A Millennial Manager’s Realities & Guide To Managing Both Up and Down [W&S 61 ft Henry Suryawirawan]

In a recent episode of the Wise & Shine podcast, hosts Reggie (a.k.a. Your Chief Financial Coconut) and Dawn (SG Budget Babe) welcomed special guest Henry Suryawirawan, host of the acclaimed Tech Lead Journal podcast, is unpacking practical crisis response strategies. Henry has interviewed over 150 tech leaders through his podcast. His insights come from years of experience at the helm. 

The conversation revolved around the role of middle managers and the challenges they face in an era of technological advancements and organizational restructuring.

As technology optimizes workflows, many wonder if managers will become obsolete. Henry argues: their responsibilities have simply changed – and adapting is key to surviving the turbulent times ahead.

The Future of Middle Management in the Tech Age

Challenges Faced by Middle Managers:

One of the primary struggles is being caught in the middle, as they are accountable to both higher-level executives and their teams. According to Henry, clarity and alignment are critical. “In big companies, goals and KPIs are set broadly, but different teams have varied priorities and track progress differently. Executing a cohesive vision becomes muddy.”

Consistency also suffers. Said Henry, “targets keep changing, sometimes every few months. Imagine pivoting a ship – it can’t spin on a dime. Changes require gradual, aligned shifts.” Resource constraints pose issues too. Without enough “people, skillsets, or time to reasonably hit targets,” success seems doomed from the start.

“One big struggle is selling new directions to your team.” While leadership provides the “vision,” motivating others requires “shopping ideas, getting buy-in from detractors.” Simply announcing changes leaves many opposed.

Henry adds, “You must communicate why the shift matters and where it solves real problems. Listen before deciding you alone have the answers.” Change management also takes constant reinforcement: “Over-communicate through multiple channels over time.” Without consensus, managers bear the brunt of failed expectations.

The Role of Middle Managers:

Middle managers often find themselves responsible for executing top-level initiatives and goals while managing their teams’ day-to-day operations. They must bridge the gap between the visionaries at the top and the individuals responsible for practical execution. This delicate balancing act demands significant art and skill from middle managers.

Middle managers bear the responsibility of translating top-level directives and communicating them effectively to their teams. At the same time, they must navigate the pressure from both above and below, acting as a shield between senior management and their teams.

The conversation explored the three primary aspects of middle managers’ work. First and foremost is team management, which involves maintaining a high level of engagement and involvement with their teams. Unlike senior management, middle managers have a more hands-on approach, working closely with their teams on a daily basis.

Managing key performance indicators (KPIs) was another crucial aspect discussed. Middle managers play a pivotal role in driving KPI success and ensuring alignment with the organization’s goals and vision. However, the challenge lies in the clarity and alignment of KPIs, particularly in larger companies with multiple departments or product lines.

The Future of Middle Managers:

As the conversation concluded, the question lingered:
Is there still a need for middle managers in an ever-evolving technological landscape?
While technology may optimize certain tasks, middle managers remain crucial for bridging the gap between strategic vision and practical execution. Their ability to navigate complex organizational dynamics and lead teams is an invaluable asset.

How do middle managers future-proof themselves against flattening hierarchies?
Henry argued their role hasn’t disappeared – it has evolved. “Unless AI achieves human-level communication and collaboration, we’ll always need coordination at scale.” Where roles have streamlined, new opportunities have emerged.

As Dawn pointed out, cross-training creates multi-faceted employees less vulnerable to restructuring. Said Henry, the future lies not in job titles alone, but organizational structures that optimize flow and empower autonomy. Progress demands flexibility – and those who adapt will endure.

In a tech-driven world, perhaps the most valuable asset remains human expertise applied creatively. With open minds and efficient teams, even traditional managers may discover their place is secure for years to come.

Throughout the podcast, Henry and the hosts emphasized the importance of middle managers in organizations and the unique challenges they face. The role of a middle manager is not only about making decisions but also about effective communication, team management, and ensuring successful execution of key initiatives. 

You can check their full interview on Wise & Shine, Episode 61 on Spotify, YouTube, Google podcast or Apple podcast for their conversation on managing expectations from higher-level executives. The role of a middle manager is not only about making decisions but also about effective communication, team management, and ensuring successful execution of key initiatives.

Key Takeaways:

  1. Middle managers serve as a crucial link between top-level executives and teams.
  2. Challenges faced by middle managers include pressure from both above and below, managing team expectations, and ensuring successful execution.
  3. Middle managers play a vital role in driving KPI success and aligning organizational goals.
  4. Effective communication and team management are essential skills for middle managers.
  5. Despite technological advancements, the role of middle managers remains indispensable in bridging the gap between strategic vision and practical execution.

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Learn more from Henry on what are the 3 structures to crisis management to upskill or as a manager

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