The 21 Hats Morning Report

The 21 Hats Morning Report

Has There Been a Trickier Time to Manage People?

Inc.’s Ask a Manager columnist says her inbox indicates the answer is no.

Loren Feldman's avatar
Loren Feldman
May 13, 2026
∙ Paid

Good morning!

Here are today’s highlights:

  • This is a very tough time for nonprofits.

  • Americans may be tiring of subscription pricing, but it remains irresistible for businesses.

  • AI is making the challenge of ADA-compliance litigation even worse.

  • Dean Buntrock turned a 12-truck garbage company into a behemoth.

A Great Night at the Great American Ball Park

And a great start to 21 Hats Live: Cincinnati. Last night, 21 Hats took over the SkyBar, spent some quality Q&A time with Reds owner Phil Castellini, and even managed to watch a little baseball. And yes, that’s 21 Hats in the fine print on the right-field scoreboard (captured by Courtney Moncrieff). The event goes into full swing today.

HUMAN RESOURCES

Inc. suggests solutions to 10 messy office dramas: “As someone who has written an office advice column for nearly two decades, I’m here to say: It’s a weird time to be at work. I can’t think of another period in modern history when workplace trends changed as quickly and as dramatically as they have over the past five years. ... A huge factor: 52 percent of people work in a hybrid environment and 26 percent are exclusively remote, according to a recent Gallup poll. This carries challenges that organizations are struggling to address.”

  • “Bonding goes by the wayside. Ditto casual communication—it takes extra energy and coordination when you can’t pop into someone’s cube or catch them in the hallway. Junior employees struggle to form relationships, absorb the rhythms and culture of working life, and learn from experienced colleagues. Remote work also creates an uneasy tension between workers who want to be trusted to be productive when not in their employer’s line of sight, and leaders who believe the magic only happens when everyone’s on the same floor.”

  • “What does this mean for leaders? Based on my inbox at Ask a Manager, it means they’re walking on eggshells. From where I sit, mistrust between employees and those who oversee them is at an all-time high—as is dissatisfaction with work in general. To manage effectively in 2026 is to win over the cynics, so it’s more important than ever to operate transparently, collaboratively, and with sensitivity to the state of the world. Organizations should focus on aligning outcomes, not hours; measure progress with collaborative goal-setting and short feedback loops; establish clear operating norms (and boundaries) for things like availability and responsiveness; and address performance issues early and forthrightly.”

  • Alison Green offers answers to these questions: “Is there a humane way to fire someone in an open-plan office? Should onboarding an entry-level staffer be this much work? Can I keep employees late during busy times? Can I hire an employee’s replacement before the employee is out? Can an employee work too hard? Should I have told an employee I figured out she was pregnant? A perfectionist employee is costing the company money. How do I get him to cut it out? A new hire is trying to ‘manage up,’ but he’s really bad at it. How do I get my management team to lay off the booze talk? I made a report cry. Was it me or them?” READ MORE

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