This podcast features Carmen Medina, Heretic at Rebels at Work, and her presentation, “Lead Above Mediocre Thinking” from the design leadership conference Prototypes, Process & Play on August 10th, 2017.

Prototypes, Process & Play presentation podcasts are sponsored by Balsamiq – with Balsamiq Mockups, anyone can design great software.

Carmen Medina – Presentation

Heretic, Rebels at Work

Carmen, a retired Senior Federal Executive with 32 years’ experience in the Intelligence Community, is a recognized national and international expert on intelligence analysis, strategic thinking, diversity of thought, and innovation and intrapreneurs in the public sector. She is the co-author of the new book: Rebels At Work: A Handbook for Leading Change from Within and of the landmark Deloitte University Press paper on Diversity’s New Fronter: Diversity of Thought and the Future of the Workplace. Her story as a heretic and change agent at CIA is featured in Wharton School professor Adam Grant’s new bestseller Originals: How Non-Conformists Move the World.

From 2005-2007 Carmen was part of the executive team that led the CIA’s Analysis Directorate; in her last assignment before retiring she oversaw the CIA’s Lessons Learned program and led the Agency’s first effort to address the challenges posed by social networks, digital ubiquity, and the emerging culture of collaboration. She was a leader on diversity issues at the CIA, serving on equity boards at all organizational levels and across Directorates. She was the first CIA executive to conceptualize many IT applications now used by analysts, including online production, collaborative tools, and Intellipedia, a project she personally green-lighted; as a senior executive, she began using in 2005 social networking and blogs to reach her diverse workforce. Upon her retirement from CIA, she received the Distinguished Career Intelligence Medal. From 2011—2015, Carmen was a member of Deloitte Federal Consulting where she served as senior advisor and mentor to Deloitte’s flagship innovation program, GovLab.

Carmen describes herself as Puerto Rican by birth and Texan by nationality. She likes to garden and cook things that she has grown. For more, keep up with Carmen at rebelsatwork.com or on Twitter as @milouness.

Lead Above Mediocre Thinking

When we engage in design thinking for our teams and projects, it’s easy to emphasize Design over the Thinking. Leaders know that we need to slow down to speed up; plan and think more to prevent rework and waste. Sometimes, we invest more in the work and the artifacts over finding the right ways to work together and create a shared understanding before moving toward a goal. Carmen Medina spent her entire career working with a diverse set of people and she had to find ways to create a shared space for collaboration–and she’ll show you how to focus on HOW teams work over WHAT the work is that’s being done.

All of this, regardless of whether or not you have a security clearance!

Presentation Transcript

Please note:

Podcast transcript below.​ Please note: Transcription was recorded live; there may be errors (typographical and contextual), as well as omissions or other content gaffes.

​Additionally,​ there was microphone feedback that happened in the room from time to time, and we did our best to minimize it in the podcasts. We apologize for any disruptions to your listening experience that this may cause.

Carmen Medina:

Perfect. Thanks, Russ for having me here. I’m not from the design world. But I’m here to talk to you about some of the lessons I learned about getting an individual as thinking better and getting the teams to think better.

So first I’m going to talk a little bit about myself since that’s my favorite topic. I’m Puerto Rican. Any Puerto Ricans in the room? No. I was giving a video conference to a German audience in Austria. And I asked if there were any Puerto Ricans in the room.

[Laughter]

I love this photo. I think my mom was in her early 30s then. It’s a very famous beach in Puerto Rico. Anyone know it? Mocio Beach. I did work at the CIA. I started in 1978 and retired in 2010. I was an analyst and a manager analyst. And what we do is we try to make sense of the order and provide advice to our executive. We try to reduce uncertainty for our policymakers, war fighters, trying to navigate and protect the U.S. in this kind of interesting world.

This is a picture of me at the top of either one of two countries. Which country am I in? This isn’t hard. Okay, it’s obviously a country where I need to wear a flap jacket. What country am I in?

Audience:

Afghanistan!

Carmen Medina:

Afghanistan! Thank you. Those two guys were my handlers. My security people. Yes, indeed that is a CIA plane. And these guys, they stayed with me the whole trip. So I was like a senior leader type. So, you know, I would visit and make people feel happy that the important person came. Yada‑yada‑yada.

[Laughter]

Reality right? And then we would drive around in cars. Armored GMC suburbans. These guys, I never knew their real names. They had code names like Grumpy, something like. That these are all true stories by the way. They say no matter what happens outside stay in the Suburban, in the armored vehicle, unless we say “Get out, get out” and then you must get out as quickly as possible, which is an impossibility. Because if you have ever tried to open the door of an armored GMC Suburban, for me it was literally not possible. I could not get enough heft into the opening.

If you’re interesting, I’ll tell you more. But I’ll tell you a little bit about my CIA experience. I describe myself as being a heretic at the CIA. I realized in the late 1980s there was something really wrong with the CIA’s business model. I just had this idea that how we were doing things was not – and I’m not going to have you guess the things. But I will tell you that most of my story as a heretic at the CIA involved trying to convince the CIA that the internet was going to be really important.

[Laughter]

And this is true! Gospel truth! In the 1990s, I would say the internet is going to be really important. It’s going to change the way all organizations involved in knowledge do their business. And they thought I was a heretic. And I will just take a minute to say this. When you’re trying to make a big change in an organization, which I guess designers often get involved in, it’s very difficult if you try to make what I call a theological change. So the internet, of course, is about open information, making it accessible to everyone. And what was the CIA about? The opposite! Closed information, keeping secrets. So when I made the argument that the internet was going to really be the most important thing in our lifetimes, I might as well have been Martin Luther nailing the letters up on the door at the church, for those of you who get that reference.

Anyway, that is my history as a heretic at the CIA. And I spoke about that in 2010 as I retired. There was The Business Innovation Factory.

[Cheering]

Yeah, someone! I’m speaking there again this fall. And someone heard me speak at this conference, my co‑writer. And I talked about being a heretic at the CIA. And she said why doesn’t anybody help rebels at work. That’s her phrase. That’s the copy of the book.

Let me get to the presentation. So as an analyst, I spent a lot of time trying to be a good trainer. And the issue that I had the most expertise on and I worked on the most was South Africa. And in the 1980s, you could say that South Africa had a design problem. They had this very badly designed system called apartheid. And there were all sorts of issues with it. The whites in South Africa didn’t really understand how their society was going to evolve and they created a mess for themselves.

I was an analyst on South Africa and I was the chief of the South African team in the mid‑80s. I must say that shortly after this period in my career I became a more senior manager, became less interested in the substance of any particular issue and more interested in how can we think better. You know? What is good thinking? And what can we do to be better thinkers. And that’s really remained the focus of my work since then. Anyway, at the time I had been an analyst and then I was a manager. And there was just a huge disagreement. We had a great group of analysts and they were led by a wonderful person, me! But we were so – and the question then was how soon will black majority rule come to South Africa? And how disatorous will it be because the whites – I hate using these words because thinking about people in terms of their skin color is the stupiddist thing imaginable.

[Applause]

But they used that words. Where was I? We were divided. Half the group thought that the whites would only give up, they can only be killed. There would be a blood you conflagration. And the other half, which didn’t agree, thought we were at some kind of magical tipping point and that black majority rule would come sooner rather than later.

So I spent a lot of time thinking about, you know, then and afterwards about what we could have done better, what were some of the mistakes that we had made. I’m going to go through those first. And then I’m going to hopefully, or I will, give you some ideas for doing it better and hopefully they will resonate with you all. We’ve been sort of – make them make sense in your world.

So the first thing, the next few slides are in the category of thinking errors. Right? And the first one is – We tend to make our decisions based on the information that is readily available, which reminds me the old story about the policeman who finds a person completely inebriated on his hands and knees under a street light. And the policeman says what are you doing? And he says I’m looking for my car keys. And the policeman says is this where you lost them? And the drunk says no, but this is the only place I can see. That’s the streetlight assumption. We’re constantly making assumptions that the information that we get accurately reflects reality, when in fact we need to think much harder about whether the information that we’re receiving does accurately reflect reality because usually it doesn’t. Usually the information has a lot of bias. In the CIA’s case, our biases were things like how the Reagan administration wanted to look at the world and the kinds of questions we asked our sources.

For example, during the Saddam Hussein WMD experience of recent memory, nobody asked Saddam whether he had Weapons of Mass Destruction.

Trends. This is just, this is really so sad because we all treat trends as if they’re about the future. And trends of course are never about the future. Trends are always about the past.

And so trends are gate points from the past. It could have been one minute ago, but they’re still the past. And it’s always a mistake. And your financial planner advises you of this but you ignore him or her. It’s always a mistake to think that trends can be project into the future. This is actually a trend of the Great Depression that started in 1929. The first big dip is the stock market crash of 1929, and there is a recovery. People are beginning to think the worst is over when in fact the stock market simply continues to decline until I think this chart ends in the 1930s. But of course war is always good for an economy. It brought life back to the American economy.

So important. And yet it’s so seductive for us to think about trends.

Chance. So I started to think about chance. Chance is almost a mystical thing to me. I was reading an analyst paper. And in the paper at some point she writes X had a chance. And I was thinking what is she trying to say? And I realized when I read that, that nothing happens with a chance. When we say happens by chance, what we’re really describing is an event whose causality we do not yet understand. This is critical. Because when you’re looking at a lot of information and something happens and you go “Well that was a just a fluke,” you’re actually making a bad decision at that point. Because what you need to do is look at this thing that happened by chance and spend a little time thinking about whether or not you can – there’s something about this causality chain. Because if you do begin to understand why the flukish thing happened, then you’re really getting some much more information knowledge. So the bottom line for me, nothing happens by chance.

I was challenged on this once. It was a very good conversation. And basically it has to do with the phenomenon of randomness, which when you look at it from a perspective, seems to look like chance. I can go further into this.

Exponential causality. This is the best illustration I could find of this exponential causality. I think most of us are familiar with the fact that we’re all really bad with exponential numbers. This is what makes us all kind of crappy at statistics. Right? This will happen if we just do this kind of linear projection, right? But I think there’s another phenomenon that is not well discussed, which I call exponential causality. And in this grand taxonomy of rap names how each name moves to another name. When one happens, it doesn’t have one effect forward. It often has a multiplicity of effects, which can actually go back and affect other things in past history, if you think about it.

So exponential causality, looking at an event and think about what are the multiplicity of consequences this event could have is a very important way to think better.

And when we don’t do it, it’s a very classic way of not thinking well. And then the final thinking mistake that I talked about, that I think about it, is worst‑case scenarios. I happen to love this. I hope to die chases the red ball. Who has seen it before? It’s a worst‑case scenario. Right? This was part of some art installation maybe in Ohio. I also like thinking about if you look at a car that pulls up at an intersection and has to yield to the red ball.

[Laughter]

So here is the discussion. We’re going to put this red ball in a public space. Someone might have said oh, how sturdy is the red ball? Can it stop rolling? And maybe say well that’s a worst‑case scenario. And then what we tend to do when we hear the phrase worst‑case scenario is we tend to assume that it also means “Unlikely.” We tend to equate worst‑case scenario with unlikely. We conflate worst‑case scenario with a statement of probability, when hugely important to remember, especially when you’re working with national security, that the degree of risk or harm associated with an event and its probability are independent variables.

War with North Korea is a worst‑case scenario.

No solutions, only tradeoffs. I don’t agree with a lot of what he’s written, but I think this is a very insightful statement. And certainly my career in government led me to agree with this. This is one of the reasons why, for example, when I left my government career I decided one of my conclusions was that decision making is overrated. Right? Because we make a decision to reach a solution, which falls apart a few weeks later. So if there are really few solutions, and most of the time are making tradeoffs between different things, then one of the things that happens that we don’t take into consideration as much as we should is that when we’re doing a tradeoff our value systems really come into play.

So I’m going to do this tradeoff because I don’t care so much about the people in the suburbs. Or I’m going to do this tradeoff because I think the future of the economy is in services, not in manufacturing. Right?

So you think about the fact that solutions are rare, tradeoffs are common. And to decide what you’re going to trade off, you’re really bringing your value system into play. That’s why clear thinking and mapping out a problem is very important.

So now I’m going to share what I learned as techniques for better thinking. Are we okay? Are you with me?

Audience:

Yes.

Carmen Medina:

So the first step is develop an – landscape. Now in 2002, I was the chief of the strategic assessments group. So this was this group that was supposed to go way out to the future and think about big problems. So they thought about things like the future of warfare. This is by the way the analytic landscape that created Future of Warfare. And they thought about globalization. 2002. And I became the chief of this group. And I said so how do you know the full range of issues that you should be thinking about in terms of the future of warfare? How do you know that? And they said, well what did they say? What do you think they said? How do you know, how do you determine the taxonomy of issues that you should be thinking about in terms of the future of warfare?

So I created an assignment for all the teams. The summer of 2002 and said I within the you each to create an analytic landscape of your domain. And I have two rules. Three rules. You all have to work independently from each other. You all have to engage with outsiders. And you all have to provide me a graphical presentation, not just words, which was a big deal for the CIA.

So this was one of my favorites. What they did is they created, they interviewed a lot of experts, and had them rate all sorts of different types of conflicts. And they createed a topography. Like mountain ranges. And one of those peaks in the back I’m sure was like Conflict with North Korea. So this is an example of an analytic landscape.

Now how could you do a good analytic landscape? What are some things you can do? Be engaged. That’s a good step. But there are some other ideas. It would be a good thing, for example, to prompt them with things that they’re not thinking about. When we think about an issue, we tend to just think, you know, we just talk about what’s in our head. So for example, ask your team for the weekend to go out and bring back to the office on Monday anything that they read or saw a video that made them think about the issue. And if you’re really smart, you say “You can do the New York Times, You can do the People Magazine, you can do Snapshot” in other words have assignments. And have everybody come together and share all of these things and as they’re shared, develop a landscape of these ideas. So that’s a way to inject different thinking. So that you create an analytic landscape that is not just a projection of what will you already think. Because that’s the real flaw in creating it.

A second thing that I advise in terms of better thinking is to articulate your thinking strategy. Now who has seen this before?

Okay, again, just a couple of people. This has been out for 20 years. I didn’t invent this. It was created by a guy named Snowden, no relation. And for me it’s a great first step in my thinking strategy. The way it works is think about the design you’re making and the problem you’re trying to solve and the very first thing you do concurrent with making the landscape of it is to think about what kind of problem is it? Is it simple, complex, creative, or chaotic? Simple, it goes clockwise from the bottom right. Simple is a problem where cause and effect is very clear to me. So perhaps fixing a car can be called simple. Although maybe I’m being unfair to mechanics.

Complicated is very cause and effect is clear after a lot of study. So it’s multiple causes and effects and there are feedback loops involved. So that’s complicated. That’s actually the problem space where expertise is most useful.

You could say that if you have a simple problem a checklist will take care of it. You don’t need expertise. But if you have a complicated situation that you’re dealing with, you need a lot of expertise.

Complex is a situation where it’s difficult, if not impossible, to understand the cause and effect relationships at the beginning. And you sort of only learn them through trial, error, and probing, kind of in hindsight. A complex situation.

Clearly the American elections of 2016 were complex and we did not realize that. Right? Interestingly enough, complex situations are situations where relying too much on expertise can be very dangerous. Because the expert will of course try to reduce the problem into the box that he or she knows. And a definition in a complex situation exceeds the parameters of present‑day expertise. In chaotic, if you’re trying to figure out where that is, that’s where none of you want to be, in a chaotic situation. And there’s oodles of information on this on the internet. Many people have done riffs on it and it’s connected.

But this just happens to be the first step of my thinking strategy. So when I look at a thing, a problem, that’s the first thing I try to think about. And then that determines everything else I do.

Know your thinking style. I know it’s pathetic that I’m using these GIFs.

[Sneezing]

Bless you. But every presentation is better. If I had more time, I would take you through a thinking style inventory that I would like. But I will say this. Some of us are concrete thinkers. We’ve been talking a lot about engineers. They tend to be concrete thinkers.

Some of us are more interested in abstract ideas. That’s me.

Some of us like to think in very orderly ways.

Others are much more interested in serendipitous. This is different from creativity. You can be creative in any of those thinking styles. But it’s what appeals to you and how do you process information? How do you learn? And I’m a random, extra random thinker. So very free associating. So I need to partner with a concrete sequential thinker. Right? I also tend to be an optimist! I’m a Winnie and I need an Eeore as my thinking partner. I heard people over the break talk about whether or not they should work together. Over time I think the Winnie the Poohs and Eores need to work together. And you broaden the landscape that you’re thinking about. And you can’t be unbiased but you will reduce the bias in how you look at the problem.

So think together. I love this. People talk about collaboration. And in my experience, what we call collaboration in government, and I also by the way worked where I learned much of what I accused the CIA of is really just symptoms of large organizations, which is rampant in the Western world, if you didn’t know.

But much of what we call collaboration is deconfliction. You have your plan and it’s almost ready for prototype or pilot and then you bring in these other people who are supposed to have a chomp on it. Wrong! That’s not collaboration.

So as hard as it is to do, collaboration has to be in the thinking process has to start as early as possible. So respect your intuition.

So what is intuition, right? I’ve been thinking about what is intuition. And I think intuition is when your mind tells you something without articulating it in words. So when you think, it’s very hard to separate our language capacity from our thinking capacity. So we tend, because we’re such verbal creatures, and so there’s always a dialogue going on. For unhealthy people, there’s too many dialogues going on. So we tend to equate that dialogue in our head with thinking. But your brain is thinking even when you’re not using words. And intuition is when your brain is presenting you with an idea that you have not yet articulated.

And finally, you need to respect, and you guys know this because you come from a design background. You need to respect the importance of emotion and how people react to things. Who is this activist by the way? I am so interested in this generational thing. It’s Betty Davis. And she’s coming out of her not very tiny house. And the importance of emotions in our design. And the reason why I mentioned this is when people talk about a thinking process, too often they don’t include thinking about emotions. And emotions clearly has to be one of the most important things that you consider as you think about a situation.

So hopefully I’m leaving enough time for questions. I love this GIF.

[Laughter]

Even though it doesn’t really apply to anything I’m talking about.

[Laughter]

I love to use it. And I know it’s kind of pathetic that someone like me is using GIFs, but I’m not using emojis, so it’s all good.

How many of you are managers? How many of you oversee teams of people? About half the room. Maybe even more. So as a manager, we want to all provide for interventions with our teams to be like that small vacuum cleaner. And we would like our teams to be like that dog where they’re truly ecstatic if not orgasmic about our management style. We would like that to be the case.

I talk about a whole nother topic, and how to lead in a way that invites your colleagues to share what you believe in.

And I thought I would end with a couple of slides about that. These are busy and hard to read.

The first one is what do rebels want from their bosses? And you could say what do employees want from their bosses? And if you look at these, these are really geared about how bosses can deal with their teams so that they truly indicate to their teams that they are open to different points of view.

So again, I’ll put the slides up. And you’ll be able to see them there.

And then the second one, which is even bussier. I like to call this so they’re destroying the conventions of what good bosses do. So you’ve heard the phrase, perhaps you’ve even used it yourself “I have an open door policy.” Right? I hate that phrase. Right? So when you tell an employee you have an open door policy, who are you putting the onus on? Them! And then where is the conversation going to occur?

So my bottom line is if you have to say you have an open door policy, you don’t. If you actually have to say those words, then everything else that you’re doing, all your other actions seem to kind of contradict the idea that you welcome employees’ opinions. There’s a great phrase attributed to St. Francis of Assisi. Evangelize and when possible use words.

Another stupid problem is don’t bring me a problem unless you have a solution. What are you doing there? You’re making it about an individual solution. Not a team. The person who sees the problem may not be the best person to come up with a solution. It’s kind of ridiculous.

I think I left about eight minutes for questions. So that’s my Twitter handle. You can reach me at [email protected]. And I joined Twitter in 2008, which of course is against CIA policy.

Any questions?

[Applause]

Audience:

Where’s the thing? I want to throw it.

Carmen, do you want to take questions? Who has a question for Carmen?

Carmen Medina:

Yes.

Audience:

After that accident in 2016, I’m still nervous. I threw something that was heavier than I should have. And somebody came to all of our events that year…

[Laughter]

Just a small abrasion.

Audience:

So my question Carmen is can you suggest techniques that you might have used with your own teams to help them become better thinkers?

Carmen Medina:

Actually help them become better thinkers. Well, the first thing I did, which comes as no surprise, I tried very hard not to be a micromanager. In fact, I’ll pull back. I think the only way you can try very hard not to be a micromanager is to almost advocate your management responsibilities. I have a whole problem with leadership by the way. But I resisted giving what would be normal advice to a person about how to think. I resisted telling people how to think.

At the time, the South Africans were in Namibia. I was beginning to see signs that the South Africans were about to pull out. But I resisted telling the analyst Karen that. I kept waiting. She said is it okay for us to suggest that South Africans might leave? I think people think better if they think it’s their responsibility to think.

Another technique that I wish to do, I’m a big fan of texture and crunchiness.

I had these cards. Happiness, North Korea, trade, anything I could think about. And I liked to make people draw three random cards and then tell them to suggest to me, come up with something that would affect the issue that they’re working on that’s inspired by those three random cards. So my favorite example is someone drew God. No, someone drew religion, unmanned vehicles, and China. Those were the three cards they drew. And they came up with in the future, in the near future China will create a satellite that will process all the world’s knowledge and it will be so impressive that a religious cult will follow them. And I went “I can see that happening.”

[Laughter]

But without those inputs. The key I think is to get people out of what’s in their head. And you can create these cards at home. You can just like do a search and create cards for every technology and all the cities in the world and think about love, sex, fashion, all the things that affect us.

I’ll stop there. There’s one way in the back and right in the front. All the way in the back.

Audience:

[Away from Microphone]

Carmen Medina:

That’s a good question. I didn’t say rely on your intuition. I said respect your intuition. And then openness to other people’s ideas. I think it was Scott who said in his presentation that one of the reasons we’re not creating enough is because people censor themselves and don’t say their ideas. Right? They don’t say what’s in their head. So I think people, they need to have a process. One way you could do this is have a process before the start of the meeting, before you get into the agenda is have everybody go around and say what’s an your mind. What intuition do you have about this issue? What’s on my mind? And you need to model the behavior by saying something crazy yourself. And perhaps having someone to come up with the stupiddist idea they can. And you need to not only respect your own intuition, but you need to make it clear to people that you want to hear what their intuitions are, as well.

As far as I’m concerned, if you want creativity and good thinking.

Audience:

I have a very similar question. About these biases that we all have. [Away from Microphone]

Carmen Medina:

I think leadership has to be speaking, speaking as a position of a leader, the less you think of yourself as a leader, the better. And if you, you know, there are some questions that you can ask your team members. Any comments. You speak for 90% of the time. And then there is an indication that the meeting is over. Better questions to ask. What did I get wrong? What am I missing? How would you do it differently? Those are, you know, we can think of others.

Questions to ask that directly convey to the people that you’re working with that your ideas are not primary, and you really want to hear what the other person has to say.

With that, it’s time to eat. Thank you very much for your attention.

[Applause]

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