Leading from the Middle

The future of creative leadership will be driven by collaboration.

Creative leadership within the brand and design disciplines is fundamentally changing. With more designers working from home on distributed teams, creative leadership and decision-making is evolving to adapt to new paradigms of work. Compounded by global, cultural and social shifts, workplace culture is rapidly shifting to embrace empathy, diversity, and shared accountability, recasting and reframing our preconceived notions around creative power and management. To help chart the trajectory of creative leadership and the future of design and brand teams, I’ve spoken with some of my young design colleagues — creatives on their own paths toward becoming industry leaders themselves.

Leadership is a tricky concept — now more than ever. Through my graphic design education and career, “leadership” has always had opposing light and dark sides. I’ve heard stories and experienced first hand the occasionally harsh, caustic, and mean-spirited qualities of leaders. I’ve never fully understood how personal hubris and selfishness worked in the context of creative leadership, but we’ve all seen how leaders are fallible and imperfect, even when their intentions are good. But every creative leader wears many faces: empathetic catalyst, visionary, mentor, harsh critic, ego-in-the-room, and every shade in between. Much of the history of good versus evil in leadership is the byproduct of this duality, the need to generate revenue through creative work and the pressure of commercially succeeding while also directing teams to push themselves further to create great work.

Like our culture at large, power dynamics within creative professions are fundamentally shifting. Right now, in the midst of the 2020 pandemic, we are confronting cultural, racial, sexual, and societal biases that are deeply ingrained in society. In confronting these, we’re having to deal with the emotional, intellectual, and political realities that fundamentally affect what we do as people, how we view our careers, friends and our creativity. All the while we want to keep our jobs, do good work and stay sane, happy and healthy.

Naively, I always thought the definition of leadership was like a pyramid: leaders at the top, then managers below, followed by directors, designers, etc. Organizationally this may be true, but this is not leadership — it’s just a hierarchy. It helps define roles and responsibilities, but I’ve learned firsthand that leadership is shared by everyone. When we’re all bound together through our collective action, and not the action of just one person, it results in true leadership.

As a graphic designer, I’ve seen how leadership behavior has changed over the last few decades. Like “dressing the room” in a brand meeting, creative leaders would often perform the role of authoritative, aggressive creative voice. The belief was that creative directors should push their teams and be strong and forward in meetings, so they could fight for ideas. This can move projects forward, but when things are taken personally, it creates a culture of friction, fear, and intimidation. As a young designer, I looked up to my creative directors but I also often feared them, which made me doubt my work and worry about saying the wrong thing in meetings.

Emma Barratt, Creative Director and Head of Design at Wolff Olins London, encapsulates the common struggles of creative leadership perfectly in this Creative Capes podcast by Future London Academy

In the podcast, Emma articulates the familial culture of Wolff Olins that she experienced early on, as well as the feelings of intimidation and expectation that came with moving from hungry designer to creative director, where she was tasked with “pushing the boundaries of creativity.” She eloquently explains that there’s “no rulebook to being a great creative leader and no good examples of mentoring.” Even more challenging, Emma explains there’s a double standard in the creative field where female leaders are treated differently than their male equivalents, even when their behaviors and actions are identical. I don’t know Emma, but when I heard her speak about her creative journey in the podcast, I deeply identified with many of her creative challenges. Getting out of “Boss Mode,” eliminating micromanaging, and making room for productive mistakes, as Emma articulates, is really what leadership is all about.

I’ve experienced countless instances of intimidation and friction as a creative. In my early and mid career, being a designer was about struggle, long days, and long nights, because you love the work. It was about passion, fortitude, and the long and hard fight to go from a junior designer to leader and eventual mentor. Effort and personal struggle will always be part of the creative endeavor, but the old behaviors of leadership that foster authority, individual confrontation, and personal friction as the pathway to creative progress must change.

Over the years, the art of business has attempted to understand leadership through different frameworks. The Blake Mouton Managerial Grid is one example that captures many common assumptions and biases. Leadership frameworks are largely an attempt to codify commonly observed behaviors. At the heart of all of these leadership concepts is the attempt to identify interconnection and dependencies in an effort to delegate responsibilities and reinforce results through proactive follow through. All of these efforts ideally transpire in an environment of empathy and civility, so that a goal is achieved without pissing everyone off. These basic ideas apply to anything that requires more than one person and has an achievable goal.

Where businesses often falter is by having an implicit top-down leadership mentality, one that rigidly confines the whole business process. If leaders believe that they are at the “top” and that all they need to do is define a framework and run their processes through it, they’re missing the whole point of leadership. Just because you define the high level terms of engagement and show up to a meeting doesn’t make you a leader. In our remote work world, surrounded by socio-economic turmoil, it feels dishonest and antiquated to rule with an iron fist from the top. This leadership mentality reinforces so many of our cultural bad habits and cognitive biases: Us versus Them, power dynamics, micro aggression, and all the rest. I think of all the leadership horror stories I’ve read in the news, like The Type Directors Club, Refinery29, Ellen, Apple, and so many others that I can’t help but wonder why anyone would want to lead through personal hubris and be so lame and toxic just to be in control. For me, leadership lacks any real substance unless everyone is in the fray on equal footing — you, your team, and your client. I call this “Leading from the Middle” because, as a team, we’re all contributing to leadership. It’s only when we all take equitable responsibility for our combined efforts that the ultimate success of any project is realized.

As a business owner, I prefer accountability as a directional and guiding principal over the idea of leadership. For me, leadership means being a catalyst to start something and getting it off the ground. It’s not about being the singular author or final decider of something. I’m just one voice of many and I know that I don’t have all the answers. It’s not about “tell us what to do,” but “help us figure out how to start.” Accountability, by definition, is your willingness to take responsibility for your actions and your understanding, while accepting the consequences. Accountability produces action and forward momentum. Your willingness to do something and to take responsibility for it — whether developing a design direction, writing an articulate email to a client, or keeping track of a project timeline — all contribute to the collective success of a project. Shared accountability allows for leadership and mentorship to influence and reinforce each other in a virtuous cycle. We’re all co-leaders through our accountability and actions. Full stop.

In the article, The Agile C-Suite, by Darrell Rigby, Sarah Elk, and Steve Berez, in the May-June 2020 issue of Harvard Business Review, they talk about the idea of “the initiative owners” as those who take responsibility, which perfectly characterizes true leadership for me. The article states:

“Some executives believe they know more than they do; some issue orders without having all of the facts. An agile environment has a way of challenging such leaders….Agile, in short, requires humility from leaders. We don’t mean a false humility but rather the sort that accelerates learning and bolsters the confidence of every team member. Humble people recognize the futility of predicting the unpredictable and instead build rapid feedback loops to ensure that initiatives stay on track. They understand that good ideas can come from anyone, not just for those with the highest status. They view their job as helping team members learn and take responsibility, rather than telling every team member what to do and how to do it. An agile leadership team has to adopt such attitudes or its pronouncements will be hollow.”

Running a company is a lot like coordinating a family vacation. We spend a great deal of time planning things out, mapping destinations, goals, and key results, and assembling the needed resources. It’s all in service of the single goal of enjoying ourselves and getting the most out of our time. Once in motion, a vacation always has snags and unplanned impediments: bathroom breaks on the side of the road, a flat tire, a passport stolen out of your dad’s fanny pack (a true story, sadly), food poisoning, you name it. Creative projects, like vacations, always have the best of intentions but, no matter how much you plan, something inevitably goes sideways. This is where “leadership from the middle” truly shines.

“Leading from the middle” gives you the shared knowledge to make informed collaborative decisions when things get weird or challenging. The last thing you want to do when a creative plan shifts is to leave one person out in the cold to solve it for everyone. That never works. When the entire team understands the plan and has a shared investment in the goal, when things get tough, you have a unified answer and a collective power to solve the problem in the right way together.

As brands have become increasingly complex, so has the work of designers. Brand communications now span motion, experience, digital, and beyond. And as a result, creative leaders and teams must become more clear and focused in their communications. I’ve seen creative directors try to “float above the clouds” and focus on the bigger picture, while glossing over the harder, more tangible necessities of brand building. The old adage “a younger designer over designs and under explains, while older designers under design and over explain” still often rings true. With complexity compounded by remote teams, the ability to write and articulate clearly is a business necessity.

Clarity and context are key to selling great design ideas. Every member of the team must be able to provide a strategic explanation backed by tactical answers for every design decision. This is where “leading from the middle” allows each designer to leverage the collective knowledge of the team to learn and refine. Relying only on procedural thinking — where designers are siloed to discrete tasks — loses sight of the larger project dependencies. Everything is interrelated and, in any given creative project, people with only partial knowledge might execute on things, which can turn into a disconnected hot mess. As a designer and leader, I’d rather be a synthesizer of all of the best attributes of a team. It’s the interrelatedness between the work, the team, and the central goal that’s most interesting to me. The reward of true leadership is figuring out how to identify the interdependencies, and then fitting all of the dynamics together to create a great end product for your audience, client, and team.

In episode #194 of Sam Harris’ Making Sense Podcast, Sam talks to Matt Mullenweg of WordPress and Automattic about “The New Future of Work.” WordPress and Automattic are global organizations with a fully distributed workforce, without offices. In the podcast, Matt talks about how he was very inspired by Daniel Pink’s book Drive, and that there are three primary aspects to keeping individuals happy and motivated when everyone is remote: mastery, autonomy, and purpose. Mastery is giving people the tools to be the best they can be at what they do. Autonomy is about giving people the “freedom and agency to control their environment, to work effectively as possible.” And purpose is having “something larger than a paycheck to believe in, that is intrinsically motivating.”

WordPress was started as an open-sourced project with remote online collaboration at the core of building and improving the software. Software development is knowledge work, which has many similarities and differences to creative work, like graphic design or brand building. Historically, creative work has flourished through face-to-face collaboration. This has a lot to do with the materiality of design. Graphic design is often manifested in a physical artifact, such as a poster, record, book, signage, and the like. Today, design and brand expressions must span the physical, digital, and experiential. As a result, the processes Matt outlines for distributed teams are relevant and need to be embraced by designers. Through remote work and distributed teams, designers and technologists have started to share common behaviors and processes. With distributed work, distributed leadership is a necessity to focus on shared accountability and outputs. The work itself — mastery, autonomy, and purpose — drive the individual, while shared accountability fosters collaboration and collective responsibility. It’s this fusion of individual autonomy and mastery, combined with a dedication to a larger creative purpose, that will drive the future of creative work.

Defining the future of creative leadership is about redesigning the cultural and professional defaults in the workplace, so that people can work effectively, share ideas, diffuse bias through shared accountability, and ultimately, have co-ownership of the finished product. To do this, we must redesign the behaviors and mindsets of what “leadership” should look like. We must all work together to “lead from the middle” and build a business culture of continuous individual and collective improvement.

Our old ideas of singular power, pyramid-shaped hierarchies, and the never-ending fight to be creatively heard must be replaced by a shared criticality, self-awareness, objectivity, and a collective momentum toward action. This requires clarity to proactively eliminate creative ambiguity by focusing on the results mapped to creative and business goals. This also requires a more proactive and empathic trust in each other as designers and brand builders, especially as we balance remote work with the eventual return to in-person collaboration.

As we look back at some of the failures of the old leadership paradigms and begin to architect what the future of creative leadership looks like, we can begin to see these larger ideas taking shape. Ultimately, we’re at an exciting inflection point as a society and have an opportunity to define new paradigms of creativity; ones that will help us all make more informed decisions for our teams and clients, while also allowing us to to build new business behaviors that embrace distributed teams, diversified leadership, and more flexible tools to accelerate our creativity, thinking, and collective leadership. Our “New Normal” will inevitably evolve to become our “New Future.”

I would like to thank Athletics’ designers Jaime Patino-Calvo, Ellen Vorheis, and Triana Thompson for helping me craft this article through your thoughts, guidance, and detailed editorial feedback. This article is dedicated to you!


Through the course of writing this article, there are a few items I found really inspirational that did not fit into the flow of this article, so I’m including them here.

API. Assume Positive Intent

In written communications, Matt Mullenweg has appropriated the term API internally at WordPress and Automattic to mean: Assume Positive Intent (API). I love this term. When communicating in written form, it’s hard to gauge tone. If we always “Assume Positive Intent”, then written communications are approached in a better frame of mind.

Idea Meritocracy

Ray Dalio introduced the concept of an Idea Meritocracy, where radical transparency and algorithmic decision-making are leveraged to make better decisions. Creativity is often inherently subjective, but as teams collaborate remotely, we need to move toward a “Creative Meritocracy” where the best ideas win, not the opinion of a singular creative individual.

Rube Goldberg Machine

Creative Leadership requires a delicate balance of procedural and contextual thinking. Procedural thinking is about adhering to a process. As we all know, being able to delegate responsibility requires a good process. However, having a process is not enough. Procedural thinking loses sight of the dependencies that contextual thinking brings to light. When it comes to creative decision making, everything is interrelated and designers are often designing with partial knowledge not seeing how all of the parts need to fit together. Personally, I see creative projects very much like a kind of large Rube Goldberg Machine. Leadership’s job is to keep the machine running smoothly while also looking at the interdependencies of each part of the whole to ensure that all the pieces hold together.

Illustration & animations by Matt Owens

Creative and Project Leader, Partner at Athletics