I recently participated in the “uppers, middles, and lowers” exercise, a powerful simulation that compresses organisational dynamics into a short timeframe, making patterns visible that usually unfold more gradually. I was randomly chosen to take the role of CEO of “CatsRUs,” a temporary virtual organisation with three managers and eight workers. Our task: draw as many acceptable, high-quality cat stick figures as possible in 40 minutes.
As CEO of this small organisation, I wanted to establish a flat hierarchy and avoid a commanding approach, seeking input from the wider team on how we wanted to work together. However, a dynamic of authority and hierarchy developed very quickly, and time constraints forced me to make quick decisions without full consultation.
Falling prey to “following orders”
The exercise defined some rules of engagement. When I shared these with the team, the requirements were accepted without challenge to authority. As CEO, I was able to change the rules, but I didn’t; even I fell prey to the “following orders” dynamic.
This aspect is often overlooked: leaders can be just as susceptible to deferring to “the rules” as anyone else, perhaps even more so when we feel the weight of responsibility. What held me back? I believe it was a combination of the legitimacy the exercise structure provided and that, in the rush, it simply didn’t occur to me as an option.
I received questions from the team, but no one really challenged me or my answers, possibly because most knew me personally and trust was already established, or because my explanations seemed rational enough. When asked about delivery targets, I used these as opportunities to reaffirm the culture I wanted to see: people over delivery, which felt even more feasible in an experimental environment.
The paradox of participative leadership under time pressure
My intent was flat hierarchy and consultation, but reality demanded rapid decision-making. This tension is real and persistent in leadership. I landed on a hybrid: making decisions quickly while explicitly framing the culture as “people over delivery.” That’s not failure to be participative; it’s adaptive leadership.
The question becomes: did my team experience my quick decisions as autocratic, or did my explicit cultural messaging give them enough psychological safety that the speed felt acceptable? What we found was that ambiguity around targets created both frustration and creative freedom. And workers valued task enjoyment over organisational goals.
Neglecting middle management
I focused on a flatter hierarchy and involving everyone. But in the process, I felt like I neglected middle management. Each manager chose a different approach to managing their teams, which was interesting to observe.
This is perhaps the most common blind spot in flat-hierarchy approaches. I tried to connect directly with everyone, which can inadvertently disempower or confuse middle managers about their role. The fact that each manager chose a different approach suggests they were navigating ambiguity about their mandate. They interpreted my flat approach as permission to be highly autonomous, but it would have been good to explicitly define what I wanted from them.
Managers also spoke for their teams instead of individual team members, a pattern that emerged quickly, and I will continue to reflect on.
Carrying emotional load while leading in the grey
As a leader, I carried the emotional load of the team, perhaps even more so because I wasn’t pushing a command-and-control approach. The team needed to be okay working in the grey, and I needed to be reassuring whilst not providing definite answers, holding space for the group to find its own way.
There is a tension in the paradox between uncertainty and autonomy that deserves more discussion. Autonomy without structure or direction can feel like abandonment. Certainty without autonomy feels controlling. The leader’s work is to provide enough container—reassurance, boundaries, purpose—while leaving enough space for agency. It’s exhausting because one cannot optimise for both simultaneously; you must constantly read the room and adjust.
Isolation and disconnection
Certain themes of isolation and disconnection emerged across all roles. As CEO, I felt isolated in my leadership office and preferred visiting teams. Silos also formed quickly between the separate work teams. Loneliness in remote work environments is rife generally, and I felt it even more acutely in a leadership position.
Physical and emotional responses to power differentials emerged rapidly, even in this brief exercise.
The amplified impact of leadership
Being in a higher leadership position means having a wider impact on organisational culture, something I felt acutely even in this 40-minute exercise. Every decision I made, every question I answered (or didn’t answer), every visit to a team workspace sent signals about what mattered and how we should work together. My choice to prioritise “people over delivery” rippled through the organisation in ways that individual contributors’ choices could not. This amplification effect is both the opportunity and the burden of leadership: you shape culture not just through explicit policies, but through the accumulation of small moments and micro-decisions that others observe and interpret.
This exercise was rich and thought-provoking precisely because it made visible the complex dynamics that shape how we work together in a very short time.