AI-generated historical illustration of Joseph Gravelines communicating with Arikara leaders along the Missouri River, circa 1806. Created with OpenAI ChatGPT for Nick Walters, Finding Your Way (2026). Artistic reconstruction; not a depiction of a documented meeting.
One of the hardest things a leader has to do is deliver a message that someone else doesn't want to hear. It might be announcing a difficult decision, explaining a change in direction, or telling someone that things aren't going to work out the way they had hoped. Sometimes the message is perfectly reasonable, supported by the facts, and even necessary. But that doesn't mean the person receiving it is going to accept it.
We often approach these conversations by concentrating on what we're going to say. We rehearse our explanation, organize our arguments, and prepare to defend our decision. But how much time do we spend thinking about the person on the other side of the conversation?
In his book Never Split the Difference, former FBI hostage negotiator Chris Voss argues that effective negotiation begins with what he calls tactical empathy. It means making a deliberate effort to understand another person's perspective, recognize their concerns, and demonstrate that you understand them. It doesn't require agreement, and it certainly doesn't mean abandoning your position. It means recognizing that people are more likely to listen when they believe they've been heard.
It's a principle that helps explain the value of one of the lesser-known participants in the Lewis and Clark expedition.
Jefferson Needed Information, Not Just Exploration
We know that Lewis and Clark struggled against the current of the Missouri River, crossed the Rocky Mountains, and eventually found their way to the Pacific Ocean. Those challenges are an important part of their story, but the expedition was about much more than overcoming obstacles.
President Thomas Jefferson wanted information. He wanted to understand the geography, natural resources, trade possibilities, and Native nations of the vast territory the United States had recently acquired through the Louisiana Purchase. Lewis and Clark were expected to gather that information and report it to the White House.
In April 1805, when the expedition continued west from Fort Mandan in modern-day North Dakota, a keelboat headed east carrying journals, maps, specimens, and other information for Jefferson. Making it to the Pacific was a long way off, but they were already delivering on part of their assignment.
Lewis and Clark carried Jefferson's messages to Native leaders, sought information about the country ahead, and attempted to establish diplomatic and commercial relationships. Those efforts also reflected American ambitions for expanding trade and influence into lands already occupied by Native nations.
The captains needed people who could do more than translate words. They needed people who understood the communities they were trying to reach.
One of those people was Joseph Gravelines.
The Man Jefferson Trusted with a Difficult Message
Gravelines was a French-descended trader and experienced boatman who had spent considerable time among the Arikara people along the Missouri River. Through years of trading, he had developed a familiarity with their language and customs that would prove valuable to the expedition.
When Lewis and Clark first met him at the Arikara villages, they recognized the value of his experience. He served as a boat pilot, guide, interpreter, and intermediary. His knowledge of the Arikara and neighboring peoples was particularly useful because the expedition's diplomatic objectives depended on relationships with Native nations.
Gravelines eventually accompanied an Arikara chief named Ankedoucharo, also known as Too Né, to Washington as part of Jefferson's diplomatic efforts but, unfortunately, Chief Too Né died while he was in the nation's capital.
This created a serious diplomatic problem for Jefferson. An Arikara chief had traveled to Washington at the invitation of the American government and died while he was there. Now Jefferson had to find a way to explain his death to the Arikara people back home and he chose Gravelines to do the job.
This wasn't simply a matter of delivering a letter. It was a potentially dangerous diplomatic assignment. The message concerned the death of one of their leaders, and the response of his people could have serious consequences for relations between the Arikara and the United States. The Arikara's reaction could also have consequences for the Corps of Discovery when they eventually returned down the Missouri River.
We don't know exactly what Gravelines said when he delivered the message to the Arikara or how he handled the conversations that followed. But we do know that he brought something important to the assignment. He knew the language, the customs, and the people who would be receiving the news.
That was an advantage no carefully worded message from “the Great Father in Washington” could provide on its own.
When the Message Is Difficult, Understanding Matters More
This is where Voss's approach to negotiation becomes particularly relevant.
Tactical empathy is not about agreeing with someone to avoid conflict. Voss teaches negotiators to recognize the other person's concerns and demonstrate that they understand them. That understanding can reduce resistance and make productive communication possible, even when the parties disagree.
We cannot know whether Gravelines used anything resembling Voss's specific techniques. But his assignment illustrates why knowledge of the people receiving a difficult message can be as important as the message itself.
Think about the last time you had to deliver news that someone wasn't going to like. Did you spend most of your preparation deciding what to say? Or did you also consider what the other person might be worried about, what questions they would have, and how the decision might affect them?
When I served as USDA Rural Development State Director in Mississippi, I discovered that the overhead costs of delivering our rural housing program were running about 35 percent. I believed that was far too expensive, so I made the decision to consolidate offices. I knew the local communities wouldn't be happy about losing their USDA offices, so I personally visited every county where an office was closing. I met with local officials, explained why I had made the decision, and answered their questions. None of them liked the decision, but they understood why I had made it. Sometimes that's the best you can accomplish when delivering difficult news.
There's a difference between explaining a decision and helping someone understand it. A leader can have all the facts and still fail to communicate effectively if the person receiving the message believes their concerns have been ignored.
The Message Is Only Half the Conversation
The Lewis and Clark expedition reminds us that its success wasn't measured only by the miles traveled or the obstacles overcome. Jefferson needed information about the country and its people, and he needed relationships that could advance American diplomatic and commercial objectives.
People like Joseph Gravelines contributed to those purposes in ways that are easy to overlook when we concentrate exclusively on the expedition's physical challenges.
Maybe before you deliver your next difficult message, you could spend as much time understanding the person who will receive it as you spend preparing what you intend to say.
Because before you can persuade, you have to understand.
Recommended Reading
Chris Voss with Tahl Raz, Never Split the Difference: Negotiating As If Your Life Depended On It (HarperBusiness, 2016).
Historical Source
Paul C. Graveline, “Joseph Gravelines and the Lewis and Clark Expedition,” We Proceeded On, Vol. 3, No. 4 (1977), pp. 5–6.
This post is part of Finding Your Way, where proven leadership ideas meet stories from the Lewis & Clark expedition. The full stories will be collected in my upcoming book, Beyond the Map. Sign up to be notified when it’s released.
