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Episode 147: How to Effectively Manage Young Attorneys

by Heather Moulder | Life & Law Podcast

Do you ever struggle with how to skillfully manage young attorneys? This is something I hear about often (it’s a real struggle for most of my partner and senior counsel clients). And it’s honestly nothing new.

We know that older generations tend to struggle to relate to – and then most effectively lead – younger generations (which is a big reason why leadership coaches like me exist).

But is it getting even harder – as most senior attorneys believe? Are Millennial and Gen Z lawyers so different that it’s an even bigger struggle? And if so, what can be done about it?

No matter where you are in your career, today’s discussion with guest Ben Cooper is a must-listen because we get into:

  • The very real differences in how the younger generations have grown up that impacts how they show up in the workforce.
  • The mental shift for managing young attorneys (that is a game-changer for your management effectiveness).
  • Practical strategies for how to manage young attorneys successfully (so you can train them well AND then retain them).
  • Tips for young attorneys who want to succeed in the legal profession (that will likely surprise you).

We even get into some parenting tips and strategies for preparing young people for the working world (that are must-do thanks to the uber-digital, super-structured world we live in).

Episode Transcript

[00:00:48] Welcome back to the Life and Law podcast. This is Heather Moulder, your host. Today I want to introduce you to Ben Cooper, who is the founder and CEO of Pre Law Pro, a law school admissions and career consulting firm. Ben is a former international lawyer who spent much of his legal career as a litigator in London’s financial district. After leaving private practice, he oversaw the pre-law program at Baylor University here in Texas and now focuses on providing JD and LLM admissions consulting plus career consulting services to young professionals.

That latter part, the consulting services for young professionals, is why he’s on today’s podcast. Because when I first met Ben last fall, I believe it was via LinkedIn, I was intrigued as we got on a coffee chat and started chatting about what that meant and some of the things that he told me about how excellent student skills do not necessarily translate into being an excellent lawyer. Because there are other additional skills involved, that nobody seems to be teaching these days to these young people.

And a lot of times – I’ve noticed as a mom to two teenage boys – there are less and less opportunities for these kids to be able to develop these skills and have some of the same life situations that we had growing up. I think we are doing our young people a huge disservice. We require them to stuff their resumes full of activities and really don’t allow them the time and space to explore, to show off their own independence and navigate their way through their own sticky social issues. They also have no clue how to fail.

So, that’s probably the longest introduction I’ve ever given to a guest, but I felt like it was necessary. It is what we’re going to be chatting about today for the most part. Welcome Ben.

[00:02:40] Ben: Thank you so much Heather, for having me on the show. I’m excited for this conversation.

[00:02:45] Heather: I am, too. Because one of the biggest, I would say, complaints I get from my more senior attorney clients, people who are building practices and building a team, relates to their inability to not just relate with, they do relate to some extent, but their inability to effectively manage young attorneys. And there are some reasons that are on their end of the spectrum, because we lawyers aren’t great managers and leaders, at least not initially. We can definitely learn to be, but we don’t get that training often, and it’s not something we often focus on. But it’s not all on them either.

Sometimes it’s that there’s this disconnect between the two parties because of what that introduction was talking about, and they really don’t understand what to do. So I would love today to get into what you’re seeing, the types of services you’re providing, and the basics of what helps. And to give people ideas for how they can also help when they are in a situation where they’re managing or trying to lead a team of people, including some when they are managing young attorneys, to help them develop those skills.

Because they certainly have the chops from a mind perspective. They know what they’re doing, they have certain skills. They just need to develop this area a little bit more.

And then also give some hope to the young attorneys who feel like “I’m a fish out of water, I’m never going to make it”, that there is hope and there are things that they can do for themselves.

Is This The Same Issue of Senior Attorneys Not Knowing How To Manage Young Attorneys Or Something Else Entirely?

[00:04:18] Ben: Yeah, I mean, I think it’s almost like when you go to the gym for the first time in a long time and you realize you’ve got all these muscles that you never even knew existed that start to hurt. I feel like the current generation is a little bit like that metaphor. They’ve got the muscles, they just have never had the opportunity to use them.

And I’m sure a lot of the supervising associates and partners that are listening have encountered very academically talented young lawyers who just lack some of that finesse that we have taken for granted for a couple of generations of attorneys, that sets them apart from their student self as they transition into being a young professional.

How Societal Issues (And How We Raise Our Kids) Impact How To Manage Young Attorneys

I’ve certainly seen, I think, a decline in college students who have worked during high school, and I think that is having an impact. But I also think, I know we hear about this all the time, but I think it would be remiss, not to mention the significant impact that smartphones have had on late Millennials and Gen Z.

Little To No Autonomy, Independence Or Work Experience In Childhood

We came from a generation where our parents trained us to answer the home phone a particular way. This is who we are. This is the number. How may I help you?

Where the idea of getting a bike as a young kid to have the freedom was exciting and some risk was involved with that. And sometimes you scraped your knee and sometimes you learned some lessons. And I think we’ve got a generation that has lived very, very safely, and I think that’s been made much worse by Covid. And we’re starting to see a generation of very talented people who never had the opportunity to realize their full potential because they don’t embrace failure as a necessary ingredient to success, but are so terrified of the risk of failure that they never really push themselves as far as they could. And some of them who want to don’t have the tools because they’ve lacked some of that developmental employment experience that you and I take for granted.

[00:06:44] Heather: Yeah, I worked as a high schooler. I came home, rode the bus home, went to my employer, worked for a couple of hours before I went home and did my homework and got everything done. And I had a younger brother that I had to help take care of because my mom was gone a lot. And it feels like kids for a while now have not been allowed to be autonomous, to be fully independent. I think there’s a lot of things that lead into this. It’s not one thing. Part of it is the way we’re choosing to raise our children. When Stranger Things – have you ever watched that show?

[00:07:29] Ben: Fantastic show. Yeah.

[00:07:30] Heather: It completely shows the life of an 80s kid in the sense that these kids’ parents have no clue where they are. They’re going all over the place on their bikes. That was my life.

[00:07:42] Ben: Oh, mine too.

[00:07:43] Heather: My children can’t fathom that because nobody does it. And it’s something that’s bothered me a lot as I’m raising my kids. Like, I don’t agree with this. But then what do you do when there’s nobody to go out and do things with and to be outside with? So there’s a societal issue there around how we’re choosing to raise our kids.

Overly Structured Lives

Then there’s also, I think, this issue of resume stuffing. I think, to a point, doing these activities can be good and helpful, but to a point. Because they’re uber structured and it basically helps get the kid from point a to point b to point c to point d. But it doesn’t allow for a lot of self exploration and independence and autonomy again. And there’s usually in these structured activities, adults around to at least watch over things so you’re not getting into the same issues societally with one another that we had to navigate – with problems with people and all these things that we had to learn how to deal with.

And so I think they’re lacking certain ability to develop and hone those skills. And then you, again, placed on another big thing, which was the smartphones and the way we live our lives and how everything’s done for us. It’s taken away a lot. It’s given a lot, but it’s also taken away some things and opened up a whole pandora’s box of other issues. Right? Yeah, it’s kind of threefold, I would think so.

[00:09:15] Ben: I think there’s a couple of things there.

While I was at Baylor, before I ran their pre law program, I actually worked as a residential chaplain, which meant I lived on a residential hall.

Thankfully, it was not in a dorm room, but I lived and did life with students for several years. And what I noticed, and I think it’s pronounced here in the United States, growing up in Australia, this idea of resume stuffing was not what it is here. We had some programming, and you wanted to build some sort of resume, but it wasn’t the high pressure, high intensity that you see here in the United States when it comes to college admissions specifically, everyone has to have this massively stacked resume or you won’t go to college. And, of course, if you don’t go to college, we all know it’s the end of the world, right? And we are seeing how wrong that presumption is.

But what I think happens when you have kids who are over programmed and their resumes are stuffed with fluff, a couple of things happen.

Over-confidence (that isn’t real).

They create in their own mind, often a sense of overconfidence, because look at how great my resume is. But what we know about competence, sorry. Confidence is that it’s only really built on competence.

And so what happens is they’ve got this false, brittle sense of confidence.

They then come to college and they encounter their first heartbreak, or they encounter their first difficult test, and that confidence that had been holding them up through high school very quickly falls away. And then what are you left with? And this is where to the parents listening, I would just urge you to encourage your students, and I don’t want to say children, because we’re talking more about high school students, to give them those opportunities to build a sense of confidence that is built on competence, and that means doing things and failing at things.

And you want them to fail when the stakes are relatively low, if they get a job at a fast food place and they do a terrible job and they end up getting fired, which happens. Right. You turn up late, you don’t go to, you sleep through your shift or whatever it is, the stakes of that in the scheme of your life are virtually nil. Right. No one’s going to care that you got fired from Domino’s pizza. When you apply for a job as an attorney somewhere, no one’s going to care.

They are going to care if you got fired from a law firm because you weren’t doing your job correctly or you missed a limitation date or whatever the case may be. So you want your kids to fail so that they learn lessons as early as possible because that’s when the stakes are the lowest.

[00:12:07] Heather: Yeah. I think there’s been an incorrect for years movement in building self esteem in a way that really lacks that confidence piece. So you’re not building real confidence. And so when people get out and figure out, oh, I’m not all that. I have flaws, I have weaknesses that we basically just didn’t highlight because of how we, the way we structured our life and the activities that we did, et cetera, it can be devastating because they’ve never dealt with that. And I kind of liken it to.

Not Knowing How To Fail

I had a conversation a couple of years ago as my now 18 year old was getting towards driving age, and it was a family member who has a daughter same age as my son. They’re a couple of months apart. He’s like, I’m not letting her drive at 16. She’s not learning to drive until she’s 17 or 18. And I’m like, my conversation was, well, okay, do you really want her to start driving around the time she leaves the house so that you’re not a safe spot for her to come home to and you’re not able to be there as kind of that catch safe and watch over her and help.

And he stopped and started thinking about it. And this goes for dating, too. I’ve had conversations.

[00:13:26] Ben: I was just going to mention that.

[00:13:28] Heather: Of daughters who are. They’re not dating. And I’m like, are you kidding me? They’re going to go off when they’re 18. And if they’ve never dated before, you really want them to have those first experiences without you ever being around.

And it stops people in their tracks.

But that’s basically what we’re doing to these kids when it comes to all these other things, when some of them with dating and driving too. Right. And that’s not, I feel like our job as parents and this is slightly turned into a parenting. But I think this is important because we’re going to turn this back around. It’s important to understand where these kids are coming from. Yeah, but our job as parents is to create competent individuals that can function in society and be independent and be good members of society. And part of that is you have to teach them how to fail. Teaching somebody how to fail has nothing to do with you swooping in and saving the day. It has to do with you being there to support them and say, yeah, that sucked. Sorry, it had to happen.

What did you learn from it? Right. Or even punishing sometimes depends on the failure. Depends on how they fall down. Right. But being there and saying, okay, so what are you learning from this? How are you going to apply it moving forward and letting them fail, too? One of the best things that I think happened to us, my husband and I, as parents, is the school that our kids currently go to.

They’ve been there since they were very young and all the way through, up through middle school, the teachers and administration would constantly tell us, let them fail. Let them fail. Let them not turn something in. Let them get the zero. Let it massively impact their grade. Because guess what? What they get in 6th grade and 7th grade doesn’t matter. What they get in high school does on their resume. Let’s teach them the lessons now so they don’t screw up there or in college.

And my kids had to do that to learn.

Look at that. Didn’t get it turned in and how it impacted your grade.

[00:15:28] Ben: Yeah, there’s a few things to unpack there. So I would concur with your kind of thoughts on self esteem. I actually think self esteem is something that we grew up with in the 80’s. We’re supposed to have high self esteem. And so we’ve parented with this idea of self esteem is important. And I actually think self esteem is nonsense. I think what you really want is self respect.

[00:15:53] Heather: Yes.

[00:15:54] Ben: Because if you raise young professionals and students who have self respect, that dictates the level of effort, that dictates how they’re willing to respond to challenges. But you can’t build that self respect unless you allow them within the buffers of responsible parenting to make mistakes, to make errors. And I would kind of compare it almost to you.

Think of the killer whales that they put in swimming pools at SeaWorld and whatnot. They’re fed the best possible diet that we can think of. They have round the clock veterinary care. Their water is filtered and taken care of. And for a little while, they might find some degree of mental stimulation. But eventually they come to resent their keepers. And I think that’s the other danger with this, is that eventually your students will become adults. And when they become adults and realize that they are not prepared or equipped for the world that they are in, they will begin to look for somebody to attribute that failure to. And that finger can very quickly point to not just the education system, but to you as parents.

Again, I don’t want to make this just a parenting thing, but I do think that we are facing a generation who are very unprepared, and they don’t understand why, because it’s not really their fault. Because they haven’t been given these opportunities to genuinely fail where the stakes are low.

The Role Technology (and Social Media) Plays

But then there are also other things in our world that they have not encountered, like a world without a cell phone, a world without social media. You and I could make a stupid. We could go to a college party, get a little drunk and make a fool of ourselves.

And apart from the friends who would give us a hard time, that would be the end of it. Nowadays, that can go viral and turn.

[00:17:49] Heather: Into a meme, can ruin the person’s life, which I ridiculous.

[00:17:54] Ben: But it’s also why they’re so that. I think that’s the other counter to this. Why failure is so terrifying is because you’re no longer just failing in front of yourself. You could be failing in front of your entire community, whether that’s school and far more. Which is why I think encouraging those little mistakes as early as you possibly can will help develop self reliance, self respect, and a confidence that’s built on degree of competence.

I think also the downside of self esteem, and I’m sure that some of the senior attorneys and partners listening to this have encountered, is that self esteem can turn into entitlement. And that’s a complaint I hear a lot from senior managers, partners at law firms and accounting firms, is this level of entitlement. And I think to some degree that’s true, but to some degree, I think it’s also this disconnect where they don’t completely understand where this generation is coming from, and this generation doesn’t completely understand why they have to do certain things the way they’re done.

What Senior Attorneys Must Know To Manage Young Attorneys Skillfully

[00:19:04] Heather: Right. So then, okay, let’s turn that into. We’re talking to the more senior people who are trying to train and manage those who are coming in, those of this generation.

What do they need to know?

Because I think they make assumptions about who these kids are based on. They’re basing it on their past without realizing, these kids have not experienced the same things, they have not been through the same things. They don’t see the world the same way as a result.

So what would you tell them? What do they need to know in order to have the right mentality, even? Because I think what I’m hearing here is they really do need to know some things and utilize that to change their mentality around how they approach them. Otherwise, there’s always going to be this disconnect.

Young People Are Smart, Savvy & A Bit Cynical

[00:19:54] Ben: Yeah. So I think it’s important to remember that they’re not stupid. They know that the resume stuffing is a little bit of a game. They see it and they know they’re playing a game, but they realize it’s a bit of a stupid game at the same time. So when they get to the professional stage and they’re like, why do I have to do this? I’ve spent the last four years stuffing my resume with stuff. This stuff doesn’t matter. It’s never really done anything for me other than get me into school. Why do I need to keep doing this? So I think the first thing is understanding that they’re coming from a culture where they’ve been over programmed, over pressurized, and in some sense, they’ve already experienced at some point, some level of burnout.

[00:20:35] Heather: And they’re cynical then because of it.

[00:20:37] Ben: Very cynical.

#1 Tip For How To Manage Young Attorneys: Tell Them Why

The other thing is, a lot of the things that we do as professionals and we had to do as young lawyers doesn’t make sense to them. And there’s no explanation as to why he might be doing it as a manager. So I can remember, for example, I had one partner that I worked for who I will forever be grateful to, but in many ways, was the hardest boss I ever worked for.

And I would write letters, and they’d go to the partner for sign off, and they’d come back with red ink all over. And I got to the point where I was like, well, hang on. I used this exact same wording three weeks ago, and it was signed, why is it coming back different? And what I realized was this partner was being very, very hard on me because they were trying to make me better.

And it wasn’t until I went to them and said, hey, I don’t understand why I’m getting such a hard time here. That they sat down and they explained what they were doing and why they were doing it, and then it clicked. So I think the first thing I would say is, don’t assume that they know why you are doing something. Don’t assume that they understand why they have to do some kind of menial task. There’s plenty of menial tasks I had to do as a baby lawyer that I was frustrated by. But I now realize by doing small things with some precision, it made me a better attorney when the stakes were a little bit higher. So make sure they understand why you’re asking them to do certain things.

The other thing, I think, is going back to the resume stuffing culture and the high pressure, high performance stuff. So they’ve come from this environment where they’ve been used to stuffing their resumes, and it builds this sense of self esteem, really, that’s only really shored up by constant affirmation.

One of the primary complaints that I hear from managers and partners is that they have to give constant amounts of feedback. And there was a recent study in the Australian civil service where it was the Australian Federal Police, I think it may have been, and they looked at intergenerational employees and the ways that they responded and needed feedback. Now I forget the numbers, but what was significant is that the difference between Gen X and Millennials and their need for feedback was tiny in comparison to the amount of pieces of annual feedback Generation Z would require.

Why Young People Need So Much Feedback (& What To Do With This Information)

And I think managers need to understand that part of the reason that this generation is so desperate for constant feedback is because there is a level of confidence that’s built on self esteem, which means it’s very easily shaken.

And so because there’s not real confidence there, it’s that affirmation, it’s that feedback that helps keep things level. Whereas if they’d been built on competence, you can handle a little bit more rocking of the boat. So I think managers need to understand, they need the feedback to help build confidence, even though they may present as being maybe even overconfident. That feedback is what undergirds a confidence, builds on self esteem.

There’s also, I think, just a need for them to explain why they have to do things. Like, I can remember we had an intern come in, and we had him basically do a bunch of photocopying for us for some briefs, and we had had another intern who we’d given the same task to. Different case, but same task, and they made an absolute mess of it. Pages were upside down. They weren’t in the right order. And clearly they just thought, well, it’s photocopying. How hard can it be? And they didn’t really take any pride in their work. The other intern did exactly what we told them to do. They did it quickly, but more importantly, they did it accurately.

And so we were like, all right, we can trust this guy with a little bit more stuff. And so he started getting more sophisticated, more demanding tasks. And he was the intern that we offered a job to as a young associate when he finished law school because he did the small and menial, and he did it really well. And so I think there’s this idea that this is beneath me, that some task is beneath me, but don’t lose sight of the fact that doing some tasks well, even if they’re small, will help you do the more sophisticated tasks in a way that will matter.

[00:25:11] Heather: As a lawyer, and I would say so that’s speaking to the young people, but to the older, like the people who are managing, remember to explain completely why behind, why they need to be doing that so they can get to that point.

[00:25:27] Ben: And I think also let them know that if you’re going to give them a bit of a hard time, there’s a reason for it.

It’s okay to hold them to a standard and to put a little bit of professional growth pressure, but it will be easier for them to understand and to absorb if they know what you’re doing.

If you’re not just being difficult for the sake of being difficult, if you’re not just being a boomer, for the sake of being a boomer, help them understand that, hey, I’m going to be tough on you, but I want you to know that I’m tough on you because I think you have some real potential.

But the only way we can get that potential reached is if I push you to be the very best lawyer you can be. And that’s going to require me to hold you to a certain standard. That is a way off for you, and I want you to get there. But the only way we can do that is to hold your feet to the fire a little bit. Now, if they understand, it’s a lot easier for them to put up with and endure with.

[00:26:24] Heather: Yeah, I think that at least a lot of the commentary I hear about the need for affirmation and knowing that you’re doing a good job is exhausting to some attorneys. Right?

[00:26:38] Ben: 100%.

[00:26:39] Heather: And they want to know that there’s a light at the end of the tunnel, that if they do these things, it will stop eventually or that at least it’ll start to diminish. That will work to help create more competence and then real confidence so that they’re not relying on that self esteem that was so focused on it throughout their younger years and into young adulthood. I’m hoping that you have some evidence that that is the case. And that if it is, I would guess some of this has to do with their cynicism, even because of the way they grew up and this resume stuffing. And I can see it in my high schooler with some comments he’s even made around some of this stuff. Right?

And they’re cynical, and so they’re going to question the why behind everything. But if they start to actually get feedback and get pushed and see that they’re actually getting better and get more feedback, that, yes, you are growing and be told along the way this is why we’re doing it, then some of that cynicism, I would hope would go down and they can settle in a little bit more to feeling more competent and then having real confidence and then not needing so much later on down the line. Is that the case or no?

What Motivates Young Attorneys?

[00:28:02] Ben: We’re still, early on in this generation, we haven’t really seen them reach their full adult kind of professional lives yet. So there’s still a lot of unknowns. I do think they, like millennials, are prone to job hopping, probably more so.

And for them, money is not a primary motivator.

They are not motivated by the same things that Gen X was and that millennials were.

They’re more about things like work life balance, they’re more about experiences. And yeah, they like money, but it’s not the same motivator that it was for prior generations. And we can wish it would be different, we can opine that it should be different, but this is the generation that you’re going to be employing. So you have to be willing to adapt or you’re going to have a really difficult time not only attracting new talent, but retaining that talent. And I think for them, they want to feel like they’re part of the community and the culture of your firm, of your business, whatever it might be.

And I think from an attorney or from a law firm perspective, a great way to look at that is to treat that feedback, that giving of that regular feedback, in the same way you would recognizing that a young lawyer doesn’t make you money for the first little while, they cost you money, right? The amount of time that goes into duplication, reviewing work, all that kind of stuff, that feedback that you’re giving is an investment in that person that will go a long way to helping them stay where at other firms they may jump ship and go somewhere else. And it’s a different form of investment that I think is going to be more compelling to this generation than just giving them more money.

[00:29:52] Heather: Right. I would also say even for those of you who feel like it’s exhausting and worry that, well, it’s still not going to work, or it may not, you’re going to need to shift your mentality around it because it’s a requirement if you want a team of people. You can’t always have a team around you that’s a certain generation and above the longer you work. It’s just not going to work that way. You’re going to have to employ these people.

A Mindset Shift To Improve How You Manage Young Attorneys (& Make it Enjoyable)

And I would try to look at it as this is my way to give back to the future generations and to the legal profession for the future and see it as an act of mentoring and an act of growth for yourself. Because it is a growth activity for you as well, to mentor and manage and lead and learn how to be better at it. And when you take it on from that perspective, you can find it much more enjoyable, which then makes it less exhausting because your mentality around it is switched.

[00:30:54] Ben: Yeah. It’s not a chore that you have to do. It’s an opportunity to pour into the next generation.

They Care About Purpose (Here’s What That Means)

I think, too, on that note, millennials, but especially Gen Z, they want some kind of purpose. To them, the nine to five is the nine to five. Their time is their time, and they have stricter boundaries than maybe some other generations have had when it comes to work life balance. But I think if there’s a purpose that they can find in what they’re doing, it makes a heck of a difference. And if you don’t mind, I’ll share a story from my own journey.

I started out at one point at a boutique doing insurance, defendant insurance work, and I had a huge portfolio against the manufacturer of clothes dryers. And I remember sitting down with the partner one Friday that I was working for and just saying like, hey, I know I’m getting good training, and I know this is a really good way to learn how to draft and whatnot, but you’ve been doing this for a long time. What motivates you? What keeps you wanting to do this? Because at that point, I wasn’t sure I wanted to do dryer claims for the rest of my life. And he said to me, look, he said, have you ever had a house fire? And I said, no. And he’s like, well, he’s like, when you have a house fire, you might lose a loved one. And if you don’t lose a loved one, you might lose everything that you’ve ever built in your life. Everything that has meaning, photos that can never be replaced, et cetera. He said, I’ve talked to these people, and he said it’s heartbreaking to listen to their stories of loss. And he said, these people are bringing in to the country dryers that we know have a defect, and the only way that we will stop them from doing that is if we hit them hard enough and enough times. And he said, that’s what gets me up in the morning. That’s what makes me want to continue to do this work.

And I’d never thought about it that way. And I was a young 20 something attorney at that point, and I was like, wow, that actually makes me really want to do a good job on these drier claims. That might not sound sexy, but once you realize there’s a purpose here, there’s a way that I can take this task and give it meaning.

All of a sudden, I was way more motivated, way more dedicated, and really wanted to nail this case. And I think helping your young associates find ways to really look at what they’re doing purposefully makes a difference to their desire to be there, their intent when they’re there, and their willingness to invest in your business by giving you their best efforts.

[00:33:38] Heather: And I would kind of liken it – so I’m big on values and understanding your own values – but also it’s important to understand the people around you, like your important clients, your friends, your family, but also those who are on your team. What are their values? Because the values that they have are likely at least a portion of why they chose to do what they do in the first place.

They chose to be a lawyer for a reason, for a bigger purpose, to make an impact in some way, shape, or form. Figure out what those values are that they have, so that when you are talking through a new case or a new deal or whatever, you can talk it in that way as well and kind of connect it to the values so that there is a deeper meaning and a deeper purpose. I have similar stories, too, because I was a finance lawyer, and a lot of people kind of like, oh, yeah, you get to make the big bucks. You just paper. You kill trees to produce all this paper.

I’m like, yeah, but I also allow these small businesses to grow and hire more people and make more whatever it was that they did for the benefit of their clients. And there was this one time where I had a lender who was a lender to, like, do you know what scratch and dent, like, auto loans are?

Well, he had these dealerships that basically allowed people to purchase, and really it was more like lease to purchase because they didn’t have good credit.

Many of these people had horrific credit. Some were former criminals that were out and they had no way to easily buy cars. And he was really big on making his dealerships nice, beautiful, clean, treating people incredibly well because most of the places you go that are like, that really are dumpster fires. Right. His places were not. And you got to know him and stories around helping people get back on their feet, helping people build credit, helping people. And all of a sudden, what sounded kind of dorky to some people and like, oh my God, that’s not all that fabulous. Or they wanted me to be doing these really cool big deals, which I did, but it was stuff like that that was actually more meaningful to me.

[00:36:02] Ben: Yeah, I think that’s a new way of attracting talent too, is to building in opportunities for things like pro bono and service that’s not competing for billable hours.

I think in a lot of ways this generation would have a preference for a lower salary with a lower billable requirement that also allows them time to do pro bono work, for example, public service.

Quite happily, because I know there’s an unavoidable economic consequence, lower billables has to equal lower salary. But I think this generation would be far more open to that because again, you’re allowing them to create some meaning and purpose in what they’re doing and they’re not just chasing the next promotion, the next dollar, because that’s just not the generation that they are.

[00:36:57] Heather: Yeah, no, I agree completely. And of course, big law just continues to raise salaries, raise hourly requirements, raise, raise, raise, raise, raise.

[00:37:07] Ben: But it’s such a small chunk of the overall legal market. It is that it distorts the way we see the law, I think, and I’m dealing with law school applicants.

The law is seen through that lens of big law, but it’s not the majority of the legal profession. Most lawyers are in firms of 50 or fewer lawyers. So I think law schools, I hope, will do a better job at helping students see that big law is one path, but you can have awesome careers in medium sized firms and small firms, in boutiques, as a jag. There’s just so many other paths you go without. And big law. Not going to big law is not a failure. I didn’t go to a big law firm until late in my career. I did it the other way around.

And when I think so, I started in a small firm, then I went to a boutique, then I went to an international firm. And the best experience I ever had was at a boutique with three partners. It was phenomenal and we missed that a little bit.

Individualize Your Approach

But there was one thing I did want to add, and I just think this comes back to as leaders, partners, senior associates, and so on, they have to be willing to adjust the way that they lead. If you have a team of people, they don’t all respond to the same motivators. You can’t just be the RA motivator for everybody and expect everyone to respond the same way. Some people cannot handle that, and they need a softer touch. But if you’re able to move around and change the way you lead individuals within that team, you’ll get a much better outcome instead of just applying this catch all approach.

[00:38:49] Heather: Yeah, and that goes for who? It doesn’t matter whether we’re talking Gen Z or somebody else.

That is applicable. Regardless, if you want to get the most out of your team and your people, you really need to take time to understand each individual at an individual level, understand their strengths and weaknesses, understand their personalities, and tailor your approach to that individual. It’s kind of like what I do in my coaching. I get to know my individual clients, their strengths, their weaknesses, their personalities, their values, so that I can tailor my approach to them. And it’s like you need to take a coach approach, and if you’re not sure what to do or how to do it, reach out to somebody like Ben or I, because that’s what we do. We help people with.

Get To Know Them (& Be Yourself)

[00:39:38] Ben: Well, and I think, too, with the intergenerational stuff, the temptation is to try and imitate in order to connect, and that always comes across the wrong way. It always seems insincere. It always seems awkward. So they don’t want you to imitate them. They just want you to understand them as best you can. And so take the time to get to know what your young employees are actually interested in, what are they doing in their lives outside of the office, and show an interest. You don’t have to imitate it. You don’t have to try and learn Gen Z Lingo, but just show an interest. Engage with them in a way that demonstrates that you respect them as young professionals so that you’re not looking down, because there’s already this kind of inbuilt animosity between older generations and Gen Z because of all the stuff we see in the headlines. And I think you can mitigate that impact by just trying to adjust the way you approach your leadership for all your members in your team, but also trying to get to know them on a meaningful and personal basis and also really helping them to understand that the standard that you’re going to hold them to isn’t arbitrary.

There’s a meaning and there’s a purpose behind it, and it’s an investment in their development because you see something in them that needs to be developed and grown out to its full potential, instead of just saying, hey, here’s the billable target you have for the month, and I expect you to hit that.

And expecting them to respond in the same way that maybe you did when you were a young attorney.

Tips For Young Attorneys

[00:41:18] Heather: Okay, so we’ve been through kind of the approach, the mindset, the don’t assume, how to better understand them. We’ve given some practical, tangible things that can be done to relate better and then also to manage young attorneys better.

What would you say to these young attorneys who are struggling and where can they go? What can they do to improve their communication skills, to improve some of those soft skills that maybe they don’t have to learn how to fail, which feels terrifying, I’m sure, because they feel like they never have been given the opportunity to.

[00:42:01] Ben: Yeah. So for the younger professionals out there who are struggling, I would just say from the get go, there are good reasons to leave a firm. I’m not going to sit here and tell you, hey, you should stay in that job that you’re in for the next five years. There are good reasons to leave a firm, but those reasons aren’t as broad as we might think. So the first thing is, if you’re in a situation where you don’t love what you do, the way you approach it is going to change what you get out of it.

Ask What You Can Learn (In Any Situation)

So you might be in a job that you really don’t like, and you might have a boss who’s a really difficult boss, but there is an opportunity there to learn. How can I learn to work with people that I find difficult?

What lessons can I learn from this person on what not to do or what to do, so that when I’m in that next opportunity, I’ve learned those lessons?

The biggest skill deficiency I see isn’t necessarily black letter law or even practical courtroom experience, because a lot of schools have put a lot of time and money and emphasis on experiential learning.

Focus On Soft Skills (Especially Relationship-Building)

Where they fall short, I think, is the soft professional skills. And I’ll give you an example. A lot of the college students, law students, and one to five year associates that I work with struggle to build out a professional network. And you and I both know that if you want to become a partner, it helps a heck of a lot if you’ve got a client following, because otherwise you can just be a high paid associate.

Now, to get that client following, you have to be able to build relationships from scratch.

And that, I think, is an overarching skill that’s missing. So what I spend a lot of time doing is helping people figure out how to go out and build a professional network. And I will use tools from the intelligence community and using the intelligence cycle to do that.

But because of technology where you can send a text or a LinkedIn message, we have lost the ability to build rapport and to build relationships. And I think part of the reason this generation is reluctant to do it, and I understand this, is that it feels like networking to them feels greasy because I have to meet someone to get something from them.

Now, the fun about working with students and young attorneys is helping them realize that it’s not about getting a lot of the time. You’re going to give and give and give and give before you get anything in return. But in doing so, you build a very loyal, meaningful portfolio of friends and connections and colleagues that not only make life a little bit more interesting, but can help you pivot into the right role, into the right practice area to find the new opportunity, especially when it comes to jobs. A lot of people don’t find jobs through websites. Indeed. And whatnot. They find them through people that they know.

[00:45:03] Heather: Yeah, absolutely. I would say when it comes to networking, to change your approach, understand that human beings have this basic need to connect with other human beings. And when you’re out there networking, that’s really what that’s about. At the end of the day, it’s connection. It’s building real relationships with people, not fake ones, and you are not expected. Nor do I recommend that you put people in your network that you don’t like, that you’d never want to do business with, that you’d never want to work for.

The whole point of networking and getting out is to see who you are more attracted to as another person and who’s more attracted to you as a person, where you sync up more and then naturally build relationships with them. So be yourself, don’t worry about how others will perceive you, and also be curious about others and make it about learning about them to the best of your ability, so that you can build those relationships and see, well, who do I actually like and who do I want to be part of my network?

A Note About Anxiety In Young People

[00:46:07] Ben: Another thing just to add here for the managers and partners and whatnot, is this is a generation that is very, just inherently anxious. I’m not talking about clinical anxiety, but just anxious and there’s a lot of reasons for that. If you’re looking for a great resource, I would recommend Jonathan Haid’s book, the Coddling of the American Mind, just to give you a little bit of an insight into this base level anxiety that this generation has.

So when you’re working with your associates or your summers and you notice some of these issues, realize that there’s an anxiety that you and I probably never felt that has just kind of been baked into the cake. So I would encourage you to give your employees, interns, whatnot, opportunities to go and make mistakes where the stakes are very low.

So, for example, I recently had a client, very talented, recruited to a big law firm, but was absolutely terrible at introductions and going out and meeting people on their own, and it just made them almost sick. And so what we decided to do was to find a situation where the stakes were so incredibly low that they found a level of anxiety that they could manage. So for them, that was the supermarket. And so we started out, it’s like, all right, this week you’re going to go to the supermarket every night after work, and you’re going to talk to five people every time you go. So by the end of the week, you’ve spoken to 25 people, and you don’t have to tell them your life story. Hey, how are you? What’s going on? Having a good day. Have a nice day and move on. So you’ve got to help them get in situations where they can tolerate the level of failure first before you throw them in at the deep end. Because if you throw them in at the deep end and they can’t swim, they will drown.

And so the role that you’re going to play is different to what it’s been in the past, but there’s a lot of diamonds in the rough. And if you can find a way to meet them where they’re at and help them understand what you’re doing and why you’re doing it will make such a difference, I think, to the quality of work and the quality of the community you have at your firm with this increasing number of Gen Z employees.

[00:48:28] Heather: Yeah. And I second the coddling of the american mind. And he’s got a new book coming out around social media and the impact on young people that I don’t think it’s out officially yet. I think it comes out soon. And I would encourage people to be on the lookout for that. I think it’s substack articles, and he’s been writing about that for a while, and it’s fascinating and it’s interesting and it’s terrifying all at the same time. But he has some ideas for those of us who are parents and how to help our kids. And then also society also maybe rules around what we can do to help people because it is impacting the minds of young people and not in a good way.

Social media.

Introducing Environments For Civil Disagreement

[00:49:23] Ben: Well, and I also think one of the other things you can do, and this is a little bit of a sidebar, but it’s related in a lot of ways, is creating environments where there is civil disagreement.

[00:49:35] Heather: Yes.

[00:49:36] Ben: Because what’s happening, and having been on a college campus for quite some time, there is this ethos that if I disagree with you on an issue that I hate you, which, I mean, I can remember growing up with people who are along all kinds of political spectrums, and we’d get into it on a particular topic and at the end of it be like, hey, do you want to be, and we disagree on this one issue, but you’re still a friend. So realize that they’re coming out of a higher education system that has in many ways fostered this ethos, and you’re going to have clients that they don’t agree with that clients that have different attitudes to them, you’re going to have different attitudes to them and creating environments where they realize, I can disagree with you and you can disagree with me, but it doesn’t affect the way I respect you or think of you as a professional or the value that I think you have as a human being.

That’s a longer project that’s going to take some time, but it’s going to become an issue. And you only have to look at some of the recent news stories, for example, Stanford, where you had a federal judge yelled at, and those folks are then going to go into law firms, and you have to represent that not all your clients are great people, not all your clients are nice people, but you still have to give them your best.

And so I think fostering that level, and this again, comes back to getting to knowing your employees, meeting where they are and developing them is letting them know it’s okay to be in situations where you disagree with each other. It doesn’t have to mean that we’re at ODS.

[00:51:08] Heather: Yeah, I would just say to finish that up obviously goes back to parenting and our education system and a whole host of issues we can’t get into. But when you get into having people who have grown up in a way where they’ve not been around a lot of people who’ve disagreed or they have but nobody’s expressed it because everybody’s too afraid, really a lot more of the latter, I think. But understanding that if you take that time as a leader and manager to get to know them and to care and to ask, and then you share over time in a way that is non confrontational and just meant to show that this is okay.

We don’t have to agree on everything that slowly introduces people to that concept in a safer manner and allows them to see that, oh, this is actually okay. And not just okay, but preferred because it’s interesting to have more people that don’t agree. It’s interesting and more challenging and more fun. Everybody being in agreement on everything is kind of boring.

[00:52:11] Ben: Well, especially as lawyers, our job is to argue and to put our clients best possible case forward. And that can mean you have someone that you went to law school with on the other side, and your job is not to give them an inch. Your job is to represent your client and to the best of your ability. And we have to reinstall that collegial sense of civil disagreement. And it’s okay to disagree with somebody.

And I think it’s kind of eroding the legal profession. I think, sadly, in a lot of ways is this kind of tribalism.

[00:52:49] Heather: Yeah, I agree. I actually plan to have an episode. I don’t know if I will have it this season. It’ll either be towards the end of the season or at the beginning of next to talk a little bit about these issues. Well, thank you so much for joining me today. This has been a wonderful conversation. Before letting you go, why don’t you let people know where they can find you?

[00:53:12] Ben: Well, thank you so much for having me. This has been a fantastic opportunity. I am Benjamin J. Cooper on LinkedIn. Feel free to connect with me there. You can also find more about and my email. For anyone who’s interested or wants to reach out, you can simply email me at awesome.

[00:53:40] Heather: Thank you so much. I will put links to all of that into the show notes so that anybody who wants to reach out can.

[00:53:48] Ben: Thank you so much for having me.

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About Ben Cooper

Ben Cooper is the founder and CEO of PreLawPro, a law school admissions and career consulting firm. He is a former international lawyer who spent much of his legal career as a litigator in London’s financial district.

After leaving private practice he oversaw the Pre-Law program at Baylor University and now focuses on providing J.D. & L.L.M. admissions consulting plus career consulting services to young professionals.

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