Interns into executives: An interview with Abby Moskovitz

We’re proud to bring you another installment in our series featuring women leaders at Hyland. We interviewed Abby Moskovitz, Assistant General Counsel at Hyland, about having a fulfilling, challenging career.   

Question: How did you get to this point in your career?

I have always been open to change. I moved around quite a bit. I don’t always think that’s a good thing, but in my case, it has been. For a long time, I wasn’t sure if being a lawyer was right for me. When I decided to go to law school, my dad, who is also a lawyer, told me that going to law school was a great idea and I would learn a lot, but I should never practice law. He said I would spend my life butting my head against others’ and I would be miserable.

I decided to go because I wanted to be an FBI agent and getting a JD would help. By the time I was done, my dream of being an FBI agent had faded and I spent the next 11 years working for law firms of various sizes. I had a focus on intellectual property law, which has always fascinated me. I am very conflict-adverse, however, and the adversarial nature of the work was stressful for me. I hated that part of it.

Moving to an in-house position was the best move I ever made. It’s very different from working in a law firm. I really like working with others for a common goal – it’s much less adversarial than the work I was doing in the law firms. I also love learning about the business. I have been with Hyland since 2010, with a short gap in 2014 when I moved to Maine and worked for a period of time at another company. I realized quickly that it was a mistake to leave a special place like Hyland and I am very grateful they took me back.

Q: What woman inspires you and why? 

This is a hard question! The first person who comes to mind is my friend, Ellie. Ellie lives in Mozambique, Africa, and she is the director of an NGO there.

Although the work she does is very inspiring, it’s the way she communicates with people that is so special. She connects to everyone – whether it’s somebody on the street, somebody she’s working with, or somebody who works for her – in an unusually genuine manner. It comes naturally to her and I am in awe of it. It is a magical trait.

Q: What is your favorite perk at Hyland?

The value placed on taking time off. Whether it’s sabbaticals or flex days, it’s a culture that respects an employee’s time away. That is reinforced throughout the company because, to make it work, everyone has to step in and help out, and everybody does. It makes life better.

Q: Looking back at your career, was there an obstacle that you overcame to help you get to where you are today?

I can’t think of a specific moment in time or a particular life circumstance, so I’m going to say facing my fear of making mistakes. That fear can be really paralyzing. We all make mistakes. I have made my fair share of mistakes at Hyland and I am still here.  I don’t think anyone ever completely gets over this fear, but I am getting better.  If you don’t get out there and make mistakes, you can’t learn from them.

Q: If you could have lunch with anyone, living or dead, who would it be and why? 

This is easy for me. It would be my mom. She passed away when I was 12, so we would have A LOT to talk about.  

Q: Work-life balance seems to be kind of a big deal here at Hyland. Do you have any tips for balancing personal and professional life? 

Yes, work for a place like Hyland. That is the key to balancing personal and professional life – more than any specific things that I do myself to make it happen.

I am hyper-focused, so when I am thinking about work, my whole family knows it. I am just not “there.” I really have to shut down work, both literally and mentally, so I can be with my family. This is challenging, but the emphasis on teamwork at Hyland allows me to do this.

Q: What is the biggest challenge you face as a leader in the tech industry? 

Having the confidence to ask questions. I hate feeling that I have asked a question that I should have known the answer to. It makes me cringe, and I harp about it for a long time.

At the same time, there have been too many instances when I have walked away from a meeting kicking myself for not asking questions! This has helped me realize it’s worth cringing from time to time because you’ll never learn if you don’t ask. 

Q: If you had one word to describe your time at Hyland, what would it be? 

Fulfilling. I am challenged, I am learning, I am growing, and I’m having fun. 

Q: What does #HylandLife mean to you? 

I think it means making your work more than just a job. It’s about work being a place that you want to be and being around people you want to be with.

 Q: What is one question you always ask a potential hire during an interview?

I have only been a manager for about two-and-a-half years, and I haven’t done very many interviews. I remember the question that Tim Pembridge, our VP, General Counsel, asked me in my interview, which I really liked, so I am going to steal it:

“Tell me one thing about yourself that I wouldn’t know from looking at your resume,” he said.

This question says something about the values of the company and what they look for in an employee. It isn’t just about education or work experience.

At the same time, from the position of the interviewee, the question loosens up the conversation. It allows you to talk about things you aren’t nervous about – you can bring the conversation around to your hobbies, your family or something else familiar – and you can be yourself.

 Q: What is the most rewarding part of your job?

It really is the people. I have so much fun with the people I work with, within the legal team and in other departments. Things change rapidly at Hyland, so we are all figuring it out together.

Recently, Tim sent me an article about a study they did at Google around the productivity and the value of work created by teams. It describes the concept of psychological safety. Teams that speak freely and socialize while getting work done are generally more productive than those teams that are more rigid and stick to a strict agenda. This is because they feel safe to ask questions and take risks. Making that connection with the people that you’re working with is very important – it leads to more valuable work and it’s also a lot more fun.

Q: What was your dream job as a kid?

First, I wanted to be a vet, but then I decided I couldn’t handle the blood, so I was just going to run a pet boarding business. Then, I decided I was going to be a math teacher, which then somehow turned into an FBI agent.

Q: Do you think there is one characteristic every good leader possesses?

There are so many characteristics that a good leader needs to possess. One particularly important one is the ability and willingness to listen. Leadership can’t happen in a vacuum, and a good leader needs to engage others to learn what is working and what isn’t working, what needs to change and how, what effect his/her decisions and actions are having or will have on others and the business, and on and on.

Q: What piece of advice would you give your intern-aged self?

Be open to change.  Just try it! If you don’t like it, try something else.