In this episode of the Second in Command Podcast, co-host Sivana Brewer sits down with Richard Scheele, CFA, CFP, Managing Partner at Next Level Planning Group and former COO Alliance member.

Richard takes us inside more than a decade of leadership evolution, from starting as an intern to stepping into the Managing Partner seat of a fast-growing financial planning firm. He shares candid stories about redefining his role, building systems around EOS, and learning to lead beyond his comfort zone. The conversation explores what happens when you outgrow your title, how teams mature into strategic thinkers, and why clarity—real clarity—changes everything.

You’ll hear how Richard and his team rebuilt their communication rhythms, created a shared playbook for decision-making, and shifted their mindset around accountability and alignment. It’s an honest, practical look at what it really takes to scale without losing culture, trust, or your own sense of direction.

Whether you’re a second in command stepping into bigger shoes or a CEO looking to strengthen your leadership infrastructure, this episode will spark ideas you can use immediately.

Timestamped Highlights

00:00 The leadership lesson Richard wishes he’d learned earlier.

02:10 Richard’s growth from intern to Managing Partner.

04:12 Why changing his title was critical for true alignment.

06:25 How EOS reshaped communication and accountability.

08:40 The value of an outside implementer for early EOS adopters.

11:03 Richard’s background in teaching economics and how it shaped his leadership style.

13:18 Creating a decision-making playbook for future clarity.

15:45 Balancing vision, strategy, and the daily operational grind.

18:20 How curiosity and vulnerability strengthen team culture.

21:03 Turning strategy into a team-driven discipline.

23:30 The evolution of Next Level Planning Group’s internal structure.

27:05 Richard’s biggest lessons from leading a rapidly growing organization.

Resources Mentioned

• Entrepreneurial Operating System (EOS)

About the Guest

Richard Scheele, CFA, CFP, is the Managing Partner at Next Level Planning Group, where he leads daily operations, strategic initiatives, and organizational coordination. Starting his career as an assistant portfolio analyst, Richard moved through roles in service, analysis, and financial planning before stepping into leadership. His background in teaching economics and his analytical approach to decision-making shape the way he develops talent, drives alignment, and supports long-term firm growth.

🔗 LinkedIn | Website

About the Co-Host

Sivana Brewer is a Fractional COO for Remote Teams and former COO at Closers.io, where she helped scale the company to multiple eight figures and built over 500+ sales teams in just 2.5 years. She specializes in leadership development, remote operations, and systems that empower teams to grow sustainably.

🔗 Connect with Sivana on LinkedIn

Important Links

• Connect with Cameron: Website | LinkedIn
• Explore the COO Alliance - The World’s Leading Community for Seconds in Command
• Get Cameron’s book: Second in Command: Unleash the Power of Your COO Book
• Take Cameron’s leadership course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)
• Chat or video call with AI Cameron via Delphi

The Second in Command Podcast is an original production hosted by Cameron Herold and co-hosted by Sivana Brewer. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.