When Knowing Isn’t the Same as Being Ready

By September 1804, Lewis and Clark had been traveling up the Missouri River for more than four months, and they knew they were getting close to trouble. Not necessarily a fight—they couldn’t know that—but they had certainly been warned. Meriwether Lewis and William Clark were leading the Corps of Discovery, the military expedition President Thomas Jefferson sent west following the Louisiana Purchase. When they left the St. Louis area in May, Jefferson had given them a rather enormous assignment. They were supposed to explore this new American territory and learn as much as possible about the country and the people who lived there. Along the way, they were also trying to determine whether there was a practical route across the continent toward the Pacific.

Here’s something about the expedition that I think we sometimes miss. The Corps wasn’t simply wandering into the West to see what they could find. Lewis did a remarkable amount of homework before they left, and the information gathering continued once the journey began. He collected whatever he could find about the country ahead and talked with fur traders and others who had actually traveled the Missouri. Once the expedition was underway, the captains continued asking questions and comparing what they were hearing with what they already knew. If you’re about to go somewhere you’ve never been, it helps to talk to somebody who’s already been there, and Lewis seems to have understood that very well.

One subject kept coming up in the intelligence they collected. They were going to encounter the Sioux. Years earlier, a trader named Jean Baptiste Truteau had traveled and traded along the Missouri, and his experiences involving the Sioux had not always been pleasant. He described the Teton Sioux in particularly hostile terms, and Jefferson had actually supplied Lewis with excerpts from Truteau’s journal in 1803.

There were other sources available as well. James Mackay and John Evans had explored the upper Missouri for Spain during the 1790s and had brought back valuable information about a part of North America still poorly understood by most Americans. Lewis obtained material connected with their expedition while preparing around St. Louis, and Mackay himself was available in the area.

Lewis even developed a systematic set of questions about the Native nations the Corps might encounter and circulated them among experienced traders. Think about that for a minute. This was 1804. Once the expedition moved far enough up the Missouri, there would be no quick way to send a question back to Washington or St. Louis and wait for an answer. The maps would become less dependable as they moved farther west. Lewis understood that the information they carried with them, along with whatever they could learn along the way, was eventually going to have to be enough.

That’s what makes the Teton encounter so interesting to me. And just to avoid some understandable geographical confusion, these were the Teton Sioux, not the Grand Tetons near Yellowstone. This isn’t really a story about leaders who failed to gather information, because the captains had plenty of it. The more interesting question is what happened to all that information after they gathered it. At some point, knowing that trouble might be ahead had to affect what they actually did when they reached it. The gap worth looking at is the distance between knowing something and actually being ready for it.

The warnings continued as they moved upriver. On May 25, only days after the expedition began, Clark received additional information from a French Canadian named Régis Loisel, an experienced trader who had operated in Sioux country. Then, near the end of August, the Corps met with the Yankton Sioux. During those discussions, a Yankton chief known to the Americans as Half Man warned them about the nations they would encounter farther upriver. He feared those nations would not be particularly receptive to the message the expedition was carrying.

That message needs a little explanation because the Corps of Discovery wasn’t traveling merely as an exploring party. Lewis and Clark also represented the United States, and Jefferson expected them to establish relationships with Native nations throughout the newly acquired Louisiana Territory. They carried gifts and other symbols of American diplomacy along with a message announcing a new political relationship with the United States. From the American perspective, France had sold Louisiana to the United States and the political situation had changed. The Native nations living there, however, already had their own political relationships and their own understanding of who held power along the Missouri. A transaction between France and the United States did not suddenly erase any of that.

Half Man’s warning therefore deserves more attention than just another interesting detail from the journey. The captains had already collected older reports about the Sioux, but this was different. Here was a Native leader with current knowledge of the political environment telling them, in effect, that the people ahead might not respond the way the Americans expected.

Three weeks later, the warning became even more immediate. On September 23, three Lakota boys swam out to the expedition and reported that a Teton encampment of roughly eighty lodges was nearby. Whatever the captains had heard about the Teton was no longer background information about people they might eventually meet. They were almost there.

This is where an idea from Mike Freedman and Benjamin Tregoe helps me understand the problem. In The Art and Discipline of Strategic Leadership, they make an important distinction between collecting information and actually turning that information into strategic intelligence. Collecting information is only the beginning. Leaders still have to figure out what that information means and whether it should change what they are preparing to do. The distinction sounds simple enough, but I’m not sure organizations are always very good at it.

Modern organizations certainly don’t suffer from a shortage of information. In fact, we can spend so much time gathering and analyzing it that the process itself begins to feel like preparation. By the end, everybody may know considerably more than they did when they started. But Freedman and Tregoe raise the harder question. Has knowing more actually changed the way we are preparing for what comes next?

Now go back to the Missouri River. Lewis had been hearing about the Sioux since before the expedition left St. Louis, and the information continued arriving as the Corps moved upriver. Some of it came from traders who knew the region. Half Man added a warning based on the situation as he understood it, and then the Lakota boys told them the Teton village was close. These weren’t identical reports, but they kept pointing the captains toward the same problem. By then, the important question wasn’t simply what they knew about the Teton. It was what all of that information should cause them to do.

On September 25, they found out.

Among the principal Teton leaders involved in the meeting were Black Buffalo, Buffalo Medicine, and a chief the Americans called the Partisan. The captains approached the meeting using diplomatic practices they had used elsewhere on the Missouri. Gifts were exchanged, speeches were made, and the Americans demonstrated some of what they had brought with them. Several Teton chiefs eventually came aboard the keelboat, where whiskey was served. That last decision would not improve the situation.

The Partisan, whom the Americans believed had become affected by the alcohol, began behaving in ways Clark considered offensive. The disagreement escalated until Clark drew his sword. Teton warriors prepared their weapons, and members of the Corps responded. After months of gathering information about the country ahead, the expedition had reached one of the groups it had been repeatedly warned about and now stood frighteningly close to an armed confrontation.

It would be easy to stop there and say the captains simply should have prepared better, but I don’t think the story is quite that simple. Preparation can reduce uncertainty; it cannot eliminate it. They knew enough about the Teton to understand that the meeting could be difficult. What no report could tell them was what would happen once these particular men were sitting across from one another. Personalities entered the equation, alcohol complicated matters, and before long the encounter was moving in a direction nobody could have predicted with much confidence. The captains had prepared for the meeting they imagined might happen. Then the real one showed up.

Chip and Dan Heath deal with this problem in Decisive, their examination of how people make decisions. One of the tendencies they identify is overconfidence. We become too certain that the future will unfold more or less the way we expect. Their answer isn’t to stop planning or predicting. Instead, they suggest that leaders “prepare to be wrong” by taking seriously the possibility that events may unfold differently from what they expect.

I like that idea because “prepare to be wrong” doesn’t mean expecting disaster. It means holding our expectations a little more loosely. The Heaths also recommend what they call “tripwires,” predetermined signals that tell us circumstances have moved far enough from our expectations that we need to stop and reconsider. Half Man obviously wasn’t providing the captains with a twenty-first-century management technique, but his warning is a useful way to think about the concept. When credible new information reinforces a risk you already know exists, at what point should it cause you to reconsider your preparation?

That question goes well beyond this particular encounter. Suppose your organization is preparing to launch a new product and a customer expresses concern. Maybe that’s just one customer. Then you hear essentially the same concern from somewhere else. Eventually you have to decide whether you’re simply collecting information or whether the information is trying to tell you something.

I’ve seen that happen in organizations more times than I can count. We hear something once and make a note of it. Then we hear it again. At some point, the issue is no longer whether we have enough information. The issue is whether we’re willing to let what we’re learning change something we’re already planning to do.

The Teton encounter adds another layer to the problem because even the best preparation has limits. Captains Lewis and Clark had learned quite a bit about the people they were meeting, but information about a group is not the same thing as understanding the individuals standing in front of you. That’s where Chris Voss, a former FBI hostage negotiator and the author of Never Split the Difference, offers another useful way of looking at what happened.

Voss treats negotiation as an ongoing process of discovery. You prepare before the conversation, certainly, and he places considerable emphasis on doing that preparation well. But preparation can only take you so far. Once the conversation begins, you have to listen closely enough to recognize when the person sitting across from you is telling you something you didn’t expect. Voss argues that assumptions about the other person should be treated more like hypotheses than settled facts. Preparation gets you into the conversation; careful listening helps you understand what is actually happening once you’re there.

I think that’s particularly useful when we return to the Teton meeting, because one of the most important things the Americans learned could only be discovered after the encounter began. As the confrontation moved toward possible violence, Black Buffalo intervened and helped keep the situation from becoming a fight. Whatever the captains had learned beforehand about Teton politics, they were now learning something very specific about the influence of the man standing in front of them. In that moment, Black Buffalo’s ability to affect what happened next mattered more than a general description of the Teton contained in an old journal.

Leaders run into the same problem in much less dramatic circumstances. Before an important meeting, most of us try to learn as much as we can about the people we’re going to meet. That’s good preparation, and I would much rather walk into the room having done it than not. But research about people can never completely substitute for dealing with the people themselves.

Once the meeting begins, you have to pay attention to what is actually happening in the room. Maybe the person you expected to have the most influence doesn’t. Maybe someone you hadn’t thought much about suddenly becomes important. That’s when you find out whether the assumptions you brought into the meeting still make sense.

What happened the following day makes the point even better. After the armed confrontation, the Americans were welcomed into the Teton camp, where the atmosphere was remarkably different. At one point the captains were carried ceremonially on buffalo robes and seated beside Black Buffalo. Think about the change in scene. One day Clark had his sword drawn while armed men faced one another; the next day the captains were being carried into a ceremony on buffalo robes.

That doesn’t mean all the problems disappeared. The political differences between the Americans and the Teton remained, and the relationship was still complicated. But the contrast between those two days tells us something important about the danger of deciding too quickly that we understand a situation. Preparation can’t simply be something we finish before action begins because some of the most useful information becomes available only after the encounter is underway. The captains could prepare for the Teton meeting, but there were things they could learn only by sitting down with the men themselves.

That’s why I think the Teton story gives us something more useful than the familiar advice to “do your homework.” The captains had done their homework, and they had continued learning as they traveled. Their problem was harder than simply knowing enough. They had to figure out what all that information meant for the encounter ahead and then be willing to change their thinking once the people they had been studying were actually standing in front of them.

Freedman and Tregoe help us understand why information has to become judgment before it becomes strategically useful. The Heaths take us one step further by reminding us that even good judgment can’t make the future predictable. Then Voss brings us into the encounter itself, where preparation has to be joined by the willingness to keep listening. Taken together, those ideas help explain something the Teton meeting makes unusually visible. Preparation is not finished simply because the research is finished.

The more I look at this encounter, the less interested I am in asking whether the captains knew enough. They knew quite a lot. The better question is whether what they knew had sufficiently shaped what they were prepared to do, and whether they were ready to keep learning when reality turned out to be more complicated than the information they had collected beforehand.

Organizations face that same problem every day, although fortunately most of us aren’t trying to solve it with Clark’s sword in one hand. We can study a situation carefully and still discover something important five minutes into the meeting. Knowing that a problem is coming doesn’t mean we know what it will look like when it arrives. And sometimes the person sitting across the table turns out to be very different from the person we thought we understood beforehand.

So think about whatever significant issue is sitting in front of you right now. Chances are you already know quite a bit about it. What I would want to know is whether any of that information has caused you to prepare differently. If it hasn’t, it’s worth asking whether the information has confirmed what you already planned to do or whether you simply haven’t allowed it to challenge the plan yet.

Eventually every report ends, somebody closes the laptop, and the meeting begins. That’s essentially what happened on the Missouri in September 1804. Months of research and warnings had brought the Corps to the Teton, but none of that information could manage the encounter for them. Once the two sides were standing face-to-face, the captains still had to understand what was happening in front of them and respond to a situation that was changing by the minute.

That’s when knowing becomes something else entirely. That’s when you find out whether you were actually ready.

1. What information do you currently have that has not yet changed how you are preparing?
2. What concern have you now heard from more than one credible source, and what—if anything—has changed because of it?
3. Who are you relying on? Research, reputation, or someone else’s description? What are you learning from the person directly that might change your understanding?
4. Who actually has influence over the situation you are dealing with—and how certain are you that you have identified the right people?
5. What have you learned since your current plan went into motion that you could not have known beforehand?
6. Where might you be following the preparation you made rather than responding to the situation you actually have?