Reflections on 100 Newsletters

Leadership, Innovation, Failure, and Culture

This marks the 100th edition of Fish Food for Thought. According to a recent study, if this were a podcast, it would be among the top 1%, as 90% of podcasts don’t make it past the third episode, and 90% of those remaining quit after 20 episodes. Alas, this isn’t a podcast. However, while there are a staggering 1.7M newsletters on Substack and LinkedIn, only 12% of them have published new content in the last 45 days. Apparently, only 35% of newsletters make it to two issues. While this newsletter isn’t generating $5M in annual subscriptions like Letters from an American, partly because it’s free and partly because she has 320x more subscribers, I’m grateful for this platform to share thoughts and spark meaningful conversations.

This all started as a weekly internal newsletter that I wrote to share highlights of team members’ accomplishments. The org was starting to get large and not everyone knew what other teams were doing. A weekly newsletter seemed to be the solution. Eventually folks got tired of writing up their accomplishments and I didn’t get tired of writing introductions, commentary on various topics, or general thoughts I wanted to pass along. As I’ve mentioned before, if I have a super power it probably is long-suffering, but writing isn’t suffering for me. I enjoy the act as it helps clarify my thoughts. More on that in a future newsletter. 

I didn’t want this milestone to pass unmentioned but I also wanted to reflect back on some topics that have been discussed. I spend a lot of time thinking how I can improve. I try to ask myself after every major meeting, presentation, decision, etc. ‘How could I have performed better?’ This fascination with retrospectives, after action reports, and postmortems started in the military and has continued through my years in tech companies. This is part of most organizations' DNA, especially when things go wrong but the best teams do it all the time. 

So, I thought today’s newsletter could look back at some of the most impactful topics we've explored, and solicit a little feedback. I started this thinking that the categories of content were going to be People, Process and Technology since that is a framework that I commonly use. After almost two years of newsletters, the broad categories from the past turned out to be: Leadership, Innovation, Failure, and Culture. Let’s review.

Leadership

Leadership is not merely about directing others. It's about understanding the right balance between decisiveness and adaptability. The newsletter titled "Right Person, Right Role, Right Time" delves into the concept that leadership is contextual. A CEO who thrives in the chaotic environment of a startup may not necessarily succeed in a more mature, structured organization. The key lesson here is that leadership is fluid. The best leaders recognize when their approach needs to change as the company evolves. They are not rigid in their methods; instead, they understand that different phases of a company’s growth require different leadership styles.

Listening is another critical component of effective leadership. In the article "Listen or Speak?" the discussion centers on the importance of listening more than speaking. Drawing inspiration from leaders like Nelson Mandela, the newsletter emphasizes that those who listen first are often the most effective. Mandela’s approach of letting others speak first not only allowed him to gather more information but also fostered a culture of inclusion and respect. The lesson here is clear: effective leadership is as much about listening as it is about making decisions. By listening actively, leaders can make more informed decisions and create a more collaborative environment.

Creating an engaged culture is another hallmark of great leadership. Jim Collins' triangle of service, growth, and communal success, as discussed in the "Square of Happiness" newsletter, offers a framework for building such a culture. Collins suggests that meaningful work stems from these three elements—service to a greater cause, personal and professional growth, and the pursuit of communal success. A leader who fosters these elements in their organization creates a workplace where employees are not only productive but also deeply connected to their work. This connection leads to higher levels of engagement, satisfaction, and ultimately, success.

Yet, leadership is not just about guiding others, it’s also about self-awareness. In "The Fallacy of Self-Made," the newsletter challenges the myth of the self-made leader. It highlights the role of luck, timing, and external support in any leader’s success. Recognizing these factors fosters humility—a crucial trait in leadership. By acknowledging that success is not solely the result of personal effort, leaders can stay grounded and focus on what truly matters: continuing to grow and support their teams. The lesson here is that humility allows leaders to remain connected to their teams and grounded in reality, which in turn makes them more effective.

Innovation

Innovation is the engine that drives progress, and fostering it requires a deliberate and positive approach. In the newsletter "Hope: A Different Kind of AI," the concept of Appreciative Inquiry is explored. This method, which focuses on strengths rather than weaknesses, provides a powerful framework for innovation. By starting from a place of positivity and building on what is already working well, organizations can inspire their teams to imagine and create a better future. The lesson here is that innovation thrives in environments where strengths are recognized and possibilities are explored without the burden of constant criticism.

The importance of leveraging existing assets for innovation is highlighted in "Brand & Data: Strategic Advantages for Web 2.0 Companies." The discussion centers on how data and brand can serve as powerful differentiators in the Web 2.0 era. Companies that successfully leverage these assets can create a strong defensive moat against competitors. For example, Amazon’s mastery of data allows it to offer personalized shopping experiences that keep customers coming back, reinforcing its brand and market position. The lesson here is that innovation is not just about new products or services, it’s also about how existing strengths can be used in new and creative ways to maintain a competitive edge.

In the realm of ecommerce, the newsletter "The Future of Ecommerce" predicts the transformative impact of generative AI on the industry. GenAI is expected to replace traditional search and recommendation engines, fundamentally changing how consumers interact with online retailers. This shift will require companies to rethink their strategies and adapt to new technologies quickly. For example, by integrating customer experiences across channels, businesses can create seamless, personalized shopping journeys that increase customer satisfaction and loyalty. The lesson from this is that staying ahead of technological trends is crucial for innovation. Leaders must anticipate these changes and prepare their organizations to embrace them, ensuring that they remain competitive in a rapidly evolving landscape.

Failure

Failure, though often seen as a setback, is an essential part of growth and learning. This newsletter has consistently emphasized that embracing failure is crucial to building resilient and successful organizations. In "Learning From Failure," the idea that every failure presents an opportunity to learn is front and center. The article also advocates for the use of blameless postmortems and failure workshops as tools for extracting valuable lessons from mistakes. These practices ensure that failures are not repeated and that the organization grows stronger with each setback. The underlying message is that failure should not be feared but embraced as a learning tool. By systematically analyzing what went wrong and implementing changes based on those insights, organizations can turn failures into stepping stones for future success.

The cautionary tale of Knight Capital underscores the importance of learning from others' mistakes as well. Knight Capital’s catastrophic software glitch, which resulted in a $440 million loss in just 45 minutes, serves as a stark reminder of the consequences of not thoroughly testing changes before deployment. However, the company’s transparency in sharing the details of their failure has provided invaluable lessons to others in the industry, helping to prevent similar incidents elsewhere. The lesson here is that sharing failures openly not only helps the organization learn but also benefits the entire industry, fostering a culture of shared knowledge and continuous improvement.

The story of the Space Shuttle Columbia disaster highlights the dangers of complacency and over-reliance on past successes. NASA’s failure to adequately address known issues led to one of the most tragic accidents in space exploration history. However, the disaster also led to a complete overhaul of NASA’s culture, emphasizing better communication and error reporting. The key takeaway is that success can sometimes breed complacency, which can be just as dangerous as outright failure. Organizations must continuously question their processes and be open to change to avoid similar catastrophes.

The newsletter titled "Failure" delves deep into the importance of not just accepting failure, but actively learning from it. It highlights that failure should not be seen as a final verdict but as a stepping stone toward improvement. The idea is that every failure contains valuable lessons that can guide future actions. This mindset encourages a culture where employees are not afraid to take risks, knowing that even if they fail, the experience will contribute to the organization's collective knowledge. By creating an environment where failure is discussed openly and without blame, companies can foster innovation and prevent the same mistakes from being repeated. The key takeaway is that failure is not just an obstacle—it’s an opportunity for growth.

Similarly, the "Embracing Failure" newsletter builds on this concept by discussing the psychological and cultural aspects of dealing with failure. It underscores the importance of cultivating a culture where failure is not stigmatized but embraced as a natural part of the learning process. The article argues that when leaders demonstrate a willingness to embrace failure, it sets a powerful example for the rest of the organization. This openness encourages employees to experiment, innovate, and push boundaries without the paralyzing fear of repercussions if things go wrong. The lesson here is that embracing failure can actually lead to greater creativity and innovation, as it allows individuals and teams to explore new ideas without the fear of failure holding them back.

Culture

Culture is the invisible hand that guides an organization, shaping how its members interact, make decisions, and ultimately succeed or fail. It’s the force that binds people together, influences behavior, and ultimately determines success or failure. The foundation of a strong organizational culture often begins with hope. As discussed in the "Hope" newsletter, hope is a powerful, yet often overlooked, force in driving organizational success. Hope isn't just an abstract concept, it's a tangible energy that propels teams forward, especially during challenging times. When employees believe that their efforts will lead to positive outcomes, they are more likely to be engaged, innovative, and resilient. A culture infused with hope inspires optimism and forward-thinking, creating an environment where employees are motivated to overcome obstacles and push the boundaries of what’s possible. The lesson here is clear: leaders should cultivate hope within their organizations by setting a vision for the future that is both ambitious and attainable, giving employees something meaningful to strive for.

While hope is crucial, reputation also plays a significant role in shaping team culture, as highlighted in the "Reputation and Team Culture" newsletter. The reputation of a team, both internally and externally, can influence everything from collaboration to performance. A team known for its integrity, reliability, and excellence will naturally attract top talent and foster a sense of pride among its members. Conversely, a poor reputation can lead to disengagement and conflict. Building and maintaining a strong team reputation requires consistent behavior that aligns with the organization's values. Leaders must model these behaviors, ensuring that their actions reinforce the desired cultural norms. This alignment between behavior and reputation creates a positive feedback loop, where a strong reputation further strengthens the team culture, and a strong culture, in turn, enhances the team's reputation.

The broader concept of culture is explored in the newsletter simply titled "Culture," which delves into the idea that culture is the sum of the behaviors, values, and beliefs that are practiced within an organization. Culture is not what is written on the wall or in the employee handbook; it’s what happens when no one is watching. It's shaped by the everyday actions and decisions of everyone in the organization, from the CEO to the newest intern. A strong culture acts as a guidepost for behavior, influencing how employees interact with each other, how they approach their work, and how they respond to challenges. The lesson here is that culture must be intentionally cultivated through consistent practices that reinforce the values and behaviors the organization wishes to embody.

Creating a culture of excellence requires deliberate effort, as discussed in the "Cultivating a Culture of Excellence" newsletter. Excellence doesn’t happen by accident, it’s the result of intentional practices that push individuals and teams to perform at their best. This newsletter emphasizes the importance of setting high standards, providing the necessary resources and support, and fostering an environment where continuous improvement is valued. In a culture of excellence, employees are encouraged to take ownership of their work, strive for high-quality outcomes, and hold themselves and others accountable. Leaders play a critical role in this process by setting the tone and expectations for excellence and by recognizing and rewarding behaviors that align with these high standards. The key takeaway is that excellence should be woven into the fabric of the organization, becoming a natural and expected outcome of everyday actions.

However, maintaining a strong culture isn’t without its challenges, particularly when it comes to peer conflict, as discussed in the newsletter "Peer Conflict." Conflict is inevitable in any team, but how it’s handled can either strengthen or weaken the culture. Healthy conflict, where differing opinions are expressed and resolved constructively, can lead to better decisions and stronger relationships. However, when conflict is mishandled, when it becomes personal, divisive, or is left unresolved, it can erode trust and undermine the team’s cohesion. The article highlights the importance of creating a culture where conflict is addressed openly and constructively. This involves setting clear expectations for behavior, providing training on conflict resolution, and ensuring that leaders model the right way to handle disagreements. The lesson here is that conflict, when managed well, can be a powerful tool for growth and improvement, but when mishandled, it can be corrosive to the culture.

As Fish Food for Thought hits this milestone of 100 editions, I invite you to share your thoughts on the topics we've explored together. Which discussions resonated most with you? Are there areas where you'd like to dive deeper or new subjects you'd like to see covered? Your feedback is invaluable in shaping the future direction of this newsletter. Whether it’s reflections on leadership, innovation, failure, or culture, I look forward to hearing how these insights have impacted your thinking and what you'd like to explore next. Here's to the next 100 editions and the ongoing journey of learning and growth.