Interview Highlights

Becoming a Great Boss Starts with the Right Foundation

Entering management is exciting—but also intimidating. According to Forbes, 60% of new managers fail within their first 24 months. But with the right support, mindset, and leadership qualities, those odds can shift.

In this episode, we follow the journey of Alessandro Patruno, Head of Business Intelligence and Planning Transformation Initiatives at Valentino, who transitioned from an individual contributor to a confident and effective leader.

From Contributor to Leader at Valentino

Valentino, a global luxury fashion house with over 4,000 employees, entrusted Alessandro with leading its BI office and overseeing transformation initiatives. His transition wasn’t easy—but it reveals exactly what it takes to become a great boss.

The Real Challenges of Becoming a Manager

Alessandro shares how difficult it was to go from managing only his own work to being accountable for others. He struggled with:

  • Resisting the urge to micromanage
  • Learning to lead diverse teams with different perspectives
  • Balancing performance with empathy

These are common pain points for first-time managers—and ones he overcame with intention.

Building Trust and Team Cohesion

What made Alessandro a great boss wasn’t technical knowledge—it was trust. He focused on:

  • Understanding team members’ strengths and weaknesses
  • Offering tailored support
  • Celebrating collective wins rather than spotlighting individuals

Trust became his foundation for strong team culture.

Why Soft Skills in Becoming a Great Boss Matter More Than You Think

Learning communication, empathy, and collaboration aren’t soft—they’re core. Alessandro emphasizes the role of soft skills in:

  • Creating psychologically safe environments
  • Helping team members feel valued
  • Encouraging honest feedback and performance

How He Supports Other New Managers

Now leading other managers, Alessandro acts as a mentor. He offers:

  • Regular feedback
  • Peer coaching
  • Guidance on handling difficult conversations
  • He shows how great bosses multiply leadership by uplifting others.

So, how do you become a great boss?

According to Alessandro:

  • Prioritize authenticity over perfection
  • Build trust before demanding results
  • Stay humble and curious—especially during team friction or failure

Conclusion: Lead with Purpose, Not Just Authority

Moving into management is a milestone that demands more than technical ability. As Alessandro’s story shows, becoming a great boss means embracing trust, vulnerability, and people-first leadership. When new leaders lead with emotional intelligence, they don’t just manage—they transform teams.

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Confident male executive standing against a red wall, representing leadership presence and how to be a great boss through composure and style.
Official Transcript

“60% of new managers fail within the first 24 months in their new role, according to research from CEB Global” (Forbes).

The phenomenon of high failure rates among new managers is particularly pronounced in individuals from technical backgrounds such as scientists, engineers, or business intelligence analysts, who may have less experience with soft skills. Adequate preparation for these transitions can mitigate these challenges, saving organizations time and facilitating quicker trust-building between new managers and their teams. This ultimately leads to enhanced productivity as teams sync up faster.

Our guest today will share his incredible journey from individual contributor to manager, to now the Head of Business Intelligence and Planning Transformation Initiatives at the Italian luxury fashion house Valentino, please welcome Alessandro Patruno.

Alessandro, thank you so much for being with me today.

Alessandro Patruno: Hi, Felicia, thank you so much to you. It's a really pleasure to be with you today. Let me also wish happy St. Valentine's Day to all lovers and happy birthday to my mother whose birthday is today. Buon compleanno mama!

Felicia Shakiba: And Happy Valentine's Day to you as well. And it's so nice to have you here on this special day.

And so Alessandro, my first question I'd love to ask you is if you could provide some background on the Valentino organization and your role.

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