How to have hard conversations as a manager: The Return podcast, season 3, episode 4

By Cloey Callahan  •  May 17, 2024  •

Ivy Liu

This article is part of a special podcast series that covers the challenges and opportunities of returning to the office. More from the series →

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A therapy session and a one-on-one with your manager can be eerily similar.

In fact, managers often have to navigate tough conversations with team members. Those conversations range from figuring out a flexible work schedule so that your team member feels comfortable picking up their child from school instead of attending a 4 p.m. meeting to telling a team member they’re being laid off and will need to turn over their laptop ASAP.

No matter what exactly it might be, these kinds of conversations demand a certain level of grace and understanding by the manager. So how do you have those conversations?

To get a better understanding of why the people part of management is so important, we spoke with Julia Toothacre, who has worked with thousands of clients with their career paths in her role as a seasoned career coach and strategist at Ride The Tide Collective.

Across six episodes, season three of The Return explores why middle managers are constantly overwhelmed and what needs to be done to help this cohort of workers who are arguably the most important to a company’s DNA.

We will explore topics including the need for training, where managers can find support, how they navigate tough conversations, and how AI is helping them free up their time to focus on the people part of management.

Season three of The Return is hosted by Cloey Callahan, senior reporter at Digiday Media’s WorkLife, and produced by Digiday Media’s audio producer Sara Patterson. Subscribe to the WorkLife podcast now on Apple Podcasts, or wherever you get your podcasts.

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