Leadership in Complexity – Conversation, Values, Democracy, Slippery Slopes, and Genuine Evil


I posted something in an Air Force Facebook group the other day that went something like this: 

I think more of our mid-tier leaders — officers and NCOs — need to be enabled, educated, and empowered to engage in the difficult task of rooting out, tamping down, and expelling extremist, sectarian ideologies among our troops, which include the hateful ideologies that gave rise to the insurrectionist actions we saw yesterday in the US Capitol. We need to be capable of differentiating these divisive strains of hate from mere politics, which they will continue to masquerade as, just as we need to absolutely reject the idea that inclusion, diversity, and equity are inherently political, which they are not.

Lead from a place of values, with empathy, vulnerability, and courage.

I then linked to an article about an Air Force senior leader – Lt Gen Hinote – who had spoken out publicly about the threat that extremist ideologies pose to our republic, as demonstrated by recent events. 

So I’m a mid-level leader myself, as a Technical Sergeant in the Air Force, and I felt it was important to talk about this issue. I wanted to highlight how senior leaders set the standard for how we talk about these kinds of things- because I think that’s one of the most important things for leaders to do in the complexity and scale of an organization like the Air Force- they provide clarity about our shared values and what words and behaviors constitute upholding or violating those values.  

I have been very interested in how values hold an important systemic function in the complexity of an organization, because our systems of simple rules and policies will always encounter situations in which they did not perfectly predict future contexts. That’s how complexity works. You can’t actually anticipate everything about the future. This is why autonomy is such an important element in handling complexity. There is no rigid system of rules and policies that won’t fail catastrophically at some point if you don’t enable values-based autonomy and empower the system to learn with changing information.

This is largely what my talk at TEDx Hickam was about, and the story I tell there- in which the rigid policies of the Exceptional Family Member Program actually harmed my family for several years instead of helping us – the solution to that problem was values-based leadership. Our Wing Commander at the time – now General Martemucci – liked to repeat this phrase to unit commanders: “Stop doing stupid stuff to Airmen”. My unit commander at the time once said to me directly that that phrase was instrumental in giving him license to escalate and intervene on behalf of my family, even though separating my family while my daughter was dying was well in line with Air Force policy. Policy is not the baseline. It’s a system intended to uphold, support, and deliver our values… and values enable leaders to uphold, exempt, or change policy in the face of new information.

So I appreciated seeing General Hinote model how we speak about our values in the face of the political and societal unrest we’re seeing.

Particularly with this difficult of an issue, one that gets highly politicized, we need leaders to set the tone, to reinforce and demonstrate what talking about our values looks like. I’ll point to how the Chief of Staff and CMSAF General Goldfein and Chief Wright, and now General Brown and Chief Bass… in the wake of the unrest and outrage we saw after the death of George Floyd at the hands of law enforcement, unrest over long-standing issues with race and police brutality in America… those Air Force leaders set the standard for how we discuss race and racial issues as leaders and members of the Air Force. One impressive thing that Chief Wright and General Goldfein did was to actually have a public and visible conversation. They literally modeled the behavior for leaders below them – a white man talking to a black man about the experience of racism in the Air Force and American society and how leaders can rise to the challenge of having that conversation. This is important because it gives others permission and conveys to them just how to go about stepping into the discomfort of that experience- how to engage in empathetic and active listening. It gave lower-tier leaders license to do so. Values are critical, but values alone aren’t enough. How values translate to actions has to be modeled, especially in the face of particularly difficult challenges.

Conversation plays an interesting and critical role in the healthy learning and iteration of a human system in complexity. As I mentioned in the previous video on Tribes, Institutions, Markets, and Networks… conversation is a tribe-level communication method. Conversation is how we achieve coherence and alignment internally on an individual and small-group level. This is another area where leadership overlaps with the fields of design and entrepreneurship, as Steve Blank likes to tell people, you have to get out of the building if you want your startup to succeed, and talk to actual customers. 

So I’ve seen a lot of senior leaders do this thing where they drop in and make an appearance at the tactical level… they sprint through usually with a massive entourage of people, shake hands and take pictures… once we had the Chairman of the Joint Chiefs of Staff, Admiral Michael Mullen, swing through to hand out coins like he was Santa Clause,

And I want to point out that that’s not the same thing. You need conversation, to engage in actual discovery. I learned as a junior enlisted disgruntled type that that was my chance to bring ideas up to people who might not have had a chance to hear them, because they were being protected from tactical-level information…

So a lot of people responded to my initial post about how we need to uproot and expel extreme sectarian ideologies with the idea that I was calling for the “thought police” and a number of people used the phrase “Slippery Slope”. Some people were concerned with the vagueness of my terms, so assumed I was referring to some kind of system in which we decided what opinions everybody needs to have and then if they showed any sign of deviating from that we hunted them down and ruined their livelihood. People pictured this apocalyptic future in which some far-left-leaning MSgt could just kick people out for not being politically correct enough. 

I anticipated this kind of reaction, because I think it’s the type of logic that people have been trained to employ by political tribes that are first and foremost interested in strategic posturing, dunking on social media, and not losing arguments rather than a holistic view of a system that functions for all. So I wanted to share a couple of things that I think help put my ideas in context. 


First, I think people should understand why the ‘slippery slope’ argument is a fallacy and not a useful or effective way to parse the logic of an idea. Slippery slope is a broad appeal to imagining unlikely outcomes (though they might feel likely) as a means to inhibit action, regardless of whether those actions have merit. Saying ‘slippery slope’ is saying that there is a directionally-specific gravity to certain kinds of actions that will inevitably result in a chain reaction of subsequent consequences that can be anticipated in advance. I really wish this was the case, because it would make the whole world a whole lot simpler than it actually is. Second and third-order effects should be considered and mitigated if possible, but saying that expelling extremists from our ranks would inevitably lead to having thought police is a little bit like saying gift-giving will inevitably lead to the collapse of capitalism. Some values-based restriction does not inevitably lead to value-violating restriction and to say so is fallacious. 

Slippery slope is only not a fallacy when you’re dealing with one-to-one cause and effect systems- that is to say ordered systems in which you actually can predict outputs from inputs- when the following criteria are met: The system is closed, you can account for all relevant factors, and the relevance of factors never changes.. An easy rule of thumb – would intelligent people or experts disagree on whether an outcome will occur? If they would, you’re probably dealing with complexity, and slippery slope is a fallacy. If they wouldn’t disagree… such as when predicting the direction a ball will roll on a literal slippery slope… then have at it. Call that slippery slope what it is, and I’m sure nobody will have a problem with that. 

The degree of complexity is actually extremely relevant to the idea of setting hard limits on behavior and speech. A system needs to be bounded, for example the medical profession bounds it’s role in society with values like “first do no harm”. A system in complexity has to exist on a foundation that informs whether the ordered systems we employ (like rules and policies) or actions we take are actually meeting the intent of our profession. In the book Team of Teams, General Stanley McChrystal describes transforming the Joint Special Operations Task Force from a rigid, micro-managed system to one in which values informed autonomy drove action at the tactical level. They moved from being primarily driven by top-down instruction to more heavily driven by values interpreted and implemented within tactical context. 

In the comments thread on my Facebook post I also encountered a number of people who seem to be under the impression that politics are values, or somehow are the only pure expressions of values. Here’s a framing that I find more useful and inclusive: 

Our politics are simply theories of governance, masked by strategic posturing, fueled by hyperbole. Existing as we do in complexity, as much as your favorite pundits might like to tell you, these theories are not foregone conclusions. Lots of experts disagree on theories of governance about the economy, social welfare, and basically everything else. Politics will continue to be even more difficult to parse and navigate as politicians continue to be disingenuous and intellectually dishonest in attempts to score points for their team. 

But our politics are supposed to exist on top of an underlying framework of democratic values. Democracy is founded on the idea that governance is best modulated by diversity of demographic, of thought, by inclusion and compromise. This is an operating system intended to navigate the complexity of human experience at scale, and it will never be perfect. There is this whole system in place intended to represent the people, prevent the tyranny of the masses and put checks on any office or branch that might be leaning too dangerously hard in a particular dogmatic direction. Monocultures are structurally weak. Inclusion and equity are an important part of the answer. 

So beyond our personal political affiliations, it makes sense, especially as members of the military, to be beholden to a higher set of values and be held to the standard of upholding those values. You can’t defend and undermine democracy at the same time. If your personal or political opinions pit you against the values that underlie democratic norms and institutions, you have a conflict of interest. I’m not talking about how democrats and republicans like to declare outrage at the latest political machinations, which have gone on for as long as our country has existed, although if machinations are severe enough they probably could result in a death-spiral as trust is lost, compromise becomes a thing of the past, and the only way to make progress becomes politically driven rather than values-driven. Democracy can fail for more than just one reason. But just from a 

I like to compare this to the issue of inclusion and diversity. If someone expresses views of white supremacy or belongs to a hate group, that should be automatic grounds for dismissal from the force, because you can’t lead troops if you think some are inherently superior, and you can’t defend democracy if you don’t believe in equal access. 

James Carse, in his book ‘finite and infinite games’ describes evil in this way: 

“Evil is never intended as evil. Indeed, the contradiction inherent in all evil is that it originates in the desire to eliminate evil. Evil arises in the honored belief that history can be tidied up, brought to a sensible conclusion. It is evil for a nation to believe it is the last, best hope on earth. It is evil to think history is to end with a return to Zion, or with a classless society, or with the Islamicization of all living infidels. Your history does not belong to me. We live with each other in a common history.” 

Carse describes evil as “when an infinite game is consumed entirely within a finite game”. 

He says evil is the “restriction of all play to one or another finite game”.

That is precisely what I see in allowing politics – mere theories of governance- finite games about winning this match or this round at all costs – to supersede what ought to be our more sacred and well-bounded values – democracy, inclusion, equity, and a genuine concern for the well-being of one-another. 

Stop trying to just win at all costs. The costs of winning might be more than you can 

Have more conversations. Let’s get on the same page about what values we need to share as an institution and as localized tribes that enable us to support and defend the constitution, our democracy, and to support one another as individuals, not allowing political affiliation to get in the way of that.

This has been a pretty long video, and I considered cutting out the whole bit about slippery slopes, but I realized it’s actually at the heart of my point here: 

When you allow political figures to convince you to see the world as a well lubricated mountain-range made up of nothing but slippery slopes, that is when you see history as the foregone conclusion of simple factors, you see the future as simple and predictable – the logical next step is to try and take away as much power as possible from those who might take your society in any direction that might place you on one of these slopes. 

We tell ourselves simple stories about the past, and it leads us to see the consequences of the present as simple, but they never are. 

But when you see history as complex – the outcome of various factors and too many to count, then the most important thing becomes defending and operating within a framework that is values driven – not belief driven. 

Carse describes belief as the point at which thought ceases. We believe a thing and that becomes a hard line beyond which we stop thinking critically. All new information is either ignored, refuted, or incorporated into the belief. 

Here’s how we don’t allow beliefs to consume our participation in more infinite games. Have conversations. Trust the experience that you are hearing from one another. Co-create solutions that are coherent with the experience of others, not only your own. 

And most importantly – figure out what values must be adhered to in order for this system to continue to function for everybody. And don’t be afraid to act in adherence to those values- expel those who violate them. Protect our democracy. Decry intolerance. Opt for inclusion and tolerance with the exception of tolerance that puts the inclusion of others at real risk. 

Thanks for your time. 

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