The Hustle Begins Here

A few months ago, I had the crazy idea to start a podcast about the best jobs, the worst jobs, and the lessons we learned from them. Especially the worst ones.

I was lucky enough to have Samantha Skey as my first guest, and it wasn't too long before we figured out that we grew up in nearby towns, working in the service industry in New Jersey and both moved to NYC in the early 90's to start our careers in publishing.

Hers took off. I chose a different route.

Today, Samantha Skey is a powerhouse. She is Chief Executive Officer of SHE Media, a Top 10 Lifestyle Media company that reaches 74 million monthly unique visitors. Samantha didn’t start at the top, though, and throughout her 25 year career in digital media and technology, she shared with me so many amazing insights and experiences that she had, working with both entrepreneurial startups and behemoth brands.

During this episode, she happened to say something about coming up through the ranks in a male-dominated industry that hit me right between the eyes:

“Most of my career has been spent surrounded by powerful men. And that has certainly influenced the way I speak and the way I act. But what does that mean? And is it a good thing?

It's a really good question—and one I've thought about many times—but never had articulated in quite that way. My first business partner was an older gentleman, and I saw how people spoke with him and talked with him differently than they did with me. I also saw how different corporate cultures seemed to be "boys club" kind of places, and how I felt the need to be able to "hang with the boys" in those situations.

But before I go any further with this dichotomy, let me say that I know that there are gender stereotypes and biases, and it’s not all that simple. What I'm talking about here are very broad generalizations based and presented with the full understanding that not all men or all women behave certain ways. The following insights are speculative, broad, and by nature, imperfect. Yet I think looking at those broad differences can help us become more well-rounded leaders.?

And with that:

Thinking about that conversation with Samantha made me really think about the difference between how most men and most women lead, and I wanted to answer the question that her experiences brought out, namely: "What does leading like a man actually mean? And is it a good thing?"

Predictably, the answer lives in the gray zone. From our conversation, and with added perspectives of my own, there are lessons to be learned from both.

Lead like a man when it comes to perception. Perhaps it’s a survival tactic, like animals who—in situations where they must demonstrate dominance—transform themselves to seem bigger, fiercer, or even: more attractive. These acts of perception are available to all, and can be helpful to cue for others ones' place on the professional totem pole, including:

1. Speak with confidence Samantha describes her own “deep, low voice”, but what she’s really talking about is a voice that gets heard, that has substance, that would never end the sentence sounding like a question. The more women can own their opinions and decisions, the more they need to project them with confidence.
2. Banter for bonding Even if the locker room isn’t your happy place, that kind of jocularity creates a sense of bonding that signals to others that you can give—and take—a joke.??
3. Don’t take it too personally Interesting that Samantha says she “pretends” not to take it personally. And while she agrees that vulnerability is important, there are moments when a bit of an emotional shield can go a very long way.?

Many of us in the professional world have risen through the ranks under the leadership of men, and adopting some of these behaviors of perception are great skills to have—and I have also put them to use during my career. I have been mindful of maintaining firm handshakes; used my height and stature to my advantage; and don't shy away from correcting misperceptions of my role within the room.

In one extreme example of bias, after a successful pitch meeting with a premier financial institution, the Marketing SVP turned to me and said, "Well, when you type this up, make sure to include the full timing and pricing." I quickly responded by letting him know that I didn't do that, but I would surely pass that along to the person who did.

While female leaders like Samantha value the lessons she learned from men, she has always been committed to bringing more diversity and inclusivity into the world through media, and spoke to me about how she prides herself on leading like a woman.

And what I realized, was that there were good times for each. If leading like a man means presenting yourself with confidence, leading like a woman means acting with compassion.

Lead like a woman when it comes to action. When people talk about “soft skills” or “human skills”, (or as we like to say: “skills”), this is where many women leaders shine. Some of this may have to do with social learning and biological wiring, but others come from the realities of our experiences and the demands on our time. Samantha and I discussed the following:

1. Accommodate personal demands Women, statistically, have to not only manage their teams at work, but their teams at home. In fact, about 91 % of women with children spend at least an hour per day on housework, compared with 30 % of men with children1 and are eight times more likely than men to look after sick children or manage their children's schedules2. By recognizing that both roles—as business leader and family leader—are vital, Skey sets the stage for what leading like a woman is all about.
2. Be transparent While women are out there juggling these demands, it’s important not to pretend they don’t exist. Instead of hiding a child’s recital or teacher conference on your calendar as a “meeting”, leading like a woman means being transparent about these moments in our work day where our family’s needs come first. By showing co-workers and employees what prioritizing family looks like, we are also opening the doors for others to do the same. The more we can show other women what a healthy balance looks like, the more accepted it will become.
3. You are a part of your team Years ago, a client of mine was telling me how his wife was a way better leader than he was because she talked about her team as working “with her” and not “for her.” I thought it was such an interesting distinction and one I have managed to maintain ever since. When we talk about employees as subordinates, not only do we set up a power dynamic that doesn’t feel so great for those on the lower rungs, we are also neglecting the incredible support that our teams provide for us; without them, we are nothing.

In the end, leading with equal parts male and female energy—conviction and consideration, command and compassion—is what the best kind of leadership looks like.

Bio:? Samantha Skey is the CEO of?SHE?Media—a?media?company that includes brands like?SheKnows, Flow Space, StyleCaster, Soaps and TVLine.?Skey also launched the?SHE?Media?Collective and the Meaningful Marketplaces to support underrepresented creators and publishers and?Flow Space?that provides content, community, and commerce in service of women’s health.

Listen to the full episode below:

References:?

1- (Eige: Gender Equality Index 2021)

2- https://www.forbes.com/sites/maggiegermano/2019/03/27/women-are-working-more-than-ever-but-they-still-take-on-most-household-responsibilities/