Senior Associate Executive Director and General Counsel for the American Bar Association

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Annaliese Fleming, Senior Associate Executive Director and General Counsel for the American Bar Association, joins M.C. Sungaila to talk about her experience leading the ABA's legal function. Listen in as Annaliese touches on her wide-ranging legal expertise from private practice to teaching and now as a trusted in-house advisor. 

Note: The thoughts and opinions are those of Annaliese Fleming personally and not official positions of the American Bar Association. 

This episode is powered by Clearbrief, Trellis, BriefCatch, and CSBA.

Relevant episode links:

American Bar Association, All About Love

About Annaliese Fleming:

Ms. Fleming, who currently serves as General Counsel for the American Bar Association, is an attorney with inhouse and law firm experience in the areas of intellectual property, litigation and dispute resolution, commercial contracts, nonprofit law and association law.

I’m very excited to have join us, Annaliese Fleming. She is the Senior Associate Executive Director and General Counsel at the American Bar Association. Welcome, Annaliese.

Thank you. I’m happy to be here.

I’m interested in having you because you have a wide background in the law from private practice to teaching and then in the general counsel position at the American Bar Association, which itself is a unique and storied institution and is playing an important role in the law as well. I’m excited to go through that. Let’s start with you and how you decided to come to the law. What intrigued you about being a lawyer and what first sparked you to think about doing that?

The idea probably first occurred to me as early as high school. I did a mock trial activity when I was a senior in high school. We prepared a canned legal case. We went down to the courthouse and put it on with teams in front of an actual judge. I enjoyed that experience. It was a great deal. I enjoyed being on my feet, talking in front of a judge, and examining a witness. I found the process of putting together a story of the case and presenting that to be something that I enjoyed. I carried that with me into college.

I had a General Liberal Arts education in college. I majored in History and Women’s Studies, but it always kept in the back of my mind the idea that law school was probably where I was headed. Ultimately, I did go straight through from college to law school to practice from there and never looked back. It turned out to be a good choice for me in many ways.

The mock trial programs continue to this day in high schools around the country. That is an important highlight for those who volunteered to do those mock trials. It can make a difference and help people discover a career they might be interested in very early on. That is a heartening tale for those who do that work early. I have a friend, my co-clerk from the district court who does that regularly. She hopes that there will be at least 1 or 2 inspired like you were from her work.

Did you go into litigation then after law school since you enjoyed that and the trial?

I did. I went into litigation and many of the courses that I took in law school ended up being litigation-focused. Many of my favorite courses were Evidence and Civil Procedure, to the process-focused courses. Federal Jurisdiction drew my attention and my interest. At Northwestern, where I went to law school, they have an Integrated Trial Advocacy course that is part and parcel of the Evidence course and the Ethics course as well. You take all three together and they inform each other. That experience helped solidify for me and that litigation as well.

That is a good way to learn, too. Evidence is best learned being applied in a real situation instead of in theory only. You can also figure out whether you enjoy it that way by applying it.

That experiential piece is what drives home the learning. If you enjoy being on your feet and dealing with those types of issues on your feet, that is a good indicator that litigation might be something for you. The other piece that informed me was that I enjoyed the writing quite a bit. I liked my Legal Writing course and the writing that I did in other courses. I knew coming out of law school would be whatever I was going to do had to be a big component of it that would bring me some professional satisfaction.

The experiential piece is really what drives home the learning. If you enjoy dealing with those types of issues on your feet, that is a good indicator that litigation might be something for you.

Did you like to write before law school in other types of writing as well?

I did. I gravitated to Humanities, Literature, and History courses. All of which often had a pretty significant writing component. Even as far back as high school, those were courses that I tended to take as electives, advanced composition, and things.

I remember having an impression of myself as being a good writer until I got to law school and they completely deconstructed your writing and reconstructed you. I remember being shocked: “But this was what I was always good at.” IRAC and all of the other things, you had to be deconstructed and then reconstructed. But I do enjoy legal writing which explains why I am in appellate law.

Did you go to private practice right after law school?

I took a summer associate position after my second year of law school at a larger firm here in Chicago. I stayed with that firm for a few years and then ended up going to a slightly smaller, more regional law firms. It was the best of both worlds. It was a smaller firm that had a national practice. I was still exposed to the type of work that I found very interesting, which was Complex Commercial Litigation. Eventually, I developed a focus in the intellectual property area as well. I stayed with my second law firm for 12 to 13 years.

You went and taught for a while. I’m curious about that transition. What facilitated that and what did you learn from teaching?

It was an opportunity that arose. I ended up taking a specific opportunity that had come up for me. It was a risk. I thought pretty seriously about it because it was a fairly big change. I knew that I finished in the law firm environment and I wasn’t exactly sure what came next for me. That had been my alternative. I have a number of teachers and professors in my family. That had been an example that I had seen, including my mom. I thought, “It is a little bit of a risk, but I’m going to take it.” I have always had an outstanding question in my head about whether I would enjoy teaching in the classroom.

I decided to take it. I ended up teaching for two years in a PhD program in Leadership, which was a degree that was very geared for practitioners who needed to take their credentials to the next level. That ended up being a number of teachers who needed a PhD for achieving the next leadership level and administration. We had some folks from business, a number of people from the Armed services, and a variety of different industries and professions, but people who needed that credential to go where they next wanted to go.

It wasn’t necessarily lawyers.

There were a few lawyers and a few law enforcement officers. They brought some interesting stories and great things to the classroom. It was a diverse group of people. I loved it and I enjoyed the teaching aspect of it. I have carried some of that with me as I moved on in terms of teaching and mentoring younger lawyers. Although I enjoyed the classroom, there were some things that I missed about the practice of law. 

The practical aspects of problem-solving are very satisfying to me, serving a client and helping them figure out how to address the need that they have or the problem that they are trying to solve. That aspect was missing for me in academia. After a couple of years of teaching, I came back to the practice of law and that was when I made the transition to the in-house world.

From what you have described an in-house position seems like the perfect next step after that because you have the practice experience, you like counseling, and engaging practically with legal problems. You are very good at communicating the issues to a range of constituents, whether they are lawyers or executives who are grappling with the problem in-house. That is a unique trait of yours and is important for being in-house, but it is almost like you couldn’t have gotten to where you are without the combination of all your experiences together, including teaching, which rounded out your ability to speak and communicate well with all of the different kinds of stakeholders.

That is how I think about it, too. I had already been on my feet in terms of being in court and trying cases, but it is a different way of being on your feet when you are engaging with ideas at that depth. It helped me hone my skills in terms of speaking to people, but also thinking on my feet and processing deeply the ideas that were being presented to me in a way that I could then respond in kind. I agree. Teaching provided an opportunity for me to work on certain aspects of those skills that I didn’t have in the same way in practice. The combination of the two of them did make in-house the next logical step for me.

What I found is that it is the perfect fit. While the private practice and teaching were a good fit in many ways, putting them together and being able to use all those skills in the in-house setting is what has been for me. That does accurately describe it. I enjoy the practical aspects and engaging intellectually with different legal problems. The ABA has been the perfect place in which to do that because it is a very unique organization that encounters a law in so many different ways that it is provided the place where I was able to bring those things together.

The ABA position is perfect for that, too, because it is very eclectic in terms of what is involved. Let’s talk about how you came to apply for the ABA. How did you learn about the opening and then how did you start with ABA? You are currently General Counsel, but you started in a different position, right?

I started in 2015. I was aware there was an attorney retiring from the general counsel’s office. She had been primarily charged with handling the amicus briefs and staffing, working with the Standing Committee on Amicus Briefs, which is how you and I met, and litigation matters. When I originally came, I came to do those particular things. I had a friend who was a different attorney in the office and she was aware of the openings. We had stayed in touch. We had been together at one of my previous law firms. She let me know about the opportunity, so I applied.

I was particularly drawn by the idea of supporting the Amicus Committee because I love to write and talk about writing, analyzing writing, and editing. That seemed like a great opportunity to work on interesting and important issues that were being heard in the Appellate Courts and Supreme Court. That was the original draw for me in terms of coming to the ABA. I joined in 2015 and then spent the next couple of years working in that area, supporting litigation matters and the Amicus Committee.

Do you want to talk a little bit about what is involved there and how that works for the ABA? That is such a rare opening for that position because people tend to stay in that position. Your predecessor was there for a long time, working with the Amicus Committee. It is an interesting job. People like it and like to stay with it if they are attracted to it and it is a good fit for them.

The Amicus Committee itself is appointed by the ABA president and generally consists of experienced appellate lawyers and/or US Supreme Court practitioners. That committee works together with you or your counterpart now that you are a General Counsel and coordinates with a number of stakeholders within the organization, which is also what makes it a challenging position in that regard because it is not writing the brief. Maybe you can describe what things that involves.

Don't be afraid to let people know what you think.

It is a unique approach to preparing Amicus briefs because there are so many different stakeholders within the ABA. That process, in many ways, begins with the sections, divisions, and forums that are organized around substantive areas of the law. For example, the criminal justice section may have particular issues that it is following in the courts and that is of importance to it and might decide to submit a request for an Amicus brief in a particular case that is going to be heard by the United States Supreme Court. That whole process involves a number of different entities within the ABA.

First, the request is vetted by the Amicus Committee, which are ABA presidential appointments. Those are experienced appellate and Supreme Court level practitioners who take a look at the request and ensure that we have a written policy that has been passed through the House of Delegates that supports the position that we are being asked to take in an Amicus brief. It also takes a look at the overall context of the case to determine whether this is a case in which the ABA can make a significant contribution to the issues that the court is considering.

As an initial matter, the Amicus Committee makes a decision as to whether to grant the request or not. What that does is if the request is granted, it begins the process of preparing the Amicus brief, which involves a number of other kinds of entities and groups. We usually have pro bono drafters. We are very fortunate that the legal profession does a lot to support the ABA in the preparation of these briefs. A drafter is usually identified at the application stage. Once that request is granted, the brief begins to be prepared and that process is very iterative with the Amicus Committee.

The committee will review a few drafts of the brief and provide feedback and input. Ultimately, it approves the brief for filing it then involves the executive committee of the Board of Governors, which will also review the brief and make the same determinations that it is appropriately supported by ABA policy and it is going to make a significant contribution to the court’s consideration of the issues. Finally, it is high quality and meets the standards that the ABA has for its briefs.

Only then once the brief has been vetted and approved by both the Amicus Committee and the Executive Committee, then it is approved for filing. It is a fairly lengthy process. It can take several weeks, even 6 to 8 weeks, to get through that process and to the point of filing, but there are a number of different stakeholders involved, including both of those committees.

The section remains involved throughout and provides feedback as well. They tend to have substantive expertise, which is important to bring to that process. The whole process is managed by the attorney in my office who is covering that, whether it was me or, subsequently, my designee. The whole process of shepherding the brief through falls to my office.

There is an indication of the breadth of the legal areas that you are involved in-house for the ABA. You have a sampling of that in the range of the policies. I remember being very surprised. The most surprising thing was the range of areas in which the ABA does have a policy, whether it is from immigration, death penalty, other criminal law aspects, ethics issues. There are so many areas that the ABA touches on with official policy. There are lots of different kinds of cases that you are involved with. You have to be adept at moving between those and calling on the expertise of the different departments within the ABA that do deal with those issues on a regular basis and then incorporating that.

The other thing I learned from the Amicus Committee working with you in that role was seeing how we all work together as an extended in-house team for the ABA with regard to the briefing of being on the standing committee. It was something I least expected to learn from bar service, but it was in that setting. As you are a great example of how you were dealing with all of the different stakeholders, but also taking our responsibility pretty seriously as helping your office manage all of these several different briefs at once sometimes when issues come up. It was a great experience. You also did other things, IP and some litigation in addition to the standing committee.

I started out doing litigation. When another attorney left who had been handling the intellectual property side of things, I took on that work as well. I had a background in IP litigation, so that helped. We have a publishing business. There is not a lot of copyright work that happens at the ABA. There is a trademark portfolio that hovers around 80 trademarks. That involves a number of projects annually.

I had not thought about that. There are trademarks as well as copyright issues with ABA publishing. Tell me, how long were you in those ever-expanding positions within the ABA?

I did continue to take on things as they become available. In many ways, the general counsel role was a natural progression. Our previous general counsel ended up passing away very suddenly after the annual meeting in 2020. The position opened. At that point, the ABA conducted a national search and I applied as one of the candidates. I went through that process and was ultimately hired to take on the role, which I did at the end of October in 2020.

In many respects, having been at the ABA and taken on a number of different roles had exposed me to enough of the organization that I had more of a global understanding perhaps than some of the external candidates might have brought. That was very much an advantage in terms of seeking that role and then being chosen to take it on.

The ABA is a unique special organization and it can take time to figure out how all the pieces fit together. You hit the ground running, having been working internally with several different aspects of the ABA prior to the general counsel role.

Even if I didn’t know the answer, I knew who to ask, so that was very helpful.

That is the first question of knowing who to ask because that is generally not written down, but this is the person who would have the information either institutionally, they have been with ABA for a while or even if they don’t have it directly, they would know where to send me. All of that stuff is very important to functioning.

When you applied, did anyone encourage you to apply, were you hesitant to apply, or did you say, “This is something I’m interested in doing if they agree it is a good fit?”

Initial conversations about this as a possibility at some point, but nobody had thought that it would come that early. I had identified it as a career goal of mine. I wanted to be a general counsel and I have wanted to be the general counsel at the ABA if that was available to me. I did feel strongly about applying and taking the opportunity while it was open. I did have to think through, “Am I ready?” I thought this was maybe 3 to 5 years.

That is why I asked that because it seemed suddenly it was there. I know that what a lot of women tend to do is check first to see if they have all of the skills identified for a job and say, “I want to have these three more skills before I would apply to that.” But that is not going to happen if the opportunities are available now. Sometimes getting over that hurdle can be a little bit difficult mentally.

I will confess, I had some of those thought processes as well thinking, “Maybe now is not quite the right time.” We are also in the midst of the pandemic and that layer of additional work and concern about, “Am I ready for this?” Ultimately, I talked to myself around to the fact that I did think I was ready enough. I had some experiences and skillset and certainly a knowledge of the organization internally and the people. That is an advantage as well.

When you’re confronted with a problem, try to look for a practical solution.

Even if I haven’t gotten to the point where I served on the business continuity task force enough to be comfortable with all of that work, that is okay. I can learn that aspect of what I need to learn. What I do bring is an understanding of how the organization works and how to deal with certain unique aspects of a membership organization, and how important it is to involve volunteer leadership. I had certain things that I could bring to the table that maybe other candidates would not have. 

The ramp-up period would be particularly challenging for someone outside the organization during COVID because everybody is remote and trying to get that sense. It would take much longer. It would seem like because of that, your experience internally would be even more of a plus than in other circumstances.

It was very helpful as it turned out to have that. I have thought several times, I’m not sure how an outside candidate would have handled them and much more challenging. People are starting new jobs. It helps to have some of the insider knowledge.

How is it going?

I’m much more comfortable than I was in months 1, 2, or 3. It has been an exciting year and an interesting one. A lot has happened. There is no playbook for how this pandemic has evolved. That has been a matter of keeping up with it and the way that all other organizations are keeping up with it and trying to figure out what is the best thing to do to protect health and safety using that as the guiding principle. It has been great. If I try to describe for you everything that I have learned in the course of this time, we would be here for days. It has been a challenging, rewarding, exciting, and interesting time. It is a way to take on the role, but I have learned a lot. I’m sure that will continue.

You have been in the role for a little bit. Do you have any words of wisdom or advice for people who either are in-house and thinking about or have that on their career goal list of becoming general counsel or even somebody who is in private practice who might want to go in-house. Are there are any tips that you would have for them or anything that you learned that you were surprised to learn but would be helpful for someone to know?

A couple of things have stayed with me throughout. There was some advice that was given to me early on by the person who had held the general counsel position on an interim basis while the search was being conducted. He gave me some good advice. He said, “Don’t be afraid to let people know what you think. If you have thoughts or an opinion on something, don’t shy away from offering that that is what people need from you.” That has been great advice. Even when my opinion or my thoughts differ from thoughts than others are sharing, that only makes it that much more important that I share it so that there is a diversity of thoughts on the table and perspectives when you are considering a solution.

I have gone back to that advice several times because that was very helpful advice. The other is not a piece of advice that anybody gave me, but it is something that I always do. That is to look for a practical solution when you are confronted with a problem. That is particularly important in-house. You are always dealing with limited resources in terms of time, money for outside counsel, and things of that nature. A practical solution can often solve the problem in a way that everybody is able to move on and not worry about lingering risks.

That is one of the things that I always go to when confronted with an issue or a problem. Is there a practical solution to this that we can put to rest? That can differ from the legal solution in many ways. It can be equally as important, especially when you are talking about running a business. That is another thing that I always go to and would advise other people to keep in mind.

You always hear general counsel saying they don’t want to be the department of no for things. We don’t want to always be saying no on legal grounds, but even beyond that is the point you’re making, which I think is broader than that. Things come to you. There are problems that need to be solved through the legal system, a way to solve it, but there might be other methods of solving it that practically resolve the issue for the organization and allow the organization to move forward without having to get into that, which includes expenditures of money and stress and other things that are involved.

That is what you are extraordinarily good at, engaging with different stakeholders with different interests, levels of knowledge, and different pieces of knowledge of the organization, which with the ABA is the case. It is the elephant, which part of the organization you are involved with seems very different from other parts. You have got to engage all of that knowledge. Looking at it, taking all of that and saying, “Is there a practical approach to this?” Whether you are dealing with people or dealing with the larger problem.

It doesn’t surprise me that this is the sweet spot job for you because you are so very good at that. I have learned so much watching you work with all kinds of different people and gain their confidence and trust, especially at the executive level within the ABA. In some of the calls we have been on, I have noticed that you get their respect in part because you do consider practical methods of solving things, and that is important.

That is a lovely compliment.

What advice would you give to outside counsel working with general counsel or your team in terms of how can they make that job that you are doing easier, how might they approach problems and solve them for you as well?

Sometimes you present the legal problem without remembering to state the underlying goals or the considerations. I would advise outside counsel to not shy away from asking those questions. Something as simple as, “I understand the legal problem and you have been sued these claims, but what is your overall goal here? Where would you like to get in a perfect world?” To understand what some of those underlying considerations might be. Listening is probably the most important skill that all lawyers have and should hone. It is certainly true in that context as well.

I think about it in the appellate context is finding out first, “Is the risk posed by this particular case or appeal limited to this case?” In other words, is there a high exposure in this case or is there a potential for creating a law that could impact other cases as well? How you handle these two cases are very different depending on what is at risk for the organization and where are the risk tolerances. I try to do that in the appellate realm in that way, trying to figure out where does this fit in the risk calculus and how does the organization sees this as an existential threat or a particular threat that is discreet. That is important in everything. What is the larger goal?

It is something that we ask our clients in the business as well all of the time. It goes back to something you said about legal departments not wanting to be giving the no answer. I think about that as being the roadblock. I don’t want to just say no. I want to understand what it is that you are trying to accomplish, so that if what you are asking me, you can do, if the answer to that is no, then my answer can be like, “No, although here is that I think we can do. There is a way that we could approach it and resolve it.” The listening piece is important and asking those questions is as important for in-house counsel as it is for outside counsel.

I put that in the category of deeper listening. It is not just what people are saying directly, but getting to the underlying issues or concerns. Sometimes people name problems a certain thing and that is not its name. It is something else. If it is something else, we can deal with it in a different way that can resolve it faster than you think. That helps. In that way, you are able to uncover alternative paths for people, too.

When you don’t know the answers, knowing who to ask and who can provide you with that information can be very helpful.

You are very good at ferreting out what the big picture is and what is going on for the client and executives in the particular case. That comes in part from the teaching background that you are listening, recasting, and exploring things pretty deeply. That is an unusual background for a general counsel and in-house counsel to have that teaching, especially in the leadership realm, but it seems to be, as far as my observation, like a critical piece of how you do your job.

There are different kinds of listening. When you are listening to understand something, that is much different from when you are listening in order to respond to something. It is that listening to understand piece that is so critical in client service. That is also so critical when you are in front of a classroom and trying to gauge student understanding.

I’m trying to find the bridge or something that will spark for a particular student. To do that, you have to meet them where they are. I’m going to ask you a few lightning round questions to end with. What talent would you most like to have that you don’t have?

Singing. I would love to be able to sing. I love music so much. I listen to a lot of music and I always have. Music was big in my household growing up, but I cannot sing and it is painful for people when I do. I wish I was able to do that. That would be great.

Do you play any instruments or are you just a music appreciator?

More of an appreciator. I did play the clarinet in middle school and high school, but I did it pretty badly. It was not a skill I had.

I wanted to play the harp growing up. That was my chosen instrument, but my mother said I had to choose something that fit on the school bus, which was not the harp. It was a violin. I was in protest from that day forward of the violin because I wanted to play the harp. I played horribly and eventually ended the violin lessons, but I can sing. I did turn to that. That was good. I have always had an interest in wanting to learn to play the harp and still do. It is on the list, the harp and drums. I want to play the drums. It was fun.

Who are your favorite writers?

The one that immediately comes to mind passed away. She is a feminist writer named bell hooks, who wrote some wonderful things. I started reading her in college in some of my women’s studies courses. She wrote a lot on the experience of women of color, particularly Black women in the women’s movement, on how they had been marginalized by feminism.

I started with that, but then one of my favorite books of hers is a book called All About Love, which talks about love as a verb. It is something that you have to affirmatively do and choose to do as opposed to something that is or happens. She writes about it in a number of different contexts in that book, but that stuck with me. She is very much on the list of favorite writers. It was a tremendous loss.

I was so shocked to see that. I was like, “That seems a little too soon.” Someone that I had grown up reading in college and even in high school as well.

For what in life do you feel most grateful?

I have two healthy children. I feel probably most grateful for them and their individual personalities and interests. They are teenagers. I’m seeing them become the adults that they are going to be. It is a privilege and something that I am very grateful for.

Given the choice of anyone in the world, who would you invite as a dinner guest?

Do they have to be alive?

They don’t have to be alive.

Virginia Woolf. I would love to understand more of the experience of being a different woman at a different time and how that was for her or what that was like.

Who is your hero in real life?

My paternal grandmother. There is a theme here. I’m seeing it emerge. It is also a different woman in a different time. She loved education. She wanted as much education as she possibly could. She was born on a farm in rural Western Kansas. Other than high school, there were not a lot of expectations for her to finish anything, but she went to college. She majored in Home Economics because it was the late ‘40s and that is what you could do as a woman at that time. She finished college.

She then went on to have five children. After having five children, she went back and did a PhD in Educational Administration and ultimately had a career in that field. I was very close to her growing up. She taught me how to bake. She was a big, important person in my life. When I look back and reflect on her life and the things that she accomplished, even when they were not expected or encouraged, she wouldn’t necessarily have had a lot of role models who had achieved those things. I think of her as my hero. 

Listening to understand is much different from when you're listening to respond. And it's really that listening to understand piece, that is so critical in client service.

It is such a full life at different times of her life. That is a good example as well.

She was able to have everything that she wanted to have, even if it was at different time. 

You can have it all, but you can’t have it all at exactly the same time.

What is your motto if you have one?

I don’t know that I think about it in this world all of the time, but it is: persevere. Things can always get better. Sometimes they get worse, but they can always get better, too. If you get stuck in a moment, you can remain there. I prefer to always think ahead, try to figure out how to improve things, and how I want to get where I’m going even if I have some setbacks or things that I have to contend with along the way. It is to persevere, keep trying, keep going, and keep moving forward. That is a lot of words, but the motto can be summed up as persevere.

Sometimes that means taking the step in front of you but moving forward is important to do. It is a good observation and advice in general for people. If things are dark, all you can do is take the stuff that is right in front of you, but at least you are moving forward.

That step can lead to another, which can lead to another. It is getting started that is sometimes the hardest.

Thank you so much for joining us, Annaliese. I appreciate it. Thank you for taking a step with us and sharing your journey and some advice for other women in the profession and those who aspire to it. Thank you so much again.

It is my pleasure. I enjoyed talking with you. I look forward to reading some of the other interviews as well.

Thank you so much, Annaliese.

Note: The thoughts and opinions are those of Annaliese Fleming personally and not official positions of the American Bar Association.