Author Ryan Leak: ‘Do You Know What It’s Like To Be On The Other Side Of You?’

Ryan Leak joins the show to talk about his new book Leveling Up: 12 Questions to Elevate Your Personal and Professional Development. Of the dozen questions leaders can ask themselves to improve, one stood out: “What’s it like to be on the other side of me?”

Ryan says that asking employees to answer that question, and providing a safe space in which to do so, are “desperately needed” in many workplaces.

“We’ve all worked for the leader who did not know what it was like to be on the other side of their emails, on the other side of their reply-alls, on the other side of their scheduling and on the other side of their rants,” Leak pointed out. “We all have to ask this question. ‘What’s it like to be on the other side of my leadership, my parenting, being married to me?’”

If experience has taught Leak anything, it is that too many leaders come to the conclusion (or delusions) that what it’s like to be on the other side of them is awesome. “To which, I would reply, ‘Are you sure? Are you positive? When was the last time you checked in with somebody else to verify your attitude?’” said Leak.

Leak credits basketball with teaching him how to overcome his fear of failing and reach outside his comfort zone in order to obtain useful feedback. An All-American basketball player at NCAA Division III North Central University in Minneapolis, Minnesota, Leak never saw professional basketball as a realistic career option, but it nagged him that he never tried. So, he took the bold step of writing emails to every NBA franchise asking for a tryout. Of those, only one, the Phoenix Suns, granted him one. He didn’t make the team but he used the experience to show others how chasing failure just might lead you straight into the arms of success.

In the podcast, listeners will be inspired by Leak’s thinking and emboldened to emulate his self-improvement tactics. These include:

6:00   How to embrace failure and allow it to propel you.

17:00  How to create a failure-friendly environment within your organization.

19:00  How to speak candidly to job candidates.

25:00  List of questions that will start meaningful conversations.

26:00  What it is like to be on the other side of you.

33:00  The best way to honor and validate your coworker.

34:00  How to give your team permission to point out your blind spots.

Leak says that as leaders, we often try to hold up a specific image of perfection as the goal. The problem with this mindset, he argues, is that there’s no such thing as perfection—and even if there were, it shouldn’t be the goal. “Perfection isn’t the goal,” said Leak. “I think connection is the goal.”

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