Asked & Answered: Ashley Smith on owning your career path

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“It’s easy in a law firm, especially when you are an associate, to forget about the autonomy and control you have over the direction of your career,” said Ashley Smith, who is entering her eighth year of practice.

In April, the NALP Foundation released an updated report on associate attrition rates, indicating that 2024 marked the second straight year that associates continue to exit firms before the five-year mark.

According to their sample pool, of 6,092 hires, 4,125 associates departed from 119 firms across the nation and Canada. The trend places further pressure on firms to rethink retention, mid-level associate career development and the traditional six to seven-year partnership track.

“I encourage other mid-level and senior associates to really feel empowered, to voice what it is that you want. Work with those individuals who are going to help voice those things and really put yourself in the position where you’re owning that it is still your career,” Smith said. “Sometimes it can feel like as an associate you don’t have that power.”

Smith is a senior associate with Michael Best & Friedrich, practicing from the firm’s Milwaukee office. A graduate of Marquette University Law School, she focuses on aiding clients in the corporate law space with matters contract drafting, mergers and acquisitions, corporate restructurings and governance. Smith is the past president of the Wisconsin Association of African American Lawyers, a member of the Marquette University Law School Alumni’s Board of Directors and of the State Bar’s Business Law Section’s Board of Directors. She is a four-time honoree of the Top 40 Under 40 Black Lawyers of Wisconsin distinction by the National Black Lawyers organization.

The Wisconsin Law Journal sat down with Smith to discuss the middle years of a legal career where she offered advice to those following behind and perhaps to those senior to her.

WLJ: What inspired you to start a career in the law?

Smith: When I was in college, I started my freshman year in 2011. It was right when the legal industry hadn’t bounced back from the 2008 market crash. I initially didn’t pursue law. I actually thought I was going to go to medical school to be a psychologist. As I went down that path, while I love the STEM fields, I quickly learned that’s not where my interests lie. It was about my junior year that I took a hard look at myself and what skills I had and what kind of profession I thought I’d be really good at. I’d always considered the law, but not to this degree. Then I went all the way in. So, it wasn’t like I grew up always knowing that I was going to be a lawyer.

WLJ: So, now you’re at a point in your career where specialization and specific practice focuses are starting to matter more. How have you decided where you want to lean in and where you want to pull back?

Smith: I’ve been practicing for about seven years. I think I really started to narrow this two years ago when I was at the core of being a mid-level associate. For me, I wanted to pick areas that complimented each other, but also that I enjoyed. I love doing deal work. I feel as the corporate attorney on an M&A deal, you have to be a jack-of-all-trades from an issue spotting. You have to know enough to be dangerous in a lot of substantive areas of the law. If nothing else, I always had to stay sharp. Think about areas like data privacy and cybersecurity that are constantly changing, and new laws are being incorporated. I have to be able to know enough to know when to and also to bring in my colleagues to serve in that area as the experts.

I really love working with start-ups. I’m attracted to how they are not as risk adverse as lawyers. They are so passionate and excited and see the vision for their business. I think it’s inspiring in a way. I knew staying active and working with clients in the venture space was going to be important to me just because I love that population of clients. I have experience on both the investor and company side which I think is important so you can always have a full scope of the considerations, regardless of who you’re representing in the moment.

The last piece, I just find contract drafting a fun exercise. Lawyers are forever learners — you kind of half to be. The exercise of drafting a contract is like a puzzle. I really like helping clients negotiate their commercial contracts. I like the exercise that my brain has to go through to negotiate the agreements.

WLJ: At this stage in your career, how are you stepping into more strategic roles for yourself and your career vision?

Smith: In my experience, around right now — seven, eight years of practicing — when you are approaching that serious consideration of partnership, partners really want to understand what your long-term goals are. What has been exciting for me, and I don’t think people really realize this, there’s a lot of opportunity to change what your career looks like within a firm depending on where you are in your life. Currently, I don’t have any kids. I have a partner, but the demands on my time looks a little different than if I were to have a growing family. I can prioritize my career in a way that I may not always be able to when I start to grow my family. For me, it’s having those proactive conversations. In my experience, partners want to know what are your goals, mostly because they are open to sharing about their journeys to partnership. They want to share what their life looked like when they pursued that opportunity. Even if you don’t want to be a partner, at Michael Best, we have a special counsel role. Or if you do pursue the partnership, what does that look like?

WLJ: So, how have you approached defining success for yourself in these “middle years” where you’re not quite a partner but also not a fresh associate?

Smith: What’s helpful is being at a place like Michael Best where they really define what that looks like for you. They have something called a skills inventory for the different practice groups including the corporate, M&A space and it identifies for you what skills you should have at this stage in your career. Everything is always subject to what projects are actually available and general staffing at the firm, but it helps really guide you. Sometimes, you don’t know what you don’t know. I think as you become more senior you have a better idea of what the expectations are — especially when you are transitioning from a more junior associate to that mid-level — you always want some kind of tangible checklist that you can follow and say, “okay, I can do this,” or “this is an area of growth for me.” It’s really nice to have something like that available so when you are having or preparing for these discussions, you have a chance to be proactive.

WLJ:  Mentorship tends to shift during these years. Have you found yourself, specifically, moving between being mentored to mentoring others? What have you learned from being on both sides of that dynamic?

Smith: Being a mentor, I try and make myself available, you know? I probably offer a lot of unsolicited advice. I always approach it from a place of I want you to be successful, and this is what I do or if you don’t like how I do something, I suggest reaching out to so-and-so and see how they do it. Please take my advice with a grain of salt. I think it’s both being proactive about providing unsolicited advice but then also creating a space where younger associates feel comfortable coming to you with questions. That’s something I really pride myself on. It’s just making myself available and also appropriately inserting myself where I think it would be helpful.

Getting mentored, I think it’s the same way. With only being at Michael Best for a year and a half, the mentorship that I have received has far exceeded my expectations. When you start to become more of a senior associate, the mentorship is so very important but it’s really the sponsorship that’s going to help elevate you and support you when those conversations come up about you becoming a partner in a law firm. For mentorship, I’m the exact same way. I flip the script. I try and figure out what someone’s communication style is. I know how busy our schedules are, so I try and set up some kind of regular cadence where we’re checking in. I try to create interim goals for myself and make it a very candid relationship. I want to know how you are building business, what are the expectations for me. I have found it valuable to have mentors who, especially when we’re talking career-wise and for growth in a law firm, you feel comfortable going to that does the substantive work that you do. They can really provide you a lot of insight on trajectory than if you’re being mentored on a regular basis by someone who doesn’t substantively do what you do every day. It’s going to look a little differently. I definitely have mentors who help navigate different responsibilities to your family or having leadership in the community. There are so many people who serve different roles. I think it’s super important when thinking about growth in a law firm to have someone to provide that direct feedback.

WLJ: What have these middle years taught you about what kind of lawyer you want to be? And has that picture changed or shifted direction from when you first started?

Smith: Especially anyone who goes into a corporate, M&A space, your first three years, you’re just trying to keep your head above water. You’re drinking from a fire hose. I call it the growing pains stage because you learn by messing up. That’s the biggest thing I share with people. In my experience, lawyers tend to be super high-achieving individuals, very ambitious, and it can be very jarring to be in a situation where you feel like you’re not knocking out of the park every single time. Just explaining it to them that it is a part of the process and as long as you’re bringing a great attitude, you’re doing your job and learning from your mistakes, obviously. I would say mid-level to senior associate that’s when you start asking questions of the people more senior to you. I’m really good about trying to do this, you know, have their goals changed since they started. When you first start, you’re just happy to have a job and you just want to learn. All of the sudden there’s a switch where you actually have control over what you do and the kind of clients you work for, to a certain extent. So, it’s always important to be watching the people around you and pick someone whose career you think you want. Frankly, really try to cherry pick from other people and emulate that in your practice. For me, it’s important to be extremely responsive to clients and I over communicate. One of the things you learn is what kind of substantive work you want to do, but also you need to start paying attention to the business of a law firm.  When you become a partner, it’s not the same as you being an associate and being responsible for the substantive work. You’re literally now responsible for running a business. I think the earlier associates understand what that looks like, one, they become better associates but they also start to understand what it means to be a partner in a law firm. I remember I’ve had partners sit down with me and break down how cash flow works in the law firm — why we do certain things at certain times of the year. You know really start to think like a partner so that other people when you are talking with clients, when you are talking to other partners, you are emulating what you essentially want.

WLJ: You have made multiple recognitions, “40-under-40,” “Ones to Watch.” How do you balance being visibly external with the internal work of deepening your practice and expertise?

Smith: I don’t necessarily advise people to do it the way I did it. We’re just being candid. Especially when you start, specifically in the law firm context, it’s not uncommon for associates to be rather slow the first couple months that they join a law firm. Mostly people are getting used to you being there. You’re, for lack of a better term, disrupting a dynamic that already existed. People have to get used to you being there and being someone they can go to. For me, I am not originally from the state of Wisconsin. I’m from the south suburbs of Chicago, the Chicagoland area. When I decided I was going to stay here after law school, it was really important for one, me wanting to stay in Wisconsin but two, also career-wise, I had to build ties here. I’m smart enough to know that a job isn’t enough to keep anyone anywhere and you really need community around you. I think that’s why I got so involved so fast. I was really trying to build a community around me while I was loving the work I was doing. I knew I needed other things to want me to stay here. I definitely feel like, at times, I took on more than I could chew. Learning the word “no,” was important. What I say is that your first three years you should be focusing on learning how to do your job substantively. There’s something to say about being productive. Not every moment is going to be super busy, so what are you doing in those moments to be productive? It doesn’t necessarily mean you’re a part of a lot of boards, but are you grabbing lunch with old classmates or people in the firm so you can build relationships? Are you writing articles? Are you going to events? That is what you should be doing when you have those lower times. Those things, maintain and building relationships, are so crucial to your job. Those are the times where you look for windows of opportunities to lean in on those things. Like I said, I felt like took on a little more than I could chew right away. I can’t say that I regret it because it has help me become selective in how I spend my time. Also, as I’ve become more senior, I have more responsibilities. I’m the one the client is calling. I’m the one who has to navigate those relationships more directly and so my availability outside the day-to-day is much more limited.

You have to stay connected; you have to stay involved. You have to make sure you’re prioritizing your work. If you have a great reputation for being out community, that is awesome. But what you want that to do is to translate into being a great substantive lawyer. You can build all the relationships you want, but if you can’t deliver, it really doesn’t help you. It’s a constant balance. That’s what I’ve tried to do.