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Cynthia Pruemm: “In my opinion, communication is the number one leadership skill”

In my opinion, communication is the number one leadership skill. At times it can be difficult to put things into words, especially feelings, but you can’t expect people to read your mind. Openly communicating (the good and the bad) is vital to keeping your team together. Of course, as with anything else, you have to […]

In my opinion, communication is the number one leadership skill. At times it can be difficult to put things into words, especially feelings, but you can’t expect people to read your mind. Openly communicating (the good and the bad) is vital to keeping your team together. Of course, as with anything else, you have to find the right balance.


As a part of my series about strong female leaders, I had the pleasure of interviewing Cynthia Pruemm. Cynthia is currently the Vice President of SIS Financial Group, an independent financial advisory firm based in Hoffman Estates, Illinois. Before joining the retirement planning industry, Cynthia worked in the accounting field where she was a controller of a large corporation. Cynthia was a Regional Director for one of the largest nationwide senior market agencies where she also served as a Chairmen’s Council member. She decided to switch her focus from accounting to the retirement planning and insurance industry and started SIS Financial Group in 2006 with her husband, Hagen Pruemm. For the last eighteen years she has specialized in Medicare Supplements, Health Insurance, Life Insurance, and Long-Term Care Insurance. Together, Cynthia and Hagen are dedicated to helping pre-retirees and retirees with the implementation of comprehensive financial planning strategies to preserve and create wealth during uncertain and volatile times.

Thank you so much for doing this with us! Can you tell us a story about what brought you to this specific career path?

I started in this industry 20 years ago, working for a large nationwide company specializing in helping individuals navigate to and through retirement. As I grew and moved up within the company, I began to notice that there were things this company did that I did not agree with. I had always thought that when I get the chance to start my own company, I was going to do things differently. In 2006 I decided to do just that and opened my own independent financial advisory firm. Since then I have used my experience to help shape my company into something I am proud of and something I believe in.

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

Our first office was 400 square feet. When we were looking to expand, we found an office that was 1,900 square feet and thought it would be enough room for at least five to ten years. As we speak, I am taking a break from unpacking boxes. We now find ourselves expanding for the 2nd time in just three and a half years to our new 4,500 square foot office. Never in a million years would I have thought that we would be expanding at such a rapid rate. Looking back at that first office really puts things into perspective and gives me a new level of motivation.

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?

After starting my company, when I was hosting one of my very first retirement seminars, I bent over to pick something up and my pants split right before the presentation was about to begin. I spent the entire evening up at the front of the room concentrating on not turning around allowing my back to face the audience, which was not an easy thing to accomplish. I spent all week rehearsing and preparing for the presentation, but I never once considered the possibility of a wardrobe malfunction. The simple, yet important lesson I learned was to expect the unexpected and always bring a change of clothes with you!

What do you think makes your company stand out? Can you share a story?

We are a multi-faceted retirement shop that helps individuals with all aspects of the retirement planning process. From wealth management to estate planning to health insurance, we are truly a one-stop shop. This makes things easier for our clients, which is important to us. We are able to assist with all of the moving parts in one visit, which sets us apart from competitors. I’ve had clients tell me about how they didn’t have that convenience at the other firms they visited when considering who to work with.

Are you working on any exciting new projects now? How do you think that will help people?

We are currently in the beginning stages of developing a program that would approach young Americans and help educate them on the importance of planning for retirement at an early age. We find that too many people start late in life and we often contribute this to a lack of education at an early age. While it is never too late to start, the opportunities are much greater for those who start early. The young American worker can’t rely on pensions and Social Security like older generations once could. Now more than ever, it is important for Americans to take retirement planning into their own hands and to do so early.

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

You can’t always be all business all the time. You should also strive to develop a personal relationship with everyone on your team. Every morning when I walk in the office, I ask my team how their evening or weekend was because I truly do care about them and their time outside of the office. I make it a habit to say thank you when a task is done. I also communicate to my team when something went wrong so that we can evaluate the situation while it is fresh in our minds, learn from it and move on. It is as basic as it sounds, but in my experience, it makes a big difference.

What advice would you give to other female leaders about the best way to manage a large team?

There truly is no ‘I’ in team. You may think you can do it all, but the truth is you need to surround yourself with people that you can trust enough to delegate tasks to. It’s important to remember that they may not always do things exactly how you would do them, but as long as the task is done efficiently and correctly that shouldn’t matter.

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?

I would not be where I am today without my husband and business partner, Hagen Pruemm. Not only is he a great support system, but he pushes me to achieve goals I never thought I could reach. I know this is because he believes in me and wants to see me succeed.

How have you used your success to bring goodness to the world?

I am committed to helping anyone that comes into our office. I want to help them reach their goals and protect their future. I constantly educate myself on anything that I feel my clients can benefit from and I’m dedicated to making sure that I’m always up to date on current events so I’m giving my clients correct and relevant information. If my clients are not succeeding, I am not succeeding.

What are your “5 Leadership Lessons I Learned From My Experience” and why. (Please share a story or example for each.)

1) Communicate

In my opinion, communication is the number one leadership skill. At times it can be difficult to put things into words, especially feelings, but you can’t expect people to read your mind. Openly communicating (the good and the bad) is vital to keeping your team together. Of course, as with anything else, you have to find the right balance.

2) Lead by example

One thing I will never do is ask someone to do something that I’m not willing to roll up my sleeves and do myself. If one of my team members is tasked with making confirmation phone calls, I always offer to make the first few myself while they watch and listen. I take the time to explain how I did it and why I did it that way. This helps in training your team, but also in gaining mutual respect.

3) We have two ears and one mouth for a reason

Helping others brings great joy to my life, both personally and professionally. I believe that taking the time to listen to people is the best way to accomplish that. Gathering information and gaining a better understanding of the big picture before I do any speaking is something I constantly challenge myself to do.

4) Don’t be an armchair general

I’ve seen the bosses and colleagues that like to sit behind their desks and bark orders. For me, that has never been an effective. Instead, I choose to interact with my team and embrace the different skills and experiences. As a leader, it is my goal to be approachable. When I am meeting with a team member or even when I have an appointment with a client, I sit with them at a small table and not across from them at my desk. I want them to feel comfortable, not intimidated.

5) Embrace change

In my industry especially, you have to embrace change. If you don’t learn to just grab it and go with it, you’ll be left in the dust. Things change almost daily and I’ve learned that being set in your ways just doesn’t work. As a leader, I make sure to explain this to my team and constantly check in to make sure they are adjusting well.

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

I am a big believer in paying it forward. I think it goes a long way in both my personal life and my professional life. We’ve all received assistance from someone at some point, why not pass that gesture on. If more successful people could get on board with this mindset, I think we’d see a big change. At the end of the day it all comes down to being kind and helping others. Our world needs more of that.

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

Where there’s a will, there’s a way! Not everything is going to be easy and there will be many obstacles, but if you are determined enough and you put in the work you will find a way to get the results you’re looking for. This is something that I always remind myself of, especially when I was first getting my company off the ground. Going from a corporate environment to owning your own company has its challenges, but giving up was never an option for me.

Some of the biggest 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 🙂

Who doesn’t love Betty White! She was born just outside of Chicago, close to where I live now. At 97 years old, she continues to impress us with her stamina and witty humor. From what I can see she shows no signs of slowing down. She’s had a long successful career as an entertainer, and I imagine there’s much to be learned from her.

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