Podcast Summary: Second in Command with Cameron Herold

Episode 531: Watters International Realty COO, Aldo Siciliano – How EOS Drives Remarkable Calm in Rapid Growth
Date: November 27, 2025
Host: Savannah Brewer (COO Alliance; guest hosting for Cameron Herold)
Guest: Aldo Siciliano, COO & President, Watters International Realty

Episode Overview

This episode explores how Watters International Realty, under the operational leadership of Aldo Siciliano, leverages the Entrepreneurial Operating System (EOS) to create stability and clarity amid rapid growth. With a deep dive into real-world execution, Aldo unpacks his approach to accountability, change management, scaling systems, hiring, and the art of balancing empathy with measurable results. The conversation provides practical insights for COOs and aspiring operational leaders looking to drive scalable success while preserving a healthy company culture.

Key Discussion Points and Insights

1. Aldo’s Career Journey & Role at Watters International Realty

• Background: Aldo began as VP of Marketing while relocating to Austin, then transitioned into the COO role as Watters implemented EOS.
  • "I started with marketing, which was a very big core function for the company. Sort of started taking on additional responsibilities as we were implementing the EOS system. And that was sort of a natural lead into taking this role." (03:38)
• Evolution to COO: The move from marketing to the COO seat required embracing general management, embedding accountability, and integrating the company’s vision and execution.

Memorable Quote:
"The ability to adapt to the CEO was probably the key factor…for the talents, skills and personalities to be complimentary and not identical." – Aldo (05:21-07:16)

2. COO/CEO (Integrator/Visionary) Dynamic

• Teamwork: Aldo described a highly collaborative process with CEO Chris—balancing Chris’s “zero to one” entrepreneurial drive with operational pragmatism and structured problem-solving.
  • "He'll come up with an idea and he'll sort of shoot it off to me...I will naturally kind of start to, in my head, break it down as to what does it feasibly look like. That’s how we kind of get on the same page." (08:33)

Timestamp: CEO/COO Dynamic Discussion [07:16 - 09:08]

3. Why EOS? Selecting and Implementing an Operating System

• Choosing EOS: Simplicity and scalability were paramount in selecting EOS over more complex systems like Scaling Up, especially given team bandwidth and business maturity.
  • "EOS is the best suited for the company that we work in simply because it's probably the simplest to operate, it doesn't have a lot of maintenance, and it's the easiest to implement across a smaller business like this one." (10:41)
• EOS Fundamentals:
  • Cadence of tracking, meetings (“Level 10s”), and problem-solving.
  • Explicit roles for “Visionary” (CEO) and “Integrator” (COO).
  • Quarterly “rocks” (major objectives) and departmental scorecards.

Quote:
"EOS creates a cadence of tracking, meeting and problem solving for the leadership team…with a big emphasis on the relationship between what's called the visionary…and the integrator." – Aldo (11:36)

Timestamp: EOS Discussion [10:33 - 13:17]

4. Incremental vs Monumental Systems Change

• Systemization & Playbooks:
  • SOPs and knowledge base are regularly updated; department leads are accountable for accuracy and relevance.
  • Small changes can have larger-than-expected ripple effects due to interdependence across teams.
  • Large changes (e.g., ATS or Salesforce rollouts) produce more resistance but are easier to document and train.
• Change Fatigue & Adoption: Resistance can be minimized by prioritizing simplicity, high ROI, and early buy-in from users.
  • "What’s really hard to ascertain before implementation is the overhead that it’s going to take in terms of time and bandwidth…It really comes down to adoption and people getting value out of it." (22:15-24:15)

Notable Segment: Change Management, Simplicity, and System Fatigue [16:17 - 27:51]
Quote:
"There is something a little perverse…because you end up actually creating more work. The software company doesn't tell you about the overhead...especially at this scale of business." – Aldo (26:19)

5. Delegation, Accountability, and Motion

• Delegation Approach:
  • Detailed briefings are standard for delegation.
  • Use of AI (ChatGPT/LLMs) speeds up document preparation.
• Project Management Tools:
  • Motion is preferred for dynamic, calendar-driven task management.
  • Previous experiences with Asana, ClickUp, and Monday.com were shaped by the company's need for simplicity and quick adoption.

Quote:
"What I like about Motion is...it will insert tasks that I have to do inside of the calendar, so it sort of fills my schedule automatically rather than me having to go and look at the list all the time." – Aldo (18:36)

Timestamp: Tools & Project Management [17:31 - 20:33]

6. Scaling Pains: Tools, Simplicity, and Teaching Teams to Think

• Shiny Object Syndrome: Both host and guest reflected on being seduced by flashy new tools, only to realize simplicity often wins and that complex platforms carry hidden costs.
• Teaching Simplicity:
  • Keeping systems simple reinforces critical thinking in teams.
  • Always clarify: What clear problem does this solve? What is the cascading effect?

Quote:
"Teach people how to think, not what to do... What is the clear problem that this is solving?" – Savannah (27:51)

Timestamp: Tools and Simplicity [24:15 - 29:14]

7. Managing Burnout, Stress, and Resistance to Change

• Burnout:
  • Leader’s role: protect team members with poor boundaries by monitoring workload and promoting prioritization.
  • Use of an “Ice Box” to capture non-urgent ideas and reduce overload.
• Attitude Management: Especially important in real estate, where sales leaders endure high emotional labor.
  • "A former boss told me, 'You’re in the attitude management business.'" (29:14)
• Stress:
  • EOS helps leaders focus on a few top priorities (“rocks”), enabling them to say no to distractions.
  • Stress often results from being in the wrong role or environment—right people, right seats matters.
• Change Management: Proper onboarding and transparent communication drive adoption and minimize resistance.

Timestamp: Burnout, Stress, Resistance [29:14 - 37:19]

8. Hiring: Emerging Versus Proven Talent

• Lessons in Hiring:
  • Early-stage companies benefit from “emerging” talent with growth potential.
  • As organizations scale, “proven” talent becomes essential for consistent outcomes and mitigating risk.
  • Missteps in big roles (especially local sales leaders) can cascade through the organization, making the right hire crucial.
  • "The thought process behind hiring has to change. The stakes become higher...and so you pay more for proven skill to reduce your risk as a business." (39:02)

Memorable Moment:
"There’s a difference between emerging talent and proven talent…that hire is very important...building it back up becomes very difficult." – Aldo (39:02)

9. Looking Ahead: Expanding with Science and Art

• Watters International Realty is testing a new expansion model, focusing on combining data-driven market selection with entrepreneurial intuition.
• "I'm really looking forward to rolling that out and seeing where the science meets the art." (42:29)

Notable Quotes & Timestamps

• On Integration:
  "The ability to adapt to the CEO was probably the key factor…" – Aldo (05:21)
• On EOS Implementation:
  "EOS creates a cadence of tracking, meeting and problem solving for the leadership team…" – Aldo (11:36)
• On Systems Adoption:
  "You end up actually creating more work...especially at this scale." – Aldo (26:19)
• On Team Development:
  "Teach people how to think, not what to do." – Savannah (27:51)
• On Burnout and Attitude Management:
  "You're in the attitude management business." – Aldo (29:14)
• On Hiring as You Scale:
  "The stakes become higher...you pay more for proven skill to reduce your risk as a business." – Aldo (39:02)
• On What’s Next:
  "I'm looking forward to where the science meets the art in terms of selecting those markets and which ones are going to pan out." – Aldo (42:29)

Key Timestamps for Important Segments

| Segment | Timestamp | |--------------------------------------------|--------------------| | COO Role & Background | 03:01 – 05:21 | | CEO/COO Dynamic | 07:16 – 09:08 | | EOS: What & Why | 10:33 – 13:17 | | Incremental vs. Monumental Change | 13:35 – 17:31 | | Project Management & Delegation | 17:31 – 20:33 | | Simplicity vs. Tool Overload | 24:15 – 29:14 | | Burnout, Stress, and Change Management | 29:14 – 37:19 | | Lessons in Hiring for Growth | 37:19 – 42:19 | | Looking Ahead: Next 6 Months | 42:19 – 42:51 |

Tone and Delivery

The conversation is candid, tactical, and warm, marked by seasoned reflections from both host and guest. Aldo’s answers are substantial but approachable; Savannah blends operational rigor with empathy and self-awareness. The tone underscores the humility and learning required to lead amid complexity and change.

Summary for Leaders

• Keep it simple: Prioritize clarity and simplicity—tools and systems should serve, not stifle, team progress.
• Prioritize hiring: Shift from nurturing “emerging talent” to seeking “proven talent” as the company scales.
• Balance empathy and accountability: Protect your team from burnout and foster a culture of open communication.
• Stay adaptable: Regularly reassess systems, roles, and tools to match evolving business needs.
• Implement with intention: Buy-in, user value, and strong communication trump feature lists in successful change management.

For more insights from top COOs, visit COOAlliance.com.