Episode #92: Mad Terrorists and Middle Managers

Why are middle managers in Japan struggling with Millennials?

Middle managers in Japan face a shrinking workforce and a big generation gap.
Older managers grew up in the bubble era; Millennials only know economic crisis, disasters, and uncertainty.

Millennials want more than a job. They want to feel needed, appreciated, and proud of their contribution. If managers don’t give this, young talent leaves after only a few years — just when they should be most productive.

Mini-summary: Middle managers are on the front line of a talent crisis, and emotional engagement is now a core part of their role.

What is changing in Japan’s talent and career mindset?

• Fewer young people are entering the workforce.

• Immigration is not yet a real solution.

• Birthrates remain low and families are small.

• A huge transfer of wealth from older to younger generations is coming.

• Housing may become more affordable as the population falls.

For Millennials, this means less pressure to chase career security at any cost. With more financial safety and fewer workers, they can be more selective and are quicker to leave companies that don’t value them.

Mini-summary: As financial pressure drops and talent becomes scarce, Millennials gain leverage and are less willing to tolerate poor leadership.

What do Millennials need from their managers?

Millennials want “love, not tough love” in the workplace. In practice, that means:

• Hearing clearly that they are valued

• Knowing that their work matters

• Getting recognition for being useful to others

• Receiving coaching, not just instructions

Global and local research show that feeling valued is a key driver of engagement. When people feel valued, they are more loyal, motivated, and innovative.

Mini-summary: To keep Millennials, managers must actively communicate “You are important here, and what you do matters.”

Official data shows that in about 40% of workplaces, Millennials leave in their third or fourth year. When they go:

• The company loses years of training investment

• Productivity gains never fully materialize

• New hires must be recruited and trained from zero

• The talent shortage gets worse and recruiters gain power

This is not a short-term problem. With fewer young workers entering the market, replacing lost talent will become harder and more expensive.

Mini-summary: Losing Millennials after a few years is a major financial and strategic risk in a shrinking labor market.

What should companies and middle managers do now?

1. Accept that a “war for talent” is coming
   Start planning now for a future where skilled young employees have many options.

2. Update how you lead Millennials
   Traditional “command and control” or silent endurance does not work. Emotional connection and recognition are now critical leadership skills.

3. Train supervisors and middle managers
   Equip them to say and show:

   • “You are valued.”

   • “We need you.”

   • “We appreciate what you do.”

4. Build everyday habits of appreciation
   Use regular check-ins, coaching, and specific praise tied to results and contribution.

Mini-summary: Companies must upgrade middle management skills to retain Millennials — especially the ability to communicate value, appreciation, and purpose.

• Japan faces a long-term talent shortage; Millennials will have increasing power to choose where they work.

• Millennials stay where they feel valued, needed, and recognized — not just well-paid.

• Losing young talent after 3–4 years destroys training investment and future productivity.

• Now is the time to develop middle managers’ coaching and communication skills to retain key people.

Founded in the U.S. in 1912, Dale Carnegie Training has supported individuals and companies worldwide for over a century in leadership, sales, presentation, executive coaching, and DEI. Our Tokyo office, established in 1963, has been empowering both local and multinational corporate clients ever since.