Second in Command with Cameron Herold

Ep. 508: Sarah Harris – Uncovering the Secrets of Successful COOs: Empathy, Autonomy, and Impact
Date: September 9, 2025
Host: Savannah Brewer (Co-host, standing in for Cameron Herold)
Guest: Sarah Harris (Fractional COO, OM agency; Leadership coach; Certified counselor)

Episode Overview

The episode dives into the essence of modern operational leadership with Sarah Harris, a fractional COO, leadership coach, and qualified therapist. The conversation unpacks Sarah's unique blend of operational expertise and psychology to reveal transformative strategies for creating thriving, accountable, and psychologically safe teams. Key themes include:

• The distinctive challenges of founder-led businesses
• Building feedback-rich and autonomous cultures
• Leveraging empathy and curiosity to drive deep, sustainable change
• Harnessing quiet observation as a diagnostic tool for operational health
• Practical leadership tactics for fractional and full-time COOs

Key Discussion Points & Insights

1. The Unconventional COO Journey (05:46–08:06)

• Sarah’s path: From commercial roles in professional services to MD, taking operational leadership but backed by counseling and coaching qualifications.
• Unique background: Counseling provides depth and empathy; coaching builds resilience and high performance.
• Quote (Sarah Harris, 05:46):

  "I became the person who could solve sort of deeper business problems...that instinct led me into my first managing director role. At that point, I was already a qualified therapist. Coaching gave me the tools to build resilient, healthy, high-performing teams."

2. Working with Founder-Led Businesses (08:06–10:00)

• Founder involvement: Offers passion and emotional investment, but can create bottlenecks or decision-making blockages.
• Pattern recognition: Founders embed their own dreams, insecurities, and family patterns into the company DNA, often unconsciously.
• Quote (Sarah Harris, 08:59):

  "Founders build themselves into their businesses. Some of what they build is beautiful, and some of it can create blockers...quite often even a decade on."

3. Identifying and Shifting Bottlenecks (11:16–13:15)

• Hands-on founders: Over-involvement can disempower teams and create cultures lacking accountability.
• Bottleneck example: CEO entrenched in too many decisions slows down and demotivates teams.
• Empowering teams: Systematizing decision-making clarifies ownership, reduces paralysis, and distributes accountability.

4. Observation and Quiet Diagnosis (14:14–15:50)

• Avoid immediate problem-solving: Initial period should emphasize observation, curiosity, and listening before taking action.
• Look for patterns: Recurrent operational issues often stem from emotional, not procedural, causes.
• Data-driven alignment: Use retrospectives and feedback to gather insights and present leadership with observed root causes.

5. Delegation, Focus, and Time Management (18:12–20:40)

• Fractional COO challenges: Living in dual timelines—strategy and fixing real-time fires.
• Leadership development: Develop managers to cascade leadership, resist the urge to solve all tactical problems yourself.
• Boundaries as essential: Time management and the courage to delegate are necessary skills for any second-in-command.

6. Building Feedback-Rich Cultures (22:31–24:50)

• Feedback foundation: Most operational issues are disguised communication failures.
• Modeling feedback: Leaders must model and invite feedback in every direction.
• Institutionalizing feedback: Bake feedback mechanisms into rituals (retros, 1:1s, performance reviews).
• Quote (Sarah Harris, 22:31):

  "If you don’t build a culture of feedback early on...you just end up papering over problems. Feedback isn’t conflict, it’s clarity."

7. Psychological Safety and Team Feedback (25:09–26:56)

• Employees need safety to share: If voices are silenced, innovation and engagement suffer.
• Surveys and observation: Regular employee surveys and acute meeting observation flag when teams are shrinking away or disengaged.
• Invitation matters: Always ask team members for feedback; demonstrate that it’s heard and valued.

8. Handling Feedback You Disagree With (27:38–28:52 & 30:14–30:49)

• Pause before reacting: Acknowledge without owning if feedback doesn’t align, reflect, and follow up thoughtfully.
• Neuroscience tip: The threat-detection part of your brain responds before the decision-making part—always pause.
• Quote (Sarah Harris, 27:38):

  "You don’t have to own it, but you can acknowledge someone else’s experience...Take it away. You don’t have to respond in the moment."

9. Bringing Therapy & Coaching Into Operations (31:42–34:10)

• Empathy as a toolkit: Understanding people helps tackle the real obstacles underlying process problems.
• Curiosity and respect: Ask open questions, seek out emotional drivers, and use these as leverage for sustainable solutions.
• Quote (Sarah Harris, 31:42):

  "Businesses are people...If you understand emotions and what drives people, it makes it much easier to solve those problems."

10. Enabling Autonomy and Ownership (34:55–37:26)

• Facilitate, don’t solve: Empower teams to problem-solve, offer accountability for risk, and encourage iterative experimentation.
• Coaching up the ladder: Require clear problem-definition and business case thinking; always ask, “What problem are you trying to solve?”
• Quote (Sarah Harris, 34:55):

  "I’ll help facilitate the conversation...but I try not to take the decision for them. But that safety...I will always offer my accountability. Go for it—it's on me if it doesn't work."

11. Diagnosing Emotional Health of a Business (44:32–46:28)

• Signals of health/unhealth:
  • Lack of engagement (flat energy in meetings, low Slack participation)
  • Declining client satisfaction or higher churn
  • Reduced ownership or accountability
  • Rising CEO frustration from carrying team energy
• COO as temperature gauge: Straddles aspiration with operational reality, balancing needs of leadership and team.

12. Leadership Tools & Tactics (46:28–48:41)

• Listen for what’s unsaid: Non-verbal cues, meeting dynamics, Slack engagement—lots is communicated between the lines.
• Plan for the unfinishable: To-do lists never end—reprioritize daily, focus on the top goals, and let lesser tasks fall away.
• Quote (Sarah Harris, 47:06):

  "Get curious about what’s not being said...Really listen out for those non-verbal cues. Trust your instinct and lean into those."

Notable Quotes & Moments

• On Founder Bottlenecks
  "The business has been born from them...founders build themselves into their businesses. Quite often even a decade on, you see bottlenecks intrinsically connected to the founder." – Sarah Harris (08:59)

• On Observational Leadership
  "If the same operational issues keep coming up, I would say it’s probably emotional and not procedural." – Sarah Harris (14:14)

• On Feedback Culture
  "Feedback isn’t conflict, it’s clarity. Bake feedback into the system, not just the culture." – Sarah Harris (22:31)

• On Safe, Reflective Feedback
  "Take it away. You don’t have to respond in the moment. Thank you. Let me think on that and I’ll come back." – Sarah Harris (27:38)

• On Not Having All the Answers
  "You don’t need to come in with all the answers...the real value is creating the conditions for other people to emerge with answers to their own questions." – Sarah Harris (41:17)

• On To-Do Lists and Priorities
  "I had an epiphany...that I was never going to get to the end of my to do list. You just need to hit the top two things on it every day." – Sarah Harris (47:06)

Timestamps of Key Segments

• 04:09: Sarah’s background introduction
• 08:20: Defining founder-led companies
• 11:16: Case study: Bottlenecks caused by founder involvement
• 14:14: Initial strategy: Observation in a new COO role
• 18:12: Delegation and leadership development as a fractional COO
• 22:31: How Sarah builds feedback cultures
• 25:09: Detecting feedback and safety issues
• 27:38: Handling feedback you don't agree with
• 31:42: Therapy & coaching skills in operational leadership
• 34:55: Fostering team autonomy and experimentation
• 44:32: Emotional health indicators in a business
• 46:28: Must-have practices for healthy culture
• 49:44: What Sarah is excited about next

Episode Takeaways

• For COOs and operational leaders:

  • Ask powerful questions, not just fix symptoms.
  • Feedback is foundational—model it and institutionalize it.
  • Psychological safety unlocks creativity, accountability, and innovation.
  • Successful leaders facilitate and coach rather than monopolize problem-solving.
  • Observation and curiosity reveal the real levers for change.

• Practical tools:

  • Quarterly employee surveys, retrospectives, feedback rituals
  • Daily reprioritization aligned to impact/consequence, not just urgency
  • Simple business case approach for team experiments and problem-solving

Where to Connect

Sarah Harris:

“Come and find me on LinkedIn.” (52:12)

This episode is a real masterclass for COOs striving for impactful, sustainable leadership, blending structure, heart, and the courage to pause and observe before acting.