In the sports world, the best players don’t always make the best coaches.

Wayne Gretsky is called hockey’s “Great One” for a reason. As a player, he won 4 Stanley Cups and 9 MVP awards. But what some people may not know is that he also coached in the NHL. In his four seasons coaching the Phoenix Coyotes, they didn’t make the playoffs once.

That story often repeats itself. Magic Johnson is considered one of the greatest basketball players of all time. He won 5 NBA championships with the Los Angeles Lakers and an Olympic gold medal as part of the 1992 Dream Team. After his retirement, he also tried his hand at coaching. He resigned after only 16 games.

It’s the same truth for the business world, too.

Just because you are good at a particular skill doesn’t mean that you would make a good manager. So, why is that the standard career path for so many in the corporate world? And how can companies avoid creating an “accidental manager”?

To answer those questions, we spoke with Cary Cooper. He's a professor of organizational psychology and health at the University of Manchester, the author of "Wellbeing at Work: How to Design, Implement and Evaluate an Effective Strategy," and former president of the Chartered Institute of Personnel and Development.

Middle Managers’ Difficulties. Frustrated Middle Managers. Discontent of Middle Managers. Job Outlook for Middle Managers.

Middle managers are the least confident they’ve ever been. Why are middle managers so miserable? How to loosen the squeeze on middle managers.

Those are all headlines about middle managers. The first group were published between the 1970s and 1990s. The second, in 2023 and 2024. How has the story not changed for middle managers in over 50 years?

That’s what we are diving into with Season Three of the Return by putting a spotlight on a group of workers who have largely been overlooked and ignored. Middle managers are stressed, overwhelmed and unhappy. And they have been for decades.

To kick us off, we first need to define what a middle manager is. For that, I spoke to Emily Field, partner in McKinsey's people and organization practice based in Seattle. She’s spent the last few years deeply researching the topic of managers for her recently published book, “Power to the Middle: Why Managers Hold the Keys to the Future of Work.”

She tells us more about why this role is critically important to the workforce, how middle managers are emotional lifeguards, and how it’s evolved over time to become just that much more challenging.

Her unpacking of what middle management is sets us up for a season that talks about accidental managers, 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.

WorkLife is proud to present season three of The Return, a podcast about the modern workforce, with this season focused on middle management.

Last season, we heard what it’s like for Gen Z to enter the workforce for the first time in a post-pandemic world. We highlighted themes like why values are so important to Gen Zers, whether or not they are loyal to their employers, how they use TikTok for career advice, what it means to be a young professional who is a boss to older workers, and so much more.

This time, we’re hearing from the population of workers that some argue is the backbone of a successfully-run organization: middle management. They are the ones who are navigating those RTO mandates, welcoming a new generation of workers that have a different approach than those who came before them, the rise of artificial intelligence – the list goes on.

In season three of The Return, we speak to middle managers themselves to hear beyond their everyday stresses of the job, but what they need to guarantee everyone they manage has what they need to be the best at what they do. C-suite, listen up because they need your help too.

We dive into how middle management stress is a decades-long issue (there are New York Times headlines dating back to 1971), how the wrong people are being chosen to be managers which is leading to the rise of “accidental managers,” what it’s like to have hard conversations and having to be a therapist at times, where people are finding support as a middle manager, and how AI is impacting the job of a middle manager.

With a Q+A format, you will hear in-depth conversations with folks including Colette Stallbaumer, Microsoft’s general manager of Microsoft 365 and Future of Work Marketing, Rob Pierre, former CEO of advertising services platform Jellyfish, and Emily Field, partner at McKinsey & Company who co-authored “Power to the Middle: Why Managers Hold the Keys to the Future of Work,” to name a few.

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 – to hear the first episode on Tuesday, April 23.

Since we first started reporting for season two of The Return in January, a lot has changed. Our guests have continued to face uncertain workforce conditions that include, for some, layoffs or difficulty finding a job, while others have talked about how they have experienced new jobs or being promoted.

Throughout the year, we’ve seen artificial intelligence continue to boom while people worry how it’ll impact their jobs, return to office mandates plaguing the country forcing people to change their schedules and ongoing challenges around employee experience. And Gen Zers are experiencing all of that for the first time, without any sort of existing playbook. But Gen Zers aren’t shy to change, which we’ve covered throughout this season.

On this episode, we circle back to talk to a few guests who we spoke with earlier this season to see where they’re at now. Is Julie still balancing multiple jobs at once? Did Aldrin find a job that aligns with his values? Is Genesse happy with the working conditions at HarperCollins post-strike? And how else has Danielle relied on her friend-tors?

We also speak with Marcie Marriman, EY Americas cultural insights and customer strategy leader who helped conduct EY’s 2023 report on Gen Z to learn her key takeaways on how Gen Z is reshaping the workforce.

Plus, listeners call in and tell us their point of view on how Gen Z is impacting the future of work.

Gen Zers have definitely navigated wobbly territory and were given another lesson in resilience since the pandemic. It might have felt difficult and disappointing at times, but there is a lot of positive change happening in the workplace that we uncovered in season two of The Return.

Gen Zers are thinking about their identities and how they want to show up at work. This generation is all about authenticity, but for non-binary or transgender persons, that might mean jeopardizing your job, which is a lot to consider.

Corporate America has stepped up its support of LGBTQ+ rights. It is more widely accepted to be out in terms of sexual identity in the workplace. However, there is still a long road ahead to foster a truly inclusive environment, especially when it comes to gender identity. Gen Z young adults are much more likely to identify as either trans or nonbinary than other generations. A Gallup survey found that the number of Gen Z people identifying as transgender is twice that of millennials.

In this episode, we speak to Gen Z founder Yen Tan who came out during the pandemic. The pandemic created a laundry list of negative impacts, but one positive outcome was that it gave people time to discover more about themselves during their time working from home. Since then, Tan has created a truly inclusive workplace in the company they created.

That's something Kat Kibben told us is important for companies today. Kibben is the founder of Three Ears Media, a company that offers pronoun education to workforces. The phone calls from organizations peak during Pride Month, but Kibben says it's crucial work year-round, especially when there is a rise in anti-trans legislation. There are 583 such bills across 49 states in 2023, according to translegislation.com.

Of the proposed anti-trans bills, 14 are in Florida, where Gen Zer Lana Patel grew up. In this episode, we hear her first-hand experience about transitioning and the lack of support she received from employers over the years. Today she works at Plume, a gender affirming health care company for the gender diverse community as the PR and government affairs liaison.

WorkTok, or CareerTok, is in full force.

Combined, those hashtags on TikTok have over four billion views. There are sneak peaks into “a day in my life” from the perspective of everyone from McDonald’s employees to top executives at Fortune 500s. You can hear people vent about how they struggle to nail a work-life balance and there are those who share their 9 to 5 routines and how they find time for fun things to do after work. And there are salary transparency videos and even tips from career experts on how to land a job.

In fact, Gen Zers are swapping LinkedIn for TikTok, realizing they can find job opportunities in an environment that is more attuned to their career and workplace goals and hopes. Andrea Moreno, who we speak to in this episode, is one of them. She landed her job as a PR account executive thanks to a TikTok connection.

Also in this episode we speak to a WorkTok creator, Jerry Lee. His account is devoted to giving career advice, including how to optimize the job search process, how to write a better resume, how to ask for a raise and even how to deal with passive aggressive co-workers. Shola West, a Gen Zer, has also dedicated her TikTok to covering career tips, leaning into building her own brand as a young professional working in media and marketing.

Want to be featured in a future episode? All season we’ve been hearing directly from Gen Z workers about their experiences starting their careers in this new era of work. And now we want to hear from you. If you’re a member of Gen Z, or a manager of one, or even a parent of one, we want to hear your thoughts on friend-torship, work-life balance, quiet quitting, and any other ways you think this new generation is changing the way we think about work. You can call and leave a voicemail at 845-580-2884 or send a voice memo to [email protected] and it might be featured in a future episode.

Our whole lives we're told to look up to older people, learn from them and take their guidance. But what happens when a Gen Zer ends up in a leadership position managing people older than them?

We spoke to Gen Z bosses about the realities they face as they work with older generations. They’re bringing fresh perspectives that might be misunderstood by more seasoned workers. In this episode, we check back in with Jerah Reeves, who we spoke to earlier in the series, to see how he handles these dynamics. Reeves is the coordinator of the transformational leaders program at Binghamton University of New York, where he helps students – many of whom are older than him.

Leaders are getting younger overall. Nearly a third of newly appointed S&P 500 CEOs last year were younger than 50 years old, which is more than twice the rate in 2018, according to research from McKinsey & Company.

Want to be featured in a future episode? All season we’ve been hearing directly from Gen Z workers about their experiences starting their careers in this new era of work. And now we want to hear from you. If you’re a member of Gen Z, or a manager of one, or even a parent of one, we want to hear your thoughts on friend-torship, work-life balance, quiet quitting, and any other ways you think this new generation is changing the way we think about work. You can call and leave a voicemail at 845-580-2884 or send a voice memo to [email protected] and it might be featured in a future episode.

The days of working for one employer for the majority of your life are long gone.

Our relationship with work has slowly evolved over time. In 2022, 22% of workers aged over 20 years old spent a year or less at their jobs – the highest percentage with a tenure that short since 2006, according to data from the Employee Benefit Research Institute. About 33% spent two years or less in their jobs over the same period.

But Gen Z takes it a step further: they aren't even dedicated to a single employer at one time.

According to research from marketing data and analytics company Kantar, 40% of Gen Zers report having two or more jobs. That’s a figure that suggests that “quiet quitting” is no more than the need to be at their next job on time.

In this episode of The Return, we talk to two Gen Zers who have opposite beliefs regarding job loyalty. Kyle Lawerence stayed at his first job in the finance industry for 14 months, even though he didn't enjoy it because he was fully remote and it was hard to make connections. Julie, on the other hand, is juggling four to five jobs at any given time – her 9 to 5 and other gigs, like barista, cater waiter, and events coordinator.

Rikki Goldenberg, a career and leadership coach, breaks it down for us in this episode. How does a Gen Zer make the decision to quiet quit? And how does that turn into actual quitting?

In this episode, we break down how important corporate social responsibility is to Gen Zers looking for a job. Making sure that a company’s values align with their own is at the top of their checklist.

That mindset has impacted their job search, to the point they even say no to the highest paying positions to work at a company that closely aligns with their values instead.

Choosing a career that aligns with your values was the case for recent college graduate Aldrin Villahermosa II. Growing up on the island of O’ahu in Hawaii, he saw a shortage of healthcare workers and systemic issues in the public health sector. That's why he pursued a master's degree in public health.

And Gen Zers aren't just choosing a career that aligns with what they value – they're joining unions too. Genessee Floressantos, associate publicist, international sales at HarperCollins Publishers, tells us what it was like to be a part of HarperCollins' nearly 90-day strike.

In this episode, we talk about the importance of mentorship in the workplace. There’s an awful lot to learn from experienced workers, and there has been a long tradition of passing down that experience – usually, in the office. But when Gen Z entered the workforce, it was remote. How did that impact building mentorship in the earlier days of their careers? 

Tracy Ziemer, one of host Cloey Callahan's first mentors, shares what advice she passed on to Callahan over Zoom at the beginning of her career. And Danielle Farage, a Gen Z entrepreneur, tells us how she is redefining mentorship with the idea of "friend-torships."