When Failure is Not an Option

Host, Ken Harbaugh, interviews political leaders, influencers, and other history makers about the choices we confront when failure is not an option. Choices like Alexander the Great made when he landed his troops on the shores of Persia and ordered his men to burn their boats.

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Mike Howard: Keeping America Secure from the CIA to Microsoft

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Mike Howard: Keeping America Secure from the CIA to Microsoft

Mike Howard, a veteran in the security and protection field, comes on Burn the Boats to talk about his 22 year career with the CIA and the years he spent as Chief Security Officer at Microsoft.

Keep an eye out for Mike’s upcoming book on leadership, out later in 2021, titled “The Art of Ronin Leadership: Strategy, Execution, Sustained Success.

Ken Harbaugh: Burn the Boats is proud to support VoteVets, the nation’s largest and most impactful progressive veterans organization. To learn more, or to join their mission, go to VoteVets.org.

Mike Howard: We like to think of ourselves in the clandestine services as tip of the spear. But the idea is that as a democracy, it is imperative that our policymakers get the best information they can so they can make the best decisions in the national security interests of our country.

KH: I’m Ken Harbaugh, and this is Burn the Boats, a podcast about big decisions. On Burn the Boats, I interview political leaders and other history makers about choices they confront when failure is not an option.

Mike Howard is a former station chief for the CIA and corporate security expert. After his career in government, he served for over a decade as the Chief Security Officer for Microsoft, overseeing physical security worldwide for the company, including the personal security for Bill Gates. Mike, we spend quite a bit of time on this show talking to politicians and policy makers about geopolitics. So I have really been looking forward to the chance to talk to you because you're someone who served on the front lines, not only having to execute those policies, but having to live with their consequences. Great to have you on. Welcome to Burn the Boats.

MH: Thank you, Ken. I really appreciate it. I'm honored to be here, honored that you asked me to be here and yes. No, I'm not a politician so I can speak from hopefully a different optic on these matters.

KH: Before we dive in, why don't you give us the quick overview of the career of Mike Howard, because it has taken some amazing twists and turns.

MH: Thank you. Yeah, it has. I grew up in Northern California. Always wanted to be a police officer, probably saw too many cop movies when I was growing up. Eventually I became a criminal justice major and ended up working in the Oakland Police Department in the late seventies. Unfortunately, Oakland has a lot of crime, but it was a great place to learn to be a police officer. Read a book one day, off duty, called Piercing the Reich, which I still have a copy of in my office. And it was about how in World War II, the OSS, the precursor to the CIA, the Office of Strategic Services were sworn up to take on Nazi, Germany and Nazi-occupied Europe. I thought, "Well, that might be interesting." And I wanted to travel the world, ended up going to, believe it or not, CIA had open recruiting offices in the federal buildings back then. It was during the Reagan buildup. After he got elected, they were hiring more law enforcement and military police. So joined the CIA, spent six years in their, what they call, Office of Security doing a lot of things I did later in life in the corporate security world, including the two years on the Director of CIA’s protective detail. Made the jump over to, sometimes we call it the dark side, the clandestine side of the house. Worked in the Director of Operations in our counterterrorism center for a vast majority of my career. I spent 22 years at the CIA. My then-wife, who unfortunately passed away a few years ago, was also CIA. We decided we'd had enough of Washington. I'd done everything I wanted to do there. And through a couple of twists and turns, as you said, I ended up at Microsoft. The first year running the executive protection for Bill Gates, Steve Ballmer, and some of the top executives there, and then morphed into becoming the Chief Security Officer for the bulk of my 16 years there. And now I'm happily retired in Las Vegas with my wife.

KH: Watch out for the strip on payday. Right? You joined the CIA at the height of the Cold War, but found yourself in counterterrorism. Was there tension there? Was there a friction between those two missions, especially given the nature of the Reagan buildup and what was perceived as the major threat at the time?

MH: Yeah, that's a great question, Ken. I've really never been asked that, but there was. Counterterrorism Center was formed around 1986 and it was the first time they were bringing in analysts and operators together to work after a common target, primarily our Near East division, as they called it at the time, they were responsible for all the counterterrorism issues. So having this new entity, there was some friction in terms of the NE division saying, "Well, what are you guys going to do that we can't do?" And also there was a time, believe it or not, at CIA where analysts and operators didn't talk to each other. They really didn't talk to each other unless they had to. CTC was the first time we brought the two groups together against a common target working together the way it should be. There was friction. It took some growing pains, but we eventually got... CTC made its bones in terms of its ability to run operations, to be effective, and also to collaborate with our brethren in the NE division because basically we're all after the same bad guy, serving the same flag.

KH: Was that firewall between the analyst and the operators a cultural thing? Was it a legal thing? Because I have to imagine that the operating instructions for both groups were a little bit different. In clandestine ops, you had to bend and sometimes I would imagine break rules in a way that would've made others uncomfortable. Am I right?

MH: You are absolutely correct. Two different mindsets, the operators felt that they were hired because of what you said, their ability to be a chameleon, to morph, and to do things that they had to do. Analysts are pretty, obviously, straight by the book. Operators didn't trust analysts to keep their mouth shut, to not talk out of turn in other places because they weren't trained that way. Things have changed now where analysts get a lot of the same clandestine training, operational training, as the operators. So they understand the parameters, what the operators do, and why they do what they do in terms of need to know and compartmentation of information. But back then, yeah, it was a huge cultural divide. Analysts, obviously, very necessary. They can give you the big perspective, big picture thing that you need as an operator to operate in a particular country. But there was certainly not a lot of trust or love lost between the two until, again, I think the centers spent, whether it was the Counterterrorism Center, Counter Narcotics Center, what have you, kind of broke the mold of bringing the two sides together to work hand in hand.

KH: There's a cryptic line in your LinkedIn profile that says simply "Operations, U.S. government, 22 years." I love that because whether you intended it to come across this way or not, it is something of a political statement. I'm referring to this idea that without what you were doing, and your brothers and sisters at CIA, the implication from that line in your LinkedIn bio is that the U.S. government would not operate, would not function. Can you speak to that as someone who has been as deep in the clandestine world as you can be, and just how important that is to the functioning of government and how overlooked it has to be?

MH: Yeah. People always talk about tip of the spear. You, in your profession as a fighter pilot, you were tip of the spear. We like to think of ourselves in the clandestine services as tip of the spear as well. In order to, I mean, when this country was founded, there were spies way back even in George Washington days. Right? But the idea is that as a democracy, it is imperative that our policymakers get the best information they can so they can make the best decisions in the national security interests of our country or in the economic security interests or political interests. To a great extent, CIA officers are the ones that provide that information. The operators who actually have to meet with assets, clandestinely, get information that we normally couldn't get as a country so that our policymakers have that holistic view of what's going on. I think, in fact, I know that this country would be less safe and would not be, in terms of information that our policymakers need, we'd have a gap if it wasn't for the operators, along with the analysts, obviously, who put a lot of that information together to get it to the policy makers. There'd be a huge gap. And so it's necessary. Operations is a necessary part, in my opinion, of any of any democracy. They have to go hand in hand, but you can't have one without the other.

KH: It's that friction that really interests me. And you alluded to it earlier, when you talked about operators having to do whatever it took to get the job done. Did that ever put you in a compromising position? We know historically it has, when we look at some of the decisions made at CIA, especially after 9-11. How did people in your position balance those dilemmas?

MH: There's always guidance, right? Legal guidance. We have a huge legal team there. They have these things called findings. So if there's a finding to do X in a particular country, that maybe the president and national security entities want the agency to execute off of, that has to be written off legally. There has to be a legal finding that we in the agency have the authority to do that. The agency has wide latitude, internationally, as most people know, or some people maybe don't know. I mean, that's what we were created for, but under legal guidelines, especially after the seventies, during the Church Commission, when a lot of the abuses of the agency came out, there are a lot more restrictions on what you can and cannot do. At the end of the day when you're given a marching order, you have to look at within yourself, obviously as a person, not just as a CIA operations officer, as to whether you believe that order is legal, in some cases, moral. There's a lot of gray, obviously, in our world. And one of the things they look for in our psychological profiles when we go through our evaluation process to become a CIA officer, is can you follow the rules of the agency, the laws of the United States government while still operating in a foreign country, in many cases in effect breaking the laws of that country by conducting espionage operations there. If you can't reconcile that with yourself, this job is probably not for you. I would say I never found myself in a compromising situation. I always felt I had legal authority to do whatever we had to do and I believed that whatever we were doing was in the best interest of the U.S. government. I also, because I was a cop, because I was raised a Christian, I've got a moral compass as well. So we're not automatons, just like you and your former colleagues in the military. We have feelings, we have consciences and if it ever came to that, which it didn't, I knew I would hopefully be able to step up to the plate and say "no" or say, "Hey, we've got to pause here. Are we sure we want to go down this route? Does it make sense legally? Does this make sense morally? Operationally maybe it does, but is there another way?" I didn't find myself in that particular situation, and I probably- knock on wood, I didn't have to.

KH: We've talked to a number of folks with strong perspectives on this from Leon Panetta to Stan McChrystal, but being on the receiving end, at the tip of the spear, as you said, did you find yourself having to play lawyer more than you wanted to? This is something I've written about in The Atlantic when it comes to the military, having to make constitutional decisions now. Were you ever in a situation where you thought your legal expertise didn't meet the moment?

MH: No, I don't think so, but I was blessed to be in a time when... When I got in there in the eighties, it was the Cold War, but it was also Hezbollah and some of these nation state organizations. We'd just lost William Buckley, one of our Chiefs of Stations in Beirut. The gloves proverbially were off to go get these guys. And then the Iraq War, Gulf War I came around. And again, we were always in a good position. I know what you're alluding to because during the recent wars, there've been these situations where you've had enhanced interrogations and the people that were doing it there, I think were doing it fully understanding that they had the authority to do so. We were told as an organization "gloves off," right? I mean, we lost thousands of people in 9/11. We weren't going to let that happen again. Hindsight's always 20-20. Not all politicians are bad, you can't broad brush everybody. But it's interesting that, in my optic, there were people in political positions that said, "Hey, go get them” and “no problem" at the time. And then afterwards, when there's blowback, "Well, you shouldn't have done that." Well, as an operator, you kind of don't have that luxury, right? Similar to the military, you're given an order and yes, you can defy it if you think it's wrong, but I think you take everything in terms of the times, the context of the times in which that particular operation or activity was taking place. It's okay to do reviews and to say, "Okay, could have done better here, could have done better here," but to take today's world and then project it back to when those things were taking place, I think is unfair to the boots on the ground who are just trying to do a good job.

KH: You mentioned the military, which I served in and still stay very close with my buddies from those days, and there's this ethos among uniform personnel that it's not only a moral obligation to disobey an illegal order, but a legal requirement. Is that same lesson drilled into you at CIA?

MH: It is. It really is. Because of the fact of the latitude that you have overseas and what the nature of your job is - there's some covert action, there's recruitment of assets to spy on their host governments or other organizations - there has to be that balance, and it is drilled into you that if you have any questions about something... And maybe it wasn't like that in the old days. Old days meaning maybe the fifties or sixties. When I was there, yes, you had recourse, and it was taught to you in training about the things you can and cannot do. And if you have questions about anything, go up to your superiors, make sure. And then there’s always the IG route, right? You could always call the hotline if you felt that something was amiss and that you needed to report it to the IG. I actually served one year as an investigator on the IG staff at CIA, so I know that that is an avenue for officers, but yes, it is. Because ultimately at the end of the day, we're CIA officers, but we serve under the constitution of the United States. We have oversight. We constantly talk to the committees. After 9/11, I had to go with a group of Chiefs of Station to talk to HPSCI, House Senate Permanent Committee on Intelligence, about what we were doing post 9/11 with the FBI. And so, yes, that was drilled into you, as well as it should be.


KH: You eventually wound up as a Station Chief, I believe in the Pittsburgh office. To be honest with you, until reading your bio, I didn't realize that the CIA had domestic station chiefs. Can you explain that? Because the image of a station chief is someone deployed overseas in an embassy managing collection and analysis sometimes from there, what does a domestic station chief do?

MH: Sure. We've had these for years under many names. When I was there, it was under the National Resources Division. And what they do is twofold. Number one, they work with any businesses that are willing to help us out. And we're not talking about recruitment because we're not allowed to recruit American nationals, obviously-

KH: For the uninitiated, by recruiting, you mean assets? You don't mean staff. Go ahead and explain that.

MH: Yeah. So recruiting in our parlance is - Ken has access to information that I think would be valuable to the U.S. government. We have a set of requirements that we work off of in terms of whether it's political, economic, or terrorism, what have you. I believe Ken has some information. My job is to go through the recruitment cycles, spot, assess, develop, recruit, and report, so that at some point in time, Ken is reporting to me, clandestinely, information that he shouldn't be giving me, but we feel is important, obviously, to the national security. That's a classic CIA case officer and asset relationship. That's the recruitment. Getting back to domestic operations, again, taking you Ken as an example, if you ran a business and you did a lot of work overseas and you were willing to, not recruited, but you were just willing to, say, give us atmospherics on what you saw if you were dealing with certain government officials or different things. That's kind of one aspect of it. The other aspect of it is really working with the FBI. We don't have law enforcement authority, but we certainly have a lot of information and capabilities at our disposal in the agency. And back for most of my career, the FBI before 9/11 really didn't have much of an intelligence capability. They're a crime fighting organization and that's what they were great at. Post 9/11, we actually helped them to develop their intelligence division, which is great, where they now have analysts and things like we have. But those were kind of the two-fold things. We were not allowed to spy on American citizens. We weren't allowed to run covert operations in the United States. It was merely more of a partnership with businesses willing to help with atmospherics and also a lot of work with the FBI.

KH: Your career there spanned 22 years. And it bridged several very different geopolitical paradigms from the Cold War to what was originally called the Global War on Terror. With the benefit of hindsight, with the perspective you've gained over two decades plus in the CIA, do you think we're facing a more dangerous world now than when you joined at the height of the Cold War?

MH: I do. When I was in the CIA, I never thought I would ever say that. I thought whatever we had with Hezbollah and 9/11 and Al Qaeda, I thought, "Okay, that's the end all, be all." But that was a very kinetic world. Not that we don't have that today, but the world today is more amorphous, right? It's cyber. They can knock you out without having to put armies' boots on the ground or to break into a place to take out a server or something. I mean, it's the internet of things and cyber that's scary. It's the sort of geopolitical constant shifting of loyalties and allies. Even our allies in Europe, the traditional NATO allies, we can count on them, but again, it's a different kind of war.

It's a different kind of war than we're used to, than World War II, Gulf War I, Vietnam, Gulf War II, et cetera. Even what we have now going on in Afghanistan that at some point is going to be winding down. I think it's a much more dangerous world and I think you need perhaps the kind of talents that I didn't have growing up. I was kind of this traditional mindset. You need people with great business sense, people with great cyber skills. You need people with engineering skills and also geopolitical skills and kind of be able to forecast what's going on and what's going to happen in the world. So yeah it is a much more dangerous world and likely to become so in the future.

KH: Does CIA have its own operations and assets dedicated to cyber or do you mainly leverage NSA and Cyber Command and other agencies? Or is this something that you're prioritizing to the point of building that talent in-house?

MH: No, I mean, I think the agency has its own capabilities in cyber. I remember when I was at CIA, I visited a lot of different entities because we worked a lot with government as well. It seemed like at one point, everybody had a cyber command of some sort, right? It was Air Force and Army and blah, blah, blah. NSA, of course, is the big one. That's all well and good. I just want to make sure that we are all connected. Bigger is not always better. I'm not privy to this, I'm not in the government anymore. I just hope that with the advent of different cyber entities within the US government, that they are coordinating their efforts and that they're making sure that when you're going after bad guys, that it's not just a shotgun approach. It's more laser-beam focused approach to get the most bang for your buck. But yes, the agency certainly does have cyber capabilities.

KH: So you spent 22 years and then transitioned to the civilian world. What, at least on paper, looks about as far away from CIA as you can get, a stint running security at Microsoft. 16 years, right?

MH: Correct.

KH: But I would say one interesting area of overlap for me is that you went from projecting America's power through the force of its military and intelligence might to working at an institution that projected economic might. As part of that, you traveled the world. You were in charge of security globally for Microsoft, right?

MH: Correct.

KH: How did you see global perceptions of America shifting over the course of your career from let's start at the beginning in the Cold War, when America's security umbrella protected Eastern Europe, to your time at Microsoft where some of those same European countries were suing your employer for overreach and monopolistic behavior. How did you see on the ground perceptions of America and Americans evolving?

MH: Great question. Certainly I think in the eighties when I was working there and I had a fair amount to do with, obviously, foreign governments, foreign military, police, intelligence services... It wasn't naivete on the part of a lot of these countries, but there was a kind of putting you on the pedestal because you're an American. And because of the might of America, both military and economic, your democracy. I think to a large extent, there are a great deal of people who still feel that way. But I think there's a lot more skepticism about the ability of America to manage its affairs, the ability of America to straighten up its own house because of all the issues that have gone in place, whether it's economic or racial tensions or the economic divide. I think the way I looked at it, everywhere I went in Microsoft, we had subsidiaries all over the world. You talk to a lot of foreign nationals. I think the people at Microsoft who work for, whether they were Germany or Japan or Istanbul, they loved working for Microsoft. I don't think they looked down on us. There were probably people in those countries that didn't like Microsoft as an entity, but it's always a balancing act because you don't like it as an entity, maybe for whatever reason or any multi-national, but those multi-nationals employ hundreds if not thousands of the country people in that region. And so, I didn't see huge anti-American rhetoric, but certainly I don't think there's a looking at you from a pedestal. I think there's more of a skewed eye as to, "Okay, well, you're America, you're great. Economic might, military power when you want to project it, democracy." Some countries would love to emulate us, but it's also, "You're not perfect and don't come across as perfect. Don't talk down to us, we're all human beings." And I think that was kind of my perception over the years, that's what I saw.

KH: Do you think that is a healthier perception of America, especially as it projects power? Or do you think we have an opportunity to restore some of that lost luster as it were? Can we regain or reclaim that place on the pedestal? Or should we?

MH: I mean, I think we should. I mean, maybe I'm old school, but I think... I talk to people all the time, including my wife, and I say, "You know, it's funny. Whenever some bad stuff happens in the world, who are they calling?" Right? The world's not calling on Russia to help them out, or China. They're always coming to us. I'm not so naive when I was a kid thinking there's always white hats and black hats, right? There's a bit of a mix, but at the end of the day, I think America needs to lead, continue to lead the world in its position as the number one democracy in the world. Can we get that luster back? Sure we can. We need really good political leadership that knows how to project power, but can also stay humble. I think that's the big thing about it. Whether it's at a macro level with nation states or whether it's at a micro level with how I deal with my next door neighbors, right? I could be very confident in Mike Howard and proud of my background, but I'm going to make sure that I treat that neighbor with respect. I'm not going to be braggadocious. I'm going to treat them the way they want to be treated. We've done it before in the past, there's no reason why we can't do it now. I think most of the world wants to look up to the United States, and for any number of reasons. I think this world would be at a far darker place if this country had never existed and had we not engaged in the things that we've engaged in over the world to stop bad guys from doing bad things to good people. But we just have to get back to the basics of who we are as a democracy. We're not here to impose our will on people. We want to free the oppressed, kind of like the Green Beret slogan. We want to support those governments that are trying to fight against terrorism or whoever is against their democratic states. We want to do it legally, want to do it morally, and we also want to make sure that we understand their sovereignty. As long as we can do that, I think we can get back to that luster you mentioned.

KH: After your career at Microsoft, you retired, but you've stayed busy speaking and giving interviews about crisis leadership, about leading through difficult times. That's pretty well timed. What wisdom can you share with us about leading through the moment, the multiple crises we find ourselves in right now?

MH: Well, it's funny you mention that. I'm actually finished putting pen to paper to a book on leadership that hopefully will be coming out in the summer. In the process of writing that book, obviously those questions that you pose sort of come to mind. I think one of the things I remember from the different crisis situations we managed at Microsoft, or even at CIA, was that as a leader, yes, you're there to call the ball, as it were, when a critical decision is made, but you don't make it in a vacuum. And it's amazing to me how many people I've run into over the years that feel like because you're the leader, you've got to make all the decisions yourself when you've got... Hopefully you've built a capable team of subject matter experts that can say, "Hey boss, we have two choices here. A or B. We collectively looked at the data, looked at the ROI, looked at kind of pluses and minuses. We think we should go with B." And to me, if you go in and manage a crisis situation, it starts with the people that you're leading, the people that you have working underneath you. And it takes time to build up those teams to get the right people who you can trust that can give you the wise counsel, who can even tell you "boss you're wrong. You're going down a rabbit hole. We need to go this direction." If you have the right team, as you well know Ken, if you have the right team and you've treated them right and you've trained them right, in terms of how to manage crisis situations, then you're in a better position to deal with whatever's coming up ahead. It doesn't mean it won't be difficult. Doesn't mean you won't have some people burn out. As much as you try to give people some relief, some time off, I mean it is what it is. That's kind of the job. But the nucleus is that team. Without it, you're flailing away on your own. You can't make good decisions and you're probably going to make a mistake at some point.

KH: Well, thanks for sharing that, Mike. We end every episode of Burn the Boats with the same question. What is the bravest decision that you've ever been a part of?

MH: Well, this is more of a personal thing, but I didn't retire from CIA. After 22 years, I found myself in a position where I wanted to do other things. An opportunity provided itself at Microsoft. I had probably all of the colleagues working for me at the time that said, "You're making a big mistake. You're ruining your career. You're giving up your guaranteed retirement if you will only stay on for another five years or 10 years." And I knew it was risky. I didn't know anything about the private sector, but internally, you kind of get that- if it's not right, you get the little thing in the back of your neck every so often or you get something in your gut or your heart. In this particular case, it was like, no, this is the right decision to make. And it was a leap of faith. I didn't know anybody at Microsoft. I didn't know anything about that world. Ultimately it paid off and it was the best decision I ever made.

KH: Been an honor having you on Burn the Boats. I hope you come back.

MH: Thank you, Ken. I appreciate the opportunity.

KH: Thanks again to Mike Howard for joining me.

In the next episode of Burn the Boats, I’m talking to Steve Schmidt, long-time Republican strategist. Steve was a founder of the Lincoln Project, a political action committee that helped ensure the defeat of Donald Trump.

If you enjoyed today’s episode of Burn the Boats, please rate and review us on iTunes - it really helps other listeners find the show.

Thanks to our partner, VoteVets. Their mission is to give a voice to veterans on matters of national security, veterans’ care, and issues that affect the lives of those who have served. VoteVets is backed by more than 700,000 veterans, family members, and their supporters. To learn more, go to VoteVets.org.

Burn the Boats is a production of Evergreen Podcasts. Our producer is Isabel Robertson. Audio engineer is Sean Rule-Hoffman. Special thanks to Evergreen executive producers Joan Andrews, Michael DeAloia, and David Moss.

I’m Ken Harbaugh and this is Burn the Boats, a podcast about big decisions.

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