Behind the walls of corporate America, executive assistants [EAs] often support more than one executive. This multiple leadership model is rising as companies scale globally or restructure leadership to share accountability across business units. The model is revisited, often times, when we observe significant shifts in digital transformation. While efficient on paper, it introduces an invisible form of exhaustion, leading to cognitive overload, burnout and strategic debt.
Let’s talk about strategic debt in leadership. Strategic debt is what builds up when short-term output overrides long-term coherence. Like financial or technical debt, it builds up over time and leads to decreased morale, high turnover, missed goals, and stalled innovation if not addressed. It appears in duplicated decisions, contradictory messaging, delayed escalations, and cultural confusion.
Strategic debt is not theoretical. It shows up in day-to-day friction. You see it when projects need to be restarted because expectations were misaligned. You feel it when leaders give different instructions for the same initiative. It builds when clarity is replaced by urgency. And once embedded, it spreads.
To flag strategic debt early, here are thought-provoking questions to consider:
- Track decision reversals and alignment loops: Are initiatives constantly going back and forth for clarification or rework?
- Audit meeting outcomes: Are meetings producing actionable clarity or more questions?
- Spot unspoken workarounds: Are EAs, constantly rescheduling meetings?
- Pause pattern detection: Has the team normalized extended work hours, rapid pivots, or shifting narratives?
With these questions top of mind, conduct a situational awareness audit:
situational awareness blind spots are real
Many executives are highly focused on their deliverables, board demands, or P&L responsibilities. They often don’t recognize the cognitive load they offload because it’s not visible in a dashboard or KPI. Without structured feedback loops, their awareness is skewed.
cognitive load & “split brain”
Your brain isn’t tired because you’re not capable, it’s tired because it’s being asked to context-switch between conflicting executive needs, often in real time and across time zones. That’s a neuroscientific overload, not a personal failing.
matrix environments create a false sense of redundancy
To leaders, a multiple reporting line might seem like more “coverage.” But in reality, for the EA, it becomes an internal proxy war of prioritization, conflict resolution, and emotional labor that few leaders are trained to perceive let alone resolve.
When these signals are present, strategic debt is active. The earlier it is called out, the faster it can be corrected. Normalizing it is the bigger risk. When repeated workarounds become standard practice, strategic debt becomes the culture.
Reversing the cycle begins with insightful questions:
- What is the operating system of the leadership model? Is it intentional or inherited?
- Who owns the master narrative for strategy? Or is it fragmented?
- Which decisions are made twice due to unclear roles?
- What is the exit plan for redundancy? Or has exhaustion become normalized?
These questions will reveal whether the system has been designed for performance or is running on human overextension. And start to shift the narrative from vulnerability to structural insight. Here’s areas to consider in rewriting the code to strategic alignment:
- book alignment sessions the first Monday of each month for leaders to commit to agenda and executive outcomes
- capture areas where there was friction or bottlenecks
- block ‘headspace’ in calendars to have time for deep think and work
Organizations that aim to build resilient executive operations and efficiency should position the EA function as a strategic integrator in the approach. This may include:
- defining shared priorities and decision rights
- establishing operational balance between leaders
- building recovery cycles for roles with high cognitive demand
- recognizing when strategic debt is being offloaded onto the workforce
The best leaders and companies are ambidextrous: prudent about managing the downside while aggressively pursuing the upside.
Source: Organizational Ambidexterity in the Age of Volatility by McKinsey
Pushing through is not the same as leading well. Sustainable performance requires structural alignment, not constant endurance. When one brain carries the load of two or more, it is not a competitive advantage. It is the beginning of system failure. That failure does not start with a missed meeting. It starts the moment the leader’s inability to align strategically and the structure reveals it is now taxing on the people and long-term impact on organizational health. The workforce performs diligently to maintain alignment across strategy, personalities, time zones, and power dynamics often without recognition for the effort it requires.
While EAs do not have the formal authority to denounce strategic leadership debt unilaterally, their proximity to executives and influence over information flow makes them critical in early identification and mitigation. Get in front of it by asking questions no one else is thinking of.
To scale in the AI era, the mindset needs to shift. Build to empower people. Replace survival with strategy. And ultimately lead with intention.
