Inside-Out Leadership
What does it look like when leaders effectively navigate complexity?

By design or happenstance, certain people rise to the top of organizations. In earlier eras when the external context was more stable and predictable, people often got ahead by becoming experts in the norms and cultures of their organization. The people at the top had a lot of institutional knowledge and experience navigating the policies and politics of the system.
So why is there a rising trend of turnover of experienced executives in the C-suite? Companies are replacing CEOs and executives report they are considering leaving their positions due to increasing levels of pressure and burnout in the face of volatility and uncertainty. Expertise in the organizational system no longer seems to give leaders the perspective and capacities they need to guide the organization through complexity. These executives may be titular leaders on the org chart but that doesn’t mean they are equipped to meet this moment as visionaries, strategists and stewards in a time of chaos. They are unprepared when the system they know collapses. That may be why it’s so difficult to spot leaders doing what is required to effectively navigate a changing context.
What does it look like when leaders effectively navigate complexity?
Anyone with a commitment to personal growth via vertical development frameworks likely knows what it feels like to grapple with complexity and wrestle with paradox. This work is not easy – and it’s never done. So if we know what it feels like when we are leaning into complexity on the inside, what does it look like on the outside? How can we spot leaders doing the transformational hard stuff so we can align with them instead of blindly following the leaders just because they show up at the top of the org chart?
Transformational leaders are courageously human.
Before unpacking what it means to be courageously human, it might help to draw a distinction between transformation and innovation. Leaders are often referred to by descriptors that speak to how they deserve the credit for unlocking novel ideas or technological leaps. They are called “innovator” or “entrepreneur” or “visionary” and the qualities of their leadership are shrouded in mysticism. No shade on the inventors out there, but that is not leadership – it’s discovery. In fact, there is a perennial problem in startup culture when it becomes clear that the founder is a great innovator but not a reliable leader.
The common media narrative around C-suite culture is that organizations are switching out executives to bring in people with more strategic or innovative visions. What I think these organizations are actually seeking but don’t know how to name is a transformational leader who can spot the opportunity in chaos, nurture a constructive organizational culture and nudge the organizational system toward better and more enduring impact.
There are certain qualities transformational leaders share that I define as courageous humanity. “Courageous” because it requires admitting vulnerability, ceding control and sitting with the discomfort of paradox and duality. And “humanity” because it centers on connection with others, considering the perspectives of others and relying on others to co-create the transformation you seek.
RESOURCE: Changing on the Job: How Leaders Become Courageous, Wise and Steady in an Anxious World by Jennifer Garvey Berger
Jennifer Garvey Berger recently released the second edition of her seminal book Changing on the Job and goes deep into how to cultivate (and spot) courageous humanity. Jennifer is a scholar of vertical development and a coach who helps leaders expand their capacity to navigate complexity and steward transformational change.
The book guides readers through four forms of mind that make up a developmental map for a world of complexity and change. You can get a short overview in this blog post.
On the question of what it looks like to experience the transformational leadership of another (versus cultivating it in oneself), Changing on the Job provides three key signals to look for:
Courage to hold on and let go: the capacity to set a bold vision and articulate what change needs to happen at every level to get there without needing to take credit for all the change or being committed to any specific outcome on the path to change. Essentially, creating the conditions for others to take action toward a shared vision.
Steadiness with agility: a commitment to staying the course while allowing for nonlinear progress and course corrections – and helping others get comfortable with the nonlinear nature of reality. Paradoxically projecting confidence with flexibility.
Wisdom: the ability to shape the bigger forces that operate beyond personal agency to nudge the system toward a bold vision through thoughtful and sparing interventions that create big impact. Leaning into intuition, noticing and inertia to know when to act and what to say to amplify favorable patterns and dampen undesirable ones on the path to change.
The underlying theme of these signals is paradox and duality. Yet, people crave simple, easy answers. Our instinct is often to align behind the leader with all the answers when we should seek out the leader asking all the questions. Following the guidance in Changing on the Job can help us get better at spotting leaders with the capacity to meet the moment and also get better at meeting the moment ourselves.


