To Be Successful, Don’t Be Afraid To Get Your Boots Muddy

To Be Successful, Don’t Be Afraid To Get Your Boots Muddy

Drew Hiss launched his outsourced payroll and HR technology solutions company, Checkdate Solutions, in 1994.Ultimately Checkdate Solutions became one of Kansas City’s fastest growing companies and was named one of the Greater KC Chamber of Commerce Best Businesses not once, but twice. Additionally, Checkdate Solutions ranked as one of KC’s top 100 fastest growing companies for nine consecutive years and was in the top 25 nationally in its industry. Drew merged Checkdate Solutions with payroll industry leader Paycor, stepping away from the company in 2008 and serving on its board for eight years.

In late 2015, he and good friend Dan Cooper launched Acumen, an organization whose purpose is to create an environment for business leaders and owners to meet with their peers and transparently discuss the issues they face.

Drew and Dan are also the co-authors of a new book.

I had the opportunity to interview Drew recently. Here are the highlights of that interview:

Jill Griffin: Where did you grow up? Describe your early childhood and its significance on your life.

Drew Hiss: I grew up on a small family farm in rural southwestern Kansas. The small family farmhouse I grew up in was the birthplace (literally inside those four walls) of my father and his two brothers. The modest property was homesteaded by my great, great Grandfather.

I am the oldest of four children. My mother was a big city girl from the St. Louis area who met my father in Denver and reluctantly agreed to relocate to rural America to help my dad take over the family farm operation due to my grandfather’s deteriorating health. I grew up in a family-rich environment and at the earliest opportunity, was expected to pitch in and help with the family farm operation. Work was a way of life growing up on the farm, whether helping feed livestock, tilling endless acreage on a John Deere tractor, transporting harvested wheat to the grain elevator or helping service the irrigation system, I was expected to contribute!

I learned about a lot about hard work, values, family, faith and community. Also, because it wasn’t a glamorous or lucrative way of life, I think I learned a great deal about frugality and the importance of stewardship.

Griffin: When did you first get the whisper you belonged in business?

Hiss: Following my graduation from graduate school and obtaining my MBA, I worked for several different firms that varied in size and culture. Small, medium and large. Good culture, mediocre and lousy. Fortune 500 and Main St.

The entrepreneurial bug bit during one of those occupations when I realized how little control I had on my ultimate stature in life and how poorly many companies were led. My frustration and restlessness manifested itself in making the leap, taking a risk and starting a business in 1994.

Griffin: Describe a painful setback in your life and what it taught you.

Hiss: Well, business itself was a setback, especially in the beginning. My early businesses failed but I got back up, dusted myself off, and tried again using the lessons from the first failure to make the second one better.

Here’s what I learned: success comes when you become aware of what you need and that you cannot do it by yourself. You need, among other things, wise counsel, deeper knowledge of your industry (no matter how much you think you know about it) and your competition. You also need good systems and technology. Finally, and perhaps most important of all, you need great people around you. Not just warm bodies but high-quality people and leadership that transforms a “me” centered life in business to a “we” centered organization.

Griffin: As you rose in your career, what obstacles did you encounter and how did you deal with these?

Hiss: As our company grew we ran into all sorts of barriers and growing pains. Funding challenges, technology limitations, budget constraints, and partnerships to name a few. Our key to overcoming these was to create a company that attracted top talent. It may sound tired, but the only way to grow quickly with the least amount of pain is with a strong team that you trust. We may be talking a lot these days about how AI and automation are changing our work landscape but no company grows without a team of high performing leaders.

Personally, I struggled with being an effective father. A company and entrepreneurship demand so much time and energy. With 4 kids, it’s hard to strike a good balance of being a dad/husband/business owner/leader. It wasn’t balanced, so I did the best I could to maintain focus on my faith, my relationship with my wife as first priority in my family, and then intentional time to be with my kids and just focusing on them.

Griffin: What’s a great piece of business or life advice you received, who gave it to you, and how has it enhanced your life?

Hiss: Growing up on a farm there were expectations to work hard and be grateful. My parents helped instill the values of a hearty work ethic and good attitude. It’s amazing how many times I’ve leaned on these two traits to push through barriers and times of challenge. Get back out there and get your boots muddy and do it with a smile.

Griffin: Please give me the top three bullet points in your Personal Leadership Credo.


Purpose: In order to flourish in business and life you need clarity of your purpose. It’s vital. Purpose gives you the framework to understand your values, what’s important (or not), and is the long-term driver to sustain your passion to show up every day.

Grit: This is good old-fashioned persistence, diligence, and never give up.

Prayer: Prayer starts the attitude of gratitude and repositions my perspective of my place in life.

Griffin: What advice do you have for young, talented, ambitious people who want to rise?

Hiss: I got to see Charlie “Tremendous” Jones, a best-selling author and motivational speaker who stated, “the trajectory of your life will most be impacted by the books you read and the people you associate with.” Read great books, which of course in this new world also means great podcasts and other resources that will help provide you with priceless wisdom to accelerate your leadership effectiveness and ability to relate to and lead people.

Secondly, seek community with others who will help provide you with wisdom and counsel. You need some truth-tellers in your life. Ask yourself: Are those that you have around you at this moment the right people to push, pull, and guide you to your desired future? If not, go out and find them. Contributor

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