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Five Reasons Your Middle Managers May Be Struggling

As businesses look to scale their operations, the strength of middle management is a critical success factor. In a recent national survey of ed-tech companies, 57% of C-level Executives indicated that their middle managers’ lack of experience was an obstacle to growing the business. When middle management struggles, it requires the C-level team to spend their time managing operational tasks, rather than managing the business. Below are five potential reasons your middle managers could be struggling:


They are out of their depth

Whether they’ve been promoted internally or recently hired into the company, middle managers are finding themselves in the biggest job of their life. In fact, 66% of middle managers admitted that their role puts them in unfamiliar waters, according to the Ed-tech Leadership Collective survey. This means that they are often unable to draw upon past experience when encountering challenges and are less likely to be able to anticipate obstacles. Consequently, they require frequent assistance from their executive team to identify, analyze and solve business problems. As they gain more experience and contextual knowledge, this becomes less of an issue. However, building that individual “knowledge base” and independence can take time.

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They aren’t able to prioritize the work of their teams

One of the most important skills for managers at every level of the organization is the ability to accomplish the high-priority work while adjusting the scope and expectations for non-priority work. In high-growth ed-tech organizations—where the tasks often outpace the available resources—teams can quickly tailspin into feeling overwhelmed. When this happens, they frequently gravitate toward the easiest or least-stressful activities, rather than the ones most important to the business. Ultimately, this leads to upper management having to step in and untangle things. 

Improving teams’ ability to manage priorities begins with clearly and consistently communicating the company goals and priorities—and cascading those to the department level as necessary. When communicated effectively, company and departmental priorities become part of a playbook bringing clarity to how teams manage their work each day, where they allocate resources and which due dates can be rescoped versus those that must be kept. 


They are unable to delegate effectively 

When new managers make the transition from “rock star employee” to “first-time people manager,” one of the common obstacles they encounter is effective delegation. However, this is a challenge that hinders many leaders well into their management career. 

Middle managers are often reluctant to delegate due to concerns that their team members might not complete the task in the same way the manager would or that the work wouldn’t show the same level of quality. Sometimes managers continue to stick close to their comfort zone of the task-level work that earned them recognition as a high-potential employee. Some make the mistake of thinking it’s faster to do the work themselves, rather than train a team member and hand off the task. In other cases, middle managers bear the brunt of the extra workload themselves in order to spare their team, rather than make the hard decisions about which tasks need to be rescoped or canceled. In all of these cases, there’s an underlying failure to embrace one’s role as a manager—to work “on” the business rather than work “in” the business. 


They’re not getting consistent mentoring and feedback

Professional growth doesn’t occur in a vacuum. Mentoring and development of team members require managers to dedicate the time to listen, provide feedback and offer coaching. This is proving to be increasingly difficult, particularly with so many companies operating in a hybrid or fully remote environment. Those “organic” moments of feedback and job shadowing occur much less frequently. In fact, the Ed-tech Leadership Collective found that only 18% of C-level Executives thought their high-potential managers were receiving enough mentoring and support. Middle managers tended to agree, with approximately two-thirds (63%) of them stating that they receive feedback regarding their job performance only a few times per year, if at all. Those who received feedback at least monthly were more likely to find the feedback helpful (77%), compared to those receiving feedback less frequently (51%).


They lack outside perspective on their work 

As a middle manager, it can be difficult to recognize one’s own blind spots and identify gaps in programs and processes. This can be especially difficult if you seldom receive feedback or if you are one of only a few people working within your functional area. This kind of isolation can slow the pace of innovation as well as affect job satisfaction. Some managers have described this effect as feeling like they are in an “echo chamber.” 

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For those leaders who are feeling “out of their depth” or are struggling to prioritize and manage their team’s work, an outside perspective of peers can be invaluable. According to the Ed-tech Leadership Collective survey, an overwhelming majority (91%) of middle managers indicated that they wanted more insight into best practices and access to outside perspectives from peers doing the same job at other companies. This kind of outside perspective can help lighten the burden for executive leaders, who have very limited time to mentor and share best practices with their middle managers. 


As companies grow, the success of middle managers becomes critically important. Yet, many organizations under-invest in the development of these key team members. When middle managers struggle, it is often due to a lack of information and feedback, as well some underlying skill gaps associated with decision-making, cross-departmental communication and time management. 

Given the limited amount of time most executives have, it is not surprising that most C-level Executives and middle managers identified professional peer group and executive coaching as their preferred methods, according to the Ed-tech Leadership Collective survey. Peer groups and executive coaching both offer middle managers a rigorous structure, ongoing feedback from mentors or peers, and outside perspectives on one’s professional strengths and areas for improvement. Regardless of the method used, it’s important that C-level Executives put a greater emphasis on the success of their middle managers in order to achieve company goals. 


Collin Earnst is founder and managing partner of the Ed-tech Leadership Collective, an organization focused on helping high-potential employees achieve the professional breakthroughs necessary for businesses to succeed. The Collective provides executive coaching as well as professional peer groups designed specifically for high-potential ed-tech employees at key points in their career.