I have been using ChatGPT a lot and I've found it to be a very helpful thought partner as I'm trying to create things or brainstorm things or finalize deliverables. It's good. It's not perfect. I'm surprised how often it loses its place. There'll be a series of five tasks and by task four it's forgotten what task one was. And I'm like, "Hey, aren't we supposed to be doing this?" And it says, "Oh yeah, great memory." I'm like, "Hold on, that's what I'm paying you for, is to remember that." So it's not perfect yet. I would want its advice, but I wouldn't call that a mentor. What about you? You build a mentor bot yet?

Ryan: I've got some good prompts, but I'll give you an example I literally had the other day. There was a heated discussion on an L10, and 24 hours later I got a message from the VP. At the end of the day, a particular individual veered out of their lane. They were a VP of one department and they started veering in and essentially doing an end run for an individual in another department, and they didn't understand that. So they put this message out there. As the person trying to manage the situation, I had to mentor myself. Okay, don't do the emotional thing. The first thing I did was write the angry message, the bitch message. I'm not actually sending that, but I feel better. I got it out. Then I took that and rewrote it. And I got to the point where I thought, I want to try this, because I know what I should do, but I want to see what ChatGPT says. So I went to ChatGPT and said, "I need you to guide me on this situation. Here's the context, here's the detail, here's the back and forth, here's the message that was sent to me, here's my angry message, here's my rewritten message. Walk me through what I should do." I guess that's more coaching than mentorship, but I did ask it to mentor me through the situation. It was actually pretty good.

Ryan: But here's where I think the strength and weakness is. First off, I knew my first response was emotional and I never intended to send it. I knew I needed to write it to get it out. I never hit send. That was lesson number one. If you didn't know that, would you know how to prompt ChatGPT to guide it? I think most people are intelligent enough to say, "I'm frustrated, I need to write this response to my manager." ChatGPT would come back and say, "You should probably not send that." Okay, we'll give it that. But then the reformed one that I wrote, that I sent to it before ChatGPT told me what to say, that stuff I learned from physical mentors, from actual humans. That's where I'm kind of like, would ChatGPT get there? Or is it only because I learned it the old-school way that I'm able to leverage ChatGPT today?

Daniel: As I'm listening to you, I'm wondering if mentorship has historically tried to serve two purposes unconsciously. Purpose one, at least on the surface, what most people think of mentorship as, is: I have difficult decisions to make, or important decisions to make, and I want somebody to give me advice so that I am more successful than I would be on my own. Great. But there is a second component to mentorship that AI is gonna struggle to replicate, and that's the personal connection. It's somebody who cares about you. We talked about, I think in one of the last episodes, whether burnout is more a function of loneliness than it is a function of hours. One of the great things about a real human mentor is that when it works, when you've got a good mentor and you're a good mentee, or mento, or manatee, they actually care about you. And they lovingly challenge you. I had a mentor once who, I was telling him where I wanted to go, and he said, "Well, why do you want that?" And I said, "Well, this, this and this." And he said, "Yeah, but you had that over here and you didn't like it. So why are you going after it now?" And I'm like, dang it, he's right. Because he'd listened, he'd paid attention, he knew my story. ChatGPT is never gonna get that. Sure, maybe for some of the corporate advice, how do you navigate corporate politics, ChatGPT would be a good input. But it's never going to scratch that loneliness itch that a good mentor, not a crappy mentor but a good mentor, can do for you.

Ryan: I absolutely agree. What ChatGPT is gonna do is come back with a series of intellectual questions that you're gonna have to use your neocortex to answer, which gets you even more robotic. You need to have a little bit of emotion in some of these things. Not an amount of emotion that's negative, not toxic emotion, but that positive or just-enough emotion in a situation is what makes it human.

Daniel: I might even disagree with you and say even the toxic emotion is telling you something. You need to have a safe person or a safe place where you can let that out, and they won't scold you or fire you for it, but you process that. And I don't think ChatGPT is that thing.

Ryan: I agree with that. Having the mentor be the sounding board who can actually understand it, agree. I was talking about writing the reply, the actual situation. ChatGPT is gonna be all IQ and you're gonna remove the human element from it, which is only gonna make the other person think you're fake, or it's obvious you used ChatGPT. Whereas you're right, ChatGPT cannot be your emotional support buddy, where a good mentor will listen to you even though they know you're venting. They understand the value of getting it out so that they can actually help you. I don't think ChatGPT is gonna do that. It's just gonna say, "I'm sorry you're frustrated. Let's craft a response that's appropriate to the situation." And you're gonna be like, "Fuck you, I just wanna bitch. And then we'll write that."

Daniel: Right, absolutely. Ooh, I love this. AI mentorship is a lot like fast food. It's quick and easy, but at the end, you'll still be hungry for a real meal.

Ryan: That was better than I thought you were gonna say. I thought you were gonna compare it to Taco Bell. Quick and easy, but it doesn't come out fun.

Daniel: That might also be true. So I would land the AI section here by saying: if you know the problem, and you are very confident that you have correctly framed the problem, and you are looking for a solution, certainly consult your favorite AI agent to be part of that solution crafting. Not the only part, not 100%, but an input to it. But I would warn myself and everybody else listening that most of the time we don't frame the problem correctly. Having a real human listen to you and play back what you're saying — I have yet to find the AI agent that's able to do that as effectively as a good friend, and to care and to listen and to push back a little bit where appropriate. If you are at all uncertain about what's going on, or if you're in an emotional state, don't go to your browser, go to a mentor. That is a much better first step. I don't think AI is gonna be able to replace human mentorship. I think it can supplement it, but it doesn't solve the EQ dimension.

Ryan: I agree. And I would say, when you're looking for someone, find somebody who is where you want to be or has been there. Don't find the first person who volunteers to be the mentor. That may be a phenomenal individual, and maybe that is the right solution. It all depends on the context. But sometimes the person who is least qualified on paper to be the mentor has the street smarts instead of the book smarts. The person who's got the most street smarts in what you're trying to solve is often the best mentor. If you can find that person in the situation you're in, you might find much better realistic advice than anything else.

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REMOTE WORK

Daniel: How has COVID, and the growth of remote work, impacted mentorship?

Ryan: I think it's only screwed it up, because it was a lot easier to have organic mentorship inside of an office versus everybody working remote. Mentorship over Zoom is much harder than mentorship over a cup of coffee at Starbucks or a taco at a taco shop.

Daniel: I think it's a lot like long-distance dating. It only works if both sides are really committed to it, and it usually works best when there's some in-person history at the beginning. It's easier to sustain mentorship in a remote context if you had worked together face to face previously. But starting that way and growing it is tough unless both people are really, really committed to it.

Ryan: Agree. I think that's part of the reason we're seeing return-to-work mandates. All those things that just happened organically are ten times more difficult to do, and it's easier for a corporation to mandate everybody come back to the office than it is to try to solve the evolution problem. The evolution of what work looks like in a hybrid or remote environment.

Ryan: And I can tell you, as a guy who runs multiple remote companies, more of the mentorship happens in person, when we fly to the same city and meet face to face. Pretty much every company I work with is remote or hybrid. There's a handful that are full office, but for the most part there's some level of remote. Getting people in the same room is always what moves the needle forward from a mentor perspective.

Daniel: It's just really hard to feel like somebody cares, even if they really do. It's hard to feel like they care over Zoom.

Ryan: This goes back to the lonely conversation. You said it a minute ago. Why are people disengaged? Because they're lonely. It's hard to have a mentor who can empathize when it's a Zoom meeting.

Daniel: Right. It's just hard to care.

Ryan: Hard to show.

Daniel: It's hard to connect.

Ryan: Hard to connect, hard to show.

Daniel: And it feels like I'm on the clock. Even if you and I were to both take our cameras to a couch and sit down and have a cup of coffee, it still feels time-boxed. Unlike if we were actually together in a Starbucks or something like that.

Ryan: There's something to be said about breathing the same air, being in the same room, feeling the same temperature. Sometimes some people need a hug, and just the hug, or a handshake, or a high five. It doesn't have to always be a hug, but sometimes that human-to-human connection brings that level of empathy at an exponential point. It's like, "Oh, Daniel, it looks like you need a hug. I'm sorry."

Daniel: That just makes it worse.

Ryan: Yeah, it does. It makes it so much worse.

Daniel: So then you have to hold back. I don't want to say anything, because I don't want to make it worse, and then I can't actually do anything. So I hold back. Just figure out a way to get face to face with somebody. You are absolutely right. When I was running a new product launch, my team was in Atlanta, but we worked very closely with a team in New Zealand. We spent a year, year and a half trying to work together. They were great people, but it was just not working. It wasn't until the end of the project that I got on an airplane, flew to New Zealand and spent a week with them. And I thought, oh my gosh, why did I not do that at the very beginning? We would have been so much faster if we had just gotten together, had dinner, gotten to know each other a little bit. I will never do that again, because I know I wasted months of my life working through the bumps that come along the road when you haven't built a relationship face to face. Even as good as Zoom and everything else is, there is no replacing that. If you're starting a relationship, you've got to get face to face. If it's an important relationship, you've got to get face to face as quickly as possible. That one's a free piece of advice. It has nothing to do with mentorship, but I think it's very true.

Ryan: I think it's very true. And I started thinking back with every company I work with right now, every company I own or sit on the board of. There are like 20, 23 companies in that list right now. That is why I'm constantly traveling. All of those, I'm face to face. Even companies in California I work with. I remember getting on a plane, spending the weekend with the founder-owner, in some cases in their house, getting to know them, know their family, know their drives, all of it, just so we could make the impact in the business that was needed. That was the number one requirement. Okay, we're in agreement on the terms, we're good on the contract. All right, I'm coming out to see you and we're gonna spend a weekend together. Or in some cases, the hotel on the Indian reservation.

Daniel: That was an interesting one.

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VISION, JOURNEY, CULTURE, RESULTS

Daniel: All right, let's talk about vision, journey, culture, results as it pertains to mentorship. How can we improve mentorship using the vision, journey, culture, results framework?

Daniel: Where I have had success with mentoring relationships is starting with a clear purpose. One of the guys I look to now as a mentor, I sat down with him several years ago and I said, "I'm looking for somebody who is this, this, this and this," with some very specific criteria. "That's who I think I want to be in the next ten years. Who do you know that's like that?" And he said, "I'm the only person I know who fits your description." And I said, "You're the only person I know too, but I wanted to at least ask and see if maybe there's somebody else out there I don't know. This is where I want to go and I need help getting there. You're the closest thing I've found. Would you give me an hour a quarter, let me buy you a drink and just help me get to where I think I'm trying to go?" That clarity of purpose has enabled us to have a very effective mentoring relationship, because he's able to ask me hard questions now. He knows the reason I'm there is because I want to move in that specific direction.

Daniel: So any mentoring relationship has to start with clarity, and that clarity has to come from the mentee, the person who is asking to be mentored. It can't be enough to say, "I want to be the CEO one day." Sure you do, everybody does. You don't really know what you're asking for. There needs to be some level of clarity of why. How can this mentor help you get where you want to go? And if you don't know where you're going, don't go asking for a mentor, because you're just setting them up for frustration.

Ryan: I think that also goes for the mentor. If someone is coming to you looking for mentorship and they're not sure where to go, the first thing you can mentor them on is helping them get clear on what they're looking for mentorship for. It goes for both sides. What are you trying to get out of this as the mentor? Same thing for the mentee. If you're the mentor, guiding the mentee on what they're trying to get out of it is the first way to help them. If you're jumping straight into solutions when they don't know where they're going, I question your mentorship.

Daniel: I made that mistake early on. One or two people came to me when I was in my late 20s, early 30s, and they said, "You seem to really know what you're doing with your life. I have no idea what I'm doing with my life. Could you mentor me?" And I said sure, because I was going to be a great mentor. And sure enough, a year later they still had no idea what they wanted to do when they grew up. I definitely failed on that one. I take most of the blame, because I didn't vet it appropriately. But some of that's also on them. If you don't know where you're going, any road will get you there.

Daniel: All right, let's go to journey, because I think this one's hard for most people.

Ryan: I don't think you have to know the steps you're expecting in the mentor relationship. You're not going to walk in and know how this relationship is going to work out. Even as the mentor, you don't know where this is going to go, because it's two people in this discovery of what you're trying to figure out. Maybe five or six sessions down you'll have a plan. But the big one on the journey is: suck it up, buttercup. Do the hard work. If you're asking for the advice and you're justifying or making excuses or not putting the time and energy into it, that's a problem.

Ryan: Another one on the mentee side is: meet your mentor where they're at. If you want somebody to mentor you, unless they're retired and this is their pastime, they've got kids and family and a job and everything else. You might have to go out of your way to get their mentorship. There's a gentleman I work with, I'd call him a peer mentor. We're both on the board for a company in California, and we always make a point to sit next to each other on the flight to and from. That is our time. We get three hours there, three hours back to have discussions. We fly out there once a quarter. We try to do a dinner when we can. We both live here in Dallas and we try to get together, but our lives are so chaotic that we make it a point that our journey is sitting next to each other on that airplane. There are things I can learn from him, and there are things he can learn from me. That's our opportunity to mentor each other. So don't expect a mentor to always come to you or be at your beck and call. Map out a path that makes sense for them. You may have to go out of your way, but if they're doing it to help you, then you should take the time and energy to go out of your way to get there.

Daniel: You need to come more than halfway on a lot of those engagements.

Ryan: I will flip it to the other side. If you are the mentor, give them a little guidance. If they're struggling to follow through on an email or set a meeting, be proactive and nudge them along. That's another part of the mentoring. They don't understand how to get where you are or were. So guide them along a little bit. "Hey, let's meet at Starbucks." "Let me know next time you're in town." "Why don't you make a path to the Starbucks down the street here, I can meet you on Saturday."

Daniel: Culture. Where I have done well in mentoring relationships, I have been very clear on who I want to be, my core values and the things that are important to me. There are lots of paths to wherever you want to go, and some of those paths are not gonna work for you. As a mentor, I can't help you get to where you want to go effectively if I don't know the person you want to become along the path of that journey. If you're not fluent with that, a good mentor will pick it up over time and understand what those values are for you as they hear your story. But the earlier you can communicate those values in a mentoring relationship, the more effective that relationship is gonna be.

Ryan: I think there are two sides of it. There's your culture as who you are as an individual, both as the mentor and the mentee, but there's also the culture between the two of you.

Daniel: Ooh, good idea. Say more.

Ryan: In the sense of, "I need you to be brutally honest and call things out, hold me accountable." Or, "I'm going to call your BS out, and if you're not willing to take it, then I'm not gonna waste my time mentoring you. If I'm gonna put my time and energy into it, you've got to be prepared to hear what I've got to say." Now, I'm more on the blunt side of the equation. I'm sure there are other mentors who are better at sugarcoating it, or at least guiding you through, so that may be part of the consideration of picking a mentor. If you're a person, and I don't mean this in a negative way, if you're a person who needs it a little more sugarcoated or a little more tactful to help build your confidence and get you where you want to go, then don't have a mentor like me who's just gonna shoot you straight and tell you exactly what's going on. It's black and white. Versus if you get a mentor who's sugarcoating it and you don't like being sugarcoated, you don't like beating around the bush, then find a mentor who'll shoot you straight.

Ryan: So that's part of it as well. Set the expectation between the relationship, because sometimes you'll get conflict there and it ends in a negative mentor-mentee relationship just because they're not on the same page about the style they want the relationship to be. That doesn't mean you can't be friends anymore. It doesn't mean you can't hang out. They may be your drinking buddy or bowling partner. But define the rules of the mentor-mentee relationship so the two people are on the same page.

Daniel: Now results is where I think it's the hardest. How do you know if a mentoring relationship is working? How do you measure success?

Ryan: There are leading and lagging indicators, and it goes back down to being disciplined about the journey and the culture to execute it. Are you showing up on time? Are you doing the homework? Are you answering the questions honestly? If you're doing that, then you're going to be able to check the lagging indicator. If you're trying to change jobs, you're not going to get a job on your first session with a mentor. They're going to talk about what characteristics and traits you need. Let's look at your resume. How are you positioning yourself? You may have four or five sessions to get yourself ready for the market. Then you're probably going to have some interviews. You might bomb one or two of them, but the mentor is going to help you through that. And then ultimately you land the job.

Ryan: So the leading indicators are: are you making progress on the milestones along the journey? Using the job example: are you meeting and doing the things to get ready for the job search? Are you searching for the job? Yes. The mentor has at least gotten you that far. Am I having interviews? Yes. The mentor has gotten you that far. Am I getting feedback on interviews? Are my interviews getting better? Yes, they are. Did I ultimately land the job? Yes, I did. Where the measurement comes in is, too often people want the instant result. "I want a better job. I'm not getting the better job." That goes back down to what you originally said, the vision and the journey, outlining the expectations. If you can set up leading indicators and say, "These are my milestones, and if I'm making these milestones I'll get to my ultimate goal," it's easy to measure.

Daniel: I don't know how many people have clear measurables like that for their career advancement. But it's good if you do.

Ryan: I don't think it's having measurables to the extent of "I'm going to get an interview this day and I'm going to get a job offer that day." But everybody knows, unless you're 18 years old like my son going through this for the first time, which was a totally different scenario. I told him the path and I worked him through the path. Actually, a perfect example: I'm mentoring my son right now on stock trading. We're going through the journey of buying. We're going through the journey of selling. What's the difference between a Roth and a traditional IRA? What is a 401(k)? There are all those things going on and I'm setting that path for him. That makes sense, because he's absolutely new to the situation. If you're 25, 35, 45 years old, you know what the interviewing process looks like. You know what the job scene looks like. And you can set those milestones.

Ryan: So if you think through any scenario, especially with the mentor, the mentor should have been there, done that ahead of you.

Daniel: If you pick the right one, sure.

Ryan: If you pick the right one, which maybe that's part of helping determine it. "Hey, have you done this before? Walk me through the steps you took." If they're BSing it, you'll probably call it out real quick. I'm not going to say it's super easy. It's just being methodical about thinking through the process and the steps you want to measure success on. If you have a bad mentor, you're not going to make progress toward the goal, plain and simple. If you have a good mentor, it may be a bumpy road, but you will be able to see the tangible results. If it's a career progression, you'll refine your resume. You'll get better at interviewing. Now, a mentor can't fix it if you're not skilled for the job. "I want to go be an aerospace engineer at SpaceX." No mentor is going to get me to that. A mentor is going to say, "You need to go back to college, get an aerospace degree. And when you get that, let's talk."

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PRACTICAL STEPS

Daniel: All right, practical steps for improving mentorship. How do we practically fix mentoring at the office?

Ryan: I feel like we just addressed that. I feel like that was a journey call.

Daniel: We've hit some.

Ryan: I would definitely agree.

Daniel: We've hit some. I think the matching becomes crucial. As the mentee, having a clear vision, which we've talked about, and then finding somebody who aligns as closely as possible to the vision you aspire to. If you want to be a CPA, go find a mentor who's a CPA. That's crucial, because I've found so many corporate programs just randomly match people, and that's very hit and miss in terms of the success of the relationship.

Daniel: We talked about clear expectations in both the journey and the culture side. What are we going to do? Are we going to read a book? Are we going to review your resume? Are we going to just sit and chat? And then how are we going to interact with each other? What are our expectations for this relationship? Am I allowed to be fully honest with you, or do I need to sugarcoat things? Having that clarity upfront is going to increase the odds of your success in a mentoring relationship.

Daniel: And then you know what else is interesting? The opportunity for that to be a two-way street. I remember a guy several years older than me, wildly successful, in a completely different galaxy of success than me. Not what I wanted to do, but still somebody I was learning a lot from. We had lunch together, and at the end of the lunch I said, "Hey, I don't think there is anything in the world that I could ever do for you. But can I at least ask, what is it that you're looking for now? What do you need right now? And is there anything I could do to help you?" And he was so caught off guard. He said, "Nobody ever asks me that." And this guy's one of the wealthiest men in America. I doubt that I can help, but I at least want to know. Are you looking for an intern? I don't know what you want, but at least asking the question, "Is there anything I could do to help you?" I think that's a powerful question a mentee should regularly ask their mentor. Assume that the answer is probably, "Thanks, squirt, I got it." But asking the question creates some unique opportunities for you to maybe help somebody who's much further down the path than you are.

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LAST WORD

Ryan: Mentorship is a vital component to personal growth, especially in the workplace. If you've got ambition to do great things, grand things, or you want a career that provides a lot of income so you can do things for your family and build a legacy, you're not gonna be able to do it alone. Very few people have been able to do it successfully on their own, and if they say they have, they're lying. Mentorship is one of the most key things to successful growth. If you do not have a mentor, look for one. And if you are looking to mentor people, or you have the opportunity, look for those people in need and help. Because if we want to make work not suck, this is a way we can help each other out by giving back to each other. Whether it's a peer mentor or a seasoned individual to a junior individual, it doesn't matter the circumstance.

Ryan: I think you taught me this phrase many years ago: there's always someone you're ahead of. There's someone you are ahead of in your career, or in a skill set, or in a situation. There's always someone behind you. Take the time to look behind you, find that individual, share your experiences and teach them. Because you never know where they could go, and you never know how they can help you grow. They'll help you grow too. They'll help you see things in different ways. If we want to make work not suck, let's fix mentorship as one of the key components, because it will make work better.

Daniel: I agree. I would love to hear stories from the people who are listening about their mentorship experiences. Good, bad and ugly.

Ryan: So subscribe, share, and let's fix work together, one mentorship at a time, so that we can make work not suck.

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OUTRO

Make Work Not Suck. Our podcast that talks about exactly that. Our process — vision, journey, culture and results — we present real-world business solutions that make the difference. Our goal is to make work not suck. Hosted by Ryan Hodges, co-host Daniel Steer. Join us each episode, and make work not suck.