Failing Our Way into Possibility

Leadership and failure

In order to really explore and create something new, we need to step out of certainty, try something different, and take some risks.  If we already know exactly how it will all turn out and we can guarantee that, then chances are we are not stretching very far into new territory.


With the complexity and often urgency of the challenges we are facing, with systems changing and in many ways not working, we need to be exploring and building toward something new. As leaders, wherever we are in the system, it is part of our work to innovate, and to support innovation. Our creative ideas, work and willingness to take risks, and our willingness to fail, is needed now more than ever.

The depth of learning we need now comes from both success and failure. In complex systems we need to probe the system and learn, and we learn as much from what doesn't work as we do from what works. Most people are very averse to failure and as leaders in complexity, we need to build our comfort and capacity to fail and learn.

As a leadership coach I see over and over again how deeply our aversion to failing runs and how limiting it can be. In a recent leadership training on failure, participants were noticing how strong their physical and emotional reactions were as we started to really look at personal failure stories, some of which were decades old. It is not enough to just say we are "okay" with failure.

We give a lot of lip service to supporting failure. We refer to the value of  “trial and error” and we talk about 're-framing' our failures or putting a positive spin on them. But in a culture so heavily focused on success and getting things 'right', most of us experience judgement when we fail,  in addition to our own stressful responses. As a result we avoid situations where we might fail or hide our failures, which limits possibilities for the learning and innovation required to work effectively in complexity.


Failing in a failure averse world

As leaders, we are often tasked with 'solving' complex problems,  while also receiving the message directly or indirectly that failing is not okay.

This is not easy territory in our organizations that are highly geared toward controlling outcomes and guaranteeing success. Performance reviews, funding, approval and opportunities are all tightly tied to showing 'success' all the way up the ladder. It takes strong personal leadership and courage to truly support failure.

In a recent large scale change project, where we had anticipated and discussed both failures and successes with the high level leadership, there was significant slow down when the first failure happened. After much discussion we heard: “We understand the need for failure and it is okay... Just don't let it happen again.”   

As leaders (and as human beings in all areas of our lives) a crucial part of the change we are leading is at the level of changing the culture of certainty and success. This takes courage, support and personal practice to navigate.


Personal practice for failure

It is crucial to have a practice to process your own failures in a healthy way and to prepare yourself to fail in the future. What you believe about your failures will either cause you stress, shame and shut down, or it will free you up to learn and move forward. Unprocessed limiting beliefs about failure blocks learning and creative thinking, and eventually will cause us to be risk averse and unable to engage in innovation.

Common patterns that flow from unquestioned (and often unconscious) limiting beliefs about failure include blaming others (or ourselves, or both), withdrawing, giving up, excessive thinking to try to 'figure it out', avoidance of similar situations, numbing, and procrastination.

The chemistry of fear and/or shame impacts our brain function and can actually reduce our learning capacity, our capacity for big picture and creative thinking, and our ability to communicate effectively, all of which we need when we are wanting to innovate together, step up into something new or navigate uncertainty.

“The Work” (inquiry process for personal leadership) gives us a powerful, accessible and effective way to inquire into our own thinking about failure. It also helps us to gain the benefit of our failures, and be able to genuinely learn and move forward. We can use The Work to inquire into our own thinking about failure: our past failures, our reactions to other people's failures, and our underlying concepts about what failure is and what it means to fail.

What does it mean if something doesn't work out how you had hoped? What are your self-critical thoughts? What are your fears? Write them down and use the questions of The Work to inquire, gain awareness of and shift your own limiting patterns and free your thinking back up.


Supporting failure in others - Leading failure

As a leader in complexity, working for change, it is crucial to build your capacity to support others to fail, as much as you support them to succeed. Create a 'safe to fail' environment for your people, so they know they are supported to innovate. Sometimes known as 'top cover', leaders can provide a space for crucial innovative work to happen if they build trusting relationships and good communication with their teams, and clear areas for innovation, risk taking, safe to fail processes, probes and prototyping. It can also be valuable to support a process of harvesting learning from failures.

When things don't turn out the way we wanted them to, there is often a pattern of blame that shows up from leaders, and within systems. Everyone runs for cover. Good work gets stopped in early stages. As leaders of innovation and change, it is crucial to work with your patterns of judgement and fear about other people failing as well as building your own personal capacity for failure. How do you react when someone reporting to you fails?

Great leadership is personal. Leading failure, and failing at leading is very personal. We need to bring regular, compassionate and rigorous practice to our thinking, communication and response to failure if we are going to find our way forward together.

“The Work” is a core practice for personal leadership offered as part of Leadership 2020. For more information go to