Ask Me Anything - 90 Minute Session

“I engaged with Alessandro as I was transitioning into a Head of Engineering role for the first time - a period with no shortage of uncertainty and pressure. What stood out immediately was his wisdom. Alessandro seemingl…” “I engaged with Alessandro as I was transitioning into a Head of Engineering role for the first time - a period with no shortage of uncertainty and pressure. What stood out immediately was his wisdom. Alessandro seemingly had a pithy anecdote or framework for every situation, and his depth and range of experience came through clearly in that respect. Alessandro’s approach as a mentor is inquisitive and thoughtful. He never jumped to conclusions; he took the time to understand the nuances of my situation before offering perspective, whilst also sharing freely from his own experiences. That combination made his guidance specific and actionably, and helped me clarify my own thinking and consequently make better decisions. I also appreciated that our sessions didn’t feel transactional. There was a warmth and curiosity on his side that made the whole experience feel grounded and genuine. If you’re stepping into a leadership role for the first time or navigating a difficult transition, I’d warmly recommend working with Alessandro. I’d welcome the opportunity to do so again myself.” Read more Show less

Simon

Standard Plan · 7 months

“Alessandro was a great mentor who helped me to get me into the shape I needed to be to score my new job. He gave me the tools and framework I needed to better approach new challenges and helped me to take advantage of m…” “Alessandro was a great mentor who helped me to get me into the shape I needed to be to score my new job. He gave me the tools and framework I needed to better approach new challenges and helped me to take advantage of my past experiences to become a better PM and Manager. Thank you again Alessandro!” Read more Show less

Matteo

Standard Plan · 2 months

“I've had the privilege of working with Alessandro as my leadership mentor, and the impact on my growth as an Engineering Manager has been remarkable. **What makes Alessandro exceptional:** Alessandro combines deep…” “I've had the privilege of working with Alessandro as my leadership mentor, and the impact on my growth as an Engineering Manager has been remarkable. **What makes Alessandro exceptional:** Alessandro combines deep analytical and strategic thinking with genuine empathy. He doesn't give surface-level advice – he asks probing questions to understand root causes, then provides concrete, actionable strategies. When I struggled with hiring, he walked me through the entire framework: understanding value vs. cost, building decision matrices, and calibrating expectations against real-world standards from Google and Silicon Valley. His expertise helps me see patterns I would miss on my own and position challenges in a broader strategic context. **What I learned:** Alessandro pushes me to think like a Director, not just an EM. He taught me to use competency matrices as objective decision-making tools, challenge assumptions from my own teams, and translate technical language into management language for executive conversations. Most importantly, he creates a safe space for growth. When I made mistakes – like speaking too candidly about performance issues to our CTO or giving answers I wasn't certain about – his question wasn't "Why did you fail?" but "What did you learn, and how will you approach it next time?" This approach equipped me with tools to handle similar high-stakes situations better. Since working with Alessandro, I've made significant progress overcoming impostor syndrome, achieved strong success in hiring negotiations, and gained frameworks for accountability and strategic planning that I use daily. If you're an engineering leader transitioning to larger organizations or building systematic approaches to leadership, Alessandro is exceptional. He combines Silicon Valley wisdom with the patience of a true teacher.” Read more Show less

Roman

Standard Plan · 2 months

“Alessandro is a really open minded and patient mentor. Our sessions started with my intention of getting more exposure into management by talking to someone with more experience, but in the end I achieved not just that,…” “Alessandro is a really open minded and patient mentor. Our sessions started with my intention of getting more exposure into management by talking to someone with more experience, but in the end I achieved not just that, but also a better understanding of the different skills and topics needed to learn to perform my role better and continue my career path. His style is very personal, he patiently listened to my questions and dove into clarification before answering. He really tries to make his answers clear and as close to the core of the question asked regardless of the subject. His experience is very extensive too, allowing us to discuss a wide range of subjects, so I feel like I got more than one mentor in one. ” Read more Show less

Fernando

Standard Plan · 7 months

“I reached out to Alessandro after relocating from Switzerland to Boston, knowing that navigating the US job market would be a whole new challenge. He turned out to be exactly the support I needed. Alessandro helped m…” “I reached out to Alessandro after relocating from Switzerland to Boston, knowing that navigating the US job market would be a whole new challenge. He turned out to be exactly the support I needed. Alessandro helped me adapt my CV for the US market, pointed me to the right job platforms, ran mock technical interviews with me, and gave really valuable feedback on my take-home assignments. He was thorough, responsive, and genuinely invested in helping me succeed. Thanks to his guidance, I was able to land a job offer and feel confident throughout the process. I'd highly recommend Alessandro to anyone!” Read more Show less

Patrick

Lite Plan · 4 months