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Easing the Fear of Failure with Guidance

Psychological Safety

24 September, 2021

Brian Flanagan
Brian Flanagan

Head of Product and Growth at Optimity

Brian Flanagan, Head of Product and Growth at Optimity, encourages autonomy informed by the mission statement that the company as a whole exists to serve.


If you look at companies that have failed miserably over time, it’s usually a result of terrible management and a lack of creativity. This happens when the people that make up the team are not allowed to be as good as they can possibly be.

That’s the opposite of the type of environment that you want to create for your employees and throughout the organization as a whole. People who feel comfortable and valued are more willing to take risks, and risk leads to innovation. The worst thing that you can do to a team is to take away their ownership of the solving of the problem and developing a solution.

Actions taken

One of my jobs, as a leader, is to provide context to my teams, to understand the levers that we can pull and how this will influence the business. In the absence of that, your teams don’t know what is most important, they don’t know how your business works so that they can prioritize their work and they won’t understand why you may not see something that they do as unimportant. I’ve been with companies where very little data was freely available and there was a lack of sharing of information.

Because of this, everybody was just running around in circles with little heed being paid to the overarching mission of the company. The actual problems that the company had initially set out to solve fall by the wayside. How can we make our product easier to use or easier to understand?

Working in this way is chaos. It destroys your soul. You make it to the end of the day and have no idea what you’ve actually accomplished. The work may feel great as you do it and the delivery may have gone well, but did anybody care? Likely not.

As leaders, we hire adults and we should empower our employees to act as such, enabling them to make adult decisions. At the end of the day, the reason that you were hired is that you bring a higher level of expertise than your manager has and you should act as such.

The bottom line: I really don’t want to do their job. I have no interest whatsoever. The onus is on me to inspire them to do their job well and to allow them to see their success. Under these conditions, most people will act with good intent.

It’s okay when somebody fails; things usually seem like a much better idea at the time. There is always something new to learn from failure. Now, we know. Great. Don’t feel bad about it. What can you do moving forward?

Lessons learned

  • You see this happen more and more in product organizations nowadays. They become a feature factory. There is no strategy or vision that each move is building toward. The focus should be on how to make your customers’ lives better.
  • Develop a sense of ownership around the value that you want to bring to others. Understand thoroughly the impact of what you’re doing and how it feeds into the bigger picture. Without that, you may be doomed to fail.

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