In Conversation with Conner Gilliland

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Tell us about your background: 

I like to take this answer back to the very beginning—my background in the fine arts. I grew up immersed in theatre and music, which provided me, very early on, a world where I could simply create, imagine, and be anyone I wanted to be. Since my childhood, my life has taken many twists and turns I could never have imagined, all beautiful in one way or another. In all of this, I realized that the same passion for creativity and imagination never went away. Now I think about how I channel that passion and use the voice I’ve cultivated into the world of business. 

My career in HR has seen so many parallels to the life lessons I learned through the arts. I grew up immersed in theatre and music, telling the stories and living in the shoes of many characters--just like you and me--but somehow, they seemed bigger than life. As an HR Leader, I get to help orchestrate workflow, capitalizing on the strengths of the most important asset of a company, its people. ​I get to share in the stories and lives of individuals, reminding them of the value they bring, that their story is extraordinary, and most importantly, that their story is their own​.

My career began in the oil and gas industry. While I am thankful for the opportunities and experiences I was given, I always knew I belonged in a more creative role and industry. This all leads me where I am today, as a Talent Relations Manager at Wayfair. In this role, I work alongside executives and other leaders, coaching them to get the most out of their teams and build highly productive organizations. 

What do you wish you’d known when you started out?

  • Just breathe. Don’t try to do too much, it takes time to learn a new job and a new company. Embrace the opportunity and take the time to learn. Be patient with yourself.

  • It’s OK to realize the first job you take doesn’t have to be the job that takes you through to retirement. I grew up in a family and environment where many of the people around me had done the same job for over 20 years, some over 30. I always took this to heart, and felt somewhat torn when I realized I didn’t want to be with my first company anymore. While it may be that your first job is your last, don’t hesitate to make a switch, particularly if your job is not giving you the energy you need.

Best career advice you've ever received?

Do what energizes you the most when you’re most energized to do it.

The workday can feel long, and inevitably we find ourselves caught up in menial and administrative tasks at some point during the day. Ask yourself, what really energizes you right now in your job? Are you making sure you are prioritizing this activity when you are most alert and creative? For me, I do a majority of my creative work at the beginning of the day.

What leadership qualities are important to you?

Empathy stands out as the most important leadership quality in what I call the “new age” leader—A.K.A. the millennial leader. We can’t fully expect employees to bring their full selves to the office every day, but their most evolved self. To work in this mindset of how employees show up, it takes a leader who sees and values their teams as humans, first and foremost.

Vulnerability is another critical trait for me. It is OK to not know the answer, it is OK to recognize you still have things to learn, it is OK to fail. Innovation and creativity can only go so far unless you are willing to be vulnerable to the fact a solution may not work the way you intend. 

What has been the biggest challenge in your career so far? 

Is it too cliché to say 2020? This has been a year where, in the middle of a global pandemic, I quit a job, started remote with a new company, and completed a cross-country move. This has caused me to reflect on how I show up as both an employee and people leader, and I think it has brought out these traits mentioned above even more. 

Another interesting challenge this year has presented is how we talk about mental health and well-being in the workplace. As mentioned above, more employees are bringing their evolved selves to work. This is even all the more prevalent when those employees aren’t leaving their homes to do their jobs. A challenge has been normalizing this particular conversation, but in discovering  how to do this, I now see it as evolving the workplace to be more of the “safe space” we hoped it would be. 

And for fun, what is your favorite wardrobe staple?

In every man’s closet, there should be at least one pair of Oxford dress shoes. I must admit I am a shoeaholic—the easiest purchase for me to make is always a new pair of shoes.

For fun, I love to workout, particularly indoor cycling. I am currently in training to be a part-time spin instructor at Rev’d Indoor Cycling here in Boston. Catch me on the podium soon! 

Follow on IG for lifestyle content and workouts: https://www.instagram.com/cmgilliland1/ (@cmgilliland1)

Join my LinkedIn network: www.linkedin.com/in/connergilliland

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