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Learning to Unlearn: Changing the Behaviors That Hold You Back

Podcast host Sam Massey | Podcast guest Barry O’Reilly
August 29, 2019 | 23 min 48 sec

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Brief summary

Many of us are guilty of clinging to once-useful mindsets and behaviors, that were effective in the past, but no longer serve us in today’s rapidly evolving world. Executive coach, Barry O’Reilly shares how leaders can unlearn their outdated behaviors to take the next step forward for more effective leadership. If you are a business or tech leader, seeking practical approaches to evolving your organization into modern digital businesses, this is the podcast for you.


I’ve worked with amazing leaders all over the world. I came to realize that what was holding them back was not their ability to learn new things, but their ability to unlearn the existing behaviors- that had made them successful up until that point- but were no longer creating value. 

The world is changing. Customer demand is changing. Technology is changing. If you haven’t built the capability to react to these changes, at some point in the future, some of your behaviors will no longer work for you, or create the outcomes you want to achieve.

The biggest role of leadership is to role model the behaviors you want to see others in the team exhibit, which has a network effect. If leaders experiment and try new things, and share what worked and didn’t, others in the company will start doing that too. 

So, successful leaders are great experimenters. They are constantly looking for opportunities to get outside of their comfort zone. They think big, but start small to experiment and iterate their behaviours in an intentional way. 

Knowledge used to last a lifetime. Not anymore. If you think of knowledge as a cup, and keep pouring new knowledge into it, it starts overflowing. You need to empty some of it and re-fill it with new stuff.

You need to adopt a system that allows you to continually identify and adapt to changing circumstances- recognizing what behaviors are working- and doubling down on those- and what behaviors are holding you back- and unplugging those for now. 

One of the biggest obstacles for experienced leaders, is their own expertise, because they believe that their own assumptions are always correct, since they have usually been in the industry a long time. Listening to the customer and acknowledging what they tell you, is vital.

Trying to do too many experiments or changes on yourself in progress limits your ability to change. Choose one or two things to experiment with so that you are able to correlate outcomes with that change.

Sometimes leaders don’t believe that they need to change. Their feedback mechanisms tell them that they have been promoted for a reason, or their metrics are good. So they can be complacent about the need to change. But a disruption in the business world can happen overnight- so becoming comfortable with being uncomfortable to keep sharp and reducing learning anxiety is critical.

My biggest unlearning in working with leaders was recognizing that I don’t change companies; companies change themselves. I can give advice, support and counsel, but I needed to realize that the ones that transform are the ones that do the work themselves. 

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