How to deal with a Millennial boss and still keep your job
Millennial bosses are taking over – but they’re a work parent, colleague, and manager rolled into one. Here’s how to impress them
Boomers are retiring, Gen X workers too. A new boss has entered the bull pen: The Millennial.
This is the kind of leader who wants to rewrite corporate rules: Huddles instead of scheduled meetings, sneakers on Monday, work-life balance, menstrual leaves for women. They’re Work Dads, Work Moms, they’re the buddy to drink with. Fun, flexible, sooo easygoing. What could go wrong?
Plenty. Millennial bosses in middle-management are sandwiched between laidback Gen Z and an older, stuffier generation. They’ll swing between chill manager and corporate slave. They can’t decide whether they’re boss or friend. They hate confrontation. They hate appraisals.
How to deal? Millennial and Gen X experts have some hacks.
Treat them like a boss, not a bestie. Avoid being informal too soon, recommends Viniti Sareen, HR manager and career counsellor. “With Boomers, there was a clear chain of command,” she says. “The millennial boss often doesn’t want cabins. They often have a meal together.” They’re even open to being challenged by a junior. But while boundaries blur, hierarchies persist. “Remember, this person is still your boss,” says Priyanka Deshmukh, founder of The Heart Intelligence Coach. Challenge authority with respect.
Read your report card. “Millennials often hesitate to give negative feedback,” says Sareen. They fear being perceived as offensive. To avoid nasty surprises during appraisals, pay close attention to how a millennial boss phrases praise or criticism through the year.
Millennials have never really exercised the ‘feedback’ muscle,” says Neha Jalan, founder, WeCoach. They drop hints rather than give clear instructions, and waffle through their advice. It makes a teaching moment harder to recognise. So, read between the lines. “What they say may not be the whole truth,” she says. “Figure out what part of your effort is working for them, and what’s not. For example, is speed important or high-quality work?”
Be the grown-up. “Most millennials hate to micromanage,” says Sheeja Shaju, founder-CEO of the leadership coaching firm, I Create. “They don’t want to give instructions, so don’t wait for them. And when you approach them with a problem, carry a solution along.” Deshmukh adds that it helps to prep: “Ask them clearly what they need from you, what two or three things are important to them, and how they would rate you in specific areas.”
Put in the work. A job’s a job, no matter how old or young your boss is. “If your firm has set hours, allows you to leave when you’re done, and values your well-being, it means they expect you to be disciplined,” says Sareen. All bosses expect reliability, even the flexible ones. “They appreciate when you reduce their stress by communicating clearly and meeting deadlines and targets,” says Smriti Vats, owner of Senior Solutions - Leadership Development.
Play to your strengths. Gen Z workers understand tech instinctively. They should jump in more to solve problems at work, says Vats. A good way to do it is by helping manage social media strategy or using AI and apps to streamline tasks. “Understand the business, and show how you can solve a problem,” Vats says.
Don’t race to the top. “While Boomers gave out promotions only after employees put in the years, Millennials tend to promote and empower teams faster,” says Shaju. Still, true growth takes time. “Don’t expect an instant promotion,” says Sareen. “Gen Z expects quick career jumps. Show your value first.”
From HT Brunch, March 29, 2025
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