• Caroline Jennings

How I Built a Team of 7 in 7 Months

Learning to Delegate Tasks and Spend My Time More Wisely



Any time there was a group project in school, I was always the kid who would take charge. If team members weren’t performing to my standards (which were, admittedly, unnecessarily high), I would graciously relieve them of their duties and just get the job done myself.


I didn’t enjoy the extra work, but I did enjoy knowing I was in control of the final product – that under my jurisdiction, our team would create the best Powerpoint deck, Rube Goldberg machine, or pasta skeleton this world had ever seen.


Why the confidence? For one, I knew that I had the determination and perfectionism necessary to create that A+ result. Second, I was a kid, so I had the time to do so.


Time is a luxury you don’t have as an adult, especially as a business owner. There is simply no way you can perform every single task your business requires, at least not without burning out or running your business into the ground (trust me, I’ve been there).


Time is a luxury you don’t have as an adult, especially as a business owner. There is simply no way you can perform every single task your business requires.

That is why it is so important to get comfortable delegating and trusting other people to take the reins – whether that means hiring employees, bringing on interns or contractors, or outsourcing tasks to other businesses.


I decided to hire my first contractor, a designer from Vermont, back in July of 2020. I didn’t have a well-thought-out plan for doing so. I just had way more work than I could handle, and I knew I wouldn’t be able to get it all done without help.

My next contractor, a writer and brand strategist, came on board a month later. Now that I had help, we were cranking out websites faster than ever before. Since I was no longer spending 90% of my time in website “production mode,” I could focus on making sales and growing my business.


By October, we had started getting bigger clients who needed bigger website builds, so I decided to duplicate the designer and writer/brand strategist duo. When my clients started needing more frequent help with website edits and maintenance, I brought on a junior designer who was looking for opportunities to build her web design portfolio (a win-win!).

In seven months time, Word of Web has gone from a one-woman-shop to a team of seven creative professionals (and counting!) who live across the country – Vermont, California, North Carolina, South Carolina, and New York. Now, we are able to help more businesses, deliver websites on shorter timelines, and give our clients the benefit of broad and nationally-distributed industry expertise.

To any new business owners feeling burnt out or inundated with tasks, I encourage you to start delegating, and stop being your own bottleneck. Hiring contractors is a great way to begin because you can pay them on an hourly or percentage basis and loop them into projects on an as-needed basis. (Nowadays, this is particularly advantageous considering the workload fluctuations many of us have experienced throughout the pandemic).


Start delegating, and stop being your own bottleneck.

If you're not sure what positions you should be hiring for, here is a strategy I suggest: create a one-person org chart and outline each and every role you fill. Then, identify which roles you 1) are worst at; 2) like the least; 3) are best at; 4) like the most. I did this exercise back in June (see the screenshot below), and it really helped clarify what roles I should be hiring for and where my time was best spent.



Learning to lean on a team is a big leap – both operationally, financially, and psychologically – but it’s well worth the growing pains. I guarantee that in the long run, it will make a tremendous positive impact on your business, your clients, and your own personal wellbeing.


How has building a team impacted you and your business? Add your thoughts to the comments below.