Heather is the Chief Communications Officer of Chegg, an ed-tech company transforming the way students learn by reconnecting the link between learning and earning. At Chegg, she oversees both internal and external communications, policy and advocacy work, and the company’s philanthropic endeavors. However, like many of today’s modern women, she is multi-faceted. She is a leader, a mother, a mentor, a friend, an advocate for students, an ally, and much more. I reached out to Heather when I was an intern at Chegg, as I wanted to learn what she did to walk with purpose, confidence, and strength. After our chat, I learned that she came from humble beginnings and had an insane work ethic. During our first chat, she said, “If there is no room for you at the table, bring your own chair and make room for yourself.” Time and time again, she has given me great advice, so I wanted to share some of her wisdom through this interview. What message or advice would you give to recent graduates right now? First, you have to stay optimistic. We are living in an unprecedented time in our lives, and it is very challenging, but out of the most challenging and dark moments, beautiful things come from that. I keep seeing that image of the phoenix that rises from the ashes. I think a lot of people and communities are going to rise after this very uncertain time in history – and I am here for that! Second, I wouldn’t get defeated by the economic uncertainty right now. There’s still a lot that recent grads can do to keep themselves busy and to develop their skills. Volunteering, starting a new blog, or getting involved in any hobbies or areas of interest that you’re passionate about will keep your mind sharp and may open doors to future employment opportunities. And, I say this to all the interns all the time, but you really have to network, network, network. And don’t think you don’t have a network to start with. Even if you haven’t held a job reach out to professors and people that you know that are in the professional world and stay in touch with them. It’s harder now, given we are all living and working virtually, so you have to work at it, but it’s doable, and people will take the time if you reach out. How do you overcome feeling down and still perform at your best? Right now, I don’t overcome it. I really allow myself to feel what I’m feeling at the time. Some days are not easy, and it’s not to say that I’m not incredibly grateful for all the blessings that I have, but there are days where I feel like I’m struggling. I just allow myself to feel that way, and I don’t try to deny it. I actually think it’s really unhealthy to suppress those feelings. There’s that saying, “fake it till you make it,” but sometimes you just can’t fake it. We are all human beings, and there’s nobody that has it all together all the time. Nobody is saying, “I got this shelter-in-place thing down” because things are constantly evolving, and it is different for everyone. Some days you might feel isolated and lonely, and that’s okay. If you don’t bring your A-game to an interview or a project you were working on, give yourself grace. We need to really nurture ourselves, physically, mentally, and emotionally, now more than ever. Also, lower your expectations. And I don’t say that to encourage people not to aim high, to strive to reach their full potential, to achieve their dreams. To be honest, I am a very ambitious person, so this one is even hard for me. But things are really different during this pandemic, so I can’t have the same expectations of myself and I think people need to be accepting of what is doable now and not expect more from themselves, or others, than they are capable of giving as we all work through this. There will always be a time for incredible growth, professionally. Maybe now is the time to just invest in personal growth. What qualities do your closest friends have? Across the board, if you take a look at my closest friends, you will find a lot of similar characteristics. First of all, they are all hilarious. I have always been attracted to people with a great sense of humor and, especially these days, it’s good to have people around you who can bring light, levity, and humor to difficult situations. And I just love being around people that make me laugh. I also surround myself with people who really push and encourage me—it’s important to have people who can listen to you in your dark times, but not let you wallow in your pity party. People who encourage you to get back up, dust yourself off, and keep going. Find folks where you can be your authentic self. In the workplace, people often feel they have to put on a specific persona and behave a certain way to be successful, but I think it is really important to have people in your network, both personally and professionally, where you can just be you. If I didn’t have friends who allowed me to be a hot mess from time to time, and love me anyway, I don’t think I would have made it this far. I also have really long-lasting friendships, as most of those around me have known me since high school so, let’s just be honest, they know too much so I have to stay friends with them so they don’t spill any secrets. Is there a book or resource that you would recommend to people? Intentional Integrity, a new book out by my former colleague Rob Chesnut, is a fantastic read. Integrity is such an important characteristic in people and something I put a high premium on, both in those I work with and those I surround myself with in my personal life. It’s a super informative book and shares how we as individuals can operate with integrity and how a company can lead with integrity. It’s a trait more companies should be investing in, in terms of developing that competency across their organization, and I highly recommend everyone pick up a copy and read it. Is there anything that you’ve not been naturally good at and had to work really hard for? Um, everything? I feel like I have always had to hustle and work harder than those around me to prove my worth. I guess, if I had to narrow it down to just a few things, I would say that at the beginning of my career I was generally in roles where I was the one who was doing a lot of the day-to-day tactical work. As I advanced in my career and got to a position where I had to be more strategic and less tactical, I really struggled with that transition and letting go of some of the things I used to be responsible for. There are times where I slip back into the “doer” mentality and I really have to remind myself to step back and let others get involved in the work. One thing I have learned is that if I take something on for my team, it may actually be hindering their own career development. So, letting go, allows them to grow. And, believe me, letting go is something I have to work at. I am also driven by emotion and I trust my gut instinct a lot and, while I think that can be an asset to my leadership style, I also have had to work at being more data driven and analytical. The best results tend to come when you have a healthy mix of all of those skills at play. As a leader, what is a lesson you’ve had to learn? I’ve had to learn how to embrace failure. I’m a huge perfectionist; I grew up with a type-A personality, had to excel in everything in school, and always felt that nothing was good enough unless it was perfect. That’s just not the way the world works or the way you learn and grow or get better in anything. If you feel like you’ve already achieved the pinnacle, where do you go from there? At Chegg, the marketing team used to get together once a month to celebrate failure. We would ask people to tell us what did not go well in the month and what they learned from that. We didn’t want to know the achievements – we wanted to know what didn’t work. We would even have a cake and make it a party, and people would get excited about celebrating failure because there are so many more lessons that come out of failure than success. Always embrace the missteps because they will guide you to a much better path. What is one word that describes you? Loyal. I think, above all, that really matters in the kinds of relationships you develop personally and professionally. I want people to know that I can be counted on. That’s always been important to me and one of the ways I define myself. If someone counts on me to have their back, I take that incredibly seriously. And I will always show up for them. What is your favorite quote? Wow, I have so many. If I have to pick, one of my all-time favorites is this quote by Maya Angelou, because it really reflects how I have always tried to live my life. “I’ve learned that people will forget what you said, people will forget what you did, but people will never forget how you made them feel.” I don’t need to be the smartest person in the room. I don’t need to reach a certain level of success. But I do need to feel like I made someone’s life just a little bit better because I was here.
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