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Kim Meninger

What the U.S. Military Can Teach Us about Leadership

Updated: Oct 20, 2023


What the U.S. Military Can Teach Us about Leadership

In this episode of the Impostor Syndrome Files, we talk about what the US military can teach us about leadership. If you’re like me and have limited experience with the military, your perceptions are likely based on what you see in the movies. But there is a lot we can learn from the military’s approach to leadership. My guest this week, Ben Grimes, is a former U.S. Army helicopter pilot and military attorney who now coaches and consults with lawyers, law firms and other organizations to improve their cultures and performance levels. Here we talk about the importance of trust and empathy to human-centered leadership.

About My Guest

Ben is a leadership coach and consultant who brings decades of leadership training and development experience. From his twenty-year career as U.S. Army helicopter pilot and military attorney to years as a federal government leader and recognized professionalism expert, Ben is a resource to lawyers, law firms, and other professionals working to shift performance and culture. With a focus on developing leaders grounded in principles of trust, transparency, empathy, and passion, Ben facilitates growth in personal capacity, organizational health, and enterprise success. Ben is, himself, passionate about the power and potential of leadership with a human lens. He holds a B.S. from the United States Military Academy at West Point and a law degree from New York University School of Law.


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Transcript


Kim Meninger

Welcome, Ben, it is such a pleasure to have you here today. And I'd love to start by inviting you to tell us a little bit about yourself.


Ben Grimes

Thank you, Kim. I'm really excited to be here. I am a Ben Grimes. I am a leadership coach working primarily with lawyers. But I work with lots of other professionals in a variety of industries, primarily with folks who are stepping into new roles of responsibility. So getting ready for new partnership in a law firm, for instance, or folks stepping into new positions as the chief of HR or the General Counsel, in, in, in house setting. But folks stepping into new positions of authority and responsibility. I like to help them kind of refine their leadership and, and step out of that impostor feeling as they're stepping into these new roles.


Kim Meninger

And what's your background? How did you end up with this focus area?


Ben Grimes

I grew up professionally in the army. So I went to West Point as an undergrad, and graduated from there went off first to be a helicopter pilot and spent about four years flying Blackhawk helicopters in the army, which is where I first maybe not, not even then first, but when I really that imposter syndrome really setting in a professional setting. And then after flying for a few years, I got into a program that the Army has that pays for law school and went to law school on the Army's dime, returned back to the field as a military attorney, but then spent a 20-year career finished, finished my 20-year career in the army, as a military attorney, doing prosecution and defense and teaching at the graduate level, and got into ethics and professionalism. And when I when I retired from the army, went to the Department of Justice for a little while doing Ethics and Professionalism work, and just realized that the principles that guide leaders in the army, what, what they refer to as Officer ship principles are really useful guides to leadership generally. And I wanted to see more people take that up and kind of embrace those principles of taking care of other people. And so I launched this coaching business focused primarily on lawyers, because I know lawyers best to make the practice of law a more humane place for everybody to be in.


Kim Meninger

I love that I have so many follow-up questions on that front. But I gotta go back because I don't talk to a lot of Black Hawk helicopter pilots. So I want to talk to you about really connecting with impostor syndrome at that point, what was it like for you to do that? And what would it, did it trigger within you?


Ben Grimes

So number one, flying helicopters is a lot of fun. That's probably not a great surprise. There's a lot of work that goes into it as well, there's a lot of preparation, a lot of making sure the helicopter is in good shape and flight planning and things like that. And but as a young officers, so I graduated from West Point, went to flight school, and then went out to the field as a platoon leader responsible for about 30 Folks, and three or four helicopters. And when you go out in a position like that, you are one of the most senior folks in terms of authority, but one of the most junior folks in terms of experience, and being in a leadership and in a thought in a position of authority and a position of responsibility, and not knowing what you're doing. I mean, that is that sets up all kinds of feelings about not being ready, not being competent, not knowing not knowing that any, if anybody's going to trust you, not knowing how to make decisions, when, when Prop challenges come up to you. It's, it can be very, very challenging. And then you layer on top of that a million dollar aircraft and people's lives on the line and you're, you're picking up cargo or you're picking up troops or you're ferrying VIPs back and forth. There's a lot at stake. And mind you, for me, this was pre-911. So we're not a lot of combat flight time, but, but there's still a lot at stake. And for young officers for young leaders in the military post 911 Obviously the stakes are even higher. So for me, that's how I that's that was the professional my professional start as a leader in terms of imposter syndrome and feeling not quite ready. Perhaps I can go back even further. We're back to my arrival at West Point. It's a pretty competitive school to get into. And, you know, the folks who are listening can't, can't tell. I'm a, I'm a black man, right? And there is, for anybody who is in a marginalized community, you know that just being who you are, in some of these settings, induces a sense of imposter syndrome induces a sense of not being enough, even if you've taken all the tests and all the classes and performed and all the ways that everybody else is performing, there's still a sense that you're not that other people don't, don't see you as good enough. And that that gets internalized. That's a hard thing to deal with. And for me, it was particularly tough during my time at West Point, because I did screw up. I did, I lied, I got suspended for a semester, which was a really big deal then. And during that time away, I got, I got sent back home for a semester. And while I was home, somebody in the community, I got a part-time job and somebody in the community said to me at one point, Ben, you really disappointed all of us. And that really hurt. And it really impacted the way I saw myself and whether, whether or not I believed I was good enough to go back to West Point and Excel. And I did, I went back, I was a division one athlete, I graduated in the top 60 In my class, and went off and had a 20-year career in the army. I did really, really well after that. But those seeds of doubt were planted pretty early.


Kim Meninger

And you're in your story, you have touched upon so many of the different triggers of self-doubt and impostor syndrome, right? You know, feeling different from the majority culture being in a situation where you have authority, but not a whole lot of experience. I'm imagining, to and curious to get your perspective on this, because you use the term humane when you were talking about working with lawyers. I think those of us who have not been inside the military have, you know certain perceptions of what it's like there? Would you call it a humane place? And I wonder, Is it okay to ask for help? Like, how do you navigate self-doubt in that kind of an environment?


Ben Grimes

I think that's a great question. And different folks will have different answers to it. My answer based on my experience, is that it is a surprisingly humane environment. The reason I lead the way that I do, and the focus that I bring to my clients, the folks that I bring to the focus that I bring to my clients is really grounded in the leadership that I learned and experienced while I was in the army. And the pillars of that experience are trust, transparency, empathy, and passion. And it is often surprising for folks to hear that my experience of military leadership included empathy, compassion, trust, transparency, but it those really were the hallmarks of the great leaders that I worked for. And they were a great model for me to, to emulate as I was growing up. And those are, those are the qualities that I tried to bring to my teams. So yeah, it was a humane environment. It's not, it's certainly I would be remiss in suggesting that it's always okay to ask for help. Not I'm sorry, that it always feels like it's okay to ask for help. Sometimes it doesn't. But the perhaps counterintuitive nature of military life is that everybody really is there to support each other and to reinforce each other. And asking for help may be difficult because there's an expectation that we're all going to perform at the highest level. So it may be difficult, but those requests are really, they fall on open ears. And they, those requests are received generously whenever they're made.


Kim Meninger

And it's got to be so important, given the stakes that you've described, that people be able to access support, because it's not just the possibility of making a simple mistake in the workplace, the average workplace, right? You're talking about people's lives and you talk about, you know, equipment and things like that. So, so do you feel like and I'll take a step back here because when I Think about the workplace, we often, we often think about sort of old fashioned for lack of a better term leadership is command and control. And we're trying to move away from that. But of course, I think command and control is the military model originally, right? So. So when you think about creating enough psychological safety for people to be able to ask for help, or to get the support that they need, it certainly maps to the values that you talked about in terms of the leaders that you admired as a cultural thing. Do you feel like there's psychological safety and…


Ben Grimes

In the military writ large?


Kim Meninger

Yeah, we don't just wonder how do you get people to when imposter syndrome is likely to show up in any environment, but particularly given the conditions that you're describing, it's that much harder that people feel a sense of psychological safety. And I can imagine how, just again, as an outsider who has just only TV and movie references to fall back on when it comes to the military, it just, it seems like it could be a very intimidating place to get the kind of support that you need to feel more confident in your environment.


Ben Grimes

I think it's intimidating in the sense that the quality of leadership and the quality of performance, broadly is very high. And that can be intimidating. That can be I mean, that's, that's a piece of the impostor syndrome, by itself being in an environment of great performers. And so that can be intimidating. But while there is a place for command and control leadership, and certainly in the military, there's a place for command and control leadership, there's a place for that in, in lots of different settings. But in order to make command and control leadership, really work, it has to be built on a foundation of trust. And that, that's a lot harder to, to kind of present in a movie or in TV, like creating an environment of trust is not, you know, you don't get Ernie Pyle yelling at somebody in the barracks, you know, that's not, it's, that's not nearly as entertaining. But and so because of that, you know, command and control leadership is, is very associated with the military. But in reality, leaders, even in the military, who rely on command authority are generally not the ones who are successful. You really succeed as a leader, even in the military, by teaching, by empowering, by caring for the folks that you're responsible for. Because when you get into a situation, where command authority is necessary, where it's just do what I say, because you, because I said it right now, when you get in that situation, the only reason that really works is if the folks who are taking the orders of receiving those orders, trust in the quality and the and the good intentions of the leader who's giving them.


Kim Meninger

That makes so much sense. And you're right, that there's a time and a place for command and control leadership in every situation, I think of it as in parenting as well.


Ben Grimes

That's exactly right.


Kim Meninger

So what can we learn from the military? Like what are, where is the military further ahead of us in the sort of private sector that you should think about it?


Ben Grimes

I think the place that the military excels, it is really in leadership development. Every almost every rank that I attained in the army was preceded by a leadership course of some sort. So every time I grew in responsibility, I was Empower, I was empowered with more skills and more resources and more knowledge in order to be effective at that higher level. That doesn't mean that it always went smoothly, it doesn't mean that I didn't suffer impostor syndrome along at every step along the way, in some in some instances. But it does mean that the organization was committed to helping me grow in order for the organization itself to be successful. And I think that's where the private sector, even civilian government falls behind in that we, by and large, don't invest that much in helping people get ready for the next step or step into the next position of responsibility, through courses through mentorship through coaching, and all of these things are useful in varying capacity like in varying doses. But, but we very rarely do it, you know, the good sales rep gets promoted to managing the sales team because are great at sales, not because they're great at managing. And the same thing is true in law firms that I work with, you know, folks are promoted to partner because they've shown excellent research writing skills, but not, but not demonstrated any particular skills in managing a trial team or engaging in a client interaction. And all of those things will be will be part of their new responsibility said, once they get promoted, but it's not something that they're generally prepared for. And you see this. And we've all seen this, as we, as we've grown up in, in our own professional lives.


Kim Meninger

Oh, he makes such a fantastic point. And it just reinforces why there's so much pervasive self-doubt out there, right? Because you're absolutely right, we sort of take for granted that, because you're a great domain expert, that you're going to come with all of the requisite leadership skills and want to do it. Right. Yes. Right. motivated to want to do the kinds of things that leaders need to do that take you away from that core competency, that maybe this what you'd rather focus on. And so it's, it's no wonder that people struggle so much in making the kinds of transitions that you're talking about?


Ben Grimes

Yeah, because in almost every instance, the core competency is not the core competency as the manager, it is a completely different skill set. And the fact that you understand the core competency is a plus, but it's almost not required at all, in order to manage the team.


Kim Meninger

Absolutely. And so I'm curious, what kinds of things do your clients tell you about what are they bringing to you as challenges or things that they want to work on with you?


Ben Grimes

It is probably the same sort that the same sort of issues that folks everywhere dealing with it is I'm stepping into this new role. I'm now responsible for this team, a larger team, a new team. And I need to I want to be more comfortable with delegation with giving feedback with time management, with the appropriate balance of empowering folks, but also taking, you know, keeping my hands on the reins and depend depending on the ability to get a 360 some 360 feedback, sometimes it'll be well, let's also work on your micromanagement. It's not just that, you know, you're not empowering folks. But it's also let's talk about micromanagement and, and how to step away from that. But in all of those instances, feedback, delegation, time management, all time management, less so. But anytime you're dealing with other people, for me, it comes down to the, the roots of trust and transparency, and empathy, and how are we communicating with folks? To what degree do we care about the folks that we're responsible to? And how do we demonstrate how do we develop and demonstrate trust and transparency with them? And what I like to say is, when it comes to trust, you can want people to trust you. But you can't make them trust you. And trust really is a two-way street. And when we're talking about a two-way, a two-way relationship, it is imperative that the leader go first you have to give trust to your team before you can expect them to trust you.


Kim Meninger

Hmm, I think that's a really good point. And I think that ties back to what you were saying about micromanagement too, because I think of micromanagement is often a reflection of the fact that these managers are not adequately prepared for these new roles. And they're so afraid of getting it wrong, that it puts them in a position where they feel like they have to be involved in everything, right, either because that's what got them to where they are in the first place. It's the kind of work that they know how to do and feel more comfortable in that space, or because they're so afraid that they're gonna miss something that they're constantly checking up there, you know, just want their fingers in everything. And so as counterintuitive as it probably sounds, to give trust in order to build the trust that you're going to need to lead them later. Right. It actually is a very good way of leading.


Ben Grimes

Yeah, and it's, it's not easy all the time, it can be challenging. It can be challenging, and those are those are some of the questions that I, that I work with my clients on.


Kim Meninger

Now without giving away your secret sauce. Are there specific things that you start with? Like are there certain universal kinds of tips that you give to people or things that you think anyone who's listening and sees themselves in this conversation should think about


Ben Grimes

Yes, I think and it's, it's not secret sauce, but, but for me, it starts with values. And I like to think about organizational values. And I want my clients to also drill down on their own values, how do they see the world in pretty granular detail, because those values are going to inform how we make decisions, how we talk to folks. And, you know, people don't have to assume the same values that I carry, but, but understanding your individual values is going to make it easier, easier for you to have conversations and to communicate in a way that makes sense to you, that's part of the transparency piece that I think is very important, it's understanding who you are. So that you can be you can actually be that person with your team, that and, you know, transparency and authenticity work is not necessarily like showing your kids pictures all over the place and, and talking about what you, you know, what you had for breakfast, if that's you, that's you, but that doesn't have to be that doesn't, that's not a requisite for Authenticity. Authenticity is really understanding your values and what makes you tick, and then not being and then understanding how to bring that to work. And for again, to go back to the, the my comment about marginalized identities. You know, wearing a mask at work is tiring. Wearing a mask at work is part of the impostor syndrome, feeling part of the feeling of being separate. And once we understand our individual values, and can feel firm in them, it becomes a lot easier to take that mask off and be who we are, and step into kind of step into our personal authority to, to really engage with our co-workers from that position of strength in the knowledge of who we are.


Kim Meninger

Yes, and I'm so glad you tied that to the experience of being part of our marginalized group because one of the things that I think about a lot is that we all you know, talk about the benefits of diversity. But then once you get into an organization, the implicit or the explicit messages, you need to conform to the norm. And so when you're in the situation where you have a different life, experience, different viewpoint, whatever is different about you, there's this sense that there's something wrong with me, or I need to hide that part of myself, I need to go along with other people for, for whatever reason. And to your point, it's exhausting. If you never quite feel like you're being true to yourself, you're playing a role. And so having that sense of who you are, I think of it in a couple of ways is number one is it gives you kind of guideposts for how to behave like I think of it when you're in a, in a situation where there's some uncertainty about which path to take, I often say, choose the path that's in greatest alignment with your values, and you'll rarely ever go wrong. Because too often we're trying to calculate based on other things, and then that's where regret comes in. Or, you know, we don't give ourselves the chance to take the kind of risks that are going to be good for us. And so really using that as a way of staying true. And then also acknowledging, just because your values are different, doesn't mean you're wrong, right? Just because you have different values than the person next to you, or even the group next to you doesn't mean that they're not, they're not worth expressing that people wouldn't benefit from hearing your point of view on it. And if you're not connected to those values, it's really hard to access them in the moment.


Ben Grimes

Absolutely. And, and I think you're, you're exactly right, that that the different perspectives, the different value sets that we bring that inform group decision making are supremely important. And when it comes to joining a group, you talked about marginal, marginalized folks often having a sense of needing to conform to the norm. That's why I think organizational values and identifying organizational values are so important because if the norm has to be something more than just a surface-level expectation of how we look and talk and dress, the, the, the norm to which we're conforming should be based in values and principles. And if those values and principles are firmly rooted, then they can acts that input from a variety of different perspectives. And that's the norm that we would hope to see in a dynamic and diverse organization.


Kim Meninger

Now, I have a question for you, I'm going to put you on the spot here. So feel free to tell me if this is out of scope for the work. Because this is, you know, kind of the, the work we're all trying to figure out right now. But you talk about coaching and supporting individuals, do you think about how to make these kinds of changes at a more macro level?


Ben Grimes

Yes, absolutely. And part of the part of the work that I do is certainly the one-on-one coaching. And when the person that I'm coaching is a senior leader, in a law firm, for instance, then there's some broader impact. But I also work with to do things like strategic facilitation. And so working on that multi-year strategic plan, you know, a piece of that strategic plan, a critical piece is identifying and articulating the organization's values. And then making sure helping the organization message that through policy work, through standards of operating standard operating procedures, for instance, and then expectations of actual performance on the ground. Because if you don't have alignment between what's on the website, and how people actually act in person, then you're missing, you're missing that the value of values.


Kim Meninger

Yeah, and I think that's such an important piece of this, because we're individual coaching is so important, and people benefit tremendously from it. But it's really hard to create change in a vacuum. Yes, so as individuals are connecting with their own values, and you know, growing in the ways that we're talking about putting them back into the same on enlightened


Ben Grimes

Yeah, and on that point, what, so one of the things that that I like to do, particularly with, with the law firms that I work with, is contract with them to do to provide one-on-one coaching for a cohort of new leaders. So you've got a new class, which typically, in a law firm, there's a new class of law firm partners, and there'll be anywhere from six to a dozen, or two dozen or three dozen, but to take all of them or some of them and, and provide them the one on one coaching, that's going to facilitate this kind of higher-order leadership, and include a workshop for the, for the office or for the firm, that's going to provide the language that everybody can be familiar with. And then so that the language is out there, and then the behavior starts to mirror the language that everybody is expecting. And that way you start to get, that's another way of getting kind of more programmatic or systemic change in an organization.


Kim Meninger

I love that I think you're absolutely right, giving people sort of a shared foundation that they can get back to right what after the course ends or the, you know, the coaching ends, is there, I always try to think about the full cycle of our experience in the workplace. And there are times when it's just not the right fit. And I wonder how you think about that to have? How do I know if the reason why I'm struggling is because of something I need to think about? And, you know, an area where I need to grow versus this is just not the right environment?


Ben Grimes

For me. I think I think that comes back to the values work, and really understanding what are the organs. What are the values of the organization in which I find myself to the best that to the best that I can identify them? Because sometimes what's written again, on the website is not what I'm getting in practice. And so identifying what in practice are the values of the organization. And, and spending time to identify what's important to me, and what are my values, because that feeling that you're describing of like, this isn't the right environment. For me, that's a misalignment of values. And the more work that we do upfront to identify those values, the easier it is too for, for someone to identify, this isn't the right place for me. And now I know how to look for the next right place. Because I've got, I've identified what's important, and I know how to look for that in the next organization.


Kim Meninger

Yes, because what I often worry about is if we're not doing that work, we're just carrying the challenges from one place. We're not able to properly vet an opportunity for whether or not it is the right fit, and it's usually a combination of things and there's always something we can work on. But if you want to bring your, your best self to that next opportunity, whatever it looks like doing some of that inner work too is really helpful.


Ben Grimes

I think that's really important because if you don't, don't do that, and you look for the next right place and the next right place in the next right place, and none of them are the right fit. It gets really frustrating. And it gets very demoralizing to think, well, you know, is there something wrong with me? What No, there's nothing wrong with you just haven't identified what your values are so that you can find the right place. But, you know, until you do that, it gets really, really hard and really, really frustrating to keep going.


Kim Meninger

Absolutely. Oh, my goodness spend, I could spend all day. And I'm, I have to say, I have shown a lot of willpower because there's so many more military questions that I had. But I'm so grateful to have had this conversation with you. Do you have any final thoughts? And most importantly, where can people find you if they want to learn more about you and connect with you?


Ben Grimes

Yeah, no, I invite people to, to connect with me on LinkedIn. I'm at Ben Grimes. And also check me out on the website. It's BKG leadership coaching.com. I've got a little piece of bio, you can see what I'm doing back there. But most importantly, if you're interested in what I do with leaders, and especially with lawyers, just set up a legal leadership strategy session with me. We'll hop on the phone and talk about where you're at and where you can go.


Kim Meninger

Wonderful and we'll put those links in the show notes as well. Thank you again, Ben. It's been such a pleasure.


Ben Grimes

This has been a lot of fun, Kim, thank you.

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