Business of Marketing

On Effective Creative Leadership

March 25, 2018
Joe Pilcavage
Chief Experience Officer

Once upon a time, every agency-minded creative professional aspired to become a creative director — the “visionary” of every pitch or tissue session. They were the elite few often credited for the genius ideas that art directors and copywriters worked tirelessly to help bring to life. Love it or hate it, it’s safe to say those days are long gone.

Roles in the creative industry have since evolved. The silos of yesterday have become a series of blurry concentric circles at best. Power has shifted from the mighty AOR (agency of record) to a rising tide of design-savvy in-house teams, and even more broadly from the brands themselves to the customers they serve. Any number of recent studies will reveal the shocking truth that brands are at the mercy of these folks whether they’re willing to admit it or not. As a result, the expectations of delivering a consistent, persistent, and genuine message has inevitably become the universal standard of design challenges and creative briefs everywhere.

Design studios and creative agencies of all sizes (and more directly, those in a creative leadership or director positions) have been forced to branch out beyond their pre-existing roles and embrace a new way of thinking, doing, and inspiring others. Some have called them business-minded creatives. Google would refer to them as “Smart Creatives.” Whatever vernacular you subscribe to, I’ve come to discover that the ones who are most effectively answering the call of this industry-wide shift are the ones that are living at the center of thinking and making, business and creativity, brands and communities. They’re the ones truly leading the next generation of multidisciplinary creators from the ground floor instead of the proverbial “ivory tower”. Most importantly, they’re weaving an incredible tapestry of design principles that by and large are held together by the same, single connective thread––answering the needs of real people.

Short of becoming a self-taught programmer or getting an MBA to broaden your business acumen, the real point of discussion here lies in what effective creative leadership today looks like in practice — and what creative professionals everywhere can start doing right now to adapt, regardless of their role or tenure. Although I certainly don’t have all of the answers, there are a few key commonalities in the actions, attributes, and activities of those leaders (many of which I’ve had the pleasure of working with) that we can all take inspiration from:

Don’t just direct — do.

Even the most cutting-edge teams can fall prey to the corporate hierarchy mindset of yesterday. The story goes a little something like this: practitioner gets promoted for being some combination of a talented, firefighting rockstar unicorn. They’re instantly expected to take on a new set of responsibilities that may in fact be completely counter to what got them to where they were in the first place; things like managing the emotional and technical growth of others; writing dry, jargon-heavy decks, or worst of all, looking at number-dense spreadsheets and timelines until they’re blue in the face. If that’s your current gig, I’m not saying there’s anything wrong with that. Someone has to do it, and I’d argue that it’s best being someone who can actually empathize with the team who produces the work product, because they’ve been there themselves. But what I am saying is that your job shouldn’t just stop there — nor should it stop at purely delegating and directing others.

Remember that time you got promoted because you were able to come up with killer campaign concepts on the fly, a game-changing insight that nobody else could see, or a fresh UX that netted your client a massive ROI? If that’s been longer than 12 months then this point is probably for you.Like most skills, if you don’t use it, you lose it, let alone continue to learn new ones. We work in an industry where the trends and tools are constantly changing, so not staying on top of your game as a practitioner can be lethal to your career in the long run. If you can’t lead by example, at some point you’re going to render yourself obsolete, even if it’s a slow burn. In the most extreme cases, your junior designers or writers will realistically be able to run circles around you at a fraction of the salary — and if your CFO beats you to that conclusion, it’s game over.

I personally believe that you don’t have to be a manager of people to be a creative lead, although they do often overlap based on the way most teams and projects are structured. But irrespective of how many people you manage yourself directly, if any, taking a player-coach mentality today is key. Not only is it a necessity in many organizations and startups that are running lean by design, but it’s important to remember that you’re the one setting the bar for your team with anything they’ll take on themselves.

Provided you can get past your own ego on this one (and let’s be honest, we all have a bit of ego) there are lot of easy ways to make this happen without sending you too far down the production rabbit hole.

Out of every 10 projects that hits your team, take one on personally and let your work speak for itself. Don’t don’t just opt the to take the sexy one either—in fact, try taking on the shitty one nobody wants. Blow it out of the water and then share your process or rationale with others. Another approach may be doubling down on the initial concepting phases of projects by throwing your hat in the ring too. Remember, your team wants to be inspired and they’re looking up to you for mentorship. And really, if I’m being brutally honest, a reason to keep believing in you beyond your title. What better way than to give them a double dose by showing them what a battle-tested creative mind can do with even the most seemingly boring projects all while teaching them a new trick or two along the way?Other related, actionable bite-size tips to consider:

  • Make time to teach yourself something new. Aim for one thing a week. Read a new book, an article, or try out a new platform or style. What can you quickly prototype or write about that puts your newfound knowledge to the test? dribbble, Medium, and Codepen.io are great for this.
  • Likewise, make the same amount of time to get inspired. The second you stop learning is the second you start falling — out of touch, out of style? Yep, out of favor.
  • Take a generalist mindset to projects and team activities. Being an expert in a singular discipline is important for being an anchor for your team, but the more you seek to understand all of the skills and roles that touch the work your team does, the stronger your leadership and the work product itself will become. Sure, it’ll help you carry your own projects to the finish line faster, but it will also help give clarity around the limitations you may have to work with.
  • Make yourself a shortlist of go-to’s or starting points. Being a creative lead means being able to jump in and out of different head spaces, so having a warp whistle to help you skip right to stage 5 of the process for the same thing you’ve designed or have written a million times is invaluable. This can be as a simple as a folder of icons, some pre-worked up wireframes or deck templates to start from.
  • Everyone should seek mentorship from someone. I mentioned this earlier, but mentorship != (does not equal) management. Everyone should seek mentorship from someone. Find a mentor for yourself. Likewise, as a leader you can and should mentor or at a minimum seek to inspire as many people as possible. Actively find opportunities to share your POV, give feedback, or offer someone a new way to frame the problem they’re trying to solve. And don’t be afraid to show your own scars as a way to help guide others down the right path. Sometimes it’s as simple as just assuming that anyone you’re interacting with has very little understanding of the details. What might seem like second nature to you may completely change the game for someone else.
  • Pause your game and assess the way you play it. Gaming metaphors aside, this can be as simple as taking a couple of minutes out of your day to do a simple SWOT analysis on yourself. Take note of your own strengths and weaknesses and think of how you can use both to your advantage. I promise this will pay dividends for what you decide to do or not to do, and ultimately who you choose to work with or alongside in future projects. Not the most outgoing personality in the a client meeting? Why force it and risk being disingenuous? When you’re focused on trying to compensate for a weakness, you’re inevitably compromising your biggest strengths. In a case like this, a quick look inward might lead you to team up with someone who can electrify a room, letting you be yourself and focus on punching hard with a couple of thoughtful recommendations that show off your experience or deep expertise when it matters most. I personally like to do this as a “3 minute mini-game” nearly every day to make sure I’m constantly giving myself regular feedback or a broader range of options with any work I take on.

Design every interaction.

One of the biggest attributes that separates junior creatives from leads is their ability to “land the plane” with creative exploration (move from divergent to convergent thinking). Sometimes that’s as simple as knowing when good is good enough and putting down the mouse or pencil. This is equally true when it comes to decision making in a lead or director role.

I recently had the pleasure of speaking with Steve Schmidt, Chief Communications Officer of Edelman, at an industry event. While discussing the effectiveness of leadership, he made reference to a powerful decision-making framework that fighter pilots in the air force use known as the “OODA Loop” — Observe. Orient. Decide. Act. Put simply, the speed in which you complete an OODA loop in any situation is directly tied to your effectiveness as a leader or manager. This holds up particularly well for those in creative leadership position, be it on projects or a team. For as much as we always fight the good fight for longer project timelines and bigger budgets, time is always a limiting factor on our creative output. The best creative leads can very quickly gain or give the right amount context of a situation and make an informed judgement call to keep things moving forward. Sometimes that’s as a small as looking at a finished piece and knowing when it “feels” right or will accomplish the business objective, sometimes it means asking the right questions in a review or briefing.

This struck a chord with me as our Founder and Chief Creative Officer Pete Sena always says “indecision is a decision in itself”. In this move fast and ship things world, winning is about making the most informed decisions faster and getting to progress.

Being the lead “creative” in the room doesn’t just stop at your service to a better work product. It also means designing the outcome you want in every interaction or conversation. When you focus your attention operating from that vantage point, instead of thinking tactically about product specs and requirements, you start to wake up the influence you have when it comes to set the pace of a room or navigating people’s minds and actions toward an outcome (a result or feeling), instead of an output (the deliverable). The biggest thing to remember is the only bad decision is no decision.Other related, actionable bite-size tips to consider:

  • Connect the dots. Truth be told, you’ve solved nearly every problem you’ll ever face in your role in some way, shape, or form. Was it in your personal life? Another industry? Your favorite video game? The more you pay attention to the world around you, the more mental models you have to draw from to solve problems quickly. Regardless of the subject matter, people are people.
  • Search for patterns and themes. What words do you hear people say constantly? What colors keep appearing up in your life? What shit keeps showing up in your news feed over and over? Chances are they’re showing up for a reason, and if you’re quick to the punch, you can use that to help inform your ideas, solutions, or actions right now.
  • Be the eyes, ears, and hearts of your audience when solving any creative problem or design challenge. Whether you are asking them yourself or not (and you should as much as possible!) just being empathetic is key to successfully creating something that is truly meaningful for your end user (be it a strategy, a message, or a visual artifact). If you haven’t heard of Design Thinking yet, start here.
  • Demonstrate the behaviors you wish others to model. It might sound trite, but trust me, they will take note. If you’re a hot mess or your feathers are ruffled in a meeting, your team will feel it. Be poised. Have thick skin. But also name your files and clean up after yourself. I’ve learned this one the hard way
  • Ask more questions. Really, don’t be afraid to jump in and ask the hard questions. Understand the why. Understand their thinking, needs, fears, or point of view. The more questions you ask, the quicker you’ll get to the outcome you’re hoping for. This is key for both teammates and customers.
  • Create your own personal philosophy, design principles, or a rule-set for how you approach projects — and don’t be afraid to share that with your team. The more they know about how you work, the more inspiration and influence you’ll imbue in others.
  • Make a habit of collecting and distilling feedback before giving it yourself. People have plenty of thoughts, biases, and opinions. It’s up to you to choose what you accept or politely decline as it pertains to the brief (and the brief should be gospel!). The best leads are able to understand both the big and small picture, and prioritize the actions a team needs to take to keep pushing toward a better product or outcome.

Be in the business of storytelling. Always.

If you’ve had a similar academic experience to mine, the phrase “always show your work” may sound uncomfortably familiar (RIP Calculus…). Although I may have scoffed at teachers in my teenage years for this, in hindsight as a 30-something senior leader in a creative-led organization, I couldn’t be more thankful for that kick in the ass.

It’s no secret that new business is the lifeblood of any organization or creative team. I used to believe that entire process was primarily the job of business developers (at least up until the big pitch), but the reality is that it’s not — it’s the job of everyone. This is especially true of creative leads. Like those high school teachers, the most effective leads are dire advocates of the “always show your work” philosophy. This is likely because they are the ones spearheading everything from how work is presented (the process) to who it’s shown to (the marketing) and why it’s being shown in the first place (the vision). Although there’s tons of complexity that warrants an entirely separate discussion, the key takeaway here is that the strength of a creative lead’s storytelling is directly proportional with the magnitude of the brands and projects they are able to speak on behalf of.

If we take a step back and consider for a second that humans as a species have both survived and thrived on their ability to interact with one another, then it’s not at all surprising to recognize that storytelling has been an integral part of our society for thousands of years —be it around a campfire or over the latest social media platform. Either way, the message is the same; the stories we tell ultimately culminate into an experience we deliver to whoever is willing to give us their attention and listen.

As I alluded to earlier with us entering a new golden age of experience design, experience has become the make or break factor in all things — the choices we make, the brands we choose to engage or re-engage with, and our willingness to share that experience with others. Effective creative leadership in any setting goes well beyond championing the team’s ability to deliver sound data-backed rationale for their decisions, but is a refined discipline focused on the narrative being created every step of the way coupled with a proposition that celebrates why it actually matters. Are you designing a website for a new CPG brand, or are you helping a brand establish a future-proof digital experience that will serve as the new gold standard for digital innovation across their entire product category? I’ve heard the story told both ways, but 10 out of 10 times, the latter always ends up evoking the same response. “Oh wow! How did you do it?” Being able to pay that off with a visually compelling, emotional narrative that lets that person experience your creative process first-hand (the energy, the thinking, the collaboration, and the iteration) is the really the deal maker or the deal breaker.

So what specific actions can we look to from the best to further bolster our storytelling?

  • Capture and document everything. Photos. Videos. Sketches. Notes. Thanks to the ridiculously powerful cameras built right into the phones we lug around in our back pockets, ’s never been easier to get high quality assets that show off the blood, sweat, and pixels that went into the work. Even cutting together a quick behind-the-scenes style reel doesn’t take a deep understand of Adobe After Effects anymore. There’s plenty of cheap, super intuitive programs like iMovie or Lightworks to cut something that looks polished.
  • Give visual scribing a try. Whether you’re mindmapping your own thoughts, taking part in a brainstorm, or leading a client meeting, one of the most effective ways you can align a team around memorable insights, actions, or great ideas is to quickly draw them out on a whiteboard or a poster sheet. Think of it like visual shorthand. Listen for key words or phrases and find ways to quickly illustrate the point. Talking about project goals? Sketch a trophy as you list them out. Want to call out well-stated quote? Write it out in bold letters and draw a big speech bubble around it. Although it sounds pretty obvious, this approach is actually part of a scientifically proven method that aids in recall which perfectly fits in with our agenda as effective storytellers and leads. Warning: Once you start doing this, your notebook will never be the same again
  • Make time to tell it, otherwise you’ll never get to it. As creatives, it’s pretty common for us to move from project to project at lightning speeds. As the creative lead on a project, it’s important to make the time yourself or ensure that time is baked into your team’s process to curate and sculpt the narrative you want to tell when the project ships. I’ve seen many successful ways of doing this––everything  from creating an outline and producing usable assets parallel to completing the work at each phase, to adding an extra chunk of time at the end of a project that’s purely focused on case study creation before you close the books and move onto the next thing.
  • Master the metaphor. The best storytellers are ones that are masters of using metaphors in any conversation. Metaphors are extremely powerful language reframes for turning even the most elaborate thoughts into ideas that anyone can relate to or understand. This is exceptionally handy as a creative lead when you’re trying to quickly communicate an art direction, a specific type of message, or an experience in a way that customers (or your teammates) can easily understand and run with.
  • Make friends with data. As creatives, data can often feel like the sticking point that limits creative freedom – whether it’s in pursuit of measurable results, specific KPIs, or a predetermined ROI that’s driving the engagement. Smart creative leads use the power of data to help shape the story they WANT to tell. If used correctly, data can be used to better frame an initial design challenge or help sell in even the most outlandish concept or ideas. From using social listening tools to navigating Digital Analytics, there’s plenty of great insights ripe for mining to inform your team’s next project. I adamantly believe that it’s constraints that drive creativity.
  • Start with why. I’ll admit it, I’ve always been a huge fan of Simon Sinek’s golden circle model. Partly because I believe that it really is a powerful framework for simplifying how we can effectively interact with others, but also because it fundamentally overlaps with the core principles of everything we do touch as creatives—brands, businesses, and experiences themselves. “Starting with why” as a principle is critical as a creative lead. In practice, that might mean making sure you have a real understanding of the business context behind the work the team is taking on. It might also be gaining a deep understanding of motivations and needs of your audience to help steer the team’s concepting. As a manager, it’s doubly effective in helping you communicate and rally a team around a shared goal or higher purpose. Starting with why in any situation will put you in a pole position to be the filter that your team needs, whether you’re helping unblock them, or helping block for them.
  • Always consider the bigger picture — where does your work fit into the broader ecosystem and who else may it affect? It’s easy to get caught up in the vacuum of a specific brand or the work we do every day. Taking a step back to think about the social, cultural, or economic impact of what we’re doing will not only help you tell a more compelling story, but it will inevitably give you more control over the work itself; what insights you action, what data you ignore, and how you can use timing as an effective tool for shaping your team’s ideas.
  • More deliberate use of imagery. Less exposition. More personality. I can’t mention storytelling without briefly nodding to the the importance of visual strategy  —  something often understated especially when it comes to deck creation and presentations. Creative leads are often responsible for delivering great presentations, and the best ones do it like none other. How? It’s simple. No matter how much we think people track with our most elaborate ideas, our brains are biologically hardwired to process information like it’s still 20,000 BC. Delivering a presentation that sticks means overcoming our limbic brain’s most basic fight or flight mentality on top of its extremely poor attention span. That means you’ve got about a solid 20 minutes to teach, surprise, or delight your audience before they start to lose interest. Like some of the best movies or novels, find a way to craft a visual narrative that has good pacing, a strong tension point you can address, and a way to hammer home your big takeaway with the least amount of words possible. Add in a dash of personality to your VO and an art direction that’s both legible and appropriate for the mood you’re looking to set — and boom, it’s lights out. Every time.

In the spirit of practicing this myself, here’s a the TL;DR (too long, didn’t read) version of everything I’ve outlined above:

Effective Creative Leadership Infographic

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Please include attribution to Digital Surgeons with this graphic.</strong><br /><br /><a  data-cke-saved-href='https://www.digitalsurgeons.com/thoughts/creative/on-effective-creative-leadership/' href='https://www.digitalsurgeons.com/thoughts/creative/on-effective-creative-leadership/'><img  data-cke-saved-src='https://cms.digitalsurgeons.com/wp-content/uploads/2022/01/Protips_Creative_Leadership_JP-scaled.jpg' src='https://cms.digitalsurgeons.com/wp-content/uploads/2022/01/Protips_Creative_Leadership_JP-scaled.jpg' alt='Pro Tips on Effective Creative Leadership' width='800' border='0' /></a></p>

Most importantly, smile and remember to have fun.

Being a creative lead today has never been more fun. You have a chance to wear all kinds of hats; doing, teaching, leading, inspiring, and ultimately creating meaningful experiences that can actually make people’s lives better. Really. When you’re having fun, it shows and that means your team and your customers will have fun too.

Agree? Disagree? I’d love to hear your thoughts!

Thanks for reading.
Joe Pilcavage
Chief Experience Officer
Spread the word!