The Return Digiday

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.

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.

What does it look like when an organization doesn’t have any middle managers at all?
In our last episode, we spoke to Cary Cooper, a professor of organizational psychology and health at the University of Manchester, about the pitfalls of promoting an “accidental manager.” He doubled down on why the best player doesn’t always make the best coach, why proper management training is crucial, and how the younger generations are changing management.
So to avoid creating an “accidental manager,” what do you do?
Creating a whole new way of promoting managers is easier said than done. But this week’s guest did just that. Rob Pierre is the ex-CEO of Jellyfish, a global digital marketing company. During his time leading the company, Jellyfish pioneered a new way of thinking about the managerial path and debated if we need managers at all.
Throughout this episode, Pierre shares how Jellyfish operated without middle management, whether or not it was hard to implement, and how other organizations can replicate this model.

A therapy session and a one-on-one with your manager can be eerily similar.
In fact, middle managers are often navigating tough conversations with team members. That is heightened today in this return to work era that puts new dynamics at the forefront like hybrid and remote work.
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 o’clock 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 middle 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.

One of the most common ways workers can find support and camaraderie is through a union. But what if your role doesn’t allow you to be a part of a union?
That’s the case for middle managers.
According to the National Labor Relations Act, managers are prevented from joining unions because it creates a conflict of interest. So where does that leave managers when it comes to support? Like in so many other instances, they are falling through the cracks.
Without formal support groups, middle managers, like today’s guest, have to go out of their way to create their own. Erin Mantz is currently a middle manager at communications agency Zeno Group, who has also been a middle manager at big tech companies throughout her career. She says her informal support group is necessary to stay above water.
In this episode, she tells us how her support group operates, the benefits of having a support network, and where other managers might find their own support to get one of the hardest corporate jobs done.

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.