Podcast Summary: The Shocking Mistakes COOs Make (and How to Avoid Them)

Podcast: Second in Command: The Chief Behind the Chief with Cameron Herold
Episode: 516 – Imad Jbara
Recorded: October 7, 2025

Episode Overview

In this insightful episode, Cameron Herold sits down with Imad Jbara, COO for L2, Infinite Insurance and former COO at Wojo Media, to discuss the often-overlooked yet critical mistakes COOs make—and how to avoid them. The conversation explores practical leadership strategies, building high-performing teams, orchestrating culture change, navigating rapid growth, and the personal evolution required to succeed as a "Chief Behind the Chief." Imad draws from his extensive experience scaling companies alongside household names like Tony Robbins, Grant Cardone, and Alex Hormozi, aiming to share actionable wisdom for fellow COOs and operational leaders.

Key Discussion Points & Insights

1. The Challenges of Culture Shift and Setting Standards

• Initial Hurdles: Imad describes his first major lesson: transitioning into new roles and earning respect, struggling between being "too aggressive or too kind."
  Quote [00:00]:

  “I came in and I was kind of tired of the shit and I was aggressive and it bit me in the ass because the culture then shifted. Great, because now we were defined as [a] standard. But it kind of took a little bit longer for me to build everybody up...” — Imad

• Redefining Expectations: He emphasizes the importance of clearly establishing high standards and not tolerating mediocrity.

2. Diagnosing and Fixing Structural Issues

• On joining Wojo Media, Imad faced a client retention crisis (20%) and chaotic, "pod-like" organizational silos.

• Strategic Steps:

  • Broke down the org chart into distinct departments (copywriting, graphics, media buying).
  • Promoted informal leaders to managers and implemented daily 15-minute huddles.

• Communication Cadence:
  Quote [06:23]:

  “...the agenda for [the huddle] was, ‘What are the problems today? What happened yesterday that was a major issue? What can we do today to make it better? What's the goal for the week?’ ...Let’s focus on the present, brick by brick.”

• Immediate Impact: Client retention jumped from 20% to 80% within six months, tripling revenue.

3. Managing and Removing Toxic Employees

• Imad discusses his approach to handling "cultural cancers."

• Lesson Learned:
  An abrupt, aggressive firing strategy backfired—creating anxiety and a sense of expendability among remaining team members. Quote [11:19]:

  “I came in and I was kind of tired of the shit, and I was aggressive and it bit me in the ass... not everybody was afraid because they felt expendable...the most important currency in a company is safety and security. If your employees feel safe and secure, they will give you the roles.”

• Best Practice: Balance high standards with genuine care and create an environment where employees feel secure.

4. Growing and Empowering Managers & Building SOPs

• Leadership Pipeline:

  • Encouraged managers to create their own SOPs for all aspects of their roles, ensuring the organization wasn’t dependent on any single "irreplaceable" employee.
  • Required managers to present problems with three solutions. Quote [09:18]:

  “A manager tells people what to do. A leader creates individuals that can think for themselves and... move the company forward without them.” — Imad

• Practical Systems: Utilized templates and checklists; lag in KPIs or repeated questions signaled SOP non-compliance.

5. Reflections on Personal Growth and Leadership Style

• Wisdom Over Time: Imad admits that earlier in his career he let ego and impatience dictate his approach, only learning patience, humility, and the importance of teamwork through failure and “pain.”
• Delegating the Ego: Key advice from a mentor—don’t make yourself a single point of failure.
  Quote [15:10]:

  “You just built a liability and you’re bragging about building a liability...it showed me something where I was still the bottleneck.”

6. Feedback, Praise, and Constructive Criticism

• Praise vs. Criticism: Cameron advocates the "positive sandwich" (praise, criticism, praise) to grow confidence and skills, rather than tearing performers down. Quote [17:17]:

  “You have to praise people twice as often as you actually give them criticism...Our job is to grow their confidence, their skills, their confidence, their skills.”

7. Onboarding and Training for Success

• Comprehensive Onboarding:
  • Imad recommends as much time onboarding as spent recruiting, with daily checklists and gradual trust-building.
  • First three months should involve micromanagement to establish standards.
  • Full transparency with new hires—explain micromanagement is for their benefit and trust-building.
• Role Modeling: Leaders should do the job first, document the process, then delegate. Never abdicate training to untrained staff.

8. Coping with Leadership Stress & Mentorship

• Support Systems:
  • Imad emphasizes having a circle of high-level, heart-driven mentors as a “safe space” for voicing doubts and seeking advice.
  • Cites mastering delegation and transparent communication as a constant skill focus.

9. COOs Need Sales Skills

• “You’re literally selling ideas every single day ... If people come in there and they're afraid to sell, this is not the position for you. You can't be a leader.” — Imad [27:02]

10. Navigating AI & Rapid Change

• Facing Employee Fears: Imad addressed AI job-security anxieties by encouraging staff to master AI and expand their capabilities, not hide from the change.
• Transparency: Always communicate looming changes early and honestly, so employees can adapt proactively.

11. Advice to His Younger Self

• Be patient. Growth, trust, and skills only come through enduring the “pain” of failure.
• “If someone gives you advice, just shut up and listen. Especially if there's somebody that you want to switch positions with, please, for the love of God, just shut up and listen.” — Imad [30:34]

12. What’s Next for L2 Infinite Insurance

• Recently secured capital funding (now valued at $18M), Imad is navigating the learning curve of VC-backed growth vs. bootstrapping. He's focused on leveraging mentorship and avoiding common new-COO pitfalls.

Memorable Moments & Notable Quotes

• “A manager tells people what to do. A leader creates individuals that can think for themselves.” — Imad [09:18]
• “The most important currency in a company is safety and security. If your employees feel safe and secure, they will give you the roles.” — Imad [12:15]
• “You are not going to get replaced by AI—you'll get replaced by an employee who’s using AI.” — Cameron [29:11]
• “If you got hit by a bus tomorrow, what happens to the department? ... You just built a liability.” — Imad [15:10]
• “No shot. I don't believe that at all. Because you're literally selling ideas every single day... You can't be a leader if you can't sell.” — Imad [27:02]
• “Be patient. You don't know it all... The only way I learned those skills was through pain, through failure, through losing the opportunities I thought would change my life.” — Imad [29:37]

Timestamps for Key Segments

| Segment | Timestamp | | --------------------------------------------- | ---------- | | Initial lessons in cultural shifts | 00:00–02:30| | Diagnosing and repairing structural issues | 02:30–04:30| | Daily huddles and communication routines | 06:00–07:30| | Growing/empowering managers, SOPs | 07:30–10:00| | Removing toxic employees | 10:50–12:30| | Building safety & security in culture | 12:15–13:30| | Feedback, praise, and the “positive sandwich” | 17:17–18:30| | Onboarding & team integration | 21:53–23:30| | Coping with leadership and stress | 24:21–25:30| | Selling as a COO core skill | 27:02–27:25| | Approaching AI and change management | 28:10–29:37| | Advice to younger self, wrapping up | 29:37–31:16|

Tone & Language

The exchange is energetic, candid, and filled with practical (sometimes blunt) wisdom. Imad is self-deprecating and direct, often using humor and real-life examples. Cameron offers complementing insights with a mentor's voice, balancing praise with reflection.

Takeaways for COOs & Leaders

• Set clear standards, but anchor them in care.
• Early communication rhythm (daily huddles) is vital for rebuilding structure.
• Accelerate leadership development by making managers think and own their roles.
• Don’t let ego make you a single point of failure—document, systematize, and delegate.
• Nurture your personal growth by seeking mentorship, honest feedback, and continuous learning—especially around sales and change management.
• Face technology shifts (like AI) head on, and guide your team to adapt rather than resist.
• Patience and humility are earned through experience—don’t rush the process.

For more COO best practices, visit cooalliance.com