Behind the scenes, however, the woman hired to fix Trump’s image with women adjusts her message, nudging the Republican presidential nominee to stop insulting his critics’ looks and display more compassion.
National polls persistently reveal a dearth of support for Trump among half the nation’s voters. All year long, at least 65 percent of women surveyed in The Washington Post-ABC polls have reported holding an “unfavorable” view of the Republican candidate. The most recent share, released last week, stands at 69 percent, compared to 59 percent of men. No candidate has won the presidency — or even come close — with so little support from women since before 1980.
Female supporters also seem scarce on the ground. At the Republican National Convention this week, the “Women Vote Trump” event appeared nearly empty, according to photos reporters shared on Twitter. “The crowd is so small,” one attendee tweeted, “the panel are asking themselves most of the questions.”
On a recent afternoon, spooning chilled pea soup at a French restaurant near Times Square, Conway, 49, hints how she’ll tackle this challenge. You can’t just tell Trump what to do, she said. You have to give him options.
She illustrates the point with a story about her 11-year-old daughter.
When Claudia emerged from her room on Memorial Day sporting turquoise, Conway asked her to change into blue. “She goes, ‘Turquoise is blue.’ And it is. But it wasn’t a shade available to Betsy Ross when she stayed up through the night sewing the damn flag.”
She chose not to argue with the preteen, which would have delayed their morning. Instead she laid out four Betsy Ross blue choices on her bed. “Minutes later,” she says, “she came out in one of those shades.”
Conway follows the same approach with the Republican presidential nominee. Never command. That could insult him. Always make suggestions, backed with information in 10-second sound bites: Betsy Ross lacked turquoise. Female voters want compassion.
Acting tough comes naturally to Trump. Compassion ... well, she says, he has it. They’re working on showing it off. She withholds the details.
Evidence of her influence appears in Trump’s response to recent tragedies. After the deaths this month of Alton Sterling and Philando Castile — two black men fatally shot by police — and the killings days later of five Dallas officers, he released a statement that even opponents praised.
“This is a time, perhaps more than ever,” Trump said, “for strong leadership, love and compassion.”
'Maybe it's just the mother in me'
Though women have voted more Democratic than men since 1980, Trump’s elusive female approval concerns his team. Mitt Romney’s support from women in the Post/ABC polls during his 2012 campaign never dipped below 53 percent, though he ultimately received 44 percent of women's votes.
On the eve of the 2008 convention, meanwhile, 55 percent of women said they had a favorable impression of John McCain, while 31 percent report similar faith today in Trump. Not that Clinton is enjoying glittering success among women: The same poll found 48 percent like her, while another 48 percent say otherwise.
National polls broadcast a tight race, with Clinton holding a five-point lead over Trump, a slight loss of edge since June. The business mogul’s deficit with women, however, has stayed consistently larger than his opponent’s deficit with men.
That could have something to do with his public treatment of women.
Trump has called comedian Rosie O’Donnell “disgusting” with a “fat pig face” and Arianna Huffington “ugly inside and out.” He asserted supermodel Heidi Klum is “no longer a 10.” He said Fox News anchor Megyn Kelly had “blood coming out of her wherever.” He threatened to “spill the beans” on former rival Ted Cruz’s wife, Heidi, while retweeting an unflattering picture of her. Last week, he attacked the sanity of Ruth Bader Ginsburg, widely hailed as a feminist icon, claiming her “mind is shot.”
Conway doesn’t like the name-calling. “Maybe,” she said, “it’s just the mother in me.”
But that’s not the side of Trump she wants to talk about.
She smiles broadly. She leans in close. Her blond hair falls over her red Karen Millen sheath dress. She wants to shift attention away from Trump’s takedowns to his ideas.
What women really want
The former Washington lawyer, who lives in New Jersey with her husband and four children, built much of her nearly three-decade career around a persistently difficult task. She aims to help conservative men snare the female vote, a feat no Republican presidential candidate has achieved since George H.W. Bush first sought the White House in 1988.
Conway grew up in Atco, N.J., 43 miles northeast of Atlantic City. Her mother, grandmother and aunts raised her. The half-Irish, half-Italian women posted prints of the pope and the Last Supper on the walls. They prayed before meals. They celebrated faith and grinding work.
She found her professional niche in 1988, working for Dick Wirthlin, Ronald Reagan’s pollster, in the summer before she graduated from George Washington University Law School. Her first assignment was to demystify the gender voting gap: How could the GOP attract more women?
In 1995, Conway founded The Polling Company/WomanTrend, a consulting firm that specializes in market research. A decade later, she co-authored a book called “What Women Really Want."
Like Trump, she has generated criticism over the years. She caught flack for telling women to embrace femininity, not feminism, in a 2011 speech at the Conservative Women’s Network. She caught more in 2013 for advising a group of House Republicans to stop talking about rape. (Her former client, 2012 Missouri Senate candidate Todd Akin, famously said women can’t get pregnant during a sexual assault because their bodies “shut the whole thing down.”)
And sometimes, spontaneously, she goes off message. Before a recent NBC appearance, a hair stylist brushed her blond locks and talked about a certain someone going bald. “That’s okay!” Conway said. “Women in my focus groups, they say a bald man is trustworthy. He has nothing to hide.”
Conway met Trump in 2006, when she served on the condominium board at Trump World Tower in Manhattan. She said Trump seemed surprisingly hands-on, showing up at meetings to hear the residents’ concerns. She thought then he was much kinder than his public persona suggested.
He called her over the years, following a familiar prompt: I saw you on Hannity. I saw you on CNN. What do you think of this?
In March 2015, Conway said, they met to discuss his presidential bid. She declined to work for him, thinking: I’m not sure if this guy would ever care about polling. She worried about how the public would perceive their partnership. “Like, ‘What are you doing there?’” she said. “Riding on a plane? Whispering in his ear about what he should say to women?”
She linked up instead with Sen. Ted Cruz and ran his super PAC, Keep the Promise. When Cruz's campaign collapsed, Trump called again. Conway realized he was a serious contender.
His history of bullying women wasn’t a dealbreaker. Trump’s string of biting comments shouldn’t hurt him more than it already has, she said.
“The more that people keep repeating the same insults, the more it invites him to very legitimately defend himself,” Conway said. “Women look at the full measure of the man, not just one comment.”
A tough job
Conway likes a challenge. Her past clients include Newt Gingrich, Cruz and Trump’s pick for vice president, Indiana Gov. Mike Pence, who lost women by five points in his 2012 race. None have been popular with the demographic.
“With all due respect, Kellyanne is very good at understanding Republican women. But working with candidates like that and trying to not make them look like cave men — that’s a tough job,” said Katie Packer, a Republican strategist who worked on the Romney campaign. “She has created a niche where candidates can check a box and say, well, they've got a woman advising them.”
“There’s a deeper problem that goes beyond any single individual in Republican politics,” added Sabrina Schaeffer, executive director of the Independent Women's Forum, a conservative think tank in Washington. (Conway sits on the board.) “Republicans for many years simply didn’t take gender differences seriously. ‘We can ignore certain issues, and that’s fine.’ But it’s been politically tremendously damaging.”
The polls support her point. Women have voted majority-Democratic in every presidential election since 1992.
What makes Trump fare worse with women than, say, Romney ever did likely has little to do with policy, though. A man in power flinging gendered insults appears to register as more disturbing to female voters.
In the Post-ABC poll, 56 percent of respondents said Trump is biased against women and minorities, while 39 percent said he was not. Women, though, were 10 points more likely to report this belief than men. They were also 21 points more likely to say they felt “strongly” the candidate is biased.
Sarah Lenti, a Republican strategist and former aide to Condoleezza Rice, said Trump needs to act like a statesman to improve his numbers with women. “He’s like a wild animal,” she said. “He can’t control himself.”
Not that his behavior stopped him from drawing roughly 14 million voters. The kind of voters he still needs to win — moderate conservative and independent women — tell Lenti he would be more appealing with one tweak.
“The fix,” she said, “is as simple as Trump starting to control himself.”
Trump joked about his woman problem in May at a speech before the National Rifle Association. "I will say, my poll numbers with men are through the roof,” he said, “but I like women more than men. Come on, women. Let's go."
Enter Conway, whom Trump declared “an expert on female consumers and female voters” in a July 1 hiring announcement. She’s among the highest-ranking women on his team, serving as both senior adviser and pollster.
She conducts aggressive polling. She stays on the topics conservative women say they most care about, highlighting Trump’s resolve to lift middle-class workers and tighten the border.
On family issues and policies that disproportionately affect women, she frequently takes the traditional route. While Clinton has argued that paid maternity and paternity leave should be universal, Conway said Trump will likely leave that work up to the states. On reproductive issues, Conway considers Pence, who wants to outlaw abortion, an asset to the ticket. Trump has flipped positions on abortion at least four times, calling earlier this year for women who undergo the procedure to be punished. He later retracted the statement.
There is at least one family policy she hopes will uniquely appeal to women, wading into an area typically owned by the left.
Ivanka Trump, his oldest daughter, is leading the charge on a child-care plan, Conway said. She’s meeting with academics on both sides of the ideological aisle. It will offer a conservative alternative to Hillary Clinton’s proposal, which caps the expense at 10 percent of a household’s income and funds the much of the cost with tax credits and subsidies.
She won’t disclose many details but said Trump will promote incentives for businesses — perhaps in the form of tax credits — to help take care of their employees’ child-care needs, which, she points out, could boost their bottom lines. Trump’s tax plan, meanwhile, will include a $500 per family credit to help cover child-care costs.
Gender, Conway says, doesn’t determine what voters care about. Her research shows it does, however, play a role in how they cast their vote.
“We need to address women,” Conway said, “from the waist up.”
That means, to her, doubling down on conservative messaging and delivering it with a less disparaging tone.
She often hears the same feedback from female voters about Trump, regardless of their background.
“They say, ‘I don’t always like what he says, or how he says it,'” Conway said. “‘But I think he would change Washington. I think he would create jobs and balance budgets.’"
“I can work with the ‘but.’”
Scott Clement contributed to this report.