Calling All Complexity Leaders!
Positive Deviants Fellowship #1
Dear Friends,
Today we are opening applications for the Positive Deviants Fellowship. It is designed to support transformative leaders who are a) working in situations of high complexity and b) are working on tangible initiatives that hold the potential for positive impact at scale. There are many ways to describe the Fellowship, but it rests on two core ideas:
Complexity is the new normal. A challenge is complex when it involves multiple, interconnected factors that interact in unpredictable ways, making it difficult to address with straightforward or linear approaches. It is qualitatively different than a technical challenge. Whether you are running a global business, rebuilding a community that has been devastated by wildfire, addressing a critical social issue or trying to design an education system to prepare young people for an uncertain future, your work is taking place in context of constant exponential change and high uncertainty. It will be impacted in unpredictable ways by economic, environmental, demographic, and political forces that are not only inter-linked but largely outside your control. New information, technology and social dynamics – along with unanticipated events – will cause your ‘problem’ to evolve and may render previously successful approaches obsolete. There will a diverse range of stakeholders with different interests, perspectives, values, and needs that are likely to conflict or overlap in unexpected ways. Bold moves are likely to carry significant downsides and the cost of failure – along with the cost of doing nothing – will be high. There will be enormous pressure to demonstrate tangible results, even when the best course of action is unclear.
Effective leadership in complex contexts requires a distinct constellation of competencies and capabilities that can be developed and deepened through learning. Over the years, I’ve had the opportunity to learn from and train a diverse array of leaders from across the social, corporate, community and government sectors. I’ve become increasingly curious about the factors that enable people to thrive and exert their influence effectively in very complex, high-stakes settings. My own experience, together with a robust body of research, suggests that there are distinct qualities shared by such leaders.
At the Wolf Willow Institute we sometimes refer to them as competencies and capabilities to reflect both the hardware (skills, tactics & knowledge) and software (mindsets, metaskills & attributes) of complexity leadership. They are not fixed personality traits. Each one can be developed and deepened through learning. But it is hard to find the right kind of learning experiences when you most need them. And some of the most critical factors – things like courage, curiosity or humility – are absent from virtually all post-secondary and professional training. That’s why, together with our partners, we developed the Fellowship.
The following list does two things. It summarizes some of the qualities (not all!) that seem to be shared by effective leaders in complex domains. And in a very practical way, it offers some insight into the qualities we aspire to cultivate during the Fellowship. In no particular order, complexity leaders exhibit:
1. Cognitive Flexibility: the ability to switch perspectives, consider multiple possibilities, and think across traditional boundaries. Cognitive flexibility allows us to process new information, let go of outdated assumptions, and pivot strategies when necessary.
2. Systems Thinking: the ability to see and act from a complex systems perspective. A practical fluency with systems tools, models and principles along with an ability to balance strategy and emergence.
3. Relationality: Relationally savvy leaders are able to work and collaborate respectfully across diverse or polarized social fields. They can ‘sit in the fire’ if necessary, work generatively with conflict and build the trust and psychological safety needed to anchor highly effective team cultures.
4. Curiosity: Complexity leadership is invariably a form of inquiry that is best served by qualities of openness, adaptability, lifelong learning, agility and a certain comfort in not-knowing – all of which are fueled by curiosity.
5. Courage: the willingness to experiment, learn, iterate, take risks and potentially fail. The courage to stand for something, ask destabilizing questions, invite free thought, tolerate dissent, disrupt equilibrium and potentially liberate groups from shallow consensus.
6. Commitment: The tenacity and resolve to keep moving toward desired futures. Commitment to a bigger story allows us to make the difficult decisions and sacrifices change invariably demands.
7. Reflexivity: The capacity for self-awareness in action. Greater reflexivity enables us to understand our internal states, biases, mindsets and patterning and to consciously choose more skillful responses and creative actions.
8. Decisiveness: While leaders in high complexity value input and diverse perspectives, they must also be able to make timely decisions with incomplete information. A high tolerance for ambiguity allows us to make decisions and act even when outcomes are uncertain.
9. Purpose: a deep sense of purpose and meaning enables us to remain personally centered amidst the chaos. At a collective level it offers coherence, alignment, and the ability to focus on shared goals even when the path forward is unclear.
10. Humility: A team’s capacity for learning is strongly correlated with the humility of its leader. Leaders who acknowledge that they don’t have all the answers are far more likely to listen, learn, and adapt effectively in complex environments.
11. Focus: high complexity often requires effective prioritization and a relentless focus on high-impact activities to avoid overwhelm, over-complication, cognitive and emotional overload and endless distraction.
12. Multivalence. The ability to integrate multiple ways of knowing and access optimal states of being. The integration of part & whole. Of knowledge & wisdom. An embodied complexity consciousness.
While competencies can be often learned through a range of relatively conventional strategies – sometimes called informational learning, capacities are developed through a range of experiences and ongoing practices that foster transformative learning. All too often these domains of learning are separate; we learn knowledge and skills in one place, develop ourselves as human beings in another, and work on our innovations, projects and initiatives somewhere else altogether. The whole-person integrated learning container that we aspire to create in the Positive Deviants Fellowship combines all three in ways that are intended to result in new levels of skill, capability and development along with tangible progress in people’s work.
We are resolutely pragmatic, and that means it is also essential to include other ways of knowing - the aesthetic, the imagination, the somatic, the poetic and the wise practices and traditions from within our own cultures - if we are to attend to the whole person. Metaphor, image, and evocative ideas can help us to envision the future and gain a ‘feeling sense’ of territory yet unknown to us. But it also feels critical to ground our approach in sound reasoning and contextualize the Fellowship in a quickly changing leadership landscape.
Over the next three weeks I will endeavor to clarify the practical outcomes the Positive Deviants Fellowship is in service to, and why we feel like this kind of learning is essential in today’s world. It is our hope that leaders and systems shapers of all kinds recognize themselves in this offering and we look forward to reading your applications and nominations!



