How I Transitioned From a Solo Entrepreneur to a Team Leader

Digital Marketing


7 min read

Opinions expressed by Entrepreneur contributors are their own.


At age 17, I signed up as a freelance editor on my first freelance platform. From my senior year of high school through most of graduate school, I enjoyed taking various copywriting and editing jobs on these platforms, but dreamed of becoming an entrepreneur. I started a digital-marketing company as a solo entrepreneur and now have a team working with me. The transition from solo entrepreneur to team leader was not easy, but I love working with a team. If you choose the right team members, you will have a talented, well-balanced team and a support system to share the emotional load that so often accompanies managing a business.

Know when to build a team

Entrepreneurs love to think we can do all the work ourselves; however, this can be a disservice to our business ventures. One person can only do so much work without threatening their physical and mental health, work-life balance and overall quality of the completed work. As my digital-marketing company’s clientele increased, I was doing the work of five people while constantly teaching myself new skills. As clients requested work in areas outside my particular area of expertise, I realized I needed a team to keep these clients.

As clients continued requesting more services, I continued to hire other experts. For example, I hired an incredible graphic designer and video scriptwriter to satisfy the needs of several clients. As a result, we would gain more clients requesting similar services for every client whose needs were met by hiring other experts. Thus, clients’ needs guided my hiring strategy, especially to determine when to expand our services and what type of freelancers I needed to focus on hiring. 

Related: Hiring a Freelancer? Here’s What You Should Know

Growing your team

Hiring your staff can be challenging. As I hired my first few freelancers, I quickly realized so many applicants look and sound good on their resumes and in interviews but are not a good fit for the company. In addition, I learned interviews may not always accurately portray the potential new hire, as they may be introverted or nervous during the interview. After this realization, I transitioned away from interviews being the sole determinant of my hiring decision and included a paid test assignment instead. Once they complete their test assignment, I use the quality of their work and their interview to help me decide if they will be a permanent addition to my team.

Another unique hiring method I utilize is hiring three people at the same time. A previous boss of mine taught me this method, and I love how it helps my company. When three people complete their test assignment, you rank their work in first, second, and third. Usually, I would have three articles that were either mediocre, okay or exemplary. I officially hired the candidate who provided me with outstanding work while the candidate who provided me with mediocre work did not receive any further work. I kept the candidate with average work on a list of potential future hires.

Managing your remote team

I currently oversee 28 team members between my digital-marketing company and publishing company. Both are fully remote companies with team members located mostly on the East Coast like myself, but several in countries on different continents. We use project-management software and team-communication platforms, such as Twist, Asana and Trello, for organizational purposes. In addition, we conduct monthly team meetings and have team bonding or icebreaker events.

I learned there is a fine line between micromanaging and being too relaxed as a boss. I learned patience in allowing my team to move a bit more at its own pace while providing reasonable deadlines for projects. We give our copywriters two business days to complete articles and have middle-of-the-month deadlines for social-media editorial calendars. I check in with various team members each day on their progress and answer any questions. 

One management tip I encourage every manager or team leader to employ is showing your team gratitude. Those working with you have a passion for what they do, and they do exemplary work on your company’s behalf. Thank them for their work and remind them why you are grateful for their presence on your team. Recognize them if they go above and beyond on their work. Congratulate them on their successes, whether they are business or personal related. For the 2020 Holiday season, I sent each member of my team a package geared towards relaxing and self-care. 

Related: 7 Mistakes Leaders Make When Managing a Remote Team

Managing team turnover

Team turnover is a natural part of every business. Some team members will reduce their availability because of things like their family schedule, health reasons or schooling. Do not panic if a few team members leave, as this is perfectly normal. 

I recommend business owners examine why team members leave, as you may uncover a potential problem at your company. While team members may leave as a result of something you cannot control, they may leave because of something you can fix. For example, if you have several team members leave and cite your micromanagement or hostility towards other team members as a deciding factor, you can work to fix those. Entrepreneurs cannot solve a problem that they do not know is there.

Resources for uncertain entrepreneurs

Entrepreneurs may not recognize when they need to transition or may lack the confidence to transition. That’s where career coaches or business consultants come in. These professionals can help you move from one step in your entrepreneurial journey to another and help you better run your business.

When I first started my business, I contacted the SBA about consulting with a business mentor. They put me in touch with the Women’s Center for Entrepreneurship. After being successfully mentored, I became a mentor through the organization. Over the past year alone, I have mentored or consulted with over a dozen new business owners and taught workshops to nearly 100. Programs like these are amazing in connecting more seasoned entrepreneurs with newer ones to bring about the most success. I am proud to have experienced being both a mentor and mentee. 

Even successful entrepreneurs can benefit from consultations or learning from other entrepreneurs’ successes and failures. Harvard’s Luca Leonte is a big believer in agile transformation as discussed on Yahoo Finance. I recently adapted some of his strategies, including using webinars for client retention, and became more confident in adapting or changing my initial business goals. Over the past year, these strategies to grow, change and adapt, have been especially helpful. 

One of the best things I ever did for my business was to surround myself with talented, passionate freelancers. Entrepreneurs do not have to run their business alone, and there is never any shame in asking for help. While working with a team may be daunting at first and takes time to get used to, you will be amazed at how wonderful and surprisingly easy it is to work with one, provided you choose the right members. I am forever grateful for those freelancers who decided my digital-marketing company was suitable for them and for all the incredible work we have completed together.

Related: The 5 Best Digital-Marketing Strategies to Empower Your Business

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