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​Want to be a successful lawyer? Learn how to be a better leader.

You’ve probably already realized that success as a lawyer requires more than having good law-related skills and great lawyering. You must also know how to effectively manage and lead other people (among other things).

Unfortunately, there isn’t a law school class on how to be a better leader or manager.

Which is why I asked fellow coach Amy Gardner onto the podcast today to discuss why leadership is such an important yet overlooked skill and – best of all – how to be a better leader.

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Episode Transcript

[00:00:48]​ Well, hello hello, everybody. Welcome to the Life & Law podcast. I am your host, Heather Moulder, and today we have a guest.

Amy M. Gardner works with law firms and corporations to re engage teams and help them thrive by utilizing a proprietary team driven leadership approach to build leadership skills, improve relationships, strengthen emotional intelligence, have difficult conversations, and more. Her work with teams and lawyers draws on her unique experience as a former big law associate partner at a mid size Chicago firm and Dean of Students at the University of Chicago Law School. Welcome, Amy.

[00:01:25] Amy: Thank you. I’m so glad to be with you.

[00:01:28] Heather: All right. So because of the work you do, just so everybody knows, we’re going to be talking about leadership and how to be a better leader.

And we’re especially going to be talking about: team development and development of others, and how that plays into leadership. Because I think this is an area that lawyers just don’t do enough around, we don’t talk enough about, and it’s super important.

When I was introduced to you – we met through a mutual friend – I checked out your website and I’m like, oh, this topic is perfect. We’ve got to talk about this because we haven’t talked about it a lot on the podcast.

So I’m really excited to dive in today and see what lessons you can impart upon our audience around how to be a better leader.

But before we do that, I want to learn a little bit more about you…

Amy’s Story & Background

Why did you become a lawyer in the first place?

[00:02:15] Amy: So I have one of those stories that I think a lot of people can identify with. Where I was in second grade, and we were supposed to draw what you wanted to be when you grew up.

And lots of people were drawing, like, the symbol for the American Red Cross of the girls because they wanted to be nurses. And all I could think about was, I don’t like blood. And I remember this very vividly. Mrs. Frazier’s classroom, second grade.

And so I drew scales of justice, or my second grade version of scales of justice because those were the jobs that I could think of at that point. And when, as I grew up, I didn’t know any lawyers like that other than ones I saw on TV, because my dad’s reward always, if I had perfect spelling quizzes for the pre quiz on Monday, was I could watch LA Law with him and stay up late to watch.

Those are the lawyers I saw. I wanted to be Grace Van Owen when I grew up, and that stayed the way as I got older.

Then in college, I double majored in English and Poli-sci and did my secondary ed certification. Except for my observation, that was the only piece my student teaching. Rather, I’d done the observation, did all the classes, but I didn’t do the student teaching. And when you graduate from Luther College in Decora, Iowa, with double majors in English and political science, you can go work on campaigns, you can go to law school, or those are the things I knew you could do, and I did both of those.

[00:03:36] Heather: Okay, well, so like me, you chose at an early age. Although I don’t think I was quite as young as you. My mom was a nurse, so I was the little girl who drew the crosses and wanted to be a nurse, but then within a couple of years realized, no, I don’t want to do that, and somehow picked law.

And no lawyers in the family either. Nobody around. And then my mom did meet somebody as I started to grow up who was going to law school, and so that piqued my interest even more. But it’s interesting to me to find out why people sometimes choose it in the first place.

But at least you had a purpose, right?

I mean, you didn’t end up in that place where a lot of attorneys do seem to end up, where they pick a degree that it’s hard to actually work with, and so they feel forced to go to law school. At least you had that kind of sense of I want to be a lawyer beforehand.

[00:04:26] Amy: Yeah, I think that that definitely made it easier. And so when I was a dean of students, when students were having troubles or considering leave of absence or just making small talk, I would ask them, what made you want to come to law school?

I think those of us who went to law school because we made a conscious decision, it’s sort of like anything in your career, right, where if you slide into it rather than deciding, there are advantages and disadvantages to each of those. And I certainly saw a lot of people who ended up – tons of student loan debt going crazy trying to study for exams and worried about getting called on all of the law school stuff because somebody suggested they should, or because so and so in their family was a lawyer.

I do think that there can be additional pressure when it’s something you grew up wanting to be. And then you get there and realize, oh, this reality may not be what.

[00:05:12] Heather: I thought it was going to be.

Intention is key

[00:05:13] Amy: But I always felt like it was easier for me in law school because I was there by a conscious decision, and I had had to work for it and fight for it. And it wasn’t something that somebody else I wasn’t living somebody else’s dream.

[00:05:27] Heather: Yeah, I think when you’re intentional about anything, it makes it a lot easier.

But of course, as you pointed out, sometimes we’re intentional. We think this is what we want, and then we do it, and we’re like, oh, maybe not, or It wasn’t what I thought it would be. Because I love how, you know, you grew up watching LA Law, and there are always shows there have always been shows about what it’s like to be a lawyer that have nothing to do with what real life practicing law is about.

So if you are a law student or somebody considering going to law school, I don’t know that there’s that many people who listen to this show who are in that boat. But if you are and you’re doing it because of that, no, you need to go talk to some real life lawyers, see what it’s really like. It still can be challenging and exciting and fun and interesting, but it is in a different way than what those shows make them out to be.

[00:06:17] Amy: In middle school. You had to go spend a day, like a career day, create your own career day, essentially. So I went and spent a day with a very unhappy lawyer in Iowa, and it was phenomenal because he was not blowing sunshine. Right. I mean, he was very unhappy in many ways. And I left it like, I can do this. If that yahoo can do this, I can do it.

And I think I went into it because based on one whole day, I thought, okay, well, there are some not awesome things about being a lawyer, at least particularly in the situation he was in. But it was really helpful for me to see this isn’t just having great clothes like Grace Van Owen and people falling through the there is there’s a lot that goes into it.

And that was really helpful for me to see, just like going and watching court where when you see some lawyers who they’re doing fine, and yet you’re thinking, these are not our world’s greatest legal minds, that was also really helpful for me to think, like, oh, okay, I can do that. If that person can do it, I can do it. So that was really helpful, too.

[00:07:23] Heather: Yeah, it’s not as polished and beautiful as it looks on TV. It doesn’t actually work like that in real life because people aren’t actually like that in real life. So, okay, you got out, you practiced.

You started in big law.

[00:07:35] Amy: Yeah, I started at Skadden Chicago in the litigation group.

[00:07:38] Heather: And how long did you stay in big law?

[00:07:41] Amy: Not quite six years, but over five. And I actually summered at Scadden DC, and then at another firm that has since been gobbled up in DC that was more DC, only more regulatory focused. They had like an associated lobbying shop with it, so more of a kind of a stereotypical DC firm.

So I split my summer between the two, and then ultimately my husband and I got married at the beginning of my third year and decided to stay in Chicago. And so I moved to Skadden in Chicago. So that’s where I started right after law school.

[00:08:13] Heather: How did you make the decision, okay, this isn’t for me, I need to try something else. Because you went into more mid sized firm after.

The move to a mid-sized firm

[00:08:23] Amy: I, and I know this sounds like drinking the Kool Aid, but even looking back all these years later, I can genuinely say that I loved a lot of things about practicing law at Skadden in Chicago, genuinely did. And some of the folks I practiced with are still very dear friends now.

For me, it became, I don’t want to be a partner at Skadden in Chicago at that time. Not that it was a guarantee or anything like that, but I was just looking ahead and seeing if I stay and things go well, I end up with this prize I’m not sure is right for me. And if I stay and things don’t end up going that route, I’m not sure what the role is.

I wanted to move to a firm where I could see myself being partner and having that fit with what I wanted for the rest of my life. So that was really the reason that I left when I did. And then I went to this midsize Chicago firm and was an associate and then made partner there.

[00:09:18] Heather: So I think there’s a couple of things that are in that that are actually really interesting.

Number one, there’s this assumption out there that big law is bad and it’s not y’all.

I mean, there are big law lawyers who are really not great people. There are solo lawyers like that. There are small and mid sized firm lawyers like that. Law firms are made up of people. And so in every organization, you’re going to end up with people you don’t fit with, you don’t like, who might be somewhat toxic.

But just because there are some people like that does not make the entire firm bad.

Now, sometimes there are firms that are more toxic because they allowed too many of those people to be there, right? So you have to be careful and really listen to your intuitive gut feelings when it comes to stuff like that.

The other thing I would note is your concept of it was a great place, but not the place for me to make partner.

And that is something that comes up for a lot of us that a lot of people don’t think about intentionally enough. I think that’s another area where just kind of slide right in.

As you said earlier, we slide right in on that path that’s made for us in that firm thinking, well, this is where I’m supposed to be because this is where I’ve been, and this is where everybody sees me without stopping to think “Is this the right place for me for that next step?”

Maybe it was the right place for me up to now, but what about that next step? And it’s important to analyze that regularly, because at some point, you may realize, you know what? I thought I wanted that, or, I was on the right trajectory, but something has changed, and that’s not the right place for me.

Or you learn more about what it means in that firm to be in that position, and you realize, no, I don’t want that. This is what I want. I need to find a better fit.

So, that’s when things become toxic for people without it being a toxic culture. Oftentimes what I find in my clients, and I don’t know about you, but I find the toxicity that people feel when they walk in the door is 80% or more related to the fact that it’s not the right fit for them at this point in their lives (as opposed to it actually being a bad place to work).

[00:11:33] Amy: Right. I think something that was really helpful, they do not do this anymore, but when I started at Skadden Chicago, three of us were sharing a partner office, and it was because they were adding floors or doing renovations or something. And at first, you think, I’m a big, fancy lawyer. I want to have my own office.

But it was terrific because I saw how one person was working on a ginormous bankruptcy, and he was doing a lot of chasing down executives who had become difficult to locate and dealing with a lot of document issues. And all three of us were in litigation, though, and another attorney in the group was working for a very different partner with a very different working style than the one I was working for.

And so seeing oh, wait, a lot of it comes down to the practice group. You’re mean certainly the firm, but the city, the culture it’s got in Chicago, I think it’s different than other offices might be the practice group, and then certainly the partner you’re working for.

And I was really fortunate that I worked with partners that really encouraged me and fostered my learning and development and my growth. And some of that was intentional when I realized, oh, this partner is doing this work that I’m really excited by, and I’m not working for her, and I’d like to.

And so then I volunteered for a pro bono project that she was heading up, and then that ended up meaning I ended up getting a lot of my billable client work from her, and that was great for me.

The Lesson: Be Intentional About The Work You Do & Who You Work With

So, I think some of it is not just saying, oh, I’ve been assigned to this group and this partner. Some of it is saying, I might like to work for other people, and so how do I get to do that? And so those things were really helpful for me and having a great experience there.

[00:13:12] Heather: Yeah. And again, you’re not just sliding by based on what everybody else is putting, like the boxes they’re putting you into, the things they’re giving to you. You actually get to be intentional.

This is something I think a lot of younger people really miss. You can be very intentional about the work you do, the people you work for. Maybe not the first 6, 9, 12 months you’re there. But you can be pretty quickly thereafter.

And there are ways to do it that are politically correct and done in a way that is going to be seen as a positive, not a negative. There’s better ways to do it than others, so just be really aware of that.

Make sure you’re being intentional about the work you’re doing, the people you’re working with, the practice group you’re in, the clients you’re working for, everything.

Because that is honestly the key to being a happily successful lawyer as opposed to just successful on paper.

[00:14:06] Amy: So a female partner I worked for, Tina Chen, she would often say, no one will ever care more about your career than you.

[00:14:13] Heather: Yep.

[00:14:13] Amy: And the first time she said that, I thought, but you’re my mentor. What do you mean? And now I realize, absolutely.

Taking Ownership of Your Career

So often we work with clients on the one on one or small group coaching side of our business, working with attorneys in their careers, where you say, okay, how did you end up at this firm? Well, this thing sort of happened. Okay. How did you end up staying as long as you did? Well, I didn’t really have another offer, and that’s completely normal and natural.

And until you have retired, you have time to do a reset. But the quicker you can realize that you need to have ownership in your career and that as wonderful as your mentors and other people you’re working with may be, their top priority is not your long term success. It just isn’t. So the sooner you can come to terms with that and take ownership, the happier you’re going to be.

Case Study on Taking Ownership  (& What’s Possible)

[00:15:04] Heather: And that’s something that I think we think we’re taking ownership, but yet we’re not. And so I’m going to give an example before we move on, because I think this really clarifies it.

I have a client who came to me about two years ago and was really upset with not having been made partner. And as we were talking, it became very clear that he thought, well, I checked all the boxes of the written rules, right. And I’m like, okay, well, but what about the unwritten rules?

Well, what do you mean, the unwritten rules? There are always unwritten rules, right? And so we went through it and we started realizing there were some leadership things, there were areas of improvement for him.

And also, maybe it was good that he wasn’t made partner because it wasn’t the best fit for him. Because it wasn’t the best fit, he wasn’t showing up in the best way he could and it was probably being seen by others.

So fast forward two years and he actually went to a very small firm from kind of a mid sized firm, a firm that proactively told him, we will let you do your thing. You can build your own book. You can do all which was really scary because he was kind of out on a limb on his own. But it gave him that opportunity and he did it.

And not only did he do it – and of course we worked together and I helped him do that – but this is him taking intentional action in ways he had never done before. Proactively taking control. And at first he was scared to death, right? Like, oh, I can’t do all this. I’m not even named partner. Yes, you can. I promise you can.

And so he did the thing. Well, then, now he is transitioning to another firm because- we always said that firm might be a stopping point. It is your opportunity to do the things you want to do, but it’s small. And he realized very quickly as his business started growing that it wasn’t the best place for him to stay because he had bigger visions for his practice than what they could grow to at that place.

And so now he’s moved into an amazing opportunity as a partner, doing the things he wants, getting paid what he wants with clients that he wants, and that in two years time, simply by taking ownership and realizing I can make more intentional actions, I’ve been just going with the flow, going along with what everybody tells me what to do without realizing. No, there’s more to it than that.

Not only will you achieve more that way, but you’re going to be a lot happier in the process.

[00:17:25] Amy: Absolutely.

Happiness Comes From Risk

[00:17:27] Heather: That’s where I find most people mess up is they don’t realize that’s how the happiness comes. By going out on the limb and doing those things and taking a chance because you are not just taking responsibility and ownership, but you finally feel like more independent and free, if that makes sense.

[00:17:47] Amy: And again, if you want to build a long term career, it’s important to have those things.

[00:17:52] Heather: Yeah.

[00:17:52] Amy: And I think sometimes when people practice law for a long time, and often in very high stress environments where your skill set is being challenged regularly and you’re not always feeling like you quite measure up.

I think it can be easy to forget that you actually are worth having a career that makes you happy. Not every day, every moment, because that doesn’t exist, right? Unless you’re just riding unicorns around all day. But it can be really easy to forget that there can be happiness in your career that it is worth working toward and that you can get there.

[00:18:32] Heather: Yes, absolutely. Okay, so you left big law. You went to a mid sized firm. You became partner.

You did well, but you left eventually to do something else. So how did that change happen?

[00:18:47] Amy: So I was selected to do a fellowship in Europe for four weeks through the German Marshall Fund, which picks emerging young leaders.

People under 40 essentially can apply or be nominated. And I got to go do this amazing experience visiting five European cities with other Americans. And my schedule was built so that I met with lots of different lawyers.

So I met with a former lawyer from Philly who was working as a war crimes judge in Bosnia. And I met lawyers from the US. Who were working at NATO and doing all these really big things.

And I had second chaired an $18 million jury trial where we’d gotten some patents thrown out, like it was a huge success, right? So I had done another bench trial. I had done all the things I was supposed to do. I had taken plenty of depositions. And yet, as I met these lawyers during my fellowship, I kept thinking, gosh, these are really big things, and what am I doing?

And so I came back, and right after I got back, there was a reunion or alumni event for my law school to meet the new dean. And I met the new dean at that. And there were some changes in personnel with the new dean coming in. And one of those was that the dean of students decided to leave. And several people who I saw at that event and then later on reached out and said, hey, you should apply to be the dean of students at the law school.

Every time I laughed and said, I’m a law firm partner. Why would I want to go do that?

And I was on the alumni board of governors and very involved in alumni things for the university. So this kept happening. And after a couple of months, finally I decided, why not? Let’s just see.

I sat down, and I wrote my cover letter, and I showed it to my husband, and he said, there is a big problem with this cover letter. And I thought, oh, yikes, I haven’t done this for a while. Maybe I’m out of practice. And he said, if you submit this cover letter, you will get this job, so you better be sure you want it.

And I went to submit, and I got kicked back by the system because I didn’t have all the things they wanted you to have. And so I reached out to the head of the search committee who I did not really know, but she’d had me speak for a couple of panels, but I didn’t really know her. And I said, hey, people said I should apply, but I can’t because I don’t have these things. And she was like, check the boxes you do. And she helped me think differently about some of my experience.

I submitted and as I got to know the then new dean, I realized what a great opportunity it would be to work alongside him and really have the opportunity to help law students avoid some of the mistakes I felt I had made in practice. So I really found myself focusing my time at the law school on developing leaders among law students and developing professionalism. I did all of the student counseling and planning, orientation, planning, graduation, those sorts of things.

But I also really devoted a lot of my time and energies to creating sustainable long term leadership and professionalism development for law students.

[00:21:42] Heather: Which translates really well into where you are now, right?

Into Leadership Coaching

[00:21:46] Amy: Yeah. So I kept asking law firms to pay for these things for law students. I had a deal with the dean and the deal was that if I didn’t ask him for more budget money, I could have pretty free rein as far as programming. And so I kept asking law firms to pay for the things that I wanted to do so I didn’t have to ask the dean for money.

I kept hearing from law firms, gosh, this is great, you’re working with the business school, you’re doing all these things. I wish we were doing that for our lawyers. And I started contemplating leaving the law school quite a while before I did and had some interviews with law firms to go in, do professional development.

Two interviews in a row, I was told they would save money if they hired me. And by the second interview I was confident enough to ask what they meant and they said, oh, well, we hire consultants for a lot of these things and they cost a lot more than your salary would be. So if we hired you, we wouldn’t have to hire those consultants because you can do all these things.

And I thought and then the interviewer actually said, frankly, I’m not sure why you’d want to have a job instead of doing this on your own. Do you just need health insurance?

I was like, well that’s different. So I decided to get my coaching certification and then my husband got his coaching certification at the same time. And we launched our business initially really focused on career development and transition for lawyers, and then added the team and leadership development later on when we both got additional certifications in team and leadership development.

[00:23:17] Heather: And team and leadership development to me is something that is so important, yet so few attorneys focus on or even think about.

[00:23:26] Amy: Right.

How To Become A Better Leader – Why It’s Important & How To Get Started

[00:23:26] Heather: I mean, we all know, I think I said this before we hit record. We all know those attorneys. Maybe we were once one of them. Or are some of them you out there listening are one of these people who believes that’s not my role. I don’t need to be a leader, it’s not my job to develop others in that way other than teach them the very basics of what they need to know. Right? To how to do this thing.

And that’s just not true in my mind. Certainly not if you want a really good practice that evolves, that supports you without taking so much away from you. Because a team is necessary. To really thrive from a monetary perspective without killing yourself.

And I’m so shocked. We lawyers often think about money. I mean, we’re very money driven oftentimes. And yet we don’t put two and two together and see how important the leadership is and the development of others is to actually making more money.

[00:24:32] Amy: And having the life you want. Because if you want to get to your kids soccer game but discovery has to go out, you have to have somebody that you have developed and trained and can trust who’s going to get it out.

So we have different ways we work with lawyers, some of it’s one on one, some of it’s in small group attorney masterminds that are very much focused on career development and leadership.

Becoming A Better Leader Starts With Investing In Yourself

And we will have lawyers who say, well, if the firm isn’t going to pay for it, I’m not going to do it. And that just shows right off this misunderstanding.

Why would the firm help you learn how to grow your book? Of course they want you to grow your book enough so that you’re contributing, right. But they don’t want you to leave. And if you leave, you’re taking that skill set.

The firm didn’t pay for you. They didn’t pay your law school tuition either, because you’re getting the law degree and you’re hanging on to those skills that you learned.

And so for people who say, well, if the firm wanted me to be a great manager, I’m sure they would have a program or training for me, it’s like, no. And I think a lot of times attorneys also think I will make partner or make 50 or whatever the target is. I’ll get to certain level and then I will learn these skills.

And the reality is, if you’re suddenly a fifth year and you’re running cases and you’ve got a lot of people you’re supervising, it is much harder if you haven’t been actively supervising, say, the legal assistant who’s been on your other cases, right. You’ve got to build those skills and no one’s going to put you in charge of the team of 20 if they don’t think you can do it.

And the way that you show you can do it is by learning how to do it and demonstrating that with smaller teams as early in your career as you possibly can.

[00:26:14] Heather: Yeah, with one human and then a team of two. And then I love that you’ve pointed something out that is a huge pet peeve of mine. And obviously you run into this, too. This whole, well, if the firm won’t pay for it, then I’m not going to do it. And this is, by the way, I don’t know, you probably work mostly with big law or bigger firms.

This is one of the biggest objections I get to hiring me when it comes to big law attorneys. I almost never hear that – and in fact, solo attorneys, small firm attorneys, people who own and have built their own practices, who frankly, may not be making as much as some of these big law attorneys are making or have been making for a long time – they do not bat an eye to paying for this stuff.

But there’s something about these big law and bigger firm attorneys, I think because the firms pay for so much for them that they think they shouldn’t pay for this.

It would be nice. I agree if they would. And I do think law firms need to support their attorneys more in other ways.

But at the end of the day, you are in charge of your own career. You are in charge of your own professional development. The firm would love for you to excel and they want to support you, but there is only so much they can do. Like, let’s be honest, they cannot pay for every single attorney in their law firm to be coached, to join a Mastermind, to whatever it is the expenditure is for your own professional development.

And many law firms have programs where they assist, or they do for some people, but it is more limited, right, because they can’t do it for everybody. They just can’t. That’s not financially viable.

The Results Are Worth The Investment – If You’re Ready To Do The Work

And it’s so worth it. Like, good God, think about how much more you could excel and how much more money you would make. Not just for the firm, but for yourself.

[00:28:10] Amy: If you do these things for yourself, it is amazing. We were just talking about a particular client the other day who she came to us. She’s an in house lawyer. Her company would not pay for her to join our six month Mastermind program. She paid out of pocket. She ended up not quite and I feel like I should have one of those disclaimers, right? Like the Micro Machines guys should say, results not guaranteed.

[00:28:37] Heather: Right?

[00:28:37] Amy: But she ended up almost getting a signing bonus. It was almost as much as her entire salary had been because she was vastly underpaid. But before she started working with us, she didn’t have the confidence to say it. So she switched jobs, her salary then. So in addition to the signing bonus, her salary was a steep increase.

More than doubled her salary. Really, and no longer needed to go in every day. I mean, lots of changes that made the job work better with her life in addition to the comp. And if that’s somebody who if you can do that for whatever the pittance is by comparison of working with a coach, whomever it is, or joining a mastermind group, whichever one it is, why wouldn’t you take that deal all day?

I think a lot of times people have trouble betting on themselves.

[00:29:31] Heather: I think that’s what it is. It’s not the money. What I’ve come to realize over the last couple of years, and I push back when clients say this, I’m like, this is not 98% of the time, it’s really not about the money. There’s a few occasions where maybe it is, but it’s about…

They’re afraid that they won’t see the results. They’re afraid. They fear. And I get a lot of people that when it comes down to it, well, I’m just not sure I’m willing to do what it takes. I’m not sure I’m willing to do the work. Okay. You need to figure that out.

Number one, I do think you’re overestimating the work involved oftentimes. But maybe you are not in a place where you’re ready to go there and do that. We have different phases to our life and circumstances going on. And so maybe this is better for you in a couple of years or I mean, there are things to think about, but you need to get honest with yourself about what those things are.

So again, we talked about this before.

You can be very intentional about your choices and where you want your career to go and what you want it to look like.

[00:30:32] Amy: Absolutely. And I think some of it is thinking through, I don’t know the best way to put this, but we have a lot of clients who tell us that working with us helps them get their mojo back.

[00:30:45] Heather: I hear that same phrase from clients. Isn’t that weird? That must be a very lawyerly thing.

[00:30:50] Amy: Yeah, sometimes I think it is.

Invest In Yourself To Set Yourself Up for The Future

We’re sort of sitting in Oatmeal, right. And it’s enough.

It’s fine. It’s not spectacular, but it’s fine. And there are times in your life where fine might be the best fit for you and your family or whatever your situation is.

But if you want to move beyond that, you should look for whatever help is the right help for you, whether that is you need to hire a personal trainer because that’s going to give you more energy. And whatever it is right. It isn’t necessarily working with a coach.

Maybe you need to start spending time around more positive people. And that’s certainly a benefit from a mastermind, but that also can be a benefit of stopping listening to your sister who just wants to whine all the time.

There’s different ways to do that. And whatever it is, you just have to decide how important it is to you at this moment and what do you need to work on now. So you’re setting yourself up for the future.

Why To Work On Your Leadership Skills

[00:31:48] Heather: Yeah, absolutely. Okay, so when we get into the specifics of leadership and being a really great leader, especially one who works to develop others, what’s the point of that? Let’s break this down into – because we know lawyers like to see, how would this actually benefit me?

So, what’s the point? Why do they want to do this?

[00:32:10] Amy: Well, one of the things that we hear a lot is because people are sick of doing everything themselves.

And so when we talk with one of our mastermind groups or work with a client or even in a corporate setting, when we’re talking about delegation, supervision, managing, a lot of times it’s because people are sick of doing all the work and they want to be able to know that they are logging on to yet another interminable meeting and something’s being done.

And that might be because they have learned how to give clear direction, they’ve learned how to develop a staff member, or it might be because they have learned how to talk to their significant other and get them going on tasks. Right.

So I think a lot of it is because they want to have more time and they want to have less stress and conflict because it is so incredibly I mean, we’ve all had this experience. You ask somebody to do some work, they don’t do it on time, they don’t do a good job, and then there’s this conflict that erupts within yourself and or with that person about how much do I point it out? How much do I push back? Do I just do the work myself? All those sorts of things.

The more you can avoid that, the less stress you’re going to have, the happier you’re going to be both at work and outside of work.

How To Become A Better Leader: Where To Get Started

[00:33:21] Heather: Absolutely. And so, okay, that’s the why. So where would you say if somebody is like, okay, I see that I need to be a better leader. I’m not what’s a good starting point for them? Where should they start?

Be Intentional

[00:33:33] Amy: I think the first place to start is really to think about being intentional. And so some of that is, all right, I have called a team meeting because we said we were going to have team meetings every week on this case. Team.

How do I want that meeting to go? How do I want to show up? We do a lot on executive presence, and the first step is really thinking through, do I want to come across as flustered and crazed? Do I want to come across as on top of things? How do I want to come across? So that’s number one.

Be  Clear

I think another thing that can really make a difference very quickly is to be very intentional about how you’re giving assignments and the clarity with which you are giving assignments. Because we were all that person, that first year associate who was told, I’ll go find that Smith case from 1975, and it turns out that the site is actually to the Jones case from 1982. And in the meantime, there went your whole weekend.

And so putting yourself back in the position of the person that you’re giving instructions to and making sure not just the exact task, but the level of delegation, the deadlines, all those sorts of things, really, you need to be clear on.

Follow- Through

And we often use the five behaviors of a cohesive team model or pieces of it when we’re working with teams. The bottom of the triangle for the five behaviors is trust. And even if you’re just supervising one person, you have to have that trust there. One way that you can build that trust, there’s lots of things you should do to build that trust. But one way you can build that trust is by being clear and following through.

If you say, I need to have that assignment from you by Wednesday at 09:00 A.m. Because I have a 10:00 A.m. Meeting, don’t give a false deadline because you’re destroying the trust.

[00:35:22] Heather: Right.

Be Honest

[00:35:23] Amy: So you need to or just say, I need it by Wednesday, 09:00 A.m., that’s fine, but don’t make up a meeting that doesn’t exist. And we see that a lot when people are trying to be firm and trying to push people who aren’t good at meeting deadlines, and it ends up eroding the trust that you need as the basis for a great relationship within the team.

[00:35:39] Heather: Yeah. And there are ways, if somebody isn’t meeting your deadlines, to then approach it and deal with it that have nothing to do with lying to them about the why. We all get annoyed with clients who do that, right, who make up false emergencies.

Or the worst of the worst are the ones who know about it forever and then don’t say something until the last minute. And sometimes they wait because they want to have control over what the timeline is. We’ve all had those clients. So you don’t want to be that person because you will destroy your trust.


And I would actually say, too, and I don’t know how much you guys go into this as well, but something that comes up a lot in my coaching when it comes to delegation and leadership is systematizing as much as you absolutely can. And this is something that lawyers just do not do, and I don’t know why.

Now, we all have some systems without even knowing we have them. But being very here’s that word again, intentional about the systems. When you are giving a project, you could have a system for how you explain it or the things you need to think through so that you can be clear. Right. So you can have your own internal system and then a system for how they need to go about asking questions and going off and doing things and then when to come back.

There are even systems you can have in place for how to do the thing right. That is the best way to have clarity of what needs to be done, what needs to be delivered, when it needs to be delivered, all of that. And then also you will get better work product, which will allow you to then let go more and not worry about will they do this right? Will they get it back to me on time? Will they? All of that stuff.

That’s something that by the time this interview airs, I will have talked about systems more fully, and I have an actual framework checklist for it. So I’ll have to put a link in there to the show notes. But I saw you nodding. So you guys do go through that as well.

[00:37:30] Amy: Absolutely. And the more you can take the guesswork out of it for everybody involved, you’re making so many decisions all day long that I think the more you can take out the guesswork, the more you can then focus on the actual work.

And rather than the associate wondering what you’re meaning or the outside council wondering what you’re meaning and what you’re thinking and trying to fill in the blanks, because that’s where so much conflict comes, where people are just they’re doing the best they can, but nobody’s a mind reader.

Ask The Right Questions

[00:38:00] Heather: Yeah. And I do love that you started with two things. One was to check in with yourself, really, and understand: How do I want to approach this? How do I want to show up?

Which we often don’t do because we think, well, there’s no time, right? I’m rushing from one thing to another. I have this meeting, I’ll just go in and wing it because I don’t have time to prep for it. But if you took just five or ten minutes to think through these things and jot down:

  • Your meeting would go so much more smoothly.
  • You probably wouldn’t spend as much time in the meeting.
  • And you wouldn’t have as many questions after the meeting, which means less interruptions.

There’s a huge ripple effect by not taking that five to ten minutes ahead of time that I’m willing to bet adds hours to your day or week that you wouldn’t have to add. Right?

Pause & Plan Ahead

[00:38:46] Amy: Right. And I think this has been a problem with remote people – being remote. Even if you’re just walking down the hallway to a conference room, you have a minute to think, what are we talking about? What is the goal of this meeting? Versus if you’re just sliding from one zoom to another, then you’d never have that pause to think, about what was my intention.

So one of the things that I like to do is the night before, when I’m looking… Well, on Sundays, I do my weekly preview.

I try to think through the beginning of the week what my intention is for particular meetings or whatever. And then the same thing the night before when I’m looking at my calendar for the next day, think through how do I want to show up for that and what’s important for that meeting to achieve. And I think if you can take that pause, you’ll get better results and you’ll be happier doing it.

[00:39:38] Heather: Absolutely. And I would say you could do it the night before or the morning of, but just I do the Sunday night before for the whole week. And then every morning, my first ten minutes is, here are all the things, here’s what needs to happen today. Here’s what my calendar looks like. Boom, boom, boom.

And I think through it, and sometimes it takes five minutes, sometimes it takes 15, depending on what’s on tap for that day. But I guarantee it saves so much time and energy later.

Take the time. You have the time. You can make the time, I promise, because it will save you time in the long run.

Okay, so time is often one of the biggest roadblocks that we coaches hear about. When you are going into this type of coaching or in your mastermind with people who are trying to become better leaders, wanting to develop other people.

What are some of the objections – or excuses? There’s a lot of words you can make for it. Right? What are the other kind of things that come up that get in the way for people being able to do this?

The Things To Address To Become A Better Leader (That Are Currently Holding You Back)

Authority Gap

[00:40:41] Amy: I think sometimes there’s the authority gap between what people think their authority is and what others think their authority is.

This happened to me when I was an associate at Skadden. I was running a whole bunch of litigation for a big company, and the local council were often partners of well known law firms. They weren’t necessarily solo shops or anything. And so some of those partners at well known law firms weren’t excited about taking direction from a fourth or fifth year associate. I knew I had the authority from the client. I knew I had the authority from the partner I was working with, but they didn’t understand that.

And so the solution there was the general counsel actually did a call with all of our outside counsel, and he went through a number of things in terms of what our strategy was, why we’re doing things the way we’re doing, and also said “And by the way, Amy is the quarterback on all of these cases.” That then transferred, sort of officially transferred the authority, and many of those issues went away.

And I think that’s something that particularly women can run into where people are thinking who is she and why is she giving me direction?

[00:41:56] Heather: Right?

[00:41:57] Amy: And that can be a roadblock.

Seen As A Friend (Not the Boss)

I think another barrier to being a good manager is this issue of how do you we often call it the from bud to boss conundrum. And so we often do workshops with mid level associates or mid level leaders in corporations about how do you go from being the friend to being the supervisor and stepping into that leadership.

That can be tricky and I think it’s frankly, I think it can be trickier for women and there can be additional things that go with that and so that can be hard of how can you be friendly and still friends outside work? Probably – maybe not – but be the leader and being directive, giving feedback. And sometimes we don’t do things that we need to do to be good leaders because we think we’re being nice.

Remember Clear Is Kind, Unclear Is Unkind

So I always go back to the Brene Brown of clear is kind, right, unclear is unkind. And if you are not giving feedback because you don’t want to hurt somebody’s feelings, you are not really helping.

[00:42:58] Heather: I struggled with that. I remember when I first made partner, I had a lot of issues with a couple of people who were just a couple of years below me who had seen me as a peer right up until I made partner and they weren’t partner yet. And all of a sudden I was running stuff in a way where I hadn’t before. And you kind of assume people will just fall into the right roles but they don’t.

Sometimes you have to be very careful because they perceive you differently without you having done anything different, right? And you can’t just go up and be “friends” like you were before. At least not when you’re running the deal or the case or whatever it is.

You need to step back and say, okay, what is my current role, where was it? What’s the gap here? How do they perceive me now? And address it and address it correctly. That can be tricky but it’s addressable.

[00:43:58] Amy: And I think people would probably be surprised. So half of our business is working with lawyers one on one and in our masterminds and intensives. And then the other side of our business is the team and leadership development in corporations and law firms.

I think people would probably be surprised at the number of times we go in to work with a very successful by any measure team and discover that there are conversations that should have been had ten years ago that have not been had or conversations should have been had two months ago, right?

My dad used to always say don’t treat me like a mushroom, don’t keep me in the dark. And I think about that a lot that we need to be willing to stop treating people like mushrooms and start having the actual conversations, be willing to be vulnerable and have those difficult conversations so that then everyone can move forward.

Because it doesn’t get better with age. Right? It just festers. And we have seen time and again that even though lots of metrics may be going well, people’s overall happiness at work and their overall engagement at work really suffers when things are being left unsaid.

Be Honest With Yourself About How You’re Perceived (And Don’t Make Excuses)

[00:45:08] Heather: Absolutely, it does. And I recall back – this is right before I made partner – there was a comment that was made to me by the managing shareholder of not only my office, but he was kind of in the region and he was kind of a big wig within the firm. And he said something to the effect of, you’re known for having a sharp tongue, which was interesting because I never cussed.

And in digging a little deeper, I took offense to it initially.

A lot of people who I told that to, especially women, immediately were, oh, that’s just bull. Men are worse. You’re not like that. It’s because you’re female. And yet I couldn’t shake that.

Well, I do know I am bluntly honest, and I think that’s where it came from more than anything. I’m bluntly honest, and I sometimes say things people don’t like to hear. So what does that mean for me, right? What does that mean for how I can’t change how I’ve been perceived in the past, but perhaps I want to change how I’m perceived moving forward.

And instead of I could have done the typical, it’s just because I’m female.

[00:46:10] Amy: And blown it off, which is what.

[00:46:12] Heather: A lot of people do, by the way, because there’s some truth to it. I decided, you know what? I don’t know that I want to be known that way. I need to address this, and here’s how I’m going to.

I’m still bluntly honest, but I am more careful about how I put forth that honesty. And I’m much better about stepping back before I do it and being more intentional and making a plan and ensuring that I do it in a way that is meant to be kind, to help to move someone forward and make it very clear so that I’m not known just as somebody who has a sharp tongue.

[00:46:48] Amy: I can definitely relate to that. And when I was at Skadden, there was a time where we were producing communications. Opposing counsel was forcing us to produce some internal emails between us and the clients, and we had redacted them, of course, as privileged, except for parts that were not privileged.

And opposing counsel actually demanded that the judge review them because he was sure that the fact that it never said, like, hey, Amy, how are you? How was your weekend? And then turned to business and know, a sign off that wasn’t apparent to him. That meant that we had over redacted, and the judge took the emails back into our chambers and came back out and said, no. It appears that that actually is how this team is communicating with each other.

And I think about that sometimes because I do think that every team has norms. Every firm has norms. Every corporation has norms. And so you have to understand what those norms are. And certainly as I move through my career from big firm to mid sized firm to top law school to I worked for a national legal nonprofit, working with lawyers, judges, and law students across the country. And then in our business, those are different environments. The way I’m going to start an email to the managing partner of a law firm that we’re working with in Texas might be different than the way I start off an email to our social media person, right?

Know the Context To See The Gift of Feedback

You want to know the context. And I think you were really smart to be so thoughtful and think through what does this mean? And not just have the knee jerk. Because sometimes we get feedback that’s difficult to hear. And it does not look like a gift.

[00:48:25] Heather: Right?

[00:48:25] Amy: It looks like something we want to give back. But it really can be a gift if we can evaluate the value of it and the source of it and consider, what do I want to take from this? And sometimes you don’t want to take anything from it.

[00:48:40] Heather: Right.

[00:48:40] Amy: And other times you want to make a course correction, which is what you did well.

[00:48:43] Heather: And here’s the amazing thing. That gift continues to give because it’s always there. I’m always thinking about it, and it helps me when I’m parenting. It helps me in my coaching. It didn’t just help me then in dealing with associates or paralegals or staff or clients. It did, but then I’ve taken that and it’s continued to help me. So I think a lot of times there are gifts in them if we’re willing to see them, for sure.

Be Open To Feedback (Which Starts With Trust)

[00:49:13] Amy: And I think you have to have the trust built up within the team so that people feel willing to come to you and give you that feedback. And when you do have a day where you send a sharp email that you don’t want to sound so sharp, if you have the relationship built up, then it becomes, oh gosh, Heather sounds a little grumpy. Must having a stressful day instead of, oh, Heather’s a witch.

Because if you have a relationship that forms a foundation, then well and even.

[00:49:43] Heather: Then you might have a relationship where they come back into, hey, is everything okay? Because that email sounded a know, and you’re like, oh, didn’t mean for it too. Thank you for letting me know. So totally changes the dynamics of the team when you can get to that place.

[00:49:58] Amy: Absolutely.

[00:50:00] Heather: Okay, before we let you go, do you have any final words of knowledge or like, if there’s just one thing that they take away from today’s conversation? What do you want them to take away?

It’s Not Too Late To Learn How To Become A Better Leader Or Build The Career You Want

[00:50:10] Amy: I think it’s that you can build the career that you want, and it is not too late to make some of those course corrections. Whether it’s moving to a different work environment or changing the way you’re approaching a piece of the work that you’re doing now in the very same place that you’re in. It’s never too late to become intentional about where you want your career to go and to take action so you get there.

[00:50:35] Heather: Absolutely. I would 100% agree with you on that one, and I think it’s the perfect message to end on. Thank you so very much for joining us today.

[00:50:44] Amy: Thank you for having me. And I just want to say anybody who’s listening should feel welcome to reach out to me on LinkedIn. If you want to set up a one on one call to talk about your team or a situation that you’re in, I’m always happy to do that. And we actually have a link that I think you’ll have.

[00:50:59] Heather: Yes, in the show notes – I will have all the links there.

[00:51:02] Amy: So people can feel free to reach out if there’s anything I can do to be helpful or you just need somebody to vent to. Heather and I have certainly been there and always want to support other lawyers.

[00:51:12] Heather: Thank you so much for joining us today.

[00:51:15] Amy: Sure. Thank you for having me.

About Amy Gardner

Amy M. Gardner works with law firms and corporations to reengage teams and help them thrive by utilizing a proprietary Team Driven Leadership approach to build leadership skills, improve relationships, strengthen emotional intelligence, have difficult conversations, and more.

Her work with teams and lawyers draws on her unique experience as a former Big Law associate, partner at a mid-size Chicago firm, and dean of students at the University of Chicago Law School.

Here’s how to connect with Amy: