Discussion Overview
We read two papers by Sydney Finkelstein this week (2016 & 2018 HBR). In essence, Finkelstein’s research points to a leadership style that transcends traditional managerial roles, emphasizing instead the profound and lasting influence that comes from teaching, personal investment in talent development, and a genuine commitment to fostering excellence and innovation in their teams. This discussion is focused on your views of these “superbosses”. (Edit April 2026: Due to technical issues, the article “Secrets of the superbosses” can also be downloaded
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Questions & Instructions
- Do you have any experience with an individual who may have exhibited a leadership style consistent with a “Superboss” in your current or past role? If so, how did this interaction change your career trajectory? If not, how do you think this would have helped in your career development?
- What skills and competencies from the readings (Superbosses or Best Leaders are Great Teachers) do you find most effective and plan to implement in your current or future leadership role? Explain why you find this skill important for your role and context.
Examples :
There was a situation where I was faced with a superboss style of leadership, and that was during my Operations internship at Amazon. Especially as my first internship, I didn’t know what to expect, but I imagined that I would be doing simple tasks within my position for my manager and not have such a high responsibility for processes within the warehouse I was assigned to. My manager decided that I belonged on the floor in charge of a big portion of the warehouse and a group of associates, all by myself, which was scary as someone who had just gotten there. After getting more comfortable with the discomfort, my confidence was raised in the abilities that I possessed, but were never tested. By the end of the internship, I had felt like I did the job itself and learned things that I would have never learned if I were just stuck in a cubicle working on my project. Finkelstein mentions something similar to the situation I was in, as the idea of step-change growth. This is where leaders give their employees a high level of responsibility to help them develop faster. My perspective changed because of this, and I see myself taking on more opportunities that I find challenging and seeing that as a way to improve. I find that being a teacher rather than just a manager is a competency that I see myself applying to my future role. My life’s purpose is to help people aid their development because that will make me grow as well. In my future role, I know that I will be managing people, and it is important to know that leadership is not just about status but rather the meaningful connections and impact that I will create in the environment I am put in.
Example:
Do you have any experience with an individual who may have exhibited a leadership style consistent with a “Superboss” in your current or past role? If so, how did this interaction change your career trajectory? If not, how do you think this would have helped in your career development?
I have not had direct experience working for a leader I would classify as a Superboss, but I have worked under a variety of managers who each demonstrated pieces of that leadership style. Some recognized my abilities quickly, while others initially underestimated my capabilities. These experiences pushed me to consistently demonstrate my value and helped shape my resilience and work ethic.
One of the most impactful leaders I worked with was a female supervisor who was both positive and encouraging. She recognized my drive and understood that I needed to be challenged in order to stay engaged and continue growing. She gave me the autonomy to restructure operations, hire staff, and implement new processes within the diagnostic center I managed. She also gave me the confidence to be myself, which encouraged creativity and gave me the freedom to take initiative and implement meaningful changes. As a result, the improvements I introduced led to increased performance and overall profitability. Because of this success, she trusted me to extend those same process improvements to other centers, where I trained teams and helped elevate their performance. Although she wanted me to remain with the company, she also acknowledged that the organization was limited in its ability to continue developing my potential. Her support and trust gave me the confidence to believe in my abilities and expand beyond my formal role.
In my experience, I have often taken initiative beyond my formal responsibilities, which has exposed me to different aspects of leadership, including team development and operational improvement. While not all leaders I worked with actively developed my talents, I gained valuable insights from observing different management styles and learned the importance of understanding employees from a more human perspective. All of these experiences (good and bad) have shaped how I approach leadership today.
2. What skills and competencies from the readings (Superbosses or Best Leaders are Great Teachers) do you find most effective and plan to implement in your current or future leadership role? Explain why you find this skill important for your role and context.
One of the most impactful skills from the readings that I really resonated with me is the ability to find unlikely winners” because it challenges traditional ideas of talent and emphasizes potential over credentials or background. Superbosses are willing to take chances on individuals who may not fit the typical mold but demonstrate intuition, drive, or untapped ability. This is especially meaningful to me because I consider myself an unlikely winner. In my experience, I have encountered situations where my abilities were either underestimated or not fully recognized at first. Because of that, I have developed a strong awareness of how much potential can exist in individuals who may be overlooked. I understand firsthand how impactful it is when someone recognizes your capabilities and gives you the opportunity to grow. I believe that some of the most valuable employees are those who bring a fresh perspective even if they lack conventional experience. I have seen how empowering individuals can lead to strong performance and team success.
When people feel seen and valued for their potential, they are often more motivated, engaged, and willing to exceed expectations. By identifying and developing unlikely winners, it can help build a more diverse, innovative, and high-performing team.
Examples:
In my professional experience, I have had the opportunity to work under a leader who demonstrated several characteristics consistent with Sydney Finkelstein’s description of a superboss. In one of my roles within a large manufacturing environment, this leader did not simply assign tasks but invested significant time in developing my decision-making capabilities. Rather than providing direct answers, they challenged me to think critically, justify my assumptions, and take ownership of outcomes. This approach initially felt demanding, but it ultimately accelerated my professional growth by building both confidence and accountability.
This experience had a meaningful impact on my career trajectory. It shifted my mindset from task-oriented to more strategic and cross-functional thinking. I became more comfortable leading supplier negotiations, presenting data-driven insights, and taking initiative across business units. Most importantly, it reinforced the idea that strong leadership is not about control, but about creating other leaders.
From the readings, one of the most impactful competencies I plan to implement is the concept that the best leaders are great teachers. This includes actively coaching team members, providing real-time feedback, and creating opportunities for others to stretch beyond their current capabilities. In a supply chain and procurement environment like mine, where decisions directly affect costs, operations, and supplier relationships, developing capable and confident team members is critical to long-term success.
Another key takeaway is the importance of personalized investment in talent. Superbosses recognize individual strengths and tailor development accordingly. I find this particularly important because teams today are diverse in both skill sets and motivations. Taking the time to understand each individual allows a leader to unlock higher performance and engagement.
Overall, I believe adopting a superboss mindset focused on teaching, empowerment, and high expectations will not only improve team performance but also create a lasting leadership legacy through the success of others.
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