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How to hire for creative leadership

Entrepreneur Jessica Thiefels, founder and CEO of Jessica Thiefels Consulting, shares three strategies to help you spot exceptional creative leaders in your pool of hiring candidates.

Hiring a creative leader is more than just filtering through a pile of gorgeous resumes and stacks of accolades. To get the most from your hire and ensure your business is poised to grow, you need to look for creativity in other areas. Check out the following strategies that will help you spot visionaries with more than just a pretty portfolio and impressive resume.


Look for talent who: Solves problems creatively

Creative problem-solving is a critical trait for leaders in creative workplaces.

“When I think about the value a creative person can bring to a company, it isn’t necessarily in their ability to come up with creative ideas, but rather in their ability to solve problems in creative ways,”

-Dustin Hodgson, lead designer and co-owner of MyCreativeShop

Creative teams tend to have low emotional stability, according to a study by the BI Norwegian Business School
, which makes for an environment that requires creative problem-solving. The study found that creative employees “have a tendency to experience negative emotions, greater fluctuations in moods and emotional state, failing self-confidence.” Mitigating the potential challenges that come with managing employees like this requires creativity.

When interviewing potential candidates, Hodgson says you can tell if someone is a creative problem solver by asking them to “identify certain challenges they’ve faced and how they overcame [those challenges] differently than others. The tip isn’t so much in the question as it is in listening for a thoughtful answer that stands out from the rest.”

For example, Hodgson explains that he is dyslexic, which has given him the ability to solve problems in creative ways—”not because it’s a gift, but because it forced me to think of creative solutions to hide what some would consider a weakness.” In an interview, this stands out as a unique benefit that a creative leader could bring to a team.

Women Engineering Leadership

Women Engineering Leadership

by Anna Hurley for Asana

This illustration is for an event taking place at Asana today for non-male engineering leaders.

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Look for talent who: Thinks beyond the conventional

People who are among the most equipped to fuel and support innovative thinkers are constant learners who reject the typical ways of thinking, says the team at
. They explain:

“Creative leaders think in contrary directions and deliberately reject conventional, inherited parameters. They are not satisfied with the first solution and search for better concepts that bring major improvement. They view life as a journey where opportunities for learning and development are always present.”

Noticing this trait in an interview can be as simple as asking clear and direct questions about their learning experiences. Consider asking these questions from recruiting agency, Coburg Banks

  • Tell me about a time when you had to think outside the box to complete a task…were you successful?
  • Explain how you would handle a creative challenge where you disagree with the vision.
  • How do you come up with ideas?

Leaders who approach their job with unbridled curiosity and refusal to accept the standard way of thinking tend to be more proactive and dynamic. Look for these characteristics in their responses.

bright ideas 💡

bright ideas 💡

by Anya Perepelkina

this shade of yellow is hands down my favorite color at the moment 💛 this illustration is available on freepik!

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Look for talent who: Values failure

Risk-averse companies will not prevail. In our fast-paced world, companies that are willing to take risks and evolve are the ones who will succeed. This begins with leadership but trickles down to employees—the talent in your company needs to know that it’s okay to fail.

Sara Critchfield
, founding Editor of UpWorthy, explains how their leadership encouraged failure. Just 1 percent of their content received “massive engagement,” followed by 4 percent at “very high engagement,” and 95 percent at “average or low engagement.”

For Upworthy, however, the goal was to make every piece go viral, and Critchfield says, “Many editorial staffers would mope in disappointment when 95 percent of their work fell below our aspirations. With that disappointment would come fear of failing. And fear inhibits creativity. The team started playing it safe.”

Fixing this problem came down to leadership showing how much they valued this “failure,” says Critchfield: “The first thing the team needed to hear me say was, ‘A 95% fail rate means you are doing a great job! No, not just a great job — a fantastic job!’”

Creative leaders need to build an environment where employee innovation is prioritized and failure is the norm. Use questions about previous high-risk decisions and employee innovation to better uncover where they stand with risk-taking in the workplace.

04 - Failure Is Not A Negative

04 - Failure Is Not A Negative

by Britton Stipetic

Rule 04 The Guidebook: Principals for a creative career. My latest medium article. Some principals to enlighten and inspire any creative professional. Link Here -

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Hire creative leaders

Hire the best creative leadership by looking past the resume and portfolio. Use your interview to dig deeper than what is expected and ensure that new hires display the traits critical for anyone in a creative leadership role. If you find someone with a great wrap sheet, interesting creative ideas, and the characteristics that allow for innovation in every area of management, you may have just uncovered your perfect candidate.


Jessica Thiefels is an entrepreneur, founder, and CEO of Jessica Thiefels Consulting. She’s been writing for more than 10 years and has been featured in top publications like Forbes, Fast Company and Entrepreneur. She also writes for Business Insider, Virgin, Glassdoor and more. Follow her on Twitter and connect on LinkedIn.

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