Leading in Information

Chip Cutter and Jennifer Maloney writing in The Wall Street Journal (subscription required):

The new coronavirus’s spread in America has prompted corporations to close offices, factories and stores, sending tens of millions of people home, where a swath of the workforce—from customer-service representatives to chief executive officers—have had to figure out new ways to work.

The result is perhaps the most radical and swift change in U.S. business in living memory. That’s posing a monumental management challenge of leading employees—those lucky enough to have kept their jobs—to sustain operations from home while also keeping them calm and safe.

The article goes on to profile CEOs of companies of diverse sizes, and the challenges they and their employees are facing as their workforces move to work remotely. These challenges include the loss of camaraderie, feelings of insecurity, managing young children while trying to work, the loss of structured daily routines, and more.

Instilling a sense of direction and purpose is hard enough in normal times when regular communication channels are intact. But leading during difficult times, when conditions are changing fast, and normal channels break down, can be extraordinarily difficult.

Thinking about the issue of leading remotely, I’ve been reflecting on this tweet, which highlights New York Governor Andrew Cuomo’s communication style during the current crisis:

This list strikes me as an excellent communications guideline for leaders. But not all digital channels will lend themselves equally well for each attribute. For example, I’d expect authenticity, tone, and empathy to work best over synchronous video calls, where people can hear and see each other. Conversely, asynchronous channels lend themselves to frequent, clear communications.

The times call for leaders with excellent communication skills, but also who can adapt those skills to this new world in which we all interact over digital channels all the time. We can learn communication skills, but adaptability is a harder attribute to learn. I expect people to give each other the benefit of the doubt in the early days of the crisis. We’re all trying to cope with the changes, and will be more patient with each other’s clumsiness. But as time passes, we’ll expect leaders to get their stuff together. The sooner, the better.

With Business Turned Upside Down, CEOs Face Monumental Leadership Challenge

The Kranz Dictum

On the afternoon of January 27, 1967, the crew of Apollo 1 — astronauts Virgil “Gus” Grissom, Ed White, and Roger Chaffee — were killed in a horrific accident. The men were sitting inside the sealed command module of their spaceship during a launch simulation when a fire broke out. Fed by the pure oxygen environment inside the cabin, the conflagration spread quickly. The astronauts didn’t have a chance.

The Monday morning after the accident, NASA Flight Director Gene Kranz — the person responsible for coordinating Flight Control during a mission — addressed his team. This is what he told them:

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How Designers Can Help Bust Silos

When I talk with folks in large organizations, I often hear a familiar lament: “We’re very siloed here.” By this, they mean the organization is divided into​ groups that don’t play well with others. Each group functions like an isolated “silo” that acts independently from the rest. They each have their own internal goals, incentives, processes, etc. which make it difficult for them to collaborate.

Siloing impedes the organization’s ability to respond effectively (and in a timely manner) to changing contextual conditions. Because it involves organizational cultures and incentives, it can be a tough challenge to overcome. People in silos have an especially hard time seeing things from others’ perspectives — especially their colleagues.

A big part of the problem is that people in these situations​ tend to communicate in abstract terms. Often they’re unaware of using language that reinforces the distinctions between them. With our emphasis on making things tangible, designers can help them bust through these barriers.

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Designing the Right Things

At a high level, design teams in organizations face two challenges: Doing things right and doing the right things.

“Doing things right” is about efficiency: making the best use of time and resources. When seeking efficiency, leaders ask questions about their team’s production function:

  • Do we have the right roles?
  • Are relationships between roles organized optimally?
  • Do we have the right people in those roles?
  • Do we have enough people in the team? Do we have more people than we need?
  • How do we recruit the right people into our team?
  • How do we nurture leaders?
  • What tools, systems, and processes can help us do our jobs better?
  • What mental models can help us do our jobs better?
  • Is our team culture conducive to producing good work?

For the most part, leaders trying to answer these questions have peers in the organization they can partner with: HR, IT, and operations. As design matures within organizations, there’s also more professionalization of the discipline without; this manifests in the growing interest in design operations and the documentation and sharing of best practices.

In other words, when looking to do things right, today’s design leaders have several starting points. But what about doing the right thing?

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JFK’s Apollo Vision Statement

Complex projects require coordinating and aligning the efforts of many people in different roles and groups. The job is possible only if everyone is clear on what they’re striving towards, and are compelled to do so. This calls for leaders to clearly articulate the project’s vision.

The importance of having a clear, compelling vision is one of the great lessons of the Apollo moon program. U.S. President John F. Kennedy laid out the vision in a speech delivered to Congress in 1961. This speech was meant to convince lawmakers of the worth of investing in space exploration. Essentially, the President was asking his stakeholders — Congress, and more broadly, the people of the U.S. who they represent — for funding for the project. This is something anyone working in a leadership position can relate to.

President Kennedy’s presentation is a model of how to clearly articulate and sell a vision, so it’s worth studying its highlights. The speech starts by framing the space program in the broader geopolitical context of the Cold War. The Soviet Union had by this point made several impressive technological advances, including launching Sputnik (the first artificial satellite) and sending the first man into space. U.S. efforts were seen as lagging behind the Soviets’, so the President started his remarks with the following statement:

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Twitter as a Public Square

Managing an information environment like Twitter must be very difficult. The people who run the system have great control — and responsibility — over what the place allows and encourages. In a conversation platform (which is what Twitter is at its core), the primary question is: How do you allow for freedom of expression while also steering people away from harmful speech? This isn’t an easy question to answer. What is “harmful”? For whom? How and where does the environment intervene?

Episode 148 of Sam Harris’s Making Sense podcast features a conversation with Jack Dorsey, Twitter’s CEO, that addresses some of these questions head-on. I was very impressed by how much thought Mr. Dorsey has given to these issues. It’s clear that he understands the systemic nature of the challenge, and the need for systemic responses. He expressed Twitter’s approach with a medical analogy:

Your body has an indicator of health, which is your temperature. And your temperature indicates whether your system more or less is in balance; if it’s above 90.6 then something is wrong… As we develop solutions, we can see what effect they have on it.

So we’ve been thinking about this problem in terms of what we’re calling “conversational health.” And we’re at the phase right now where we’re trying to figure out the right indicators of conversational health. And we have four placeholders:

1. Shared attention: What percentage of the conversation is attentive to the same thing, versus disparate.
2. Shared reality: This is not determining what facts are facts, but what percentage of the conversation are sharing the same facts.
3. Receptivity: Where we measure toxicity and people’s desire to walk away from something .
4. Variety of perspective.

What we want to do is get readings on all of these things, and understand that we’re not going to optimize for one. We want to try to keep everything in balance.

I’d expect the idea to be to incentivize “healthy” conversations over “unhealthy” ones. This would be implemented in the design of the environment itself, rather than at the policy level:

Ultimately our success in solving these problems is not going to be a policy success. We’re not going to solve our issues by changing our policy. We’re going to solve our issues by looking at the product itself, and the incentives that the product ensures. And looking at our role not necessarily as a publisher, as a post of content, but how we’re recommending things, where we’re amplifying, where we’re downranking content.

Twitter has a great responsibility to get this right, because in some ways the system is becoming key public infrastructure. As Mr. Dorsey acknowledged,

Ultimately, I don’t think we can be this neutral, passive platform anymore because of the threats of violence, because of doxxing, because of troll armies intending to silence someone, especially more marginalized members of society. We have to take on an approach of impartiality. Meaning that we need very crisp and clear rules, we need case studies and case law for how we take action on those rules, and any evolutions of that we’re transparent and upfront about. We’re not in a great state right now, but that is our focus. I do believe that a lot of people come to Twitter with the expectation of a public square. And freedom of expression is certainly one of those expectations. But what we’re seeing is people weaponize that to shut others’ right to that down. And that is what we’re trying to protect, ultimately.

As a Twitter user, I was pleased to see the depth of the thinking and care that is going into these issues. I learned a lot from this podcast about the reasons for some of Twitter’s controversial design decisions. (E.g. I now know why Twitter doesn’t have an “edit” button.)

Unfortunately, the conversation didn’t address the elephant in the room: Twitter’s business model. Ultimately, Twitter makes money by showing ads to its users. A good public square shouldn’t attempt to sway our opinions; it should provide the venue for us to form them through engagement with others. How might “conversational health” might be used as a means for persuasion?

Making Sense Podcast #148 – Jack Dorsey

What is a Healthy Society?

What is a healthy society? I was recently asked this question in an interview; I’m unsatisfied with the answer I gave, and the question has stuck with me. Here’s another try.

By society I mean the system created by the agreements we abide by when we decide to live in community; particular ways of being and organizing our activities that inform our behaviors as they affect other people. These agreements may be explicit or implicit. A trivial example: different societies manifest different attitudes towards how people wait to be served; a society with strict attitudes will frown upon the practice of cutting in line, whereas a more permissive society won’t. People’s shared attitude towards waiting is part of their social compact; they agree on what is acceptable behavior and how they will enforce it. Societies have many such agreements; they define a sort of operating system for community.

What about healthy? My starting point is Bucky Fuller’s aspiration to make the world work for 100% of humanity. It’s an acknowledgment that current ways of organizing our activities are not working equally well for everybody. Although we’ve made much progress, there’s still much injustice and unnecessary suffering. (Suffering is inevitable, but we should strive to reduce it as much as possible.) In short, we can and must do better. Now, making the world work for 100% of humanity doesn’t mean trying to make everybody the same; that’s impossible and undesirable. Instead, it means ensuring everyone has the same opportunities to live a full, rich life.

But that’s not all there’s to it. Health implies longevity. (A healthy body is one that can last a long time; it’s the opposite of a sick, dying body.) We want societies that can maintain desirable conditions in the long term; for generations, with no end in sight. In other words, we want societies that are sustainable. A society that achieves equitable conditions on one or more levels but then destroys itself is (by definition) not healthy. (See tragedy of the commons.) Working towards sustainability calls for systemic thinking.

When contemplating the idea of a healthy society, I often think of James Carse’s book Finite and Infinite Games, which opens with this duality:

There are at least two kinds of games. One could be called finite, the other infinite.

A finite game is played for the purpose of winning, an infinite game for the purpose of continuing the play.

The members of a healthy society understand they’re engaged in an infinite game with each other, with people from other societies, and the environments that host them. Having evolved beyond zero-sum approaches, they strive to continue the play ad infinitum.


“If you weren’t an optimist, it would be impossible to be an architect.”
― Norman Foster

Designing an environment is an act of optimism. Why go through the trouble and expense of changing things if you have no confidence in the future? Conversely, you can’t do a good job at it if you lack the conviction that things will get better. (Ideally, your intervention will help.)

Being optimistic doesn’t mean being naive. Things are hard. There are injustices in the world. There are confusions and obfuscations. Evil and stupidity can (and sometimes do) win the day.

Being optimistic doesn’t mean believing positive thinking is all you need in the face of hardships. That’s not optimism; it’s delusion. Instead, you must cultivate clear seeing and thinking, and be prepared to work. (One of the things you must work at is maintaining clarity of vision and understanding when stupidity and evil are on the rise and actively working against it.)

You have a choice on how to interpret what you perceive around you. Silver linings abound if you know where to look. The pain in your side could be a passing thing or a sign of a serious disease. If it’s the latter, wouldn’t you rather know sooner rather than later so you can do something about it? The pain can be your friend; it can be the first step towards healing.

Consider the Avocado

Information architects establish distinctions that make things easier to find and understand. We set things apart into groups that make sense to people. By definition, things in one group are different from things in another group — if for no other reason, by the fact that they are in different groups. When done well, the groupings are obvious; recognizable yet distinct. In many cases, groupings are not obvious. Arriving at the right grouping is often anything but.

Consider the avocado. Botanically, it’s a berry. Most folks probably don’t think of avocados as berries, which they associate with sweet dishes. People usually consume avocado with savory dishes: salads, guacamole, etc. If you were asked to group avocados with other items, where would you place them? It depends on many factors. Who is the audience for the grouping? What is the purpose of the grouping? What other items are being grouped?

Arriving at the right grouping requires understanding what avocados mean in a particular context to particular people. Avocados will be grouped differently in a grocery store than in a botanical lab. Grocery shoppers may think of avocados as vegetables, regardless of what botanists think. Botanists may think of avocados as berries, regardless of what grocery shoppers think.

One of the challenges of establishing effective information architectures is that we’re often tasked by botanists to establish groupings meant for grocery shoppers. While the botanists may understand that a different grouping is required for a different audience, the novel grouping may feel wrong to them. In their world, avocados will always be berries.

Existing incentive structures may make it difficult for the botanists to imagine alternative groupings. Remember, we’re talking about meaning. For these folks, having avocados show up in a group under anything other than the “berry” group can be interpreted as an existential threat, especially if these groupings are exposed to people outside the organization — and doubly so if revenues are being measured against the groupings. (“My team is responsible for berries. We ‘own’ avocados.”) As a result, information architects must often work within political environments that nudge towards particular groupings for reasons other than making things more findable and understandable.

This is challenging, but it can get even trickier: sometimes you want avocados to be found while also changing people’s perception of what avocados are. (Maybe the organization is trying to re-position them in the market.) These cases require walking a fine line. On the one hand, you want grocery shoppers to be able to find the avocados in the groups they expect them to be in. On the other, you also want these people to start thinking of the avocados as being part of a different group. On the other hand (yes — this is complex enough that it requires three hands) you have the botanists wanting to drive their preferred view of things.

How do you do it? There are various things you can try. For example, you can use one grouping for the mechanisms that allow people to find their way to the avocados and another for the context where the avocados sit in. You can also try to re-frame the avocado by establishing a marketing campaign. (“Avocados: The new miracle smoothie ingredient!“) You can establish thesauruses that map one term (“avocado”) to another (“berries”). In any case, you should carefully test the new organization scheme. When grouping things in novel ways, data is your friend.

IA work boils down to grouping things in ways that come across as “obvious,” even if they’re new. Where you place the avocado will depend on how people understand it to begin with; what it means to them. But where the avocado shows up will also affect how people understand it and what it means to them. Of course, what’s obvious to one set of people will be anything but to another set.

Ultimately, information architecture aims to change behavior through distinctions. IA has the power to do this. But grouping and labeling things to change behavior also entails great responsibility. The distinctions we layer on the world change how we understand it, the things in it, and ourselves. We must vie to establish distinctions that help nudge things towards positive outcomes at various levels. Yes, we’re helping sell more avocados, but we also want to know this will be good for those of us who eat them and for the societies who produce and consume them.