Industry Insights

Characteristics of Creative Leadership Style in Business

Posted by StratX on Dec 3, 2019 1:12:58 PM

In this article, we are going to be exploring the characteristics of creative leadership style in business. In order to do this topic justice, I’m going to call upon the expertise of some of the world’s most successful business people. I’ll lean on advertising expert and businessman David Ogilvy, Asana (and Facebook) co-founder Dustin Moskovitz, Reddit’s co-founders Steve Huffman and Alexis Ohanian, and CAPTCHA (as well as Duolingo) founder Luis von Ahn.


Let’s dive right in.

What are some Creative Leadership Characteristics?

To answer this question, I look to David Ogilvy, the father of advertising and a true creative leader with every trick in the book on his sleeve. When asked the exact question above, Ogilvy was able to list these ten characteristics:

1) High standards of personal ethics.

2) Big people, without pettiness.

3) Guts under pressure, resilience in defeat.

4) Brilliant brains--not safe plodders.

5) A capacity for hard work and midnight oil.

6) Charisma--charm and persuasiveness.

7) A streak of unorthodoxy--creative innovators.

8) The courage to make tough decisions.

9) Inspiring enthusiasts--with trust and gusto.

10) A sense of humour.

Whilst we expect things like a capacity for hard work, brilliant brains, and charisma in our most creative leaders, we perhaps understate the importance of a good sense of humour, a lack of pettiness, and a high standard of personal ethics. In fact, personal ethics and modern business often experience a negative correlation.

Want to see what creative leadership traits you’d demonstrate in a business environment? Try one of our simulations.

Key Creative Leadership Activities: How to spot them?

Creative leadership activities involve taking in new perspectives, thinking outside the box, putting yourself in other people’s shoes, and doing your best to understand the varying demands of your teams, services, and products...

Take Asana for example.

Asana is a project management tool and platform (we actually used it to manage this piece of content) with a truly creative approach to company culture. In 2016, co-founder Dustin Moskovitz gave the green light for three nap rooms at their company headquarters. If you work there, you can literally get paid to sleep. That’s just the half of it. Their creative leadership activities involve understanding their workforce and the desire to rest, recharge and de-stress. They also offer daily yoga, free gym memberships, unlimited paid time off, in-house organic cuisine, free mentorship programs, free inoculations, and no meetings on Wednesday (hump day is saved forever!).

Creative Leadership Skills: Are you working on them?

Knowing what creative leadership skills to work on is half of the problem because later you’re going to have to figure out how to actively develop them! Here are some of the things that we think creative leaders do to develop and hone their skills.

Creative leaders will...

  • look for insights from unexpected sources and chance encounters
  • develop wide networks knowing that future value can arise from them
  • open interesting dialogues to explore new perspectives
  • contradict themselves and others to challenge assumptions
  • reject the ordinary
  • see everything as an opportunity to learn or as something that can be improved
  • think in global terms to visualise some major impact
  • think in a responsible and compassionate way
  • practice gratitude, humility, self-awareness, and openness
  • see a path, from idea to opportunity to profitable enterprise, that others can’t

Leadership for Creative Enterprises: How creativity can steer the ship

Creativity can be an overlooked part of a business, or it can be the sails that drive the business forward. Think about Apple, their core ideology is to innovate. Starbucks is investing in digital systems to innovate loyalty behaviour. Hackathons are popping up all over the world to make creativity a competition. Uber is the most creative taxi service ever and it doesn’t even need to make a profit (yet).

This focal point on creativity is attractive to employees. Creative leaders will attract talent to the collective, because processes that embrace learning, improvement, and innovation will captivate exactly the team members who thrive on those ideals. Leadership will acknowledge key values relating to the bigger picture and act on them. They’ll show integrity and honesty and a link between what they say and what they do in order to develop a meaningful company culture. Barriers will soon tumble, big money will no longer be the major incentive, and the tipping point for change will be on the horizon.

The creative leadership style may be one that draws upon anecdotes, experiences, and stories in order to create an empowering relationship with employees and customers alike. They will draw strength from their community when it is needed most, and deliver it back in greater quantities with greater urgency. Boldness will be imperative. Fears and mistakes will be learned from.

Risks will be taken no doubt, but not without a great deal of thought and mitigation as to remain responsible. Creative leaders will master the information at their disposable and use it to drive long-term success through short-term milestones. Resources will be respected, whether natural, human, or manmade.

Importance of Creativity in Leadership

When Reddit launched in 2005, it was like any other brand new platform: memberless and empty. With no traffic to speak of, co-founder Steve Huffman and Alexis Ohanian decided to create fake accounts and start having fake conversations to give the impression of a populated website. The fake accounts allowed them to control the tone of the website and drive the conversation onto topics that they wanted people to explore.

Reddit is now getting more than 1.5 billion hits per month. Their tactic is the same concept behind why we feel more comfortable eating in a busy restaurant than in an empty one. This is just one example of a million that we could have used to demonstrate the importance of creativity in leadership, but it’s a poignant one, we all have to start somewhere.

Managing Complexity with Creativity

If you’re going to approach complex problems, you had better be good at applying creativity to them, because facing them head-on with age-old methodology might only serve to frustrate you. This was not the case for Luis von Ahn, founder of CAPTCHA forms. Luis wondered if the minuscule internet actions done by millions or billions of people could be used for the greater good of humanity.

200 million CAPTCHAs are filled in around the world each day, often when someone joins a website, tries to buy something, or registers for a service, each using up about 10 seconds. Luis realised that these 10 seconds of human brain activity were wasting hundreds of thousands of human years of potential. That’s why CAPTCHA evolved. It started as a random code that you’d need to type into progress. Later, it showed you two words that you must type to prove you’re not a robot. When your actions confirmed these words, you were peer-confirming them to support the biggest book-digitisation project ever in history. The scanning technology for older books where the ink has faded means that computers struggled to recognise the words. CAPTCHA was acquired by Google and went on to help improve images searches and street view technology.

Luis is behind one of humanity’s greatest long-term achievements and it all started when he asked himself this, ‘If we can put a man on the moon with 100,000 people, what can we do with 100 million people?". He thought with a true creative leadership style.


We’ve come a long way in this article towards exploring and giving examples of the characteristics of creative leadership style in business, but there are thousands of further things that are left unsaid. Perhaps the greatest creative business moves are the ones that have not been made yet or are ones that were creatively avoided. We’ll leave that up to you to decide.


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