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3 ways company leaders are failing middle managers



The data is in: Middle managers feel overworked and underappreciated by their employers. Seven in 10 middle managers today say they’d love to return to being independent contributors if they could keep the same pay, according to a recent study by The Predictive Index and HR Dive’s studioID. But unlike “Sabrina the Teenage Witch,” they can’t make their problems disappear. 

Failing your middle managers means losing the people who keep teams and companies intact. “[Middle managers] are all too often unsung heroes that hold the team together,” says Rod Thill, viral content creator and founder of WorkDaze, a newsletter about work culture. 

“It’s time for companies of all shapes and sizes to recognize the positive impact of middle managers to plan for the long term,” he says. 

We turned to Rod for his Inspector Gadget-like lens into what’s happening behind the scenes and the screens of middle managers at work. He shared some stories that will make you cringe — along with advice for middle managers in similar positions and employers looking to avoid putting their people in these positions. 

Epic fail #1: The helicopter boss

What happened: One WorkDaze reader, who had years of management experience and had been recently hired to run a department, lamented how they have to run every decision by their higher-ups. “They even ask to see my emails before I send them out externally!” TBH, we’re not surprised, given our research shows just 7% of people leaders say middle managers in their organizations have total authority over the areas they manage. 

Advice for middle managers: “As awkward as it’s going to be, you have to tell your boss (in the nicest way possible) to take a chill pill,” says Rod. “Explain how their constant helicopter-ing is preventing you from being productive — which makes your direct reports less productive, too, and ask for direct feedback on what you might be doing to warrant their Babysitter’s Club behavior.”

Advice for employers: “Don’t not trust the employees you hire unless they’ve given you a reason to peek at their timesheet each week. Stop doing it,” Rod says. 

Epic fail #2: ‘Blackout dates’ on PTO

What happened: Another WorkDaze reader wrote to Rod and told him how their company claims to have “unlimited” PTO but then sets blackout dates (including Fridays before long weekends) when no one can take off. (Talk about being disappointed when you read the fine print.) Just 6% of companies offer unlimited PTO, and Rod’s story makes you wonder how many of these set blackout dates. 

Advice for middle managers: “As a team leader, it’s time for you to have a little chat with the boss to help voice your crew’s frustration. … Listen to your boss’s concerns, represent those of your team, and then regroup a few days later with a plan that hits on every one of them. I’m willing to bet there aren’t actually that many,” suggests Rod. 

“Maybe that looks like working an extra hour or two one day per week or setting specific deadlines for those follow-up emails your boss thinks won’t get sent if anyone takes PTO. Either way, it’ll be hard for your boss to deny an actionable, thorough plan that works for everyone.”

Advice for employers: “Don’t advertise unlimited PTO for your employees if their PTO is actually going to be limited,” advises Rod, who also says the (fake) policy reminds him of when clothing brands give you rewards that you can’t use on sale items. 

Our two cents? Recognize that your employees need time off. Our data shows that 99% of people leaders believe middle managers are stressed. The bottom line: If you don’t give them a break, they’ll find an employer who will.

Epic fail #3: (Un)sustainable growth / Smells like slippage

What happened: Yet another WorkDaze reader told Rod how, though the company they work for is growing, their leadership can only see the extra profit and refuses to hire more people so the organization can grow sustainably. Their small team is unable to keep up with the ballooning workload, causing things to slip through the cracks. Our data backs this one up, too, as one in four middle managers wishes they’d receive more executive support regarding inadequate staffing. 

Advice for middle managers: “Often, a super quick-growing company is powered by a team doing way more than what’s in their job descriptions,” Rod notes. “Ask your direct reports to write down everything they’re doing that they weren’t originally hired to do, and bring that list of everyone’s extra work to the bigwigs as proof that it was time to hire more talent, like yesterday.”

Advice for employers: “Don’t wait until things get unbearable to hire more support and bring in more resources,” Rod urges. “If you wait too long, you’re either going to be left with 1) a burned-out and unproductive team or 2) no team at all because they all quit.”

Failing forward

While these scenarios sound bonkers, our data suggests they’re not rare occurrences. What else occurs when situations like this play out? People leave. Further research shows that 70% of Gen Z and Millennials planned to quit in 2023. Avoid these cringe-worthy situations to avoid attrition — and do it fast. 

How? Stop taking your middle managers for granted and start valuing their needs. “Check in with your middle managers, make sure they have the resources they need to feel supported,” says Rod. “And for the love of Shania Twain, give them that well-deserved raise already!”

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