How Can Leaders Sustain a High-Performing Team?

The Squeezed Middle and the Key to Unlocking Potential.

The phrase “squeezed middle” usually conjures images of economic pressure, but in the world of organisational dynamics, it’s taking on a new, equally impactful meaning. We’re talking about your middle managers - the vital linchpins who bridge the gap between strategic vision and operational reality. Often, these individuals, despite their critical role in sustaining high-performing teams, are the most overlooked when it comes to receiving the support, skills, and empowerment they desperately need.

With my variety of work covering different sectors, I consistently see a pattern emerging, particularly in SMEs, of a disconnect between the strategic aspirations of senior leadership teams and the operational reality on the ground. This disconnect often stems from a lack of focus on developing and empowering middle management, leading to a host of unintended consequences that stifle growth, innovation, and ultimately, high performance.

The Unseen Burden of the ‘Embedded’ and the ‘Excellent’.

Consider your middle managers. They often fall into one of two categories, both of which present unique challenges.

Firstly, you have the “embedded” managers. These are individuals who have been in their roles for a significant period. They know the ropes, they’re deeply ingrained in the company culture, and they’re often highly competent in their day-to-day tasks. However, precisely because of their long tenure, they may be less inclined to seek support or admit when they feel out of their depths. They’ve perfected their routines, perhaps even adopting old habits that no longer serve a dynamic environment, and the idea of asking for new training or a different approach might feel like an admission of weakness. This can lead to them silently struggling with evolving leadership demands, unable to adapt to new team dynamics or strategic shifts.

Secondly, and increasingly common in fast-growing SMEs, are those who have “excelled” in their previous, non-managerial roles and have been promoted into middle management as a reward for their individual brilliance. While their expertise and dedication are undeniable, excelling as an individual contributor is a vastly different skill set from leading and developing a team. Without adequate training in areas like delegation, coaching, conflict resolution, or performance management, these new managers can quickly feel overwhelmed. They may revert to doing the work themselves, believing it’s quicker or better, rather than truly empowering their teams. It’s also known human behaviour to revert to comfort zones when busy or under pressure (which I’ve covered in a previous post) and this is seen time and again when under-skilled managers are put to the test.

Both scenarios contribute to a significant bottleneck in the flow of productivity and innovation, putting immense pressure on these crucial individuals and ultimately undermining the very foundation of a high-performing team.

When Leaders Get “Stuck in the Weeds”: The Perils of Un-Strategic SLTs

This issue is further compounded when senior leadership teams, particularly in SMEs, are what we might term “unsophisticated” in their approach to operational management. This isn’t a criticism of their intelligence or business acumen, but rather a recognition that many entrepreneurial leaders, driven by passion and a hands-on approach, can struggle to let go of the operational reins. They often find themselves:

“Stuck in the weeds”: Instead of focusing on strategic thinking, market trends, and long-term vision, directors become embroiled in the day-to-day minutiae. This can manifest as micro-managing, constantly checking in on small tasks, or even directly undertaking work that should be delegated to their middle managers or even their teams. This not only saps their valuable time and energy, but also signals a lack of trust in their subordinates.

Prevented from being strategic thinkers: When leaders are bogged down in operations, they lose the capacity to think strategically. They become reactive rather than proactive, unable to fully seize opportunities or effectively navigate challenges. The company’s growth trajectory can plateau, and its competitive edge can dull as strategic foresight is replaced by tactical firefighting.

Unable to empower their teams to deliver: If directors are constantly in the weeds, it creates a trickle-down effect. Middle managers aren’t truly empowered, and neither are the employees beneath them. The message, however unintentional, is clear: “We don’t trust you to deliver without our direct oversight.”

The Cascading Impact: A Cycle of Disempowerment

This managerial style, where SLTs struggle to truly empower their middle managers, leads to a predictable and detrimental set of outcomes within the organisation. What happens is:

Employees want to be empowered, but are not able to take ownership:
Modern employees, especially the younger generations, crave autonomy and ownership. They want to contribute meaningfully and see the impact of their work. When empowerment is absent, or superficial, their motivation wanes. They see opportunities to take initiative but are constantly awaiting approval or instruction.

Leaders don’t delegate effectively:
A common symptom of “in-the-weeds” leadership is poor delegation. Tasks are either not delegated at all, or they are delegated without sufficient context, authority, or trust. This results in work being redone, missed deadlines, or a constant back-and-forth that wastes time and frustrates everyone.

Management is perceived as controlling:
When employees feel constantly overseen, or when decisions are routinely pulled back up the chain, it cultivates a perception of a controlling management style. This erodes trust, stifles creativity, and creates a culture of dependency rather than proactivity.

Employees stop thinking for themselves:
This is perhaps the most insidious outcome. When individuals are consistently told what to do, or when their initiatives are overridden, they learn to stop thinking for themselves. They start to wait for permission or to be told what to do: They become passive, waiting for explicit instructions before taking any action, and this dramatically slows down decision-making and innovation.

Combined, these outcomes all lead to a perception of lack of ownership and the cycle of disempowerment continues. The initial problem perpetuates itself. Directors see a perceived lack of ownership from their teams, which reinforces their belief that they must retain control. This, in turn, further disempowers the team, creating a vicious cycle that prevents the organisation from truly scaling and thriving.

Breaking the Cycle: Empowering the Squeezed Middle

So, how can organisations sustain a high-performing team when their crucial middle managers are so often caught in this “squeezed middle”? The answer lies in a conscious, strategic investment in their development and empowerment which we have covered in these steps:

1. Acknowledge the Gap: The first step is for SLTs to honestly assess their own operational involvement and recognise where they are “stuck in the weeds.” This requires self-awareness and a willingness to trust their teams.
   
   
2. Invest in Middle Management Development: Provide targeted training programmes for middle managers. This isn't just about leadership theory; it's about practical skills in effective delegation, coaching, feedback, performance management, and conflict resolution. For the "embedded" managers, this might involve refreshing existing skills and introducing new methodologies. For the "excellent" but junior managers, it's about foundational leadership principles.
   
   
3. Foster a Culture of Psychological Safety: Create an environment where middle managers feel safe to ask for help, admit when they’re struggling, and experiment with new approaches without fear of retribution. This is crucial for both categories of managers to truly grow.
   
   
4. Define Clear Roles and Responsibilities: Ensure that the roles of SLTs and middle managers are clearly delineated. SLTs should focus on strategy, vision, and removing roadblocks, while middle managers are empowered to execute those strategies operationally, taking ownership of their teams’ performance.
   
   
5. Practice Intentional Delegation: SLTs must learn to delegate effectively, not just offload tasks. This means clearly communicating the "what" and the "why," providing the necessary resources, and trusting their managers to deliver the "how." It also means resisting the urge to jump back in when challenges arise, instead offering support and guidance.
   
   
6. Empower, Don’t Just Instruct: Shift from a command-and-control approach to one of empowerment. This means giving middle managers the autonomy to make decisions within their remit, encouraging initiative, and celebrating their successes. When they make mistakes, view them as learning opportunities.
   
   
7. Regular Coaching and Mentoring: Establish a system of regular coaching and mentoring for middle managers. This could be from senior leaders, external coaches, or even peer-to-peer mentoring programmes. Consistent support helps them navigate challenges and develop their leadership capabilities over time.

Sustaining a high-performing team isn’t just about recruiting top talent; it’s about nurturing and empowering every level of your organisation. By recognising the unique pressures on the “squeezed middle” and making a conscious effort to equip them with the skills and autonomy they need, Senior Leadership Teams can move out of the operational weeds and back into their strategic lane. This not only frees up directors to drive the business forward but also unlocks the full potential of their middle managers and, by extension, the entire workforce. 

The result? A truly empowered, engaged, and high-performing team ready to take your SME to the next level.

At Green Shed Talent, every project begins with a conversation, so do get in touch for a virtual or face-to-face coffee if you’re recognising any of this and want to empower your teams.