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Written By
Melissa Chua

Middle management challenges are tough. Here are 3 and how to overcome them

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Table of Content

Table of Contents

Middle management positions are undoubtedly one of the toughest milestones in any career. According to the Harvard Business Review, middle managers, who are defined as employees managing one to six team members, are nearly half as satisfied with their jobs than senior executives.

As a middle manager, you are not only responsible for supporting employee growth and overseeing day-to-day operations, but also required to account to higher management for your team’s performance and KPIs. Met with middle management challenges, you end up with one foot on both sides of the organisational dynamic. This vertical code-switching inevitably takes a mental and emotional toll.  

To stay resilient, it’s important to put your own oxygen mask on first when it comes to mental wellbeing and self-care. But beyond that, what else can you do to better deal with these tricky situations?

Tackle middle management challenges with a coaching mindset

middle management challenges

Here’s the answer up front: the key to successfully tackling middle management challenges is to have a coaching mindset. And yes, this works for both managing up and managing down. 

Today, Shyamala Sashikumar is an ICF-certified PCC coach with Intellect. But prior to this, she was a professional in the financial services industry. With over 25 years of experience working in a corporate environment, she knows a thing or two about the pressures and challenges of being a middle manager. Her most important revelation? 

“I wish I had known then what I know now about coaching,” says Shyamala. “I realise in hindsight that I was applying a lot of coaching concepts in my working and management style, but they were less concrete than what I know now.”

Compared to managers with a traditional manager mindset, one with a coaching mindset focuses on inclusive and collaborative problem-solving. Rather than dictate solutions, they work together with their team to dissect problems, map out solutions, and evaluate risks and rewards. It’s the antithesis of micromanagement and gives employees greater accountability, ownership, and commitment over their personal performance. 

This mindset also works with managing upwards. You’re not just a sometimes supervisor, sometimes subordinate—you’re a collaborator who understands what’s important to your boss, and actively works together with them to support their success and goals. 

“Having a coaching mindset is important to ensuring that the conversations you have [with your team and your higher-ups] aren’t just transactional, but transformative,” Shyamala explains. “Otherwise you’ll be missing out on that emotional connection which is so critical to improving resilience, motivation, and productivity at work.”

For a few of the middle management challenges you may face in the workplace, here’s some advice on how a coaching mindset may help. 

3 recurring middle management challenges

1. Relaying potentially unpopular decisions

It’s often the ultimate test of leadership to communicate difficult top-down decisions to your team. But just as important as relaying information is listening to your team’s concerns.  

Uncertainty is usually what triggers fear, so be sure to mitigate this by being as honest as possible. Focus on hope and possibilities without sugar coating or glossing over difficult issues. “The only way to build trust is through transparency,” asserts Shyamala. “With trust, you’ll be in a better position to get your team comfortable with whatever change is coming their way.”

Work together to address any anxieties and approach conversations with compassion and empathy. Using a coaching model like F.U.E.L. or C.L.E.A.R. can help keep the conversation focused on constructive, actionable next steps so that employees don’t get stuck in the fear loop. 

2. Handling conflicts

While most conflicts can and should be handled between employees themselves, there may come a point when you need to step in as their manager. This is especially so if the conflict is indirectly affecting everyone else, or threatens workplace culture and morale. 

Should you get involved, listen more than you speak. Only through listening will you be able to understand the heart of the matter and hopefully reach some sort of resolution. 

More importantly, know that a resolution doesn’t necessarily have to look like an agreement. Most times, respectfully agreeing to disagree is as good as it gets, says senior HR specialist Megan Moran

“Employees should acknowledge there is a difference of opinion or approach, and come up with a solution together on how to move forward,” says Moran. As a middle manager, helping them get to that point requires a coaching mindset that prioritises active listening and collaboration over being right. 

3. Addressing underperformance

Leading a dynamic team means operating with a growth and talent mobility mindset. While in the past, managers may look at an underperforming employee as someone to push, drive, or dangle a carrot in front of, the modern manager would do better to empower, train, and motivate through coaching and constructive feedback. 

Each employee has their unique strengths and weaknesses, so rather than dictating a solution, ask what’s holding them back, what obstacles they’re facing, and what would help them better succeed and thrive at work. 

Essential to this is building a culture of psychological safety in the workplace, so that employees feel comfortable sharing personal challenges. “Never make people fear making mistakes, because fear puts people on the defensive, makes them defiant, and stifles growth,” shares Shyamala. 

Coaching as a neutral pillar of support

Middle management challenges make it hard to strike the balance between approachability and authority. While some middle managers are comfortable with vertical code-switching between high and low-power mindsets, others will need help melding these two seemingly incompatible aspects into one coherent identity. 

A coach could be the perfect resource for helping you address middle management challenges while supporting your team’s mental wellbeing and motivation at work. Coaches also provide a third-party alternative for employees who may be uncomfortable sharing personal challenges with their managers.

Find out more about working with Intellect to support your company’s coaching and mental health needs. 

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