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Toronto, ON | London, UK

If you are making decisions based on information that is dated by 20 years, you’re not leading effectively.

Too often there’s a divide between high-level decision-making and the fine details that shape day-to-day operations—particularly in major programmes. As I’ve climbed the ladder, I’ve found value in staying closely connected to the grassroots of our operations—even if that means managing the occasional $1,000 invoice while overseeing a $100 million P&L.

While this may seem counterintuitive to some and like micromanaging to others, maintaining a tangible connection to the finer operational details of your business helps eliminate bureaucracy and sharpen decision-making. Leaders who invest the time to understand the day-to-day processes can identify inefficiencies and stay grounded, which ultimately leads to better leadership.

This year I was reminded of just how far removed I had become from the ground level. While I don’t expect to have all the answers that my team comes to me with, I do have the expectation for myself that I would at the very least understand the basics behind their question and how to direct them to the person who would be able to answer. When an individual on my team asked me a seemingly simple invoicing question and I had no way of answering or directing their query—I knew it was time to press the down button and get back to the ground floor.

Top of The Elevator Perspective

“All of that perspective you gain from the top of the elevator should be informed about what’s going on in the basement. So, if you are only able to stay at the top you will actually lack the right information to make the decisions at the top.” — Patric Hellermann, Practical Nerds Podcast.

Though I am certain it’s not the first time the analogy has been used, Patric Hellermann’s elevator explanation during episode 45 of Practical Nerds (about 28 minutes in), really resonated with me. Blame it on my ongoing battle with imposter syndrome or because I actively participate in reverse mentoring, but the majority of the time I am oblivious to the fact that I am at the top of the elevator. I have been so focused on consistently pushing the up arrow and hoping to get just a few floors up, that I haven’t focused on how many floors are now below me. For reference, there are approximately 39,000 people in my company and I am among the top 48 leaders. That being said, I keep my team of 36 pretty flat.

Understanding Ground Level

Over the last six months, I’ve been actively learning how to manage internal transactions within my organization. We have inter-trade between business units in various regions, and despite having a global leadership role, I realized that I had little understanding of how to set up and process these transactions. I had to direct my team to other departments to find someone who had the answers, which was not ideal or efficient. I wanted to know the process inside and out—not to micromanage, but to lead effectively.

The first time I had to process one of these $1,000 internal invoices, I made a mistake. The error ended up doubling the workload for a relatively small task, and that experience gave me an entirely new level of empathy for my team. They, too, are managing complex tasks that require precision. It made me appreciate the importance of understanding the granular aspects of operations before delegating responsibility. I’ve learned the process, and while I’m ready to hand it back to my team, I’ll revisit it periodically to stay relevant.

One of the most significant advantages of staying grounded in the operational details is the ability to detect and reduce bureaucracy. Large organizations often become bogged down by processes that, while necessary, can evolve into cumbersome systems that slow down decision-making and stifle innovation. For example, during my time managing those $1,000 invoices, I noticed several steps in the process that felt redundant or unnecessarily complex. These were steps that, had I not been involved in the process myself, might have gone unnoticed. As a result of pressing the down button, I’ve been able to streamline certain workflows and make recommendations for broader organizational changes.

Macro and Micro Management

While listening to a recent episode of The Lex Fridman Podcast, I was particularly intrigued by Elon Musk’s discussion (about 1:18 if you want to have a listen) about his involvement in detailed tasks, despite the high value of his time. As someone who manages vast enterprises like Tesla and SpaceX, Musk’s time could arguably be among the most valuable in the world. Yet, he chooses to spend it on tasks such as the optical joint work at a new AI cluster in Memphis.

For leaders at the helm of large organizations, there’s always the risk of losing touch with the daily challenges faced by employees. Over time, you might forget the nuances of what it takes to execute certain tasks. This can result in distorted decision-making because you’re relying on memories that no longer reflect the current state of operations. Decisions based on outdated experiences can easily miss the mark, leading to inefficiencies or misalignments.

Musk’s involvement in tasks like optical joint work is not about micromanaging—it’s about staying connected with the ground floor. In his conversation with Lex Fridman, Musk highlighted that understanding the smallest parts of your business can often inform better strategic decisions—in his case, decisions that could lead to gains or losses of around $1 billion.

If you’re disconnected from the core processes, how can you truly know what’s working and what isn’t? As leaders, we must strike a balance between managing macro-level responsibilities and staying connected to the micro-level details. This is not to say that executives should get bogged down in day-to-day operations—far from it. Instead, it’s about having enough of a pulse on the grassroots operations that you can identify when something isn’t working or when inefficiencies creep in.

One way to achieve this, especially when operational involvement is not realistic, is through reverse mentorship. I’ve always been a strong proponent of learning from those around me, particularly younger team members who are closer to the front lines of our business. Their perspective helps me stay connected to the ground-level challenges, even as I focus on broader strategic objectives. It’s a two-way learning street that bridges generational gaps and keeps leadership relevant.

In my own leadership structure, we manage a team of 36 people within a 39,000-person company. Keeping this team relatively flat has allowed us to maintain agility and avoid the layers of bureaucracy that often hinder larger organizations. It’s all about finding that balance—being close enough to the operations to lead effectively but distant enough to empower your team to make decisions and execute.

Empathy Through Experience

I could speak on the importance of empathy as a leader for an entire 1500+ words—and in fact I did in my article What Ted Lasso Taught Me About Leadership, so I’ll only briefly touch on it here. My experience the last six or so months working with those $1,000 invoices has been an invaluable use of my time. I dedicate hours and hours each month to developing my skills as a leader, and though that theoretical work is valuable, engaging with day-to-day operations provided me with the perspective necessary to make tangible, immediate changes to my leadership style. You know what they say about walking a mile in someone else’s shoes…

I now have a greater appreciation for the attention to detail required in seemingly small tasks like processing an invoice. I’ve also gained a newfound respect for the complexity of the systems that support our global operations. This experience has given me the insight to make more informed decisions, but also the humility to recognize when I don’t have all the answers. When you delegate tasks without understanding the effort and expertise they require, it’s easy to set unrealistic expectations. My time spent learning the invoicing process has made me more patient and mindful when assigning similar tasks to my team. It’s this type of empathy that builds trust within a team and fosters a culture of accountability.

If you’re reading this and have been in your career for some time—whether it be infrastructure or another industry—I recommend taking stock of which floor you’re on and how many flights you’ve climbed to get there. You may have forgotten what it was truly like on the ground floor or even the tenth floor. If your decision making is based on your own experience, but your experiences are 20 years old, you’re likely doing yourself and company a disservice.

All this to say, my focus has shifted from merely pushing the ‘up’ button. While I value the insights from the top floors, I equally value the perspectives gathered from the ground floor.