Gwen Cooper: What I Learned in Business After Becoming an Accidental CIA Spy

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Gwen Cooper. How are you doing? Thanks for joining learning from others. Great. Thank you. Thanks for having me. What’s going on in California. I miss my California trips. Well, it’s, you know, even with a sheltering in place, I gotta say it’s pretty great. Yeah. I don’t mind that. Yeah. Usually I’ve talked on, on the podcast before about how I like to go to day trips.

I’m in salt Lake city, Utah. So it’s only about 90 minutes. And so I’ll catch a 6:00 AM flight there and hang out at the beach for six or seven hours and then come back the same night. So, um, a few months. Yeah, but it’s the Homeland show is for so many. So reason you’d come for a day. Yeah, yeah, yeah. I don’t blame you.

Yeah. Well, cool. So you have an interesting background. Um, you’ve worked in international intelligence as a Sila. See if I pronounce this right. CIA directorate of operations. Is that correct? I worked in the CIA director of operations as a CIA officer. And then you’ve take, I want to dig in more into that.

Um, but just to kind of give our listeners and understanding of, you know, what you do nowadays, I’ll, I’ll, I’ll run down my usual two questions. So question number one is what are you good at? What’s your area of expertise and what are we going to learn from you today? Yeah, I’m all about a leadership growth.

So how do we get leaders to the next level? And I have a background in leadership, coaching and organizational development and teamwork. So I look at developing leaders from those three lenses. It’s like, how do you develop the individual? How do you develop the team in the group? And then how do you do that?

Within North sensational context? Perfect. All right. And then of course we all are not so good at something. What is your thing? Uh, I have no inherent sense of direction. Yeah. Ever. It’s just so annoying. Other people, they could just shift naps in their mind and I’m like physically, you know, back in the day, or even with my it’s like, It’s just so annoying, especially working in the CIA.

Yeah. That’s funny, you know, you know what I didn’t realize until I, um, you know, I’ve known it for a while, but you know, before I started traveling a lot in my early twenties, um, I didn’t realize so being in Utah, I didn’t realize how beneficial the mountain ranges are to your Cardinal direction as a guide.

And then, and then I go to Florida and you just look in any direction and there’s nothing it’s just all flat and like, which I don’t know which way is where. Exactly. I grew up in the Midwest and everything’s flat just like, they’re like, Oh, it’s Northwest. What do you know? What are you referencing?

All right. Well, let’s kind of work our way, um, from the back, you know, your backstory into, to where you’re at now. Um, CIA obviously sounds super sexy and, you know, Dramatic. And so it is, it is, it is, is it as stereotypical as it sounds it had its moments? Definitely. And then there were days where it was just sitting in the cubicle typing stuffs.

Yeah. All right. So what did you do there? I entered directly into the director of operations, which is the clandestine wing of the CIA and I became a. What they call it? Uh, uh, C M Oh, so it’s also a reports officer and that person is a collection management officer. That person is responsible for receiving raw intelligence from the officers who gathered it.

We take the information and we assess the validity of it. We kind of look at where did this come from? Do we know the person this came from what’s there? Background, what’s their intention for sharing it. What’s their access to this information. So we really look at the validity of it from a lot of different angles.

Even if we deem it appropriate, we send it forward. We clean it up and send it forward. Um, because our part of our job is also to hide their identity. Certainly information and we send it on to our consumers and consumers who are different government agencies, the U S government agencies, not foreign. Um, and one of the, what are the big consumers was, is can be, uh, the president of the United States.

Yeah. So it’s interesting that you say, you know, we check the validity and who is this person in Western tent. So, so who, who just sends stuff to the CIA? Like, if I got a tip, like, I don’t like that doesn’t sound like something that I could just do. Like who, where do these people? Yeah. Well, that’s a great question.

Uh, so some of them are targeted. Some of our assets are people who are targeted and developed over time because. Of our understanding of what access they have. Some people, like you said, they can be, walk-ins some people just walk into a us embassy somewhere and say, I have this information. I want to share it.

So it sounds like for the most part though, you’ve had some touch point with them in some way before though. Generally speaking. Yes. But some of the most amazing information has come from walk-ins. Yeah. So what kind of background gets you into position like that? Let’s go back further than that. Uh, so I’m right now I’m writing a book about my experience and it’s me.

Yeah. It’s, it’s, it’s overdue and I’m excited about it, but it’s connecting. Lessons learned from the field of human intelligence, with leadership development that it’s, it’s, uh, it’s pulling from my experiences and other colleagues experiences. So to answer your question, my, my first chapter is about how I got into the agency and it’s called the accidental spy because they didn’t grow up thinking.

About espionage or reading spy novels or any of that? I was actually overseas. I was living and working in Amman Jordan and I was working for us aid USA ID. And I was teaching business communications, two adults in Amman, Jordan, and I got to no people at the us embassy there. And I got to know them pretty well.

And finally, one of them said, you know what? I do. I actually worked for the CIA. Yeah, by the way. And so that was my entry. And I said, and I thought that has literally never crossed my mind. My path was fairly unusual. I think a lot of people are interested in it. They studied political science, they study a lot of different things, but they’re, they’re preparing for that overseas life.

They. They learn languages. I knew French at the time, but there are more targeted languages that are of interest to the agency now. Yeah. What was your immediate reaction to the opportunity? When the person said like, Hey, there might, there might be something here that we can do together. I like God risk taking.

I like novelty. I like challenges. Check, check, check, check, travel. I like putting myself into situations where I don’t know what I’m doing and I have a lot to learn. And. Yeah, they checked all the boxes, honestly. Yeah. How, how do you like, um, how do you like write in the book? The reason I ask is, is I just finished one and, uh, just was finally published, um, about a week and a half ago.

And so I’ve, I’ve been in your shoes and it seems like the majority of the people that I asked that I wrote book, um, while they’re in, it are not big fans of the process. Yeah. It’s all the feelings. I mean, it’s, it’s a lot of enthusiasm and firstly. Yeah, I’m going to do this and then, then you’re in it.

Like, um, yeah, it’s all the feelings. I mean, I equate it to going through school, you know, it’s like college exams and so, um, I think what’s helping me a lot is that it’s not just about me writing. It’s more social because I’m really interacting with a lot of folks that I’ve known well and where we can, and I’m getting stories from them.

So that’s helping to believe me and, and encourage me folks on it. Cause otherwise I think the ice, the isolation of it just here, right. A book would be. A tougher slog for me, who who’s the ideal reader? Is this like a guide book or is this a story? Yeah, both. Um, so it’s, it’s lessons learned and I DIA’s of, of things to take back as individuals like individuals, like at the manager level and people helping to develop manager development programs.

It’s that. Moving from individual contributor to leader, to manager and leader. Um, so it’s the target audience and are leaders themselves, and they’re also people helping to develop leaders. And so they are stories, but I’m also leaving in frameworks and ways to think about how to develop oneself as we tell the stories, who’s the story, but, so what, here’s a story, but.

And we’re all humans. And so many of the issues from. Our stories. It’s all about human intelligence. So we’re all people, we’re all people interacting with people in some cases in extraordinary environments, but it’s still about how, what lessons do we take from that? Yeah. Okay. So, so now you take all this experience and now you’re doing your own consulting.

How did you transition out of the CIA and into your own thing? So because I had the experience variance with learning and development prior to the agency, after I was a reports officer, I thought, how can I, that that was great. And that was interesting. And I enjoyed it, but I also wanted to take the skills that I had about development and leadership development and, and help help the agency with that because I’d been through a lot of training.

Lots of, I mean, they give us lots of training, which is fantastic. And I also saw the opportunities to improve that and also improve how it met the needs of people in the field. And so, yeah. I moved into a position in one of the client destined training centers. And I started to see the organizational need.

We had to bring some of the training into at that point, the 20th century. Um, but also the 21st, when, well, I was there during nine 11. So after nine 11, so much too changed about the way that we needed to be operating and so much changed in the world around security environments and the, the training and the preparation for officers to face those needs was still a gap.

So I helped conduct the first research project into identifying what are these new security environments? What do they look like? How do we identify them? And then what are some ways to bridge the gaps in training our officers and preparing our officers for those environments? So that was a, a huge, uh, research project and also just a big, Mmm.

That’s the word I want to use. It was a real confirmation. It was a real confirmation of the work I would end up doing around the individual team and the organization. And so then after that I went into consulting cause there was really no career path for that. That was a huge contribution I was able to make.

And I felt like here’s the, here’s the best of me and what I can give back to the agency, but there was no career path. So then after that, it made sense to go into consulting. So I worked in change consulting, learning, and development consulting for small firms. And then I’ve also worked most recently at a price Waterhouse.

Coopers is one of their. Coaching leadership, coaching coaches in their leadership coaching center of excellence. And earlier you mentioned three lenses of development. Let’s kind of go back and elaborate on that a little bit there. Um, so are you referring to the individual team and the organization?

Yeah. So what I have seen in my experience, this is supported by a lot of research in and Robert Keegan being one of them is an adult developmental psychologist out of Harvard, looking at a developmental organization or a growth organization versus what was the learning organization. So learning organizations, relevant teaming and collaboration.

Great things. Big fan. It was also about, um, development and big focus was on development in organizations of high potentials. It’s like great. But there was a lot of development of other people that that would go on unattended to. And so that was, that’s a real loss for an organization because perhaps potentials are being defined is very limiting, limiting.

To the individuals limiting to the organization. So the developmental organization is looking at growth organization is looking at what are everybody’s strengths and what are everybody’s areas of development. And how do we create a safe, psychologically safe organization that allows everybody to be themselves and allows everybody to acknowledge that it’s not always about constant performance, but it’s about development.

And how do we look at individuals and teams as. Opportunities to develop and create a growth opportunity, not an, a growth organization, not an organization where it’s all about performance and you have to hide your weaknesses for fear that someone finds out. God forbid, someone find out I can’t read a map properly.

I can kinda relate to that because I’m actually hiring some more team members right now. And one thing that I’ve always focused on is when I go through qualifying the talent is I like to. Ask them directly. Okay. You know, obviously what are you good at? But then I ask them, ask them, what do you like to do?

Because what you like to do may be very different than what you are good at. Maybe you don’t like doing that thing that you’re good at. So is that kind of a concept that you apply or you experienced that as well? Absolutely. Because right there, you’re talking about, I mean, I love that question because right there, you’re talking about growth.

It’s like, what are you good at? Well, this is what I’ve already kind of achieved. And I’m really good at it. And there are other opportunities to grow. I mean, in some ways the person who says I’m good at this, and I only want to do this and I just want to stay here. That’s a little bit of a red flag. Yeah.

 

and I want to grow into this area as well. It. Yeah, it’s interesting. Sometimes I get a little kind of like you’re implying, I get a little nervous or not nervous, but sometimes it’s interesting to see the light bulb go off when you ask them and they go, wait, I can do something else. Yeah. Right. I’ve never, yeah.

Maybe sometimes people haven’t even entertained it or it’s just this subconscious thing that, well, I have to make. Money. And it will be all have to make money, but I have to make money. And, and it’s a false narrative around, I have to stay in this lane to do it. And it, it’s not necessarily beneficial to the individual, nor is it beneficial at times to the organization?

Yeah, exactly. All right. Off, off topic question or our listeners, can’t see what’s going on, but you got all these PostIt notes in the back. Tell me about that. Ah, I like it. So that’s like how you’re organizing things. Yeah. Yeah. I have a big, a glass board behind me and I have posted notes, IDEO design thinking style.

Um, yeah, those are the chapters. It was just, it was so helpful for me to visually put it on my wall versus new document. Cause I just need to see it all the time. Yeah, I can move things around. Cause I’m also working with other people who are submitting stories and so I can move things around. Yeah.

That’s like finder to get back to work. Yeah. It’s like a, it’s like an analog version of Trello. Are you familiar? You use Joe I’m kicking it. It works for me. Yeah, well, I didn’t close. And then I walk away when I was doing my book, I’d have to do something similar. I would, you know, make the edits on the digital copy, but then when I’d have to want to have to prove it, I’d print it and then I’d scribble on it and then I’d go back and re input it because it’s just something about, you know, seeing it, like you said, and, and.

You know, rearranging chapters and like in a physical touchable format. Yeah. I couldn’t agree more. And I have a, I have a writing coach who’s helping me as well, which I find a really inspiring part of the process and also the accountant from an accountability perspective. Cause I have to know, I promise that I’m going to have X.

Chapters or whatever done by a certain date. Is it, was that part of your process? Um, so at the beginning I worked with the lady that helped me just for a little bit. Um, and so what I did is I just vomited on her and then I said, here, the things I want to talk about, can you clean up that mess? And then she kind of said, all right, I think this is kind of the structure that you can follow.

And then I took it from there because you know, my things. SEO. And so it’s like super technical. And so it’s not necessarily something I can just have translated into like a, uh, you know, somebody from a non SEO background, but it definitely did help a ton. And the, the, the writing process in general was interesting.

It was a total new learning experience. And during it, it’s just, like you said, at first, you’re like, this is exciting. And then you get a little bit into it and you’re like, I’m really tired. And then, and then, uh, I probably would hesitate if somebody asked me if I would do another one. While I was doing it, but then now that I’ve recovered a little bit, I’m like, yeah, that was cool.

Maybe, maybe later, let me recover a little. But she, you know, she, when she started out with me, she asked exactly what you were asking from the very beginning from a marketing perspective is whose, okay, so you want to write a book, who’s your ideal paying client. It’s going to pay for it. And I thought that was.

That was a really good starting prototype. It was already so bogged down with all these ideas and I want to share them. It’s like with anybody in particular. Yeah. Cause you get stuck in your own. Yeah. You get stuck in your mindset as, as an expert. And then, uh, you know, you’re in your own little bubble and you don’t realize that you need to translate that because nobody else is at your level.

Yeah. Yeah, exactly. And I think that was just something I. I think it’s just so important for anybody or any businesses con constantly, whenever I’m making a decision about things, it’s like my ideal paying client, they care about this. I find it interesting, but yeah. You know what I find it. Interesting.

What’s the point? My it’s funny you say that because when I mentioned earlier, by my little day trips, right? Where I go ahead to California for a couple of hours, that’s why I like it. Cause I get there and like, nobody gives a damn about SEL right now. I collect them. Like, I guess there’s more to life.

Like there’s somebody on the beach doing nothing. I should do that. Yeah. Yeah, yeah. Definitely with the white writing process as well. Like I know there are some people with like, Oh, you should do a little every day. Now. There are just some days I can’t. Yeah. I get tired of myself. I mean, I’m so sick of myself.

I think that’s healthy. Yeah. Yeah. Well, one thing you talked about offline was helping people find a, you know, manage the end. You put it kind of in quotes the gray in their lives. So what, what is the gray that we’re dealing with? Yeah, so. There’s so much uncertainty in life. And I think now with the pandemic, that’s really come to the fore.

There’s so much that we can’t anticipate fully and we can try and I think. There’s so much when it, when people move up in leadership levels, it becomes more and more about that, about being comfortable with complexity and uncertainty and making the best decisions you can when you don’t have complete information.

And I find a lot of leaders struggle to acknowledge that. That is the reality. And that’s a lot of the gray and that’s a lot of the gray that came from working in the agency. I mean, there were a lot of preparations. We get a lot of intelligence, but it’s always imperfect and we do the best we can and we plan things and we hope that they go to plan, but we always have to be ready for it to go sideways and be ready to pivot.

Did you have like that one guy that everybody in the CIA was like, Oh, this guy is coming forward again. Like the, did you just have like the repeat customers that just regular app? I mean, we have regular assets, so yeah. I mean, I’d say there were some assets that, yeah, it could be in an organization though.

A little challenging to handle a little hard to. Manage, they can get information, but they. They didn’t like to be controlled. They don’t even like the perception of it. So yeah. Those people. Yeah. So when, when you work with these leaders nowadays, um, you talking about how leaders come to find out, that’s just the way it is that some things you don’t have all the right answers for, and, and as you talk to different leaders or help them grow, is there like an X factor that you see in some leaders?

Is there some that are. Born with it and others need, you know, more grooming and education. Uh, I think, yeah, I think there are, there are definitely personalities, styles and values that play into the ability to, to embrace ambiguity and flexibility more than others. Um, But I also say that it’s moving from like an individual contributor to a leader it’s also really digging into self-awareness and that is the biggest piece to me is, is providing opportunities for people to become self aware and understand their own motivations.

And what’s driving them. So for example, with a lot of coaching clients I work with in particular and, um, manager development programs, we tend to start out with just values. Like what are your own individual values? Because for people to actually. Come up with like, what are your top three values? What are they, how do you define it?

Is there are a lot of instruments that, where it comes defined. I don’t care about that. I don’t care how somebody who wrote a psychometric test defines it. I want to know how that individual defines it. That is what’s driving behaviors and mindsets. And so quite often it’s. It’s the way we define the world, that’s driving our actions.

And so there are opportunities for people to grow and. And expand on those definitions that will then in turn, change behaviors and mindsets, the, the concept of, you know, what are your values at face value? That sounds like the most simple question. And then the more I sit here, that’s an impossible question to answer.

It’s probably, you probably have some, so many people that are just, they just hit a wall. Like it’s, it’s there, but how do you get it out and how you verbalize that? And that process is huge. So a lot of people I’d say going back to your initial question, a lot of people can get really stuck on the ability to think in terms of Gregg because black and white is so comfortable in that that can tie to values around justice or equality.

And it’s like, this is how it should be. It’s either right or wrong. It’s like, well, There are times where things are a little bit right. And a little bit wrong. And I’m not saying that we’ll need to shift their integrity at all, but it’s just, it’s exploding. Those does yeah. Analogies for people and what they think of them.

And then how do you make decisions based on those things? When things aren’t so black and white, and I see a lot of we’ll go from individual contributor where. Everything can be pretty straightforward. Like here’s my performance. Here are the expectations. I met all of these expectations and not I’m a high potential and then great.

You’re, you’re great at what you do now. We want you to become a manager. Totally different. Yeah. Well fighting with each other. You’ve got people doing things that are very much in the grade that have to be addressed and it’s. Very challenging for them. I think those soft skills are the wild card that are so important, but our little, you know, you can’t put those on paper.

Like you have to be able to do those things. You talked about being able to negotiate and discuss and, and, you know, be the middle person between others. Yeah. And so part of what I’m writing the book is what are some of these circumstances that people faced in the field, uh, in, in the agency. And highlight a lot of that gray, but then it’s also very relatable.

It means a high stakes, exciting thing to read about, but the interaction between people is very relatable. Yeah. Well, so what’s it like when you work with people, where do you start? What’s day one. If I’m working with, uh, an individual one on one a day, one in coaching, it’s all about the individual driving the agenda.

Like I can’t tell somebody else what they need. It’s the ethics of coaching is that they come to me and start talking about some of their goals and then I help them. I ask questions and help to flesh that out. So a lot of the process is helping me is. Is allowing me to help the person develop self awareness around what the issue actually is separating root cause from symptoms.

And then also helping them identify what are the things that you need to do to get from this point to this point. And so that’s where a lot of the adult development, uh, comes into play. Um, a lot of the growth, like what is a, a mindset that might be limiting them. What really matters to them. That’s why we work on values.

Because a lot of people get stuck on trying something new because they think it conflicts with their values. And so we look at, does that actually conflict? In what way does that conflict with your values? Is that, is that the reality? Is that a story you’re telling yourself? So it’s, it’s a lot of that self awareness and finding new ways to look at things, allow people to try new behaviors and grow into the goals.

It sounds like how I talk to my kids just similar. Um, except when we’re working with adults, it’s, it’s the idea like adults actually know what they need. They ha they know what they need, and it’s just like, I’m helping make it easier to get there. Yeah. They think they know, but yeah. Yeah. Just exposing them to it.

Yeah. Well, it’s super cool. Um, Gwen, I appreciate your time. This has been a fun chat. I want to give you the last few moments to share your contact information or let us know how we can find out more about you. Great. Thank you so much. Really enjoyed it. Yeah. Do you have any, uh, I have coopersolutionsllc.com.

Is that the best place for people to find more? Okay. Gwen Cooper, Cooper solutions. Thanks so much for your time. Thank you. Thanks, David.