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How Servant Leaders Can Develop an Entrepreneurial Mindset

October 28, 2021
Servant Teamsmanship
Lisa Oates

In my late 20s, I was getting really good at graphic design. It leveled up my marketing skills, adding to my existing toolbelt of skills that included web development, copywriting, search engine optimization (SEO), and understanding a target audience. At the time, I was working as a Marketing Director for a top real estate team, which gave me the opportunity to “rub shoulders” with people in the community that were business owners and highly-driven entrepreneurs. When they noticed my growing skillset, they asked for help with design, branding, and marketing. And when I continued to get asked, I decided to make it a side hustle. Why not get paid for doing something I love while also helping others succeed?

Starting my own business had its ups and downs. Sure, I was doing the work of offering my services to small business owners, but I was also now the accountant, the human resource manager, the CEO, and the IT specialist. Wearing all the hats of managing a (very strict) budget, getting systems and processes put into place and running smoothly, building a brand, creating a business strategy, and making sure I turn a profit was a lot to handle. It shifted my mindset pretty quickly from a marketer who was good at design to an entrepreneur who was keeping this business running (and growing!).

It was a one-woman show. When problems arose, I had to solve them. When things changed, I had to adapt. I had mentors and friends to support and encourage me, thankfully, but in the end, it was up to me to keep the business afloat. 

An entrepreneurial mindset requires qualities like determination, creativity, curiosity, focus, drive, decisiveness, flexibility, independence, passion, and authenticity.

Shifting my focus from solely marketing to the business as a whole opened up a world of opportunity. Aside from new skills, I was able to organically develop strengths in these entrepreneurial qualities, and that has helped me tremendously in my career journey from individual contributor to organizational leader. Even today, I continue to practice viewing the work as manager, leader, and team member with an entrepreneurial mindset. Then, when I joined WinShape Teams a few years ago, I got to learn more about what it means to be a servant leader, which gave me a new perspective — one that focuses on both results and relationships.

At WinShape Teams, we are passionate about strong, healthy, fulfilled teams and leaders. And we believe that the best leaders are servant leaders. (If you’re not quite sure what a servant leader actually is, download The Servant Leadership eBook that my teammate and friend Joseph Cook wrote earlier this year!)

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Servant Leaders with an Entrepreneurial Mindset

A servant leader typically has qualities like stewardship, foresight, awareness, persuasion, empathy, active listening, a commitment to the growth of others, and building community.

Can servant leaders succeed with an entrepreneurial mindset? Absolutely. In fact, it’s ideal if they can approach their work with that perspective, especially when in a role where they are leading a team.

Imagine a world where the qualities of an entrepreneur merge with the qualities of a servant leader. We would see organizations thrive under the direction of charismatic, driven, compassionate, sharp leaders. A middle manager with both servant leadership and entrepreneurial qualities would care deeply about his/her team and cast a motivating vision to drive performance at every level. Teams would rally around a meaningful purpose, be agile and innovative, and work would get done with excellence!

Servant leaders with an entrepreneurial mindset are mobilizers. They care about their people and their purpose. Their people are fulfilled, and their work gets done efficiently and excellently.

Servant Leaders without an Entrepreneurial Mindset

Not all servant leaders are naturally equipped with the qualities of an entrepreneur. You may be others-focused, empathetic, highly self-aware, and a great listener, but not so great at tackling problems efficiently, looking at challenges from multiple angles, considering new ways of doing things, and innovating to create new product offerings. This can hinder the performance of your team, holding them back from being able to accomplish results more quickly and/or thinking more creatively about how you can better serve your customers.

You’ve probably heard the famous saying, “It’s not personal; it’s business.” As a servant leader, that can be off-putting. After all, we are about results and relationships. But business is personal. People make the business what it is (or isn’t). That’s why WinShape Teams puts so much emphasis on developing people. And when people are growing and thriving, so will the businesses they work for.

It can take a lot of work and intentionality to shift the mindset to a more business-oriented, “fight or die” approach, just like it takes intentionality to become more emotionally intelligent. Don’t shy away from the challenge. To take on an entrepreneurial mindset, you need to have courage and take risks.

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Practical Steps for Servant Leaders to Develop an Entrepreneurial Mindset

If you see yourself as a servant leader looking to develop an entrepreneurial mindset, remember that it requires effort and intentionality. When you start each workday, put on your “CEO” hat, put yourself in your customer’s shoes, and take ownership of the high-leverage tasks. Here are some practical tips to get you started:

1. Tackle challenges differently.

We don’t typically lack ideas, but we do lack follow-through. When problems arise consistently, move past a list of ideas and complaints. Carve out time and space to whiteboard several solutions. (Sometimes I like to set a timer for 10 minutes and do a “brain dump,” writing down everything about that topic that comes to mind. When the 10 minutes is up, I organize those thoughts into buckets to make more sense of it all.) Practice creative thinking techniques. Put yourself in the shoes of your company’s CEO. How can you tangibly propel the organization forward?

2. Thirst for knowledge.

Keep learning, because the business world is constantly changing. As others adapt and innovate, so will the landscape of the marketplace. Some credible sources to explore: Harvard Business Review, Future Today Institute, TED Talks, and IDEO.

3. Fight for your customer.

There is a lot of competition out there, and every consumer has choices. Stand out by obsessing over your customer and their experience with your company. Visit your business or organization as a customer would. Call the main phone number and see who picks up, engaging in conversation with the first line of staff. Visit the website and click around. Is the message clear, concise, and compelling, or are your customers confused about what it is that you offer? If you offer a service, experience that service as a customer. What works well; what needs attention? If you sell a product, purchase the product as a customer would (walk into the brick and mortar shop; purchase online; buy from the vendor). How was that experience? If your customers are leaving unsatisfied, you have work to do to improve the experience. If your customers are getting exceptional service, celebrate that with your team and schedule a rhythm to continue experiencing your business like the customer does.

4. Practice – with a real scenario or a fake one.

Practice is important because it strengthens muscle memory. My husband is a collegiate volleyball coach, and he often says, “Perfect practice makes perfect.” When you practice those repetitions, make sure they are the correct movements, or else you will be creating muscle memory that’s not quite right, causing those micro-adjustments to take you way off course. Practicing with a fake scenario can help you gain experience and learn what works and what doesn’t. (Here’s a fun scenario thinking game to try.) Create a business plan, craft a strategy, reinvent something you do every day.

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Practical Steps for Entrepreneurs to Develop a Servant Leadership Mindset

If you are an entrepreneur, business owner, or highly effective manager, but feel you lack a servant leadership mindset, you’re in the right place! Our purpose is to serve you well with experiences and resources that will equip you to become a better servant leader. Here are a few practical things you can do today to get started:

1. Visit our resource library.

It’s full of helpful articles, eBooks, videos, and tips for those seeking to be servant leaders. If you like, you can subscribe (and set your preferences) so that you don’t miss any of our new resources on topics that interest you.

2. Download The Servant Leadership eBook.

This resource by our Senior Program Instructor, Joseph Cook, will help you understand servant leadership in more depth and is filled with examples of exceptional servant leaders (many with entrepreneurial mindsets).

3. Sign up for a WinShape Teams Summit.

Take advantage of the opportunity to dive deep into servant leadership and immerse yourself in a 3-day event tailored to leaders. Our Summits are packed with learning, activities, group discussions, and networking. (And we build in free time for you to use as you wish… explore our beautiful campus, take a nap, or just relax!) We have programs for those who are new to leadership all the way up to those who lead organizations. View our Summits line-up and register online.

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Develop as a servant leader by attending a Summit.

Held throughout the year at our sequestered campus in Mount Berry, Georgia, our Summits provide you with leadership concepts, guidance, and best practices to help you grow alongside your peers.