pink staircase

How to Get Past the Messy Middle to the Top

Today, women are more likely to have a college degree than men. Women now account for slightly more than half of the workforce, according to statistics from the U.S. Department of Labor. And nearly half of working women are the primary breadwinners of the family.

Yet getting past middle management into positions of leadership remains a major challenge for women today. This may be partly because the “messy middle” is a period in which women may be gaining more responsibilities at home at the same time that they are gaining more responsibilities at work. And women continue to shoulder the majority of the caregiving duties.

Leaders in the Equality Lounge® @ OOH Media Conference share advice on how to rise the ranks past the messy middle­­–– and how to rewrite the rules once arriving at the top. Keep reading for key takeaways and tune in here for the full discussion.


Know Your Worth

As human beings, we all possess unique talents and perspectives that, when pulled together, have the power to accelerate change. But, in order to ignite the power of that diversity, we first need to recognize the potential that we each hold as individuals. Leadership norms are changing. Qualities once considered “feminine” are more valuable than ever in the modern workplace and the future of the world at large. Among them: empathy, intuition, communication, relationship-building, philanthropy, and the ability to multitask.

Carly Zipp, Senior Director, Communications, Sponsorships, and Events, OUTFRONT Media, thinks that women should also own their various life experiences. “Being pregnant has opened up a lot of doors for me. It’s connected me to other women, it’s also given me the opportunity to find out just how amazing I am at multitasking,” shared Carly. “Women can bring attributes like that to the workplace.” Companies can help everyone perform at their best by offering generous and flexible policies (e.g., mandatory paid parental leave for men and women) that make people feel supported.


The Opportunity to Fail is a Gift

While boys are taught to be brave, girls are taught to be perfect. This quest for perfection and the fear of failure can hold women back from ever trying in the first place. Try to remind yourself that working hard and delivering results (aka playing it “safe”) doesn’t always necessarily lead to success. In this rapidly changing world, failure is inevitable and it happens to everyone. So let’s not just get comfortable with failure. Let’s seek it out so that we can improve.

“You have to stay visible,” says Rainbow Kirby, Director, Corporate Communications and Marketing, Clear Channel Outdoor. “When I first started my career, I just had my head down trying to get things done. The people who I saw racing past were the ones who created a walk-about and who took the time to check in with senior leadership and help what they were doing.”


Managing Up: Leadership Lessons Come from Everywhere

No one is going to hand someone else a position of leadership in today’s competitive workforce. Getting ahead means “managing up:” Enter a relationship offering value, be proactive about assignments, and get to know your managers.

Gale Bonnell, Director of Business Development, Adams Outdoor Advertising, shares, “I don’t think your title has a lot to do with initiative. Regardless of where you are in an organization, if you want to be a leader, you do it by your actions, by seeing what needs to be done and stepping up.” In other words, leadership is a choice that everyone has the ability to make. It’s also all of our shared responsibility to proactively make that choice if we want to initiate courageous conversations that increase awareness, education, and ultimately accelerate progress towards gender equality.


Managing Down: The Ripple Effect

Traditional leadership training often skips over “managing down,” which is all about managers being open to receiving feedback from the teams they lead. Leaders can encourage their teams to share feedback by creating safer spaces and improve their managerial skills in the process. “We need to make sure we’re providing people with the opportunity to prove themselves, share their thoughts and opinions and start this cycle. If you give them the opportunity, when they get to a higher position, they’ll give their people the opportunity. It’s a cycle you need to continue,” says Nicole Randall, Senior Director, Communications, Outdoor Advertising Association of America.


Engage Men

New research by LeanIn.Org and Survey Monkey reveals that the number of male managers who say they are, “uncomfortable participating in common job-related activities with women,” has jumped from 46% to 60% in the past year. We need to figure out how to work together to reverse this trend since leadership is still predominantly male and feedback from leadership is necessary in order for anyone to get ahead.

One way to reverse the trend is to simply tell someone if they are making you feel uncomfortable, because they simply may not be aware. And men can ask colleagues if they are comfortable, whether it is about having a working dinner or telling a woman that he likes her outfit. “If you’re unsure, just ask them,” says Nicole. “If someone’s making you uncomfortable, just tell them and make them aware of the fact.”


Managing Around: Build Relationships with Everyone

We talk about the Golden Rule, “Do unto others as you would have them do unto you.” But what if we took it to the next level and started living by the Platinum Rule, “Do unto others as they’d like done unto them?” Shelley Zalis, CEO, The Female Quotient, says, “What might be okay to me, might not be okay for someone else. We’re living in a world of personalization, customization, and coming back to media, we’re not ‘one-stop shopping’ or ‘one-size-fits-all’ anymore. We have to be sensitive to humans, to what they want and feel.”

How can we transform workplace culture and better enable women to succeed? It takes courageous and sometimes uncomfortable conversations to build empathy and conscious leadership. It may be uncomfortable right now because we’re discussing subjects that haven’t been talked about before in the workplace. But equality is not a female issue. It’s a social and economic imperative. It means equal pay for equal work, paid parental leave, and a more equitable shouldering of caregiving responsibilities. When we accommodate the different life stages of all employees, rather than penalize them, it makes us all stronger.


For more on the benefits of achieving full gender equality, check out:

How to Hire with an Equality Mindset
Shelley Zalis on Men and Women in the Messy Middle
Return on Equality: How Gender-equal Ads Pay Off