How I Managed A Male Staff Twice My Age As A Woman In My 20s

How these five women overcame microaggressions and established themselves as successful leaders.

How I Managed A Male Staff Twice My Age As A Woman In My 20s
[Photo: Flickr user Bernd Zube]

Judy Garvey was only 26 years old when she was promoted to chief operating officer of a drone startup. In her new role, the engineering team she oversaw consisted of six older men (some of whom had children Garvey’s age), and it grew to two more, as well as some additional contractors. “To earn respect from the teams,” she says, “I found I was always working to build their trust in me.”  


Garvey credits the startup’s culture for the opportunity to take on such a senior role so early in her career, as opposed to what might have taken years in a more traditional, established organization. That said, Garvey also notes that since she started in a more junior role and was promoted to a leadership role as COO, everyone had a chance to witness her grow as a team member. “I think [they] realized that I had earned the right to the senior role,” Garvey says. “Even though I wasn’t a technical leader on the team, I was a business leader, and they respected that I had worked hard to earn the promotion.”

Although she admits there were challenges, “We were able to build connections and they treated me with respect–as a person and as a leader,” Garvey says. Unfortunately, things were about to get worse.

The drone startup acquired another established company that had been in business for 18 years. That brought an additional five men to the engineering team. “I have never experienced such resistance when trying to get acquainted with a team’s processes and operations,” Garvey recalls. “I was actually asked to not be in weekly engineering meetings because I asked too many questions.”

Garvey tried to build connections with the new members of the team. Eventually though, despite her best efforts getting no traction, she says she stopped trying so hard and got another person to lead the team who reported to her. “To be honest, they didn’t really respect him either, which is probably just indicative of their lack of respect for the acquiring leadership team in general–not specifically just for me.”

Garvey says she resigned after a year for a number of reasons. One reason “was definitely the disrespect I felt on a daily basis from the older men I was managing.” At 28, Garvey is now working for a software development company. “I’m not currently managing any older men,” she adds, “which is kind of a nice change.”


 Microaggressions like those Garvey faced that undermined her leadership are a factor in fostering negative work environments that often lead people to look for a new job. 

Fielding Insults and Slights

Jenna Oltersdorf learned how to deal with such microaggressions early on as the founder of Snackbox, a PR and design firm. Oltersdorf was only 29 when she started the company, but she says, “I knew my stuff,” and “I’m a little sassy when it comes to female equality.”

Even so, Oltersdorf felt she needed to work even harder to prove her experience and creativity, and had three older men reporting to her. She recalls one time in particular when she was delivering a pitch to a prospective client. “He referred to me as girl, honey, and sweetie,” she recalls, but was not using similar language with the men in the room. When she “politely asked him to refer to me as a woman, as I was his counterpart in this particular meeting,” she remembers him being visibly surprised by her request. “I assured him that I would wow him in the meeting with my team’s creativity, experience, and expertise,” she adds.

Looking back, Oltersdorf says she realized he was being kind. “But in my mind, he was treating me like his granddaughter, not a potential business partner,” she observes.

“I think it’s important that women of all ages politely correct how we’re referred to and treated in a business setting. We need to set the tone and educate those who may not realize they’re treating us differently from our male peers,” she asserts.


Why You Need Allies

Although women make up 47% of the workforce, according to the Department of Labor, the most recent report by and McKinsey based on data from 132 companies that employ more than 4.6 million people found that women account for only 20% of staff at the senior vice president level and 20% of line roles that lead to the C-suite. That’s partly due to lack of support and sponsorship from the men in the workplace, according to recent research in Harvard Business Review

For Garvey, that person was her CEO. “I always reminded myself that I would not be in this leadership position if my CEO didn’t think that I could do it,” she says. “His trust and confidence in me helped me see that I could lead these teams, and I could lead them well.”

Megan Bos was 23 when she learned the importance of having a male ally. Bos was brought in as a strategy consultant for a project for a major retailer to help close out the final phase of work. “I was the only female on the project except for the managing partner, who was only in the office every few weeks,” she explains, “and I was younger than every member of my team by at least seven years.”

Bos points out that she had a good relationship with the managing partner who knew she could execute. “When I first started, I was not totally convinced I was qualified to tie the bow on such a big project just because of the scope of work,” Bos confesses. But she also says she initially had trouble convincing the team she was qualified to lead because of gender, age, and cultural differences. “I knew that getting an older group of men to see me as someone who held authority, and also was capable, would be a challenge,” she says.

Advice from her female mentors was to make herself the expert in the room. “If I had a well-documented plan and could walk into any conversation and answer the questions that they had, speak confidently in meetings, and deliver a well-thought-out delivery plan, they would see me as a capable individual and trust that I was the right person for the job,” she explains.


“I also found that finding an ally on the team was helpful,” Bos says. Having a team member who didn’t have a problem with the gender and age difference helped to tip the scale when she needed someone to back her up in a meeting. “There were a few circumstances where comments were made about my age,” says Bos. “However, over the course of the [project], the comments changed to be around how impressed they were with the work I was delivering.”

Acknowledge What You Don’t Know

“Don’t spend all your energy trying to prove yourself,” Heidi Pozzo, founder of Pozzo Consulting, advises. Instead, she says, “Your job as a leader is to bring the best out in people.” She says time is better spent trying to understand the team’s interests and strengths. “Then give them the opportunity to excel and get public recognition for it.”

When she was leading a project team in her late 20s and had a dozen older men reporting to her, Pozzo says she asserted right away that they were the experts from their respective part of the business. “I did not try to act as if I knew more,” she says. “Rather, I respected their knowledge and told them, and worked to get the team to common ground to complete the project.” Pozzo says everyone had fun working together, and they eventually got recognition for their role in making a product that is still in use today–15 years later.

Finding Common Ground

“I’ve found that making connections with my team really goes a long way in winning people over,” says Garvey. “I earned their respect by consistently doing what I said I would do, executing on lots of little wins in my daily work, and being open about where my strengths and weaknesses were in the business,” she explains.

Penny Queller is now senior vice president for the Americas at Alexander Mann Solutions, a global recruiting firm, but was a manager at a golf course through college, where all of her reports were male retirees, some in their early 80s. Queller says, “Being your authentic self is a better way to motivate people.” She says she’s not afraid to show her sense of humor or let the team know she might be having a crappy day. “I have the same problems you have,” she explains. “People love it when you show you are not made of steel,” says Queller. But don’t cross the line, she cautions. “You are not going out with these folks, socializing, or going to a club.”


Be Confident

But confidence is key, according to Bos. Having confidence in her ability to lead helped others see it as well. “The best way that I get that is from informing myself thoroughly on the situation and the means necessary to tackle the task,” she says. “That way, I’m always prepared to deliver the right answer, guidance, or mitigate an issue that arises.”

Adds Garvey: “Having an ally on your side that can help encourage you when you’re feeling discouraged is valuable to help maintain your confidence.”

About the author

Lydia Dishman is a reporter writing about the intersection of tech, leadership, and innovation. She is a regular contributor to Fast Company and has written for CBS Moneywatch, Fortune, The Guardian, Popular Science, and the New York Times, among others.