Episode 109: How Executive Coaching Can Breathe New Life into Your Legal Career with Andrew Elowitt, Managing Director & Founder of New Actions LLC


Episode 109

What you’ll learn in this episode:

  • Why a growth mindset is the key to making effective change
  • Andrew’s tips for beating resistance and making changes stick
  • Why lawyers need to adapt their professional approach to become effective coaches and mentors 
  • How to choose the right executive coach
  • What lawyers of all levels can expect to gain from coaching

About Andrew Elowitt:

Andrew Elowitt JD MBA PCC worked for over twenty years both in law firms and as the head of a corporate legal department before becoming a practice management consultant and professional certified coach. He is the Managing Director of New Actions LLC, a firm that specializes in talent, strategy and leadership development for law firms, businesses, and government agencies.

His work focuses on the people side of legal practice: how lawyers manage, lead, thrive, change, and find satisfaction. He is regarded as an expert on the use of coaching and emotional, social and conversational intelligences in leading and managing legal organizations of all sizes.

Andrew is a Fellow in the College of Law Practice Management, an International Coach Federation Professional Certified Coach, Vice Chair of the ABA Law Practice Division Publications Board, and founding member of its Lawyer Leadership and Management Board. He is the author of numerous articles and is regularly invited to conduct workshops and retreats for his clients and to present programs to bar associations.

Additional Resources: 


Coaching is a powerful tool that can help lawyers in all stages of their careers become more effective leaders, mentors, and professionals. The legal industry has embraced coaching over the last 10 years, thanks in no small part to the work of Andrew Elowitt, founder of coaching firm New Actions and author of books “The Lawyer’s Guide to Professional Coaching: Leadership, Mentoring, and Effectiveness” and “Lawyers as Managers: How to Be a Champion for Your Firm and Employees.” He joined the Law Firm Marketing Catalyst Podcast to talk about how lawyers can face and overcome their resistance to change; why a growth mindset is necessary for lasting transformation; and how lawyers should choose the right coach. Read the episode transcript here. 

Sharon: Welcome to the Law Firm Marketing Catalyst Podcast. Today, my guest is Andrew Elowitt. Andrew is the managing director and founder of New Actions LLC. His firm provides high-level coaching, practice management consulting and retreat facilitation services to law firms and other professional service firms. He is a former lawyer and corporate executive. He’s also an in-demand speaker. He is a very accomplished author who has been on the podcast before with one of this coauthors, Marcia Wasserman. We’ll hear all about his journey today. Andrew, welcome to the program.

Andrew: It’s great to be back, Sharon.

Sharon: It’s great to have you. Thank you so much. Tell us about your journey. How did you get to where you are now?

Andrew: I had been practicing law for 15 years, first in firms and then I went in-house. It wasn’t something that hit me suddenly at 15 years. I realized I was a good lawyer and I was well-compensated, but my passion for the law, for legal practice, was ebbing. I wanted to do something more. I wasn’t sure what it would be, but I definitely wanted to have a second act. 

So, I got to that point 15 years in, like I said, and it was a matter of some awfully good luck. My best friend’s weekend hiking buddy was a senior organizational development consultant who was putting on learning opportunities for an eclectic mix of people. I had known him socially, and I was introduced to him. I talked about what he was doing with the learning groups. He had a clinical psychologist, a college professor, an educational consultant, and a woman who did film editing and writing, so a lawyer in the mix made it all the more eclectic. Once I started that learning group, I was fascinated. It was like all the lights going on on the Christmas tree in Rockefeller Center. I went, “This is so interesting. I want to do this.” Then I started to train, and I probably read more in those first two or three years that I was training with my mentor than I had practicing law in the prior 10 years. 

Then I made the transition into doing organizational development consulting. We were working with a lot of tech companies in Silicon Valley. Over time, slowly, I started to pick up more professional services firm clients, lawyers, accountants. A lot of my friends from the legal world were now in managerial positions. We’d get together and they’d say, “Andrew, we’re having this problem,” and I’d give them advice. After about six months, they said, “You know what? We’ll pay to have you go into the firms and help us with these things.” I went, “Oh my gosh, there’s a niche here.” So, I started working with lawyers then. 

At that time, which was the early 2000s, coaching in the legal world was not well understood. People thought I was a life coach. They had all kinds of misgivings, and I had to overcome that initially in making the transition. At this point, coaching is very well known and respected and utilized, not fully utilized, but utilized in the legal profession.

Sharon: Do you think that’s more in California? When I talk to people in other areas of the country, they don’t really know what coaching is. They’re going, “Coaching, what’s that?” 

Andrew: Yeah, occasionally I get that. I don’t think there’s a big geographic difference anymore. Maybe on the coasts there’s more understanding of coaching. The legal community has followed the business community. The business community was a much earlier adapter and user of coaching. You certainly saw that in the tech companies. One of the reasons why was because you had a lot of younger, relatively inexperienced managers coming in, and they needed help. Brilliant people, great subject matter experts, but they didn’t know how to manage, especially managing people. That’s one of the reasons why there was a lot of traction for coaching in tech centers, both on the west coast and the east coast. 

Law has followed that, and I think it’s a matter of what the business models are for businesses versus professional services firms. As you know, partners or senior attorneys have their producer/manager dilemma. They’re the ones that are on the factory floor grinding out the equipment or the product. At the same time, they need to manage, but do they have the time? There’s a built-in tension there. Do I step away from billable hours to do the work? Do I step away from client development to do the managerial piece? It’s a built-in dilemma. You don’t see that on the business side. On the business side, with the executives I work with, which is anywhere from 40% to 60% of my practice, they are managers. Their job is to manage the people that report to them and to collaborate with the people in their organizations. It’s different than in law firms.

Sharon: Law firms are their own animal. One of the ways is exactly what you’re talking about. You have tension. What do you tell people who come and say, “I love the business side and I like client development, but I don’t like the law. I don’t like to write briefs. I don’t like to read them. What can I do?”

Andrew: First of all, that resonates with me because that was my feeling about the law. I know I was a good technician, but I much rather would have been negotiating. I think that’s one of the reasons why I was happy going in-house. I got to be the client, and I was more involved in the business affairs of my organization. 

For those people, I think it’s great that they have wider interests. The people who like client development, they’re the future rainmakers in a firm. The people who like doing the managerial piece are really important. Now, there’s a problem because they may be very good at it, but firms are still slow in rewarding and incentivizing people to take on those managerial roles. 

One thing we’ve seen in big law, the largest law firms in North America and around the world, is the emergence of professional managers. People that may or may not be lawyers are now doing the administration and the leading of firms. There can be challenges to that. In a lot of jurisdictions, you can’t have nonlawyers, people that are not certified as lawyers, being equity holders in a law firm. That makes the compensation and incentivizing issue a lot more complicated, but I think we’ll see more of a continuation in that direction. It’s great to have people in firms that are interested, passionate, experienced and competent in management. It makes a big difference in the bottom line.

Sharon: I had forgotten how it’s become so professionalized on the business side in many ways. I can’t remember; it’ll come to me later. I was trying to remember when I was at Arthur Andersen. There was such a big dichotomy between fee earners, non-revenue generators and revenue generators. I always felt like, “What are you talking about? We bring in this much.” 

Anyway, you said you were doing training in organizational development or coaching.

Andrew: It started out with organizational development. That was the focus of our learning group. It was great for me. I was with people more senior than I in terms of work experience, not necessarily in terms of age. We started with a couple of learning groups in Los Angeles. Then my mentor, Don Rossmoore, got invited to Xerox’s Palo Alto Research Center, PARC, to lead learning groups there, so we had other professionals and executive coaches that were in-house for Xerox. We had people from Apple, Hewlett-Packard, Sun. It was the whole list of tech companies. This is back in the 1990s. It fast-tracked me to have all those people available to learn from. 

Our last learning groups morphed into a consulting group that was a bit informal. Very different from law firms, where everything is very structured. This was, “Do you have the availability? O.K., we’ll work together on this engagement.” I learned a tremendous amount there. We were usually dealing with larger issues throughout an organization. 

What I found in doing that was I loved the strategic part, the systems part of that, but it really comes down to implementation. When it comes down to implementing the changes we’re recommending, that goes back to the individual. Often the individual executives and managers were having difficulty implementing the changes they knew they needed to make, including changes in the organization, changes in the team they were leading, or changes in themselves. It’s the individual.

That’s where I really began the transition into coaching. I didn’t think I was very good at it initially. I still feel that way. I had to unlearn a lot of qualities and approaches that made me a good lawyer, but not necessarily a good coach. For example, as a lawyer, you need to be prescriptive and directed. You’re there to provide a solution. A client comes to you with a problem, then, “O.K., well, this is what you should do.” That doesn’t necessarily work well when you’re coaching. It’s better to work more collaboratively with your coach-ee to help them come to their ideas and figure out what they need to do. I had to stop myself. I had to restrain myself from jumping to solutions and saying “Here’s the roadmap. Here are steps one through five. Do them.” That was me at the beginning. I had to sit on my hands and zip my mouth and go, “I have some ideas about this, but I’d like to hear from you first. What do you think would be a good approach?” It’s bringing them more into the picture. 

That was one of the biggest and hardest changes for me, but I found I really liked working with executives. There’s something about working with people one-on-one I found very satisfying, far more satisfying than working with people one-on-one in the legal capacity. I went in that direction with executives and lawyers and a few other service professionals from time to time, but I wouldn’t identify myself in those positions. That’s pretty much the journey that I took.

Sharon: Do you find that you have to put on a different hat when you’re working with a lawyer, and then another hat when you’re working with an executive?

Andrew: That’s a great question. It depends on the lawyer and the executive. Sometimes I have to put on a different hat with the same person from one session to the next depending on where they’re at. With lawyers, Sharon, it’s usually a matter of the issues we’re dealing with. On the executive side, it’s pretty much pure management and leadership skills. Lately with the pandemic, resilience and finding a healthy work/life integration are huge, huge issues. For the last two or three years, that has been a theme in almost all of the coaching I’ve done. 

On the legal side, it’s different. It’s not pure management and leadership. At the younger levels of an attorney’s career, we’re more often focused on issues of productivity, time management, work-flow management. They are on the receiving end of delegation and feedback, so a lot of it is helping them learn how to receive delegation and feedback and how to help them make the people giving them the feedback and delegation even better. 

It’s a sweeping generalization, but I think it’s true that lawyers don’t have a lot of formal training in managerial skills. Some who came to the law after working in another area may have that. Some who took management classes in college or grad school, they may have some familiarity. But basically, when it comes to people management, lawyers don’t know a lot. They are replicating the ways they were managed, which means they may be using managerial and leadership approaches that are two generations old, which are not great with millennials and Gen Z.  So, a lot of is helping people learn how to manage. 

Now, I said I started with people at the lower level. As you get higher, then it is learning those managerial skills, delegating, giving feedback. How do you hold the people that work with you accountable? How do you collaborate with other people? As you go further up, it becomes more client-facing, so it’s about developing those client relationships. Then we get into business development. I’m not a business development specialist, but I’m very good at helping attorneys that have support for client development within their firm and may even have dedicated client development people. 

They know what they should be doing, but they’re not doing it. It’s the classical example of the knowing-doing gap. This is something that’s not unique to lawyers. There’s something we know we should do, but do we get around to doing it? No. That can be the case with a lot of lawyers when it comes to business development. I’m very good at helping them understand what’s holding them back. Typically, it’s nothing external; it’s nothing in the firm or the environment. It’s something in them. We acknowledge what the inner obstacle is and we work past it and through it. I have a good record of getting them into gear and getting them developing clients. 

Finally, when we get to partner-level, practice area heads and executive committee members, then it’s a lot about leadership and management. That’s where there’s the most similarity to the business side or the executive side of my practice.

Sharon: Do you work with people at all different levels, depending on where they are when they contact you or the firm brings you in? How does it work?

Andrew: For firms, it’s virtually all levels. Large firms will bring me in. I’ll work with their professional development or talent development people. Most often, they have a high-potential associate and there may be a couple of things that they’re struggling with. As I think most of your listeners will know, it’s expensive to find new people and onboard and train them. You don’t want to lose that human capital. So, coaching can be very helpful and cost-effective in helping those people overcome the problems they may be having. 

It may be something like time management. You have an associate who’s starting to trend late on their deliverables. It’s the work they need to get to partners. It’s overly simple to say, “Oh, they need to work harder and faster,” or something like that. It may be an issue—it often is—where they’re not doing a good job of pushing back against the people giving them work. There are lot of people all over the world and there are a lot of associates. They’re hesitant to say no to a partner when a partner hands them a piece of work. What they end up doing is overloading themselves because they are overly optimistic about what they can achieve in a given amount of time. So, helping them learn how to push back is a way of dealing the time management issue.

Sharon: I can see how it would be very hard to say, “I don’t have time,” or “No,” to a partner. That must be very, very hard.

Andrew: There’s a skill and art to it, a lot of finesse. With some partners even more finesse.

Sharon: Is there resistance? It seems like there would be. Maybe I have an old image of it, but it seems like there would be people who say, “I don’t need coaching,” or “I’ve failed if I have coaching.

Andrew: Happily, there’s less and less of that. That sense of failure, I don’t run into that much anymore. Usually with younger associates, they may feel like, “I should know this. This is a flaw in me. I’m not doing a good job of this.” Often, they’re their most severe critics, so I make it very clear to people I coach that I’m not there to fix them. Seldom am I dealing with somebody who really has a risk of being fired from a firm. It’s usually developmental. Usually, they’re worth investing in, and the firm is spending money to help them become more productive and a tighter part of the firm. 

The one thing you did mention is that some people think, “I don’t need coaching.” I’ll initially talk to a prospective coach-ee—and this works on the executive side or the legal side. I qualify them, which sounds like turning them into objects, but it’s coach-speak for talking to them to see if they’re coachable. Not all people are. Most are very earnestly interested. They want the help. They’re stuck. They don’t know what to do, but they know they need to do something. Occasionally, you’ll find somebody who points the finger at everybody else. They say, “I’m not the problem. It’s their problem, if you could just help them.” That’s not going to be a good coach-ee. 

The other thing you look for is a growth mindset versus a fixed mindset. People with a fixed mindset think, “This is all the intelligence I have, all the social skills I have. What you see is what you get. I’m not going to change. There’s not a lot of room, if any room, for improvement.” Why spend time, energy, money on dealing with a person or trying to help a person who is saying, “This is where I am and I’m O.K. to be there”? There’s no upside potential. You want people with a growth mindset who are curious, who are saying, “I want to learn how to do this.” It’s a challenge. You want people who can say, “I’ve really messed up doing this. I can tell you about the last three failures I’ve had.” That level of self-awareness and candor makes for a great coach-ee.

Sharon: I’m thinking there are some similarities. Sometimes a partner will say, “I know how to do it. I did it this way. They can learn how to do it this way.” Can that change? They may be resistant, or maybe they’re not coachable. What do you think about that?

Andrew: There’s often a degree of resistance in making changes. There’s a reason why we are the way are at a given moment. Often, it’s because something has worked well for us in the past, and that’s fine. It makes sense to me. It got you to where you are. Why change it? You don’t want to take that risk. But that mindset ignores the fact that our world is changing really quickly. 

Let’s use the example of working virtually. There were people that said, “No, I only want to have face-to-face meetings.” This goes for coaches and their coaching sessions as well as clients and people in their firm. But the world changed, and all of a sudden, we got a lot better working virtually. 

Sometimes you do run into people who are resistant. If you’re coaching them, you can start to work with them on resistance. You can say, “I can see why this would work for you. I can see the track record. I’m curious. What do you imagine might happen if you tried doing this differently?” I will lay out a scenario of what different would look like. When you start to engage them in that conversation, that’s where you listen and hear what their fears are, what their expectations are, why their fears may be justified. Often, they’re not. They’re thinking something horrible will happen, and you can say, “There is that risk, but here’s the opportunity. What do you think?” So, you can subtly, gently shift them. 

Sharon: It sounds like you have opened up people who were closed when you walked in.

Andrew: Yes, all the time.

Sharon: I know you went to the Institute of Management Coaching.

Andrew: No, my training didn’t include IMC. In terms of management training, I did get my MBA from Marshall School of Business at USC. The learning group supplemented a lot of that. A lot of it was self-study, but I also took workshops and got certified in Essential Facilitation. That was something I found extraordinarily helpful and is a big part of the work I do. There was also action science, which is, again, organizational development oriented. It helped me to understand the dynamics of organizations. 

The other thing in terms of training was my coaching training. One thing about coaching that is very different from lawyering is how you become a lawyer. Typically, you’re doing your undergraduate work; you’re going to law school; you have to take the bar exam. There are a lot of steps, a lot of certifications, that help with quality control. On the complete other side of the picture, we have coaching. You want to be a coach? Go to your stationery store or big office supply place, get cards printed up that say “coach,” and you’re a coach. There’s very little in the way of, at least, governmental oversight. The last I checked, which was a few years ago, I think the only state that said anything about coaching in their laws was Colorado. It said that coaching is not considered a mental health profession, so it was excluding coaching. Nothing about what you have to do to be a coach. 

So, it’s incumbent upon coaches to get training. There are a few organizations that sanction training and offer certification. I’m an International Coach Federation Professional Certified Coach. Boy, is that a mouthful! ICF is probably the leading and most well-known organization for certifying coaches. It’s not the only one anymore, but it is an effort to raise the standards of the profession and to make sure that people who are using coaches get somebody who knows what they’re doing.

Sharon: Did you have to take some training and go through at least one class? Or could you just send in your money?

Andrew: That’s a great question. There are some organizations where basically you’re paying to be on an online list of certified coaches in the area. That exists. I shake my head in dismay about that. As far as I see it, you have to go through an approved training program. Mine was Newfield Network. It was a nine-month program. I think we met three times for three or four days in person. There was a lot of virtual work, albeit this was so long ago that it was by telephone in between. It was rigorous. 

There are several good coaching programs. ICF approves them. They have lists of them. What we’re seeing more of, both on the executive side and in law firms, is that they want people that are certified coaches. Certification of a coach doesn’t necessarily mean they’re the right coach for you or they’re a great coach, but it does mean they’ve taken it seriously enough that they put time and effort into it. They know what they should be doing. Hopefully, they’re also doing it. 

Sharon: You’ve been a lawyer and an executive, but being a lawyer, I can see how that gives you so much of an advantage. I’m thinking about how many times we’ve had to write a press release and weren’t exactly sure—we did know, but we’re not lawyers. It gives you an advantage.

Andrew: Yeah, it does help. Especially in the past, it helped a great deal. If you look at studies of lawyer personalities versus the general population, lawyers typically are slower to trust other people. It makes sense. It’s not a bad quality to have considering how we need to protect our clients’ interests. But I found that lawyers and administrators in law firms are very happy that I have a legal background. 

There was this one moment relatively early in my career where I was sitting across a managing partner’s desk. He was starting to explain to me realization rates, and I held up my hand and said, “It’s O.K.” He stopped and went, “Oh, that’s right. You’ve practiced.” His shoulders sank down a couple of inches, and he sat back in his chair and said, “That’s so nice that I don’t have to go through all that explanation.” Understanding the context of what goes on in a law firm helps a tremendous amount. So, that is good. With that said, not everybody has to have a legal background. But I think some of the most effective coaches I know do have that background.

Sharon: I can see how that would make you very effective, especially being on the other side of the desk in any capacity. If you were a lawyer at one point, you know about doing the work and getting the work. There’s a difference there.

I love the name of your firm, New Actions. That’s what all of this is about, right?

Andrew: You nailed it, Sharon. Especially when I started the firm, there was, like I said, a limited understanding of what coaching was about. Coaching can be these wonderful dialogues and interesting conversations you have with a coach-ee. What you want to do is get results—at least, that’s my philosophy—and the results are helping people make changes. Where they are doing is not satisfactory for some reason. They may be unclear about a direction. They may need new skills. They may have difficultly working with people in the system of their organization or getting past that knowing-doing gap we talked about. It could be all those things, but people have to start taking new actions to get new results, better results. That’s where the name came from. 

Sharon: Do you think results last? Maybe they try the new actions once or twice and say, “Oh, that’s different,” but then they forget. Maybe I’m personalizing it. I’m thinking you forget. 

Andrew: Yeah, as I said earlier, there’s a reason why people do the things the way they do. It’s easy for people to revert back. That’s one of the problems we find with training in a business or a professional firm environment. I’m sure you experienced that in doing trainings with lawyers and seeing they’ve learned all this new stuff. They’ll do it for a couple of months, but without reinforcement, people do start to revert back to old behaviors. The six-month mark is my ballpark estimate. I liken it to having taken a foreign language in high school. You don’t take it in college. You don’t go to that foreign country. You don’t use the language. You lose it. It certainly happened with me. That is a problem. 

The difference with coaching is there is a reinforcement. Sometimes we do spot coaching or laser coaching. It may be three sessions. When it’s really short, we’re probably dealing with a specific issue or problem, but most executive coaching goes for six months. That’s our target area. Often, it may extend a little bit longer than that. In the first part of the coaching, you’re understanding the person, why they’re doing what they’re doing. Then you move into what they could be doing differently. In the middle third—and this is very rough as to the time—they’re practicing the new skills, the new behaviors. They’re understanding what works for them and what doesn’t. The last third is really more practice. It’s integrating those skills so they become second nature, almost automatic. That’s where what you learn in coaching can become sticky, if I can use that term. After you finish coaching, it’s going to stick with you. 

I was just thinking of this while on LinkedIn. A former coach-ee of mine posted that he got a promotion, and I sent him a congratulations. I got back a comment saying, “Thank you so much for your coaching. I’m still quoting you.” I coached him about four years ago. That was the kind of gratification I was talking about earlier, the difference between being a lawyer and being a coach. I don’t remember what I said or what he’s quoting, but it stuck with him. He’s using it, and he’s in a global world now. That made me very happy. I had a big smile for the rest of that day.

Sharon: As a lawyer, when should I consider getting a coach? What would I be dealing with? What should I look for?

Andrew: O.K., two different questions. Often, the lawyers I’m working with, their firms have contacted me or they’ve been instrumental. With that said, one positive trend I’ve seen is that younger lawyers are saying, “I would like a coach. I need a coach.” Lately a lot of them are saying, “I’m overwhelmed. I’m stressed. I have too much work for my ability to handle it. I need to get better organized.” They’re initiating that.

The first step for a lawyer at any stage of their career is that you’re dissatisfied with the way things are. You may have a good idea of where that’s coming from. You may sense, “I want to stop doing whatever I’m doing now,” but knowing what you want to stop doing is different from knowing what you need to be doing differently. The analogy or metaphor I use is think back to being on the playground. We had monkey bars, I think they were called. Those were the horizontal bars that went across. You grab one and then you swing to the next one. What you learned early on as a kid was that if you don’t have some forward momentum, you get stuck. Then you would end up letting go and dropping to the ground. In making changes, you have to be able to release the hand that’s on the back bar. Sometimes in coaching, it’s unlearning what you were doing. If an attorney finds themselves in that position, that’s where coaching might help. It’s not a panacea. It’s not perfect for everybody. 

I’m a good coach, but I’m not the right coach for absolutely everybody. Rapport is very important. Fit is a very important thing. Typically, when I work with somebody, I qualify them and they’re qualifying me. Do they want to work with me? It’s important that you feel a degree of comfort with your coach. As I’ve gone on, I think you can be too comfortable with a coach. You want a coach who can challenge you and be honest with you and be able to say, “No, I’m not saying this,” or “No, I don’t think is working for you,” or “Hey, it sounds like there’s an internal contradiction in what you’re saying to me.” A lot of coaching is helping people get past their blind spots. We all have blind spots. That’s not a failure. I think it’s wired into us. Having another person there, especially an experienced person who can help us see what those blind spots are once you recognize you have them, that opens up a lot of possibilities for taking new actions.

Sharon: You mentioned in some writings that you’ve helped people with difficult conversations. There are a lot of difficult conversations. Can you give us some examples in law?

Andrew: There are two conversations that come to mind. One I alluded to earlier, which is pushing back on partners. Just recently I co-presented at a professional development consortium summer conference. It was a program on helping passive and timid associates learn to push back and manage up. For all the talk about law firms being flat organizations—and it’s true; they do have fewer layers than a lot of business organizations—they’re still pretty hierarchical. Younger attorneys can be overly deferential and very uncomfortable in saying no or pushing back. It can be a lot of different things. I don’t have the bandwidth to handle work, like I mentioned earlier. How do you say that? 

This can especially be a problem if you have one associate who’s getting work from multiple partners. Then it’s like, “Well, I’d like to do your work, but I’m slammed.” That can be a difficult conversation for an associate. In helping them, one learns that they need to do that and it’s O.K. for them to do that. Actually, if they’re just a passive person who’s not providing that information to the people who are giving them work, they’re harming the firm, harming clients potentially, and definitely harming themselves. That is something that’s come up a lot lately, at least enough that the presentation we did this summer was very well received and attended. It’s something that professional development managers and directors in big law are hearing from their associates. That’s one area. 

The second difficult conversation is around feedback. This is difficult in a way because it’s not done enough. Often, in the rush of doing tasks and taking care of client matters, lawyers don’t hit the pause button and spend time with the people who report to them and give them feedback on how they did. I remember this when I was a lawyer. You would finish a transaction. Rarely did we have the time to do a debrief. What worked well? What didn’t? “This was great what you did. It really moved us forward. This is what you could have done differently that would have helped. Next time, maybe you can do it.” Feedback conversations are often missing. 

The other thing in feedback conversations is that they can be very top-down and done with a lack of curiosity about what was going on with the associate. Those conversations can take a more collaborative tone, become more of a dialogue, be less about the problem. “Here’s the problem that came up on this case. We were slow in responding to every filing the opposition brought to us. Let’s get curious about why that happened. What can we, not just associates, but all of us as a team do differently?” Those sorts of conversations. 

The hardest ones, Sharon, are obviously the conversations between partners in terms of strategy, direction, and compensation. Those are given to be difficult, and I do get pulled in to help. I’m a facilitator in those. I don’t have a dog in the fight. I’m just trying to help people understand one another’s perspective. What facts they’re looking at, what their rationale is based on, trying to change it from a legal argument with pros, cons and who’s going to win to more, “Let’s look at the whole business of the law firm. Let’s see what’s good short-term and long-term for all of us, not just part of us.”

Sharon: Each of these are very interesting scenarios. I give you credit for even being able to endure them, especially the first one. Covid probably changed this, but I do remember a partner saying, “What do they think evenings and weekends are for?” I always think of how partners would say, “This guy didn’t make it in terms of client development. It was clear they weren’t going to become a partner. I coached them out.” I always think about, “What did you say? How did you do that?

Andrew: I’m not sure what coaching somebody out necessarily means. Let’s stop here and think about lawyers as coaches. This is one of the things in my first book that I went into in some detail in one of the chapters. The skills for being a good lawyer, when you line them up against being a good coach, there’s not a lot of overlap. Lawyers, to be good managers and leaders, they need to take off their lawyer hat at times. If they’re coaching, which is a very potent, effective way of managing your people, you have to not approach it as lawyers. 

For an example, as lawyers, we often ask closed-ended questions. We’re getting to the facts. In coaching, open-ended questions are much better. You want to see where the conversation is going to go. You want to learn more about what’s going on with the other person. In coaching, you also have to be listening very attentively, not thinking about, “What am I going to say in response to this?” Again, I’m going back to one of the shifts I had to make when I made the transition. As a lawyer, I’m thinking, “This is what I’m hearing from opposition. Now, how am I going to counter that argument? What am I going to say next? How do I want to navigate this conversation?” It’s more oppositional in that way. You really do have to take off the lawyer hat at times to be effective.

Sharon: Your first book, “Lawyers as Managers,” talks about that. Am I remembering that correctly?

Andrew: That’s the second book with Marcia Wasserman. The first one was “The Lawyer’s Guide to Professional Coaching: Leadership, Mentoring, and Effectiveness.” That was, I think, back in 2012. It’s available now. I think you can find used copies on Amazon. The ABA still has it as an e-book. Coaching in the last 10 years has certainly changed within law firms. At the time it was written, it was to help lawyers and firm administrators understand the potential of coaching. I’m happy to say I think that potential is increasingly realized. I wouldn’t say my book is responsible for that solely. Absolutely not, but it was one piece that helped.

In “Lawyers as Managers,” Marcia and I look at the role that lawyers need to take as people managers. Lawyers are generally good managers when it comes to technical aspects. You give a lawyer a spreadsheet, they’re probably pretty good at dealing with it. Things like budgets. When you come to the more interpersonal stuff, like client development, lawyers aren’t as good. When it comes to people management, there really was a lack of understanding. 

Marcia originated the idea. We were at a meeting, and she said, “I’m looking for some materials on leadership and management for lawyers. Do you have any?” I said, “I have a few articles I’ve written for bar associations, but most of the stuff out there is general management and leadership. It’s tailored for the executive committee, the business community.” A couple of months later, we had the same conversation. I said, “Marcia, we’re going to have to write the book,” and she agreed. Little did she know what she was getting herself into. That, I will say, is the definitive book on people management for lawyers.

Sharon: To end, can you tell us about one of the difficult conversations you’ve had? I don’t know how many times I’ve stopped myself and just said, “I can’t do it,” or “I’ll go around it.”

Andrew: I’ll speak in general terms. Again, I’m going back to when I was first making the transition to coaching. I found a great deal of difficulty in having uncomfortable conversations where I had to deliver bad news. I had to tell somebody what they were doing was not working at all. It wasn’t even neutral. It was really harming them and other people. In short, they were really messing up. 

I was very gentle. I was bypassing. I was softening, diluting, sugar-coating messages that needed to be heard. I realized that I was playing nice. I didn’t want to upset the other person. I didn’t want to feel my own upset in doing this, so I wasn’t providing value and the proof that they were making the changes they needed to make. This was maybe in my first two or three years of coaching, and I started to realize this isn’t good. I was stuck and working with my coach at that time. I realized I had to let go of my personal discomfort if I was going to be more helpful to my clients, and I started to make the change.

Now, I am honest. Sometimes people will say, “Can you predict or guarantee any results?” and I go, “No, absolutely not. Coaching at heart is a partnership. We’re working together. I can’t fix you. I can’t wave a magic wand. It’s on both of us. I’m here to help you, but just like I can’t wear your clothes, I can’t do everything for you. We’re going to work together.”

I do make three promises. One, I listen. I listen very attentively to what my coach-ees say and what they’re not saying. The second thing is I am honest. I am very honest. I will not hold back in terms of what I’m hearing or the impact it’s having on me. If a coach-ee is saying something and I’m not believing them, I’ll say that. I need to. If I think something is B.S., it’s the same thing. If I think they’re fooling themselves, same thing. There are times where I have to deliver tough feedback. 

The third promise is I’m compassionate. I don’t beat people up in the process. I won’t sugar-coat, dilute, or bypass. I deliver the message, but I understand they have feelings. In giving them this feedback, it may affect their emotions and their own identity as a person and a professional. I’m aware of it and sensitive to that, but I still get the message across. I figure that in the first two or three years of my coaching, I was sugar-coating. For the last 22 years, I think I have a good record of being straight with people and getting results.

Sharon: Andrew, I’m sure you do get results. Thank you so much for being with us today.

Andrew: It’s been a pleasure. I’ve enjoyed it immensely. Thank you, Sharon.

Related episodes.

LFMC Feature Image 14

Episode 115: Want to Generate Leads? Start Tracking

Episode 115 What you’ll learn in this episode: Why B2B companies are often underserved by traditional marketing companies and strategies What the different parts of the digital marketing funnel are, and how understanding the funnel can help you generate and convert qualified leads Why websites are still a key part of a marketing strategy How […]

Read More →
LFMC Feature Image 15

Episode 114: Forget Your Website Homepage—Google’s Search Results Page Is the New Face of Your Brand

Episode 114 What you’ll learn in this episode: Why Google’s search results page is more important than your website homepage Why the most successful law firms are involved in their marketing, even when they hire an outside agency How a firm’s intake process can make or break their SEO efforts Why content marketing today is […]

Read More →

Episode 113: Succession Planning Doesn’t Have to Be Scary—Here’s What You Need to Know

Episode 113 What you’ll learn in this episode: How to determine what your succession planning goals are Why it’s so difficult to sell a law firm, and which types of practices may sell more easily than others When to start succession planning, and how long to expect a deal to take How buying a firm […]

Read More →

Dominate the Conversation

Arrange a meeting with our team

"*" indicates required fields

This field is for validation purposes and should be left unchanged.