Failing Forward: A New Take on the Experience of Failure

  • October 13, 2020
  • Ashley Good

Failing Forward: A New Take on the Experience of Failure

In-house counsel need strong legal, compliance and risk management skills—and to develop them, they receive ample training in law school, within their organizations and through other professional development, such as that offered by the CCCA.

However, just like any other professional—and perhaps even more so, given their position of influence—in-house lawyers also need solid soft skills to survive and thrive in the workplace. Skills like resilience, empathy, executive presence, dealing with anxiety, acting and reacting in stressful situations, keeping personal and professional problems separate… The list goes on and on.

Responding to this need expressed by the in-house community, the CCCA partnered with Legal Suite, a leading practice management software provider for legal departments, to provide training on soft skills. The topic: Failure – Getting comfortable with the "F" word.

To get the conversation started on this important topic, award-winning speaker Ashley Good, founder of Fail Forward and presenter of the interactive webinar, shares how failure has helped some of the best leaders in the world.


Wildly successful people, from President Obama to Oprah Winfrey, Richard Branson, Warren Buffet and Michael Jordan, all have incredible stories of failing and learning, which they have courageously shared with the world. While their circumstances may differ, the thread that joins them all is that failure made them better.

The most successful leaders are those who are able to learn and grow from these experiences. Yet, dealing with failure well is not a skill we are ever taught how to do. It is a skill we either learn the hard way, or not at all. 

Considering the importance of this skill to our future success, both personally and professionally, below are five ideas to help us learn and grow stronger from failure.

  1. Start seeing success and failure as two sides of the same coin. There is a tendency to attribute success to our own brilliance and failure to external factors (e.g., other people, luck, timing, environment, market conditions) when, of course, both success and failure are caused by a combination of our own brilliance—or lack thereof—as well as various external factors. Examining both internal and external antecedents opens up the possibility for more learning.

    What is more, the complexity of our work means just about everything we do—whether it be raising a child or delivering a product to our client—will have elements of both success and failure. However, human tendency towards bifurcated thinking has us labeling them as one or the other. Under examination, success and failure start to look a lot alike, so we should, as Rudyard Kipling suggests, “meet with Triumph and Disaster, and treat those two impostors just the same.”
  1. Avoid the error of attributing blame to the first reasonable factor. It is more likely that many interrelated issues are at play. Most failures worth talking about are the result of layers of decisions and actions based on assumptions, beliefs, personalities and more, so when things do not go as planned, it is worth taking a few moments to consider all the reasons why.

    Deepening our understanding of the sequence of events leading to past failure makes it obvious that we had multiple opportunities to stop it—and therefore multiple ways of preventing similar errors in the future. Asking “why?” five times is a popular technique used to think through some of these root causes and is useful as long as the focus is on building our understanding of how we contributed to the failure, instead of finding someone or something to blame.
  1. Take the time to turn individual learning into tangible changes and improvements. Many organizations have processes in place to learn from failures. You may call them after-action reviews, post mortems, retrospectives or something else entirely, but all too often the learning achieved through these processes is not translated outside of the meeting room or pages of the lessons-learned report. The act of investing time in learning is commendable but ultimately useless unless it leads to changes that prevent the error in future.

    Whatever learning process you use should lead to a list of action items that includes timelines and accountability checks. The action items do not have to be set in stone; they should adapt as you learn what works and what does not. The point is to make it easy to translate learning into organizational change. Otherwise, your hard-earned lessons sit on a shelf collecting dust.
  1. Do not fall prey to loss aversion. It is well known we feel the pain of loss more than the satisfaction of gain even when they are quantitatively equal. In an organizational context, that intense pain of loss when we try something that does not work can cause us to pull back, stop taking risks and give excuses to stick with the status quo.

    Protecting our ability to take risks and innovate requires changing how we relate to the experience of failure. Instead of focusing on the loss, we have to frame each failure as an opportunity to accelerate our learning and become better and stronger in the long run. The organizations that are best at reframing start by framing everything they do as experiments where the goal is learning.
  1. Be smart about how you invest time and resources in learning. No one wants to go through an intensive, organization-wide after-action review when the situation is better suited to a quick conversation with a colleague. Conversely, if other people need to understand the failure to avoid making similar mistakes, the learning should not happen behind closed doors. Pick a process that is appropriate for the scale and type of the failure.

The four ideas listed above apply regardless of the scale. This fifth idea simply asks you to consider the causes and the consequence of the failure.

Obviously, a failure caused by incompetence looks very different than a failure caused by experimentation. In the former, learning might focus on an individual’s capacity, while in the latter, it might consider how to evolve the experiment. Similarly, understanding the consequences makes a huge difference in how we deal with a failure and should help us determine how many and which people to involve in the learning process, as well as how to turn that learning into change, and eventually, success.

Ashley Good, founder of Fail Forward, the world’s first failure consultancy, supports people and organizations to acknowledge, create and evolve from failure. A winner of the Harvard Business Review/McKinsey Innovating Innovation Challenge, Fail Forward helps businesses, governments and non-profits harness their failures to learn, innovate and build resilience. Before launching Fail Forward, Ashley worked in Cairo with the United Nations Environment Programme and as a management consultant in Vancouver.