Communicating Effect ...

Communicating Effectively With In-House Counsel | Karen Delaney

June 23, 2022 | by D. Todd Smith

Many attorneys start their careers in a law firm setting. Often, those roles require working with in-house counsel to provide legal services to a company. How can attorneys transition from a client service role into working directly for the client? Join Todd Smith and Jody Sanders as they visit with Karen Delaney of Delaney Legal PLLC about her experience going from law firm to in-house to solo practice. Karen provides advice for attorneys who are looking to change their practice or role and how to navigate different paths. She also offers tips for attorneys in any legal job to communicate effectively with in-house and non-legal decision makers to help them reach their business and organizational goals. Finally, she discusses the pros and cons of setting up a virtual legal practice.

Listen to the podcast here:

Communicating Effectively With In-House Counsel | Karen Delaney

Welcome back to the show. Our guest is Karen Delaney of Delaney Legal PLLC. Karen, thanks for joining us on the show.

Thanks for having me. I’m so thrilled to be here.

If you would tell our audience a little bit about who you are, your background and maybe your path into the law.

I grew up in the Dallas area. I went to the University of Texas for undergrad and then Washington University in St. Louis for law school. Although I wish I had an inspirational story about why I ended up as a lawyer, I was a pretty typical upper-middle-class kid who first thought I wanted to be a doctor, and then got to organic chemistry and realized, “This is not for me.” I tried to think about what I would be good at and landed on law school and legal practice because I had always been a very strong writer. My extremely limited understanding of the law led me to conclude that if I were a good writer, I probably would be a decent lawyer, so here we are.

After law school, did you start going to a firm?

I did. I went to Gardere Wynne Sewell, which is now Foley Gardere. I did general business litigation there for about five years, then went in-house to be a corporate generalist at GameStop where I was part of a small team handling all of the company’s legal needs. In 2017, I moved over to Half Price Books, which most of your Texas audience will probably be familiar with, but it’s a national retailer that sells new and used books. I thought it might give me some more exposure to corporate governance because it was just me and the GC there, but after I had been there for a couple of months the GC left and I took over the legal department. I left Half Price Books at the end of May 2020 and spent some time at home with the kids, and then dove into solo practice.

I want to cover more ground than what you traced there. What made you decide to go into solo practice having had all that experience as an in-house lawyer?

The thought had crossed my mind about jumping into solo work occasionally over the years. I would always dismiss it because there were a couple of mental hurdles that I couldn’t get past. Number one, how would I apply my skill set and leverage my existing network to be successful? As a corporate generalist I was always hiring experts, so I struggled to think, “Could I be an external GC?” My network falls into three buckets. It’s other lawyers that I’ve worked with, whether at Gardere or outside counsel, other in-house lawyers, and then the business folks that I’ve worked with over the years.

My speculation, right or wrong, is that to develop an external GC practice, you probably are working with companies that don’t have a dedicated legal function yet. That’s not where my network lies. I couldn’t be clear on how do I apply this in a way that would allow me to be successful. This was pre-pandemic and a lot of us were still wed to the idea of commuting into an office every day. As somebody who was in-house and didn’t have a book of business to take somewhere, that seemed risky to have significant potential overhead and no clients. So how do you make that work?

Taking some time off cleared some space for me to think about how I would apply both my skill set and leverage my network, and also how I wanted my practice to fit into my life, instead of my life fitting into the space leftover by my practice. I also knew that my in-house friends were getting crushed because legal demands exploded as a result of the pandemic. Frequently, staffing and in-house departments haven’t kept up with those demands.

What I focus my practice on now is negotiating and redlining contracts for corporate clients. My clients all have legal departments. I work with one startup, but by and large my clients are large established companies who need help making sure that contracts keep going. For me, as a corporate generalist, that was frequently a pain point where I was responsible for many legal needs. There are emergencies and fires that pop up every day that have to be put out. How do you keep those contracts flowing smoothly and quickly so that your business partners can get done what they needed to get done?

Even when I was at Half Price Books and we had decided that I needed to offload some of this work so that I could focus my attention on other priorities, I reached out to other in-house counsel at other companies. I said, “Who do you have to do this work for you?” Very often, the answer was, “I haven’t been able to find somebody. Let me know when you do.” Knowing post-COVID that people were much more comfortable with somebody who might not have an office, it’s not necessarily reflective of the quality of legal services that you are going to receive because we’ve all been working from home for the past couple of years. I lowered those hurdles. I found my niche and made the jump.

It seems like so often, lawyers in your position try to become a fractional general counsel and maintain that generalist approach and do what you said. You were going and being an outside general counsel for a company. You mentioned finding your niche, and that was what was coming to my mind as you were talking. That’s quite an interesting niche that you’re filling in from negotiating contracts on behalf of other companies. It sounds like there was a real need there, so congratulations on finding your place relatively quickly in your solo practice.

I appreciate that. It is something that a lot of companies struggle with. It’s a need, and especially being able to lower the overhead and make yourself competitive, there’s an opening there.

I’m curious about your journey because this seems like an interesting place to end up having started at a big firm as a business litigator. How did you initially make your transition from firm to in-house?

I was a fifth-year associate. I loved the team that I was working with and the work that I was doing, but I got a call out of the blue from a recruiter who cold-called me and said, “GameStop is looking to hire somebody. Would you be interested?” I had no idea that GameStop was even located in the area. I said, “Do you mean the place in the mall?” I also had no idea how big they were at that time. They had about 6,500 stores worldwide in 21 countries, 48,000 employees, and about $10 billion or $11 billion in revenue.

I had been thinking that I like my work and I love my team, but partnership is looming. Partnerships seem like you get a lot more pie for having won the pie-eating contest. I was like, “Do I really want to be a partner?” Initially, I thought, “I don’t know about going in-house and I don’t know about GameStop, but I haven’t interviewed anywhere in six years since two LOCI. I might as well kick the tires, shake the dust off, and go interview.”

As I interviewed and learned more about the position and the company, it sounded like an exciting opportunity, especially because most companies of that size have extremely siloed legal departments where you might have somebody who is the senior counsel for European data privacy, but the way that GameStop was organized at that time was they had a very small legal department. Everybody was a corporate generalist. Everybody was expected to be able to figure out how to handle any legal issue that came in the door.

letter blocks spelling out COVID19
Effective Communication: Post-COVID, people are much more comfortable with somebody who might not have an office. It’s not reflective of the quality of services that you are going to get. Just find your niche and make the jump.

It’s an exciting space to be in because one of the reasons that I got into litigation is I’ve always been a lifelong learner. I’m a nerd. I like learning about things that I have no business knowing about. To get to be in a space in-house where you have the opportunity to work on so many new and interesting things and also respond to new developments in the law is a cool place to be, and a unique opportunity for a company of that size.

There’s a little bit of a misimpression that firm lawyers have of in-house jobs. For them, it is this cushy, 9:00 AM to 5:00 PM, no billable hours type of thing, but the reality is there are fires that pop up all the time in areas that you may not know anything about.

That’s right. It also matters where you are in the hierarchy of the department. It may be that when you first come in as a counsel and you’re relatively a junior lawyer, your responsibilities may be fairly defined. There are people above you on the hierarchy who are going to be the ones handling fires because they’re the ones that have the credibility, the authority, and the pay grade to be dealing with those.

As you gain more experience, more trust and credibility with your clients, the likelihood that you are going to be on the frontline for dealing with those issues increases. It also depends on the practice. As a corporate generalist, you are going to be the line of defense for any legal issue that comes up for the company, but depending on your practice, if you’re in a more siloed area, that may not be the case.

I heard you refer to clients. I’ve heard a lot of current and former in-house lawyers use that same terminology. Even though we think, “You’re going in-house. You’re going to have the supposedly cush job,” at the end of the day, you still have a client relationship. Your client happens to be your employer. Would you say that your client most often was the business people or the directors in the organization? Who did you consider to be your client in your in-house jobs?

Let’s separate out who’s my client from an ethical perspective versus who’s my client from a service perspective. My client is the organization from an ethical perspective. As a corporate generalist, anybody in-house is probably going to have a multitude of internal clients because, at the end of the day, you are a service provider to the business and the various people who make the business work.

In a firm, you’re the revenue center and you control it that way. In an in-house, maybe cost center is not the right word, but you’re not bringing the revenue like some of the business people and the salespeople are. Does that change the way that you approach legal problems?

I would describe it as a cost center. At most companies, it’s probably a cost center. That does necessarily shift how you look at problems. It requires a very problem-solving, pragmatic orientation because there are a lot of people internally at companies who may have had an experience with some lawyer in their life in some capacity, whether it’s their internal legal department or it’s some other legal issue they’ve dealt with where they don’t necessarily have the highest regard for your ability as a lawyer to solve problems. They may regard you as the department of no.

This didn’t happen at GameStop or Half Price Books, but I have heard other people refer to their legal departments as the department where good ideas go to die. That crushes me as an in-house lawyer because that is never how I would ever want internal clients to think about what I can provide to the organization. You have to be a problem-solver. You have to have an appetite for risk too.

Most businesses have a healthy appetite for risk whereas external counsel often may not, or there may be a misalignment on what the appropriate amount of risk is and how you tailor your advice to the amount of risk that the organization is willing to undertake. That dovetails with being a pragmatist because there are very few things as an in-house lawyer that you have to say flat out, “No. We are at the end of the discussion. We’re done.” There’s usually a way to accomplish what the business needs to get done. It may just need some tinkering or a more creative mindset to get it solved. You really have to be a problem-solver.

There’s our parallel between in-house and appellate lawyers right there. Anyone reading this is thinking, “They’re talking about all this in-house stuff. What does it have to do with Texas appellate law?” I see the parallel now because so much of what we do is problem-solving. We’re usually trying to fix a problem. Ideally, it could be before the fact, but often it’s after the fact. Being the problem-solver in-house, referring back to your clever play on words with the department of no, I would assume that your preference would have been to have the opportunity to say yes or no rather than trying to fix it after the fact and clean up a mess.

The best outside counsel that I worked with during my in-house career were the ones that want to be right there with you, rowing the boat in the same direction, and helping you solve those problems. There’s nothing more frustrating than being on a call with an outside lawyer and hearing all the reasons we can’t do something without any suggestions for how we could move forward.

That is an area we wanted to cover. It was working with outside counsel and, in particular, outside counsel in litigation. I feel like as outside counsel, a lot of times, you get a piece of litigation or get dropped into litigation and you’re thinking, “Solve this problem.It does take a mindset shift to step back and think about it in the way that you’re thinking about it on the client side of, “Here’s the problem that we need to solve. Help me find solutions,” as opposed to with the lawsuit.

How do you find solutions? What is the overall organizational mindset related to litigation? There are clients who will spend every penny to scorch the earth. I was never one of them. I always believed in resolving litigation as quickly and efficiently as possible. There are a lot of outside counsels who are accustomed to the process of litigation. We’re going to go through discovery. This will take 18 to 24 months. Maybe something will go up on appeal depending on what the issue is. We’re going to march through that process without examining early on whether we should and what are the risks associated with that. Is there a way to get creative about resolving this? How can we create leverage to improve our posture to resolve this? That’s whether it is pursuing something to arbitration or to trial, or resolving it informally through settlement.

What do you see in the ways that outside counsel communicates with you that you think they either do well or maybe don’t do well, or you wish they knew that would make your life easier?

You hit on number one which is, “Please make my life easier.” It’s the thing that every client wants. That’s especially what in-house counsel wants from their outside counsel. Communication is also paramount. What a lot of lawyers could focus on is communication for non-legal audiences. It’s because the baseline expectation, especially for hiring an appellate lawyer and appellate specialist, is that I already expect that you’re going to be an excellent writer and an excellent communicator for sophisticated consumers of legal services, for example, the judges on an appellate panel or me because we have a common legal background. We speak a common legal language.

That doesn’t always translate over to clients in explaining concepts, risks and why we should pursue particular paths to clients, and then translating that into plain language. When you think about making things easier for in-house counsel, to put things in perspective, let’s say the brief that you’re working on is Earth. Zoom out and you’ll see our solar system. Zoom out from that, you’ll see where our solar system lives in our nice little arm of the Milky Way. Zoom out to the Milky Way, and then zoom out to the galaxies that are around us. That might be my area of responsibility as in-house counsel, and we’re talking about Earth.

To the extent that we can reduce the amount of time that I have to spend dealing with this one particular issue, I can focus on all the other things that are pressing and urgent in my various constellations of responsibility. Maybe the business people that I am reporting to have the whole universe, potentially. Even though this issue is very important to us and we spend a lot of time, blood, sweat and tears on it, there’s so much else going on.

two people talking
Effective Communication: The best outside counsel that you can work with are the ones that want to be right there with you rowing the boat in the same direction. The ones that actually help you solve these problems.

I’ll give an example. I had an outside counsel that I was working with on a complex legal issue that had the attention of the client’s executives. I had asked this outside counsel, “Can you put together something quick that I can forward that will explain the basis for that recommendation?” I got back an email. It probably was about two and a half pages long. I didn’t even have to finish reading it to know I can’t forward this to the executives because they are not going to read it and they’re going to be frustrated with me that I would send them such a thing. I said, “Can we chop this down a little bit? Let’s try and get this a little shorter.” What I got back was probably two pages. It was still too long.

At that point, I gave up and I managed to chop it down myself to a couple of high-level sentences and maybe a paragraph, and then send it off to the executives. That’s a frustrating experience because although that was an urgent issue that had the attention of several of our executives, there are so many other issues that are also urgent that also have their attention. You can easily translate plain language, drop the jargon, and be a compact communicator. Any appellate specialist will appreciate how difficult it is and how much time and energy can go into being concise about how you communicate. That’s such a boon to in-house counsel. It’s so enjoyable to work with people who understand how to do that. It makes the practice a lot more fun.

As an outside lawyer working with in-house counsel, one thing that I had to learn over the years was that corporate objectives are not necessarily the same as your preferred course of action as a litigator. You have to keep in mind those business purposes. It ties into what you’re saying about the importance of communication. If that communication breaks down and you go very far afield as opposed to focusing on meeting the client’s objective, that can be a problem later on, especially if you’re talking about time spent that wasn’t what the client wanted to pursue.

Even if it were a sound litigation strategy, there’s a balancing act that comes in between doing what you need to do as the lawyer versus doing what needs to be done to meet the client’s objective. A lot of especially younger lawyers haven’t had the opportunity to learn about that balancing act yet. It’s a great point about making your life easier through communication. It seems like you can’t over-communicate, especially early on in the relationship and working with an in-house lawyer. Would you agree with that?

Yeah. That goes back to what you alluded to as well with the budgets. I drop all of that into effective communication but also developing a relationship of trust, which is also incredibly important. On that budgeting side, you’re right, it’s over-communicating in terms of where we see things going, particularly if the client has asked for a budget. I know I have been in a number of situations where it feels like outside counsel views the budget as a hurdle that has to be cleared in order to get hired, and then it goes into a drawer and nobody ever looks at it again.

One of the worst experiences as an in-house lawyer is getting a bill, opening that envelope and thinking you’re getting a $5,000 bill and, instead, it’s a $30,000 bill, or you thought you were going to get a $100,000 bill and, instead, it’s a $200,000 bill, and feeling blindsided by that. To the extent that, number one, we can over-communicate so that I can trust that outside counsel is aligned not only with achieving the litigation objectives that we have discussed, but also being somebody who is also a keeper of the purse and sensitive to the spend, and whether it makes sense to continue to spend that way and to keep thinking about that. I always appreciate that partnership with outside counsel.

I imagine that, a lot of times, the objectives in the litigation change over time, whether it’s because something has changed internally or maybe your goals have realigned. Maybe other developments have come up or something changes in litigation that may change the strategy as well.

It might. In-house, I always tried to do a deep evaluation very early on of the case to understand what we know and how we would evaluate the claims. Nobody has a crystal ball, but how we do ballpark our likelihood of success based on what we know and what don’t we know, and how that would impact our analysis. My experience generally has been that the longer litigation drags on, the outcome doesn’t necessarily improve that much. It’s how much everybody is invested in getting there and whether you’ve entrenched somebody.

If you’re thinking about being a corporate defendant who is responding to a plaintiff, how much that plaintiff’s attorney has now invested into the case in terms of their time as they have entrenched themselves? Yes, you have to be responsive to things that happen in the litigation. There’s so much that’s outside of your control because you’re dealing with the court, the opposing parties, and the witnesses. Ideally, you would have a fairly good idea from the outset benchmarking your risk and whether pursuing this litigation is going to make it worth it, and at what point you’re going to pull the ripcord if you need to walk away.

I think about communications that I’ve seen where the lawyers on the outside worry too much about the CYA approach. They give you every possibility and every risk, every time, and missed the bottom line a lot of times because they want to make sure you can’t later say, “You didn’t tell me that.It obscures maybe the more important points.

Also, it’s alienating because clients know what you’re doing. We know what you’re doing. If an outside counsel feels the need to document, by all means, you have to do what you feel like you need to do. That always places your in-house counterpart back on their feet a little bit because it feels so adversarial and it’s not a partnership mindset of, “Maybe these are the problems. What is the path forward?” Especially where that’s not necessarily clear.

What about attorneys who are maybe in a few years of practice like you? They think they might want to transition from a firm or whatever they’re doing to an in-house role. Do you have any tips or thoughts on that process for them?

If you’re not familiar with how in-house legal departments work or what needs might be out there, hop on Indeed or GoInHouse.com and start looking at what opportunities are out there and evaluating how your skill set matches those opportunities. There are areas of the law that seem to be very highly in demand for companies. Employment law is one of them. I find that litigation, oftentimes, if you’re not at a mega-company, maybe it is not. How do you fit into that? If you are determined to try and make the leap in-house, do you need to think about pivoting your practice? How would you make that work?

Always tailor your resume to the job that you’re going to apply for. Never send a generic resume. I’ve seen that. If you get to the interview stage, do research. I interviewed a lot of people when I was at GameStop, and very few knew much about GameStop before they sat down with us. It’s delightful when you meet somebody who has put some time and effort into researching the company and is conversant about things that might be in the news related to the company, and who maybe dug into the website.

If it’s a public company, it’s delightful when you meet somebody who looked at the annual report that’s filed with the SEC. That’s a great place to start. Work your network. Your mileage may vary. Know the people that you’re working with, but if you are at a law firm, ideally, you would hope that they would want to help you transition into in-house practice because you are a future client of the firm. I realize that’s not the case for everybody, but consider who can help you with that.

It’s a touchy subject, too, but from a financial preparedness perspective, depending on what kind of firm you are at, if you are at a big law firm, there’s a chance that you might be taking a pay cut in order to come in-house. Are you able to make that work? If not, is there a way to prepare yourself to try and make that work? It’s the golden handcuffs problem.

As far as learning on the job, I know you did big business litigation and then went in and became a corporate generalist. How were you able to develop those skills on the fly?

You rely a lot on your outside counsel to learn and to teach you. You rely on your counterparts in the legal department to help you figure out what the company’s culture is and how to navigate that culture because every company is so different in terms of how people like to communicate, how forward the company culture is, and how open people are to discussing ideas. There are some cultures where people are afraid to dissent or to share ideas, and there are others where confrontation is expected. How do you swim and navigate through all of that? You have to rely on your peers a lot to learn that.

three people having a discussion around a table
Effective Communication: When working in-house, do a deep evaluation very early on of the case to understand what you know. Nobody has a crystal ball. That’s why you have to ballpark your likelihood of success based on what you know.

This may go back to if you’re thinking about going in-house in an area maybe as a corporate generalist and not necessarily as a specialist. How comfortable are you with navigating ambiguity? In-house, there’s so much of it. That may be ambiguity because the path forward is not clear. It may be ambiguity because there are multiple acceptable paths forward.

There are some people that are not that comfortable with making a decision that’s not clear that it’s the best path forward, and that’s okay. That’s something to know about yourself. Other people develop more comfort with it over time as you get that practice and you realize that the world is not going to collapse down around you.

When you went from Gardere to in-house, did you find that suddenly you had a lot of people inviting you to lunch and interested in developing a relationship with you that maybe they hadn’t done before?

It’s funny, Todd, my social calendar seems a little emptier since I went so low.

I was trying to be mindful. I don’t want to overburden anyone with lunch invitations, but especially maybe among the younger lawyers, it’s like, “Karen went in-house. I need a business development lunch.”

That’s fine. I’m a pretty social person. I like getting together with most people regardless of the reason. I enjoy making those connections and keeping those connections, but there is a way to do it that fosters authentic connection instead of looking like a shark and probably builds on a pre-existing connection. If you ignored me every day at the law firm and then send me an invitation to go out to lunch, that doesn’t sound like a lot of fun.

I’m super involved in the local bar and the state bar. I always heard from in-house lawyers that one of the reasons they don’t like to go to bar events is because they can get cornered. Let’s use GameStop as an example. They’re like, “You work for GameStop,” and then you can’t get away because they’re wanting to establish that connection with you in a five-minute period of time that they have at some bar event. That’s why I asked that question. It goes back to a theme that we talk about a lot on our show, which is authenticity and treating people the way you want to be treated. If someone didn’t show interest in getting to know a lawyer before they went in-house, your healthy little dose of skepticism is probably in order.

You talked about why you made your choice to go solo and your transition from that. One of the things that’s interesting is the idea of a virtual practice, which I frankly don’t know before a couple of years ago I had heard much about it, but now it seems like that’s a lot more common. How did you decide or how did you go about setting up that world instead of a brick and mortar setup?

I knew that to target the kind of work that I want to do with the clients I want to have, I have to manage my overhead extremely carefully. I don’t care to have a lease. We’re recording from my office, which is a guest bedroom in our house. I knew I wanted to work out of my house since COVID opened that as a possibility. I didn’t want to maintain paper files. Part of that is not having to deal with the administrative side of that because I don’t have an assistant. It is just me. Any time I spend on non-billable things is time that takes away from billing.

I operate very much from a “keep it simple, stupid” perspective where I am trying to keep everything as simple as I possibly can to reduce my own overhead and to reduce my own administrative time. I also didn’t want to collect a bunch of files that I’m going to have to cart around with me every time we move. I thought it would be easier to maintain things digitally even though I’m a packrat. I keep a lot of things. This is a little bit of a change for me, but it has been nice. It has opened up a lot of possibilities for maintaining and managing a practice that maybe wasn’t open to people a couple of years ago. I don’t know because I wasn’t trying to practice as a solo a couple of years ago.

As a legal technology dork and a former solo practitioner myself, I want to ask you about your tech stack. What kind of stuff are you using to help maintain that “keep it simple, stupid” approach? How are you keeping your files? What technology are you using, if any, that’s notable?

Maybe it’s not notable. For my practice, I need a couple of things. I need a computer that works, word processing software, subscriptions to Westlaw for research purposes and forms, practice management software and Adobe. That’s it. I invested heavily in my laptop. I have a nice Mac Power Book that was very expensive. I’ve always been an Apple user.

From the “keep it simple, stupid” perspective, I wanted something that I perceive to be easy and would reduce friction in my practice in getting sidelined by technology issues that I might not be equipped to resolve. I don’t need much. That was one of the things that was surprising to me because it’s pretty overwhelming when you do decide to go solo to try and figure out what is it that I need, especially if you’re trying to be cognizant of your costs.

As you’re building a business, try not to let those costs overwhelm you. I made the decision to invest there. Otherwise, I have kept it pretty minimal. I’m working on a website, but I haven’t found a need for one yet because in thinking about where my business comes from, it’s all word of mouth. It is all referrals. I’m not necessarily targeting an individual who is Googling divorce attorney or best trust and estate lawyer in Dallas. That’s not necessarily my target audience. My website is in the works, but it’s not necessary. I don’t do any advertising at this point. I don’t invest in any advertising for that same reason. To answer your question, the tech stack is the Mac I use. I store things in the Cloud and I use Cloud software. Probably, the cornerstone is Microsoft Word and my practice management software.

I love that lean approach. Certainly, in today’s world, you can do that in a way that wasn’t possible many years ago. You have the added benefit, as you pointed out, COVID made it acceptable to run a practice from anywhere. Solo practice is a great thing to do. I don’t discourage anyone from doing it. I had a good experience doing it myself. I always thought that what made it workable was the technology available even when I did it going back many years ago. It seems to have gotten better.

Between the combination of whether it’s a Mac or whatever system you use and the ability to work from home and not be shunned because of that. A lot of people think you’re not a real lawyer if you’re going to work from home. In a litigation practice, it might be tougher to some degree, but it’s still doable. It certainly was doable from an appellate practice side. Doing what you do and generally, your clients being in-house lawyers and companies, it’s great what you’ve been able to put together. It’s good to hear about it.

There is so much technology out there. I have tried to keep it simple for myself. Part of that also is an appetite for diving into those things and learning the expenses. There are so many cool gadgets and apps out there that can be powerful for your practice. If anybody is curious either about maybe going solo or even if you’re not solo and thinking, “How might I improve my technology? How might I go virtual?” one resource that I found invaluable is called Lawyer on the Beach. It’s a private Facebook group. Todd, you smiled. Are you in that?

No, but I have this image of a beach lounge chair and some lawyer on their laptop. It’s such a calming, peaceful image to me. A lawyer on the beach practicing anywhere.

group of five people sitting at a table looking at a computer
Effective Communication: Going virtual can help manage your overhead really efficiently. Just keep everything as simple as you can. Use the “keep it simple, stupid” approach to reduce your own overhead and administrative time.

It’s a fantastic group. It’s oriented towards practitioners who either are fully virtual or who aspire to move to a fully virtual practice. Whether you are a family law practitioner or you do trust and estates, or you’re a lawyer like me supporting corporations, it’s where I learned so much about what I need to start a solo practice. Where do I go to get a logo? What do I need for my website? Where can I go to get that done? What are my best options for practice management software out there? There’s so much practice management software. Let me stand on the shoulders of the people who have come before me to learn about those things and to take advantage of those resources. I do highly recommend that if anybody wants to learn more.

I’ll add a couple of resources to that from my own knowledge. One is MyShingle.com, which was created by Carolyn Elefant, who has been an unapologetic solo for most of her career. She’s been writing about this. She has written a book and she has a ton of resources along the lines of what you’re describing. Along the way, I managed to make friends with a lawyer in New Orleans named Ernie Svenson. He’s known as Ernie the Attorney. He has coached a lot of solo lawyers. He was a big firm lawyer who decided he wanted to teach lawyers how to use technology efficiently for the benefit of mostly solo practices. I’ll throw those out there as other resources to check out for anybody who wants to pursue the idea of opening a solo practice.

There are so many resources and I’m always very pleasantly surprised at how complete strangers are willing to share their time and help you.

What are you seeing as the pros and cons of solo practice in your experience so far?

I love it so far.

Tell us again how long you’ve been doing it.

I committed to it in about September of 2021. I left Half Price Books in May of 2020. At that point, when the pandemic started, I had an eighteen-month-old and a three-and-a-half-year-old. Now our five-year-old is about to start kindergarten in the fall and my youngest is about to be four. We kept them home for a year. Once they went back to school, I started interviewing for other in-house positions. I couldn’t get the idea of trying to start a solo practice out of my head. I was like, “If there’s going to be a time to take this risk, then now is the time because once I get another in-house job, I’m not quitting it to start a solo practice. I know myself well enough that I don’t want to do that. This seems like the time.”

I was in the middle of interviewing for two jobs with organizations here in Dallas for in-house positions. I’ll never forget it. I went to lunch with a friend of mine who knew that I was agonizing over this decision. I was telling her about these interviews. I’ll leave out the expletives, but I’ll never forget that she looked at me and said, “What are you doing? I don’t understand. You have a great idea. You are going to be successful if you let yourself be successful. What are you doing talking about interviewing with these other organizations?” I thought, “You’re right.” I needed to hear it from another attorney. My husband has always been incredibly supportive, but it was good to hear it from a friend of mine and decided to make that jump.

The way this is tied to the pros and cons is I had a very solid idea of what I want to get out of this practice from a life perspective. No surprise, with two young kids, I want flexibility and I want the ability to do things with my kids, whether that’s volunteering with a PTA or going to a school play or taking somebody to swim lessons, and to increase my flexibility to do that. That is an obvious pro. My boss is fantastic. We love her. The flexibility has been great. My clients are wonderful. I love working with them. It has been a lot of fun. I’m doing interesting things because I’m going back to being in good company with fellow nerds. I love learning about other people’s businesses and being able to help them.

The con side is as a corporate generalist who spent about ten years plugged into a company, it’s strange to be on the outside and only be getting little morsels and not always having a clear idea of what the priorities are and how this fits into the overall picture. It can be resolved by asking a lot of questions, but there’s an information deficit there that I am not accustomed to having been on the in-house side for so long. The uncertainty of your paycheck. I’m settling into now that I have enough months under my belt to realize anytime that I’m worried that I don’t know what I’m going to do, there’s going to be something in my inbox waiting for me.

People keep coming back and asking me to keep working with them. That’s thrilling, but in the back of my mind, I’m always thinking, “What if this house of cards collapses?” Somebody pointed out to me, “You’re a ruminator by nature? You’re a bit of a worrier. If you weren’t worried about this, wouldn’t you be worried about something else?” That’s true. If I weren’t worried about that, I would be worried about something else.

There’s definitely that financial risk. I have to acknowledge that I’m very lucky in that my husband has a great full-time job with health benefits. Shout out to Southwest Airlines, we love them. I have a supportive spouse who when we sat down and tried to figure out, “Let’s set X as the revenue goal and give it a year and see how it goes,” I had the space and time and opportunity to flesh that out.

One other thing you often hear about in terms of a con to solo practice, especially a virtual practice, is isolation. How are you engaging with other people besides Jody and me on Zoom? Everybody is sick of Zoom. What are you doing to put yourself out in the world to try and maintain that sense of human contact?

It’s hard, especially after a couple of years where a lot of people have been isolated. Particularly with my clients, we don’t do a lot of Zooms, phone calls or Teams meetings. A lot of it is via email, so it’s a challenge to develop and maintain those relationships on the personal side. That is where it becomes especially important to let your work speak for itself because your work has to help develop that relationship.

In terms of outside of this lovely Zoom call, which I’ve thoroughly enjoyed, I try to be pretty conscious about reaching out to people that I haven’t talked to in a while or I haven’t seen in a while and say, “Let’s get something on the calendar for lunch or drinks, or if you feel more comfortable with Zoom, we can do more Zoom.” I try to do something at least once a week where I get out of the house and reconnect with somebody. Especially if somebody has taken a step back from those interactions because of the pandemic, it has been nice to get back together and see people in person. I do think you have to be conscious about that. Jody, you know I’m pretty active on Twitter.

You are and you’re great.

Thank you. I engage with people that way and have developed a lot of personal connections through Twitter as well. There are a lot of different ways to do it. You all probably discussed this before. A lot of it depends on what you feel most comfortable with and what you’re most likely to be successful with. I am unlikely to reach out to somebody I don’t know and say, “Let’s go to lunch,” because I usually find that excruciatingly awkward. I’ve been practicing for several years now and I have a lot of people that I like and I want to catch up with. I rarely go with the intention of trying to extract business from them. It’s more, “I want to know what’s going on with you and catch up.” I also like to eat. I like good food, so I’m easily lured out of the house with the promise of good food.

Do you participate in in-house Twitter? I assume there is a thing.

woman standing by desk looking at paperwork on a phone call
Effective Communication: The biggest pro of doing a solo practice is the amount of flexibility you get. The con is the uncertainty of your paycheck and not having a clear idea of your overall picture.

Yes.

Do you do it now? Are you using that as part of your business development strategy?

No. My Twitter account at this point has always been more personally oriented rather than practice-oriented. I’m not anonymous by any means, but my name is not on the account usually because when I first started using Twitter, I was doing a lot of screaming into the void and didn’t feel like prospective employers needed to necessarily see all that if they Googled me.

I contribute to some conversations now. It feels a little bit more awkward to me because I am not on the in-house side anymore. I have a lot of thoughts about how to be a successful in-house practitioner and how to be successful if you’re an outside counsel, but I do have to acknowledge that I’m on the other side as a solo. Twitter is a great place to network, whether it’s #In-House on Twitter. Appellate Twitter is also awesome, and that’s another place where I’m always so pleasantly surprised by how willing people are to share time and resources with potentially complete strangers to help lift them up. It’s a mentality of abundance that people are willing to do.

I love that mentality of abundance. Karen, this has been a great conversation. We’ve enjoyed hanging out with you and hearing about your experience and setting up your practice. This has been a great way to spend part of our afternoon. As we get ready to close out, we’ve warned you in advance that we like to ask our guests for a tip or a war story as a parting thought. Did you have something that you would like to offer?

I’ll share a tip. I’ll stay away from the war stories because I’ve had so few clients over the past couple of years that I feel like I can’t get too much into specifics on war stories there. We were talking about effective communication, and to the extent that maybe your readers haven’t thought about it before or haven’t heard of this particular train of thought before, one of the things I think about is when you’re emailing, look at the real estate on your iPhone. That’s how much space you have to get your message across. There are a lot of people who balk at that and think, “There’s so much more analysis and my client needs to know so much more,” but everything high level that the client needs to know should be able to go into that space.

That’s why when we go back to talking about effective communication, it does take so much time and effort to make those concise communications that allow your client to know immediately either what it is you need. If you need something from me, it doesn’t need to be at the bottom of a two-page email or a three-paragraph email. I need to know right away, especially if you’re dealing with the general counsel who’s getting hundreds of emails a day, or if you’re making a recommendation, make that a very compact, plain-language recommendation that is going to intuitively make sense to your client and allow them to say, “Done. We can move on to the next thing.”

Those are great tips. It’s something that I know I struggle with as an appellate lawyer because I want to do the brain dump into everything. I always have to write too much and then edit it back.

I do the high-level summary, then I may do a brief one-paragraph explanation, and then I’ll say more information below. That’s where I can get into the meaty nitty-gritty about what the analysis is and why, and all the various factors. If the client wants to read it, they can. If they want to come back to it, they can. Otherwise, they have everything they need up above.

That’s a great tip. Thanks again for being with us. We appreciate the chance to visit with you. We’re grateful to have you.

I appreciate the chance to visit with you all. I’ve enjoyed our conversation, and I appreciate you giving me some time.


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