Leveraging Latitude | Inside Contract Engagement Work
Episode 27 | February 11, 2026
Episode 27 | February 11, 2026
Legal careers take many forms—and flexible engagement work is increasingly part of that conversation.
In this episode of Leveraging Latitude, Candice Reed is joined by Amber Hilliard and Cynthia Cutler Moon for a candid conversation about how contract engagement work shows up in practice today. Drawing on their own experience as attorneys who have worked in and alongside these roles, they talk through how flexible engagements fit into today’s legal careers and legal teams.
Together, they explore:
This episode is for attorneys who are curious about contract engagement work, and for legal leaders looking for a clear, experience-based perspective on how flexible legal talent can support today’s legal teams.
Amber Hilliard 00:00
Once you take that first step and you try something, you’re like, “Wow, I just developed this incredible skillset that makes me this much more marketable.” It’s like, where do I go next?
Candice Reed 00:08
There are people with that experience and with that skillset doing work on a contract basis.
Cynthia Cutler Moon 00:13
Sometimes there was a stigma attached to a temporary or a contract role and these can be very sophisticated and very career growing.
Amber Hilliard 00:22
So I’ve found positions where I was able to parachute into complex legal issues, continue to provide sophisticated level of legal support. But then also make it home for dinner and to be able to provide all of the other support that I wanted to provide to those of my family members.
Candice Reed 00:38
This is Leveraging Latitude, Cultivating a Full Life in the Law. Please join us on our journey as we discover how to leverage the hard work of becoming a lawyer, to achieving success, and leading a rich and fulfilling life in the law.
Candice Reed 00:52
Hello. I’d like to welcome everyone to the Leveraging Latitude podcast. I’m Candice Reed, and I’m so excited to have this conversation with you today because joining me are two of my Latitude colleagues. So this is just going to be some coworkers getting together, chatting around the proverbial water cooler and talking about the thing that we most like to talk about, which is our work. So with me is Amber Hilliard. Hi, Amber. It’s great to see you.
Amber Hilliard 01:30
Hello, Candice. How are you?
Candice Reed 01:33
Great. Doing really well. And Amber is the leading partner in our Washington, D.C. market. She is relatively new to Latitude, just having celebrated – or coming up on your one-year anniversary, I believe. Is that right?
Amber Hilliard 01:53
Yeah, that’s right. In April.
Candice Reed 01:54
Thank you so much for joining this conversation. I will allow you to introduce yourself here briefly. I also want to note the other member of our panel or conversation today, Cynthia Cutler Moon. Hi, Cynthia.
Cynthia Cutler Moon 02:11
Hi, Candice.
Candice Reed 02:12
Cynthia and I are both joining the conversation from Nashville, Tennessee, where we are based. As I mentioned, Amber is in D.C. And Cynthia is our Vice President of Legal Recruiting and Placement. So she works with all of our attorneys who both are serving as Latitude attorneys on contract engagements, and then those candidates who are interested in working with Latitude on contract engagements. So welcome to the conversation, Cynthia.
Candice Reed 02:45
Like I said, I’d love for the two of you to give us a fuller picture or description of your prior legal experience because both of you came to Latitude. Cynthia’s been here. You just had your sixth year anniversary, so it’s been quite a bit longer. Both of you came to Latitude after very successful, impressive legal careers, practicing as lawyers, both at law firms, at AmLaw 100 firms, as well as in-house. So Amber, I’d love to hear from you what you have done over the course of your career, your legal career, and what brought you to Latitude.
Amber Hilliard 03:34
Sure. So my legal career started at Skadden Arps where I was in the corporate practice, focusing on M&A, corporate governance, and securities. I spent eight years there supporting lots of companies, publicly traded companies working on sophisticated M&A matters, and then the accompanying corporate governance and securities issues. And after eight years, I went in-house to Fannie Mae where I was on the corporate governance team and led a huge strategic corporate governance project before moving on to stints at several other publicly traded companies where I served in leadership positions and continued to work on corporate governance, M&A, and securities work.
Amber Hilliard 04:17
Those leadership positions took the form of both permanent roles as well as some contract-based work. And that was one of the reasons that made me very excited when I concluded my time most recently at Tupperware Brands Corporation that I found this opportunity to come work for Latitude in the capacity of supporting other attorneys who are seeking out those contract type engagements and looking to just fill out their careers with lots of unique opportunities to parachute in and support some sophisticated clients. So I’m thrilled to be a part of the team and really excited about the work that we do here.
Candice Reed 04:55
That’s great, Amber. As you were talking, I was realizing that we both have that in common, that at some point during our legal career, we were both brought into legal departments in leadership positions on a contract engagement. I know that that is how I actually started my in-house career, if you will, or at least as you said, the stint that I had practicing as in-house counsel for a few years. So we’ll get more into that since that’s the topic of the day. But before we do that, Cynthia, what have you done or what did you do as a practicing attorney and what brought you to Latitude?
Cynthia Cutler Moon 05:52
Like many of us here and many of the people that might be just getting out of law school and not expecting it, your legal career may be long and winding and have some twists and turns you did not expect. And that’s what happened with me. I started at a medium-sized law firm in Lexington, Kentucky, doing litigation and labor and employment work. And then I was recruited by an outside recruiter to come to Nashville and join Baker Donaldson, where I continued an employment law practice. And I was there for many years until I decided I wanted to try something new and Big Law life was not going to be my career forever. And I actually wound up moving into legal recruiting at that point with the same recruiter who had brought me to Nashville. And I did that for a few years before going back to a practice of law.
Cynthia Cutler Moon 06:46
And I wound up as the general counsel of a transportation company here in Nashville. And I did that for several years before I decided to retire early and travel the world as a little nomad with a whole RV lifestyle. And I did that for a couple of years before I reached out to you, Candice, and said, “Do you have an engagement role that I might be able to do for a little bit because I’m going to be in town for a few months?” And that turned into a conversation about, would you be interested in returning to legal recruiting, which I was. And the rest is history.
Candice Reed 07:27
As they say.
Cynthia Cutler Moon 07:28
Yes.
Candice Reed 07:31
Yeah. Cynthia, your story highlights for me what we often say, which is we’d love to talk to attorneys who may or may not be considering a job change, who may or may not know what contract engagements are or what working through Latitude would look like. So much of our work involves having conversations with people at various points in their career and trying to help them either through working through us or by virtue of some of our shared connections and making those introductions that we want to talk to you even if you’re just exploring.
Candice Reed 08:21
Amber, since you first mentioned your stints at various large companies, publicly-traded companies, we will protect their anonymity and just refer to them as that for now. But what attracted you to contract work? We hear this question all the time, but for those who may be wondering, what’s the appeal? Why contract work?
Amber Hilliard 08:52
Sure. So the motivation changed at different points in my life. Initially, I went into contract work because I had an opportunity to delve deeper into securities law, which was an area where I needed to focus more and to continue to sharpen my skills after having left an in-house role. And so for me, it was about the opportunity to really do the deep dive, to develop the skills, flex my skills in a space that would then help to better support future opportunities where I could be a truly well-rounded corporate attorney that had the expertise that I wanted in the security space. Later in my career, the reasons for doing it were much more around personal needs.
Amber Hilliard 09:33
So I am part of what, I guess, has been dubbed the sandwich generation. I have young children, I had aging parents at the time, and the needs and the desire to support them and to be more present and to have more control over my schedule. But also the strong desire to continue working on really sophisticated issues that were consistent with the work that I had previously done and wanting to continue my same career trajectory. So I found positions where I was able to parachute into complex legal issues, continue to provide sophisticated level of legal support, but then also make it home for dinner and to be able to provide all of the other support that I wanted to provide to those of my family members.
Candice Reed 10:18
I think that’s a great point that it’s not… Contract work doesn’t necessarily just exist for attorneys to be able to work around personal challenges or challenging schedules or other personal obligations. The first thing you mentioned was that the contract work initially gave you an opportunity to go deeper into securities law. So to build your skills as a lawyer. I think a lot of people may assume that most people do contract work purely for the personal goals or to assist with personal goals or obligations, and often don’t realize that contract engagements can actually help you develop in your professional career. Cynthia, I see you shaking your head. Do you want to add to that?
Cynthia Cutler Moon 11:18
No, I just want to echo what Amber said, and I think she’s such a prime example of what we see in the roles that we get every day, that some of these can be launching pads for people’s careers. It may be their first way to get their foot in the door to get an in-house role when coming from a firm that they wouldn’t otherwise have that opportunity maybe at their level, or the stars align and it works out. But we work on in our engagement roles, some of these can be career changing and life-changing opportunities for some of our candidates. It’s not a step down or a… Sometimes there was, back in the day, a little bit of a stigma attached to a temporary or a contract role, and we see these to be very sophisticated and very career growing.
Candice Reed 12:10
I think that’s a good point too. I first started in the flexible talent space back in 2005. I’m dating myself. For those of you who have listened to this podcast previously, you may have heard me talk about how my child loves to remind me that I’m old because I was born in the 1900s. So let’s just put that out there. I am of a different century, apparently.
Candice Reed 12:38
Back in 2005, oftentimes I found that when pitching the idea to clients or prospective clients to use flexible talent or contract attorneys, I was often met with that stigma, Cynthia, that, “Oh, but we need someone with 10 years of experience,” or, “We need someone with sophisticated SEC experience,” or, “We need someone with prior in-house experience.” And what was often unsaid was the belief that the only people who were working contract jobs were those who couldn’t find a, quote, unquote, “real job” or who were right out of law school doing document review.
Candice Reed 13:29
And so I was having a number of conversations and providing a number of examples of like, “Hey, actually all that you just described you need, there are people with that experience and with that skillset doing work on a contract basis.” I don’t have those conversations as much anymore. I think that particularly on the in-house side, we have seen almost a universal adoption of flexible talent as part of the in-house toolkit. It is a way that general counsel and managing attorneys on the corporate side are staffing their teams. And I mean, to be fair, at this point, law firms are right behind them as well. So we’re seeing opportunities for more diverse roles and more experienced needs and the attorneys who are filling those positions. Cynthia, I wonder if you can tell us what’s hot right now. What are some of the roles that you are seeing come in that clients are asking for the type of experience they’re looking for? What are we working on right now?
Cynthia Cutler Moon 14:52
Being in the Nashville market, I always get in-house healthcare attorney roles, and that’s just such a great field to be in. It’s not an area that’s ever going to be outsourced, so we love filling those. Another really big area right now that we’re seeing across all of our markets are attorneys with experience in AI, whether that’s helping train language models or beyond AI, technology contracts, technology transactions. But if you’re an attorney and you’re looking for the next new niche, check out AI.
Candice Reed 15:32
Yeah, that’s true. We do see that a lot across our markets generally. Now, Amber, you are in a unique market being in D.C. Are you seeing anything, any trends that may be different from that?
Amber Hilliard 15:47
Yeah, definitely. Well, no, I would say it’s very consistent with respect to the AI being a heavy area of focus. In fact, I was at an event last night speaking with attorneys and AI was… It was all DC attorneys. AI was definitely the topic of the moment. I would add to the list that Cynthia provided, there’s also a desire for attorneys who can provide more of a consultative approach to AI use, whether it be through the governance, or through the tools, or through establishing those necessary guardrails to ensure that AI is being used responsibly, because there’s a real push for it. The discussions last night talked about how both law firms and in-house are really pushing for the use of AI to increase efficiency. But as lawyers, we want to do that in a responsible and ethically responsible way and in a compliant way.
Candice Reed 16:32
Yeah. It’s funny you mentioned your conversation last night because I had a conversation with a client yesterday. So obviously very timely, very relevant. And this was an in-house managing attorney who was saying that the company generally was pushing the use of AI, not just within legal, but across all of its divisions or departments. This client made mention of the need for someone who was tech curious… Or tech interested. I’m sorry, not curious. Her point was, we are looking for attorneys who are willing to engage AI and use it in their legal practice, not necessarily to do anything specific. She didn’t go into specifics anyway, but it was that like, “Hey, you got to know how to use the technology or at least be interested in learning how to use it, be facile with the technology that at least most companies are using now.” And again, I think that law firms are just right behind, if not already there.
Candice Reed 17:43
Amber, you mentioned, you described some of your prior engagements or prior roles as leadership positions. So that caught my attention. So were you brought in even on a contract basis to serve in a leadership role?
Amber Hilliard 18:04
Yes, absolutely. So at least three of my roles were interim VP roles at publicly-traded companies and they often come about because companies are in some sort of transition. One was because a company was in the middle of an M&A transaction and because of their interim operating covenants, they were not permitted to hire. So there was a hiring freeze. And in another example, a company was in financial distress. And for that reason, they also had a hiring freeze, but desperately needed someone to come in and to serve in that capacity, that leadership capacity to manage the team and to support the team through that process. And in the third example, there was a company that had recently completed a large transaction and needed that extra assistance to support and guide the team through the post-merger time until they were more stabilized and the team sort of had their sea legs.
Amber Hilliard 19:00
So yes, that was honestly the most rewarding of all of my opportunities were the ones where I got to come in and lead a team, parachute into a company that was in the middle of a transition and provide that stability to the team and to help support them, train. There was a lot of training opportunity there, lots of opportunities to mentor junior attorneys. And then to also help to establish processes and procedures to right the ship and to create a more sustainable sort of future for those departments.
Candice Reed 19:32
And as you’re saying that, I’m thinking that a lot of the skills that you built in those positions are also what make you successful at Latitude too, building a team, building out processes and procedures for growing a market, that business acumen that not all attorneys, in fact, I would say few attorneys get early in their career, that oftentimes you have to work in-house or work in close collaboration with a client in order to get that business experience and know how. And you never know how or when, where you may use it going forward. One thing you mentioned too is that sometimes it is just a matter of being open to what the client needs and how they may want you or how they may need to bring someone on into a role. So in my personal experience, I mentioned that my first role in-house initially started as a contract engagement, and it was because it was a brand new role.
Candice Reed 20:50
I was essentially coming in to serve in what we now would probably call a legal operations role, where I was managing parts of a legal department, reporting to the general counsel, but that was not a position that was currently in place. It’s not like I was filling a vacancy that was created by someone leaving. That was a new role that the general counsel wanted to build out, but didn’t have the budget approval for it yet. There wasn’t the budget approval for a full-time hire. And so I was initially brought in as a contract attorney to kind of prove out the need, if you will, and also give the company time to fund what ultimately became the FTE or full-time role. So sometimes it’s just a matter of being open.
Candice Reed 21:51
Cynthia, when you’re talking to attorneys who may not be familiar with contract engagements or who may want a more, what we would think of traditional full-time role, they’re not really looking for flexibility. But what can they do or what might they want to think of that would help them take advantage of some of these roles that may start as a contract engagement and then ultimately lead to something more full-time?
Cynthia Cutler Moon 22:30
The conversation that I often will have with candidates is very similar to what we’re talking about here. And I try to be very transparent and explain that when it comes to engagement opportunities, it really runs the gamut of potentially an interim role or even on the higher level, like interim or fractional GC kind of role for a company that’s not quite ready to hire someone full-time, either because they don’t have the budget, they’re not sure about the need, they’re proving out the need like you were just describing, Candice, and sometimes they need someone to start right away.
Candice Reed 23:10
Yes, yes.
Cynthia Cutler Moon 23:11
And their hiring process is a month-long thing. And again, I said it before, like your foot in the door. This can sometimes be your foot in the door to a permanent role, particularly for someone that is looking for a permanent role. We sometimes have opportunities that this is how it’s going to start because this is what the company wants and needs right now.
Candice Reed 23:31
So a couple of things come to my mind because again, a lot of my work is on the client side. So when you have a candidate who’s basically willing to come in and on that contract engagement, basically, “Hey, I’m easy to work with. However you need this role to start, I’m confident that I’m going to show you what I can do. And hey, this is an opportunity for me to see if it’s a good match for me.” You’re being interviewed too, client. And one of the benefits is that you sometimes can get paid more on a contract basis because it’s not that, quote, unquote, “secure position” that maybe somebody might be looking for. That the rate or the compensation that they’re able to get during the contract period might be even higher than what a full-time role might pay.
Amber Hilliard 24:34
That’s certainly been my experience as well. I don’t think that you necessarily have to compromise compensation in taking on these contract engagements. If you have the right skillset and the right opportunities present themselves, you can absolutely have the continuation of your salary trajectory not sacrificing in that space.
Cynthia Cutler Moon 24:53
It’s important to note that engagement attorneys through Latitude get full benefits. We have full benefits available for people that aren’t necessarily looking at this as the next step in their career growth, maybe they are looking at it as a step back in terms of hours or putting some guardrails and boundaries over the time they work because of their personal goals or needs. Or they don’t want every hour of every day to be dedicated to billing hours or their career taking over their life. Maybe they want to write the next great American novel, or they do have responsibilities caring for a family member or whatever the case might be. They might just have other interests outside of work and they want to work a 40-hour or less week. Engagement opportunities is a great way to do that and still make great money.
Candice Reed 25:53
For us at least, at Latitude, the full benefits kick in at 20 hours.
Cynthia Cutler Moon 25:58
They do.
Candice Reed 25:58
So there aren’t many other legal jobs where you can maintain a 20-hour a week schedule and still get full group health insurance, and a 401(k), and dental, vision, all of that stuff. So I do think that so much of our job is educating people on what these roles are and what they provide, not just to the client who may be seeking extra help or wanting to relieve a team that is overburdened or taxed out maybe during a certain phase of their work life. Or maybe, as you said, Amber, they’re going through some sort of event like a merger or an acquisition and the team is pulling 50-, 60-, 70-hour weeks and they need some additional help. It’s not just what the client gets out of the deal. There are a lot of tangible and intangible benefits to the attorneys working in these roles as well.
Candice Reed 27:14
Both of you have mentioned this idea of parachuting in. I often refer to our attorneys as like legal Mary Poppins, right? They just come in, they float in, parachute if you will, into a situation. And because of their experience and because of their skillset, they’re able to help the clients out right away. And so therefore, you’re going to have to pay for that level of expertise and hit the ground running with little handholding, little instruction. Because a lot of times they’re not in those positions for very long, and so they need to make an immediate impact. Now, some of our folks have been in their contract engagements for a very long time. I think one of our attorneys who semi-retired, what? Over 10 years ago, has been in the same contract engagement for, what? A dozen years?
Cynthia Cutler Moon 28:11
12 years.
Candice Reed 28:12
Yeah. So these are not always short-term roles, and they don’t always lead to permanent positions. They can continue to be contract year after year after year, oftentimes at a reduced hour schedule or something like that. Let’s put a little bit of color around our attorneys. And Cynthia, you mentioned writing the great American novel as being one reason you might want to do this. But what are some of the other reasons that you’ve heard or that you know of just looking at our current Latitude attorneys out in the field, so to speak. What are some of the things that they’re doing in addition to practicing law that they’re able to do because of either the flexibility or the boundaries that Latitude affords?
Cynthia Cutler Moon 29:09
A big one, this has always been a big one, but it’s come up, it continues to creep up at various times, and that’s the ability to work remotely. While there are many permanent roles that are remote, there’s also equal numbers of companies that have gone back to everybody comes here, you’re out. And including very large companies and people that have been working there directly have lost their jobs or know they’re going to lose their jobs and they’re reaching out going, “What can I do on a remote basis?” So that is always a huge one. So it’s not so much what else they’re trying to do as they need a role that they don’t want to move or they need to be at home. Childcare obviously can always be an issue as well, not so much childcare, but having younger children where they want to be available to attend events or take kids to school. So they need that flexibility to pop out for 30 minutes in a day. And if you’re working 40 miles away, that’s not something you can handle all the time.
Candice Reed 30:16
Aspiring musicians.
Cynthia Cutler Moon 30:17
Aspiring musicians.
Candice Reed 30:18
Choirs.
Cynthia Cutler Moon 30:18
We do have someone who has written several novels now. A second novel is coming out. We can do a plug for him later. We have a lot of musicians, particularly here in Nashville. And it’s so interesting. And Amber and Candice, I know you’ve looked at resumes as well, and you see sometimes these interests and you’re like, “I need to talk to you about that.” And it gives them time to pursue that.
Candice Reed 30:46
Amber, what were some… Oh, I’m sorry. I’m sorry, Cynthia.
Cynthia Cutler Moon 30:48
No, that’s it.
Candice Reed 30:50
I was just curious, Amber, what were some of the fun things that you were able to do because you had a more predictable schedule when you were working on some of the contract engagements you worked on?
Amber Hilliard 31:05
For me, it’s been the opportunity to get more engaged in the community. So participating in fun community service activities, some of those were ones that occurred during the day because they were very time sensitive. So being able to, for example, go prepare lunches for those in need and being able to do that in the middle of the day, take an hour and a half, pop out, go do that activity and come back. So that was really rewarding. I would say even more exciting, some of the attorneys I’ve worked with, bird watching was one that I found very unique.
Candice Reed 31:37
Really?
Amber Hilliard 31:38
Yes. Yes. I would describe it as perhaps competitive bird watching such that the attorney needed to be in a certain location at a certain time in order to observe certain birds.
Candice Reed 31:50
Oh wow.
Amber Hilliard 31:51
I always loved hearing the stories when she returned from her travels about where her bird watching had taken her.
Candice Reed 31:57
Yeah, that reminds me of our competitive pickleballer. And this was before pickleball was something everyone did. Cynthia, I don’t know if you remember the gentleman I’m referring to.
Cynthia Cutler Moon 32:08
I do.
Candice Reed 32:09
But yeah, he was, or may still be, a competitive pickleball player and wanted to work in a contract capacity partly so that he could travel to all of these various tournaments around the country.
Candice Reed 32:24
And then let’s be real clear, there is also nothing wrong with just not wanting to work 40, 50, 60, or even 30 hours a week, right?
Cynthia Cutler Moon 32:39
And sometimes this flexibility is ideal for somebody as a supplement to their other professional goals. So we do often work a really ideal Latitude engagement attorney sometimes is someone who is a solo practitioner or someone thinking about hanging out their own shingle. This gives them a little bit of a security blanket. Let me make sure I have some income coming in while I am growing my own practice. And so-
Candice Reed 33:05
Or some other business.
Cynthia Cutler Moon 33:06
Or some other business. Exactly.
Candice Reed 33:09
Lawyers often have their fingers in a lot of side hustles, if you will. And building out a business, whether it’s a coaching business, a yoga practice, a new business venture, something even more requiring more time than maybe a few hours a week, that we do see a lot of that supplementing of work. Lawyers are interesting, y’all. Oh my goodness, we’ve all got so many various hobbies and interests, goals, and they’re fluid and dynamic and they change. So early in your career, you may have been thinking, my goal is to make partner and make a million plus a year and then you have a family or maybe you get involved in bird watching or pickleball and all of a sudden you’re like, “Hey, wait a minute, I could probably get by with a little less than that a year and not work as hard.” So that’s one reason why we like to have conversations with folks at various stages or at various times in their career because what you wanted right out of law school may not be what you want 10, 15, 20 years into your law practice.
Amber Hilliard 34:45
Oh, that’s absolutely right, Candice. I would say that that very much tracks with my experience sort of starting off on a very traditional Big Law firm track and then realizing that I wanted more dynamicy from day to day. And also wanted to be available, like I said before, to the people who mattered in my life. And being able to strike that balance and having this flexibility to continue to adjust my career as my needs change, as my goals and objectives change has been a real gift for me. And really grateful that I took the risk of going off of the beaten path a little bit and exploring, developing the skills, being strategic about how I wanted to grow as an attorney and as a person.
Candice Reed 35:26
Oh, I love that. Talk to me a little bit about risk. What was the process that you went through intellectually to decide that you could give this gift to yourself? You could continue to work at a high level by doing something slightly off the beaten path.
Amber Hilliard 35:55
Funny enough, the process that I went through probably is more described as the seven stages of grief in many ways, right? Because I had to grieve my predetermined, prescribed path. I had to be willing to give that up to take on the challenge of doing something new and something that I felt served me better, but it wasn’t a decision that I took lightly. I recognized the impact that it would have reputationally with some of my peers who just didn’t understand or appreciate the incredible and tremendous potential that lied within the contract engagement space. But once I kind of got over myself and got over this prescribed, this is the way your journey has to be, and leaned into what my needs were, and what the needs of those around me were, and what actually was going to benefit me long-term in terms of my career goals. Once I embraced that, that’s when all of the possibilities opened up.
Amber Hilliard 36:56
And once you take that first step and you try something, you’re like, “Wow, I just developed this incredible skillset that makes me this much more marketable.” It’s like, where do I go next? And then for me, being able to parachute into companies that are in the middle of these huge transitions and to make such a high impact and to also pick up skills, gain friends, colleagues, work in spaces, learn industries, all of those things have been tremendously exciting and rewarding and have only just added to my professionalism and added to the skillset that I can bring to my role here at Latitude.
Candice Reed 37:32
Cynthia, I’ve heard you talk about the topic of risk and taking risks in your career before. Is there anything you would add to what Amber said, that this whole idea of letting go of what other people have said you should do or you should be, and actually identifying, recognizing and working towards what you need or what you want. I know you’ve done that throughout your career. What has been your process or how were you able to come to the decision to take the risks that you have in your career journey?
Cynthia Cutler Moon 38:21
I think some of it was letting go of that. Your identity isn’t defined by your job and your career. And although I don’t think I-
Candice Reed 38:35
Or at least your whole identity, right? It could be a piece of it. Yeah.
Cynthia Cutler Moon 38:40
And I think at some point, I don’t think I thought about it this way then, but for me anyway, your career should work to serve you rather than me working to serve my career the whole time. I was giving all of my energy to that and that’s not how I’m built. There are plenty of people built that way. I talk to attorneys all the time that are interested in engagement work because they retired and they’re like, “Yeah, I can’t reorganize my closet again. I got to work. I got to do something.” That’s not me. That’s fine. Good for you. I can help you with that.
Candice Reed 39:13
Though, you did admit earlier that you had already retired and allowed me to convince you to come out of retirement and have been working with Latitude for the last-
Cynthia Cutler Moon 39:22
This isn’t practicing law.
Candice Reed 39:25
You’re not practicing law. That’s true. So there’s a little bit of that there still.
Cynthia Cutler Moon 39:29
Yeah, absolutely. Absolutely. And one of the things I’ve talked about before is the process for me was you put a lot of sweat equity into becoming a lawyer. It’s a big deal. I did identify very much as a lawyer and that was a big part of my identity and it was a big deal for me to walk away from the practice of law. Now, I wound up going back. So never say never. And pivots, remember, long and winding career. You’re not necessarily closing the door forever, but it was a big scary jump for me the first time I walked away from practicing law day to day. And then I found I was a lot happier with what I was doing. And so subsequent changes become much less scary. I think the first jump is the biggest.
Candice Reed 40:28
Yeah, that first jump is the biggest. That was my experience too. I had someone ask me once what thing happened in my career that I felt like was the pivotal moment. And I said that I had an opportunity to take what others might have considered a risky move very early on in my career. I still tortured myself with the thought that it was risky for a while. But I’m so glad I had the opportunity to do that early in my career because then as other opportunities came about at various points over the next 20 years, they didn’t seem nearly as risky. They didn’t seem nearly as big a deal. I was like, “Yeah, there’s a lot of good wrapped up in this opportunity, so I’m going to try that. And if it doesn’t work out, I can always go back to practicing law.”
Candice Reed 41:23
I think that we all probably appreciate, but may not admit to it, that we’re all still lawyers, whether we’re practicing law 60, 70 hours a week or not. You’re still a lawyer if you’re practicing law 10 hours a week, or 20 hours a week, or on a halftime basis, or taking a couple of months off here and there and picking up contract engagements in between seasons or during the school year and taking the summers off, et cetera. No one takes away your lawyer card or cred, really. I have found that most employers are not concerned about the number of hours that you worked in your last job or in your last gig. So it’s just that you’ve had the opportunity to stay fresh and keep abreast of your niche area. That’s what they want to see.
Cynthia Cutler Moon 42:32
And I think we get that question from candidates a lot like, “What would it look like on my resume? Will potential employers in the future look down on this?” And I love that you said that, Candice, because that has not been the experience we’ve found. I was talking about leaving the practice of law together and doing something else. Leaving your direct hire. I’m not even going to say permanent role because nothing’s permanent, as we all know.
Candice Reed 42:54
Right. Right.
Cynthia Cutler Moon 42:56
Your direct hire role where you feel like you’ve got a lot of stability, and some of you do, some of you don’t.
Candice Reed 43:03
Some of you don’t know. You never know what might happen with mergers and all that stuff.
Cynthia Cutler Moon 43:09
Yeah. And I’m not trying to scare anyone. I think people have this thought sometimes about when we’re talking about risk for an attorney thinking about doing an engagement role, there’s one, that they worry about stability and how long-term this potentially could be. And we of course have engagements that are very long-term and we’re very clear on that, what the expectations are upfront. So sometimes it’s about stability, but I think that sometimes can be misleading because a direct hire role may not be as stable as you think either.
Cynthia Cutler Moon 43:45
And the other thing is it’s not a risk of the same level like what you were just talking about as you’re still practicing law and we have not found problems with engagement attorneys going back into direct hire roles and vice versa. It can be very fluid. And as you said right at the beginning, Candice, so many more, particularly corporate legal departments, they get the value of this and they know what their… Supplemental attorneys and their flexible legal talent, they know the sophistication of the work that they’re working on.
Candice Reed 44:21
Yeah, they know what you’re giving them. They know what work they’re being given.
Cynthia Cutler Moon 44:26
Yeah. So this does not have… I think it’s a way to deal with a lot of fears about it.
Candice Reed 44:35
Yeah.
Amber Hilliard 44:35
And I would echo the fluidity there. My opportunities were sort of interspersed with direct hire roles as well, and I did not have any challenges in particular with respect to transitioning in and out when life required that of me. And as far as hiring managers, looking, reviewing, and seeing the type of work that I did, there’s a real respect for being able to parachute into these situations and they recognize the value of someone who can get up to speed very quickly, can pivot and adjust very quickly to different and adapt to different environments. So those are all just tremendous skillsets that lend themselves to marketability in the future.
Candice Reed 45:15
Oh, that’s a great point. That’s a great point.
Cynthia Cutler Moon 45:17
Yes. I wanted to say something to Amber because when you were first describing all those roles and all I kept thinking of is this is the exact example of what I tell potential engagement attorneys. I’m like, one of the best… Yes, we care about your substantive skills. We care about lots of things about why you might be a good fit for this role. But to me, the number one characteristic you need as an engagement, to be a successful engagement attorney is to be flexible and have the ability to be flexible. Not everybody is. We have lots of people that are great attorneys, but they’re not going to work as an engagement attorney because you got to be able to roll with it some. And it was exactly what you were talking about, Amber. That’s in my opinion.
Amber Hilliard 46:03
And I would add that we really focus as we’re recruiting on identifying candidates that have that flexibility. And I think we do a great job of vetting and screening for that through our process because that’s really the secret sauce right there, is bringing in people who have that flexibility and who can parachute in and begin to provide value right away.
Candice Reed 46:23
And it’s a mindset flexibility, not necessarily a flexible schedule. We’re used to working within very strict schedule parameters. It’s the mindset, the kind of go with the flow, take it as it comes, not worry too much about title or the corner office aspects of the practice. But more about like, what does the client need? How are you going to add value right away? What do they need you to do today? Review a contract or negotiate a contract, which is it? A lot of what attorneys are doing day in and day out with clients anyway, because needs change and that type of thing.
Amber Hilliard 47:13
Absolutely. And a lot of these teams are very lean as we’ve described previously, which is why there’s the need to bring in the supplemental support. So screening for those attorneys who know how to be utility players, but can also flex up and be a leader or manage a process or a project is exactly what we specialize in. And I think we do a great job of identifying those types of candidates.
Candice Reed 47:35
I do too, Amber. I think we do a great job of that. So if someone’s listening to this conversation and saying, “Okay, I get it. Now I’m interested. I’m intrigued. I’m intrigued. I don’t know that I want to jump in with both feet yet, but I am intrigued.” Cynthia, what should be or what would be a next step for them to take?
Cynthia Cutler Moon 48:00
If somebody was listening to this podcast and they’re like, “I’d really love to learn more about this.” Go ahead on our website, which is LATITUDELEGAL.COM, look at the available opportunities, see if there’s anything that could be a fit there or that catches your interest and go ahead and apply. Because that’ll get you in our system, and get your resume in our system and one of our recruiters should respond to you or just reach out to one of us on LinkedIn. That’s another, you can always do that.
Candice Reed 48:29
We do strive to have local expertise in markets across the country. So for example, I have lived and worked in Nashville and the surrounding area my entire career. And so I have a really deep understanding of the Nashville legal market. Same with you, Amber, in D.C. and our various partners and colleagues around the country. So yeah, pick the market where you want to go or the person that you went to law school with or the person you share the most LinkedIn connections with and reach out to them and just ask to start a conversation.
Candice Reed 49:17
Okay. Amber, I’m giving you the last word and I’m putting you on the spot. Because you have had experience with multiple roles across multiple platforms or multiple companies that are in this space. What is one thing, I won’t ask for the one thing, but what is one thing that you feel like Latitude does really well or that may set us apart from others in the space?
Amber Hilliard 49:47
Oh, that’s too easy, Candice.
Candice Reed 49:52
Is it?
Amber Hilliard 49:52
It stands out. Latitude stands out heads and shoulders above others in the space because of the deep experience of all of the staff. We’re all deeply experienced attorneys and it’s everything we do is peer to peer and that is instantly refreshing to clients that are vetting us. It’s refreshing to candidates. They’re not spending time speaking with someone who doesn’t speak their language or understand the industry. We’re able to provide more of a consultative approach. Nobody here is ticking in time through lists or meeting quotas or anything like that. We’re just here to have conversations and support our peers, support our colleagues, support our industry, and we just get it. I don’t know that that’s necessarily the case that I’ve experienced in other places.
Candice Reed 50:42
I love that answer because we’ve been very intentional about that with our growth. And I mean, in starting the company, that was something that we said meant something to us. We thought it would mean something to both our clients and the attorneys choosing to work with us. And so nearly 13 years in now, we have kept to that in terms of building out a team of former practicing attorneys. So of course, I’d love to hear that that actually resonates and does set us apart because I do think it is something that certainly makes us different. And I’m glad that there’s an impact, the positive impact we thought that it would have. I’m glad to see that that’s coming out in the candidate experience as well.
Amber Hilliard 51:35
Yeah, absolutely. In the days of LinkedIn, it’s not uncommon for someone to have contacted me and said, “Hey, I took a look at your profile. Would love to work with you.” There’s just that instant recognition that we’re all in the same playing field and it just makes for a very unique and rewarding experience all the way around.
Candice Reed 51:53
Oh, that’s wonderful. Well, thank you both so much for sharing your expertise and your perspective built from your own experiences. It is a pleasure to work with both of you and the rest of our colleagues on a daily basis. And I’m just so proud of the work that we do here at Latitude and the work that our attorneys provide to our clients across the country. And I feel like it’s a special place. So thank you both for being a part of that and for being a part of this conversation. Thank you both again and until next time. Thanks.
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