Middle Management: Stuck Between a Rock and a Hard Place

June 6th, 2023 – SkillCycle

In this article, we’ll explore how you as a leader can prioritize the development of your managers, making sure they are gaining the skills and experience they need to grow with your company, including: 

  • How middle managers can drive their careers forward
  • The three Cs of effective decision-making
  • Two ways managers can grow their self-awareness 
  • Why leaders must learn to provide regular feedback
  • How to embrace transparency in communication
  • How leaders can help middle management get unstuck


Middle managers find themselves in a constant balancing act, caught between multiple responsibilities. They have to handle diverse teams, tackle administrative tasks, and nurture the growth of their subordinates—all at the same time. It’s no easy feat, and these challenges impact not only the managers themselves, but your entire organization

This balancing act is hindering manager productivity and driving up stress levels. As a result, managers are 46% less satisfied with their jobs than senior executives and feel they have struggled more than twice as much, according to Harvard Business Review.

“They’re stuck, caught between the daily administration of managing people and administrative tasks—and more meetings than they know what to do with!” says Kristy McCann Flynn, Co-founder and CEO of SkillCycle.

Middle management roles impact high-stakes areas of the workplace such as engagement, retention, productivity, and goal-setting. Yet, many middle managers end up handling non-managerial work and wrestling with bureaucracy instead of focusing on one of the most vital tasks they could be doing—fostering talent, says McKinsey

“As long as middle managers are stuck, companies will be, too. Leaders can turn situations like this around, though. With the right coaching, you can help build your managers to be the future of your company that engages, retains, produces, and flourishes.” says McCann Flynn. 


How you can help your middle managers drive their careers forward

The world of work is changing, and managers are carrying more responsibility than ever, according to Gartner. Offering your managers training and learning opportunities to help round out their capabilities can go a long way toward furthering their performance and careers.

It is well known that building soft skills, self-awareness, and education helps managers excel, leading their teams and your organization as a whole to better performance. 

Helping your managers thrive and advance involves ensuring they understand their responsibilities and are equipped with the resources they need to remain engaged and effective in their roles.

Let’s walk through how ongoing training, coaching, and mentoring can reinforce the development of your managers’ skills. 


Developing the three Cs of effective decision-making

It’s a wise move to ensure the coaching you offer your middle management staff addresses the three Cs of effective decision-making. These have long been established as constructive conflict, consideration, and closure. 

Let’s break these down:

Constructive conflict: Embracing constructive conflict means actively involving team members in decision-making. It’s about encouraging diverse perspectives, sparking lively debates, and fostering creative problem-solving to find the best solutions.

Consideration: An essential aspect of effective decision-making is ensuring everyone’s viewpoint is genuinely considered. When all stakeholders feel heard and valued, they’re more likely to commit to and support the chosen solution.

Closure: Closure plays a crucial role in decision-making by ensuring everyone is on the same page. It means clearly defining when a project or initiative is considered “done,” checking if anything else needs to be addressed, and ensuring that everyone agrees on whether the outcome was successful.

When your managers have the support they need to master these soft skills, their ability to foster strong relationships within your organization will lead to an all-around uplift in worklife satisfaction and employee performance.


Empowering managers to grow their self-awareness

A high level of self-awareness comes from emotional intelligence and the ability to honestly assess your strengths and weaknesses. It’s one of the qualities that often separates high-performers from others in any organization. 

You can empower your managers to chart a path for their professional development by offering them opportunities to engage in self-assessment and seek insights from trusted colleagues through 360-degree reviews. This requires throwing out the tired, top-down model of performance reviews and investing in coaching that puts learning first.

A well-crafted development plan will help your managers focus on areas within themselves and their direct reports that require improvement, enhancing their capabilities and driving progress toward your company goals.


Why leaders must learn to provide regular feedback

“Feedback is a gift, and this is what check-ins are for,” says McCann Flynn. Lead by example and create a regular habit of checking in with your managers through regular one-on-ones and conversations outside of annual reviews, then encourage them to do the same with their teams. 

Why? How often you deliver feedback is incredibly important to your employees. For example, team members whose managers provide weekly, rather than annual, feedback are five times more likely to agree they are receiving meaningful feedback, three times more likely to say they are motivated to do outstanding work, and nearly three times more likely to be engaged at work, according to Gallup

For best results, advise your managers to keep feedback conversations informal, with a focus on an employee’s progress toward organizational goals. Assisting employees in outlining a clear path for progress shows them they can count on their manager as a guide toward the next milestones. This can strengthen trust in the managers on your team.


How to embrace transparency in communication

Effective communication skills are essential for managerial success. As a senior leader, you can equip your middle managers with the necessary training to develop their communication skills by offering access to learning-centered coaching.

Here’s an example. Coaching can help managers navigate challenges like organizational change, and provide them with the tools they need to communicate openly and honestly with their direct reports about what needs to be done in a given situation. Coaching will also help them learn how to paint a clear picture of how the company can benefit from the transition and get their teams on board.

Without the right coaching, managers may not feel confident in their ability to communicate the plan for moving forward and may struggle to ensure that their employees understand how their work contributes to broader corporate objectives.


How leaders can help middle management get unstuck 

As a leader, prioritizing the development of your middle managers can significantly impact many areas of your business. What skills would they need to perform more effectively in their roles today? What skills do you need them to have for the future growth of your company?

Invest in your middle managers by helping them develop leadership skills such as resilience, communication, learning agility, and self-awareness. “By doing so, you can help them step forward into leadership roles that enable the growth of themselves, their people, and their company,” says McCann Flynn.

If you’ve noticed these managers carrying too heavy a load, it might be time to pause and consider if they’re being offered the learning opportunities they need. 

Middle management isn’t doing it wrong; they’re just overwhelmed. Take things off their plate and give them the training they want with our People Success Operating System.


Subscribe to our newsletter