Deacon Spotlight: Kyle Olson

Kyle Olson (2004, BA in Religion)

Senior Legal Counsel at The Boeing Company in Chicago, IL

Tell us about your current job role/employer and what you’re currently working on. 

As Senior Counsel, I provide legal, business and strategic advice for Boeing leadership across a range of business units. My role at the moment is based on the Defense and Space division of the business, where I advise our supply chain teams in relation to some of the most cutting edge aerospace products in the world, including those that appear in Top Gun (both movies)! Before transitioning to my current role on Defense/Space, I advised the Boeing Commercial Airplanes’ Sales, Marketing and Strategy teams.

What key personal and/or career experiences led you to where you are today?

Upon graduating Wake, I was fortunate to attend King’s College London, where I lived in London and earned a Master’s Degree in Ethics. I made friends from all over the world, including my wife and many others who were studying for their own law degrees from King’s. It reinforced my decision to go to law school, yet with a global perspective. I graduated from Northwestern Law in my home city of Chicago, where I took not only the trial advocacy classes that drew me to law school in the first place, but also international law classes, including ones focused on human rights. This led me to The Hague, where I worked in the prosecutor’s office for one of the international war crimes courts, and eventually to Baker McKenzie, the most international of law firms that also had its founding office in Chicago. I knew I was fortunate to have the opportunity. Once a practicing attorney, I tried to seize it with humility, while re-learning the true value of grit, hard work, intelligence, and most importantly, humanity.

I made friends with those I worked with over those long hours and many years, which helped me stay grounded, keep doing the pro bono work I cared most about, and eventually make partner. Once I did, I had proven enough to myself to look beyond. So once Boeing called about a senior legal in-house position, I answered gladly. And through all of that, my wife and I welcomed two beautiful twin daughters, now 8, with one of them having a rare chromosomal abnormality called Trisomy 9 Mosaic, which leaves her wheelchair-bound, epileptic, along with many other needs. Yet she and her sister are so joyful.

So when my disabled daughter suffered a life-threatening hospitalization, I was moved to write a children’s book as a way of empathetically telling their story in a creative, hopeful, even funny, way. It was also a way for me to cope with such a painful time as a dad. In writing this book, “Sleep Like a Polar Bear,” it has forced me to pause and reflect on what really matters. I have been fortunate to have enjoyed a career of which I am proud. But I am so much more proud of what this book (now coming out!) means – for my girls and beyond.

What is the most challenging aspect of your job? How do you navigate that challenge?

Being a lawyer is hard for many reasons. For me, the hardest thing is often to let go, because the job itself never turns off. We lawyers spend so many hours, every day, scrutinizing for errors and other things to fix. And that is key to being good at the job. But sometimes the best thing is to stop and look up, and live life. The perfect can really be the enemy of what is already excellent. Spend that extra time, if not outside of work, doing something different in work – building relationships with clients and colleagues, and looking for ways to stretch skills. Take a pro bono case. Mentor an associate. Join a Board. Being a lawyer is a holistic profession, and not just a job. So remembering who I am as a person, holistically, helps me be a better – smarter and more empathetic – counselor for the clients who rely on me to be there for them.

What advice would you give to Wake Forest graduates about developing their personal life habits after college (finances, health, values, work/life balance)?

Pause from the race sometimes, even if for a moment. Take a breath and enjoy a simple thing like a cup of your favorite coffee. Sounds simple, but you have to make time to do what you enjoy, especially as life’s obligations mount over time. Life is in those moments. For example, I love music, so I play on my piano and sing (hearkening back to my a cappella and “rock band” stints at Wake!) whenever I have a free moment and need to decompress or just express myself, even if that means playing for an audience of little girls at home. That’s also part of what led me to write my children’s book – The chance to be creative for them, outside the strict confines of my job, led me to use skills gained through my job (writing, critically thinking) to do something different.

We know that relationships are important for any kind of development. How do you build and maintain your network?

I haven’t always been good at the “network” part of it, at least not in any formal way. (I only joined LinkedIn this year!) I’ve focused on relationships with people based, first, on respect, and also shared interests. And I’ve tried not to limit shared interests to work-related ones. Only being friends with other lawyers would be terribly boring! I find having a diverse network of friends and contacts makes the professional and personal journey that much more enriching. It can help with success too, in a very organic way.

Tell us about your mentoring relationships. What impact have these relationships had on your career and life?

Good mentoring (and be wary of those who purport to be good mentors for you and aren’t!) is critical for professional growth. Without my mentors, I wouldn’t have signed my first legal brief, questioned my first witness, led my first trial, or indeed had the perspective to expand myself into a legal role from a litigation partner at a firm to a senior counsel in house for a large company. Mentors have reminded me, including during times when I doubted it, I had value as a lawyer and person over my 15-year career in legal practice. They took the moments to teach me how to grow, even if that meant I initially had to fail; and they let me be myself the whole way. They tried to make me a better lawyer. They never tried to change me as a person. And I am very grateful for it.

What advice would you give to current Wake Forest students and/or young alumni who are interested in working in your industry?

Go get experience doing something – anything – in the field of law, all while remembering that who you are outside the field of law is what can count the most.

What’s next for your career? What future goals or plans are you pursuing?

Right now I’m seeing where my newly published children’s book will take me! That said, I’m content for now as a lawyer at Boeing and am excited to keep learning this vast and fascinating world. To infinity and beyond!

Story published in January 2025. For current updates on Kyle’s career path, visit his LinkedIn profile.