Thirty Minute Mentors Podcast Transcript: Lieutenant General Mary O'Brien

I recently interviewed Lieutenant General Mary O'Brien on my podcast, Thirty Minute Mentors. Here is a transcript of our interview:

Adam: Our guest today is in a rare group of women who have ascended to the highest levels of leadership within the military. Lieutenant General Mary O'Brien served in many leadership roles over the course of 38 years in the United States Air Force, including commanding the Air Force's premier military intelligence organization, and most recently, leading one of the Defense Department's most important modernization initiatives. General O'Brien, thank you for joining us.

Mary:  Thank you, Adam. I'm really excited to be here.

Adam: I'm excited to have you here. You grew up in suburban Detroit and you studied chemistry at the Air Force. You enrolled at the Air Force Academy about a decade after President Ford signed the legislation that permitted women to enroll in service academies. Can you take listeners back to those days? What drew you to the military and to the Air Force? And what early experiences and lessons shaped your worldview and shaped the trajectory of your success?

Mary: That is a great question. Going back a lot of decades, but I'll say it started with the space shuttle and science. There was a time in my life I said, I want to be on a space shuttle. And I knew that I couldn't fly it because I couldn't see the big E. I had terrible vision, but you could be a mission specialist. And so, I did. I took every AP science class that was offered. When I got to the Air Force Academy, I was able to test out freshman chemistry. so, they thought I was very strange. I liked chemistry. But even getting to the Academy before that is a story. so, I was the fourth child between my mom and my stepfather to start college in four years. 

And the older three had all gone away to school. And at that point, money was kind of tight. I was going to be the fourth kid in college. And so, I was like, well, I'm going to figure this out. And I applied for a ROTC scholarship to Purdue, which I got. And there was a box on the form that said, if you're actually also interested in the Air Force Academy, check here. And I thought, OK, sure. And I checked the box. I got accepted to the Air Force Academy, coming home from my visit to go make sure that I wanted to go there. I had a letter in the mailbox before I even got out of the car that said, you failed the hearing test. 

As a result, we have taken away your scholarship to Purdue. We have taken away your admission to the Air Force Academy. And I have this letter. I've shared it with people since then, that you never know how life is going to turn out. And at the end, it was, if you have any questions, call this number 301 blah, blah, blah. We do not accept collect calls. And so, I didn't know what I was going to do. And as it turned out, I got a waiver for an organization called the DoD Military Evaluation Review Board. 

And they gave me a waiver for low-frequency hearing loss that nobody actually talks at, only to go to the Air Force Academy. And so, that made the choice a little easier. if I wanted to go to college. And so, I ended up with the Air Force Academy. At 17, I didn't know that it was still kind of new until I got there. And a lot of my instructors were captains from the class of 1979, which was the last all-male class.

Adam: Wow. A lot there to unpack. Talk about an early obstacle to overcome that you were able to overcome. so, many people would get that letter and stop in their tracks and move on. You were able to take that and get around it.

Mary: Yeah, I think when I was that young, you haven't heard no as many times. And so, the way I've always been is it's not over till it's over. And they said in paragraph three, if you want to apply for a waiver, write to these people. Okay. And so, it wasn't over until it was over. There was still one more step. And so, I just pursued that next step. And knowing what I know now, I'm still a little amazed that I got that waiver because those waivers are very difficult to get.

Adam: And it's a really important lesson. It's not over until it's over. The importance of persistence. Whatever you're trying to do, you're going to hear a no and you're going to hear no a lot. But how do you get to yes? A lot of it comes down to what you just shared. Having the mindset that a no might mean no, but it might not necessarily mean no. A lot of it really comes down to your willingness to figure out a way to get to that yes.

Mary: People may think they've told me no, and I'm sure that I have bosses out there that would agree. They may think they told me no, but what I heard was not yet. And I deliberately dared that as I became a leader through the years someone would come to me and want to do something and There would be merit into the idea, but maybe we didn't have funding. Maybe we didn't have the right skills yet. Maybe the right technology wasn't available yet. 

And I would say, I'm not telling you, no, I'm saying not yet. Let's find out how we get more money? What training do we need? Bandwidth was an early, early obstacle for many of the things. that my organizations were trying to do. Sending video, things like that. Bandwidth was very expensive. Not the way we're talking today. We take it for granted, especially since COVID, that we're going to have audio and video and there's not going to be any latency or echoes. so, anyway, my view has been, I heard not yet. Not a no.

Adam: I love that and not only is that a great lesson in career development and how to become more successful, how to take that next step, how to get to where you want to be, but it's a great lesson in leadership. Don't tell the people who you're leading, no, you can't do this. There might be a great idea that you're just shooting down. It's a great way to stop innovation by instinctively saying no. But what if instead you reframe that and you say, not yet. How do we get to yes? Let's figure out what steps we need to take to turn this no into a yes. And as a leader, my job is to help you get there. My job is to help you turn this no into a yes.

Mary: You are so right, Adam. You are so right. And as I wanted to become a better leader throughout my career, you would find that, yes, you did have that innovator who had the great ideas, but maybe they were missing a skill set. in order to really execute on the idea or put together a roadmap with milestones, how much is it going to cost, things like that. And so, I deliberately have sought out different resources on how to create a high-performing team, as very few successes will be the result of one person's good idea. 

And so, whether it was a Harvard Business Review article that I have shared, since it was printed, with every command and organization before that. And it would say the new science of team chemistry. And I love that because I'm a chemistry major. And it would talk about putting together the team you needed. You would need your pioneers. There's that innovator, like, why aren't we doing this? then you would need the driver. That's the person who's like, okay, we've made this decision and let's move out. What do we need? And then you might have a guardian. 

And some people in the Air Force get lumped unfairly, in my opinion, to be the frozen middle. That's a phrase that we talk about, the reason we don't have innovation. But I believe you still need your guardian who is making sure that you're not getting outside boundaries that are in place for a reason. But I wouldn't want a team of all guardians, just like I wouldn't want a team of all pioneers or all drivers. I don't care where we're going or how we get there, but we should go faster. And then the person, the kind of the team characteristic that keeps those three from killing each other is your integrator. 

So, having the integrator who can speak all three of those languages, and take those very distinct skillset, and form the team. And so, I would deliberately look around my organization, and get a feel for who's the person with a good idea? Who's the person who maybe isn't the most innovative, but once you tell them what they need to do, come back with an Excel spreadsheet with the 12 steps you need to get there. Well, this is how we could get there.  wonderful. And so, to me, getting to yes has a lot to do with putting together the right team.

Adam: You shared so much great stuff there. A line that you shared which jumped out at me, very few successes will be the result of one person's good idea. You need a team. You need a group of people to take that good idea and turn it into something real. And I've heard this over and over and over again from the most successful entrepreneurs. How do you build a billion-dollar business? It's not by having a billion-dollar idea, snapping your fingers, and next thing you know, it becomes a billion dollars. 

Every single entrepreneur who I've spoken to who has started a multi-billion-dollar business has told me, it's the execution, not the idea. and what you just shared, the importance of leaders understanding and leveraging the strengths of every single person on their team. Every person on your team is going to have something that they bring to the table that can allow them to make a significant contribution. They're going to have things that aren't going to be great.

And what are you going to look at as a leader? Are you going to look at what they bring to the table that is a strength? Are you going to look at what they bring that's a weakness? Are you going to ask the person that's really good at putting together Excel spreadsheets to sit in a room and generate ideas? Or are you going to ask that person to take that idea and help move it forward? so, I love what you just shared.

Mary: Thank you. The team still needs leadership. And so, I think it's not a high-performing team instead of leadership. It's leaders putting together a good team. I found that sometimes leaders are afraid to make the changes or they don't recognize when a member of their organization is not in the right spot. And so, over time, I've learned that it's better to make those changes early. And in no way do I mean we're firing them. In the military, we don't fire people, but there's a perception. And so, I think the time that it became most obvious to me, the value of recognizing an individual's strengths and then making the adjustment if needed. I had an assistant that worked for me. 

And quite honestly, he was not very good at doing the things that he was supposed to be doing, not because he wasn't trying. He was staying till 8, 9, 10 o'clock at night. And I also had a family. I didn't want to do that, so, I didn't. so, finally, one day, instead of sitting him down and saying, hey, you're not doing a very good job, because it turns out he already knew that, I said, hey, how do you think you're doing? And he said, Ma'am, I feel like I'm letting you down every single day. And it was just like, I am not setting up this person for success. And I said, Let's talk about it. And he was in a job that had a lot of interruptions throughout the day. And he was just not that type of person. It took him too long to regain his focus on whatever it was. 

And I said, well, is there a job in our organization that you think you would be really good at? And he was an engineer and he was smart. And he said I think I would be good at that. And I said, all right, well, we're going to make a change. I said you are not being fired. We need somebody who can do what you do over there. And we're going to put you over there so you can be successful. And he's gone on to continue to have a very successful career. And we said, well, what did you learn from that? 

And he said I learned that it's better to improve my strengths than spend so much time trying to become adequate at my weaknesses. And so, I think leaders owe that to their teams to put the right people in the right jobs, and be very transparent with them. Instead of everyone just pretending that this person is doing what the team needs when everybody knows that they're not, and then not taking action on it. That transparency to bring that conversation out into the open, I think is another critical component to leading high-performance teams.

Adam: We could spend the rest of the conversation, and well beyond this conversation, just breaking down that story. There's so much to it. And something that I really love about the story that you just shared, the power of self-awareness, the person who you were leading, having the self-awareness to understand and accept that I'm just not good at this. I'm not doing a good job. He didn't try to defend himself. He didn't try to say, I'm actually doing a pretty good job, but he didn't try to explain himself. He didn't try to make any excuses. He was open. He was honest. 

And because he was aware because he possessed that honesty, it allowed you and him to handle it the right way. At the same time, you demonstrated self-awareness as a leader to recognize that it's on you as a leader to put him in the right position to succeed. And the fact that he's there staying late and not performing to the best of his abilities. That's not only on him, but that's on you. And you didn't deflect responsibility. You took accountability as well. The power of self-awareness, the power of accountability, holding the people who you lead accountable, holding yourself accountable.

Mary: Yeah, I would say that self-awareness is critical, although sometimes it takes somebody else to help you gain it. That is a critical competency that leaders should have. I'm going to tell you a short story about a time when somebody helped me gain some self-awareness that for years I had no idea. The Air Force sent me to a leadership development program run by the Center for Creative Leadership. It's fabulous. You take surveys and get 360-degree feedback and all of that, and then you meet with a coach. And the coach said to me, you have a learning style where you learn by asking questions. I said, absolutely. And like to make data-driven decisions. I'm like, doesn’t everybody? And she said, well, no, not really. And I was like, really? And what they were doing is taking your own personality traits and showing you what would happen if they went to the extreme. 

So, your risk of what the military calls senior leader derailment. Sometimes people get off a leadership track and they have no idea why. And she said, your risk for senior leader derailment is being perceived as skeptical. And I was shocked. I'm like, really? How could that be? And she said, well, when you ask a lot of questions, people may think you don't support whatever the concept is you're talking about. And of course, if you're the boss, you can ask as many questions as you want. But when you're asking those questions of your boss, your boss can absolutely think that you haven't bought into what you've been asked to do. 

And I kind of sat there for a minute and I said, I don't think I can stop asking questions. It's how I learn. What am I going to do? And she said, well, you could tell people in advance that that's your learning style and that you are supportive of whatever it is, but you want to learn more about it and what they need from you as a leader. in order to have them, because people would say, and I didn't learn this until I came back and I shared with everybody, hey, I went to this course and this is what I learned. And the whole room kind of laughed. And they said some of the people have come to brief you. When we ask how it went, they said she hated it. She ripped it to pieces by asking so many questions. And then they would be surprised because later I would say, Captain so-and-So, had the best idea. Let's do whatever we can to make that a reality and people were confused. And I thought, and I just remember thinking that would have been useful information for me earlier in my career. 

So, I think we can't assume that we have self-awareness, that you really need to seek it out. And then again, not be defensive if somebody tells you, but okay, what can I do to become more self-aware, and then what tools can I use to turn it into a strength? I would go visit my units all around the globe, and a senior airman, a very young, low-ranking person would be selected to give me a speech about a unit's success. And that's wonderful. And they would be nervous. I would let them go through, and they usually rehearse, do run-throughs weeks ahead of time. 

So, I would let the airmen finish. And then I would say, I learned by asking questions. Can I ask you some questions? And I would say, hey, that is an incredible success. I'm so proud of you. That's awesome. What if we could take that and do it in other squadrons. And so, I'd say, was this difficult? And they would say, yes, ma'am. And I'm like, well, did it take a long time before you saw any signs of progress?  Yes, ma'am. Did you have to start over? Were you headed down the wrong path for a solution and have to start over? Did you have the right tools? Well, no, we had to create a new application to convert the software. 

And I'd say, well, what's the critical link to solving the problem if we wanted to do it in more places? And they'd say, well, it just turns out that Sergeant Jones is a native Russian speaker, or Airman so-and-So, is self-taught for programming. Or, we had this 3D printer that had sat in a corner for five years that we bought with innovation funds, but nobody knew how to use it. 

And this person came in, and now we can create discontinued parts. for a legacy capability that we need to keep going. And at some point, because the questions were not interrupting, we eventually became science nerds, talking about how we could take this success and share it with all of our other units. I don't think I would have been as good at that if I had not received the feedback from the 360-degree surveys, and the coach who was able to interpret it for me.

Adam: I love that. We all have blind spots. How do we understand what our blind spots are and how do we get better? How do we develop self-awareness? Feedback. Another important lesson from what you just shared - the importance of communication. You're never going to get hurt by communicating more, by expressing yourself in a more comprehensive way. Communication - essential to great leadership.

Mary: I agree. And I would expand that to communicating with a wide range of people. I got the idea for what I called my under 30 mentors. Not people that I mentored, but young people who we sent out an announcement. People got to volunteer to be one of my under 30 mentors when I was a two-star general. One day, I have a son who's in college now, but He's a big gamer, and I would hear him talking, yelling, shoot him, shoot him. Okay, we're military, my husband's a Marine, so, yes, some of the games might involve shooting. And he was saying the names of one of his friends, and I said, hey, I haven't seen so-and-So, around lately. And he was like, Mom, he moved to South Carolina three months ago. 

And I had no idea because they were still communicating over the gaming platform. And it kind of triggered some ideas. My years at the Academy, I was the last class that was not issued a personal computer. The class of 90 were all issued Z248 computers. My first unit, we did not have a computer. There was no internet. We eventually received one computer for 10 people, and we had an intranet where we could only email other people on our own base. 

So, over 38 years, technology has come a long way. And have our senior leaders kept up with it? And so, I thought to myself, a lot of these airmen are also using these same platforms. And how do they communicate with each other? And where are they getting their sources of information? And I realized, right, that I was a generation removed from our newest airmen. And so, I sought out these under 30 mentors, and I would, no surprise, ask them questions. What are the airmen talking about? How are the airmen talking? Where are the airmen getting their information? 

And we discovered that some of the places they were getting information, valid information, are sites that were blocked by our old network policies. They're not reading newspapers anymore. They're not reading memos that get sent out across our Air Force all email distro. They have other sources of information. And so, that communication has changed a lot. And if we don't deliberately, I think, reach out to the newest generation of airmen, we’re not communicating with them.

Adam: We might think we are, we might be talking at them, but we're not talking to them. Great leaders ask great questions and you might have had some reticence receiving feedback around you're asking questions, but I'm like you. I ask a lot of questions. Not only do I do it on my podcast, but I do it all the time. That's how I learned something that I've learned from my conversations with the most successful leaders, the most successful people. are constantly trying to learn, constantly trying to grow, constantly trying to get better. And how do they do that? From pulling in the perspectives and insights from everyone around them, no matter who that person is. 

And the story you just shared about trying to learn from people under the age of 30, don't dismiss people who you might think haven't achieved a certain level of professional success, life experience. Every single person has value that they can provide you and it's on you to walk into every interaction with the perspective of what can I learn as we're chatting. Story that comes to mind. I did an interview with Jim Weber the CEO of Brooks the running shoe company and Brooks is part of Berkshire Hathaway, and I asked Jim What have you learned from your time spent with Warren Buffett? 

And he told me that when he was first spending time with Warren Buffett, He assumed that the relationship would be him listening to Warren Buffett speak. You're around arguably the most successful business person of our era. And what he told me is that the encounter was actually very different. It's Warren Buffett asking Jim questions, trying to learn from Jim, trying to figure out what he can walk away from this encounter from to allow him to become better. And that's what makes Warren Buffett Warren Buffett. That's what makes the greats great.

Mary: You are very generous. I would not put myself in the category of Warren Buffett, but I will extend compliments to you. You do ask very good questions on your podcast or you wouldn't have well over 200 at this time. Your podcast is very successful and because you're asking questions. Of course, I love that because I'm like, I’m a question asker, but asking the right questions is a skill.

Adam: And it's an interesting point because I do a little bit of teaching at UCLA and what I try to convey to my students’ is don't be afraid of the questions that you're asking. Don't worry about what questions you're asking. Ask the questions that you're interested in asking, that you're genuinely curious about. And that's where the great content is ultimately generated.

Mary: Yes, I would agree with that 100%. There is a stereotype of certain senior military officers that would ask gotcha questions, questions where they already knew the answer. And that is not leadership. And so, I may have my peers and their learning style may be different. And they may be learned by reading or learned by listening. And then you have to adapt to support them. When I was in Afghanistan, in 2014, I originally worked for General Dunford, who eventually became the chairman of the Joint Chiefs of Staff. And he learned by reading. And so, every day we would give him the information he needed to lead our forces over there. 

And he would read every word and he had a green pen and you could see his check on the page. And then you had to search through the pages because he would ask some questions in that green pen. When he left and the replacement Army General came in, because I think of feedback I had, I asked him, sir, what is the best way for us to give you information that is useful to you? Many organizations keep doing what they were doing. And if we had done that, we would continue to provide this binder with 50 to 100 pages of reading every day. And General Campbell said I like to learn through discussion and listening. He was an auditory learner. 

And he said if we could set up a time to bring in the senior analyst after the big staff meeting, and then she can't go over the highlights that the information that she thinks I need. And so, we changed all our processes in order to support his learning style as a leader. And so, I would never suggest that somebody would be a better leader if they had my learning style of asking questions. But as you mentioned, have that self-awareness to know what you’re learning style is so that you can share it with your teams and then they can provide you the information in the format for you to lead and support that team.

Adam: What do you believe are the key characteristics of a great leader and what can anyone listening to this conversation do to become a better leader?

Mary: There's an awful lot to the key characteristics of a leader. There are the ones that are enduring, there's integrity, there's empathy, there's intellectual curiosity, there's being bold. There are ones that come over time. I think some of the competencies leaders need today that they didn't need in the past is they really need to start to understand the technology that is now in every part of our lives, whether it's national defense, whether it's business, whether it's entrepreneurship, getting at least to digital familiarity or to digital fluency, depending what their industry is or what they're doing. 

But this is not going to surprise you. I think asking good questions is really important for a leader. And back to the Ted Lasso, episode where he said, be curious. And so, I eventually learned to end all of my briefings and meetings and orientations and unit visits with the same question. And I would say, I've asked you a lot of questions, and thank you for your patience with answering my question, because that's how I learned. Is there a question that you had hoped I asked that I haven't asked you yet? And what is it?

Adam: What's the most interesting answer you've gotten to that question?

Mary:  they're just so surprised by the question. They're like, oh no. They're like, I'm nervous in front of the general. But what I find out is there's information that would never have come out without that question. They might have had the answer to something that we've been struggling with for three or four years. And so, I've received a lot of very useful information. I don't know that the most interesting one is probably classified, it would get me in trouble. But it has been a very powerful way for me to learn things that I might not have even known to ask.

Adam: General O'Brien, what can anyone listening to this conversation do to become more successful personally and professionally?

Mary: I would say continue to keep learning, asking questions, and work on your self-awareness. All of those things begin with wanting to become a better leader. so, the very first thing you have to do is decide. I want to become a better leader and then figure out what are the things you need to do to get there.

Adam: General O'Brien, thank you for all the great advice and thank you for being a part of Thirty Minute Mentors.

Mary:  Thank you, Adam. This has been a fabulous experience.

Adam Mendler is an entrepreneur, writer, speaker, educator, and nationally recognized authority on leadership. Adam is the creator and host of the business and leadership podcast Thirty Minute Mentors, where he goes one on one with America's most successful people - Fortune 500 CEOs, founders of household name companies, Hall of Fame and Olympic gold medal-winning athletes, political and military leaders - for intimate half-hour conversations each week. A top leadership speaker, Adam draws upon his insights building and leading businesses and interviewing hundreds of America's top leaders as a top keynote speaker to businesses, universities, and non-profit organizations. Adam has written extensively on leadership and related topics, having authored over 70 articles published in major media outlets including Forbes, Inc. and HuffPost, and has conducted more than 500 one on one interviews with America’s top leaders through his collective media projects. Adam teaches graduate-level courses on leadership at UCLA and is an advisor to numerous companies and leaders. A Los Angeles native, Adam is a lifelong Angels fan and an avid backgammon player.

Follow Adam on Instagram and Twitter at @adammendler and on LinkedIn and listen and subscribe to Thirty Minute Mentors on your favorite podcasting app.