Tess Needham

I’ve led creative teams for many years, and for the last 5 years in a fully distributed environment. I work at WordPress VIP, which is part of Automattic, a company that’s been distributed since its founding in 2005. And with around 1700 employees across 91 countries (as of today!), we’ve got a lot of experience fostering creativity and productivity in a remote setting.

Lead creatives with creativity

When I was expecting my first child, I was so overwhelmed by all the parentin books promising me an instruction manual to be the perfect parent. But as any parent will tell you, there’s no one-size-fits-all approach to parenting.

Similarly, what works for me as a leader may not fit someone else’s situation perfectly. In any case, I hope that sharing what’s worked for me will provide some valuable insights for other creative leaders.

Throughout my career leading writers, designers, and other creatives, I’ve identified eight key “threads” that, when woven together, form the fabric of effective remote creative leadership.

Creativity, defined

But first, I want to acknowledge that “creativity” can be a pretty loaded term. The way I see it, creativity is about filtering the world around you through your unique perspective and skills to produce something new. Creativity is not limited to traditionally “creative” roles — anyone can be creative in how they approach their work.

A common misconception of creative people is that they can slow projects down by demanding that work is grammatically or visually perfect. However, I’ve found that creatives usually just want their work to be meaningful and valued, which is why understanding how to lead them effectively is so crucial.

Creativity is in how the work is made, more than what work is being made.

8 threads of remote creative leadership

Now, let’s dive into these eight “threads” of remote creative leadership.

Since I’m a creative person who can’t hold myself back from a fun idea, I hand-embroidered illustrations for each thread. Since communication tools are such an essential part of remote work, I looked back at long-distance communication technology that is now obsolete.*

Great communication is eesential in both creative work and remote work. In fact, “communication is the oxygen of a distributed company” is part of the Automattic creed. It’s critical to distributed companies specifically, since a lot of our work is done asynchronously.

I interviewed creatives I work with about how they work remotely. About communication, one teammate said:

“Meetings take away from the “flow” of creative work. But a sync with a collaborator can help me feel a personal connection to my output and give me someone to bounce ideas around with.”

It’s essential to balance focused work time with collaborative moments, but that can be difficult when working with colleagues in other time zones, especially as we all have the freedom to set our own schedules.

As a leader, I support good communication by:

• Embracing asynchronous work while knowing when synchronous communication is necessary. I try to treat Zoom calls as rare.
• Encouraging clear, comprehensive written communication. Creatives need to be able to write about their work while it’s in progress, and once completed. At Automattic, every potential new hire goes through a trial process, and we look for great communication skills in these trials. Another example: when sending someone a message, we include context and do research, so we minimise the number of messages we need to send back and forth.
• Fostering personal connections through ice breakers and in-person meetups.
• Using tools like Asana, P2, FigJam, and Google Docs for effective collaboration.

Building camaraderie helps creative team members feel accepted and understood, creating a safe environment for creative risk-taking.

As a colleague said:

“A sense of camaraderie creates a sense of belonging and individuality, which is what creatives want more than anything. To be seen and celebrated as individuals, while contributing to something that could only be created by the whole.”

I foster camaraderie by:

• Leading with curiosity and getting to know team members personally. When I understand who they are and what they love, I can look for opportunities for them to do those things at work.
• Understanding individual work preferences through exercises like “how I roll.”
• Conducting regular, flexible 1-1s that respect time zone differences. We keep notes in a running 1:1 document so we can keep track of conversations and update topics asynchronously.

Connecting creative work to business goals gives team members a sense of purpose and meaning.

A teammate said:

“If I feel like the work I’m doing is important and will significantly impact the business, I find it easier to be more creative.”

I balance creativity with business results by:

• Clearly communicating business goals and expectations, connecting the dots between those goals and the work creatives are doing.
• Collaboratively setting team and individual goals. Teams should estalish clear expectations, priorities, and goals. Roles and responsibilities of each team member should be laid out clearly.
• Regularly checking in on progress and celebrating successes.

Removing blockers allows creatives to focus on their best work.

My colleague said:

“The best thing someone who leads creatives can do is obsess about process and shoulder the parts of the process that their team doesn’t like to do.”

I provide clarity by:

• Ensuring projects are well-scoped and strategically aligned. I proactively connect with other team leads to stay ahead of upcoming requests. Creativity thrives when there are constraints.
• Filtering unnecessary distractions and protecting deadlines. I become a buffer or “bad cop” if needed, protecting my team’s time and focus from outside distractions and requests. And I don’t set the expectation of an immediate response in Slack.
• Connecting team members to relevant people and projects, and to industry topics and trends. I aim to stay in touch with a wide range of happenings inside and outside the organisation. I encourage my team to take time on activities that will fill up their well of creative inspiration.
• Advocating for the value of creative work within the organisation, making sure the work of the creatives on my team is valued.

Building trust is critical for creatives to feel secure and do their best work.

My teammate said:

“Empathy for my talent and skills is essential. If my lead is not creative it’s important that they at least appreciate creativity.”

I foster trust by:

• Encouraging autonomy and brave decision-making. We also look for this in Automattic’s trial process. It’s important that our team members are brave, experiement, make decisions, and be able to move forward autonomously.
• Stepping back from hands-on creative work to empower my team. I need to get out of their way so their creativity can shine. As a creative myself, it’s hard for me to stay out of the weeds of creative tasks, because I find them so interesting. But my job is to unleash the creative potential in others. And when they are empowered to make decisions and shine in their creative work, we can build trust.
• Involving creatives early in projects and valuing their input. They should be seen as valuable collaborative partners that bring value to any project.
• Creating safe spaces for sharing early drafts and ideas, like private Slack channels or brainstorming boards. This allows creatives to get early feedback and input without exposing their work for broader critique too early.
• Encouraging a diverse range of perspectives and ideas, making team members feel valued and heard. I try to be fully present on Zoom meetings and give time to hear all inputs. I also encourage experimentation with productivity.

Effective feedback is essential for creative growth. But when creatives have a reputation for being delicate snowflakes, it can be hard to know exactly when and how to give feedback.

As my colleague said:

“Even though creative feedback is probably the most uncomfortable feedback to get, it can really help you feel more confident in an idea that seems inspiring but may be far-out.”

My approach to feedback includes:

• Being mindful of tone, especially in written communication. I strive for clarity and kindness, and ensure to give feedback on the work, not the person.
• Building review cycles into every project, ensuring there is enough time to incorporate the feedback in the next iteration.
• Viewing leadership as a series of small course corrections over time. Regular check-ins and reviews help here.
• Welcoming and appreciating disagreement from team members. As a lead, what you say can have more weight than you intend.

Making creative work visible and valued within the organisation is crucial.

As my teammate said:

“The best leads put their team in front of themselves to receive praise.”

I advocate for my team by:

• Communicating clear priorities, goals, and success metrics to the rest of the organisation. This is usually via weekly reports and quarterly business reviews.
• Cheerleading my team’s accomplishments, while reporting on progress towards goals. We use Asana and Figma to communicate up-to-date progress, which allows me to check in even when my team is offline.
• Being honest about challenges and areas for improvement.

As leaders, we must remember to take care of ourselves too.

I prioritize self-care by:

• Seeking out coaching and mentorship opportunities to get clarity on career goals and think on a higher level about my contribution.
• Developing skills in “managing up” and advocating for myself.
• Pursuing personal creative projects, or even attaching a creative project to a work one, like embroidered illustrations!

Weaving the threads together

By weaving these threads together, I’ve found a way to maximize team creativity while meeting business goals in a remote environment. My role is to create the conditions in which my team’s creativity can flourish, even remotely and across time zones. Creative people can be sensitive about their work, but also they want to create meaningful and valued work that contributes to business goals.

Many times, creativity is in how the work is made, more than what work is being made. Remember, creative leadership itself requires creativity — there’s no one-size-fits-all solution.

This article is based on a talk I gave at MarketingProfs B2B Forum 2024.

*P.S: I made mini zines featuring a gallery of these embroidered illustrations of obselete long-distance communication technology: