Some Conditions For Failing Well
If leadership is cultivated in the failures and fumbling then we have to create opportunities for people to fail well.
I recently wrote about three components of DAO leadership: vision, storytelling, and operations. As I’m continuing to pull on this thread I want to explore additional conditions of leadership development and the importance of failing well.
We have to create opportunities for leadership in order to develop it.
Leadership development. It’s kind of an ugly term, evoking images of those high-cheese ‘90s motivational posters. Yet it remains a distinct component of DAO life. DAO leadership development could be summarized as our ability create the conditions for people at scale to pursue novel value-creation frameworks.
Said another way: Leadership development is the development of culture.
Culture emerges out of the practices and rituals within a body of people. It’s the emergent norms and values that shape our coordination. If culture is created through our interactions with each other, it can be changed through our interactions with each other.
I talked about this idea of failing well on a recent episode of the Boys Club pod. (If you don’t subscribe to the Boys Club pod, do it now.) Failing well is a necessary part of leadership development. As people in leadership positions, it’s our charge to both model and create the conditions for failing well in order to develop a culture of failing well within our teams and organizations.
Some conditions for failing well:
Have conviction
Communicate why it matters
Create a plan for execution
Own the consequences, take away lessons
Have Conviction
Conviction is foundational to failing well. It’s the felt experience of your point of view. It’s your operational provocation. Without conviction, it’s challenging to own the consequences and takeaway lessons. You’ll risk losing the trust of your team and — critically — of yourself.
Communicate Why It Matters
Why does your conviction matter? How will you, the work, the organization be changed as a result of pursuing this conviction? Everything in life is sales and failing well is no different. Your conviction has legs only if you’re able to meaningfully communicate it and get people on board.
Create A Plan For Execution
While it’s impossible to anticipate every possible outcome we should have minimum viable plans in place. This sets up the conditions for us to meaningfully retro and pull lessons.
Own The Consequences, Take Away Lessons
Owning consequences is like taking a cold plunge: the most challenging moment is the anticipation right before you jump. IMO this is the best part. That moment of utter existential dread — the unbearable fear of discomfort — is followed by instant mind and body clarification. The experience of owning consequences feels like this. The ability to take away lessons is always immediately worth it.
Practice Failing Well
Following this cold plunge analogy — failing well requires practice. With each plunge, that pre-jump dread becomes less immobilizing. I can’t say that it goes away entirely, but we’re able to exercise choice to the extent to which it dictates our movements.
Take the risk. If we desire for our teams to level up, to take worthwhile risks, we should start by establishing a culture of failing well.