When Donald J. Trump first campaigned for president eight years ago, tech executives largely ignored him. They later atoned for their disregard by making a televised walk through the lobby of Trump Tower in New York for a 90-minute meeting with the president-elect.
This election cycle, tech leaders have tried to avoid making the same mistake. Executives such as Mark Zuckerberg, Tim Cook and Sundar Pichai started reaching out to Mr. Trump directly in the weeks and months before the first ballot was cast.
They flattered him. They shared their troubles. They criticized his opposition. They emphasized common enemies.
The change in strategy speaks to what business leaders learned during the first Trump presidency and illustrates how they have adapted their approach before Mr. Trump returns to the White House. Believing that his political positions are fluid and his actions are often transactional, they are forging direct relationships they hope will benefit their businesses.
In his first term, Mr. Trump criticized tech companies for manipulating coverage of him on their platforms and opposing his agenda. He was punitive with those he considered antagonists. In one instance, Amazon accused Mr. Trump of pressuring the Pentagon to cancel a cloud computing contract with the company because its founder, Jeff Bezos, owned The Washington Post.
But Mr. Trump heaped praise on Mr. Cook, the chief executive of Apple. He liked that Mr. Cook called him directly to discuss business and economic issues. Such direct engagement helped Apple avoid tariffs on many of its products, even as the Trump administration cracked down on other companies that were manufacturing in China.
This time, tech chief executives have been following Mr. Cook’s playbook. Mr. Zuckerberg, the chief executive of Meta, spoke to Mr. Trump after an attempted assassination in July. Mr. Pichai, Google‘s chief executive, told Mr. Trump that his campaign stop at a McDonald’s restaurant was one of the biggest things ever on Google. And Andy Jassy, the chief executive of Amazon, introduced himself with a phone call, while Mr. Bezos, his predecessor, called Mr. Trump to praise his resilience after the July shooting.
The executives never offered a public endorsement, but after Mr. Trump’s victory on Tuesday, they feted him with congratulations on X. Mr. Cook, who was typically the last of his peers to weigh in on hot-button issues during the previous Trump administration, offered the final word, saying: “Congratulations President Trump on your victory! We look forward to engaging with you and your administration.”
Jeffrey Sonnenfeld, a Yale management professor who has advised executives and Mr. Trump over the years, said the direct outreach and quiet wooing of Mr. Trump were “the right thing” to do, noting the executives’ responsibility to shareholders to have a relationship with whoever is in the White House.
“They were building a rapport,” he said. “And that’s the right way to do it — establish personal eye contact and get a foundation for the future.”
Meta and Google declined to comment, while Amazon and Apple didn’t respond to requests for comment. Some of the details of their chief executives’ outreach were shared by Mr. Trump during several podcasts and an interview with New York magazine. Others were reported previously by The New York Times and The Washington Post.
The tech titans’ private outreach to Mr. Trump has contrasted with the public embrace by Elon Musk, the chief executive of Tesla, and many of Silicon Valley’s chatterbox venture capitalists. Mr. Musk hit the campaign trail for Mr. Trump in Pennsylvania and turned his personal feed on X into a Trump-advocacy channel, while venture capitalists donated generously to Mr. Trump’s campaign in hopes his administration would be more friendly to their pet causes — crypto, antitrust and taxes — than President Biden’s has been.
These prominent investors were ebullient on social media Wednesday morning. When Mr. Musk posted that America’s “nation of builders” would soon be “free to build,” Marc Andreessen, a prominent investor who donated to Mr. Trump’s campaign, responded with his catchphrase, “It’s time to build,” with an American flag emoji.
In reaching out to Mr. Trump, tech executives were doing more than hedging their bets ahead of a tossup election. They were also laying the groundwork for improved relations between Silicon Valley and Washington.
The relationship between some of the tech leaders and the president quickly deteriorated after that 2016 Trump Tower meeting. Just weeks into Mr. Trump’s presidency, some of them criticized his executive order temporarily blocking immigration from seven Muslim-majority countries. Sergey Brin, one of the co-founders of Google, was spotted at a protest against the measure at San Francisco’s airport.
Silicon Valley’s revolt sowed tension with the Trump administration. The fraught relations continued when Mr. Biden took office in 2021.
The Biden administration put tech on its heels with aggressive antitrust action and a crackdown on mergers and acquisitions. Over the past four years, the Justice Department and Federal Trade Commission have filed antitrust lawsuits against Amazon, Apple, Meta and Alphabet, the parent company of Google. The cases have threatened their businesses, especially Google, which was ruled a monopolist.
The F.T.C. has also cracked down on mergers and acquisitions and announced an inquiry into investments by tech giants in artificial intelligence start-ups. The agency’s scrutiny has been criticized by venture capitalists and others for slowing deals in Silicon Valley and stymieing traditional opportunities for big companies to grow.
Mr. Trump has said the leaders of those companies have expressed a readiness to turn the page on such regulatory headaches. He has been receptive to their appeals, listening sympathetically as Mr. Cook complained to him on a call last month about European regulators.
“I’m not going to let them take advantage of our companies,” Mr. Trump recalled telling Mr. Cook, during a podcast interview last month. “That won’t be happening.”
Mr. Trump has also voiced skepticism about the possibility that the government might break up Google, saying he considered it a bulwark against China’s technology ambitions. Though the president-elect has criticized the company over the years for how its algorithm ranks news articles about him, he expressed concern that weakening the company could be dangerous at a time of international tech competition.
Those softer regulatory positions have lifted hopes across Silicon Valley that Mr. Trump might replace Lina Khan, the chair of the Federal Trade Commission, who has sought to block mergers, and Gary Gensler, the Securities and Exchange Commission chief, who has antagonized the crypto industry.
Ms. Khan’s term has expired, and Mr. Trump will have to decide whether to keep her. She has won accolades from Vice President-elect JD Vance, who has praised her for being willing to go after big tech companies. But his views will be only one of many entertained by Mr. Trump, who has a history of courting competing opinions on issues before making final decisions.
By directly engaging with Mr. Trump, tech executives are increasing their chances of convincing him what action to take and possibly influence Ms. Khan’s replacement, said Adam Kovacevich, chief executive of Chamber of Progress, a tech policy group that is backed by companies including Amazon and Apple.
“We know he’s susceptible to the last person in his ear,” Mr. Kovacevich said. “His style of management hasn’t changed, but he may be more knowledgeable about what to prioritize.”
Mr. Sonnenfeld said tech executives’ approach in recent months shows that they understand the value of staying united on issues. In the past, Mr. Trump sought an advantage in negotiations by pitting competitors against each other, like General Motors and Ford Motor. But the way tech executives have reached out to him directly with similar messages suggests that they understand the value of consensus.
“Trump will bulldoze you if you are too sycophantic,” Mr. Sonnenfeld said. “Collective action is needed to avoid being victimized.”
Erin Griffith contributed reporting from San Francisco.