4 Simple Steps to Encourage the Entrepreneurial Spirit in Your Team

By Barry Pruitt

I was twelve years old when I graduated from my custom potholder making business to something even more lucrative -- a paper route. Later, I added mowing grass to my ever-increasing revenue stream. My dad had always held a regular job AND he always did something entrepreneurial. It seemed natural to me to start a business; my dad encouraged it. It seemed that you could do anything you wanted if you were willing to conceive it and work hard to achieve it.

To start my lawn business, I used my dad’s mower and later was able to buy tools of my own. I found myself mowing more and more yards in the same neighborhood. It didn’t hurt that I delivered the newspapers (if you’re a Millennial, I mean the printed kind) in the same neighborhood. It became easy to determine when I could provide early service - or offer an extra service like cut the grass or rake the yard (did I mention I expanded my offerings?). I was first to note when the yard looked unkempt and respond with a call to the homeowner offering extra or earlier-than-usual service. This was perceived as great customer service, which encouraged me to continue. Besides, it increased my revenue. 

This lawn and paper route business taught me a lot about the consistency of showing up for work, keeping your word, collecting money, maximizing revenue per customer, determining how much revenue was generated per hour and more. I learned that hard work was necessary, and that smart work could be a winning move, and that you should change – or stop – investing time or effort in anything that wasn’t working. These were great lessons that I would have never learned in school.

Adding to my entrepreneurial education were the experiences of playing basketball in junior and senior high school. I was filled with ideas on discipline, teamwork, fortitude, skill development, trust, and communication. It’s obvious now that sports experiences and starting these micro businesses provided me incredible - and in many cases, life changing - lessons that I now use in coaching clients worldwide.

As a child, I had formed this picture in my mind around the concept of having freedom to choose, to start something from scratch, and confidence in my ability to direct my labor and sweat to a successful end. I knew I had the choice to provide valuable service or product. I believed that you could work hard and stake your personal reputation on the quality of your effort and product and would be compensated accordingly. Couple this idea with the opportunity for customers to vote with their money (pay for service elsewhere), and I learned about going the extra mile. We actually have a core value at Rhythm Systems called “going the second mile.”

The above is background to explain why I grew up believing in the foundation of the entrepreneurial spirit. I believed in dreaming big, thinking outside the box, and doing something great. Having impact. Making a difference. I didn’t call it a BHAG because Jim Collins had not yet named it, but I knew what it meant the first time I heard it. So I wonder why more companies don’t have teams full of people who share the same entrepreneurial spirit.

Times have changed. No more print delivery of newspapers to your front doorstep, not many kids using their Dad’s mower to start a lawn business. Recently, two teenagers in New Jersey were going door-to-door in their neighborhood to advertise their snow-shoveling service. A security conscious resident called the police to report the teens’ suspicious activity. The police came out to investigate, and, despite confirmation that it was just two harmless teenagers trying to earn money, the police forced them to stop. Oops, they didn’t have a permit to shovel snow for a fee.

These two teenagers were sent home for lack of a permit – and I can’t help but wonder if their entrepreneurial spirit was removed in an operation called discouragectomy. I’m confident that you and I could circle round and round the topic of permits and regulation. However, in true Rhythm Systems fashion, I want to focus on outcome.

Like most business leaders and entrepreneurs, I like to keep score. In business, I’ve learned that team members complete and succeed on whatever you put on your scoreboard. Like me, your team will move away from things (or measurements) that create pain and move toward those that are more pleasurable. I wonder if the lesson for these two teenagers was to stay home. Don’t take risk. Don’t think out of the box. Follow the rules. Pain.

As entrepreneurs and leaders in fast growing companies, are you acting like the policy police? Can you afford team members who won't risk and think out of the box?

The two New Jersey teenagers might determine that it’s not worth it to put self at social risk, to think out of the box, or attempt to take charge of their future. Why should they if they only end up with questions from police, accusations, neighbors complaining or the powerful telling them to follow the rules? What about when that happens in the workplace?

Here’s my question for you about leadership behavior – Are you discouraging your “A” players? Have you inserted rules and policies that stifle them from thinking out of the box? Are your team members telling customers, “It’s company policy,” rather than looking for solutions to problems? Are team members, in fact, part of your customer service challenge?

You can bet your team members are molded by life experience just like the two New Jersey teens. It’s a terrible thing to stifle young leaders and entrepreneurs, especially in their formative years. And it's terrible to stifle your “A” players during their formative years on your team. It’s detrimental to financial health when they play it safe. When they learn from experience that it’s safer to say “no” rather than consider how to say “yes,” safer to consider it out of bounds than to think it through. Imagine your loss when team members focus their energy staying off your radar. 

While recently working with our CEO on a project, another team member was urgently seeking information. Patrick’s response was, “Here’s the outcome I need; I trust you to make the decisions to get there.” This was a great example of teach your team to think – not to conform. If you’re hesitant or uncomfortable attempting to do this, then here are four simple steps to get you there.

4 Steps to Teach Your Team to Think

  1. Define the issue: Have team members clearly outline the opportunity or challenge. Any shortcomings Teach_Team_to_Thinkhere indicate opportunity to coach, counsel, and expand thinking.
  2. List Cause or Opportunity: Ask for a list of possible outcomes/risk for opportunities and possible causes for challenges. Again, see any shortcomings in this list as opportunity to coach, counsel, and expand thinking.
  3. List possible steps or solutions: Do not tell, but ask, what are the possible solutions or steps for advantage? This is a brainstorm list and you should be careful not to judge the answers heard. Instead, just capture what’s said and continue asking what other possible solutions there are. Continue this until you feel that their options list is exhausted. If they fall short on this list, consider this one more opportunity to expand their thinking.
  4. Recommendation: Ask, what course of action do they suggest? The tendency for many people here is to refer back to you as leader. Don’t be tempted. Insist that they offer you their best approach based on the data they now have from questions 1-3.

I said four simple steps, not that the steps would be simple to implement. You may feel like this approach will slow you down. Consider that you must (sometimes) slow down in order to speed up. By slowing down to help a team member think and make decisions, later you can move faster with the combination of their effort and yours.

Imagine going through all four steps with one employee five times over the next 2 weeks. How long will it take for them to figure out this pattern? How long before they walk in to your office stating: Here is my opportunity, the list of outcomes and risks, four possible solutions and I think a combination of number 1 and 3 will be best… so, my recommendation is “x”? Thinking like that will allow you to move fast!

Consider the benefit of a team full of creative thinking problem solvers, follow the four steps, create a scoreboard of desired activity, and watch as your “A” players are encouraged to drive your business forward. Bring the entrepreneurial spirit back to life in your business.


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Barry Pruitt


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