5 Things Young Women Wonder Answered by Female Leaders

Gianna Wilson
Achieving Our Greatness: The Intern Story
6 min readAug 25, 2020

The year is 2020 and I am one of four female interns working on a predominately female team. One hundred years ago, nothing about that sentence would hold possible or even make sense. Even ten or twenty years ago, I’m not sure it would be feasible. All I can say is that I am glad to be living in the year 2020 (despite the pandemic and complete upheaval of our everyday lives). Why? I am fortunate. Fortunate to be working with women, led by women, and learning from women in the field I love.

Now obviously, I am not the only one impacted by this since I am surrounded by women. So, I decided to reach out to some of the leaders within my company and teams specifically to find out how they got to where they are today and see if they have any tips for me as a young woman starting out. I found their candid answers to be very interesting, insightful, and a bit humorous at times… I hope you do too.

Jen Kaye (Left) and Michelle Boockoff-Bajdek (Right)
Jennifer Tomosivitch (Left), Valerie Ward (Middle), and Allison Stamm (Right)

1. If you could tell your 20-year-old self just one thing, what would it be?

  • What you think you’re going to do the rest of your career, is most likely not going to happen. Always be open to change. — Valerie Ward, Scrum Master — Team Lead
  • Believe in yourself — your capabilities and your potential. Always display confidence and take risks to try things out of your comfort zone. Learn to speak well and with authority. — Jennifer Tomosivitch, SVP, Global Portfolio Marketing
  • Be kinder to yourself. There is no need to punish yourself for every misstep or poor decision. We learn the most from our failures and there is no shame in that whatsoever. So, pick yourself up, dust yourself off, write down what you learned, and move forward. — Michelle Boockoff-Bajdek, Chief Marketing Officer
  • Don’t freak out about your liberal arts degree. I always felt like I was fooling everyone into thinking I was competent, the epitome of imposter syndrome, because they all had business degrees. Looking back, I was a rock star, and I can’t believe I allowed myself to feel so inept. — Allison Stamm, Corporate Communications, Brand, and Competitive Intelligence Lead

2. What has been the biggest challenge being a woman and getting to where you are today?

  • Getting over people’s misconceptions of what a female can do. I’ve always been in technical roles or dealt with technical products and I’ve always felt that I had to work harder to prove that I do know what I’m talking about. — Valerie Ward
  • Gaining respect from colleagues and partners. As a somewhat younger woman, I’ve found that respect is not as readily granted by more seasoned colleagues than it is for male counterparts. — Jen Kaye, Senior Manager, Communications
  • This may sound contrived, but it’s true: lack of female leadership and mentoring. Also, I did not have a true mentor until seven years ago, and I didn’t realize nor understand the value of having someone who could help to guide and support my career. If you don’t have a mentor, please find one. — Michelle Boockoff-Bajdek
  • I have been fortunate enough to work with many women in senior leadership roles, and more often than not, have reported to women. But that is isn’t to say I didn’t work primarily with men, and I think at one point I over-indexed on fitting in: I think I tried to be too serious, too what I considered to be “professional,” and too adaptive to work styles that were not naturally my own. Once I stopped doing that was when I actually began to see more success. That, and not visibly rolling my eyes whenever I am mansplained to. — Allison Stamm

3. What is one piece of advice you would give to a female college student about to graduate and enter the workforce?

  • Learn everything you can. Make yourself indispensable. I’ve gotten put into roles and given opportunities because I was the “only one who knew how to do it”. — Valerie Ward
  • Don’t be shy. Actively and widely network communicate your ability and willingness to solve business problems big or small. — Jennifer Tomosivitch
  • Don’t expect that your career will chart a linear course. There will be twists and turns, some backwards steps, and of course, opportunities. And there is nothing wrong with that; every new opportunity helps you to grow and ultimately thrive, both professionally and personally. — Michelle Boockoff-Bajdek
  • I think that it is important to work hard, absorb like a sponge when you are getting started, and don’t be too focused on a particular goal. If I limited myself to focusing on a single path, I would have missed out on a lot along the way. — Allison Stamm

4. What led you to the position/job you have today?​

  • Proving that I can lead groups of people. I never ever wanted to be a manager, but I’ve been told numerous times by reports who have 15–20 years’ experience on me, that I was “the best manager they ever had” and they said that it was because I never made them feel like I was above them. — Valerie Ward
  • Interest to diversify my career into a new industry — tech. — Jennifer Tomosivitch
  • It wasn’t easy, to be candid. It took a lot of hard work, dedication, and professional growth over many years, along a robust career path. It’s also required an (almost) unwavering belief in myself and my capabilities. — Michelle Boockoff-Bajdek
  • Luck. But I say that, tongue slightly in cheek, because luck is really being poised and ready to recognize and take advantage of opportunity when it presents itself. — Allison Stamm

5. Is there anything you would change/do differently in your career path if given the opportunity?

  • Not too much, except for maybe sticking up for myself a little more, especially in the beginning. — Valerie Ward
  • I wish about 10 years ago I had thought (or had someone suggest) to reflect purposively on what and where I wanted my career to go and then build a more structured career path/development plan. In the end, I am proud of myself. — Jennifer Tomosivitch
  • There is no need to rationalize the decisions we make. When I took a job in Manhattan that required me to commute weekly from Boston, it meant sacrificing time with my family. And, I told myself it was worth it; my family would be fine and *quality* time was what really mattered. It was a load of crap. I made myself believe something that just wasn’t true. I took the job because I didn’t dare miss out on an amazing opportunity. And it’s okay to make those decisions, as long as you’re honest with yourself about why. — Michelle Boockoff-Bajdek
  • I try not to look backwards, because every misstep gets us to where we are today, but I might speed some things up, if given a do-over. Every time I agonized over doing something, like quitting a job I hated, or moving across the country for a new opportunity, it always turned out to be a really great decision. Trusting my gut more, earlier, would have saved me a lot of angst. — Allison Stamm

Now I am no expert, but I consider these women to be. Take their advice…I know I will.

Plus, the advice about being a sponge makes me feel less guilty about being such a bookworm…

Spotted: Me at my favorite vintage bookstore with a coffee in hand, pre-quarantine.

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