Leadership In Law Podcast

S02E57 Lessons in Leadership and Firm Growth with Ross Pitcoff

• Marilyn Jenkins • Season 2 • Episode 57

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Ross Pitcoff has built something remarkable - transforming his solo law practice into the 11th fastest growing small law firm in America. How did he do it? The managing partner of Pitcoff Law Group shares his extraordinary journey with both candor and wisdom.

"Operating a business internally is very different than looking externally," Ross explains, likening leadership to conducting an orchestra. "It's about figuring out where everybody's supposed to sit, getting the right people in the right seats, and making sure everybody stays in tune." This orchestral approach has proven remarkably effective, enabling his firm to grow from zero employees to a team of 15 professionals across three states in just a few years.

What sets Ross apart is his commitment to personal growth as the foundation for professional success. He overcame imposter syndrome through disciplined morning routines, clear goal-setting, and visualization - practices he continues today. His leadership philosophy combines stoic principles with modern business strategies, relying heavily on fractional C-suite advisors who specialize in law firm growth. "We want to stand on the shoulders of giants," he says, emphasizing how crucial expert guidance has been to their meteoric rise.

Perhaps most refreshing is Pitcoff's egalitarian approach. Rejecting rigid hierarchies he witnessed at previous firms, he has cultivated a culture where every team member is valued equally regardless of role. This horizontal leadership model, combined with a virtual operating structure, challenges traditional assumptions about how law firms must function. His ultimate advice? "Be kind. If you want to be a leader, learn to be kind first." This deceptively simple philosophy, paired with the courage to have difficult conversations, forms the foundation of his remarkable success.

Reach Ross here: 

www.pitcofflawgroup.com
https://facebook.com/pitcofflawgroup
https://linktr.ee/pitcofflawgroup

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Speaker 1:

Welcome to the Leadership in Law podcast with host Marilyn Jenkins. Cut through the noise, get actionable insights and inspiring stories delivered straight to your ears your ultimate podcast for navigating the ever-changing world of law firm ownership. In each episode, we dive deep into the critical topics that matter most to you, from unlocking explosive growth to building a thriving team. We connect you with successful firm leaders and industry experts who share their proven strategies and hard-won wisdom. So, whether you're a seasoned leader or just starting your journey as a law firm owner, the Leadership in Law podcast is here to equip you with the knowledge and tools you need to build a successful and fulfilling legal practice.

Speaker 2:

Welcome to another episode of the Leadership in Law podcast. I'm your host, marilyn Jenkins. Please join me in welcoming my guest, ross Pitkoff, to the show today. As the managing partner at Pitkoff Law Group, mr Pitkoff has spearheaded the firm's recent tremendous growth, earning the firm the prestigious Law Firm 500 Award in 2023, while officially ranking as the 11th fastest growing small law firm in the country. This notable achievement is a testament to Mr Pitkoff's exceptional leadership, commitment to excellence and passion for delivering exceptional legal services to his clients. In addition to his legal practice, he is a highly sought-after speaker, sharing his insights and expertise on topics related to commercial business practices an alternative, if I can speak today dispute resolution. Welcome to the show, ross. I'm happy to have you here today.

Speaker 3:

Likewise, and thank you very much. It's very nice to be here.

Speaker 2:

Absolutely so. Tell us a little bit about the beginnings of your leadership journey, how you got started.

Speaker 3:

Sure. So I opened this law firm in about 2018, and at the time I was a solo practitioner, so I was working on my own and it was really. I started to see results working with various clients, and I was able to get better and better results as time went on and in around 2021, we felt the need to start to enlarge our staff a little bit, but really our first W-2 attorney came on in 2022. Since that time we've grown to a team of 15, so we've certainly seen rapid growth.

Speaker 3:

But the way leadership plays a role is to sort of recognize that operating a business internally looking internally is very different than looking out externally. Externally, you're working with the clients, You're looking to get those results, You're going to court, You're negotiating, You're fighting for the rights of the clients. Internally, it's almost like an orchestra. It's about kind of figuring out where everybody's supposed to sit, getting the right people in the right seats and making sure that everybody stays in tune, Because if we're not in tune, if one piece of that puzzle is sort of off, or one piece, whether it's the violin or the cello something doesn't quite sound right, then the rest of the orchestra will suffer as well. So our team is very big on working together, we're very big on collaborating and we're also very big on making sure that we're all headed in the same direction.

Speaker 2:

I love that. I love the way you put it as an orchestra, because looking inside is completely different. Sounds like you use the EOS different. It sounds like you use the EOS system.

Speaker 3:

It's funny enough. I'm very familiar with EOS and I'm familiar with Gina Wickman. I'm also familiar with Scaling Up, which I believe is Vance Harnish, but we do not officially use EOS in our firm. I think that we take many of those ideas and many of those concepts and we apply them, but EOS is something that you know we've discussed fully implementing, but we have not done that yet.

Speaker 2:

Well, it sounds like you're doing a great job as far as with your growth. So let's talk about you know looking up and hiring coaches. So can you explain how hiring coaches helped you to grow your firm and kind of keep your eye on the ball of what you're looking for?

Speaker 3:

Sure, well, I fully and wholly believe that people who wish to advance only do so by either going through an experience on their own and or learning from other people's mistakes that came before them, and so, for us, hiring a coach was a very easy decision because we, as many before me were able to do.

Speaker 3:

We want to stand on the shoulders of giants, and when you read through history and you read through various people that have accomplished great things, all of them had a mentor, and whether you have mentors that are alive or whether you have mentors from books that you're reading from 100, 200, 300 years ago, it really makes no difference. So I would say, our first coaches for me it was the Stoics and Marcus Aurelius and really beginning to take on those lessons. Of course, that was those weren't in-person meetings we had, but when we really got serious about the firm and it was really for me late in 2022, I said I needed to make a change, and so I found coaches that were familiar with not only just business growth, but law firm growth. So we use a series of fractional advisors. We have a fractional CEO, a fractional CFO, a fractional COO and now a fractional CMO. So we're really we're beyond and through the roof. However, without that guidance and without those directives and the processes that we've taken from those fractional guidance C-suites, we wouldn't be where we are today.

Speaker 2:

And that's pretty impressive 11th fastest growing law firm in 2023 that in the country. So that is impressive that you've been able to make that decision in 2022 and see that growth in the 2023 and beyond.

Speaker 3:

That's pretty impressive and I expect that we'll have the same. We will be an award recipient this year as well, so we're looking forward for 2024. So we're looking forward for 2024. So we're looking forward to that, but I appreciate that. Thank you Absolutely.

Speaker 2:

Absolutely. So, looking at, obviously, as you're bringing people in the right butts, in the right seats and everybody on the same page, what values and principles are you bringing, like maybe your mission statement to help keep everyone on the same page and that guide you as a leader?

Speaker 3:

Sure. So we do have more so than just the mission statement. We do have our core values, and we actually make sure to have the core values posted on our website. So we invite everybody that applies for a role with our firm to really get to know us, to learn a little bit about us.

Speaker 3:

I think one striking component of what we look for are people who not only have a passion for justice, who do want to fight for those that have been wronged, but are also able, capable and wanting to express a level of emotional equanimity goes back to the stoics, you know, the steady hand but it is tremendously important for people in our profession, especially in the commercial space, where it can be very volatile dealing with third parties, dealing with other attorneys, going to court and having, you know, disputes that are based on a lot of anger I mean, there's certainly legal implications, but there's always a lot of anger to be able to sort of absorb the energies of the clients and then to be able to keep the peace, keep things calm, assuage the client, hold their hand through this process and then also, with professionalism and with strength and toughness, be able to convey something to the alternative side. So when we're interviewing and when people especially on the production side attorneys and paralegals are looking to join the firm. Those are some of the things that we're interested in learning about, and we explain that. That that's what we're looking for here.

Speaker 3:

As for the rest of the team, I think it's very much oriented with the same mentality. Are you growth minded? Do you also believe in these values? Do you believe in justice? Do you seek to have that kind of equanimity in an institution that you work for, even if you're not the ones dealing externally?

Speaker 2:

Because those values that we espouse externally we also utilize internally, so we're constantly ensuring that the people that are joining us are aware of this. Fantastic, fantastic, and do you with your fast growth and how do you, or have you, dealt with imposter syndrome Going from for people look at 2018 to now? That's a pretty amazing growth pattern. How have you?

Speaker 3:

dealt with self-doubt, fear and imposter syndrome throughout. That? That's a great question, I think. Ultimately, for me it came through a morning routine, but it's really all in the mind. It's all mindset. It's ensuring that one has a goal. It's ensuring that one has a vision of what that goal looks like, and then it's reverse engineering and writing it down and I think the you know the idea of the imposter syndrome or I don't belong here, what am I doing here?

Speaker 3:

That is something that you can take because that's really a belief and I firmly believe that we as creators can change our beliefs at any time. So I would say, maybe early on. I know, you know we, between the end of 2022, when we first hired to now, we've gone from what? Zero, full time to 15. There may have been some of those concerns and fears, but once you you create that goal, you have your vision, you start to reverse engineer how you can get there and you believe it I mean really believe that it's doable then a lot of those fears get kind of tossed to the side and by staying focused on that goal, the day-to-day concerns and the day-to-day angst that can absorb a lot of people and derail them, it doesn't mean we don't experience it, but we're able to push through it. So that has really helped in our growth no-transcript.

Speaker 2:

So that's fantastic. There's sometimes moving from being a solo attorney to a person, a people manager, into management, into a leader. That becomes things a difficult transition. What helped inspire you Like, do you have a podcast you listen to? Obviously your coaches to kind of keep your eye on the ball and your obviously your morning routines to keep you moving forward as a leader.

Speaker 3:

Sure, Well, it was significant change and shift, but I had gotten to the point where I felt that the firm, the institution, had grown larger than just and I could no longer manage it on my own. And that's when you really need to make a choice, you know. Do you want to stay at a certain point, which is OK for those that do, or do you see something bigger For me? I saw something bigger and larger and greater. I also just felt that I've always had a good intuitive ability to communicate effectively. I've always had a good intuitive ability to communicate effectively. So the thought to me of taking the skill set that I utilize to get results for clients to then try and build. I felt that I had the first necessary layer, which arguably is the hardest one to teach, and that is to know how to be able to communicate effectively. Beyond that, certainly, I'm a member of a group called how to Manage a Small Law Firm that has been instrumental. It's run by a man by the name Archon Robbins Sounds like you might be familiar.

Speaker 3:

I also listen to an individual by the name of David Nagel Dally. He's all you know, speaking on mindset and growth, and so I think, between getting the advice coming from some of those that you work with, getting the Dally mindset you know, which is not only motivational but you really change yourself, because personal development precedes professional development. I think it's very true. So, in any field, anybody that's able to accomplish and to believe that they're worth what they're accomplishing not everybody's born with that, but you can change at any time, which is so exciting. So I think it's. I think staying on track is ensuring that I continue to work with those that are there to help. The help is everywhere, If you just go out and find it. Combined with ensuring that, you know mindset is a continuous part of the daily practice. There's nothing to stop us.

Speaker 2:

Fantastic. Now I know that you have three locations and they're not super close together, so how do you keep the whole team on the same page as far as where you are growth-wise, goal-wise, customer service-wise? Do you have weekly meetings? Do you have layered meetings, you know like broken down into pods, that sort of thing? How does your communication structure look? What does your communication structure look like?

Speaker 3:

Sure, that's a great question. We do operate predominantly virtually in all three states. So for us we utilize Microsoft Teams and we're very active. So people are interacting daily. We do have different pods. We have a sales department, we have the production, the legal team, the attorneys, we have partners, we have paralegals, we have legal assistants, and so there's meetings constantly taking place and then Fridays the full team gathers and meets together and we'll talk about something of value and imports and then the rest of the team drops off while the production team sort of goes through the full case list, more so in touch than a team that every day is fully together in one office location. So we've managed to sort of shatter any kind of limiting thoughts or beliefs that you can't really operate in a virtual setting across different states. It's very doable and we ensure that we do things well and we do ensure we make time for in-person sessions as well.

Speaker 2:

Wow, that's very good, because that's always one of the things is okay. I meant just too much meetings, but I think the pod structure and for anybody who's listening that don't get that is we experience some clients and I've got some people I network with that they have a certain number of clients and literally a full structure for every 20 clients or every you know that sort of thing. So you can break down into the ideas or the specialties and that would be one reporting structure to get all the communication together. So that sounds very interesting that you're doing that and it's very effective across very state lines, different state lines.

Speaker 3:

I think it is. And then, of course, it's important that there are agendas for the meetings and that those agendas tie into ultimate keep the firm syndicators, which the firm does keep track of. So if everybody knows and partake in what they, you know what we want to accomplish as the collective, it affords the people running the meetings to make those meetings as efficient as possible, because you're always gravitating towards something which all comes back to the idea of having goals. I think one potential mistake organizations can make, especially at a smaller level, is having tons and tons of meetings but really lacking direction and efficiency. And you know things, wheels start to spin and what initially was even going to be spoken about is not talked about at all or it's kind of tossed to the side and then progress is not made. So it's ultimately also so important to have an agenda which is tied to key performance indicators.

Speaker 2:

That is a good, very, very good point, very good point. So, with your growth and with going from one employee to 15, how do you handle your work-life balance? Do you have hobbies? Do you have you know what? What? How do you handle it?

Speaker 3:

That's a good question. I think there was a time where, you know, in each iteration of growth and change, I find that I wind up changing myself, and that's a very important component of any entrepreneur. In a business that's growing, you sort of have to keep reinventing yourself to accept, you know, jumping all in to the new 20% that's going to get you 80% of the results, and so early on in a change there is a lot of work. But I find that for me it's waking up early, getting to the gym, doing my affirming and visualizing in the am and as we've sort of grown, I've managed to delegate more and more work. And the more I'm able to delegate to people that are a part of our process, who understand our goals, who want to be a part of that collective success, it actually gets easier.

Speaker 3:

And so you know you hear people talk about, you know you think well, you got to it's going to get harder and harder and harder. The more you grow, the harder it gets. That's not really so true. We're finding that the more organized you get, the more policies and procedures that are finished, the more people that are sitting in the right seats, getting great people that are a part of this exciting organization. You become more in harmony, you're more in tune as a whole, and as that orchestra grows, so long as we're all headed in the same direction, it's not necessarily so much harder. It's just the only thing that one might feel is the recognition of responsibility. But with great things come great responsibilities, so we're okay with that.

Speaker 2:

Well said. Yeah, absolutely. I love the way you phrased that. So, thinking about what you did, building the Legal Empire at 39, what lessons in leadership and ambition did you learn?

Speaker 3:

It's a great question. I think the biggest thing about being a leader is being able to recognize that number one. You never know what's going on in somebody's head, in somebody else's head. You always want to ensure that you're mindful that everybody's a human being, no matter what role they're in, whether they're an administrative assistant, a receptionist, a legal assistant, a attorney, a partner. We're all humans. So I think, as a leader, it's imperative to treat everybody equally and that's what we do here.

Speaker 3:

I can recall personal experiences of being at other law firms where, you know, frankly, there was a very clear hierarchy and, if you know, there was even, you know, in the past. I remember being somewhere where all the attorneys for lunch would sit on one side and the rest of the staff was somewhere else, and we're this clear sort of distinction and it always bothered me internally. I thought that just doesn't feel right. So I think that's the biggest thing that I've tried to bring to this institution is we're again, we're all part of the collective. We're all here together. Each of us plays a role that leads towards the better whole. So that certainly has been the most important, I think, portion of leadership that I've taken to heart, and you might have had another portion to that question, but I think it's slipped my mind.

Speaker 2:

No, that's that. I'm going to move on to saying asking a question just after that. How do you instill your leadership goals or your leadership strategy I'm not sure what word I want to use there To the people beneath you, right, and I don't mean it beneath you, but, you know, to your team, because eventually, as you continue to grow, your leadership skills are going to be different. You're going to be in a different position. You're going to need those people to take over more of the leadership roles. How are you delegating that down?

Speaker 3:

Well, and that's a great question as well, it's number one. It's a consistent reminder of our core values. If we all act in accordance with the core values that we espouse, then there's going to be alignment with the leadership style that I just referenced. And as we continue to grow, more and more people will fill seats where they will have more and more authority over a growing number of individuals. And so, to your point, you know, with respect to partners of the firm, and how are they dealing in their pods with their paralegals and legal assistants?

Speaker 3:

The idea is that you know, they know the way we're supposed to be leading, they're fed information about the way that we want to focus on our core values, and we expect that they'll continue to operate in a similar way. And if they didn't, then there'd be a frank conversation. So the short answer to that question is how do we sort of keep everyone aligned? It's like this it's having just very open and direct and frank conversations. And the last piece of this is I think you can be very direct but be kind. You can be strong but you can be decent, and that's something that we utilize internally and that's, frankly, the way we also act externally when dealing with opposing counsel on behalf of our clients.

Speaker 2:

I love that. So, basically, having your core values and everyone is bought into your core values and goals, is there looking back at your journey and people who might be listening? What would you would like them to have their biggest takeaway from this?

Speaker 3:

You know it sounds cliche, but number one is be kind. It's really be kind If you want to be a leader, if you have the excitement and the motivation and the ambition to lead a team. Number one is that you need to learn to be kind. And then, if you already have the kindness gene and you're not concerned about that, then it is finding the strength and the will to have hard conversations. So you need to learn to get comfortable being uncomfortable. But if you can take kindness, you can take directness and you're able to iterate and explain and communicate with people in a way that makes sense, so provide clarity to them. Those are the necessary and important ingredients to having a successful leadership model.

Speaker 2:

I love that. That's great. That's fantastic, and I know that the audience is probably going to want to reach out to you, connect with you, just to you know, see where you're at and where you're going. Where would be the best place for them to connect with you?

Speaker 3:

Sure, so we're all over social media, for better or for worse. Our website is pitcofflawgroupcom, that's P-I-T-C-O-F-F lawgroupcom. My email is ross at pitcofflawgroup and our number is 646-386-0990.

Speaker 2:

Fantastic. I'll make sure that all that's in the show notes and this has been a great conversation. I really appreciate you taking the time to join us here and talk about your leadership journey.

Speaker 3:

Thank you so much for having me.

Speaker 2:

Thanks for joining me today for this episode. As we wrap up, I'd love for you to do two things. First, subscribe to this podcast so you don't miss an episode, and if you find value here, I'd love it if you would rate it and review it. That really does make a difference in helping other people to discover this podcast. Second, you can connect with me on LinkedIn to keep up with what I'm currently learning and thinking about. And if you're ready to take the next step with a digital strategist to help you grow your law firm, I'd be honored to help you. Just go to lawmarketingzonecom to book a call with me. Stay tuned for our next episode next week. Until then, as always, thanks for listening to Leadership in Law podcast and be sure to subscribe wherever you listen to podcasts so you don't miss the next episode journey.

Speaker 1:

There's a whole community of law firm owners out there facing similar challenges and striving for the same success. Head over to our website at lawmarketingzonecom. From there, connect with other listeners, access valuable resources and stay up to date on the latest episodes. Don't forget to subscribe and leave us a review on your favorite podcast platform. Until next time, keep leading with vision and keep growing your firm.

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Marilyn Jenkins

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