What Strategy can learn from Art – Permission and Courage

I’m an artist, a painter, and I used to be an art teacher. I still paint, and I balance that with a consulting career. I’ve learned some important lessons as a strategist that have come from my passion in art.

I noticed, when talking about art or creativity a lot of people tell me that they aren’t creative, they can’t paint or they can’t draw. I believe I can teach anyone to paint well. I don’t believe the ability to make art comes from some innate and magical talent. Just like strategy, it can be taught.


There’s something incredible about the power of an assignment. A blank canvas can become less intimidating when you’ve been given an object to draw. Throughout my MBA, again and again, every group would come up with alternative and compelling strategies for the various companies that were set out in front of us. As an art teacher, I set up the parameters, and watched my students rise to the challenge. The simple act of creating the opening for a board, executive, or senior leadership team to engage in strategic conversations, to come up with alternative strategic choices, or to make artwork (yes I’ve tested this too), yields great results.

These strategy assignments can take many forms. Imagination sessions, risk scenarios, future thinking, what-if? scenarios, round table discussions with affiliate organisations, customer ethnographic studies, to name a few. Assignments invoke ‘different thinking’ through frameworks, mindset exercises and the simple open invitation to challenge the strategy as it stands. Take the style of one artist and mix it with another. What if Myer and Qantas merged? Facilitated thought experiments can help teams to generate options and drive innovation.


If I write a strategy document, lead a strategy discussion, or participate in just about any other way in business and someone is kind enough to provide a critique – I’m grateful for the learning. Somehow, with art, there’s something much more vulnerable and exposed on the line. Taking on a ‘growth mindset’, or ‘learning mindset’ as it’s often called, seems much more difficult, to me at least.

Either way, the solution is the same. Being willing to take chances matters, and that requires resilience and mental fortitude. In art, it can be as simple as adding a brushstroke of bright colour across a well painted background. In strategy, forging a new path, or suggesting an alternative to the status quo.

Taking chances requires individual courage, and the right culture. Increasingly, boards and executive teams are recognising that to bring new ideas to the table, you need diverse perspectives. Yet, it can be difficult for someone young, or a reflective thinker, or a minority to the group, to have the courage in the moment to share a formative thought – no matter how brilliant it might be.

Permission and courage go hand in hand. We don’t often have to reach as deep to be courageous in a culture where the default answer is yes or how could that work?, instead of no or, we’ve tried that before and failed. Leaders play such an important role in setting the tone, and encouraging everyone to experiment with their thinking and share their ideas.

This also means creating an environment where we have permission to fail, to learn from mistakes. I’ve made a lot more terrible paintings than good ones. I look back on old paintings, and I can imagine if I was discouraged how easy it would have been to give up. Instead, I was encouraged and learned a formal process of critique. Where, instead of hearing that’s not really my taste, my fellow art students would say that could use some darker tones to push it back. Around a leadership table, the discussion as to why something did work, didn’t work, or what we could do to make it work is essential. In strategy, just as with art, bringing together permission and courage creates a learning culture where we can freely create.