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Always On, Always Changing: The Tech-Driven Metamorphosis of Management

Navigating the shift from email overload to AI assistance in the modern workplace

Management in the workplace is complex to say the least. As a long-time manager and now founder of an AI company, I've seen firsthand how technology has reshaped the management landscape.

I often cringe at memes like below1 that pit managers against leaders, as if they're mutually exclusive. In my experience, great management and leadership are two sides of the same coin—both essential and complementary in today's fast-paced, tech-driven workplace. As I’ve written about leadership in my last blog post, I figured it would be worthwhile to discuss management as well, and why good management is more important than ever as technology continues to shape the way we work.

Management & Leadership are Not Mutually Exclusive

Introduction

In the ever-shifting landscape of business, few aspects have undergone as dramatic a transformation as workplace management. From the advent of the internet to the rise of today’s artificial intelligence, each technological wave has reshaped how leaders guide their teams, make decisions, and drive organizational success.

As we stand on the cusp of a new AI-driven era, it's crucial to reflect on this journey. We've witnessed management evolve from the early days of email revolutionizing communication, through the always-on culture of the mobile age, to the recent seismic shift towards remote work catalyzed by a global pandemic. Each stage has brought its own set of challenges and opportunities, fundamentally altering the manager's toolbox and mindset.

Today, as artificial intelligence begins to augment human capabilities in unprecedented ways, we find ourselves at another inflection point. The role of the manager is being redefined once again, raising questions about the future of leadership, decision-making, and the very nature of work itself.

In this article, I'll trace the arc of this technological evolution and its impact on management practices. I’ll explore how the internet first broke down information silos, how mobile technology blurred the lines between work and personal life, how the pandemic forced a reevaluation of traditional office-centric models, and finally how AI is now promising to elevate managerial effectiveness to new heights.

By understanding this journey, we can better prepare for the challenges and opportunities that lie ahead. After all, in the world of modern management, the only constant is change. Let's dive in and explore how technology has reshaped—and continues to redefine—the art and science of management in the workplace.

The Internet Era: Revolutionizing Communication and Information Flow

The dawn of the internet age marked a pivotal moment in the evolution of workplace management. As organizations began to harness the power of digital connectivity, managers found themselves at the helm of a communication revolution that would forever change how businesses operate.

Email: The Communicate Catalyst

The early internet brought with it a brand new way to communicate: email.  Deceptively simple, people could now easily chat asynchronously anywhere in the world. Managers, once constrained by the limitations of phone calls and physical memos, could now instantly disseminate information to their teams, regardless of location or time zone. This speed brought both benefits and challenges:

  • Faster decision-making: Issues that once took days to resolve could now be addressed in hours.

  • Increased productivity: Quick exchanges of information streamlined workflows.

  • Information overload: Managers had to develop new skills to prioritize and manage the influx of digital communication.

I remember from my internship back at Apple in 2006, getting instant feedback and input from my own manager. It was a magical experience that could be used for good or bad, depending on the timing & usage.

While the power of asynchronous communication enables 24/7 messaging, it’s incredibly important to remember there’s a real person on the receiving end of these messages. 52% of Americans check their email before & after typical work hours2 .  This leads to higher stress and exhaustion—and managers especially need to be mindful of this.  While I’ve been fortunate having reasonable managers who don’t expect responses immediately, it’s still incredibly important to note that most employees will always try to respond to their manager’s message quickly.

Pro Tip: Even macOS (finally!) has a “send later” option.  Managers: use this to write email on your own time and ensure it’s sent during business hours, unless the message is absolutely critical (in which case why are you using email?)

The Mobile Revolution: Always-On Leadership

As smartphones and tablets became ubiquitous, the nature of work underwent another seismic shift. The mobile revolution brought with it unprecedented connectivity and flexibility, but also blurred the lines between professional and personal life. For managers, this new era presented both opportunities and significant challenges.

Smartphones: The Double-Edged Sword

The advent of smartphones fundamentally altered the expectations of availability and responsiveness in the workplace:

  • Constant Connectivity: Managers could now access work emails, documents, and communication platforms 24/7 from (almost) anywhere, enabling quicker decision-making and problem-solving.

  • Increased Productivity: The ability to work from anywhere allowed for greater flexibility in managing tasks and teams.

  • Work-Life Imbalance: The always-on culture led to increased stress and burnout, as the boundaries between work and personal time eroded.3

Managers faced the difficult task of balancing the benefits of increased connectivity with the need to protect their own and their team's well-being. This required developing new skills in time management, priority setting, and fostering a healthy work culture in an always-connected environment.  Good managers set boundaries and enforced reasonable expectations—while bad managers took advantage of employees even more.

I remember the day I got my first work-issued iPhone. It felt like a superpower —I could respond to urgent issues from anywhere, anytime! But it didn't take long to realize this “superpower” came with its own kryptonite: the expectation of 24/7 availability.

During my own managerial journey, I learned the hard way that “do as I say, not as I do” doesn't cut it in the always-on mobile era. One night, after sending the factory emails at 10 PM (again), I realized I was part of the problem. So, I decided to lead by example: I started by turning on 'do not disturb' mode on my devices and actually sticking to it. I alerted my team that I'd be unavailable during certain times - even blocking off “unavailable” time on my calendar. And here's the kicker: I actually adhered to it. No sneaking away to check messages (okay, maybe once or twice at first but I’m only human). The result? Not only did my stress levels plummet, but my team started following suit. Have you tried setting similar boundaries? If not, I challenge you to give it a shot for a week and see what happens. You might be surprised at the positive ripple effects it creates in your team's work-life balance.

Managers: Try setting your own time-blocked boundaries and lead by example—it’s quite effective.

With the ability to work anywhere, it was only a matter of time until teams became more distributed—an event catalyzed by the COVID-19 pandemic.

Pandemic-Driven Hybrid/Remote Work: A New Paradigm

At home, on the road, on vacation—working from anywhere is great, isn’t it?

The global COVID-19 pandemic catapulted organizations into an unprecedented experiment in remote work. What was once a growing trend became an immediate necessity, forcing managers to rapidly adapt their leadership styles and strategies. This seismic shift brought with it a unique set of challenges and opportunities, reshaping the landscape of workplace management.

The Great Remote Work Experiment

Almost overnight, managers found themselves leading teams scattered across various locations:

  • Rapid Technology Adoption: Organizations scrambled to implement video conferencing and collaboration tools at scale.4

  • Home Office Setups: Managers had to ensure team members had the necessary equipment and environment to work effectively from home.5

  • Mental Health Concerns: The isolation and stress of the pandemic added an extra layer of complexity to team management.

This sudden transition tested managers' adaptability and crisis management skills like never before.

Focus on Results Over Presence

With traditional office-based oversight no longer possible, managers had to shift their focus:

  • Output-Based Evaluation: Performance metrics had to evolve to prioritize results and outcomes over hours worked or physical presence.

  • Clear Goal Setting: The importance of setting clear, measurable objectives became even more critical in a remote environment.

  • Trust-Based Management: Micromanagement became not just ineffective but impossible, requiring a new level of trust in employees.

This shift challenged long-held assumptions about productivity and work styles, forcing many managers to reevaluate their leadership approaches. Unfortunately, I know many managers who kept trying to micro-manage during this time and simply caused burn-out of their teams (checking in every few hours doesn’t work very well and is just irritating).

Managers: Attempt to build a culture of trust & psychological safety—teams are happier, more efficient, and feel empowered at work; plus, this opens the door to members getting work done on their own schedule, from wherever they can effectively do their job.

Maintaining Team Cohesion and Culture

Building and maintaining a strong team culture became one of the biggest challenges in remote work:

  • Virtual Team Building: Managers had to get creative with online social events and team-building activities. (Anyone else remember Donut?)

  • Onboarding New Employees: Integrating new team members without in-person interactions required innovative approaches.

  • Preserving Company Values: Ensuring that organizational culture remained strong without a physical workplace became a key priority.

This challenge required managers to become culture advocates, actively working to reinforce company values and team spirit in a virtual setting. Building culture is hard enough when teams are co-located, but doing it well virtually, was insanely tough.

Though new tools were created to enable us to work more effectively in remote and hybrid work environments, we didn’t get better at communicating—we simply got more of it.

Fortunately, a technological breakthrough might just let us improve the way we manage, by leveraging LLM’s and agents to complement management.

The AI Age: Augmenting Managerial Capabilities

As we step into the era of artificial intelligence, managers find themselves on the cusp of another transformative shift. AI technologies are not just changing the tools at a manager's disposal; they're redefining the very nature of managerial work. This new frontier offers unprecedented opportunities for enhancing decision-making, improving efficiency, and fostering employee development.

AI-Powered Analytics: Data-Driven Decision Making

One of the most significant impacts of AI on management is in the realm of data analysis and decision support:

  • Predictive Analytics: AI can process vast amounts of data to forecast trends, helping managers make more informed strategic decisions.

  • Performance Insights: Advanced analytics can provide deeper insights into individual and team performance, enabling more targeted interventions and support.

  • Risk Assessment: AI algorithms can identify potential risks and challenges before they become critical issues, allowing for proactive management.

I strongly believe in these advancements which is why I founded Attrove. Let’s create innovative ways to leverage technology to improve employee’s (and manager’s) lives.

Automation of Routine Tasks: Focusing on Strategic Work

AI is increasingly capable of handling routine administrative tasks, freeing up managers to focus on more strategic activities:

  • Report Generation: Automated systems can compile and format routine reports, saving managers significant time.

  • Communication Prioritization: Attrove can sort and prioritize emails, chats, and meetings, helping managers focus on the most critical communications.

By offloading these time-consuming tasks, managers can dedicate more energy to high-value activities like strategy development, mentoring, and innovation.

The integration of AI into management practices represents both an exciting opportunity and a significant challenge. As these technologies continue to advance, they promise to amplify managerial capabilities in ways we're only beginning to understand. However, the core of effective management— leadership, empathy, and strategic thinking—will remain uniquely human domains.

As the founder of Attrove, I'm excited about AI's potential to transform management. But I'm also acutely aware that AI is a tool, not a replacement for human judgment. The best managers will use AI to handle routine tasks, freeing them to focus on what truly matters: inspiring, guiding, and developing their team members.

Conclusion: Embracing the Ever-Evolving Landscape of Management

Fire-pit circles to virtual meetings

As we've journeyed through the technological transformations that have shaped workplace management, one thing becomes abundantly clear: adaptability is the hallmark of effective leadership. From the dawn of the internet era to the rise of AI, each wave of innovation has brought its own set of challenges and opportunities, fundamentally reshaping the manager's role.

We've witnessed how the internet revolutionized communication and information flow, how mobile technology blurred the lines between work and personal life, and how the pandemic forced a global experiment in remote work. Now, as we stand on the brink of an AI-augmented future, we find ourselves at yet another inflection point in the evolution of management.

But amidst all this change, the core essence of great management remains constant: the ability to inspire, guide, and empower people. As we look to the future, the most successful managers will be those who can harness the power of new technologies while preserving the human touch that lies at the heart of effective leadership.

The journey of management evolution is far from over. As AI and other emerging technologies continue to reshape the workplace, new challenges and opportunities will undoubtedly arise. How will managers balance the efficiencies of AI with the need for human creativity and empathy? What new skills will be required to lead in an increasingly automated world? And how will the very concept of work itself continue to evolve?

These questions and more await us on the horizon. For managers and leaders willing to embrace change, stay curious, and continue learning, the future holds endless possibilities. The next chapter in the story of management is yet to be written—and it promises to be the most exciting one yet.

Summer 2006 - Me Interning at Apple (Building IL3)

As I reflect on my journey from a wide-eyed intern marveling at email to a founder developing AI tools for managers & leaders, one thing is clear: the essence of great management transcends technology. While tools and techniques evolve, the ability to inspire, guide, and empower people remains at the heart of effective leadership.