Managers Are Stuck: The Missing Middle of Engagement

2025-07-03  • 37 min

Managers Are Stuck: The Missing Middle of Engagement with Matt Sunshine

Culture Over Coffee

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Middle managers are the critical link between leadership and employees...but many of them feel disengaged, unsupported, and overwhelmed.  

In this episode, Matt Sunshine, CEO of The Center for Sales Strategy, joins Beth to discuss why managers are struggling to stay engaged and how that impacts the teams they lead. 

Matt has some amazing takeaways, like: 

• Why the way in which companies “shift the goal posts” in how they measure success makes middle managers feel as though they can never win. 

• How when middle managers are disengaged, it spreads like wildfire, transforming employees who were previously “all in” into people who clock in and check out. 
• And, finally, why, if managers aren’t involved in navigating the future of your organization, you’ll soon be in a boat that’s rowing in circles

The Disengagement Spiral: What’s Driving It?

Matt first shared that the data from ENGAGE 2025: The Company Culture Report, while disheartening, wasn’t surprising. In his work with companies across the country, he hears similar frustrations from mid-level leaders again and again.

One of the biggest drivers? A lack of clear direction.

When middle managers don’t understand where the organization is headed (or why it's going there) changes feel chaotic instead of strategic. “It’s like being in the back seat of a car with a blindfold on,” Matt said. “Every turn feels more jarring when you can’t see what’s coming.”

Another issue is the ever-shifting definition of success. When metrics and goals change frequently without context, it creates a moving target effect. Managers feel like Charlie Brown trying to kick a football that’s constantly being pulled away.

The result? Disengagement spreads.

Managers who were once “all in” begin to check out, doing just enough to meet expectations but no longer offering the discretionary effort that truly drives business success.

When the Glue Weakens

Middle managers are the vital link between leadership and employees. When they feel disconnected or undervalued, the entire organization suffers.

As Matt explained, disengaged managers either leave (leading to costly turnover) or stay and quietly pull back, creating disengaged teams in their wake.

These changes may not show up in metrics right away, but the long-term impact on morale, productivity, and retention is profound. Matt emphasized that disengagement can lead previously loyal employees to start fielding recruiter calls, watching the clock, and measuring every task against their paycheck.

The “Missing Middle” in Strategic Planning

So why are middle managers feeling left behind? Matt believes much of it is unintentional. Leadership often doesn’t have a structured way to include managers in planning conversations or they’re concerned about wasting managers’ already limited time with unclear or unproductive meetings.

But excluding managers from big-picture strategy is a costly mistake. Not only does it deprive organizations of crucial insights, it makes it nearly impossible to align teams across departments. “If managers aren’t involved in setting the direction,” Matt said, “you’ll end up with a boat rowing in circles.”

The best organizations, he added, have systems for including managers meaningfully; inviting them into the process before decisions are finalized and empowering them to lead with clarity.

Control What You Can: How Managers Can Regain Their Power

Beth and Matt also explored what managers themselves can do even when they feel burned out or disempowered.

Matt’s advice: Control your culture.

Even when you can’t fix everything at the organizational level, you can still build an exceptional team culture.

This might mean involving your team in setting short-term goals, being transparent about challenges, or recognizing people regularly for embodying company values.

One manager Matt spoke with even acknowledged her company's poor Glassdoor reviews. She then made it her mission to ensure her team was a place people wanted to be. That kind of leadership, Matt said, is powerful and impactful.

The Hidden Power of Recognition, Values, and Voice

Throughout the episode, Matt emphasized the importance of culture cues like core values and recognition. Rather than defining values in vague corporate speak, he recommends surfacing real-world examples of how values like quality, integrity, and responsiveness show up on the job. Then, celebrate those moments.

Recognition is one of the most effective tools for reinforcing the right behaviors.

And for senior leaders looking to show support today? Start small. Ask your managers for their opinions. Involve them in decisions you haven’t fully made yet. "People won’t see that as a burden,” Matt said. “They’ll feel valued.”

A Leader’s Personal Brand Matters Too

Interestingly, Matt highlighted that leaders at every level (especially managers) should think about their individual brand within the company. Just as companies have employer brands, every manager builds a reputation through their actions, communication, and team culture. And that brand can be a game-changer in attracting and retaining talent.

“Even if the company isn’t known for being a great place to work,” Matt said, “if someone gets the chance to work for a great manager, they’ll take it.”

The First Step? Start With Yourself

To close out the conversation, Beth asked Matt where CEOs and other C-suite leaders should start if they want to improve engagement. His answer? Start with yourself.

If senior leadership doesn’t treat engagement as a top priority, no one else will. Only then should leaders turn their focus to empowering and involving middle managers—giving them the clarity, resources, and trust they need to thrive.

“Success leaves clues,” Matt said. “And the best organizations out there? They have strong cultures and high engagement. That’s no coincidence.”