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Cultivating Accountability


24 September, 2021

Brian Flanagan
Brian Flanagan

Head of Product and Growth at Optimity

Brian Flanagan, Head of Product and Growth at Optimity, takes a balanced approach to leadership that does not shy away from looking painful truths in the eye.


As a leader, you need to create an environment where the people around you feel safe as they do their work. This does not necessarily mean an environment devoid of consequence as there needs to be some sense of accountability. You have to believe that people do their work with the best intentions for positive outcomes.

Everyone needs to understand your role in any outcome. “Okay, I did this thing. It happened. Was it good, or was it bad? What did I learn from it, and what can I take with me afterward? What would I do next time?”

Actions taken

We use what we’ve learned in order to continue to do better. I think that this notion is one that the kumbaya, everybody-holding-hands approach tends to miss.

As a leader, my first instinct is not to fire you when you’ve run a bad test or when you’ve created a feature that did not work very well. Instead, what I ask first is what the person has learned. How will you apply this new knowledge differently later on?

The goal is to allow the person to avoid mistakes so that they don’t repeat them. It’s the variation between these schools of thought that is really important. Many leaders miss the opportunity for growth because they’re all terrified of having any type of honest conversation. It’s sad, but that’s the heart of it. You see it everywhere. I try to take every new development as a positive opportunity.

If the conversation is focused solely on work, nobody’s feelings should get hurt. The highlight of your life as a professional should not be receiving a medal of participation. This way of thinking does not result in a strong team or company. I would so rather work with people who have either succeeded enormously or failed spectacularly. In both cases, I’d expect them to have learned from these experiences and allow their coworkers to benefit from their experiences.

As a leader, it’s on me to foster an environment where they can be the best possible version of themselves. They feel comfortable being thoughtful and creative. This sense of safety is what enables them to bring their best work forward.

It’s never tough love when the conversation is honest and initiated with good intent. The bar of expectation should be taken higher continuously as your reports meet each tier of performance progressively. As everybody levels up, I am never hesitant to ask for more.

Lessons learned

  • On an individual level, it’s all about having that sense of ownership when things do not go as planned. I admit freely when I have not succeeded in some way. I learn from the failure and try my best to make sure that the problem does not happen again.
  • Tough love does not mean withholding all positive feedback from your reports. You can still pat them on the back when they’ve done something great. There should be an equal amount of expectation for constructive criticism when it is due, however. I, as a manager, expect the same thing from them. This humility keeps me from trodding all over somebody’s space when I need to be listening just as much as they are.
  • Leaders need to be aware of their own emotions and understand how their words and actions impact others, particularly people on their team.
  • With mutual feedback, I improve right along with the person in front of me. There is a level of maturity and a level of comfort that comes necessarily with all of these things.

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