From Black Hawk Pilot to Law Firm Leadership Coach: Ben Grimes' Unconventional Journey

In a recent episode of Innovators Unleashed, I had the pleasure of engaging in a captivating conversation with Ben Grimes, an individual whose journey from being a Black Hawk helicopter pilot to becoming a leadership coach for lawyers and law firms is nothing short of fascinating. Ben shared his unique life story, shedding light on the unconventional path that led him to where he is today.

Ben's incredible journey began with a practical decision to attend West Point, driven by the need to secure a college education. Following his graduation, he embarked on a fulfilling career as a helicopter pilot in the Army. However, as time passed, he realized that his future lay beyond the cockpit and would involve roles that required more than just flying skills.

This realization prompted Ben to attend law school, where he transitioned into becoming a military attorney. Through this transition, he developed essential leadership skills that would serve him well in his future endeavors.

One of the key insights from our conversation was the unique challenge lawyers face when it comes to leadership. Ben eloquently described how the legal profession inadvertently trains its members to focus on individual tasks and billable hours, rather than fostering the collaborative and inclusive leadership skills required in management roles.

To bridge this leadership gap within the legal field, Ben shared his four fundamental pillars of leadership: trust, transparency, empathy, and passion. These principles, he emphasized, are pivotal in creating engaging and inclusive work environments, leading to reduced turnover rates, improved relationships, and enhanced well-being for everyone involved.

We also delved into the intersection of leadership and the pressing topic of diversity, equity, and inclusion (DEI). Ben underscored the crucial role trust, transparency, and empathy play in allowing individuals to bring their authentic selves to work. He explained how these qualities contribute to DEI by reducing the burden of masking one's identity, ultimately resulting in increased engagement and higher performance.

Ben was quick to point out that effective leadership is essential not only in large law firms but also for solo practitioners and small firms. In fact, he argued that smaller organizations may be even more vulnerable to the negative impacts of turnover, making strong leadership an imperative for their success.

We wrapped up our conversation with a discussion of the significant financial implications of turnover in the legal profession, emphasizing the tangible return on investment (ROI) associated with leadership development. This is an often-overlooked aspect due to the misconception of leadership as a soft skill.

I was left deeply impressed by Ben Grimes and the invaluable insights he brought to the table. His expertise in transforming the legal profession through leadership principles and the role they play in fostering diversity, equity, and inclusion left a lasting impact.

Listeners who want to connect with Ben Grimes or explore his leadership coaching services can find him at his website.

Clinton Henry: I'm so excited to talk to you. Your story is fascinating. Can you talk about how you went from being a Black Hawk helicopter pilot to being a leadership coach for lawyers and law firms? That doesn't seem like a normal transition.

Ben Grimes: No. And thanks for that question Clinton. It's not a normal transition. And if it's okay with you, I'm going to back up even a little bit further.

Clinton Henry: Oh yeah.

Ben Grimes: And tell you how I got into the Army in the first place. As you know, I'm a West Point graduate from the mid 90s, so it's been a little while. But my choice to go to West Point was really all about not knowing how to pay for college otherwise. I grew up in small town Pennsylvania. And just didn't know what college looked like. I always expected to go, but didn't know how to pay for it. And so I applied to West Point because it was free and was lucky enough to get in. I was kind of accidentally in the Army in the first place, but graduated from West Point, became a helicopter pilot as you said, and loved it. I loved flying. I loved working with the folks I got to work with. I flew helicopters in Alabama and South Korea and Kentucky, and it was great. But I realized that my future was not going to be flying helicopters and it was going to be some variation of a staff officer pushing paper around, managing other things, but not in the cockpit.

And I said to myself, If I'm going to be a staff officer, I should probably be the [staffiest] staff officer I can. And applied for a program that the Army had to pay for law school. So I went to law school on a whim and that's how I got into the law and spent the balance of my military career then as a military attorney. I still got to do Army stuff, got to lead people, got to grow as a leader, help other people grow. I spent time in Iraq as a lawyer. And when I retired from the Army after 20 years, I spent a few years in federal government and realized I really missed that opportunity to help people grow. And so I started coaching. And that's how I got to where I am now. I just missed that opportunity to help people step into new positions of responsibility. And so I made that opportunity for myself.

Clinton Henry: That's fascinating. So you've obviously specialized on law firms and lawyers, Why is leadership specifically hard for lawyers?

Ben Grimes: Yeah, what I've seen and I'm sure what you've seen in other industries as well, it's not unique to the law, but it really is I think more prevalent in the law in part because of the extra education that's required. And what I mean by all of that is the legal profession trains leadership out of its members because we spend three years at law school doing everything yourself. It's your writing, it's your research, it's your papers, it's your arguments then you join the legal profession. And for the first six, seven, eight years, nine years before you make partner again, it's everything on you. You get assigned a task. And so it's your research, your drafting, and it's all about what you are producing. It's your billable hours. And then when people make partner, all of a sudden there are new responsibilities that go with that that we have never touched before. It's trial team management, it's client engagement teams, it's managing conflict, it's delegation feedback, supervision. It's all of these things that require people to work together that we have effectively trained out of ourselves.

Clinton Henry: So my guess is being in the military helped prepare you for this? It seems there's a lot of tenants and things that you pick up in the military that you wouldn't pick just going right from, let's say, university to law school. What do you typically say when you have a new client who's trying to hone their leadership craft? And they're at a law firm, large or small, What are some typical things advice you give them on where to start?

Ben Grimes: Yeah, you're exactly right. I have had a great advantage in a 20 year military career. And it's a real advantage because not only was I doing leadership daily, I was also trained in leadership at every level. When you advance in the military, there is a school for almost everything. And the military invests in its leaders, which is a great thing. And it's exciting to see more and more private industries and law firms spending the time, the money and the attention to invest in their rising leaders. So I definitely had an advantage coming into law school. And then again, throughout my practicing career as an attorney in the military, I had great advantages of both training and models because all of the folks that were supervising me had been through a system like this where leadership was not just expected but also supported through again training, mentorship and development. So now when I talk to folks, when I get a new client in, one of the first things that we'll talk about is values and what it is that is important to them in their new leadership role. What I've taken from my career is that there are basically four pillars of leadership that will help a leader create collaborative and inclusive teams. Those are trust, transparency, empathy and passion. And when a leader can tap into those things, they're going to be able to be much more effective at creating an engaging environment. So now we're talking about reducing turnover. They're going to create better relationships. So that's useful for the team and for client relations, and they're going to increase everybody's well being to include their own. And so everybody just has a better time at work and it stops being a grunt. It's still hard work, but it's a different kind of hard work and it's less a destroying grind and more an empowering effort that people can put into their work.

Clinton Henry: So you mentioned those four items. Those seem to align a lot with culture so can you talk to me a little bit about what does leadership have to do with culture and does impacting one affect the other?

Ben Grimes:  Yeah. So those four principles, those four pillars that I referred to really are not only the building blocks of individual leadership, but they're also the building blocks of organizational culture. For me, that's law firm culture. So when I consult with a law firm, we talk about not only those four pillars, but again the same way I talk to an individual client, we talk about what the firm's or the organization's values are. Because what I often see is and you see this as well, everybody can see this is a misalignment sometimes between the organizational values on the website. And the policies and practices that are written into the procedures that the organization follows and the actions of leaders at all levels on the ground. And so when you don't have alignment between those espoused values and those practice values reinforced by procedures in the middle, then you're going to have a culture that is non supporting of everybody involved. That's non supporting of its employees. That's going to be non supporting of its clients because they're going to see this mismatch, this incongruency between values and practice. And so when we can focus on trust and transparency, empathy and passion, we really do start to bring those things into alignment. Because in order to work on the trust piece, we have to work on the honesty and communications between espoused values and policies. That's developing and reinforcing trust means creating alignment between those things. And the same is true then working all the way down to individual leader actions on the ground, so to speak.

Clinton Henry: It's interesting. Do you find that the same rules apply for law firms, general counsel offices, non-profits, government legal shops? Do they apply to the same or are you micro calibrating between?

Ben Grimes: I think the principles are the same. What I see are slight differences in the values that different organizations are after or the purposes for which they're working. But I think my perception is that the principles of leadership that influence both organizational culture and individual leadership are the same and it's just a matter of how individual leaders implement those things and how different organizations pursue them from an organizational and cultural level. But I work with law firms and nonprofits and GC shops, everything in the legal sphere from this same lens of these four pillars.

Clinton Henry: Yeah. So we've been in a, I'd say the last five years specifically, but probably more the last three, there's been a large push for diversity, equity, inclusion, belonging.

Ben Grimes: Yeah.

Clinton Henry: In your mind, how does leadership impact DEI?

Ben Grimes: Yeah. I think that there are largely two ways. And I like to put them in the framework of trust and transparency. There's a little bit of empathy as well in terms of understanding, acknowledging and understanding someone else's experience. But for me, it really comes down to trust and transparency. On the transparency piece, I often talk about informational transparency and transparency as individual authenticity. And by being transparent with your team about who you are, what's important to you, and what makes you tick, it makes it more possible. It makes it easier for everybody on your team to bring the same authenticity of themselves to work. What we see in the diversity world and I can speak to this as a black man, minorities and underrepresented folks in the workplace often feel like they have to come to work with a mask on, and that's not limited to minorities. Lots of different folks, for lots of different reasons, feel like they have to come to work with a mask on in some ways.

And that sense of trying to be somebody else is a cognitive load that diminishes engagement, that makes it hard to focus sometimes and can diminish output as well, diminish the quality of the work just because of that extra energy that folks are spending being a little bit somebody different because that's what the environment seems to require. When you take that away, all of a sudden engagement goes up, performance goes up, opportunities for collaboration go up because we know who we're dealing with. And we don't have to work with that cognitive dissonance of monitoring who we're being at work. So that's the transparency piece and by developing trust within the team in a variety of ways, it means that we're able to bring useful and constructive conflict to the office. We're able to question. We're able to offer solutions in ways that we might not otherwise have. We don't really trust that we're going to be heard. And so those two things again, working in conjunction with the empathy piece, I think that trust and transparency really are the keys to increasing diversity, equity, inclusion, access, belonging, all of those things in the office.

Clinton Henry: No, that was great. If I'm an attorney and let's say I just hung up a shingle or I'm a solo practitioner in a small firm, does spending time focusing on leadership matter to me as much as it does to a larger firm?

Ben Grimes: Absolutely. And it maybe even more because there's nobody else to spread the load to. But leadership is going to matter at every level from solos to big firms. And at the solo, the small firm level, just because it's you on the shingle doesn't mean you're the only person that you're dealing with. Leadership is any time folks come in contact with each other. So a solo attorney who's managing a paralegal and a secretary, we're just one person managing a VA, a virtual assistant. A solo attorney who's doing client engagement, that is leadership, being able to talk to a prospective client or a current client and walk them through what the engagement is going to look like, what their options are. Client advice is leadership. And the more that folks recognize that that's the case, the more effective they're going to be in providing that advice.

Clinton Henry: That's really, really intelligent. I would also argue that because you are a small firm, turnover impacts you more negatively, right?

Ben Grimes: Oh, yeah.

Clinton Henry:  And so making sure that the people that are on your team are engaged and view you as a strong leader and somebody they want to work with is critical because you're not a big firm where they can just slide somebody else in like that could really, really have a negative impact probably larger than [overlap].

Ben Grimes: For sure. I mean, turnover is the scourge of the legal profession right now. It seems hard to keep people in place even at big firms. But you're absolutely right at small firms. I saw a study that talked about the profit impact of turnover. And basically, depending on how big your firm is and what billing rate your attorneys are billed out at and how much you pay them. The cost of not having somebody in the seat can be anywhere from $60,000 to over $200,000 per month in profit. And so when you're looking at a solo, who takes on one associate let's say, that one associate might be adding an extra $50,000 in profit, small firm, not paying them a huge amount, but paying them well. Not billing them out at a crazy amount, but billing at a reasonable amount. But that might be $50,000 in profit that a solo or small firm is losing every month. There's a vacancy and that doesn't account for the hiring and onboarding costs, doesn't account for the shifted work that everybody else has to do now and then for bigger firms that are billing at a higher amount and paying at a higher amount, that profit loss might be over $200,000 per month, per employee vacancy, per attorney vacancy. And so there are real incentives to real ROI and incentives to investing in leadership that many people overlook just because they feel like it's a soft skill.

Clinton Henry: Yeah, completely agree. I think sometimes you'll miss that mark. And then at the end of the year they look at there and they're like, What happened?

Ben Grimes:  And they wonder why. Yeah.

Clinton Henry: Exactly. Yeah. Well Ben, thank you so much. I really appreciate the time. This was very insightful. I got a lot out of it. I know our listeners did. So how to contact you will be in the show notes, but thank you again for the time. Really appreciate it.

Ben Grimes: Yeah, no, I really enjoyed the conversation. Thanks a lot.