Middle Management Challenges: Expert Solutions from Top Leaders

The “middle management crunch” continues to be one of the toughest to overcome in today's business world. Stuck between carrying out strategic plans from higher-ups and meeting the everyday needs of frontline staff, middle managers often find themselves in a tough spot that calls for a special set of abilities.

In our recent webinar with Geoffrey Roche,Senior Vice President, Healthcare Solutions at Risepoint, discussed the specific skills that middle managers need to learn to be successful. These include the ability to lead a workforce spanning different generations, to keep growing as leaders, and to create an environment where people feel safe to speak up. 

This article recaps the main takeaways from our webinar, giving real-world answers to the four biggest problems middle managers deal with these days. 

If you're having a hard time juggling leadership duties with getting things done, or trying to keep up with fast company changes, these tips backed by pros will help you do your job better.

You can also watch the webinar here.

Challenge 1: Balancing Leadership and Execution

Middle managers face a tough spot in organizations, creating unique challenges for those stuck between upper and lower levels. A Columbia University study revealed that middle managers deal with conflicting roles; they have their problems while people expect them to solve them. To handle this balancing act well, they need specific strategies.

The two-sided job of middle managers

Middle managers work in what people often call the "sandwich position." They're squeezed between what top bosses want and what frontline workers need day-to-day. 

Companies ask middle managers to do more now than ever before. They must lead, handle changes, reach performance targets, and keep their teams inspired all while dealing with five different age groups of employees.

And most of the time? They do this without much help.

As Geoffrey said, "We expect middle managers to deliver, but we don't always give them the tools or resources to succeed." This leads to exhaustion, annoyance, and, in some cases, people quitting leadership jobs.

Challenge 2: Navigating Cross-Generational Teams

For the first time, workplaces now include five generations working together. This mix creates one of the toughest middle management challenges today: bridging the gaps in expectations, values, and how people communicate.

Understanding generational expectations

Today's workforce has five different generations: the Silent Generation (2.0%), Baby Boomers (18.6%), Generation X (34.8%), Millennials (38.6%), and Generation Z (6.1%). Each group brings its own unique views shaped by different historical events, tech advances, and cultural backgrounds.

A Deloitte study found that 6% of leaders feel ready to lead multi-generational teams. Why? Outdated systems fail to connect with today's workforce.

Geoffrey noted that some companies avoid discussions about empathy or psychological safety. But younger employees crave these talks. They value purpose, inclusion, and knowing their opinions count.

Shift from "Job" to "Experience"

The webinar highlighted a key point: Work has evolved beyond a job. It's now an experience.

People need connection. They seek meaning in their work. This holds true for all generations, not just younger staff.

Here's how leaders and middle managers in particular can make that happen:

• Listen more: Don't just ask how people are doing. Ask why they feel that way.
• Take action: If something's broken, fix it. If something's working, do more of it.
• Stay open: People learn and talk in different ways. Give them choices.
• Bring everyone in: Make sure you hear from everyone, new hires and old-timers alike.

Closing the communication divide

Different generations prefer to communicate in different ways.

Studies show Gen X often likes phone calls, while 83% of Gen Z emoji users prefer to express emotions through emojis. These differences can lead to misunderstandings because our brains process unfamiliar accents differently. People might remember less what someone said or question the speaker's credibility.

Good middle managers can close these gaps by:

• Using many communication channels (digital platforms for younger team members more direct access for older employees)
• Putting listening into action to "tune the ear" to unfamiliar speech patterns
• Setting clear communication rules and expectations.

Challenge 3: Managing Up and Down at the Same Time

Stuck in the middle of the corporate world, managers in the middle face a unique challenge: they need to keep good relationships with people above and below them. This double duty creates one of the toughest parts of their job, needing different skills for each direction.

The stress of getting along with top bosses

Managers in the middle often have to put into action decisions they didn't make, while still being on the hook for results. This creates a tricky balance between what the company wants and what's possible on the ground.

The main challenge is to manage up and communicate well with executives who expect results without always getting the limits faced by workers on the front lines.

As one CFO shared, knowing team members were struggling while still needing to meet company goals puts a lot of pressure on leaders. Middle managers should share strategic plans with employees rather than withholding information. This creates work relationships that benefit both sides.

Building trust with direct reports

Trust is key to managing people who report to you. A strong base of trust improves work relationships, boosts teamwork, and makes people feel safe to speak up. 

When employees feel secure and trusted, they're more likely to share new ideas, question how things are done, and put their all into their work.

To build trust, you need to take specific steps:

• Show you're accountable: Have your team's back by taking charge when plans go off track
• Be open about weaknesses: Admit to slip-ups, which makes leaders more relatable and builds stronger team connections
• Talk with understanding: Give support and show empathy instead of just giving orders in tough situations

Keep in mind, 91% of business executives said that building and maintaining trust had a positive impact on their bottom line. In contrast, a lack of trust "eroded brand value, hurt financial performance, and limited a company's ability to attract and retain talent.”

Leadership That Grows (Without Burning Out)

Growing as a leader isn't about more work or fancier job titles. It's about making systems that help real people.

This includes:

• Giving brief, targeted learning chances (not long dull talks)
• Using tools that work (and fixing the ones that don't)
• Giving credit to people skills and teamwork

As Mickey said, "We need intelligent leadership systems that don't just feel like corporate talk."

Final Thought

Middle management is a tough job, balancing leadership with hands-on work, requiring good delegation and time to think. Our diverse workforce needs bosses who close communication gaps and use reverse mentoring to build strong teams.

Middle managers handle relationships up and down. Top leaders build trust with teams and sway higher-ups. Rapid workplace changes make team resilience crucial for success.

The tips from our experts in the 2025 leadership talk provide practical solutions rather than just ideas. These strategies acknowledge the challenges middle managers face and offer straightforward ways to address them. While being a middle manager remains difficult, those who apply these expert-endorsed methods will likely perform better, benefiting both their teams and the organization as a whole.

As Geoffrey stated, "Every person wants to feel heard, valued, and respected. When we build a culture around that, every generation wins."

Couldn't put it better myself.

Didn't make it to the webinar? You can watch the entire replay on LinkedIn here. And remember to pass this along to your team because it's a discussion that deserves to keep going.