How to get Comfortable Letting your Team Fail

In the technology industry, people often refer to failure as a positive thing and encourage teams to ‘Fail Fast’. What does that mean and practically speaking, how do you support the kind of culture that encourages failure where you are accountable for results in your organization?

Why it’s Beneficial to Allow Failure

Innovation happens when people are able to experiment and try new things, including things that might not work. In order to produce groundbreaking ideas, you have to be willing to experiment and think outside the box. Agile supports this notion as well, but mitigates the risk by encouraging incremental low-risk change. When you make small changes, you can easily roll back updates that don’t work. For example, from an engineering perspective, you would do this by trying out a new automation framework with a small number of teams before rolling it out to others. If it’s a failure, you can scrap it and move on, but if it works, you can learn from it and roll it out to others using several more iterations.

As a team leader, when you build this type of culture, not only do employees feel interested and engaged in creating the best solution, they feel safe to try new ideas, even if they don’t pan out in the long run. 

Daniel Pink talks about how the new age of knowledge workers look for autonomy, mastery and a sense of purpose from work and creating a culture of experimentation and learning gives your team all three. 

How do you get Comfortable with the Notion that your Team can Fail?

If you want to develop your team's ability to try new ideas, fail and learn, it's best to create an environment where your team can make mistakes and learn from them with minimal to no impact to customers and other employees. As software engineers, you can do this by experimenting and trying new things in your development and test environments first. Hack-a-thons are a great way to do this as well, allowing teams to experiment with new features and letting judges decide what the company wants to invest in.

If it’s a process or cultural change you are aiming at, you can diminish risk by piloting the change with a small group first and then rolling out the change with a larger group. The willingness to continuously be accountable to results also allows you to tweak, change or cancel programs that are no longer serving their purpose.

In order to create a team culture of innovation stemming from continuous learning and growth, you have to be in the type of organization that values learning from mistakes. Not all organizational cultures are like that, so if you aren’t getting support from your management to create an environment of psychological safety around mistakes, it will not be easy for you to do that for your employees.

If, however, you are in a culture where the highest levels of leadership value innovation and encourage learning from mistakes while also providing air cover for you and your team to try new things, here are some tips to get more comfortable letting your team ‘fail’ so they can learn from it: 

Build Trust by Allowing Small Mistakes first 

Trust is built over time and it’s best to wait until your team has established trust with each other and you before they try cutting-edge ideas. Before you allow your team more and more room to experiment, ensure they are able to succeed at the basic responsibilities of their jobs. Don't give your team the keys to the car before the driving lesson.

Giving team members freedom appropriate to the level they are at and the amount they have proved themselves to you so far as a boss will ensure that experimentation and learning create positive feelings of growth and confidence for your team. Having a negative experience and/or knowing their mistake was detrimental to the business is not going to encourage employees to want to take risks again. 

Finally, allow risks based on seniority and experience. More experienced team members can exercise better judgment as to the gravity of the risk and thus can usually be given more freedom to decide how, when and where to innovate.

Create Cover from Upper Management for your Team 

In cultures where mistakes and learning aren’t celebrated, there is no way to easily create this on your team because your team will have fear that their ‘mistakes’ may be discovered by other teams and higher levels of management. Before you try to be more innovative on your team, ensure your boss is onboard and sees the value in this type of culture. If your boss not only supports you, but also wants to celebrate learning from mistakes, you are in good shape to learn. Either way, it's generally a good idea to keep learning and mistakes made within the team unless you feel sharing would provide beneficial lessons for others in the company.

Build a Resilient Organization that can Bounce Back from Mistakes Quickly

When a company is first starting out, you don’t have much to lose and experimenting is a natural part of success. As a company grows and has established ways of making money and running their business, it’s usually more risk averse. This is natural and if you want to keep the culture of experimentation alive, you should build resiliency into your organization. For technology teams, one of the most common ways to do this is through building a robust automation framework. When the framework is built to catch bugs and issues quickly, a team will know right away if there are problems with any updates they made and they can fix it promptly.

For non-technical organizations, resilience is built through creating an agile structure that can pivot swiftly and that has a foundation of healthy teams that can quickly solve problems.

Mitigate Risk

In order to make a culture of continuous learning really work for an organization, know what areas are ok to fail in and what are not. If you are running a business, creating an outage that will negatively impact customers for hours is simply not acceptable. Testing out a new automation technology in a test environment over the weekend with minimal disruption is highly acceptable. It’s crucial to create guardrails for your team so they know the boundaries by which it’s ok to make mistakes. Generally, the best way to do this is to focus on innovative ideas and trying new things internally. If you are making a change that could potentially affect customers, it should be done with a small group or during off hours to ensure it will be successful.

For culture changes, it's recommended to try new programs with a small subset of employees, get their feedback and use that to improve the program before you roll it out to others. Ideally, you can run a few pilot programs before starting the program with everyone, but even one test run will increase the likelihood that whatever new program you are starting at your organization will give you the results you want.

Fostering a culture of psychological safety where employee innovation thrives is key to being successful in this rapidly changing business environment. Letting teams take risks, make mistakes and learn from them is crucial to create that culture.

By following the steps above, you can create an innovative culture on your team without impacting the bottom line of your company.