Leading Creative Projects

I was recently working on a project where I asked a designer with about seven years of experience if they were okay with leading the project. They said yes; I said okay; and then I watched the project…not be led. I asked the designer what was happening, and they explained that they didn't feel they were the most creative person on the project, they didn't know what it meant to lead, and they didn't want to appear silly by asking.

Creative leadership isn't about being the most creative person, and while leadership can seem ambiguous, there are some very clear activities that are required to lead a successful creative project. Creative leadership is equal parts pattern forecasting, project management, emotion management, making the first thing, and projecting confidence.

Pattern Forecasting

Systems thinking is a fairly well-defined competency; it's the ability to think about a complex and multifaceted whole, and the relationships between the parts. We're able to practice systems thinking by using diagrams to encourage sensemaking.

Pattern forecasting is the ability to leverage patterns and previous experience to predict how a system may behave, and how people may behave while interacting with it. In the context of designing software, these patterns are not UI patterns but rather structural experience paradigms.

For example, I've worked extensively on designing for higher education, and in nearly every project, I've encountered the paradigm of switching between people and courses. Students are associated with a course, and when a teacher is “doing something” with a student in the project—such as viewing their grades or monitoring their progress—they need to see information about the student and information about the course, and regularly pivot between the two. They also need to see the other courses a student is involved in and pivot between those too; and they need to see the other students in the class as well.

I've never worked on a project for patients and doctors, but I'm very confident that the same structural paradigm exists: navigating around a many-to-many relationship (patients to doctors or medicine to patients), peaking into different contexts, and sometimes needing to move from one to another to perform an action. Even before design begins, I've “lit up” that pattern and am aware I may need to use it. It shapes design decisions that are fairly foundational and time-consuming to explore.

Other patterns include signing up for a service, checking out and paying for something, setting permissions, browsing and searching, and so on. Without creative leadership, designers spend inordinate amounts of time reinventing these wheels; with creative leadership, a team is given permission to simply use the pattern and move on. Creative leadership is about forecasting the need to use these patterns in a system and establishing a base set of utility so that efforts can be spent on the more unique, interesting, and, often, valuable aspects of a product.

Project Management

We often think of a project manager as a role distinct from design or engineering, and it is: Project management has a depth of required skill and specialization. But there's a certain type of project management that lies firmly in the realm of creative leadership. These project management activities include evangelizing for how long ill-structured activities will take, understanding how long to let a team “spin” while they explore, and predicting (and averting) when creative differences might lead to a train wreck.

Design projects have a portion of time allocated to “being creative” and a portion of time for doing more production-style execution work. The former can go on forever, because design solutions are good and bad, but not right or wrong. A large part of the time allocation for design exploration can be viewed as wasted time, but it's fundamental to bringing new ideas to life. Because this type of exploration can go on indefinitely, however, it needs an artificially constrained timebox. Creative leadership is about establishing that exploratory time and constantly working against the inertia of release cycles to treat that time as valuable and mandatory. In practice, this is relentless education and communication of the value of heads-down, no-meeting time and of showing, retrospectively, how creative ideas emerged from “wasted” time.

Creative leadership also means limiting this time in the larger context of work—in knowing how much exploration is really required to suitably come up with a great solution to a problem, and then being the bearer of bad news to the design team in shifting the focus to the more production-style (and often, for designers, less interesting) work that needs to get done.

Project management in the context of creative leadership also means predicting where, in a project plan, a creative train wreck is likely to occur, and building time for it to happen and play out. This means responding to the inevitable scope creep, or recognizing the need for consensus building, or reacting to the “swoop and poop” from executive sponsors who haven't been involved in the creative process but stop in to critique and demand change. I know, with a large degree of accuracy, where these things are going to occur because I've seen them time and time again. I do my best to plan for them; I treat them as somewhat inevitable and make sure that the project timeline accounts for them. Additionally, when I sense one of these experiences looming, I get my team ready and do my best to help them strategize on how to react, both tactically and emotionally.

Emotion Management

The emotional management mentioned above is a constant throughout a creative project. “Being creative” in a company context means presenting yourself, your ideas, and your abilities publicly. Critique is fundamental to advancing an idea. For more-junior designers, that public presentation of ideas for critique usually leads to embarrassment and self-deprecation. That often leads to a combative, defensive attitude: If they don't like what I made, it's because they are dumb or uninformed, not because what I made can be improved. And that often leads to a negative attitude that spreads like a plague.

Somewhat paradoxically, I've found that an effective way to manage that conflict is to acknowledge it exists and that it can be, at times, pretty funny. A marketing creative director who explains in one meeting that they are color-blind but then critiques the colors of an interface in another? A head of product who wants “more pop” and explains that “our steak needs more sizzle”? An engineer who takes the wireframes literally and hard-codes lorem ipsum and placeholder image boxes? All things I've encountered, and all opportunities to lighten an otherwise tense experience. Creative leadership is about providing room for the team to emote, even if the emotions are negative.

Of course, there's a line between acknowledging the way colleagues are behaving (and finding humor in the differences of disciplines), and encouraging an “us vs. them” attitude. I've crossed that line before and it takes a lot to undo the result. Creative leadership is about knowing where that line is and using just enough humor to manage the team's emotions before they begin to fester.

Making the First Thing

Over the 20-something years of my career, I've gotten very good at making something bad, quickly, and throwing it to the wolves. I've found that Making the First Thing serves several purposes in leading a creative effort.

First, it gives the team something to build on, even if that building is a wholesale rejection. It's much, much easier to revise something than start from scratch; consider how Vincent van Gogh saw the beginning of a painting:

Just slap anything on when you see a blank canvas staring you in the face like some imbecile. You don't know how paralyzing that is, that stare of a blank canvas is, which says to the painter, "You can't do a thing".

That's true not just in art and the humanities but also in interaction and visual design. Without a starting point, I've watched a great deal of project time wasted with anxiety and worry. Making the First Thing is putting a mark on a canvas, providing a starting point.

Next, making something bad gives my team an opportunity to poke fun at me. It humanizes a leadership role and gives them permission to see me not just as someone with authority but also as someone who's fallible. Often, it even gives the team a way to be better than me, which—for a junior designer—feels great, and builds a large amount of confidence precisely at a point in the project where confidence is low and self-consciousness high.

Finally, it reminds the team that I am, in fact, a designer and not just a manager. Designers have great respect for people who can make things (and similarly, very little patience for people who can't or won't try). Even in making something bad comes something good: an indication that the person leading the project deserves to be in that leadership role.

Projecting Confidence

The most important part of creative leadership is projecting confidence, all of the time. A creative team needs a rock, someone who is an anchor in a situation that is often without any objective grounding. A project is full of inconsistent critique, spin, changing deadlines, changing priorities, and changing attitudes. A team member needs to know someone is actually in charge and that there is a real likelihood of success.

For a creative leader, that confidence is often faked. I have the same worries as my team, and I see and feel the same churn and ambiguity as they do. But if I can project an attitude of confidence, I can give them the clarity and space to explore, dream, experiment, and produce. This is really where a creative leader earns their salary: I need to absorb the inevitable craziness of creativity, shield the team from worry, and show a consistent face of fearlessness and assurance.

Summary

Leading a creative project takes skill and method, just like any other activity. These skills—seeing the need for using patterns, managing a project and the emotions that come with creativity, making things, and showing confidence—can be taught and learned, ideally through hands-on mentorship. As we work to foster new faces of design leadership, it's on us to make sure these leaders are equipped with the right skills to do the job effectively. That will lead to better project outcomes—and happier, more productive teams.

Works Cited

1. Van Gogh, V. Ever Yours: The Essential Letters. L. Jansen, H. Luijten, and N. Bakker, eds. Yale Univ. Press, 2014.