Creative Leaders—Ask Yourself These 4 Questions


by Deborah Holstein, vice president, marketing for Hightail

The best marketing and creative leaders know that their team’s creativity is critical to business success. A recent IBM survey found that creativity is the number-one attribute CEOs look for in new hires, beating out discipline, integrity, intelligence and emotional intelligence.

When your extended team of in-house employees, agencies, vendors and freelancers are able to infuse their creative spirit into your social content, multi-channel campaigns, white papers, email newsletters or even presentation decks for your board, your business wins (and so do you).

This doesn’t apply only to the designers, writers and video producers typically thought of as the “creative team.” Being creative is a fundamental human need and necessary for fulfillment at work, so it also applies even to your channel managers and engagement analysts. The ability to create at work has a very real impact on everyone’s happiness, engagement and feelings of success.

questions for creative leaders

Are you smothering their creativity?

Campaign’s 2016 Industry Morale Survey showed that 47% of agency employee morale is “low” or “dangerously low,” with the top reasons including leadership (73%) and dissatisfaction with the work (38%).

Given the importance of your team’s creativity to achieving your marketing departmental goals and your business goals overall, it’s important to know if you’re allowing your team’s creativity to flow freely.

To find out, simply ask yourself the following four questions:

1. Am I focused on busyness over creativity?

Adobe’s State of Create 2016 survey confirmed that 73% of workers today feel there is increasing pressure on them to be productive versus being creative at work. If your team is predominantly focused on and rewarded for reactivity and putting out fires over thoughtfulness, they aren’t being creative.

Creativity needs space to think, diversity of thought and the ability to engage in experiences that are new and unfamiliar. Of course you have deadlines to meet, but your team also needs opportunities for creativity to breathe. The creative process is not necessarily linear, and inspiration can come from anywhere. Are you supporting your creative team with the time and diversity of input needed to develop new ideas?

2. Am I modeling the wrong behavior?

Do you take regular vacations? Do you email your team late at night and weekends? Are you taking care of yourself—prioritizing sleep, exercise and healthy foods? Are you constantly responding to your inbox instead of carving out the time for creative, strategic thought?

Teams take their cues from the top, and if you’re walking around bleary-eyed with a donut in hand, humbly bragging about your all-nighter in the office, they’ll see where your real priorities lie. Make sure you’re modeling behaviors that promote creativity, so that your team understands that you value it for them too.

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3. Does my team feel unsafe?

Google’s Project Aristotle found that their most innovative and creative teams had one clear thing in common—psychological safety. You don’t need to spend afternoons doing trust, falls but you do need to promote a culture with “the ability to try and fail without recrimination; to be honest in difficult times; to support a spirit of communication and empathy.”

Trust and psychological safety is especially important for agile, fast-moving teams. Mutual respect among team members and knowing that you have their back is critical. If someone takes a chance and fails, you need to show that you have their back and celebrate what you learned instead of letting them take the fall.

4. Am I failing to address their persistent stress?

Have you been tacitly ignoring a persistent pain or problem your team faces again and again? Stress is contagious, and especially in today’s open floor plan work environments, just seeing someone in a bad mood will bring the rest of the team down too.

Take the time to recognize and address a persistent source of stress. It could be creative review and approval issues with external agencies or lack of a system of record where people can access useful assets. Alleviating some of your team’s daily stresses will help free their creativity.

Creative Leaders Act

If you answered yes to one or more of the questions above, you’re not alone. Recognizing how your behavior may be smothering your team’s creativity and making changes for the better is the next step. Free your own creativity and help your team with theirs as well.

Deborah Holstein is the vice president, marketing for Hightail, Inc., the Campbell, CA–based creative collaboration application for marketing and creative teams developing compelling visual creative content and looking to speed the time to market. She can be reached at


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