Creative Iteration: Building the Capacity to Try Again
The Power of Creative Iteration
When I stepped into the role of Provost at Lipscomb in September 2022, I quickly learned that one of our community’s boldest goals was to reimagine our general education curriculum. The Impact 360 strategic plan had already cast the vision: build a new liberal arts core that would anchor our students not just in content, but in
character, calling, and capacity to lead.
But how do you build a shared vision for something as foundational, and complex, as a university’s core curriculum?
You definitely don’t do it in one meeting, you don’t do it alone, and you don’t do it with a final answer in hand, ready to launch.
We began with listening. Over that first semester, I held eight open faculty sessions, inviting people from every college, every discipline, to imagine what our graduates should know, be able to do, and become. 179 faculty joined the conversation. And, frankly, that was just the beginning of our work together.
What followed was a three-year, community-wide act of creative iteration.
The Journey Core wasn’t drafted in isolation. Instead, it was formed, shaped, and re-shaped. The next three years were filled with faculty task forces, input groups, feedback sessions, committees working on new courses and degree plans, with every round of ideas bringing new insight. Although sometimes our conversations were tense, we worked hard not to treat feedback as failure, but as fuel for developing our ideas. What emerged from this three year process was a curriculum that was a shared expression of our deepest commitments: to truth, to formation, to the Christian liberal arts. And, it is still forming now that we’ve launched it, with input from both faculty and students as we continue to shape the new courses.
Iteration as a Core Human Skill
In many ways, this long process of designing Journey was an exercise in the very skill we now recognize as essential in the age of AI: creative iteration. While we moved fairly quickly from idea in Fall 2022 to launch in Fall 2025, our focus wasn’t on speed, but was on listening, testing, reflecting, and refining our ideas together. I said throughout the process that our work would be communal and iterative, and it certainly proved to be!
As generative technologies become more prevalent in both education and the workplace, the value of human creativity will be found not in speed of production of ideas, but in how bravely we engage with complexity. Creative iteration is the skill of working through uncertainty, not avoiding uncertainty. It is the ability to hold multiple possibilities in tension and slowly shape something more meaningful than a first draft could ever offer. And in our institutions today, the leaders who will thrive are the ones who know how to stay present in the process of becoming and creating with their team.
Iteration in Action: A Moral Decision-Making Bot
Last week, a faculty member shared a story with me that struck a familiar chord.
In his course on leadership, he had been using the same thoughtful set of articles and lectures to teach moral decision making for many years. He shared a clear framework with students along with relevant case studies. But when it came time for students to respond, he felt that something was missing from their engagement. Their answers were often brief, surface-level, and disconnected from the deeper reasoning the course was designed to foster.
So, he decided to try something new, to iterate on his original plan. He created an AI bot, built around the same moral decision-making framework, and integrated it into the assignment. Students now walk through the same case study, but instead of working alone, they engage with the bot. It asks them guiding questions, challenges their assumptions, and pushes them to articulate their reasoning more fully. He said, “It’s like they have my voice with them whenever they need it, even at 9pm or on the weekend when they sit down to do the work.”
The result? Their responses are deeper, more nuanced, and more connected to both the course material and their own moral compass. And the faculty member is able to better assess their understanding, not just what they remember, but how they think. He talked about how much more the students are learning and the way he is able to see their knowledge more clearly through this new process.
This is a great example of creative iteration at work. The learning objective didn’t change. Instead, the method evolved through experimentation, collaboration with technology, and a willingness on the faculty member’s part to try again. In doing so, the faculty member created a structure that helps students do the same thing, as they work through their own thinking and restate, dig deeper and lay out their arguments.
Designing for Iteration, Not Just Answers
This kind of transformation doesn’t happen by accident. It happens when we design our learning environments not just to deliver content, but to cultivate process. When we cultivate process, we invite students into the messy, non-linear work of thinking again, revising, stretching their imagination, and building resilience.
We all know that too often, education has been structured around right answers and finished products. But if we want to support students who can thrive in a world where AI delivers fast responses, we need to form learners who can slow down, reflect, and improve what’s already been given.
One of my biggest aha moments as I’ve been considering creative iteration is that it doesn’t require flashy tools. Instead, it requires intentional space and permission to try, fail, and refine. And, it requires a shift in thinking about assessment, moving from evaluation as a final judgment to feedback as a formative process.
Of course, most of all, it requires us as educators to model that very process ourselves.
Three Ways to Foster Creative Iteration in Your Curriculum
1. Invite Students into the Process Early
Instead of sharing a polished syllabus or project, consider showing students how it evolved. Where did you iterate? What feedback did you use? Let them see the creative mess, so they know they’re not expected to be perfect either.
Example: Create a syllabus with some openness, allowing students to help you identify some areas of focus that they are interested in exploring that you can then build into the calendar. Or, create an assignment that allows students to choose how they will express their knowledge with a rubric and specific skills or understanding that they must demonstrate, but freedom to choose how they demonstrate those things.
I will say that this kind of openness with process can make some students very uncomfortable. They’ve been raised in an education environment that focuses on producing the “right” answer and a perfect product. The discomfort of learning to linger in the messy part of learning is something you should expect to see and consider how to best support. At the end of this essay, I’ll share a reference to an article I wrote on Free Range Assignments to give you some ideas of how you might approach this.
2. Make Feedback Cyclical, Not Terminal
Restructure assignments to include multiple feedback loops, such as self, peer, instructor, and even AI feedback , so students learn to see revision as essential, not optional.
Example: Begin with students brainstorming or outlining a response to a complex prompt based on prior learning or reflection. Then, invite them to compare their ideas with an AI-generated draft. Ask them to annotate the AI text, highlighting what’s clear, what’s lacking, and what they’d improve. Follow with peer discussion and a final revision that blends their original insight with refined ideas.
This accomplishes a few things:
Centers student thinking and ownership, as the student is starting with their own voice rather than AI’s voice, then they’re comparing and refining their own.
Strengthens critical thinking as they practice evaluation before creation.
Models iteration as a dialogue between human insight, peer input, and tool enhancement.
3. Design for Adaptive Problem-Solving
Give students challenges where the goal isn’t a single solution, but an evolving response that requires ongoing questioning, creativity, and flexibility.
Example: Ask students to build an AI bot based on a fictional or historical character, then adapt the bot’s responses as they explore ethical dilemmas or shifting contexts across a unit. Students can update the bot’s responses as they: Learn more historical or contextual detail, interact with new course content, receive peer or instructor feedback, and reflect on their own ethical frameworks. If you want to use a more traditional method, you could have students respond to an ethical dilemma as a historical figure, and then go back and continue to refine their response as they learn more about that person.
This helps students:
Practice adaptive thinking: They learn that knowledge isn’t static and responses shouldn’t be either. As their understanding deepens, their outputs evolve too.
Navigate complexity with imagination. Students move beyond binary thinking and explore nuance, context, and empathy as they simulate a person’s response across scenarios.
Engage in real-world iteration. The ongoing structure of the assignment models how professionals return to projects, reflect, and revise, rather than aiming for a perfect one-time answer.
Formation That Evolves
Creative iteration is more than a learning strategy, it’s a way of being in the world. It teaches students that growth is rarely linear and that wisdom isn’t formed in one draft. From a leadership viewpoint, it emphasizes that leadership doesn’t come from certainty, but from the courage to return to the work again, and again, and again.
In the age of AI, where information is instant and tools evolve daily, we must resist the pressure to settle for surface answers. Our calling in mission-driven education is to help students go deeper, to build resilience in ambiguity, and to strengthen their creative muscles. I’ve talked often about the importance of formation in the process of leading in the age of AI. Our goal is to form people who know how to use AI efficiently, but who will also lead wisely in this time of complexity and rapid change.
I go back to that family quilt I shared in the essay on Empathy and Ethical Discernment. That quilt has been made across many years by many hands. It has become a symbol of my family’s resilience and commitment to one another because of the way it has been iterated across time and place and people. That is the work of creative iteration.
In order to create learning spaces that encourage and teach creative iteration, we need to design our learning environments with intention, courage, and with formation in mind.
Reflection for Leaders
Where in our programs or institutions do we make space for creative failure and iteration?
Are our systems designed for speed, or do we provide opportunity for depth? Is there time to pause and rethink, to iterate on an idea or solution?
How do we talk about “first drafts” or “pilots,” and what message does that send about learning and growth?
What opportunities do we have to model creative iteration in our own leadership?
References
Fang, B., Shewmaker, J., & Self, S. (2015). Designing Free-range Assignments. In D. Preuveneers (Ed.) Workshop Proceedings of the 11th International Conference on Intelligent Environments, Prague, Czech Republic, July 13-15, 2015 (pp. 120-129). Amsterdam: IOS Press.