How Jen Psaki went from runner-up for the job—twice—to Biden’s first press secretary

When asked in an interview with Fortune how hard it is to speak on behalf of the president of the richest, most powerful country on earth, Psaki responded with a chuckle. “I was very fortunate, because I was the runner-up for the job twice,” she said. “I was a bridesmaid, never the bride, as they say.” 

Throughout the Obama administration, Psaki served in a variety of roles, including deputy press secretary, deputy communications director, spokesperson for the Department of State, and White House communications director.

During the Obama administration, Psaki recalled, she was the runner-up for the job behind two men who did get the job, Josh Earnest and Jay Carney. “I was sad when I didn’t get it, especially the second time,” she said. But when she finally nabbed the gig as Biden’s inaugural press secretary, “it was exactly the right time for me to do the job.” 

Trial by fire

Sure, the job is hard, she allowed. But the hardest thing is not the international pressure, or the burning-hot TV lights, or the eagerness with which some news outlets may seek to undermine or twist words. 

Rather, it’s “having the breadth of knowledge of a range of issues” in a job with a precipitously steep learning curve. “I’m grateful I [became press secretary] at that point in my career, because I had more perspective and more years under my belt of sitting in policy meetings, and having a deeper understanding of that.”

Sadly, unlike the rich tradition of a hand-off seen in earlier administrations, no one from former president Donald Trump’s cabinet made much of an effort to give Psaki any friendly guidance. “It was a bit of a different transition, to put it diplomatically,” she said. “I don’t know how else to describe it.” 

When the Trump team visited the White House shortly after Trump became president-elect, Psaki was working as Obama’s communications director. That day, she and her team had a sit-down with Sean Spicer, Trump’s first press secretary. “That wasn’t a part of my experience coming in,” Psaki said. “There were a range of things at play.” So she took initiative, personally calling a “number” of her predecessors, on both sides of the aisle. “I spoke with some Republicans,” she said. But “not anyone from the Trump administration.”

One such Republican: Dana Perino, who was press secretary for the latter half of George W. Bush’s second term. Psaki calls her a peer. “I’ve read all of her books, and though we have different positions on issues, I think she’s somebody who did the job, and I certainly have respect for that,” Psaki said. 

Honest judgment

No job comes without obstacles—or without errors. Psaki said the press secretary is “of course” allowed to disagree with the president, or push back on the messaging that he or she or their team wants.

“Your job is to speak on behalf of the president, but your job is also to be an advisor to the president and to give candid advice and disagree when warranted,” she said. “Ultimately, he’s the decider. But the best press secretaries are people who are willing to do that.” 

Naturally, being a human stand-in for a powerful politician—the commander in chief; the leader of the free world, et. al.—could be rife with potential errors that not only could reflect poorly on Psaki herself, but even up the chain, creating bad press for the entire administration.

“When I was the press secretary, [I’d] forget in the moment that, in the modern media age, nobody’s watching 45 minutes of a briefing,” Psaki recalled. “They’re pulling 30 seconds out of it, to critique. That’s just the reality.” 

As for regrets, she said only she wishes she could’ve said certain things more clearly. “Sometimes my tone wasn’t meeting the moment,” she said. “I talk in my book about moments during COVID where everybody was feeling frustrated, and [I got] questions that were maybe not aligned with what would make sense from a policy standpoint.” 

Nonetheless, she regrets some of those moments where, in her view, her tone didn’t better match with “what people were feeling out there.” Such moments were few and far between, she said. “But certainly, though that’s where a lot of my regrets are.”

Handing off the reins

Halfway through Biden’s term, Psaki ceded her post to Karine Jean-Pierre, who still addresses the press on the president’s behalf each day. 

The passing of the baton from one secretary to the next is actually an intricate, storied tradition, Psaki said. “There’s a flak jacket that’s left in the White House press secretary’s office closet; it disappeared at some point,” she said. “I’m not throwing accusations out there, but it was there when I left with Obama, and it was not there when I came in with Biden.”

In any case, once her tenure as press secretary came to a close in 2022, she replaced it with a yellow women’s blazer—sized large enough that the average man, should one succeed Jean-Pierre, could fit into it, too. 

The tradition—with the old flak jacket, and with the new yellow number—is for an outgoing secretary to leave notes in the pocket for her successors. Psaki is heartened by it. In filling up the pockets for Jean-Pierre, she reached out to all the erstwhile press secretaries, “including the Trump ones, including Bush ones.” She asked them, “because we didn’t have the original jacket anymore, if they wanted to pass along advice. And a lot of them did reply.”

But she doesn’t know what the likes of Kayleigh McEnany or Sean Spicer wrote, because Psaki headed for the door before the last of the notes came in.

As for herself, Psaki passed on to Jean-Pierre the same advice her mother gave her when she took the top job. “It was basically, ‘Keep your feet rooted on the ground and your spine straight, and nothing can waver you and nothing can blow you over.’” 

Meaningful words, Psaki said. “It’s a job where you have not just pressure—I love pressure, because I’m a weird person, I guess,” she interrupted herself with a laugh. “But you have high stakes, because you’re speaking on behalf of the leader of the free world. It is to be grounded in yourself and grounded in your knowledge, and not allow people who are trying to blow you over to do so.”

Words of wisdom—and inanity

Psaki’s mother’s advice is surely sage, unlike some other words of wisdom Psaki’s received over the years. 

The worst career advice is, to her mind, a common refrain given to people about to go on TV: “Answer the question you want to answer.”

“It’s terrible advice, mainly because people watching at home are the ones you’re trying to appeal to,” Psaki explained. “If somebody asks you about the state of our democracy and you start talking about roads and bridges, people are confused at home. So that’s bad advice.”

The best advice she’s ever received, on the other hand, has come in the form of skepticism. “I’ve many times been told that whatever I want to do is not possible, and nothing makes me want to do the thing more than someone telling me it’s not possible,” she said with a smile.

But the tidbit she doles out most often is to seek feedback. “Especially when I was younger in my career, and I think for a lot of women, you’re afraid you’re going to be found out as not up to the job in some capacity,” Psaki said. “And the truth is, feedback is a form of showing strength.”

It also—if it’s good feedback—usually makes you better at your job. “You don’t have to take in all the feedback, but it’s something that I wish I had done earlier,” she said. “I think that was a real game changer for me.”