The CEO as Chief…Artist?

By Myste Wylde, Manager, Culturati

Ed. Note: Myste is our most excellent full-time manager of Culturati and we are delighted for you to hear from her directly.


“Creativity is one of the last remaining legal ways of gaining an unfair advantage over the competition.” — Ed McCabe

You may not be Jackson Pollack, but cultivating an artist’s mind could save you in this new world of work.

If it feels like it’s hard out here, that’s because it is. CEOs are increasingly called upon to outperform their usual roles. Vision and empathy are critical as we navigate the hybrid workspace and prepare for the future. Because the Great Resignation has demanded that leaders pay attention or lose, the battle to attract and retain is more fierce than any before. Volatility still reigns geopolitically and within the energy market. New variants are probable, and we have the added challenges of inflation plus labor and supply chain shortages.

Yet both despite and because of this adversity, we are in — dare I say it — an unprecedented time for reinvention and creativity. So how can we unleash creativity when pressed by supply and labor shortages, the battle to attract and retain, inflation, and overall uncertainty? For a start, don’t skimp on the soft skills.

Soft Skills Are the New Hard Skills

“Learn the rules like a pro, so you can break them like an artist.” — Pablo Picasso

In a 17 year study conducted by Raffaella Sadun and Joseph Fuller of Harvard Business School, Stephen Hansen of the Imperial College Business School in London, and Tejas Ramdas of Cornell University, soft skills are ranking higher in importance than traditional financial, technical, and operational functions. The researchers found this to be particularly true in large, multinational corporations where leaders must motivate complex teams across geographic and cultural divides to achieve common goals.

Analysis was based on 4,622 searches from 3,794 executive search firms with 43% focused on CEOs, 36% on CFOs, and the rest on other executive roles. Read more in their working paper: “The Demand for Executive Skills”.

Topping the list of soft skills is communication including active listening, motivation, and clear written and verbal language followed by problem-solving, adaptability, emotional intelligence, innovation, and collaboration. We’ve already seen the trend towards CEO as Chief Communicator, and while many of these attributes can now be measured through predictive science, the art of achieving them is still a vital part of ideation and implementation.

Think Like An Artist

“Creativity can solve almost any problem. The creative act, the defeat of habit by originality, overcomes everything.” — George Lois

Thinking like an artist can help you achieve:

  1. Greater resilience and adaptability
  2. Enhanced empathy to improve relationships and performance
  3. Clarity to define problems and opportunities
  4. New perspectives for problem-solving
  5. Increased creativity for innovation and growth

So how does one get in the mind of Cy Twombly or Agnes Martin?

Step #1: Be Open & Observant

“From 30,000 feet, creating looks like art. From ground level, it’s a to-do list.” — Ben Arment

Artists are keen observers who often catch what others miss. They experience life deeply through a state of attunement, open to each moment as an opportunity for inspiration. Key applications are open-mindedness, open-ended inquiry, and transparency.

We’ve all heard “keep an open mind”, but how do we actually do that? One way is to learn to observe as much as you engage. Instead of moving through your daily routine automatically, consciously see the world around you. Be present and deliberate. Try meditating. Notice how people speak to you and learn to read between the lines.

Another great way to cultivate an open mind is by working on your approachability (which also enhances your collaborative skills). Cultures that encourage employees to share their ideas, concerns, and honest feedback tend to have greater performance, retention, and the ability to attract top talent.

No one knows your company better than your employees and your next billion dollar idea could come from the most surprising of places. One spicy success story we love is that of Frito Lay’s Flaming Hot Cheetos.

During a difficult period, then CEO Roger Enrico rolled out an initiative to “act like an owner” to all 300,000 of his employees. Richard Montañez was a company janitor. He had taken a bag of cheetos home and doctored them with a Latin mix. Because of the open-door policy established, he was able to present this to Enrico, and it became one of the company’s most successful launches ever.

Montañez himself went from a $4 an hour janitor with an incomplete fourth grade education to VP of Multicultural Sales and Community promotions at PepsiCo, with a personal net worth over $20M!

Relentless curiosity and the habit of asking questions is an important part of an artist’s process. In business, the Socratic Method is an excellent way to ask questions that eliminate assumptions. This open-ended inquiry developed by Socrates encourages skepticism (not to be confused with cynicism) challenging preconceptions which often leads to better ways of doing things.

As Will Gompertz defines it in Think Like an Artist, “questions are problems in need of solution”(pg. 103). Problem-solving forces us to think through questions, imagine possibilities, and ultimately conceive new ideas (which is creativity in a nutshell).

There are numerous works on the Socratic Method, developing curiosity through a childlike mind, and mindfulness including the practice of meditation. See also: Simon Sinek’s ubiquitous Start with Why.

Lastly, transparency is a fundamental element of trust and can lead to financial reward as well. Different ideas for increasing this include sharing executive reports on KPIs, financials and sales, recording and sharing executive meetings, inviting all to weekly metrics meetings, the ability to join different department email lists, and so on.

Step #2: Play (Yes, Play)

“The true sign of intelligence is not knowledge, but imagination. Imagination is everything. It is the preview of life’s coming attractions. Creativity is intelligence having fun.” — Albert Einstein

So often in the press of deadlines and duty we don’t allow ourselves the space to toy with ideas that may lead nowhere, but creativity needs to breathe. Painters have what they call “brush mileage” meaning you just have to do it. It can be bad. It can be messy. But the brush needs to bring paint to canvas over and over again until what they’re hoping to express comes out.

Incorporate “playtime” into your brainstorming sessions if you don’t already. Think of the wildest outcome or the most fun and rewarding way to get there, even if in the moment it seems ridiculous or impossible. Giving yourself permission to untether is integral to innovation, and it can stoke or reignite passion for the work (which we all know can become lackluster over time).

“If you want creative workers, give them enough time to play.” — John Cleese

Another part of play is embracing “failure.” Artists don’t fail. They wear down their brushes discarding canvas after canvas until they bring their message to life. Certainly the feeling of failure is real, but aside from the disappointment of expectation, the process of persistence inevitably leads somewhere.

Monet’s paintings were rejected by the Académie des Beaux-Arts’ Salon de Paris for years. The term “impressionism” actually came from a snub by art critic Louis Leroy who derided Monet’s piece as only “an impression” not a finished painting. Now Monet is revered as the revolutionary who transformed French art in the late 19th century.

This isn’t always easy with stakeholders, but remind them of the Thomas Edison quote,

“I have not failed 10,000 times. I have not failed once. I have succeeded in proving 10,000 ways that will not work. When I have eliminated the ways that will not work, I will find the way that will work.”

A company that does this well is Google, and in celebrating their employees’ failures they encourage invention, and in the long run, save time and money as people feel safe to say when something isn’t working.

Step #3: Develop your Perspective (And Constantly Update It)

Artists challenge their own perceptions which help them to develop an intentional perspective. Self-awareness, particularly of our implicit or cognitive biases, is the first step in removing unwanted filters.

All our life we are given cues by family, friends, and colleagues that tell us what to do, think, and feel. This socialization isn’t always negative, but unexamined it can lead to poor judgment and decision making. Analyzing these is also an important factor in developing empathy and connects to openness and observance as well.

In Think Like an Artist, Gompertz explains that our signature is our point of view and that artists think in big picture and small detail. Our experiences will always shade how we process the world. Some artists turn their canvases upside down to shake up thinking. Many of us do this through travel or trying something new.

Pay attention to what feels right, look at it from different angles, from other people’s vantage points, and the refined product becomes a well-thought out perspective that’s unique to you. “It is the artist’s job to pay attention to prompts, to trust their feelings and instincts” (p.150).

Another way to stretch thinking is to engage in Civil Discourse, a topic which NYT’s columnist and author, David Brooks, dove into at our in-person Culturati Summit on April 3 & 4. Economic and political polarization is at a high, but it’s organizationally unhealthy to ban controversial talk in the office. As long as conversations are respectful, which can be established through guidelines, allowing for differences of opinion is a little talked about piece of DEIB.

Step #4: Be Brave

“Vulnerability is the birthplace of innovation, creativity, and change.” — Brené Brown

Artists make a living off of vulnerability. They showcase their scars and shine light on secret fears. As Henri Matisse succinctly put, “Creativity takes courage.” Leaders learn from obstacles and mistakes, and it’s these war stories that peers and employees most want to hear. Sharing your journey and being transparent about your ongoing personal and professional development encourages others to do the same and is a foundational element of transformational leadership.

Calculated risks also prelude success. In his book, The Reinventors, Jason Jennings writes, “A culture of small bets is a learning culture in which people discover the right paths to new destinations (pg. 90).” Jennings recommends following the SMART principle making risk-taking specific, measurable, accountable, resourced, and timed. He also suggests making as many SMART bets as resources allow, financially and with enough time to learn from each outcome.

Step #5: Take the Time

An artist’s most valuable resource is time, and while inspiration can strike on the subway, successful creatives carve out specific time — and guard it ferociously. Pablo Picasso stuck to the same routine practically everyday of his working life: 2 PM start, break for dinner, resume at 10 PM, and work until 4 or 5 AM.

While a busy CEO may not have space on the calendar for a special allocation each day (though we’d make the case for 30 minutes thrice a week), creative exercises can be done in conjunction with other tasks, typically physical. The next time you’re walking the dog or on your Peloton, turn down the volume, literally and figuratively, and give yourself permission to question, ponder, imagine, and conceive ideas.

Another important marker for the artist is the “pause for thought” moment when creator becomes critic. They sit and they look. They search for technical flaws, effect, message, everything they’ve poured into the piece. This critical eye is an abrupt switch from the flowing place of creative freedom from which the art sprang, but it’s this period of review and reflection that often turns a good piece into a great one. It’s the same for solutions born from imagination and inspiration. They must still be checked for efficacy.


“When learning is purposeful, creativity blossoms. When creativity blossoms, thinking emanates. When thinking emanates, knowledge is fully lit. When knowledge is lit, economy flourishes.” — A.P.J. Abdul Kalam

In summation, we believe that cultivating an artist’s mind will separate the most successful companies and CEOs from the rest as we move forward in a new era of culture-building with fresh challenges in a disruptive world.

Vision, empathy, and creativity are all needed to problem-solve and innovate in our new normal of hybrid working environments and the yet to be defined future of work. As we’re all about sharing playbooks at Culturati we’d love to hear how you incorporate these steps in yours.

Thanks for reading!



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