Women for Romney: An Interview with Romney Insider Cindy Gillespie


"I had no idea," is what Cindy Gillespie hears from women when they find out about Mitt Romney's extraordinary record on hiring women in senior positions. Gillespie is a former Mitt Romney senior staff and advisor for the 2002 Winter Olympics in Salt Lake City and in his Massachusetts Governor's office. With a dozen of her former colleagues from Massachusetts and the Winter Olympics, Gillespie is traveling around the country meeting women and talking to them about the Mitt Romney they knew as a boss and friend. 

Recently I had an opportunity to meet with Gillespie and hear firsthand about her work and impression of Mitt Romney. Like many others, my "I had no idea" moment came after reading Gillespie's blog, and she graciously agreed to meet me and talk about "the real Mitt Romney." What I read in Gillespie's blog post, and subsequently in the posts written by her colleagues, told a different story about the man that has been accused of waging a "War on Women." It is quite a tale!

While they were together for dinner at the GOP Convention in Tampa, Gillespie and her colleagues decided to write the blog post and take to the road to talk to other women. A younger woman overheard them telling stories about their old boss and said, "listening to all of you is so exciting to me. I didn't realize all he has done for women." Gillespie puts it this way: "We decided it was time to go out and tell 'em ." 

"It's so interesting how a fake image of him materialized," she said. "I had never really thought about what you have to go out and tell people," she admitted, still surprised that the Obama campaign had so successfully "put fear in women that Romney might be the kind of person to surround himself only with men."

Starting with the Salt Lake City Olympics, Gillespie and her colleagues saw a leader who pushed staff to take on new challenges and hired women in positions formerly held by men.  Rather than the traditional senior positions that women tend to end up in, like human resources and public relations, Mitt Romney sought "the best person for each job." He put four women in very senior positions, including two that had not been held by women in past Olympics:  Telecommunications and Sport. Additionally, of his five direct reports, two were women — one of them Gillespie herself. 

"One of the things that was wonderful about working with him, male or female, is that he was always pushing you to go to the next level in your own capabilities and take on new challenges. It is an interesting way he does it. He believes you can do it, and therefore you go figure out how to do it." 

Professional growth for Gillespie, was "amazing." She talks about her expanded position, from Government Relations to "Government Relations AND Torch" at the Winter Olympics. Torch, that ancient, traditional illuminated stick, involves some 15,000 runners, big logistics, every state, international participants, major supplies for uniforms and extra torches, and raising some $25 million. When Romney approached Gillespie with the request to take on the extra responsibility, she says she responded with trepidation. "You understand I've never done anything like that before. So why did you give this to me?" Romney's response was "typical," she said. "Because I thought you might be getting bored and you needed a challenge." Despite its proximity to 9/11, the Torch activities leading up to the Winter Olympics were successful. Romney even insisted she involve her Dad, a Vietnam veteran, as a torch bearer in the Washington, D.C. ceremony. 

Romney brings women into senior management

In Massachusetts, half of Governor Romney's cabinet was made up of women. He was recognized "every year he was governor" for having more women in his cabinet and senior positions than any other governor. He selected and campaigned for Kerry Healey, his Lt. Governor. His Chief of Staff, Beth Meyers, was a key advisor and counsel in the governor's office —she later managed his 2008 campaign and serves as a senior strategist now.

Engaging women as leaders on his team is something Romney does, "quite naturally," Gillespie added. "Usually when you go into corporations and you see when they are trying to make sure they have gender diversity that there are certain positions that you will find women more likely to serve in." Not so in Mitt Romney's management teams. "That is one of the more interesting aspects of his leadership recruitment. It's not just that he had women in senior positions but it is the positions he had women in because they were not the traditional ones." Instead, he sought to bring the most qualified people to key positions. 

Gillespie also stressed that Mitt Romney knows how to find the best people for the jobs.  By definition, many of them are women.  His work style, his pro-family beliefs, and his personal commitment and drive make for an attractive working environment.  Family plays an important part in Romney's life, and he respects not only the challenges his employees take on at work, but what they are doing at home.  Because that is how he lives his life, it is very natural to him to look for that kind of person in his employees.  "When you do that, you end up with a lot of women in your top positions," she said.

He has a unique, focused work style

"He is very very focused. When he has a problem to solve, he is going to solve it. What we need right now is someone who is 100% focused on getting the economy on track and getting jobs.  That's Mitt Romney."

When Mitt Romney first arrived in Salt Lake City, the games "were really in a mess," and there were serious financial, operational and morale issues for him to contend with at work. "It was pretty clear that Mitt didn't realize how bad it was," Gillespie said. But "Mitt never ever drops the ball." In spite of the challenges, "his big thing with us was that we had to turn morale around."  His laughing and joking took off some of the tremendous pressure and the the Salt Lake City Winter Olympics went from $400 million in debt to creating a $100 million legacy for Utah. 

"Mitt wants a lot of robust debate." Being on his senior team means taking part in debate discussion and understanding the "different elements." 

He is thorough. When he is making a big decision, "he really digs in deep. He wants very informed, creative debate." Gillespie explained that "a large part" of her role was to play devil's advocate to help him consider "all the various options" so he could make a decision. Timidity is not a trait he values among his senior team. "You cannot be a ‘yes person’ with Mitt. There is no reason for a yes person to be in the room with Mitt." 

Why is getting this message out so important to Cindy Gillespie? 

First, because Gillespie cares about women and how we will fare in the next four years. She is convinced, based on more than eight years of working closely with him, that Mitt Romney can lead the country down the right path. Secondly, she wants women to understand that they have in Mitt Romney a leader who can not only lead, but who, in the process of bringing in the best advisors, will naturally include women, not just because he has done it before, but because "that is who he is."

On the road, Gillespie and the other "Women for Mitt" talk to women, mostly in their 30's, 40's and 50's. What they ask most often is, "What is Mitt like as a person?" And, referring to the economy and jobs issues, "Can he fix it?" The women they see have "real-life day-to-day problems. They want to balance their checkbooks, put food on the table, and keep their 8 million small businesses operating." Gillespie says, "We've seen him do it.  He can fix it." 

While Gillespie and I never talked about Governor Romney's "binders full of women" comment during this week's debate, Kerry Healey, former Lt. Governor of Massachusetts, in an interview this week, addressed it. Her job was to recruit for the governor's administration and she indicated she "spent many hours" looking through resumes to recommend strong candidates for key positions in his administration. His "binders" helped identify and install a record number of women in top positions, including 50% of his cabinet. The point – whether it was binders, or files on a computer (today he would look at them on an iPad, most likely) – is that women were not only considered but sought after and hired. 

I can only conclude, from this opportunity to hear about the "real" Mitt, that more women need to hear from the Women for Mitt, and understand just how much he is working for them, and has worked for them throughout his career. 

Gillespie and the Women for Mitt will be traveling in Iowa and Nebraska on October 18 and 19 including Omaha, Council Bluffs, Omaha, Indianola, Iowa City, Davenport and Waukee. Follow their blog, Women Working With Mitt, and read more about their adventures and their old boss, Mitt.