Collaborate to Innovate: Embracing Outsourcing

Collaboration has the power to elevate your creative projects. Everyone brings unique skills, expertise, and perspectives to the table. Plus, teaming up with others lets you see your own work in new ways. 

Collaboration can streamline your schedule while strengthening your projects. By outsourcing tasks to qualified experts, you can focus on what you love–and where you add value. You can also ensure the work you deliver is truly best-in-class.

Tiffany Grimes, of Burgeon Design and Editorial, and Julia Kenyon, of Julia Kenyon Design, know this well. The two Squarespace Circle members often join forces, bringing together their respective backgrounds in editorial and design to create stronger, more well-rounded work. 

At Circle Day 2023, the duo teamed up yet again—this time, to lead a conversation about collaborating effectively. During their chat, they shared strategies for finding great collaborators, setting clear expectations, and providing constructive feedback. They also invited members of the Circle community to share their own collaboration best practices.

Find the right collaborators

Good collaboration requires great partners. But to find them, you need to know who you’re looking for. Consider what tasks you’d like to outsource, and which ones you want to keep in-house: where do you drive the most value and have the most fun? One reason Julia loves collaborating with Tiffany is because it keeps Julia in her “zone of genius”—graphic design.

Once you have a sense of your dream team, tap your network. Does someone you know have the skills you need, or do they know someone who does? When you find someone you’d like to work with, ask your connections for an introduction: “Can you introduce me to your friend? I really like their work.” If you don’t have a contact, try reaching out cold: “You’re the kind of person I like to work with. Would you be interested in chatting further?”

After that, ask to hop on the phone or grab a coffee. It’s not enough for the person to look great on paper—you want to verify that you’ll work well together. Chat about your work routines, communication styles, and goals. Decide whether you’d like to move forward. In some cases, you can give the person a trial assignment to assess their skills and strengths before you start officially working together.

Set clear expectations

When it comes to collaboration, clarity is key. Everyone should have a clear understanding of project responsibilities, deliverables, deadlines, and pay. If there’s any disagreement, negotiate before you start working together.

Clearly state your expectations in several places and cement them in a contract*. With everything spelled out in writing, it’s easier to address potential problems, like missed deadlines, necessary revisions, or deliverables that don’t meet your expectations. 

You’ll want to be just as clear with your clients. If you’re collaborating with someone, let them know who you’re working with, what tasks they’re tackling, and why teaming up will lead to better work. You can also define the boundaries of the partnership: if you’re managing the project and have final say in decisions, let your client know. Tiffany likes to feature her collaborators directly on her website, so it’s immediately clear that she works with a team.

*Note: The information in this guide is for informational purposes and should not be relied on for legal advice. We suggest working with an attorney to develop a to-go contract for your team.

Invite and offer feedback

One of the best parts of collaboration is learning from the people you’re working with. So at every stage of the project, invite open communication. 

Ask people to pitch ideas during brainstorms, offer feedback during critiques, and voice questions or concerns as they have them. Inevitably, your team will come up with strategies, tactics, and efficiencies you’ve never thought of. They’ll also see your work with fresh eyes; Tiffany once complimented Julia on how athletic something looked. But because “athletic” wasn’t the look Julia was going for, the two went back to the drawing board to work through the design together.

It’s also essential to provide clear feedback to your team. Let people know what they’re doing right, so they can build on their strengths. Communicate clearly when people miss the mark, so they understand exactly what went wrong and how to fix it. 

Catch problems early by proactively checking in with your team: what challenges are they facing, and how can you help resolve them? Come back to these questions at the end of the project. Your team can provide you with valuable insights that will help you strengthen your work and improve your processes going forward. 

Learn from your mistakes

Don’t get discouraged when things go wrong. It takes time to build a great team, settle into working relationships, and learn the nuances of how everyone likes to communicate.

Start by analyzing what went wrong. Did you find the right person, clarify expectations, and communicate clearly throughout the process? If things didn’t go well with your partner, don’t be afraid to find someone you’re more compatible with. And don’t take it personally. Instead, think about what led you to pick that person, Tiffany says. Are there questions you could ask or processes you could implement to find better collaborators going forward?

Even with the right team, things can go awry. So debrief with your team at the end of a project. Talk about what went right, what went wrong, and what to do differently next time. This could mean making assignments more specific or sending deadline reminders more frequently. It could also mean communicating openly and intentionally as everyone adjusts to working together.

Trial and error is a fundamental part of the process. So instead of seeing these moments as failures, view them as opportunities to learn, grow, and improve. Eventually, your team will be collaborating seamlessly—without really having to think about it.

Collaboration can help you grow your business, create more well-rounded work, and spend more time doing what you love. But at its best, it’s a two-way street. When you find partners who truly complement your strengths, you can elevate each other, making the entire creative process richer and more rewarding.

Special thanks to Julia Kenyon and Tiffany Grimes for sharing their expertise at Circle Day 2023. Visit the Circle blog for more session highlights. 


Want more?

Check out Squarespace Circle, Squarespace’s program for professional designers. Along with exclusive content, discounts, and other perks, Circle brings professionals together from all across the globe to exchange advice while connecting with new clients and collaborators.


Lindsey Lanquist

Lindsey Lanquist is an experienced writer, editor, and content strategist. As a contributing writer for Squarespace (and an amateur web developer), Lindsey enjoys making website building more approachable. She also has a soft spot for all things business and entrepreneurship, and she loves helping people find new ways to grow their businesses.

https://www.linkedin.com/in/lindseylanquist
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