🎂 Dave Cooper & Doug Kramer Fireside Chat

Well, welcome everybody. This is Doug Kramer. I'm Cloudflare's General Counsel and continuing our series of conversations with incredibly interesting people around Cloudflare's 10th birthday.

It's my honor and privilege and I'm very excited to welcome David Cooper to a session here, a conversation that we're going to have for about half an hour about some of his very unique experiences, his reflection on those experiences, and what the rest of us might be able to glean from that, even if we're not in the exact locations doing the exact things that Dave has done throughout his career.

So Dave, welcome to Cloudflare's birthday week and thank you for taking some time with us.

Well, thanks for having me. Very good. Well, just as some background for everybody, Dave entered the military out of college in 1987, went, I think, immediately to the U .S.

Navy SEAL team, where he spent about 25 years of his career after initial deployments in support of operations Desert Shield and Desert Storm.

And starting in about 1993 or 1994, he moved over to the Naval Special Warfare Development Group and for the benefit of those of us who may not have served in the Navy.

Dave, can you give a brief description of what that group was and what it did?

Because you ended up serving there for, you know, somewhere between 15 and 20 years.

Well, yeah, the DEV group, as we call it, is one of the nation's two top counterterrorism teams.

The Army's Delta Force is the other.

We share responsibilities with Delta Force. Both units are very selective.

So to get there as a SEAL to DEV group, you spend on average about five to eight years in the SEAL teams.

You perform well. Then you, you know, you screen to get to go to DEV group and there's another selection process about seven months long and frankly about half of the SEALs that apply don't make it through.

But once you do, you are into that unit, you can stay there really, which is unique in the world of military.

You can, you know, I stayed there for 19 years.

And as I said that, you know, our job was counterterrorism, you know, anywhere on the seas and in Atlanta, of course, we were in Afghanistan and Iraq and Bosnia and Haiti and other places like that.

But yeah, that's pretty much what the team is.

Very good. And since I'm taking that you're too humble to probably say it yourself, for at least two years in there, I think from, I think it was 09 to 11, you were command master chief of that organization, which I think means you were the highest ranking SEAL or the most senior SEAL as part of that group.

Is that fair to say? The senior SEAL operator. So my boss would have been the commanding officer, but I was, you know, not too humble to say it, just that that's a political appointment.

I didn't really want the job, but I was given it for one reason or another.

Happy to serve when called upon. Well, great. And then left the service in about 2012.

Since that time, I've been doing a number of different things, sought out a specialized master's degree program in complexity psychology and sociology, which I think starts to explain why the conversation with you today is more than just, you know, sort of us being tourists and sort of talking about some of the things that you've done, but really how it has broad relevance for a lot of people.

And then most of you also worked in various consulting roles, helping people in the private sector and businesses very different from the Navy SEALs think through hard problems, figure out how to manage complex risks.

Can you talk to me a little bit about that and sort of what you have found, you know, sort of a general way, and we'll go deeper on this, but how you've been able to bring some of those tools you learned in the military into some of these advising roles?

Yeah, it's a great, great question. And I think, you know, as SEALs, we work in some of the most complex environments imaginable, right?

There's, you know, we can think of that as a complexity in its simplest form, a diverse group of actors, all interconnected.

So we can touch one another, all interdependent.

So what I do affects you, what you do affects me kind of thing, all with the ability to change and adapt.

And inside, particularly that world of combat, it's changing rather rapidly.

And, you know, how does a group that's highly adaptable, like that SEAL team or a Delta Force team, you know, how does it work?

And that was fascinating to me. I didn't necessarily have an answer for that when I got out of the military, you know, it was not random, but, you know, we were successful sometimes and other times not successful.

And I was offered this opportunity to go to Oxford and really dig deep into complexity or into complexity science or complexity theory.

There's, you know, there's no real definition for it.

It's fairly new. It's broad. And, you know, the intent was then how can I take those lessons that I learned in some of those, you know, incredibly demanding environments into the world of human beings in businesses and stuff like that.

And so that's where a lot of the psychology and social sciences came into it, right?

How do we change or help people change their behavior, embrace positive change and stuff like that.

And that's what I do these days. Good. And not to, you know, provide a spoiler alert for what your master's thesis or any sort of studies would have been about.

I guess the solution or the conclusion is probably that the world is getting more complex.

And so thinking as part of what we're trying to frame a lot of these conversations around, you know, we're doing them related to Cloudflare's 10th birthday, which we celebrated last Sunday.

And by, you know, creating a baseline of saying, okay, 10 years ago, obviously Cloudflare was a very different company.

It's three or four people working above a nail salon in Palo Alto.

Now we're in a significantly different place. You know, thinking back 10 years, what would, you know, and that would have been the last couple of years in your service just as you were starting to make the transition out.

What do you think are the most significant changes that you've seen in your world and in the areas where you operate in that last 10 year period?

What was so starkly different between the world the way it may have been back then and the way it is now?

I think your comment that we're getting more complex kind of sets this up.

And that is a, you know, in the military, we talked about this, but certainly in the business world over the last eight years, I've seen this emphasis on resiliency.

And that has changed dramatically. And our understanding of has changed, of course, in the world of complexity, you know, whether we're talking to forest or climate or your brain or your body or an organization, you know, we know what drives diversity and that's our, we know what drives resilience.

And that's this thing that we call diversity.

You know, and of course, that is a term that's familiar to us as well.

I look at that as an aspect of resilience for me, though, diversity isn't just gender diversity or racial diversity, those things are incredibly important, but it's also digging a little bit deeper, going below the surface and getting into skill diversity, educational diversity, cultural diversity, cognitive diversity, are different ways of seeing the world.

And, you know, can we integrate those different ways to come up with some really unique solutions to the problems that face us.

So that's diversity working at a number of levels, but all, you know, harkens back to this thing that we call resiliency.

Yeah, it's interesting.

During some of my tenure in government, you know, on the civilian side, resilience is one of those words that I was sort of introduced to that I hadn't sort of seen before.

And you certainly heard it used in sort of military, you know, action.

I saw it a lot also in sort of disaster response, disaster recovery.

And there seems to be more of that all the time that there's sort of, you know, resilience and recovery, this ability to deal with adversity and sort of do it that right way.

And it's a word at first, when I moved over about four years ago to private sector and working in commercial sector, you didn't hear a lot, but I think you hear all the time now.

You know, there used to be sort of risk management, which is still definitely a part of it, but resilience is a much more proactive, omnipresent sort of mindset that I think you're seeing more and more in the commercial and private sector, you know, all the time now.

I mean, do you find that as well in sort of making the transition that you've seen a lot of private companies bring over some of those rules and some of those experiences?

And what, if anything, do you think have they needed to hear or think about the most that you might have brought over from some of your previous experiences?

Well, yeah, I think one of the things that resonates with people is that, you know, coming from the SEAL teams is that we don't get it right all the time.

And I, you know, and that resiliency is about that. We understand the resiliency is about, you know, being able to absorb a shock and bounce back.

Resiliency is also to some extent about being able to reinvent ourselves or even our core business processes and stuff like that.

The amount of experimentation that an active operational SEAL team does is surprising to people.

We often think of the military and it's, you know, it's this way and it's always been this way inside of an operational SEAL team.

A lot of experimentation goes on, a lot of failure. I don't want to say a lot of failure, but in those, we try to fail obviously in a safe environment, in a training environment, because it always happened.

And we try desperately to learn from those failures, so we don't tend to punish people just because they've made a mistake or something like that.

And I think that surprises people and they tend to think that we're perfect.

That is so far from the case or from the truth, you know, and the fact is we're fallible and imperfect.

And we try and we embrace that, we learn from it and we bounce back stronger and at times reinvent ourselves when we have to, you know.

Yeah, no, and that's obviously something I think it's been well known for a while, is one of the unique sort of American, in the business world, unique American and maybe even attributed to sort of Silicon Valley, this sort of openness to failure, the openness that you can declare bankruptcy and try again or or that, you know, not everything's going to work perfectly on your first try.

The question I'd have for you there is, are there any lessons that you saw, you know, with the SEAL team when it came to training for failure and, well, I shouldn't say training for failure, that whereas on the one hand you accept failure, but you also have to train and prepare and do all these other things to make sure that then you survive and come out the other side.

How would you, you know, train in a way that allowed you to sort of have that experience of pushing the limits and maybe coming out in a slightly different way?

Any sort of tried and true methods there? Yeah, I don't know that there's any tried and true methods.

The one is to set yourself up with a challenge, right?

If it's something that's so simple, you know, people or organizations do this when they, you know, post their goals and stuff like that as well.

If it's real simple, then this notion of what is so important to us is feedback.

It becomes less effective, so we, you know, we just try and come up with something that's challenging, right?

Here's creativity at work, it's art at work, try and come up with something that's challenging, go out there and do it, and then, you know, if we're successful, that's interesting to us.

Why were we successful?

More often than not is if we're that's either not successful or it's just a suboptimal performance.

We don't want to be cavalier about failure, but why is that?

And then that's that ability for us is to be vulnerable in front of our teammates.

That's another practice of ours, you know, for the most senior guys to stand up and say, hey, mea culpa, here's what I was thinking, here's what I saw, here's the information I had, here's what I did, and here's the outcome.

And none of us wants to fail or do poorly, but as I said, that next challenge is can we get over our, you know, our human tendency to punish failures and instead go, hey, I understand what you were thinking, I understand what your intent is, there's that gap in there, let's see if we can learn from that.

And whatever the case might be, we would do it for rock climbing, to skydiving, to diving, anything like that, to driving cars, you know, anything that we could possibly frame as a challenge and go out and learn from it, we did, you know.

But if we were to, if we were to label ourselves in the SEAL teams, I think is anything, at least the most successful SEALs I know, they would label themselves as learners, that's it, nothing else.

Very good. And so when you talk about, you know, dealing with these sorts of situations, dealing with adversity, being resilient, you know, sometimes those can be, you know, small changes you're not expecting you get, you know, on some sort of operation and things aren't what the intel might have told you.

Other times they can be big changes, and I want to spend a few minutes here talking about a big change that you would have lived through, and that really is, you know, starting in 87, and serving until about 2012, right in the middle of that would have been, you know, the attacks of September 11, which, you know, I think probably exacerbated a transition that was already going on, where, you know, the role of the military, you know, operating among nation states and sort of clearly defined lines of diplomacy, sort of before that date, to after that date, a lot of focus on, you know, non nation state actors, you know, asymmetric sort of attacks and risks, without any sort of sense of, you know, embassies or communiques or things like that to announce, you know, your intentions or, you know, or any of that, like, how did you see that change taking place?

And what do you think that has meant and will continue to mean for the way that, you know, military operations are run and planned for?

Yeah, wow, that's a great question.

Yeah, in 20 words or less, if you could. You know, I think our transition to the non nation state actor is not a new thing, you know, and we have been on the side of supporting non state actors to either unseat the powers that are in charge, the difference, you know, for us, or, you know, in 9-11.

And prior to that was the non state actors, not so much trying to unseat the powers that be, but terrorize the powers that be and everybody else.

And that was new for us. And there was a little bit of, we're going to put our head in the sand, from from the first World Trade Center bombing, until the two embassy bombings in Kenya and Tanzania in 1998.

And, you know, we didn't necessarily know how to do it. And, you know, of course, the linchpin and all of this, the event that tipped us was 9-11.

And, you know, that changed a number of things, it doesn't necessarily change our goals, we still have this tendency to, you know, wherever we are to try and establish liberal democracies for a whole host of reasons.

One, we don't tend to fight liberal democracies.

Two, you know, we have the best of intentions, we want to help people out, there are, you know, other less noble intentions as well.

But the ways that we have gone about this is that transition, painfully, for some is away from the conventional military towards the use of special operations forces, and even too far, perhaps, you know, we're, there's certain things that we do well, there are certain things that we do not do well.

And, you know, at some point, we'll find the virtue of the middle ground.

I say that a lot where there's a more healthy relationship between conventional forces and special operations forces working in unique ways to solve our, you know, at least find workable solutions to some of these problems, making a liberal democracy out of Afghanistan or Iraq, probably not the solution, but there are other ones out there we could have, we might have exercised.

I hope that answers the question.

But no, I think, no, I think it touches on it really well. And within that, I might just ask a bit, you know, when it comes to that relationship between, you know, maybe more traditional military functions on the one hand, that still certainly have their need and their purpose.

And so you can't make the whole operation into one, you know, homogenous sort of system.

But you've got sort of the more traditional military on the one side, and then special operations, you know, on the other that certainly have their needs, and probably a growing need during this period.

Have you developed a feel for, you know, how you manage that or how you make that work well together when there are clearly different roles, but if groups are treated differently, or groups are given different goals and different resources and things like that can lead to, you know, tension or any of that?

Did you find, you know, in your experience, sort of best ways to manage those relationships in a productive way?

And I get a great insight there. And it's the word competition.

And we in the United States military, the United States government tend to compete with the wrong people.

In other words, we compete with ourselves, whether that's resources or, you know, status or whatever the case might be.

And that holds us back.

Best practices for us was to just to act as though the conventional forces usually are the what we would call the battle space owners, let's just say Jalalabad in Afghanistan was owned by conventional forces, we treated them as friends, as equals, you know, as fellow Romans, or whatever the case might be.

We were sensitive to their concerns. And it's, you know, it's this is an example for organizations as well.

A lot of progress is made simply by sitting down and talking to the to the other side.

And that the more you talk, the more you start to understand people, the more you can say, hey, we can, you know, we used to, it was frightening to conventional battle space owners that we would out be out there doing operations at night.

They thought that no real evidence to back this up, but they would think that, hey, you know, your offensive operations are going to do more harm than good, and they could have.

And we would do those, we would gather the evidence and say, hey, here's, you know, here's what happened.

And, you know, here's what we learned from it.

And that gives them a sense that, hey, these guys are, are just like us, they're well intentioned, they have skills that we don't have, and we could leverage those skills.

And those relationships take a long time to build.

The irony is that if you're going to be in a place like Afghanistan, and you're trying to build relationships over a long period of time, that period of time where you, you know, we are so different from the Afghan population, this is an immunology problem, right?

You know, if I poke you with a splinter, bacteria gets in you a bacterium, that bacterium has a limited amount of time before it's recognized as foreign, and your body wants it out.

Well, countries are no different.

So all that time we're trying to build relationships with conventional forces, we are also harming that relationship with the Afghan civilians.

So it's, there's this dynamic interplay there, where we should have done this long before we got into Afghanistan.

I think that's a big lesson learned. I'm not even sure it's been remedied, but...

Sort of resiliency and balance, sort of in all things, you know, it's never going to be easy.

So, well, let's talk a little bit about, you know, big, large organizations, because I think that's something that you and I had talked about in preparation for this that I found interesting, and I think also is a lot of appeal to your transition sort of from military to private sector work.

So, you know, the U.S. military, you know, by all measures, I think, almost all measures, you know, the largest organization in the history of the world, and operates in some unique ways.

I think I shared with you at one point talking to Richard Danzig, former Secretary of the Navy, had sort of said one of his goals, even though he came very much from a legal professor point of view when he went to Washington in the 70s, was to figure out how that organization worked from sort of a management and operations point of view.

So, you know, what did... And let's start on the benefits side of it.

So, what did your career in the military teach you about the benefits of large organizations that you see other organizations struggle with or may not have at their disposal?

What are sort of the advantages of being in a large organization like that?

Well, there's a cohesiveness, particularly in special operations.

I can't speak to the conventional forces, but there is a cohesiveness that goes on inside of a special operations unit that we can all benefit from.

And that is really simple. It's time spent together and it's shared experiences.

And that really leads to the strength of what we would call culture. I think that is, you know, something we can all take away from that.

It's not anything that's designed or engineered, but we spend a lot of time together and we share a lot of experiences together.

And by virtue of those two simple facts, we tend to grow very close to one another, even though we are very diverse, right?

We are every political persuasion you can think of, we're every religion you can think of, to include atheists and agnostics, we're every color from, you know, as I always say, from lily white to cold black, the true minority in the SEAL team is the orange self-tanner.

There's occasionally one or two of those thrown in. So, we have all of this diversity in there, but we tend to grow very, you know, those relationships between guys on a SEAL team are nuclear in their strength, they're nuclear bonds.

So, I think that's important. There's a lot that we could talk about on the negative side as well.

So, let me pivot there now. So, when it comes to the challenges of being in a large organization and what particularly you as sort of the more flexible, you know, side of it in special operations, you know, run up against, what are the challenges of, you know, what might be viewed as stability and resources and you're walking into something that's sort of set up and established, whether it's in the military or in a company, a large established company, what were some of the downsides that over time you identified may not have had the benefits that people thought they did, but might have just survived from momentum or inertia or whatever?

What were the most significant challenges that you experienced?

So, for the military, specifically, the biggest drawback to the United States military is that it's not just a class system, it's a caste system.

And the doctrine and the dogma or the dogmatic doctrine is set up to keep the classes or the castes distinct, which is unfortunate.

Inside of an operational SEAL team, we just did not acknowledge rank or anything like that.

It was as egalitarian as any Enlightenment philosopher could imagine.

Outside of that, though, the United States military is a rigid class system, and as some have said, even a caste system.

And that, you know, is strict regimentation. So rules, strict rules regarding behavior, there are strict rules and regulations regarding how relationships can exist between people, how roles are performed.

And that stuff has not changed since the inception of our military.

We have some, you know, some superficial changes in technology and stuff like that.

But the ways that people think and act and behave and relate to one another, that hasn't changed in centuries, and that holds us back.

And so that amounts to a lack of adaptability. You know, the military is great at, you know, energizing a large group of people to move in a certain direction.

Now, whether that direction is the right direction or not, you know, it's not open to feedback.

And because it's not, you know, everything is top-down driven, it is not adaptable.

So, you know, I always use the military as a, you know, the military says that, hey, we're not a business.

Now, it's a platitude.

It's a way to kind of quell the cognitive dissonance, right? We're the most technologically advanced military in the world.

We tend to lose to people who have no technology, or we end up suing for peace.

So I use that as an example. I don't be like the United States military.

But for any of us large organizations, we're all constrained by a good professor at Oxford, Robin Dunbar.

Dunbar's number, you know, relationships.

We can manage cognitively about 150. Most people can hang on to or manage really effectively five or so, a handful of really important relationships.

Well, it's the relationships inside of an organization that make that organization.

And the challenge as you grow is to figure out ways to continue to manage those relationships in ways that allow the, not just the people to thrive, but, you know, with the whole being, the whole being greater than the sum of its parts, allowing the organization to continue to thrive, to be sustainable and stuff like that.

And that's, that's a big challenge. So I'm going to ask you in a minute, you know, about managing or trying to affect change in large organization, which I think is where you're going and, and, and what your experience certainly has been in dealing with special operations.

But going back from it to a large organization, you know, some people would say from a management point of view, you know, listen, you have to have this sort of structure.

You have to have, you have to know that when you direct people to go do this, it's going to get done.

And you don't have a bunch of individual operators who are second guessing and saying, you know, I'm not going to respect that person just because some org chart tells me to, I'm going to do my own thing over here.

And obviously that, that, that leads to chaos.

Is there any way though, that you have ever, and again, this is sort of asking an ultimate question.

So take this whichever way you want to determine how to figure out when that sort of purpose has reached the end of its effective life.

And it really just does become people resting on the org chart, not to get things done, but to fulfill their own ego or, or, or whatever, you know, is, is there a way, because certainly there's some purpose in that, but as in all things, it's sort of, I think, trying to figure out where you start to bump up again, the, against the end of its usefulness there.

And, and so maybe then I will turn this in the next sentence, as you were sort of pushing back against that to create additional flexibility, optionality, optimization of any sort of, you know, you know, anything you were planning, did you ever sort of figure out how to separate the wheat from chaff on all of that when it came to large organizations and the part that might've been most susceptible to change?

Yeah. Context matters.

So even if I were to have figured it out right at one specific point in time inside of the development group, it would change if you, if you change the context.

But you know, I think there's, there is a dynamic balance. That means that equilibrium is going to shift.

And that, that comes between, you know, inviting all the feedback and all the ideas, inviting all the stories.

This is the dialogue and the conversations, formal and informal, informal dialogue and conversation were really important to us.

This is the after work stuff, or the, you know, we let the hair down, if you will, we take the, the rank and stuff off.

There's a balance between that level of, of, of conversation and that's the sense -making piece and, and then actually deciding and enacting.

But we would, you know, we went forth with a way that we looked at everything as provisional, not the way the United States military necessarily does.

Like an order is an order.

It is not provisional and you can't change. We would say, Hey, our decisions and our actions are provisional.

And if, you know, if we went left, let's say the team is, you know, we're going to go this direction over here.

And we find out from the feedback, because we're open to that, even the tough stuff that we made the wrong decision, we'll change course.

It's again, we're not hung up on this status. Our, our self-worth is not tied to getting it wrong.

Our self-worth is tied to learning.

And I think that's a, it's a, it's a massive difference between just, you know, a large organization that recognizes that strategy is provisional, decisions are provisional, actions are provisional.

We're not going to be perfect in complex environments.

There are no elegant solutions. There are workable solutions that we stick with until we find a better workable solution.

And at all times, we're open to this feedback.

We're tolerant of different points of view and different ideas.

And in fact, it's this diversity of ideas again, that are going to help us.

And the other thing we do is we recognize that with that diversity comes conflict and we're open to the conflict as well.

And we don't, we don't run from it as painful as conflict is.

No, that's a really good insight. I mean, I think the more organizations are so afraid of failure, I think the more they retreat into process and, and structure and titles and cast systems, you know, and so I think teasing that out that when you pull on the ability, the willingness to fail, I think you open up a lot of flexibility in the joints on a system.

That strikes me. So we have just a couple of minutes left.

I want to give you at least a second or two, because you've mentioned, you know, Cloudflare is a technical company.

A lot of our audience here would be very technical.

You made mentioned before on the one hand, how use of technology by the military on the one hand might be a little bit superficial on the other, that use of it by the American government, usually far outstrips some of our enemies and not always to our clear advantage.

So going forward for the next 10 years or so, do you sort of see, do you think there's, we're relying too much on technology and not the core, you know, sort of operational pieces?

Do you think that there are ways that the military could be using technology better?

Any thoughts that you, you know, thoughts that you have on that?

I think the way I look at these days, I look at three areas, and there's no clear cut distinction between these areas, but you have technology.

You have this relationship between technology, between the ways we use that technology or techniques, let's call it, and between our behaviors, the things that we do on a daily basis, from how we frame threats and opportunities to what we eat for breakfast.

And when we tend too far towards one extreme or the other, some people completely process-driven, right?

My nurse, what my nurse, my wife has started as a nurse, incredibly process -driven.

She is my nurse, but maybe too much.

It's good to have. But, you know, and the technology side, I saw this in the SEAL team, some funny stories about it, you know, guys with, you know, night vision goggles gave us the, the, you know, allowed us to see at night, totally enhances our performance, right?

But for some people, that bit of technology didn't just allow them to see at night, it made them think they were invisible at night, which is not the case.

And that can be very dangerous, right? I know there are funny stories, the GPS, the global positioning system, right, allows us, me to go to any precise spot on the planet.

But, you know, there are younger SEALs that have lost the capability to use a map and read the terrain and stuff like that.

So we have to, again, that balance shifts around.

And when we go too far towards, you know, one or the other technology techniques and behaviors, we lose that thing called resilience.

And we, I think we've, we've just come full circle with that word.

But it's just one of the things to be careful of, you know, we can't always want to push the easy button.

And the easy button is technology and process. Sometimes it's, you know, the behaviors, and that's sometimes the uncomfortable, like conflict and stuff like that.

Well, we have just less than 30 seconds here. And in this virtual world, doing these sort of conversations, we don't get the benefit of the sort of red, yellow, green light below us.

I just want to take a second, I mean, to thank, not only thank you for your service, but thank you for spending time with us here today.

I think the way you have tried to bridge your experience and a lot of what we're going through in the private sector has been really, really helpful and insightful.

And with that, I think I ate up most of the rest of our time, but just want to say thank you to you for your time with all of us today.

My pleasure.