Originally published December 30, 2024 · Edited February 23, 2026 · About our editorial process
City managers and county administrators often work under immense pressure. Taking time away can feel impossible, even during quieter seasons. But the difficulty of stepping away often reveals something more interesting than workload. It reveals what the leader actually protects.
A Think Tank session posed a direct question: What are your biggest fears about being away for an extended period of time? The discussion that followed moved quickly past logistics and into territory that surprised the room. The fears weren’t really about missed deadlines or unresolved issues. They were about identity, control, and what it means to lead an organization that can function without you.
What the Fear Actually Reveals
Leaders who hesitate to disconnect often describe their concern in operational terms: the project that needs oversight, the council member who might call, the decision that can’t wait. These concerns are real. But underneath them sits a harder question: what does it mean about my leadership if the organization runs fine without me?
That question is uncomfortable because the answer cuts both ways. A team that falls apart in a leader’s absence signals a system built around a single point of failure. But a team that operates seamlessly can feel threatening to a leader whose identity is tied to being essential.
The Think Tank practitioners who discussed this noticed a pattern in themselves. The leaders who struggled most with stepping away were often the ones who had built the tightest circles of control. Not because they didn’t trust their teams, but because the systems they’d created rewarded their presence and penalized their absence. The environment, not the individual, made disconnecting feel risky.
Simon Sinek describes this as the Circle of Safety: the boundary within which people can focus on the work rather than protecting themselves from internal threats. When a leader’s absence creates anxiety across the team, it signals that the Circle of Safety depends on one person’s presence rather than on the systems and trust the organization has built. That’s a structural vulnerability, not a staffing plan.
What Delegation Actually Tests
The standard advice about preparing for absence focuses on mechanics: assign clear roles, provide resources, communicate the chain of command. That advice isn’t wrong. But it skips the question that makes delegation hard in the first place.
Delegation isn’t really about task assignment. It’s about what a leader is willing to release. Leaders who delegate effectively tend to have already answered a prior question: do I believe my team can make good decisions without me, and am I willing to live with decisions I wouldn’t have made?
The Think Tank discussion surfaced a revealing tension. Several leaders described wanting to delegate more, then finding themselves checking in anyway, reviewing decisions after the fact, or creating approval requirements that nominally empowered the team while preserving the leader’s veto. The stated value was trust. The demonstrated behavior was control.
That gap between stated and demonstrated values is exactly what Define What Matters pressure-tests. Not “do you believe in delegation?” but “what do you actually do when someone makes a decision you disagree with while you’re away?”
The Organizations Where Absence Works
Leaders in the Think Tank who described successful extended absences shared a common pattern. The preparation wasn’t a pre-vacation checklist. It was a culture that had been built over months or years, one where team members already made decisions, already owned outcomes, and already had the psychological safety to act without checking upward first.
In those organizations, the leader’s absence didn’t create a gap. It confirmed what was already true: the systems held because they were designed to hold, not because someone was watching.
These leaders described several conditions that made this possible. Team members had practiced making decisions at increasing levels of authority, with the leader available but not directing. Mistakes were treated as learning data rather than evidence of failure. And the leader had done their own work of separating their identity from their indispensability.
One practitioner described a deliberate practice: turning off the phone completely during time away and telling the team explicitly not to contact them. The message wasn’t “I don’t care.” The message was “I trust you, and I’m proving it.” Upon returning, the leader found not just continuity but growth. Problems had been solved in ways the leader wouldn’t have chosen, and some of those solutions were better.
What Absence Teaches the Leader
The Think Tank conversation kept returning to an insight that no one had expected going in. Stepping away doesn’t just test the team. It tests the leader’s relationship with their own value.
Leaders who built their careers on being the person with the answers, the person in the room, the person who holds it together, face a genuine identity challenge when they discover the organization can thrive without them. That discovery is a Face the Truth moment. The gap between “I’m essential” and “the team is capable” isn’t a failure of leadership. It’s evidence that the leader built something that works.
The practitioners who described being most at peace with absence were the ones who had reframed what leadership success actually means. Not “they need me” but “they’re ready.” Not control, but capacity.
The Question Underneath
The ability to lead while absent isn’t really a skill. It’s a values question that surfaces slowly, through the accumulated choices about what a leader builds, what they release, and what they protect.
In The Shift That Sticks methodology, this sits squarely in Define What Matters. The practice asks leaders to examine what they actually protect under pressure, not what they claim to value. For many leaders, the pressure of stepping away reveals the answer more clearly than any diagnostic.
Face the Truth creates the conditions for honest self-assessment about the gap between stated trust and demonstrated control. Make It Real turns that awareness into systems: decision-making authority distributed before it’s needed, not assigned in a rush before a vacation. And Reinforce the Change builds the rhythms that sustain team autonomy, so that a leader’s absence becomes unremarkable rather than heroic.
Related Reading
Research Foundation:
- The Expectation Gap: What drives engagement when leaders empower their teams
- Political Dynamics: How governance pressures shape the environment leaders navigate
Related Articles:
About Rob Duncan
Rob Duncan spent two decades watching what happens when leaders say one thing and protect another. As founder of Imagine That Performance, he works with city managers, county administrators, and government leaders through Think Tanks, workshops, and executive coaching to close the gap between intention and experience.
The Question Worth Asking
If you stepped away for two weeks with your phone off, what would you be most afraid of? The answer probably isn’t about operations. In the Think Tank, leaders examine what that fear actually protects, with peers who’ve faced the same question honestly.
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