Hillary Clinton’s fall to-do list

Hillary Clinton is set to hobnob with world leaders and the biggest names in business, politics, academia and philanthropy – not to mention celebrities – at the Clinton Global Initiative in New York City, fresh off her re-entry into the political fray at the Iowa Steak Fry.

The two settings couldn’t be more different: one a huge family reunion-style gathering in a field dotted with farm equipment, the other a star-studded roster of events in swanky midtown Manhattan hotel ballrooms where Leonardo DiCaprio, Jordan’s King Abdullah II and Melinda Gates, among (many, many) other prominent people will make appearances. Clinton’s challenge, if she runs for president a second time, will be showing she is just as comfortable with Iowa’s steak fry crowd as with New York and Washington’s elite.

As she spends this fall campaigning for vulnerable Democrats trying desperately to maintain control of the Senate, Clinton needs to show she understands the problems of everyday Americans, even though she rubs shoulders with world leaders and the uber rich.

She will flex political muscles that have atrophied since her 2008 presidential run and try to avoid making errors like those that punctuated her reintroduction to public life this summe: a book tour bookended by gaffes – including her remark that she and her husband were “dead broke” – and her phone call to President Obama in which she apologized for disparaging his foreign policy in an interview with The Atlantic.

Here’s what Hillary Clinton needs to do this fall as she re-enters the campaign sphere:

1) Connect with ordinary voters

Clinton’s big book tour blunder was saying that she and her husband, former President Bill Clinton, were “dead broke” when they left the White House. The former secretary of state followed that assertion by saying that they are not “truly well off,” despite having earned more than $100 million as a couple since 2000.

Democrats are practically pleading for Clinton to use her midterm campaign rally appearances – which she has yet to announce – to bring herself back down to earth.

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“She is a Midwesterner really,” said one Democratic strategist supportive of a Clinton run, who was granted anonymity to speak freely, “and she has been spending a lot of time in very rarefied air.”

She tried to start reaching out at the Harkin Steak Fry by addressing voters’ economic anxieties. “If you work hard and play by the rules, you deserve the possibility of a good life for you and your family,” Clinton told the jeans and T-shirt crowd as they ate red meat with plastic forks.

Supporters of Clinton insist the notion that she is out of touch won’t hold. But that won’t stop her critics from trying to make it stick.

Clinton observers say they are concerned she will react to her unforced errors of the book tour by being too scripted, maintaining a controlled environment that ultimately stifles her authentic moments and makes her appear aloof.

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“All good politicians in the Internet Age maintain a controlled environment. In Secretary Clinton’s case, one of the reasons her off-script moments have so much power is because people have gotten so used to seeing her through that controlled prism,” says Phil Singer, who served as a spokesman on Clinton’s ’08 campaign.

He cited her testimony before Congress on Benghazi – when she countered Republican questions about what prompted the attack on the U.S. mission in Libya by exclaiming “What difference at this point does it make?” – as an example of Clinton effectively standing her ground. And he said her improvised quips when a shoe was thrown at her during a speaking engagement in April highlighted her sense of humor and made her seem quick on her feet.

2) Rally the base, especially women

Hillary Clinton needs to tune up her appeal to key parts of the Democratic base: African-Americans, Latinos, younger voters and, in particular, women.

On Wednesday, the final day of CGI, Hillary Clinton and Melinda Gates will appear before a crowd of thousands to discuss progress around the world for girls’ and women’s equality, an issue Clinton first took to the international stage in 1995 at the United Nation’s Women’s Conference in Beijing.

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Clinton has begun embracing her gender – something she put on the back burner in 2008 – as she specifically addresses women’s economic concerns.

“We see it in the motherhood penalty, with many women forced to take a pay cut when they have children while men often get a pay bump,” she said. “So let’s be clear; these aren’t just women’s issues, they’re family issues, they are American issues and they hold back our entire economy.”

In Iowa, some of Clinton’s most well-received comments were about equal pay and women’s reproductive health.

Her base is eager for more.

“I think she’s really qualified. Plus I’d kind of like to see a woman in the White House!” Linda Church of Ames, Iowa, told CNN, a constant refrain among women at the Harkin Steak Fry.

Clinton is expected to take that appeal on the campaign trail, where many of the candidates she may stump for are women – Sen. Kay Hagan in North Carolina, Sen. Jeanne Shaheen in New Hampshire or perhaps Staci Appel, who is running for a seat in the House in Iowa and has a real shot at becoming the first woman Iowans elect to a federal office.

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She could help Democrats in states where women’s issues are playing big, like Colorado, where the hot-button issue of reproductive health has become a major campaign topic in the race between Democratic Sen. Mark Udall and his

Republican challenger, Rep. Cory Gardner. Or Clinton could campaign for men running against women, like Bruce Braley, who is facing off against Republican candidate Joni Ernst in Iowa’s Senate race.

3) Kiss and make up with Iowa

When I asked Hillary Clinton in Iowa if she is going to return to the Hawkeye State to campaign for candidates, her answer didn’t inspire confidence that she would.

“Well, we’re gonna do what we can,” she replied.

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Clinton’s visit to the Harkin Steak Fry, her first political event in almost six years, was a return to the scene of great disappointment, where in 2008 her campaign sorely underestimated the wave of new caucus-goers that then-Sen. Barack Obama would turn out in the first-in-the-nation contest, and she finished in third place, behind John Edwards as well.

“Iowa was tough. It was where the wheels came off the wagon. I don’t think anybody has ever forgotten that,” said one Clinton ’08 alum, “but I do also think that those who want her to run again understand how important it is for her symbolically as well as politically to start off well there.”

Her visit last week was a first step, but Iowans want more.

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“I think she just needs to connect with everybody more than she did before, especially Iowans,” said Joni Williams of West Des Moines, an ’08 Obama supporter who is now backing a presumed Clinton run. “I don’t think she really showed up as much as Barack did last time. He was here all the time.”

And that enthusiasm that Obama inspired? It might be impossible to replicate.

“That’ll never happen again. That was a one-time event with Barack Obama,” said Jim Mikulanec of Indianola, Iowa. “I think we’re going to have a great campaign with Hillary if she runs, but you can’t put that back in the bottle. She’ll have to reconfigure.”

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One Iowa politico, who was also granted anonymity to speak freely, said Clinton will find an enormous amount of support but noted there is still a significant minority of Democratic caucus-goers who are skeptical of her.

“They are not impressed with her since she left the State Department. Her (book tour) gaffes are reminiscent of how she approached the (’08) campaign. It doesn’t mean they won’t support her, but their enthusiasm depends on how she relates to Iowans. She needs to press the flesh to get over that, she needs to show she is listening to voters, sharing her views, not telling her views.”

Another visit to Iowa before the midterms would go a long way.

4) Repay favors to friends

While Clinton’s midterm campaign stops are still not public, those close to her say she will campaign where her popularity will best help candidates.

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Her appearances will be limited: We may not see her on the stump until home stretch poll numbers in tight races determine where Clinton is most useful as a surrogate or until the beginning of early voting periods, which attract more Democratic than Republican voters.

This is also a time for Clinton to help those pals who have supported her over the years, and all the better if they happen to be in a state that’s advantageous to her presidential aspirations.

Sen. Jeanne Shaheen seems like a natural recipient of a visit from Hillary Clinton. New Hampshire holds the first-in-the-nation primary election, and Clinton’s ’08 win there breathed new life into her candidacy after her Iowa loss.

The Clintons also owe the Shaheens a debt. Shaheen’s husband, Bill, fell on his sword in 2007, resigning as co-chair of Clinton’s New Hampshire operation after suggesting that Obama’s disclosure of cocaine use in his younger years would hinder his candidacy. Former President Bill Clinton has already hosted a high-dollar fundraiser for the New Hampshire incumbent.

“The premise (would be) she is just there to help a longtime friend,” one Democratic strategist said of the possible campaign appearance.

Friends or not, Hillary Clinton will be judged by whether the candidates she endorses win or lose.

That’s why Bill Clinton will be doing much of the heavy lifting. He’s expected to squeeze every minute out of the next couple months campaigning alongside Democrats. His wife, sources say, will choose more carefully, appearing with far fewer candidates.

“Remaining less political is in her interest,” said Ron Brownstein, editorial director at Atlantic Media, pointing to recent poll numbers that show Clinton’s approval rating dipping as she has re-entered public life. “But the people she owes favors to and she wants favors from are all going to expect her help.”

5) Get to yes … or get out of the way

Clinton ruled out a second presidential run as recently as late last year. How things have changed.

In July, after “Daily Show” host Jon Stewart asked her if she liked an office with or without corners, she joked, “You know, I think that the world is so complicated, the fewer corners that you can have, the better.”

Now she says she will make her decision after the new year and teased the crowd in Iowa, saying, “It’s true. I am thinking about it.”

So what is she struggling with? It seems to be finding a way to articulate a case to voters about why they should put her back in the White House.

“We’ve reached a point in our life when we think you really shouldn’t run for office if you don’t have a clear idea of what you can do and a unique contribution you can make and you can outline that,” Bill Clinton said this summer.

And then there’s the question of what a Hillary Clinton team would look like. Her ’08 campaign was notorious for infighting and strategic disputes. Many observers say she greatly needs to refresh her team with new talent, a difficult task for a woman who values loyalty, sometimes above skill, sources say.

“She’s got a very small group that is advising her and they’re clumsy,” said one Democratic strategist who wants to see her widen her circle beyond the group of stalwarts who were with her at the State Department – many of whom date back to her time in the White House as first lady.

“She has to sort through that universe and another universe of people who are qualified but haven’t worked for her in the past and create a team … that’s cohesive and that’s functional,” said Jay Carney, the former Obama White House press secretary and now a CNN contributor. “It’s not an easy task.”

If Clinton waits too long to make up her mind, there’s a serious risk to the party: Right now she is effectively blocking other Democrats from getting in the race, though Maryland Gov. Martin O’Malley and Vermont Sen. Bernie Sanders, an Independent who votes with Democrats, have been making the requisite stops in key states.

“It sows a seed of discontent if she’s holding out, and those (caucus-goers) skeptical of her might solidify for other candidates,” said one Democratic operative in Iowa, who thinks they might seize the opportunity to get in the race if Clinton drags out her decision.

Clinton declared her candidacy in January 2007 for her first shot at the White House, but lamented how early she got in. This time, it’s as if she’s already running.

“If she’s at 43% approval now in 2014, after just doing a quote-unquote book tour, then the public already sees her as a candidate,” said Amy Walter of the Cook Political Report. “It’s just about making it official.”