Leadership Tests: How Great Leaders Are Forged

Ryusei Best Hayashi
10 min readOct 29, 2022

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Photo by Jehyun Sung on Unsplash

“What differentiates a good leader from a great leader?”

Some academicians will answer that it is the ability to build and leverage inclusive organizational cultures (Chatman and Cha 2003), while others argue it’s about being a Vital Leader, requiring both direction and force (Bailey 2016). Business people might say it is the ability to be flexible and adapt their leadership style to the situation (Elder 2020). Athletes tend to say it is the ability to perform and make effective decisions under pressure (Durand et al. 2011). Cinematographers argue it is the ability to fuse emotion, intuition and rationality to get out the best in others (Coget et al. 2011). What most leadership studies and theories have in common is that they examine leaders in their prime, once they are already “stars”, instead of examining when they were just starting out or examining leaders at their early stages. The problem with this disparity is that the challenges and attributes that are required differ depending on the stage, thus it’s often inappropriate to apply prime-stage theories to leaders who are still early in formation. After investigating mine and other’s leadership experiences, I recognized that the majority of time good leaders and great leaders are undifferentiable, until they face particular leadership tests. This essay explores the ways in which great leaders handle, and are forged from, leadership tests, focusing on the test of forming the first group of followers, of handling consequential mistakes and poor decision-making, and when novelty fades.

One of the early tests that a leader faces is forming their first group of followers. Recruiting people is technical and easy, but getting them to follow you and be fully-in on your project is very difficult. In spring 2022, I ran for Senator in the ASUC (student government) where I needed to get votes from students by campaigning on campus to be elected. My team of six people and I successfully organized a launch party, and the social media posts promoting our vision for “The Berkeley Dynasty” were making noise on campus. But, the real test occurred during the voting days where me and my team were supposed to message a lot of people asking them to vote for me. In order to win, we estimated that we would need 280 votes where each person had to get 40 votes, and because it’s expected that conversion would be at about 50% to 33%, each person would have to reach out to between 80 and 120 people in 3 days. After my team heard the numbers, three of them left, two of them showed up to 1 meeting and messaged less than 15, and my Chief of Staff messaged 44; they were only half-in with me. Voting days were a test to see if I could hold the team together, get them to believe in our cause, and be motivated to go above and beyond to deliver results. I tried humility — communicating that our past successes were a result of our teamwork and that we can thrive together again — and collaboration — brainstorming all together for ways to win the election. I tried leadership styles like authoritarian — drawing people towards my vision of The Berkeley Dynasty, democratic — crafting a strategy to divide the work together, and pacesetting — pressuring people to send at least 30 messages per day and following up when they didn’t deliver. By the third and last day of voting, I was frustrated that people were spending their afternoons going out with friends or boyfriend/girlfriend while I was in my room messaging; I failed to form my first group of followers. Ultimately, we lost: we got 200 votes and we needed 277 votes.

Reflecting back, one of the causes behind my failure was I assumed that having a “Why” would magically deliver results. My vision was to “Make UC Berkeley be recognized as the Best University in the World for the next 10 years consecutively”, which having read Simon Sinek’s (2019) Start with Why I thought was enough to rally people around me because I had a Why. This experience taught me two things. First, some Why’s are more powerful than others. The problem with The Berkeley Dynasty was that it was not a shared vision: It moved me because getting into Berkeley when so many other Universities rejected me made me feel like I owe and have to give back to Berkeley, but I later learned that other students didn’t feel so attached to Berkeley as me and saw it more as a transition place, which made it difficult to persuade my team to put in the extra effort and to win votes. Second, only recruit people who share and are fully committed to the “Why”. It’s normal that at the early stages most people won’t buy into the Why, it takes time, but everyone in the team must be there because they believe in the cause, and any team members that are there only for the titles or the socials must be cleared away. My mistake was that I wanted to have a bigger team so we could distribute the work more, so I let in people who simply wanted the title of “Director” and to have fun. It’s better to have 1 person who is obsessed with the Why, than to have 10 people who sort of believe in the Why. Moving forward, when forming my first group of followers I’ll devote more time to strengthening the Why, focus on building a shared vision and being disciplined about recruiting believers.

A second leadership test that leaders face is that of handling consequential mistakes and poor decision-making. Authority is the oxygen of leadership. A leader can only inspire others to take action as long as they have the respect, trust and confidence of others because people follow leaders who they admire, feel safe around, and can rely upon. Circumstances such as when a leader makes a poor decision that leads to adverse outcomes can affect their authority, and the accumulation of these can negate a leader’s influence, in which they would no longer be a leader. At 17, I was the Director of the Student Council, and when the pandemic hit, I saw that my friends and my younger brothers were deeply struggling with the new online learning environment. I proposed investigating the mental health impact that online learning was having on students and pinpoint the root causes by doing a survey, in which students could comment on their classes, teachers, classwork, etc. Our teacher advisor was strongly against my initiative and wasn’t open to changing her standpoint, citing the Vice-Principal wouldn’t like our project. I chose to push forward without telling our teacher advisor, and then, against her advice, I met with the Vice-Principal to tell him we could share the results with the administration. The risk and possible repercussions of the results got the Vice-Principal very nervous, and asked that we hand over the survey immediately and the people responsible for the project. I was panicking because if I complied with their demands I could lose authority and my role within the Student Council, and if I didn’t comply I could lose the trust of the administration, which could result in the disintegration of the council and my name would go down in history as the one responsible for it, and our teacher advisor felt betrayed, which could create divisions inside the organization. My decision was to take personal responsibility for the initiative to protect the Student Council from blame, (under the supervision of the Vice-Principal) I prepared a 40 page analysis and recommendations report from the survey results only to be seen by teachers, and I apologized to the teacher advisor to amend the relationship while giving her more ‘say’ in executive decisions. I maintained my position as Director, and the student-first, inclusive organizational culture has continued on in the Student Council even after I left.

Reflecting back, one of the main reasons behind my success in handling my poor decisions was empathy. First, I relied on empathy for understanding the multi-layers of stakeholders that needed to be addressed (Sanchez 2018). It helped me recognize that my solution had to result in a win-win situation for all students, school administration, the Student Council, and the teacher advisor. For instance, I was able to merge the student’s desire to be heard with the Vice-Principal’s desire to maintain negative comments out of sight from the parents by making the survey results only seen to teachers. Second, empathy helped me understand my own anxieties so I could reframe the problems in a way that would reduce the perceived stakes of the situation. By identifying why I was worried about something, I was able to better control my emotions, so I wouldn’t make any rushed decisions, opting for well-thought-out rational actions. Third, I used empathy for communicating the right message at the right time, and to match the tone when delivering the message. For instance, when I met for my “scolding” meeting with the school administration, I started with an apologetic tone and accepted that it was my fault quickly so I could use the rest of the meeting to talk about the relationship moving forward, proposing my solutions and amending the relationship. Ultimately, the integration of internal and external empathetic practices allowed my younger self to not only defuse the problem without getting harmed, but also to elevate my authority as a leader, becoming an exemplary model for the upcoming students.

Lastly, the leadership test that no leader can escape is when novelty fades and people become dubious whether they wish to continue or not. As repetition becomes routine, the initial hype and excitement caused by engaging with something new decreases, and it reaches a peak point where the individual has sufficient experience to predict what the future day-to-day will be like. It’s at that point when a person asks themselves, do I really want to do this for another month/year/decade? What makes this test so difficult is that it repeats itself every now and then: the crisis of the 1st month, the 6th month, the 1st year, the 3rd year, etc. I had been working with my long-time friend at Reach Best extremely well for 6 months. In the middle of the R&D project, when we were mapping out Universities manually, I noticed his levels of engagement had dropped and he suddenly was not meeting the weekly goals. So, I decided to have an open conversation with him where I would only ask questions, listening to understand as opposed to listening to respond. I asked him how he was feeling about the job and the startup, and he replied he was super excited and that his motivation levels were great, but I got a sense that that was not the whole truth. At the end of the meeting, I asked him, “what do you want to do after University?”, and he replied, “I really want to be a researcher, like my grandmother”. My first instinct was to panic because my vision of running the startup with him seemed compromised, but before making any rushed decisions or conclusions I decided to consult my dad who is a business coach. That’s where I learned about the 6th month crisis, he told me it was meant to happen, and the only way to solve it is by doing nothing about it. It was very counterintuitive to me because almost all my business classes and readings on leadership are focused on taking action, and the problem had already elapsed for 1.5 weeks. I continued meeting with him every day, not decreasing my level of enthusiasm, and the next week it was back to normal and he was working better than ever.

In hindsight, one of the main reasons for why I dealt successfully with the test of when novelty fades was patience and faith. To illustrate why it was a success, let’s imagine I actually took action and I decided to confront him about not getting the work done or giving an ultimatum. By confronting him or giving an ultimatum, the message he will hear is that I only care about him delivering results and that I see him as expendable or replaceable. In such a scenario, the first time they might comply with your requests, but they will be left with a notion that you don’t trust them 100 percent. So the second time they have a crisis, which they will, they’ll be expecting that you make a demand again, and thus will be significantly more likely to leave, or start looking to change jobs or group membership. Sometimes the best course of action is to not take action and let the problem resolve by itself. The difficulty lies in accurately discerning that it is this test, and not something different. Great leaders know which battles to fight, and which not to fight.

In conclusion, how emerging leaders deal with leadership tests will shape and determine whether they will become great leaders in the future. In the early stages, leaders will face the test of getting the first group of followers, the test of handling consequential mistakes and poor decision-making, and the test of when novelty fades. Knowing how to build powerful why’s, empathy, patience, and faith are key to successfully dealing with and overcoming these challenges.

Why I wrote it

I originally wrote this essay for my class with Profesor Alex Budak, “Becoming a Changemaker”, and I really liked the insights I gained upon reflecting on my past leadership experiences, so I decided to share it in hopes that other people would also find it insightful.

About me

I’m the Founder and CEO of Reach Best

I’m a Dean’s List student at UC Berkeley

Feel free to follow me on LinkedIn: https://www.linkedin.com/in/ryusei-best-hayashi/

Bibliography

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Chatman, Jennifer A., and Sandra Eunyoung Cha. “Leading by leveraging culture.” California management review 45.4 (2003): 20–34.

Coget, Jean-Francois, et al. “Anger and Fear in Decision-Making: The Case of Film Directors on Set.” European Management Journal, Pergamon, 19 July 2011, https://www.sciencedirect.com/science/article/pii/S0263237311000417?casa_token=Gl7tQxbGy1QAAAAA%3AUIRWQyXSE76wEC1eLS0Ey5iOEZ1EPHBwCygcvmv13SrRhSUZJaufiF8YG3E3zfSWKIWIml1ZRMCa. Accessed 28 Oct. 2022.

Durand, Mark, et al. The Brady 6. YouTube, NFL Films, 2011, https://www.youtube.com/watch?v=o5fdhfVrg1I. Accessed 28 Oct. 2022.

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Sanchez, Patti. “The Secret to Leading Organizational Change Is Empathy.” Harvard Business Review, 31 Aug. 2021, https://hbr.org/2018/12/the-secret-to-leading-organizational-change-is-empathy. Accessed 28 Oct. 2022.

Sinek, Simon. Start with Why: How Great Leaders Inspire Everyone to Take Action. Penguin Business, 2019.

Stebbins, Gregory. “Council Post: Six Keys to Transcendent Leadership.” Forbes, Forbes Magazine, 27 July 2018, https://www.forbes.com/sites/forbescoachescouncil/2017/05/11/six-keys-to-transcendent-leadership/?sh=e62093d7e2da. Accessed 28 Oct. 2022.

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Ryusei Best Hayashi

Founder & CEO of Reach Best | UC Berkeley Dean’s List | Stanford e-Japan Scholar | Harvard Innovation Challenge II Alumnus | CAA Leadership Award Scholar