Alone we can do so little. Together we can do so much.
— Helen Keller

It's 9:15 a.m. and I'm two cups of black coffee into my Monday morning. I glance at my computer to see two red dots blink slowly awake at the bottom of my screen, each vying for my attention. I choose the one on the left - a first for me. I respond to an ongoing conversation with my designers. Only a few months ago I would have gone straight for my inbox, cringing as I watched the number that used to sit peacefully in the single digits, stretch eagerly into the double.

The story really started last year when I, begrudgingly, acknowledged that my one-woman show was really needing some extra help. So I asked my friend Alli if she would design for me. And then one of the most magical years happened as our dreams grew together. This past January, I switched the studio name to reflect what we had become. Since then, we've grown from a group of three to a team of almost ten. We went from working with 5 brands to nearly 25 simultaneously. The growth of the studio has been the best, and most intense,  unchartered territory I have ever encountered.

Let me start by saying that a team can take a lot of different forms: independent contractors you bring based on the project, virtual assistants and other freelancers, or true payroll employees. However your team looks, it's important to think about how it fits in line with your business and brand values.

If I've learned anything, it's that you don't really know you're going to grow until the moment you grow. It's not always a slow process, sometimes it's the solution to a desperate situation, or it was at least for me. I was losing control over my time and struggling to do everything by myself, while delivering a personal experience for my clients. Along the way, I've learned ten important lessons that I wish I had known last year, and wanted to share with you for the moment you decide to build your dream just a little bit bigger.

Know where you're going.

When my business coach first suggested that I bring on a second designer, I really didn't like the idea. I was convinced that what I REALLY needed was an assistant to answer all of my emails. But I did it anyways, and in the process have landed on a more powerful purpose for my creative studio. I didn’t even realize that this deeper mission existed - but it was there all along, right under the surface: I wanted to support not just the small business owners who became clients, but independent designers that I have met along the way who I admire tremendously.

Here’s why it’s important to know where you are going before you consider growing your team - you will hire the wrong people if you don’t have a clear vision for the future. It took me awhile to learn this and I blindly invested in new team members while I figured it out, and hired for the wrong roles at the wrong times.

Now I know that my goal for growing Drop Cap is to be able to serve more small businesses both internally and externally. We are able to work with more clients as our design capacity increases, we come up with more creative solutions when there is are multiple designers involved in the process, and I also love being able to provide growth opportunities for designers that I personally believe in.

Understand your strengths.

After you’ve thought about where your business is heading and come up with a plan for growing, you need to take some inventory of what you’re bringing to the table. Where do you shine the brightest in your business? What do you do well? Where are your customers or clients seeing the most value from you?

I know that I really enjoy creating a brand's narrative - that unique story that differentiates one creative business from all the others. I've also worked with enough small businesses in this stage of my studio to know what will work and what won't work. I can articulate what I want to see, and I can explain design solutions in a way that makes sense to non-designers. I enjoy organizing ideas, I can easily connect the dots for multi-passionate businesses, I LOVE researching ideas, and my personality is naturally empathetic. I also highly value openness - I love hearing the thoughts and ideas of those around me, which makes me a good fit for working with a creative team and facilitating creative conversations.

If you're new to identifying strengths, I suggest taking at least one personality test (I've taken so many I've lost count!) My favorite is the StrengthFinders test, and there's an accompanying book that will give you further insights into your results. 

Identify your weaknesses.

And while you’re identifying your strengths, go ahead and identify your weaknesses, too.

For me, one of my weaknesses is that I would get really stuck at the beginning and end of a project. It took me a minute to gain inspiration and momentum on a new brand, and then I would burn out towards the end. I love the middle - that's my happy place. Since our design team fully collaborates on every project, I get to step in where I'm most comfortable and challenge ideas, present new ways of solving a challenge, and edit each design down to its most essential parts. I get to bounce ideas off of my team when I reach an obstacle or have a creative block. I had no idea I could love the creative process as much as I do now that I can focus where I am strongest.

I also don’t enjoy designing websites, I really don’t. I know that I’m better-than-average on Squarespace, but it brings me no joy to spend time working on digital layouts. After hating a few web projects (and feeling like it was showing) Alli encouraged me to step away and let someone else run with that service. Since then, I have gotten to collaborate with the most talented web designers I've ever met - and our clients have benefited as a result.

Define your culture.

If you don't define your culture at the beginning, it will define itself. And unfortunately, it could turn in a direction where your team feels undervalued and overworked. Culture can mean a lot of things (like in-studio ping pong tables and fresh cold brew), but since my team works virtually, we have our own way of maintaining unity while working apart. We check in with each other consistently, switch tasks when we feel uninspired and let someone else take a stab at it for a minute. We openly share our honest opinions, and ask for help when we need it. And in order for that space to remain open and safe, I had to take the lead and be vulnerable. As the leader of your team, be bold in your vulnerability. Be trustworthy. Don't make excuses and protect the health and happiness of those who work for, and with, you.

Anticipate growing pains.

This one was hard and sometimes it continues to be difficult. There are still clients who don’t understand why I’m not personally designing the entire project, and I still feel guilt over that some days because I'd gotten so used to being a freelancer. The reality is that I hand pick designers who are better than I am. Real talk - the talent of my design team intimidates and inspires me and makes me feel like a total amateur and I LOVE it! Because in reality, I know that when clients come to Drop Cap thinking they are only working with me and get to work with my team as well, they will have the most incredibly surprising experience and a brand that exceeds their expectations. But as we've grown, I've had to be courageous in explaining why things are shifting and confidently back the talent and qualifications of our designers. I've had to apologize while we figure out the kinks in our new system and something is forgotten. I've had to take on a few extra nights of working late hours to invest in the growth of my business. Sometimes it makes me feel incredibly vulnerable. Sometimes we lose potential clients - but I remind myself that what we are doing is a better way of doing things, and one that I am immensely proud of. We'll get there. 

Prepare to train.

One thing I didn't realize ahead of time and hit me hard was the amount of training it takes to teach someone how to work inside of your business. Because most of us, as independent entrepreneurs, keep a lot of our processes and plans in our head. And unfortunately your team will not be able to read your mind, and may have a different way of doing things. That's why it's so important to start tracking your process. Write out the flow of working with a new client. Start naming files consistently. Be overly patient those first few weeks - not only are you getting used to working with a new person, THEY are getting used to working with YOU. 

Have a support plan.

Personally, I love to work by myself. I get distracted easily. But the culture of our studio is SO important to me, because I want to build a team that feels passionate about where we’re going and why. Initially I didn’t think about things like “check-ins” and expectations. I wanted to wing it. Now, I’ve set up a Slack channel so that my remote team feels like they can get in touch with me at anytime, but also develop relationships with each other, because that stuff is IMPORTANT! This is not a one-woman show. Alli has taught me so much about friendship in the workplace and what it means to really support someone. It means showing up with Chik-fil-A at a mural project and mailing new Rifle Paper notebooks because the schedule has gotten pretty packed. It means showing up not just as a manager, but as a friend. It goes so much further than providing the right resources, it’s providing support and empathy and encouragement. It’s showing up.

Invest in tools.

This is a game changer. Back when I was solo, I tried to be creative with project management systems (and project management was not meant to be creative!!) I would reinvent the wheel all the time. I rework things that are working. I fix things that aren’t broken. But when you start to build a team, you can’t do that. You can’t redefine the structure of your business every 3 months, and honestly I’ve found that to be a good thing. Having multiple people using a system makes it less tempting to change it. Over the holidays we started using Asana and now that we are all in the platform and working collaboratively in a system that is clear and reliable, we’re able to work on so many more projects simultaneously - and this would never have been possible a year ago!

Create templates.

This one wasn’t as hard for me since we do branding and I saw this as something that was important, but I know for those who don’t do brand design (or design in general) it can come as a shock that first time a social media or blog post goes out and it’s NOTHING like what you would have done yourself! It is so, so important to maintain the integrity of your brand - and integrity goes so much further than ethics. Maintain what you’ve built - the look, the tone, the message, the experience. If you have a certain way that you present your product or service, it is important to create standards and templates before you build your team.

Be consistently intentional.

This is by far the most important thing I have learned being a member of other peoples' teams as well as having my own. At the end of the day, people are more important than deadlines or opportunities. Treat your team with respect, generosity, and kindness, just as you would a client. Don't ask for more than you would be willing to give. Don't withhold payment, ignore emails, or forget important dates (like birthdays!!) Ask about them as a person, not just a service provider. Be appreciative of the work they do to grow your business. Stand up for them with clients and support them in maintaining boundaries. Help them to succeed. Be dedicated to improving the lives of every person you encounter - most importantly the lives of your team members. 

Start here

Growing your business is going to mean that at some point you bring other people into the picture. And I hope that you do, because you will be able to accomplish so much more and gain a little white space in your life along the way. When your time comes, I hope you strongly consider these ten lessons as you begin the process.

In the meantime, I've put together a workbook we call the Brand Scratch Pad that will help you to answer deep purpose questions about your business to lay a solid foundation for making decisions as you grow. But you won't have to do it alone. I'll send you a few emails to walk through each section of the workbook and help you identify the heartbeat of your company. I go through this exercise at least once a year to make sure I'm still in alignment. I would love for you to join me! Once you finish the process, you'll get exclusive weekly brand coaching straight to your inbox.

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