“We’ve been engaged in a failed policy with Cuba for the last fifty years, and we need to change it,” Barack Obama declared as a presidential candidate in 2007. Just last November, Obama reiterated to his Cuban-American supporters in Miami: “The notion that the same policies that we put in place in 1961 would somehow still be as effective…in the age of the Internet and Google and world travel doesn’t make sense.” For six years, President Obama has been saying that US policy toward Cuba needs to change, but for six years he’s been unwilling to take the political risk of sitting down at the negotiating table with the Cuban government to make it happen.

Despite rampant rumors in Washington that administration officials at the “highest levels” want to break the stalemate in relations, no major breakthroughs have occurred. If Obama really wants to revamp fifty years of failed policy, he’d better act soon, because time is running out.

To his credit, Obama’s policy of expanding connections between US and Cuban societies has been hugely successful. In 2009, he lifted virtually all restrictions on Cuban-American travel and remittances, leading to a rapid expansion of both. In January 2011, after the midterm congressional elections, he reopened educational travel for non-Cuban Americans, restoring the broad people-to-people travel category that President George W. Bush had abolished.

But when it comes to state-to-state relations, Obama’s Cuba policy has been much less forward-leaning. Washington’s dialogue with Havana has been limited to minor issues of mutual interest: Coast Guard search and rescue, oil-spill containment, restoration of direct postal service. Clearing the underbrush on such secondary matters could build confidence for talks on the central issues dividing the two countries, but thus far the political will to make that leap has been lacking.

Obama can’t dodge the Cuba issue much longer. The Seventh Summit of the Americas, scheduled for Panama next spring, will force Cuba to the top of the president’s diplomatic agenda. Washington blocked Cuban participation in the first six summits, on the grounds that the participants had to be democracies. At the last summit in Cartagena, Colombia, however, the Latin American heads of state warned Obama that there would be no seventh summit unless Cuba was included. Despite US objections, on September 18, Panamanian foreign minister Isabel Saint Malo traveled to Havana and issued a personal face-to-face invitation to President Raúl Castro.

Castro, who took over from his ailing brother Fidel in 2006, has already indicated that Cuba will attend. Obama now faces a decision: either participate in a summit that includes Cuba, or else boycott it and do enormous damage to US hemispheric relations. Early signals from inside the administration suggest that Obama will participate.

As the summit approaches, the real issue will be whether the administration treats Cuban participation as a domestic political problem to be finessed or as a diplomatic opportunity to break the bilateral stalemate. Conservatives in Congress and in Obama’s foreign-policy bureaucracy will push the president to confront Raúl Castro at the summit in a way designed to irritate bilateral relations rather than improve them. Obama should resist that pressure and use the multilateral context of the summit as an opportunity to launch a sustained dialogue with Cuba—to finally make the breakthrough in policy that he has been talking about for the past six years.

If Obama decides on the latter course, there are a number of lessons he can learn from his ten predecessors, all of whom had some experience talking with Cuba. The lessons outlined below are adapted from our new book, Back Channel to Cuba: The Hidden History of Negotiations Between Washington and Havana.

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Lesson One: Even at moments of intense hostility, there have always been reasons and opportunities for dialogue.

In the midst of the 1962 missile crisis, John F. Kennedy sought to open a channel of communication with Fidel Castro. At the height of the wars in Central America, Ronald Reagan sent secret envoys to test Cuba’s willingness to de-escalate, and later negotiated a settlement of the conflict in southern Africa that led to Namibian independence and the withdrawal of Cuban troops from Angola. Henry Kissinger (under President Gerald Ford) and Jimmy Carter both opened talks with Cuba in hopes of normalizing relations. Bill Clinton reached agreements that finally normalized Cuban immigration to the United States, ending periodic migration crises.

The profound restructuring of the Cuban economy that Raúl Castro has begun makes rapprochement with the United States especially attractive for Cuba. An opening to US trade, investment and tourism would facilitate Cuba’s economic transition. Castro has repeatedly expressed, publicly and privately, his interest in opening a dialogue on all issues dividing the two countries. The current historical moment appears especially auspicious.

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Lesson Two: Cuban leaders instinctively resist making concessions to US demands, but they are willing to take steps responsive to US concerns so long as those steps come at Havana’s initiative.

During the 1970s, Fidel Castro repeatedly refused to negotiate away Cuban solidarity with ideological comrades in Latin America or Africa in return for better relations with Washington. After the Cold War, when US demands about Cuban foreign policy were replaced by demands that Cuba become a free-market, multiparty democracy, Havana reacted with indignation, insisting that this was an affront to its hard-won sovereignty.

As Cuban vice president Carlos Rafael Rodríguez said to US diplomats in 1978, “I can assure you that we would never decide anything as a function of a precondition imposed by the United States. The pride of small countries, which can even push them to make the wrong decision at times, and their feelings of dignity and sensitivity must be borne in mind.” Yet Fidel Castro released over 3,000 political prisoners in response to President Carter’s human-rights policy, in hopes of advancing the process of normalizing relations.

In 2010, Raúl Castro reached an agreement with Cuban Archbishop Jaime Ortega to release most of Cuba’s remaining political prisoners, knowing that this was an issue that Obama had mentioned as an impediment to better US-Cuban relations. He then asked the archbishop to carry a message to Washington that he was serious about wanting to improve relations.

Rather than list demands about how Cuba has to change before Washington will consent to improved relations, US policy-makers should simply take note of Cuban behavior and react appropriately when Havana acts in ways that are responsive to US concerns. Even without explicit linkage, it is possible to initiate a virtuous circle of positive action and response.

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Lesson Three: Cuban leaders have had a hard time distinguishing between gestures and concessions.

“Tell the President he should not interpret my conciliatory attitude, my desire for discussions, as a sign of weakness,” Fidel advised in a secret message to Lyndon Johnson in early 1964. The Cubans worry that even small steps on their part may be misinterpreted in Washington as weakness, as has happened more than once. Thus, Cuba wants the United States to take not just the first step toward reconciliation, but the first several.

To make matters worse, Havana discounts US gestures that serve Washington’s interests. In 1975, Ford and Kissinger decided not to oppose the decision that year by the Organization of American States to lift sanctions against Cuba, hoping Cuba would take it as a gesture of good faith. Havana instead saw it as Washington merely trying to cut its diplomatic losses in Latin America. In 2009, when Obama decided not to oppose the repeal of the 1962 OAS resolution suspending Cuba, Havana had the same interpretation. When he lifted limits on Cuban-American travel, Cuban leaders regarded it as a political debt to the Cuban-American community, not a a gesture to Cuba.

Washington, for its part, has wanted Cuba to take significant steps to give the White House political cover from domestic critics by showing that a policy of engagement pays dividends. When US gestures fail to elicit significant reciprocal steps from Havana, the White House risks looking soft. This worry preoccupied Kissinger, Carter, Clinton and Obama, making them reluctant to undertake the kind of dramatic moves that might have broken the Alphonse-Gaston stalemate.

Both sides need to adjust their behavior. Washington, as the more powerful player, should be willing to take bolder initial steps. Havana, for its part, needs to acknowledge and respond positively to those steps, even when they also serve other US interests.

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Lesson Four: An incremental approach to normalizing relations has not worked.

Kissinger tried it. Carter tried it. Clinton thought about trying it, albeit without much enthusiasm. Obama started to try it, but set unrealistic conditions.

Incrementalism has three fatal flaws. First, it is slow. Confounding issues are likely to arise that disrupt the process of building mutual confidence, making further progress difficult. Examples include Cuba’s interventions in Africa during the Cold War; the rafters migration crisis and the Brothers to the Rescue shoot-down during the Clinton administration; and Cuba’s arrest and imprisonment of USAID contractor Alan Gross during the Obama administration.

Second, incremental steps don’t fundamentally change the relationship and are therefore easily reversed. Gerald Ford lifted the embargo on trade with Cuba by subsidiaries of US corporations in third countries; the 1992 Cuban Democracy Act reimposed it. Carter lifted the ban on travel to Cuba; Reagan reimposed it. Clinton relaxed restrictions on people-to-people exchanges; George W. Bush reimposed them, and Obama relaxed them again.

Finally, although gradualism seems politically safe because each incremental step is small and therefore ought to be less controversial, an incremental approach prolongs the political fight with domestic opponents in Washington, who are no less vociferous in opposing small steps than large ones. Every incremental step gives them a new opportunity to halt the process, and they only need to win once.

The alternative is a bold stroke that fundamentally changes the relationship (even if it doesn’t resolve every issue) and leaves opponents facing a fait accompli. Nixon’s trip to China is the paradigmatic example.

The Cuban Liberty and Democratic Solidarity Act of 1996 (a k a Helms-Burton) wrote the economic embargo into law, which makes it impossible for a US president simply to normalize US-Cuban relations by himself. However, Obama has wide latitude to authorize exceptions to the embargo and use his other executive powers to significantly improve relations with Havana—including his constitutional authority to send and receive ambassadors.

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Lesson Five: Domestic politics is always an issue on both sides.

From the beginning, there have been people in both capitals interested in improving relations and those opposed. In the 1960s and ’70s, US opposition came mostly from cold warriors inside the foreign-policy bureaucracy. In the 1980s, ’90s and beyond, it came mostly from conservative Cuban-Americans. The end of the Cold War reduced the first obstacle; changing demographics in the Cuban-American community have gradually eroded the second, as demonstrated by Obama’s success in the 2008 and ‘12 elections. Today, US opposition comes mainly from conservative Republicans and a handful of Democratic members of Congress whom Obama has been unwilling to confront.

Fidel Castro made a successful political career at home and abroad portraying himself as a David doing battle with the imperialist Goliath. But Raúl Castro has chosen a different path. Whereas Fidel took a certain satisfaction in defying the United States and exploited US hostility to rally nationalist sentiment, Raúl has focused on Cuba’s domestic problems. Anti-US diatribes feature much less prominently in his speeches, and he attributes Cuba’s economic problems to the shortcomings of Cuban policy rather than the embargo. If Fidel was motivated to maintain an acrimonious relationship with Washington for domestic political reasons, Raúl is not.

In short, while domestic politics has been an obstacle to better relations in the past, the climate for progress in both capitals is better today than it has been in decades.

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Lesson Six: Cuba wants to be treated as an equal, with respect for its national sovereignty.

As Fidel said to Carter administration diplomats Peter Tarnoff and Robert Pastor in 1978, “Perhaps it is because the United States is a great power, it feels it can do what it wants…. Perhaps it is idealistic of me, but I never accepted the universal prerogatives of the United States. I never accepted and never will accept the existence of a different law and different rules.” Washington, on the other hand, has long felt entitled to do whatever realpolitik demands.

In late 1959, Havana responded to a diplomatic protest from Washington with a long recitation of the history of US domination of the island, concluding: “The Cuban Government and the Cuban people are anxious to live in peace and harmony with the Government and the people of the United States…but on the basis of mutual respect and reciprocal benefits.” This theme has echoed across a half-century of US-Cuban relations. Raúl Castro has repeated the same point over and over in offering to negotiate differences with the United States.

Yet treating Cuba with the respect due a sovereign nation has been the hardest thing for Washington to do. The long history of Cuba’s subordination to the United States before 1959 has weighed on the minds of policy-makers on both sides of the Florida Strait.

Policy-makers in Washington need to accept that Cuba in the twenty-first century will never again be the subordinate Cuba of the nineteenth and early twentieth. Policy-makers in Havana need to trust that reconciliation with the United States is possible without putting at risk Cuba’s national independence, which they made a revolution to secure.

In a century when the most pressing problems transcend national boundaries, near neighbors cannot afford perpetual hostility. With every passing day, Cuba and the United States become ever more closely intertwined: as Cubans buy wheat from US farmers in the Midwest; as Cuban and US citizens travel more freely back and forth; as Cubans and Cuban-Americans knit back together the cultural, financial and family ties severed after the revolution in 1959.

The history of dialogue between Cuba and the United States since then demonstrates that it is not only possible to replace sterile hostility with reconciliation, but that such a course of action will serve the vital interests of both nations.

José Martí, whose eloquently expressed suspicions about US imperial designs on Cuba inspired Fidel Castro’s nationalism, nevertheless saw the possibility of a relationship based on equality. A few months before his death in 1895, Martí wrote: “There is that other America, North America, that is not ours, and whose enmity it is neither wise nor viable to encourage…. However, with firm propriety and an astute independence, it is not impossible—and indeed it is useful—to be friends.”