Chapter Seven

The North Star—Not the GPS

Everything you’re sure is right can be wrong in another place.

—Barbara Kingsolver, The Poisonwood Bible

In the late nineties, the U.S. Naval Academy did away with its coursework on celestial navigation and replaced it all with training based on GPS and satellite technology. In the wake of hacking threats, however, the academy has reversed this decision. In 2015, they announced that they would, once again, require officers in the navy to have a working knowledge of navigation by the stars. Frank Reed, an expert in celestial navigation, told WBUR’s Here & Now that a return to this older form of navigation was not about the romance of an ancient practice. “Every navigator,” he said, “should use all the available information.” In this way, navigation is less about blindly following the GPS or a satellite and much more about assembling an interpretation from all forms of data.

Celestial navigation provides an apt metaphor for leadership in today’s organizations and companies. Instead of simply reacting to one type of data, it is the role of the leader to make sense of all data: to interpret the facts available from multiple sources—technical and human—and to develop a strategy accordingly.

In this chapter, I want to introduce you to several sensemakers who have cultivated mastery in this interpretive art. The skills they possess could never be captured in any kind of quantitative evaluation. As a result, this kind of intelligence—extraordinary in its sensitivity, sophistication, and courage—often goes unheralded. And yet, if the hardest—and most lucrative—problems of the coming century are cultural, then these are the very skills we need to be celebrating. In the following four stories, we encounter expertise in social intuition, political innovation, active listening, cultural interpretation, analytical empathy, and artistic integrity. Here is sensemaking as it is practiced by everyday masters:

1. Sheila Heen: Becoming One with the Room

I am always assessing and responding to the core emotional interests in the room.

Sheila Heen is a master teacher in the negotiation and conflict resolution field. She and her colleagues have been team-teaching an advanced class called Difficult Conversations at Harvard Law School for twenty years now. Through her consulting firm, Triad Consulting, she and her partners also work with corporate clients and organizations to equip leaders to address the hornet’s nest of issues that come up around conflict, influence, and leadership in the workplace.

At a recent session with a Fortune 500 corporation, Heen stood in front of a room filled with people from different departments in the company. She was there to do a session on “feedback”: working with senior leaders to build their capacity to give and receive feedback in more productive ways. As they talked about the challenges and dilemmas feedback presents, one particularly outspoken executive raised his hand and offered, “I have problems with the way my wife gives me feedback.”

His colleagues chuckled.

“She won’t just tell me what she wants,” he told the room. “Her feedback is incredibly unclear.”

Heen’s job in moments like these—to help these leaders learn about themselves and about communication—is complicated. She knows that everyone in the room is a senior executive—she has the org chart that lays out the official roles and hierarchy of the leaders in the room. But more important than the job titles are the relationships in the room among the executives and how they perceive each other: Who is respected? Whose advice or insight carries weight? Who is seen as “difficult”? Who is trusted? Who is beloved?

Heen knew instantly that the man was well-liked. She could feel that from the mood in the room and the warmth of the laughter. But she could also see from the half smiles on people’s faces that the executive didn’t always have clarity on how others perceived him.

“So what do you say to her when that happens?” Heen asked in response. She could feel the curiosity in the room open up even more, as those assembled were interested in what they might learn if she pressed their colleague further.

And he was eager to share more. “I say, ‘I don’t understand what you want from me.’” He raised his palms in defiance, offering up a gesture of frustration to the room. “Come back to me when you know what you want me to do,” he concluded.

Heen didn’t miss a beat, “So you’re telling her that you only want feedback from her when it’s perfectly articulated.”

“Yes,” the executive said with satisfaction. “Exactly.”

At this point, the room shot up in temperature. Recognition swelled like a wave, moving from one participant to another, gathering force. An insight was breaking. Heen now had a decision of insurmountable complexity in front of her: how best to ride this wave of insight to maximize the learning while also managing the risks involved. The room was starting to understand the man’s blind spot about protecting himself from receiving feedback, although he himself did not. Should she expose him in front of the others, explicitly drawing out the insight and using it as a way to break open the workshop? Or should she end the conversation and hope that this executive and everyone else would reflect back on the moment and arrive at some kind of understanding later on? Exposing him would offer up a wealth of pedagogical riches, but what if it caused him shame or embarrassment? What if he became angry or sullen and this soured the open and trusting atmosphere of the workshop she had established?

Countless different data streams go into every single millisecond of Heen’s craft. Beyond the org chart she is always reading (and re-reading); there is the real-time social context of each and every executive she is addressing in the moment. But there is a second aspect to relationships that she is also always reading: the leaders’ relationship with themselves. Are they self-conscious? How much do they care about others’ opinions, or looking good to their peers? Do they want to be here? Are they cynical? If they have a sudden—and public—aha moment, will they find it exhilarating or humiliating? Most importantly, do they have a sense of humor about themselves?

Every single clue she extracts about an individual can dynamically change as the room shifts from mood to mood. One individual might be reticent at first but then become gregarious and fun-loving when the mood of the room shifts over to jovial and playful. Another individual might begin with a very impassive response and then grow more aggressive or more deferential depending on the feedback from her superiors or someone she respects nearby.

But all of that is just the beginning. Heen also has to know about the company culture as a whole. Do they perceive of themselves as competitive? Egalitarian? Creative? Hard-nosed? The underdogs? The alphas? The only ones who “get it” but are still treated as second-class citizens as a team or function? Once she has an understanding of the larger picture, Heen then needs to sense the chafing points within that culture. Where do the misunderstandings occur? How are aspects of the culture holding certain people and departments back? What can be said out loud and what remains unspoken? How much can Heen push any one individual in any given moment and how much can she push them as a group?

All of these considerations have not even touched upon her material. It is a given that Heen knows her content cold—just as the jazz musician shows up at the club with a technical expertise—but she has to use that content to tune in to the students. She has to reach outside herself to make something magic happen in the room.

As the room grew hushed, Heen knew just what to do. “It sounds like you only want perfectly delivered feedback,” she shot back at him with a playful smile.

The room tittered in growing anticipation.

“Well,” the executive considered this. “I guess that’s true…”

“But can feedback ever really be perfectly delivered?” She paused, gauging his facial expression as he followed her reasoning, then added, “It’s kind of a clever way to ensure she can never actually give you feedback, no?” she teased.

The man stood still, shocked, momentarily off balance. The room erupted in laughter and then he, too, smiled; his entire demeanor suddenly cracked open with a new understanding about himself and his relationships.

“Yeah,” he said, laughing at himself along with the room. “Yeah, I guess feedback can’t ever be perfect.

“I still make this mistake,” Heen confided to the room, deftly shifting the focus away from the man and back onto her teaching. “I feel really frustrated when people offer me unclear or unfair or poorly delivered feedback. But giving and receiving feedback is not about finding the perfect words, or even the right words. It’s really about having the right attitude. If we want to receive feedback well, we need to be curious about what someone is trying to tell us—even when they are doing a terrible job of telling us. We’re usually going to have to work to see what our givers are trying to say.”

In that moment, the tension broke. The room, as if a single entity, absorbed Heen’s insight. Teacher and students: everyone was “in it” together. Over lunch the executive approached Heen to thank her and tell her how “big” that learning was for him, both for his marriage, and also for his leadership.

“The research I present on how to deliver feedback and have difficult conversations melds with the way I interact with them as a teacher,” Heen told me later that day. “The teaching itself is a negotiation. You’re negotiating for engagement and credibility, a willingness to try new things and to own up to mistakes without getting defensive. I have to be using the skills I’m teaching in how I’m teaching them.”

Whether teaching or mediating complex conflicts, Heen described her overall experience with reading all of the complex human signals as “crossing over the river.”

“There are moments when my internal voice is preoccupied with the content—how to explain something more clearly or what to say next—but then, inevitably, I cross over the river and the material is at my fingertips. Then my internal voice is completely focused on the people in the room and reading all those signals that help me help them learn or move forward. When I am speaking from inside the content, I can respond in the moment to the context. Then it’s all happening in real time.”

2. Margrethe Vestager: Reading between the Rules

It’s dangerous to just enforce rules without an understanding of consequences and opportunities.

In 2014, Margrethe Vestager was appointed the European Commissioner for Competition, head of the European Union’s antitrust agency. She received a flurry of press in 2015 for taking on Google in Europe and Gazprom, Russia’s state-owned gas behemoth. Though Vestager is an experienced politician after twenty-eight years in Danish politics, she is anything but a bureaucrat.

“In a bureaucratic system, data is very abstract—mostly numbers and reports,” she told me. “The data is well done technically, but it is very hard to get any feel for what kind of human situation underlies the documents. What is really going on for people?”

She sees her work as a constant dance between generalities and specifics. The EU—and her role in particular—is constructed around enforcing rules. But without a granular understanding of the particularities in each and every situation, she is at risk of making huge mistakes.

“The system is set up to deal with things in general ways, but I need to make sure we counterbalance that,” she explained. “That’s why I never make any decisions solely based on, say, economic data. I need to feel it too. I don’t see this as an irrational process. I see it as a helpful way to circle around something and perhaps understand with my gut and my humanity as well as with my head.”

Vestager recently started to investigate Italian state support for the steel producer Ilva. With funding from the government, Ilva was able to revamp its steel plant in Taranto, Italy. This public support allowed the steel company—the EU’s largest—to optimize its resources: projections put the Taranto factory’s future production on par with the steel industries of Bulgaria, Greece, Hungary, Croatia, Slovenia, Romania, and Luxembourg combined in 2015.

Considering Europe’s recent job losses in the steel industry as a result of the glut of cheap Chinese steel on the markets, Vestager’s call seems straightforward: Italy’s state support of Ilva is against the rules of free competition. It’s an open-and-shut case.

For Vestager, however, judgments are never either/or. She works within a continuum, envisioning her role of enforcer as more of a barometer of ever-shifting political dynamics. “If you close down a plant with fifteen thousand people, you impact the whole area,” she told me. “If you don’t have an understanding of the people, the area, and, most important, the capacity for the area to change, you might end up decimating the area’s economy. It’s dangerous to just enforce rules without this understanding of consequences and opportunities.”

Vestager relates to these rules the way great chefs relate to recipes. Instead of rigidly clinging to her mandate, she exercises something much more fluid. Her judgment transcends the abstract guidelines as she fully immerses herself in each and every specific context. She is able to do this, in part, because she has so many decades of experience in the political arena, where alliances and constituencies are constantly shifting. But she also utilizes analytical empathy to better understand worlds like the one in Taranto, Italy.

“The best way for me to connect to people is to be amidst them, feeling what they do and what they can do. But the second best way to connect is to read their fiction. I can understand what it feels like to be a young immigrant when I read fiction about growing up in the outskirts of Paris. And there is excellent fiction out there exploring the experience of Albanian refugees in Italy. It doesn’t matter that these are works of fiction and hence less scientific than the numbers and reports. They describe a human experience and that is what makes them true.”

The challenge for Vestager is to stay vigilant about gathering this type of data in the midst of the bureaucratic culture in Brussels. “Because of my job,” she said, “I am protected against reality. It really shouldn’t be that way. I should be deeply embedded in reality.”

In an effort to dismantle some of the mechanisms of bureaucracy, she made immediate changes to the layout of her new offices when she arrived in Brussels. Not only was she surrounded by layers of assistants and aides—blocking out the real-world knowledge she needed to serve her electorate—the very placement of her work desk was keeping her at a distance from her work.

“There is a table—a huge one—between me and them. This is the language of power. But the problem is twofold: I don’t get any feel for what people do, want, or need because my sensitivity is blocked, and they don’t need to take responsibility for what they say, because they are put in a situation where we are not equals.”

Vestager refers to this as the “gulf of veneer”: the distance bureaucracy puts between people with differing positions of power. She moved her desk sideways so that she was immediately in direct contact with her visitors, diffusing the dynamic. Now she gets full access to them and they get full access to her.

“In a way it is much tougher on them. If they talk to me and they feel they are equal to me, they also need to take responsibility for what they are saying. I am naturally the one with the ultimate responsibility and I accept that, but if we are two people talking to one another on equal terms, what they say can’t be hidden between anything.”

As Vestager works to build the EU’s case against tech giants like Google—first arguing that their search business was artificially excluding rivals and now going after Google’s mobile operating systems—she is always taking the temperature of the governing bodies around her as well as of the culture at large. In this way, she is immersed in the whole of the political system; she feels it as a part of her body.

“When the ministry or the people affected aren’t ready, it feels like my muscles are tense. If it is the right time to do something, however, I feel like I am standing on a beach looking out on the ocean. Total openness and completely at ease. It sounds strange, but it is crucial to success that you are open to feeling at one with the people you deal with. You must empathize with their life and concerns. That means you really must walk in their shoes.”

3. Chris Voss: Understanding the Antagonistic World

We had to acknowledge their culture to transform the relationship from a manipulation to a collaboration.

On January 7, 2006, a young American journalist named Jill Carroll was kidnapped in the Adel district of Baghdad after being ambushed by masked gunmen. Carroll’s driver managed to escape, but her interpreter was shot dead on site and then abandoned. News of Carroll’s kidnapping—the thirty-first such attack on foreign journalists during the war with Iraq—was met with international alarm and an outpouring of support.

Nothing was heard from Carroll for close to two weeks and then, on January 17, Al Jazeera showed a video featuring her. Jill Carroll’s voice had been edited out, her head was uncovered and her hair disheveled, and there were two men all in black with masked faces standing on either side of her holding guns. A third man was standing directly behind her—also in black with a masked face—holding a book above her head. The video demanded that all the women in Iraqi jails be released within 72 hours, or Carroll would face immediate execution.

In a moment of crisis like this, the FBI calls upon a team of highly skilled negotiators to navigate the next steps. Chris Voss, an FBI agent for more than two decades, was the lead international kidnapping negotiator in the FBI’s crisis negotiation unit. He remembers the moment he saw the first released video of Carroll. Because of his years of training, he was immediately able to decode its message.

“When the case started, it looked really bad,” he told me. “In that video, it was clear that they had already passed judgment on her. The guy is standing behind her with a book, and that is communicating that she has been tried and convicted by a higher power. They are framing this not as a murder, but as a justified execution by a state.”

As in all of Voss’s negotiations, his first priority in the Carroll case was to determine who, exactly, is negotiating with whom. He described the kidnappers’ demand as a setup because there was no realistic way for the Americans—or anyone—to assess how many women were in the Iraqi jails, much less determine whether they might be freed in a matter of only days. The audacity of the request was the first warning sign to Voss that the kidnappers were not, in fact, negotiating with anyone in the West.

“We are not the audience for that video. They are speaking to the undecided in the Middle East. Because of that, our next step had to be a way of communicating that resonated with that same group of people.”

In this type of delicate negotiation—orchestrated primarily through the theater of the media—many of the challenges revolve around effectively coaching family members in the messages delivered to the press. These messages are then broadcast out across the world.

“By the time we worked on the Carroll case,” Voss explained to me, “we had come to develop an understanding of the cultural themes that mattered most to these insurgents in Iraq. We had to acknowledge their culture if we had any hope of transforming the relationship from a manipulation to a collaboration.”

For Voss, this transformation always begins and ends with active listening; he calls it our most underutilized tool in solving complex social problems. But active listening is only possible when we engage with a particular kind of empathy. We can liken this to the analytical empathy I described in Chapter Four.

“It’s almost easier to say what this type of empathy is not: It’s not about being nice; it’s not about agreeing; it’s not about liking the other side. It is just straight observation and then an articulation of what you see. I can be empathic with Jihadi John, a terrorist executioner. It doesn’t have anything to do with approving of his actions.”

Using his experience with previous cases and his well-developed skills with this type of negotiation, Voss worked with his team to meticulously craft the right message. This approach involved sending out messages to everyone in contact with the media—including family members and politicians.

“When anyone asked us about the Jill Carroll case, we would say, ‘Did you see how they disrespected her by leaving her head uncovered? They broke their own rules.’ And then politicians, media, family, they would all say: ‘Yeah. You’re right.’ And then they would repeat this same idea about disrespect in all of their media appearances. We can’t explain our message to them. They have to discover it through us so they can repeat it with their full emotional investment.”

That media manipulation was one step in a multipronged strategy. Simultaneously, Voss’s team was working with Jill Carroll’s family and coaching them on their talking points.

“Any effective negotiation always needs to begin by expressing an inarguable truth. With an inarguable truth, no one can disagree no matter what side they are on. People always want to say, ‘She’s innocent,’ or ‘They shouldn’t have kidnapped her.’ These messages in the media are counterproductive. They are only speaking to us. We needed to speak to the undecided in the Middle East.”

Several members of the Carroll family—including her mother and sister—were not fully convinced of the merits of such a strict script. They wanted to express their fury, fear, and sadness in their own words. Jim Carroll, Jill Carroll’s dad, however, agreed. Voss knew that using Jim Carroll as the messenger would be a cue of respect to the insurgents because in Middle Eastern cultures, all honor flows through the father. He arranged for an exclusive media agreement with CNN where a cameraman could film Jim Carroll stating only his script, with no other interview questions or analysis. This video would then be sent directly to Al Jazeera.

“We coached Jill Carroll’s dad on the entire approach. We started with an inarguable truth: ‘Jill Carroll is not your enemy.’ From there, we continued to make an appeal to the viewers in the Middle East. ‘Jill Carroll had been reporting on the plight of the Iraqi people.’ And then finally Jim Carroll said, ‘When you let her go, she will go back to doing the same reporting.’”

The video went out unedited to Middle Eastern media sources. Although Voss and his team had no influence over when and where it aired, they had confidence that the insurgents would see it at some point. It was only later, upon Jill Carroll’s release, that Voss learned that Jim Carroll’s words played a powerful role in her release.

“Jill Carroll told us that when her kidnappers saw her father on Al Jazeera, they said: ‘Your father is an honorable man.’ In the Middle East, if someone says your father is an honorable man, bang. There is a shield of honor around you and everyone in your family. The very next video that they released with her a few weeks later, she is by herself and her hair is covered with a headscarf.”

A third and final video was released on February 9, 2006. In it, Jill Carroll sits in full Islamic dress. She continues to plead for support with her release, but her voice is included in the video and she sits alone with no armed men standing around her.

“In the third video, there was no sense of a threat,” Voss explained. “It was clear to me that these guys were just trying to figure out how to let her go and save face. She was calm and she looked very well taken care of. They have one hundred percent control of the content, so when we saw that video, we knew she was safe.”

On March 30 of that same year, Jill Carroll was officially released. She walked into the Sunni Iraqi Islamic Party offices in Baghdad and told officials there that she had been freed unharmed after being cared for and treated humanely during her more than sixty days in captivity.

Voss’s particular skill set synthesized an acute emotional intelligence with his experience and knowledge of the Middle Eastern culture. His success with the Jill Carroll case would not have been possible without either of those strengths. “I like to define negotiation as emotional intelligence on steroids,” Voss said. “The key to success is navigating the other person’s emotions. In a hostage situation, emotions might seem to be larger than normal, but it doesn’t mean they’re any different.”

Through his interpretive skills as a negotiator, he approached a high-stakes situation with an understanding of narrative and messaging in several different contexts: his own, the context of the American media, the context of the kidnappers, and, finally, the context of the Middle Eastern population watching the unfolding drama. He played each and every context as part of his greater orchestration: the goal of a securing a release for Carroll.

“We used to say the most dangerous negotiation is the one you don’t know you’re in. Who is a terrorist’s target by threatening an American on film? They don’t care how Americans respond. They are thinking about Jihadi John, who is now a heartthrob. They have miscreants around the globe who want to be Jihadi John. They all want to join up.”

Although there were several other media and political efforts around the globe advocating for Jill Carroll—each one a factor in her ultimate release—Carroll reported that her captors started treating her differently immediately after the video of her father was shown on TV.

“One of the most effective weapons against terrorism is the truth,” Voss stated. “The truth was that Jill Carroll was not the enemy of her captors. Her father spoke that truth, and the rest of the world repeated it.”

Becoming a Connoisseur

Sheila Heen, Margrethe Vestager, and Chris Voss have all found a way to successfully navigate their worlds with interpretative skills. To help us to understand this better, I offer up a word often associated with the fine arts or culinary endeavors: connoisseur. For our sensemaking journey, I would like to return the word to its French origins: the verb connaître means “to be acquainted with” or “to know somebody/a place.” Mastery—connaissance—is a way of navigating through a body of knowledge.

The further we go into our chosen endeavors—whether they be teaching, hostage negotiation, or politics—the more we can categorize our knowledge. Consider techniques for cooking meat. In the United States we recognize five stages, beginning with rare and ending with well-done. In France, however, the culture of meat and cooking is much richer. French chefs must navigate among nine different categories, beginning with bleu—a steak that has lightly touched a hot pan, remaining completely raw inside—all the way up to carbonisé, or extremely well-done and even leathery on the outside. There is a very important spot between rare and medium rare in French cooking—à point—that one cannot ask for in the United States. As we add more experience to our sensemaking, we discover more analytical categories. This is the process of becoming a connoisseur: it is a way of navigating through the world.

Recall Sheila Heen: her journey is characterized by an ever-increasing knowledge of the atmosphere of her students in the room. She is now able to recognize many more moods in her classroom and, as a result, she can navigate successfully toward her teaching moments. If the room is cold and quiet, filled with tired or withdrawn faces, she knows to add in some humor and playfulness. If, on the other hand, it is a room filled with defiance and anger—managers who don’t really want to be in attendance—she finds a way to align her interests with theirs. She puts herself on the same team with them and encourages them to confide their frustrations in her.

“Early on I would be attached to my notes and I was putting all my attention on how to explain the content to my students. After years and years of working with groups, I felt confident enough in the material to let the teaching come more automatically, and I could tune into the room. I could see so much more on the faces of the students. Who was paying attention and who was not, who was open to engagement with humor and who was more reticent.”

As her teaching reached a level of mastery, these analytical categories of social acuity increased even more. Heen was able to recognize not only the dynamics that existed between her and each individual student but the different relationships between the students themselves. Earlier in her career, she might have recognized someone as the leader, and another group of people as managers under that leader. Over time, these categories exploded into dozens and even hundreds of different ways of categorizing the relationship to the hierarchy within the room. Heen became a connoisseur of human relationships and social moods.

She described a moment when she was teaching to a room filled with high-powered bankers in London. “Everyone was important and there was not a lot of pecking order to the room. For that very reason, I knew I could use status and have some fun with it as a teaching tool. When I forgot to address a table in the back, I made a joke and called it the ‘remedial table.’ The entire room lit up with laughter and goodwill. It was just the right thing to say to twenty-five of the most powerful people in banking. It opened all of us up to learn from each other.”

For Margrethe Vestager, the EU commissioner, sensemaking knowledge is characterized by an increasing sensitivity to different rhythms within the whole of the political system. After two decades in politics, she can now see opportunities for possible reforms that others cannot see. And, by the same token, she also knows when she can’t move something forward.

When to do something is as important as what to do,” she explained to me. “The window to launch a new initiative or a political program is often so small. I feel my way to understand this. Are people ready for this? Can they take more change now? What emotional state will people be in when we do this?”

And Chris Voss, the negotiator, has learned to navigate through the varying emotional registers in other people’s voices. His listening skills guide him in assessing when there is openness for possible collaboration. “When you begin to get an ear for the positives and negatives implied in the conversation, you can specifically choose to reinforce the positives and diminish the negatives,” he said. “And although it might not be enough, you can always lean into it in some way. It definitely takes practice and it is absolutely a perishable skill.”

On all of these journeys, the siren song is that there will be a model or a theory of everything that will organize all of the various factors under one framework: the GPS to plug in or a satellite to provide guidance through the dark. The true connoisseur, however, understands that there is no one right answer. Navigation is not about paying attention to everything. It is about artfully interpreting something.

Heen pays more attention to the role that hierarchy plays in her teaching. When she enters a room, she is able to sense how her own status will be received and how to either diffuse that status or elevate it in order to gain traction for a better learning environment.

Vestager needs to know the secondary and tertiary consequences of her political actions. To do this, she has developed her knowledge of the EU’s system of governance as if it is an intimate friend. She can get a read on a new system she encounters and know if it is stressed out, excited, hopeful, or despondent. This knowledge guides her decisions about what types of changes are possible.

Voss is keenly aware of the nuances of manipulation. Whether he is in an investigation or a barricade situation or a kidnapping negotiation, he is always looking for windows of opportunity to shift manipulation into collaboration. He excels at getting people to talk to him without using leverage, or threatening force.

In this way, all three of these masters have cultivated a perspective from within their given craft. And it is this perspective that ultimately leads to the most defining aspect of connoisseurship: aesthetic judgment. This is where navigation becomes an interpretive art. In both the sciences and humanist endeavors, there are many possible roads to the same destination. Which one is the most beautiful? The most compelling? The most powerful? The most pleasing? An algorithm can arrive at optimization, but only a human being—an artist, a thinker, a mathematician, an entrepreneur, a politician—only someone with a sense of perspective can interpret the meaning of the destination. Masters spend their entire lives in pursuit of this interpretation. This is how they make sense of the world.

The Alchemy of Sensemaking

Just off Route 29 in California’s Napa Valley, a gray barn with the clean architectural lines of another era stands watch over several acres of St. George rootstock vineyards. A knotted rope swing hangs in front of the property, and one lone Prius is parked in the small lot. This is the Corison Winery, home to the venerable Cathy Corison, a winemaker who has been making Napa Valley Cabernet on her own terms for close to forty years.

Though the interior of the barn is humble—there is no formal tasting room, and picnic tables holding wine bottles and glasses sit side by side with wine tanks and wood barrels—Corison exudes a quiet power when she comes out to meet me. Now in her early sixties, Corison has earned her stripes in the Napa Valley community. After graduating with a master’s degree in enology from the University of California at Davis, the country’s preeminent wine studies program, she started working in the Napa Valley.

In the years following Prohibition, the wine industry in the Napa Valley consisted of a few sleepy vineyards and a lot of sweet wine. The modern wine industry as we know it began to emerge in the mid-1960s, supported by research done at the University of California. Then, in 1976—right after Corison showed up in Napa—the wine world, dominated by the French, was stunned when California’s wines bested their French counterparts in a blind tasting with French wine critics. Napa Valley became a hotbed of activity with the emergence of new wines and new ways of making wine. Unlike the traditional European vineyards, American winemakers fully embraced technology like cold fermentation: by placing the grapes in a stainless steel vat with double walls, the winemakers were able to pass a coolant through them to control the fermentation, leading to fresher and crisper American white wines.

Corison came of age when these types of new technologies were emerging. She and her fellow UC Davis graduates initially approached winemaking through the lens of their technical training, holding the older growers in disdain for their lack of scientific knowledge. Now, four decades later, Corison sees things differently. “There was a lot of wisdom from the old-timers. We were full of ourselves, but the more you know the less you know.”

By the late 1980s, Corison had been making wine for the famous label Chappellet for close to a decade. The vineyards of Chappellet, up in the hills of Napa Valley, had gone through a few seasons of drought, so Corison and her team sourced some additional grapes from down on the Rutherford Bench. This “bench” is made up of well-drained alluvial soils, unlike the rocky terrain up in the hills. Most important, the bench is gravelly loam—composed of roughly equal parts of sand, silt, and clay—so it has great water-holding capacity but excellent drainage. Vines in loam soil get the water they need to grow in the spring and summer. Gravel makes the soil well-drained so when the rains stop coming, the vines stop growing and focus on ripening.

“If Cabernet is growing when it ought to be ripening its fruit, it maintains green flavors,” Corison explained. Ripeness in Cabernet Sauvignon is marked by the evolution of red, blue, purple, and black fruit flavors and the disappearance of green notes. “If the vine stops growing and gets busy ripening, however, there is a chance to get grapes fully ripe without the sugars getting too high.”

When Corison and her crew began sourcing grapes from these alluvial loam soils, she had a revelation about the kind of wine she wanted to make. “There was a wine inside me that needed to get out,” Corison told me. “That’s the only way I can describe it. It was both powerful and elegant. Cabernet is going to be powerful no matter what you do, but it’s way more interesting to me at the intersection of elegance. When we sourced grapes from down in the valley, I learned that this wine that needed to get out grows on the Rutherford Bench.”

Starting in 1987, Corison embraced this vision and began making her own wines. She found wineries with excess capacity and used their facilities to create her Napa Valley Cabernet. In 1995, she and her husband bought a small plot of land that runs from Rutherford to St. Helena. Everyone else had turned down the land because they assumed that the vines would need to be replanted and the old property on it torn down. Corison and her husband forged ahead, turning the derelict property into a barn to house their facility. And they did not replant the old vines on St. George rootstock. Instead, they celebrated them.

“Those vines are just wise—they are old and wise. I think it has to do with root depth. They come through heat spells with grace and style when all the younger vineyards are really hurting. They know what to do.”

During this time, the fashion in Napa Valley was big and bold. New World winemakers in California tended to let the fruit sit longer on the vine for powerful aromas and flavors. The alcohol levels of these wines began to stretch well above 14 percent. Some critics lauded them as “lush,” while others derisively referred to them as “fruit bombs.” In the late 1980s and early 90’s Napa Valley looked less and less like an agricultural community and more and more like a playground for the rich and famous. The lushness of the wines reflected the grandiosity of these drinkers.

The “numbers” of these more robust wines were all scientifically correct. The wines were all technically sound, with structural integrity. The winemakers could clearly state the properties of their “ripe” wines: the sugar, acid, and pH levels of the grapes all measured in an appropriate range.

The aspects of ripeness, however, tell a much more nuanced story. “Ripeness happens at different numbers every year,” Corison explained. “If you are not out in the vineyard, seeing it, you don’t really know. Numbers are just a piece of it. The vines get tired by the end of the ripening season and can give up after a while. And when they give up, true ripening ends. That is the challenge: to make all the components converge at just the right time. A great vintage is when all those factors converge right where you want them. It’s biology and chemistry, but also alchemy. There is so much we don’t understand on a technical level.”

Care

Every single word Corison uses to articulate her wine and her winemaking conveys her relationship to the land. These vines are not measured in scientific properties: the pH, salinity, and lime content of their soil suitability, for example. Instead, she describes them as “old and wise,” with “grace and style.”

“We have all the heat and sunshine we need to get the grapes right—even in a cold season like 2011—but because of the cold nights and the fog coming in, we have beautiful natural acidity too. And the tannins in [this] corner of the world come in feeling like velvet. If you were to measure the tannins, you’d get a very big number. But tannins are not one molecule; they’re a class of molecules that can range from harsh and astringent to soft and velvety and beautiful. And that is what I love about benchland fruit: there are fruit flavors, but the tannins are so luscious. They feel good.”

Corison could never gain this type of perspective from a spreadsheet or an office on the 87th floor of a skyscraper. She knows the tannins feel like velvet because she has been tasting them for close to forty years. Ultimately, she can hold this aesthetic judgment because of how specifically she is situated in her context. To put it simply, Cathy Corison gives a damn: “I cut my teeth on European wines. And I tasted enough of the old Cabernets from that neck of the woods to know elegance. It’s a moral imperative for me to make a wine that will be long-lived and do interesting things in the bottle.”

When you have a perspective—when you actually give a damn—you intuitively sense what’s important and what’s trivial. You can see what connects with what, and you know the data, input, and knowledge that matter. Caring is the connective tissue that makes all these things possible.

Conversely, a lack of care is often at the root of many of the business and organizational challenges I encounter in my consulting. Over time, as management has become increasingly professionalized, you can sense a kind of nihilism or loss of meaning in the executive layers. This nihilism is strongest in large corporate cultures where management is seen as a profession in and of itself, with no strong connection to what the company actually makes or does. What happens when satisfaction in work comes from managing—reorganizing, optimizing the operation, hiring new people, and making strategies—and not from producing something meaningful? How do you feel when it doesn’t really matter whether you make beauty products, soft drinks, fast food, or musical instruments?

Without care, everything is “correct” and nothing is “true.” Martin Heidegger claimed that care—or what he called Sorge—is the very thing that makes us human. He didn’t mean “care” as an explicit emotional connection with things or people, but rather in the sense that something matters to you, is meaningful to you. It is this care that enables us to interact with stuff in very complex ways, and it is also this care that enables us to see new ways of interacting with the world.

If you are in the beauty business, you simply can’t make sense of cultural insights regarding beauty ideals if you don’t care about the meaning of beauty products. If you are in the car industry, you have to care about cars and transportation—otherwise, the human phenomenon of driving will not make sense to you. Without care, you stop seeing the bigger picture of meaning and insight and you only see discrete data points—what Isaiah Berlin referred to as “so many individual butterflies.”

Care is what allowed Cathy Corison to hear the call of the wine trying to “get out” of her. And care is what gives her the courage to continue to make it, year after year after year. Today it is in fashion. Ten years ago, it was not. Care provides her with a North Star so she doesn’t get distracted or waylaid throughout these cycles of wine and culinary fashion.

Consider Leo McCloskey, founder of a wine consulting group called Enologix. Whereas Cathy Corison’s wine is never just about the numbers, McCloskey has developed an entire business model around the belief that winemaking is all about numbers. With the world’s largest wine database, he tastes hundreds of wines a year and then breaks all of them down into the individual compounds that give them their unique color, flavor, and fragrance.

What does he do with all this information? He begins by running computer tests for his clients to help determine the most important moment of the season: when to pick the grapes. This reverse-engineers the wines, stripping them down to their component parts and atomizing each and every element. These results get compared with his vast database—calculated along with captured data about conditions in the vineyard, such as the rainfall and water levels and winemaking process details like the types of barrels used and the length of fermentation. All of these models give winemakers a way to create virtual versions of their wine: playing with different factors to tweak particular elements, akin to creating a Fantasy Football League. When the wine is ready to go in the bottle, Enologix has one final offering: their calculations can predict with a fair amount of accuracy how the wine will score on the infamous 100-point scale in Wine Spectator.

It’s a Moneyball approach to winemaking, an audacious move in a culture that holds firmly to its identity as an artisanal craft. McCloskey does not reveal the names of his clients, but he primarily serves the smaller vineyards attempting to stay close to the traditional methods of winemaking made famous in Old World cultures like Burgundy and Alsace. These clients, and several sources in the industry, believe that McCloskey has something valuable to offer winemakers. But anyone who spends time with Cathy Corison knows that this value is a mirage. Nothing in McCloskey’s “black box” has any lasting point of view. By taking an entirely objective approach to the data—and treating the compounds in a bottle of wine as atomized elements discrete from their greater context—McCloskey has every chance of helping to make good wine today. But he will never come close to making great wine that endures. This is because there is no integrity, no aesthetic—there is no person who cares—behind the choices. It is technical precision with no soul.

If Cathy Corison tried to game her bottles using a data-crunching algorithm in the Enologix system, she might optimize a single year for a better wine score. But it would be at the cost of a much more compelling—and impressive—trajectory. “One of the things I love about wine is that it speaks of time and place, and marches forward speaking of time and place. These wines are still talking about what was happening,” Corison told me. “I feel a moral obligation to make wines that let the dirt speak.”

By making such wines for thirty years, Corison’s vintages have remained remarkably consistent over the years. She doesn’t add acid, tannins, enzymes, or any of the oak flavors. The wine that was dying to get out of her was based entirely on the grapes themselves. When you drink Cathy Corison’s wine, you are experiencing everything she cares about: a profundity of data that can never be captured in an algorithm. Machine learning can never understand how she prevailed despite falling in and then out of style. And entering all the sense data possible wouldn’t get at the meaning of her perseverance. Computers simply do not give a damn; they will never understand that caring is the whole point.

Meaningful Differences

Great philosophers like Martin Heidegger, Albert Borgmann, and Hubert Dreyfus argue that the kind of skill exhibited in the mastery displayed by Heen, Vestager, Voss, and Corison is the navigational skill of finding a perspective. At the heart of this navigation is a phenomenon they call meaningful differences.

To help understand this concept, first try to imagine a world without meaningful differences. This is the world of nihilism I described in corporate cultures that have lost their way. When we experience the world as lacking in meaningful differences, everything and everyone is merely a resource to be optimized. Resources are so fungible, they can be used to any end. Cathy Corison’s grapes can be interchanged with steel from Margrethe Vestager’s Italian factory. The extension of this understanding is that humans themselves are resources, hence the term human resources.

In perhaps his best essay, “The Question Concerning Technology,” from 1954, Martin Heidegger describes this modern ideology, our world without meaningful differences. He cites technology as our modern way of “Being,” our lens on the world. But his use of the word technology has very little to do with devices or other technical inventions. Technology—or technicity, as he calls it—is the logic that pervades our entire existence. Whereas Romans, or pre-modern societies, saw God’s work in everything; and the Enlightenment thinkers felt that we humans were rulers of the universe, Heidegger argues that technology, today, is now at the center of our being. Not only has it replaced the gods, it has also replaced us.

In Heidegger’s world, the spirit or logic of technology is “optimization”: the relentless pursuit of squeezing every bit of value out of physical matter around us—including trees, water, and even people. Two hundred years ago, a carpenter would look at a piece of wood and work with it to make the finest creation possible—a door handle, say—given the grain and texture of that particular piece of wood. Today, however, we optimize wood by making all wood into wood pulp and reassembling it again as standardized, non-unique, and perfectly flexible “wood.” In Heidegger’s mind, this is the invisible structure that is ordering the reality of our world today: we standardize, optimize, and make things available and flexible.

In a Silicon Valley state of mind, we experience the malaise that Heidegger characterizes across all aspects of our daily lives. Everything is available; everything is equivalent to everything else: every day, hour, and second are the same as every other day, hour, and second. We are no different from all the other cogs and widgets being shipped here and there in the transportation system. Our school system is built to create flexible accountants that are interchangeable and available for use and optimization. Companies and governments can take in new people or throw them out again with great ease because everyone is trained in the same methods by the same institutions. Technology is what makes our existence so flexible, but it is also what makes it so easy to manipulate and then to dispose of. This is progress. Or is it?

Masters like Heen, Vestager, Voss, and Corison have a very special role to play in this age of technology. Their acts of phronesis—engaging in their worlds with a knowledge and experience that is necessarily context-dependent—work to dispel the modern malaise. They are not fungible resources in the global system of goods. Instead, they respond to the call of their worlds.

Hubert Dreyfus, professor of philosophy at the University of California, Berkeley, further explained the unique role of these kinds of masters to me: “When we finally understand mastery and this calling of the world, then we understand that the source of meaning in our lives isn’t in us, as the Cartesian model suggests—it is in being in the world. When people are doing a skillful thing in the world, they lose themselves. The distinction between the master and the world disappears. Seeing what masters can do, and what we can do, we can all bring out what is best in ourselves.”

With their craft, these masters give us a glimpse of what it is to transcend ourselves. But this type of journey takes courage. “Risk is absolutely important in acquiring any skills,” Dreyfus told me, “because you have to leave the rules behind and leave behind what one generally does and stretch out into your own experience of the world. What distinguishes between risks we’re interested in and mere bravado is whether the risks are taken in the interest of what one is committed to, what one has defined themselves in terms of, and what makes the meaningful differences in their life. That kind of a risk is a necessary step in becoming a master at anything.”

In other words, you will never see meaningful differences unless you actually give a damn. Do you?