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Chief Learning Officer Podcast


Sep 9, 2019

Like many bosses, Jon Kaplan thought he was a good leader.

The results seemed to prove it. He worked his way up from aspiring academic to public school teacher to corporate instructional designer and eventually into the top learning job at Discover Financial Services, a Chicago-area firm with 17,000 employees.

The only problem? His team didn’t agree with his assessment. “I was there for about three or four years and I had managed to take a team that should have been high performing and I just drove them into the ground,” Jon said. “It just was really unpleasant.”

What he did in response catapulted his career forward and led to some of the learning organization’s greatest successes.

In this episode of the Chief Learning Officer Podcast, Jon talks about that “crucible of leadership,” how he rebuilt himself and his team in the wake of his failure and how they came to establish the Discover College Commitment, an industry-leading tuition assistance program that all Discover employees are eligible for starting on their first day.

Plus, Jon and Justin Lombardo talk about why they left academia for the corporate sector and guest co-host Ashley St. John, managing editor for Chief Learning Officer, shares what she’s learned in her first two years on the job and what she looks for when selecting a magazine profile candidate.

Podcast Producer: Jesse McQuarters

April 2019 Profile: Discover Financial’s Jon Kaplan