Recent articles share that 8.9 million Americans now work multiple jobs. While some pursue additional income opportunities openly, others work multiple full-time roles without disclosure, a practice known as “overemployment.”
This highlights a pattern: many executives don’t notice changes in team performance or engagement until significant issues surface.
“Whether employees are taking on side projects, pursuing passion work, or juggling multiple roles, the real question is: Why aren’t leaders noticing shifts in engagement, output, or work patterns? Usually, it’s because executives are too buried in administrative work to maintain the operational visibility that effective leadership requires,” said Fineas Tatar, productivity expert and co-founder of premium executive assistant service Viva.
According to Tatar, the ability for employees to work multiple jobs undetected, whether that’s problematic or not, reveals a broader leadership challenge: executives lack the bandwidth to truly know what’s happening with their teams.
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Tatar highlights three reasons why executives often miss important team dynamics:
1. Executives are drowning in tactical work: When leaders spend hours on calendar management, inbox triage, and scheduling coordination, they have no capacity left to analyze team output, notice engagement patterns, or identify when someone’s focus has shifted. By the time issues become obvious, opportunities for early intervention are long gone.
2. Accountability systems are reactive, not proactive: Many organizations track outcomes only when problems arise. Without consistent touchpoints, performance visibility, and regular engagement check-ins, leaders operate blind. They are unable to spot when employees are disengaged, overextended, or pursuing opportunities elsewhere.
3. Operational awareness requires bandwidth leaders don’t have: Understanding team dynamics, noticing productivity shifts, and maintaining genuine connection with direct reports requires time and mental space. When executives are overwhelmed with administrative tasks, they lose the capacity to lead effectively, regardless of their intentions.
Rather than implementing surveillance or control-based solutions, Tatar recommends executives focus on three operational shifts:
1. Reclaim strategic bandwidth: Executives need to audit where their time goes. If senior leaders are spending hours on email management, calendar coordination, or meeting prep, they lack the capacity to truly understand their teams. Delegating tactical work, whether to an executive assistant, operations lead, or trusted team member, frees leaders to focus on the human elements of management.
2. Build proactive engagement systems: Create regular structures for understanding team workload, satisfaction, and capacity. These aren’t about surveillance, they’re about genuine connection and early problem-solving. When leaders have consistent visibility into how their teams are doing, they can address issues before they escalate.
3. Create roles worthy of full attention: People seek additional income when their primary role doesn’t provide financial security or fulfillment. Executives need to ensure their teams are appropriately challenged, fairly compensated, and genuinely engaged. This requires time for career development conversations, recognition, and building the kind of culture where people want to invest their full focus.
“The conversation shouldn’t be about policing how employees spend their time. It should be about whether leaders have the operational capacity to build teams where people are engaged, fulfilled, and appropriately supported,” Tatar said. “That requires executives to work differently: focusing on leadership rather than administration.”
Photo credit: Drazen Zigic/Shutterstock
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