Interview with Cindy Smith and Courtney Smith of The Lakeside Group Association

Tell us about your company, it’s purpose, mission, target audience, goals, what makes it unique.

The Lakeside Group Assoc. Inc. is an executive search firm based on the philosophy of Total Life Improvement. The Lakeside Group offers career advancement throughout the United States in the Aerospace/Defense, and Alternative Energy sectors. We provide our Clients top talent in these industries while cultivating our network of Candidates. However, our goal is to change the perception that one’s career is the defining factor of their success. Genuine success is measured in several aspects of one’s life such as family, health, spirituality, etc. We intend to be a resource for Total Life Improvement, as well as career opportunities. 

How did you come to work together in the first place?

Cindi: First and foremost I am a single mom. In 2002, my husband unexpectedly passed away. At the time, my daughter was just 15 years old and my son was just 6 years old. This tragedy, as well as other challenges we have faced throughout our lives, have shaped Courtney and I into very committed, strong and determined women.  We have learned to persevere even under the most challenging of times. Although this was a devastating time in our lives, we have each learned a great deal about ourselves and our inner strengths which gave us the confidence to pursue our vision of The Lakeside Group.

In 2006, my industry was caught in the economic crisis. I had been self employed for sixteen years, eight of which was spent as a Consultant/Realtor to a custom home builder/developer. This entailed interviewing and hiring architects, subcontractors and employees; as well as identifying and negotiating on multi-million dollar land development projects and homes.  It became evident that this builder would have to close his doors, so I put together a resume for the first time in sixteen years and sent it off. I was contacted by an executive search firm to see if I would have interest in recruiting. During my time with the recruiting firm, I found that it was quiet similar to my real estate career. Rather than match people with homes, I was matching them with career goals. Unfortunately, due to an unforeseen situation, I was laid off from this search firm. Because of the success I had had while at this firm, I decided to open up my own executive search firm, The Lakeside Group Assoc. Inc. The first person I recruited was my daughter, Courtney!

Courtney: When my mom established The Lakeside Group, I was working part-time as an Assistant Manager and also was a full time student at Baldwin Wallace College. I helped her with the initial setup of the office, computers, phones, etc and would stop by in my free time to assist with the recruiting. After six months, I left my position as Assistant Manager and joined The Lakeside Group full time. I have been here ever since!

Please describe your respective roles in the company.

Cindi: My role in the company is to be a leader and visionary. There is not one part of the company that I haven’t done or wouldn’t do. Because of my background, my strengths lie within marketing, negotiating, business development, and strategizing. I am a “people person” and enjoy these aspects and challenges of the business. On the other hand, I have a great distaste for accounting, research, documentation, and anything that has to do with the computer! These are the areas where Courtney excels and really is my “better-half”. She has also performed every aspect of the business but thrives on areas such as finding Clients and Candidates, digging online for specific phone numbers/names, computer maintenance bookkeeping, and record keeping. We make an excellent team, not only because of our similarities but also because of these differences.

How has working together affected your relationship outside the “office.” 

Cindi: Keeping family/work matters separate has been fairly easy. I see these as two completely different subjects, so when Courtney and I are at work, we are focused on our work goals and objectives. In regards to family issues, we handle these scenarios much the same as we did before. When we were both employed elsewhere, we would discuss family issues outside of business hours.

What are some of the challenges you have faced working together?

Courtney: The division of responsibilities has been very clear from the beginning. Usually, the tasks that I don’t want to do, my mom loves to do, and vice versa. Also, I wouldn’t say that there has been much of a power struggle, per se; just an occasional difference of opinion on how certain situations should be handled. For example, we are in the process of creating systems for future employees. While I may feel strongly about one idea, my mom may feel strongly about another. Although this can cause some conflict, this difference of opinion helps us to create a better resolution. Having both of our views give us a perspective that one of us could not reach alone.


We have shared so many achievements over the past couple of years! We celebrated our first placement together, we saw the business double annual revenues in 2008, we won the Micro to Millions award from the organization Count Me In this past December, we hired our first part-time employee, and in June of 2009, we will hear if we are a finalist for the Cartier Women’s Imitative Award competition. Our favorite motto sums it up:

Life is not a journey to the grave with the intention of arriving

safely in a pretty and well-preserved body, but rather

to skid in broadside, thoroughly used up,

totally worn out, and loudly proclaiming,

“WOW! What a Ride! “

What do you like best about working together? Least?

Cindi:  One of the greatest benefits in working with Courtney is that I have 110% trust and faith in the person that is helping to lead The Lakeside Group. This is a type of trust that you cannot get with just anyone. Her level of commitment is inspiring and pushes me harder to make The Lakeside Group even more successful. She provides a new, savvy, fresh insight that comes from her generation. Courtney brings out the best in me and has taught me to slow-down and take things one step at a time. I greatly admire her dependability, her unwavering strength, her optimism, and her dedication. It has also been a great pleasure to watch Courtney transform into her own entrepreneur.

One thing I have learned from Courtney is that she is not a morning person! This can make our mornings challenging sometimes, since she is not always open and flexible. Knowing this about her personality, I try to plan important discussions and decision making later in the day. I must say, I consider myself fortunate if this is the worst I have to deal with!

Courtney: I really enjoy working with my mom on a day to day basis. I have gained great insight by working with her on a professional level. My mom’s entrepreneurial mentality has inspired me to exceed in ways that I had never before considered. She has opened my eyes to the unlimited potential I have in myself and the endless possibilities my future can hold. She has exposed me to a broader way of thinking and has taught me the importance of “staying positive”. She motivates me to be optimistic and hopeful even when our situation appears otherwise. So, I would have to say what I enjoy most when it comes to working with my mom is the professional life lessons that I have learned and continually learn in the office.

Of course, there are some things about my mom that drive me a little crazy too! She tends to have an “on the go” type of personality, so she is always doing something and there is always something that needs to be done. At times, this can make work a bit overwhelming. But, I have learned how to deal with these instances and realize that I can only do one thing at a time. 

What, if any, big challenges or little annoyances have occurred as a result of working together and how have you managed to overcome them?

Cindi: One of the biggest challenges that we have had to overcome is working around Courtney’s college schedule while still trying to be productive. Because this is Courtney’s last year, her choice of class times is somewhat limited. However, even with her schedule, she still manages to work 40+ hours a week, even if it means working nights and coming in on the weekends. In addition, there are some things that I hadn’t even realized would be a problem until the situation actually arose. For example, taking a family vacation has become increasingly difficult. If both of us are out of town, there is no one in the office to manage the business. As for the little annoyances, Courtney enjoys listening to music while we work, which is a huge distraction for me. To resolve this issue, Courtney will usually wear headphones or will put the radio on when I am doing something that does not require a lot of thought.

Courtney: One of the most difficult challenges I have had to overcome was the decision to put graduate school on hold. I am a Psychology major and the majority of the careers in my field require either a Master’s degree or a Ph. D. I had originally wanted to pursue my Ph.D. in Clinical Psychology and start graduate school in the fall of 2009. However, after a lot of thought and consideration, I decided that I wanted to put graduate school on hold and help my mom grow The Lakeside Group. I am excited in the amount of potential the business has and truly enjoy my role and responsibilities. I have not completely dismissed the idea of graduate school, but rather, am considering this avenue a “Plan B”.

What tips would you share with our readers for working with a member of the family?

Working with a family member can be extremely difficult, but rewarding as well. The majority of your family will not be a good fit; there will probably only be one or two members of your family where this arrangement would be beneficial to both. It is important to be upfront and lay out all expectations, responsibilities, concerns, and limitations prior to entering this arrangement. Also, realize that any one of these categories has the potential to change as time goes on. Seeking outside resources, such as a business coach, can be greatly beneficial. This provides an objective third party which will help to enhance the good ideas from both family members, as well as, sort out the ideas where there are differing opinions. Lastly, take your time when making this decision. There is no reason to rush and sometimes you may have to rely on your gut feeling.

What’s been the most exciting thing that has happened as a result of working together?

In December of 2008, we were one of five awardees out of 1500 applicants nationwide to receive the Micro to Millions award from the Make Mine a Million $ Business, a program provided by the nonprofit organization, Count Me In for Women’s Economic Independence ( Major sponsors of this program include American Express, Fed Ex, Dell, Cisco and Jet Blue. This organization provides business resources, PR opportunities, education, and community support for women entrepreneurs who are growing their businesses. We spent several weeks completing the application process, which also included creating a video. This application process made us re-evaluate the reasons why we work together, our business plan, our business goals, potential business growth, etc. This process was very beneficial and even helped us to create new goals that we had never before considered. 

We recommend to all women business owners to check out Count Me In. They are currently holding the M3 Race, available to all women entrepreneurs ( The Make Mine a Million $ Business RACE (M3 RACE) is a year-long business growth marathon to inspire women entrepreneurs to hit revenue goals and provides resources such as: a personalized business assessment, networking resources, marketing and promotional opportunities, and the chance to win a Grand Prize of $100,000 cash for their business.

What’s next for this mother daughter team?

There are several other divisions to The Lakeside Group that we intend to grow. We are in the process of setting up the Total Life Improvement aspect, which will provide resources to our Clients and Candidates in areas such as health, family, finances, relocation, and others. This will be provided through our website. At the moment, we are looking for other businesses to partner with who have similar philosophies and offer resources or products in these areas that can be featured on our website.

We also entered the Cartier’s Women Initiative Award competition ( If chosen as a finalist, we will go to France to compete to be a Laureate. The prize package for the Laureates includes $20,000, business coaching, international PR opportunities, as well as other great resources. We will find out if we are a finalist this coming June. From there, who knows

Is there anything else you’d like to share?

There are challenges in any business, especially when working with your mother/daughter. However, for us, the rewards far outweigh the negatives and we even have a better relationship because of it. We wouldn’t change a thing!

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This article can be read in the Spring/Summer Issue of WE Magazine for Women