How to Get Creatives to Do Their Best Work

Kathryn HaydonBusiness, Deep Souls, Outlier Thinkers

How to Get Creatives to Do Their Best Work

By Kathryn P. Haydon

Business, Deep Souls, Outlier Thinkers

Have you ever hired someone for their track record of new thinking and fresh ideas, only to find that they didn’t produce the results that you expected?

Was the person to blame, or was it the work culture that got in the way?

Sara’s recent experience provides insights into creating win-win relationships with creatives at work.

Parents and teachers, take note! These ideas also apply directly to kids at home or at school.

Sara’s Story

“Is it not crazy that I still draw upon my pre-adolescent skills to blend in, the ones I perfected so very well in about 4th grade?” my friend Sara* asked me.

(*Sara is not her real name–to protect her boss’s identity.)

Sara, whose teenage motto was Why walk a straight line when a cartwheel will do?, had just left her latest job. An Ivy-league educated writer/editor/communicator, she has several decades of experience working for top publications and international newspapers. With glowing recommendations from past employers, she was hired as a part-time communications director for a small non-profit.

But it didn’t work out.

Sara is a deep soul. She has an enormous capacity to produce high-quality, original work. Her ability to question norms allows her to make new connections and produce fresh content. When she sets herself to a task, she goes deep. She is a change-maker. She doesn’t settle for what is, but imagines new possibilities and creates them.

But the position she was to fill was prescriptive rather than empowering. She was asked to be creative, original, and employ her demonstrated talents but then was micromanaged each step of the way. The organization’s processes dictated that she pre-plan her writing process in workflow charts and check off each stage of the process as it was completed. Her boss did not understand her approach because it didn’t fit within the linear process that she expected.

Sara said, “I felt that I knew and understood where she was coming from but realized she simply didn’t get my approach. She thought I was being defiant while I was just trying to find room to follow the processes that always result in my best work.”

Sara admits that she’s not perfect; there are ways she can improve. Yet her fundamental point is my fundamental point, why I have dedicated my life to making work and school better for people like her.

Sara does not fit in a box and that’s why the world needs her. 

We need her to come up with new ideas, to find new perspectives.

But we can’t expect to have it both ways.

We can’t put people in a box and then expect them to think outside the box. 

We can’t ask deep thinkers to reposition our organizations in new ways and then dictate exactly how they must do this.

We cannot hire someone for their cartwheeling skills and then stick them in a room where there’s only room enough to tiptoe around the edges.

So what does work for deep souls?

Sara’s best work is unleashed when she’s given clear but broad mandates, freedom to get the job done in her own way, and a boss who is tolerant of individual differences.

One of Sara’s early editors provided her a clear directive: Immerse yourself in the city’s schools and report on your findings. He allowed her to follow her own process as long as she got the job done and met her goals.

Sara not only found the stories and turned in more than what was asked, but her reporting broke a major police story, took action that sent one person to prison, ran the superintendent out of town, and resulted in the state overhauling its education laws. When a new editor came in and set up controlling structures, Sara’s work suffered and eventually they parted ways.

In another instance, while director of communications for a school, Sara’s role was to produce an alumni magazine that better served both the school and the alums. She was able to analyze what was needed, survey alumni, and overhaul the alumni magazine, with lasting benefits for all.

Sara told me, “When faced with tight constraints, I fall back on the coping mechanisms I locked down in grade school—lay low, don’t call attention to myself, try to deliver what they want even if it doesn’t make sense. Then ‘they’ turn around and ask why I’m not producing the wonderful, creative work they’ve seen from me before.”

We can’t have it both ways. When we hire creative thinkers, the problem solvers whose mandate it is to bring fresh ideas, organizations and teams must provide a baseline of three things:

  • clear expectations or goals
  • freedom to pursue the goals in accord with one’s own process
  • bosses and colleagues who accept individual work style differences and who understand that putting deep souls in a box will negate the outcomes they expect

If we can simply remember two words we will do better than most: clarity and freedom. Clear goals and the freedom to pursue them is like heaven on earth for deep souls, and the results benefit everyone—if we can just learn to be ok with a non-linear process that may be incomprehensible from the outside.

What do you do to support deep souls in your organization?

Or, as a deep soul yourself, what types of work environments catalyze your best work and deepest motivations?

Are you a deep soul or do you know one? Here are some options if you’d like to dive deeper. 


Kathryn Haydon helps you maximize your creative strengths so you can do your best work. Through keynotes, workshops, and consulting, she trains individuals, leaders, and teams to find the unique spark that leads to deep engagement and productivity.

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