Leadership, Fashion and the Future

The Tara Dress by Jennifer Hamilton for Prim & Wilde

The Tara Dress by Jennifer Hamilton for Prim & Wilde

I recently had the pleasure to be introduced to Leadership Training expert Jessica Osedach while we were both spending the weekend at an exquisitely renovated home in rural Vermont. Over fine wines and gourmet food, the dinner party conversation started with a lyrical debate about success and whether leaders are born or made, but was quickly corralled by Jessica's experienced point of view and captivated by her crisp insights and laser-sharp vision of leadership in a changing world.

Back in Manhattan, I immediately jumped on the opportunity to ask her to share some of her insights on women, leadership, success and of course...style, with me.

We met at a cosy coffee shop in the heart of the new financial district of Manhattan – midtown. I could spot Jessica from a distance, striding across the Rockefeller Plaza – an extraordinary blend of delicacy and strength, which she extends to her business wardrobe – she wore an elegant ivory shift top with a pair of tailored pants, topped with a magenta silk jacket.

PW: What does leadership look like?

“Leadership is conveying confidence, even in the face of not knowing, or in the face of challenging situations.  It looks polished, 'put together,' elegant as opposed to noisy.  It's like the eye of a hurricane - remaining calm and composed even when surrounded by chaos, change, swirling priorities.”

Jessica explained to me that seniority itself is actually an important part of leadership. Seniority is not just the time spent learning and growing, but the ability to share, coach, mentor that comes with experience. We are constantly growing and a leader knows that they can share their knowledge because they are still learning. But seniority does not only come after 20 years in a position, it is a constant that starts with each accomplishment. Transparency is key to leadership.

How do women feature in your program? 

“Women in executive level roles are still a minority in some functions but their numbers are growing.  In our program our women participants are equal to men in every sense of the word.”

How do women react to leadership?

“Every woman reacts differently - some may initially be anxious about being in charge, others act as though they were born to take that role.  I really think that we've arrived at a time where individual differences between women drive how they react to leadership, as opposed to their gender alone.  There are so many different kinds of women!”

How do women lead differently?

“I don't think that they do.  On the whole you have tough authoritative bosses, you have more collaborative bosses - I don't think that gender drives the majority of these differences anymore. It has to do with who these bosses are...their gender along with hundreds of other attributes. I will say that women may have a more complicated landscape to navigate. Appearance does matter more for women...tone might matter more. Think of Hillary Clinton. Is Bernie Sanders really that much more 'like-able' than her or is she being held to a different standard?”

Is it totally superficial to consider your appearance?

“Not at all.  It's critical. For better or for worse people start to form judgments about other people upon first sight.  In the workplace, how you choose to 'show up' – including what you decide to wear – is part of your professional image. It's better to be intentional about this than to ignore it.”

What could women do to make themselves better leaders?

Let me preface this by saying that I found this to be the most interesting part of our conversation. Jessica stunned me with the simplicity and vulnerability of her answer. She told me that emerging leaders “should be open to feedback and willing to change.  Remain flexible and adaptable.” Jessica recommended that everyone do some soul searching to make sure you know what you want in terms of career goals and that those goals will actually make you happy. Then go for it.

Thanks Jessica. I consider myself so fortunate to be able to meet and talk with women who can so brilliantly talk about their work and Jessica, like the leaders she works with, is truly transparent and willing to share her knowledge.


How Rock Climbing Can Help You Reach the Top of Your Career

You reach out, shift your weight slightly, reach again. Fail. Fall. Chalk up, swing yourself back, reach again. Fail. Chalk. Try again. A little closer this time. Fail. Fall. Catch. Chalk. Reach.

The sweat and chalk of rock-climbing and the business of fashion – seemingly so far apart, but stand any rock-climber in front of the mirror and you will see someone en route to the top.

I have had three passions since the age of six that have been running concentric circles around each other, providing me with balance, drive and a sense of direction and honing my vision.

I learnt to sew when I was six, developed a passion for writing at eight and started running when I was  ten. In my teens I bought books on design and taught myself pattern-making while competing in national track competitions ... and documented it all in a combination of fiction and fantasy on paper.

I still love to run, but now I have broadened my sports resume to include whitewater kayaking, mountain biking, snowboarding, skate-skiing and rock-climbing. Each of these sports has taught me so much about life, technique, strategy, pain, survival and knowing that failure is just the start of success.

I recently overheard a conversation at Brooklyn Boulders where a very beautiful and graceful woman, obviously early in her career, was relating her office politics to her climbing partner saying “...my co-workers don't like ambitious women, but I can't be any other way. I just want to reach the top and I'm going to get there.”

And that is just how it is with rock-climbing, your ambition and drive lures you to the wall where you try, and try again, to reach for the top. Your journey is clearly delineated between the goal and the route. Failure does not mean you give up, it is merely a challenge – a challenge that you need to go back and work on again and again until you can solve it and move past.

Rock-climbing requires balance, strength, technique and commitment. Commitment will guide you through failure, it will drive you back to revisit the problem in a fresh way. You need to unerringly rely on others, knowing that they are going to support you and knowing that you will support them too. You learn technique and develop a strategy. The struggles of rock-climbing mirror the difficulties of running a company, you have to stay true to yourself, but rely on others. You have to be accepting of failure, yet understand that failure is just the wrong route, it is not personal, it is trial and error, an opportunity to choose a new route, explore a fresh approach. Business is full of challenge, and it is your commitment to getting past the challenges that will determine how your business or your career is managed.

So...take a risk, reach for the top and...climb on.