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  • benjaminnewman01

Mod 2.1 - Reflections on Progressive Leadership

Updated: Jul 28, 2023

Corporate Rebels describe progressive leaders as stated below:

Be supportive of those ‘closest to the fire’. They constantly challenge the status quo – the way we’ve always done things – and encourage the entire organization to do the same. These leaders walk the talk. They embody organization mission and values. They are crucial to an organization’s culture. They do everything in their power to remove barriers. They help their employees thrive. Authority is no longer linked to rank, but rather to the ability to lead by example.

Corporate Rebels The 8 Trends

1. From Profit to Purpose & Values

2. From Hierarchical Pyramid to Network of Teams

3. From Directive Leadership to Supportive Leadership

4. From Plan & Predict to Experiment & Adapt

5. From Rules & Control to Freedom & Trust

6. From Centralized Authority to Distributed Decision Making

7. From Secrecy to Radical Transparency

8. From Job Descriptions to Talents & Mastery

Write a reflection in your journal based on the following prompts.

  • How do you approach leading?

  • Do you consider yourself a ‘progressive’ leader as described by Corporate Rebels? Why?

  • Have you experienced progressive leaders or been influenced by extreme command and control?

  • What informs your assumptions, mindset and thinking about how to lead transformation?


As far back as I can remember, I’ve tried to approach my own expression of leadership as a servant leader. I’ve interviewed and worked for some of the best and most progressive restaurants in the country including Eleven Madison Park and Union Square Café in NYC. At Eleven Madison Park, every front of house staffer begins in the same role and then works their way up the ladder, including the General Manager. One of the many reasons for this practice was to show staff looking to move up what qualities and habits their coworkers embodied that allowed them to advance so they could learn them as well. Similarly, a Server’s Assistant (the entry level role everyone starts at) couldn’t say the GM didn’t understand the intricacies and nuance of their job, because that person, and everyone above them had all held the job at one point.

The 8 Trends shared by Corporate Rebels embody many of the characteristics I’ve aimed to apply in each of my roles in different nonprofit organizations and reflect the values that contributed to some of the cognitive dissonance I’ve experienced in those roles. For example, moving “From Profits to Purpose & Values” makes sense operationally in a nonprofit where earned revenues only generate between 15-30% of total annual revenues. It never made sense to me that the dominant reason to say “No” to an idea or new initiative was because it didn’t generate profits, especially when development efforts depend on building donor relationships through meaningful experiences, numerous touchpoints and opportunities for engagement by modeling the company’s mission, purpose and value in order to retain the donor’s current investment and hopefully increase their annual giving.

I could speak to my experience of The 8 Trends Corporate Rebels has identified, but instead I’d like to pushback on their framing of Trend #4: “From Plan & Predict to Experiment & Adapt”. I don’t believe the principle is bad, but in comparison to the other trends, I don’t think the “From - To” matches the other trends identified. In my experience, most nonprofits are very bad at planning and predicting, or if they are good at it, it’s certainly not organizationally shared and understood in a tangible way that impacts the company holistically either positively or negatively. To be fair, they aren’t good at experimenting or adapting either, but that’s where I believe the framing doesn’t match the other trends shared.

I would argue that most nonprofits need to move “From Being Reactive to Being Proactive”. Some orgs already may practice being proactive within specific departments, but it’s not practiced by all departments or integrated throughout the entire company. As a result, some departments require the full attention of all of their staff to respond to a crisis or problem, which slows down their entire operational capacity, the impact of which bleeds into other departments, who may be better practiced at responding to crises proportionally as a result of being proactive but nevertheless are slowed down by the weight of reactive departments. Another example I’ve seen is when a company’s leader is reactive and department directors are proactive. No matter how practiced they are in responding to the leader’s reactions, inevitably their impact is significantly reduced because of the amount of attention they have to give to respond to the leader’s reactionary tendencies.

Putting poor examples aside, I’d also argue that experimentation and adaptation are values that are applied within the framework of planning and predicting. Experimentation doesn’t mean trying new things spontaneously or without buy-in from others. Similarly, in order to adapt, a company must first identify the areas in which they are currently ill-prepared to address if a large crisis emerges. That process requires planning and predicting based on existing metrics in order to demonstrate what adapting to a crisis would look like.

I’ve been influenced by both progressive leaders and extremely controlling ones. Danny Meyer, whose seminal text Setting The Table has been adopted by numerous corporations describes how to move from a “Top-Down'' hierarchy to “Bottom-Up” and the organizational value it provides including greater freedom and trust of staff. For example, while working at Union Square Café as a server, I was given the freedom to offer an “SFN” or “Something For Nothing” to my guests. This was a complimentary dish, beverage, or dessert that we could order for a table, no questions asked. Some servers would take regular advantage of the opportunity to try and increase their tip percentage, understandably so, but I chose a more intentional approach. First, I knew I didn’t need to rely on a complimentary element in order to generate a high tip percentage. Second, by only utilizing the resource sparingly I would proactively build in the time to spend at the table to share why they were receiving an SFN. In practice, how I used it was very simple. If a guest was wavering between two choices on the menu, and I knew that I could offer one of the choices as an “SFN” without having to justify it to Chef or management, I would encourage them to order the other option and simply add the second one to their order. Then when the food would arrive and they would see both options in front of them, they would express their delight and how meaningful it was to them.

By contrast, I’ve had so many poor bosses who lack any semblance of progressive values and are paralyzed by fear of anything outside of the status quo that they spend the majority of their work time focused on maintaining and mitigating any appearance of change that the company they manage stays perpetually the same regardless of the corporate, cultural, and generational changes occurring outside of their organization. As a result, they stop attracting talent at both the board and staff level and eventually appear to the majority of the public like an ancient vestige of a prior era that will eventually close its doors and then wonder what went wrong.

My mindset and thinking around how to lead transformation is informed by the combination of my previous experiences with success and failure. Looking at the examples above, the principle of an “SFN” has inspired me to adopt a practice of “Going Above and Beyond” in the area of customer service. What this looks like in practice is training staff to listen closely to what customers are telling them and how to respond in real time. It also means not simply correcting a mistake, but going the extra mile to demonstrate to the customer that we don’t want them to just think “They fixed the mistake I shared with them” but “They fixed the mistake I shared with them and they offered to give me free tickets to the next concert” or “They fixed the mistake I shared with them and they offered to comp my entire meal the next time I made a reservation.”

Conversely, I’ve had so many poor experiences of leadership in the nonprofit sector that I encourage younger colleagues at the beginning of their careers to use the experience as an opportunity to learn “how not to lead or run a company.” Sadly, I would say that most of the experience I’ve gained in my career has been more about “what to avoid” than “what to do” in order to be successful. That said, by not imitating or repeating the models I’ve seen, I believe I’m better positioned to lead transformation because I have seen so many poor examples of maintaining the status quo that I can identify them quickly and begin leading change more rapidly.

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