Ten common questions about COOs answered by Cameron Herold

Executive overview

New COOs rush to install systems before earning trust, and experienced ones make rookie hiring, firing, and project decisions too fast. The COO role demands a shifting skill set — from relationship-building early on, to situational leadership, to knowing when to be vulnerable and when to project confidence.

Cameron Herold draws on his experience at 1-800-GOT-JUNK and two decades coaching second-in-commands to address the ten questions he gets asked most.

The fastest way to fail as a COO is to execute before you connect.

The new COO's relationship trap

• Push systems before building trust and direct reports back-channel, argue, and disengage.
• At 1-800-GOT-JUNK, the CEO had to bring in a marriage counselor after Herold alienated the team within weeks.
• Fix: spend the first weeks getting to know people, honoring prior work, and earning relational capital.
• People execute on your plans once they feel connected to you — not the other way around.

Changing industries as a COO

• Fear of switching industries comes from misidentifying your strengths as industry-specific.
• A mastermind-style review with trusted peers surfaces transferable strengths you've dismissed.
• Core COO skills — operations, people, recruiting, leadership — move across any sector.
• You can't see your own situation as clearly as those around you; put yourself in the right rooms.

Moving from COO to CEO

• Imposter syndrome stops most COOs from attempting the jump.
• Surround yourself with peers who have made it; seeing it done removes the mental ceiling.
• The transition isn't just adding CEO responsibilities — it's delegating COO responsibilities.
• Work with a coach to shift from execution mindset to 30,000-foot strategic thinking.

Situational leadership

• Most leaders frustrate teams by applying the same style to every person and every project.
• Situational leadership matches your coaching style to the skill level and confidence of the individual on a specific task.
• An employee who complained about micromanagement later asked to be micromanaged on a different project — that contrast is the core insight.
• Adjust style per person, per project; results improve for everyone.

Peacetime vs wartime leadership

• Some moments require a full pivot from collaborative to decisive, directive leadership.
• During COVID, Herold had to rebuild the COO Alliance's entire model (five in-person events) in roughly one week.
• When followers are looking to follow, leaders must lead — hesitation compounds the crisis.

Calendar chunking for COOs

• COOs are pulled in many directions and rarely batch similar work together.
• Switching between unrelated cognitive modes (video production → accounting → coaching) kills flow.
• Block your calendar so the same kinds of tasks sit in the same time slots.

Senior leaders still need coaches

• Deep domain expertise doesn't exempt you from needing external perspective.
• As a student in Dan Martel's coaching program, Herold gained both content and observational insight into coaching craft.
• Every elite athlete still has a coach; the same principle applies to executives.

How much vulnerability is too much

• Showing weakness to your team creates psychological safety — until it undermines belief in leadership.
• Sharing genuine fears about profitability or business model viability can freeze a team that still needs to trust in direction.
• Keep existential uncertainty with peers, coaches, or board — not direct reports.
• Balance: be vulnerable, but preserve the team's confidence that someone has the wheel.

When a CEO needs a COO

• Clear signals: can't take five or more weeks of disconnected vacation; overwhelmed across all business areas; no time to develop direct reports.
• The COO's job is to free the CEO to operate in their unique ability.
• Tenuity grew from 40 to ~1,400 employees after the CEO delegated day-to-day to a COO and elevated to strategic work.

The number one rookie COO mistake

• New COOs fire people, hire people, and launch complex projects too fast.
• The first 90 days should be observation — attend meetings, learn culture and history, build relationships.
• Slow down all critical decisions for at least 90 days; speed up only after you understand the organization.

How to land your first COO role

• Focus on three things: skills, confidence, and connections.
• Consume targeted content (courses, books like The One Minute Manager) to close skill gaps.
• Join communities like the COO Alliance to shed imposter syndrome through peer accountability.
• Confidence compounds once you see hundreds of peers navigating the same challenges.