Leadership in the Middle: Coaching for Culture Keepers

Let’s get one thing straight: your middle managers are not just line items on an org chart. They’re not just project shepherds or performance review fillers. They are the bridge. The buffer. The nerve center. The culture keepers. And right now, many of them are barely hanging on.

In this episode of What’s the DEIL?, we talk about what it really means to lead from the middle and how organizations consistently overlook the most pivotal people in their company’s ecosystem. If you want to see real transformation in your workplace culture, you have to start here.

What Exactly Is Middle Management?

Titles vary, but middle managers typically live between your senior leadership team and the front lines. Think: manager, senior manager, assistant director, director. They’re responsible for translating strategy into action. For supporting direct reports while answering high-level KPIs. For keeping the machine running and the people sane. That’s a tall order. And often, an impossible one—especially when they’re expected to do it without tools, training, or time.

These are the people caught in the squeeze: fielding upward pressure from leadership and downward pressure from employees. It’s one of the most complex roles in a company. And yet, we rarely invest in their development until it’s too late.

The Disconnect from the Top

One of the most striking patterns we’ve seen across hundreds of assessments is this: senior leaders often have no idea how much pressure their managers are under.

That disconnect usually happens for two reasons:

1. Distance from the work. The higher up you go, the more abstract the problems become. Executives tend to speak in strategy and outcomes. Middle managers speak in deadlines, interpersonal dynamics, resource gaps, and competing priorities. That’s not just a communication gap—it’s a system failure.
2. Nostalgia bias. Leaders who were once managers themselves may assume things haven’t changed. Spoiler alert: they have. Business moves faster. Expectations are higher. Teams are more dispersed. Employees have different boundaries and needs. What worked in 2005 doesn’t work in 2025. Period.

When leaders are out of touch with the realities of middle management, they make well-intentioned but tone-deaf decisions. They roll out initiatives without asking who will carry the burden. They launch new tools or policies without involving the people who have to explain them and enforce them. This is how burnout builds. And how culture breaks.

Culture Doesn’t Start at the Top

Let’s go ahead and say it: Culture doesn’t live in the C-suite. It lives day-to-day. That means your middle managers are your cultural heartbeat. They’re the ones delivering feedback. Facilitating meetings. Mediating team conflict. Translating change. Modeling the behaviors you claim to value in your mission statement.

When they’re misaligned, disengaged, or unsupported, your culture slips. Not because they don’t care but because they’re out of fuel.

So if you’re trying to fix your culture through memos, company-wide town halls, or another glossy campaign—stop. Your culture will not change unless your middle managers are equipped and empowered to lead that change.

The Training Problem

One of the most consistent themes we hear in our interviews and assessments is this:

“I was just thrown into this role. No one trained me to manage people.”

This isn’t a problem of intent. It’s a problem of systems. Organizations tend to promote their best individual contributors into management roles and then abandon them.

They assume great performance translates into great leadership. It doesn’t.

Managing people is a skill. Giving feedback is a skill. Navigating conflict is a skill. Delegating, developing, motivating, managing up, managing down, these are skills.

You don’t hand someone a wrench and expect them to know how to fix a car. So why do we expect people to just “figure out” management?

Why Coaching > Training

It’s time to reframe how we develop our managers. Not with a one-time webinar or generic handbook. With coaching.

Coaching isn’t about correcting bad behavior. And it’s not just for executives.

It’s a developmental partnership designed to help people build self-awareness, understand their leadership style, and navigate challenges in real time.

And it’s not just for the few. Coaching can be scaled. Whether it’s through one-on-one engagements, group sessions, or platforms like Cloverleaf that offer dynamic, daily insights into leadership styles and team interactions—there’s a model for every company size and budget.

The key is consistency. Coaching provides middle managers with the space to think, reflect, and adapt. It also gives them a mirror, a place to understand how they show up, and how they can lead more effectively.

Stop Winging It. Start Listening.

If you’re not sure where to start, begin by listening.

Conduct a real culture assessment, one that includes quantitative surveys and qualitative data. Ask your middle managers what’s working, what’s not, and what support they actually need.

Don’t wait for a turnover spike or a high-profile HR complaint. By then, your culture is already bleeding.

Middle managers aren’t your problem. They’re your biggest opportunity. But only if you give them what they need.

What Managers Actually Need

Here’s what we know works:

• Clarity. Clear expectations, clear goals, and clear measures of success. Vague mandates don’t scale.
• Consistency. Ongoing training and development that’s baked into their growth—not optional or extra.
• Coaching. Not just once. Not just when there’s a problem. Consistent opportunities to be supported and challenged.
• Community. Middle managers are often isolated. Creating peer coaching or affinity spaces helps normalize the challenges and reduce the stigma of “not knowing.”
• Time. Stop loading managers with so many individual contributor tasks that they can’t actually manage.
• Trust. Let them experiment. Let them lead. Let them make a few mistakes along the way.

Your Culture Is Only as Strong as Your Middle

Let’s be honest. Most of your big ideas? They’re not going anywhere unless your middle managers are behind them.

They’re the ones who translate your mission into Monday morning meetings. They’re the ones who make or break your employee experience. They’re the ones who feel the culture most deeply and hold the most power to shape it.

So if you’re ready to build a stronger, more resilient organization, don’t start at the top. Start in the middle.

And if you’re not sure how? We’re right here.

Connect With Us

If you found this discussion compelling, we invite you to connect with us further. Here are some ways to stay in touch:

• Follow Natalie Norfus on LinkedIn
• Follow Shanté Gordon on LinkedIn
• Book a consultation with The Norfus Firm
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