In this episode of The Ross Simmonds Show, Ross talks with Craig Samson, founder of Gran Sasso HR Solutions, about modern leadership, people strategy, and rebuilding organizational culture. Craig shares practical frameworks for leading with vulnerability, building high-performing teams, and evolving HR from a support function into a strategic driver of business value. He also dives into the importance of self-awareness, psychological safety, and how to lead effectively in both in-person and remote-first organizations.
Whether you're a founder hiring your first team, a new people leader, or an executive looking to scale a performance-driven culture, this episode is packed with actionable leadership wisdom.
Key Takeaways and Insights:
1. What Makes a Great Modern Leader
- Effective leaders today lead with authenticity, vulnerability, and trust.
- Leadership is no longer about knowing everything—it’s about empowering others.
- Letting go of traditional ego-driven expectations is key to being relatable.
2. Vulnerability in Leadership: Turning Weakness into Strength
- Vulnerability builds trust—it's OK (and essential) to not have all the answers.
- Invite collaboration by admitting shortcomings and asking for help.
- “The more you give it away, the more you get back.”
3. Advice for Founders Building First-Time Leadership Teams
- Founders should avoid hiring clones of themselves.
- Surround yourself with diverse thinkers—balancing fast-moving visionaries with detail-focused operators.
- Slow down to clearly communicate expectations.
4. Frameworks for Building Balanced Teams
- Understand human biases: we tend to gravitate toward those who are like us.
- Craig recommends the DiSC personality tool to build self-awareness and team compatibility.
5. Elevating HR to a Strategic Advantage
- HR must shift from policy enforcement to business partnership.
- Use data to show ROI on people investments (absenteeism, turnover, engagement).
- Craig recommends anonymous employee engagement surveys to get deeper insights.
6. Transforming Culture at Scale
- Craig shares a case study from his time overhauling HR at a billion-dollar retailer.
- Flipped the HR model by sending teams into the field to rebuild trust and partnership with operations.
- Engagement and performance increased significantly post-transformation.
7. Remote Leadership & Trust
- Manage to deliverables, not screen time.
- Over-communicate expectations and purpose.
- Use in-person time strategically to build deep connections.
Resources & Tools:
🔗 DiSC Behavioral Assessment
🔗 Gran Sasso HR
— 👋🏾 Let's stay connected —
╰ Subscribe to my channel: @RossSimmondsTV
╰ Instagram: @thecoolestcool
╰ Twitter / X: @thecoolestcool
╰ LinkedIn: linkedin.com/in/rosssimmonds
— Connect with Craig —
╰ Twitter / X: @craigsampson07
╰ LinkedIn: linkedin.com/in/craig-sampson-263b3527/
The Ross Simmonds Show