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Chrissy Lee: “Don’t wait for opportunity, create it”

Look for opportunities to be mentored — There were a handful of people that I’ve worked with that I greatly admired. I wish that instead of watching them from a safe distance, that I had the guts to go up and just ask if I could spend time with them, learn from them and be mentored by […]


Look for opportunities to be mentored — There were a handful of people that I’ve worked with that I greatly admired. I wish that instead of watching them from a safe distance, that I had the guts to go up and just ask if I could spend time with them, learn from them and be mentored by them. Most people are very willing to help.


As a part of our series about strong female leaders, I had the pleasure of interviewing Chrissy Lee. Chrissy serves as Co-President and Chief Operating Officer at Kalos Financial, Inc., designing and implementing business operations, driving strategic growth, managing the day-to-day operations of the firm, and working with advisors. Chrissy joined Kalos in 2007 and is responsible for the ongoing development and execution of firm-wide initiatives. She is also the Head of Operations and Transitions Dept., responsible for the vision and implementation of tactical operational initiatives. Since joining Kalos, Chrissy has held numerous positions throughout the firm, including Senior Vice President on the Kalos Capital side and National Accounts Manager for Kalos Management, where she was overseeing advisors’ accounts, trading, and implementing portfolios. Having worked both brokerage and advisory, Chrissy brings a unique skill-set to help advisors on both sides of the business.)


Thank you so much for doing this with us! Can you tell us a bit about your “backstory”? What led you to this particular career path?

Since high school, I have been passionate about the finance industry. I first started hearing about the stock market from a social studies teacher, Mr. Stevens. Mr. Stevens was a savvy investor who would research and trade on his accounts while sharing his experiences with his students. I was blown away by the process and research, and how people were growing wealth through investing. Eventually, after college, I started working for a company that focused on fixed businesses (annuities, insurance, ie.) to get my feet wet, but my goal was always to move further into the securities side of the business.

Can you share the most interesting story that happened to you since you began leading your company?

A clearing firm decided to remediate alternatives from their platform, and they gave us a short amount of time, and I was responsible for moving 4,500 accounts effectively within a 3 month period. During that time, I didn’t have that much guidance and had to basically do it on my own. I was coming in and working every night. We came in on Saturdays and sometimes on Sundays. I had to lead the team internally, encourage them to keep going, because we were working a crazy number of hours. I rolled my sleeves up and did the same work they were doing, while also working with senior leadership from both clearing firms because we were leaving one and going into the other. That was definitely the most challenging story and the first and hardest test in my leadership role.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Throughout our existence, Kalos Financial has always taken an all-hands-on-deck mentality, but especially in our early days. Because of this approach, I was often exposed to jobs and tasks I was not particularly trained in, including IT/AV duties at our national conference one time. Bear in mind, I had never worked with AV equipment in my life up until that point! Also, in between my AV duties, I was giving a presentation as the Head of Operations!

When it came time for the conference, speech-wise, I did well, but running the tech — not so much. At different points during the conference, I accidentally muted our CCO in the middle of his presentation, turned on the wrong mics at the wrong time, and may have put up the wrong presentation for a speaker.

They say everyone has a unique ability — AV was not one of mine. But I was able to show that I was willing to learn and do whatever the company needed of me, which is valuable in itself.

During that experience, I learned that no matter what position you are in, give it your all with 100% effort, and even if you fail, you’ll still be able to learn from that experience. Failure is a part of life and learning from those mistakes will only make you a more well-rounded person. During that part of my career particularly, it was important to show my bosses that I was willing to do whatever the job required and even though I made some mistake, they noticed the effort I put into the conference and it benefitted me down the line.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. What is it about the position of executive that most attracted you to it?

As an executive, I have the power to make a positive impact, which has always been a goal and a a focus of mine. I read a book called The Happiness Advantage by Shawn Achor several years ago that has resonated with me throughout my career. The book is about how and why people consider their occupation a job, a career, or a calling, and thankfully, I’m in the latter. I don’t think there is much purpose for anything if you don’t do it for a cause that is bigger than yourself, and my ability to help and affect people in a positive way is what keeps me coming back.

Most of our readers — in fact, most people — think they have a pretty good idea of what an executive does. But in just a few words can you explain what an executive does that is different from the responsibilities of the other leaders?

An executive thinks about the overall vision for the firm. It’s the executive’s job to determine company goals and figure out how to execute those goals. An executive needs to be constantly focused on building the business, seeking new opportunities, and being helpful to their employees so that they, along with the company, can grow and prosper. A typical day includes the implementation of goals and visions, meetings with department heads to ensure those goals are clear and being met, providing feedback and resources to people, and making sure all initiatives are being pushed forward and all deadlines are being met.

What is the one thing that you enjoy most about being an executive?

I am grateful for the opportunity to help shape decisions that I know will benefit our advisors and investors. I enjoy the ability to brainstorm, try new things and fail at new things — it brings me joy! At Kalos we are trying to help advisor’s grow their business, and we help them by being the trusted resource they need to make decisions, try new technology and ultimately drive their business to success.

What are the downsides of being an executive?

The pressure can be heavy. Sometimes, I get the sense that I have the world on my shoulders. There are so many decisions and tasks to get done, and never enough time. I also do not get the opportunity to spend time talking to as many employees as I should. Thankfully, I do have a great team of managers who allow me to delegate. I know my team is able to take projects on and manage the day-to-day details, which relieves some of the pressure on me.

What are the “myths” that you would like to dispel about being an executive. Can you explain what you mean?

As an executive, people tend to think that we’ve ‘made it’, and it’s not that difficult to manage people and make decisions. Managing people and teams are one of the hardest aspects of the position. In order to manage effectively, you have to have emotional intelligence and understand that you are not going to please everyone — and you need to accept that. The goal is to do what is right, not to please everyone.

Making decisions and implementing those decisions is incredibly challenging — you have the pressures of making sure things are executed properly and there is always the chance that it will fail. I don’t remember the last time I left work without thinking a hundred different things that needed to happen. To be sure I’m on top of my game, I tend to keep a journal with me so that I don’t forget my ideas and things that need to get done.

In your opinion, what are the biggest challenges faced by women executives that aren’t typically faced by their male counterparts?

We have made progress, but it is still very clear that women still have to ‘prove’ ourselves in a way men don’t, in order to have a seat at the table. Because of that way of thinking, we need to come more prepared with more ideas than anyone else at the table.

I think sometimes we also impose limitations on ourselves. We need to get better about speaking up, disagreeing with ideas, fighting for our projects, and having confidence in our ideas without being apologetic.

What is the most striking difference between your actual job and how you thought the job would be?

Although I knew that whatever position I was in, it would a calling and there was a purpose, I never imagined how much of my time and mind this position would take up. Rarely am I not thinking about what we need to do, should do, and will do.

Certainly, not everyone is cut out to be an executive. In your opinion, which specific traits increase the likelihood that a person will be a successful executive and what type of person should avoid aspiring to be an executive?

One of the traits I consistently see in successful executives is that they have a higher purpose for their life from both a personal and professional aspect. The most successful executives have a desire to create something that will impact a bigger audience, and there is a want to leave something that will outlast their own legacy.

Successful executives are also emotionally intelligent. They make sure all employees and the entire team, are doing well and are given credit for their hard work. They are honest with people, even when uncomfortable, because that helps build trust. The most successful executives are always willing to invest in people.

Those that should not aspire to be an executive are those that still struggle with people, always feel that they need to win, gossip, or make a name for themselves.

What advice would you give to other women leaders to help their team to thrive?

As I’ve made my way through my career, early on I was taught that I needed to present myself as someone strong. That I needed to come off forceful to be taken seriously. However, as I’ve grown throughout my career and have had the opportunity to work with some great female mentors, I have learned that being humble and approachable are so much more effective in leading a team. The team will trust you more if you are down to earth and human. I remember one time there was a project that needed to get done and we were in a time crunch. I rolled my sleeves up and helped with the project, and at one point, I said to the team, “Wow, this is really hard!” One of my team members came to me later that day and told me that one single statement I had said made the project worth it because not only was I willing to help get the project done, but I admitted to something that ‘executives’ usually don’t admit — the job was hard.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

My husband, Alex, hands down. Throughout my whole career, he has done everything to encourage me to keep reaching higher, even in times I felt limited in the environment. According to him, there is a limit to what I can accomplish. With that, it’s not just words, he shows in action. He has a successful career in sales, but to accommodate my hectic and long schedules, he has almost entirely taken over the task of school pick-ups, packing lunches and making dinner. Daniel Wildermuth, the CEO at Kalos Financial, once joked that Alex should get the card on Mother’s Day. In all seriousness, he has allowed me to grow my career, many times sacrificing his own. He is also very straight with me, so if I’m full of myself, he’s the first to humble me.

How have you used your success to make the world a better place?

Alex and I live purposefully, that whatever successes we have, our intention is to start the change from the micro to macro. Our philosophy for success is not “increase in our living,” but “increase in our giving.” We start with the local community, working with our Church to serve those in need through food, clothes, and resources like counseling. It’s much more than just giving food, which is important, but it has to be more. Our hope is to give them the resources and ability to eventually help themselves and pay it forward. Our next goal is to reach out globally.

What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

  1. It’s okay to make mistakes or fail — I spent too many years focused on making every task perfect, so I missed out on growing. When I was in Operations, I spent so much time making sure every piece of paperwork was perfect that I ended up spending too much time in the minutiae.
  2. Look for opportunities to be mentored — There were a handful of people that I’ve worked with that I greatly admired. I wish that instead of watching them from a safe distance, that I had the guts to go up and just ask if I could spend time with them, learn from them and be mentored by them. Most people are very willing to help.
  3. Don’t wait for opportunity, create it — This is a very important lesson I’ve learned in the past 8 years. This is particularly true with women, because so many of us grow up being taught to be polite and ‘wait our turn.’ I realized opportunities do not fall on your lap, you have to either create it yourself. I’ve also learned to take on tasks that no one wants to show impactful you can be.
  4. Embrace how others approach their life and career — I learned this late in my life but once I understood it, it was freeing. I stopped micro-managing people — meaning, I didn’t try to make them do things the way I do things. I started leading, which means that I added guidance to the way they did things. When I started realizing that everyone has a different unique ability and we all play different functions in an organization, I let go of my stubbornness and started respecting how others do their work.
  5. It’s okay to be a woman — I thought to ‘make it’ in an industry where the majority of men are the ones in executive positions, I had to fit in and not show my feminine side — that I needed to be dark suits, speak boldly all the time, and never show weakness. I realized that’s not authentic, that’s not who I am. I enjoy being a woman and the wonderful feminine traits that come with that. I realized there is a difference between being respected through hard work and allowing your personality and character come out authentically versus being someone that is not you, trying too hard to be taken seriously.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.

I would push an initiative to have all universities teach courses on personal finance, and career development. I wish our college/university systems taught more than school subjects. I am constantly amazed to find young people graduating without any true life skills, like how to budget, how to invest, how to build a resume, how to interview. These are skills that will impact you for the rest of your life. I certainly understand that it starts in the home first, my husband and I taught our children very early on the importance of budgeting and investing. They both had brokerage accounts and we taught them how to research companies and allowed them to make choices in the companies they wanted to invest in. They learned that it’s more fruitful to invest in those companies than to spend your money just buying their products. We also taught them about the difference between choosing your ‘dream school’ versus going to a good, practical university and coming out debt free.

It would much such an impact if kids were taught both at home but also in their post secondary education, those resources to help them truly prepare for the real world once they graduate.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“There is freedom waiting for you,
On the breezes of the sky,
And you ask “What if I fall?”
Oh but my darling,
What if you fly?” 
― Erin Hanson

This is a poem I recently read, but I’ve lived this quote in my life the past 15 years, without knowing the quote existed. I’ve grappled with an ambition to always grow, flourish, keep opening doors but with a distinct fear of failure. There is a thrill of trying something completely and wonderfully new in an organization, but at a cost of some sleepless nights and complete anxiety that covers you. I’ve finally accepted that challenge and pushed through the fear, to just go for it.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them

Ann E. Dunwoody — retired general of the United States Army. She is the first female in U.S. military to become a 4-star General. I’m in awe of what she has accomplished, to lead our finest, in a field that is predominantly led by men. She is also incredibly humble in her approach and very authentic in leading through her character. It would be incredible to just hear all about the challenges, successes, and failures she has gone through.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.


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