My Favorite Mistake — 235: The Art of Overcoming Mistakes at Work: Lessons from Cliff Hazell

Episode page with video, transcript, and more

My guest for Episode #235 of the My Favorite Mistake podcast is Cliff Hazell, a leadership coach and startup advisor, formerly of Spotify.

Cliff has made a career out of breaking down the obstacles that stand in the way of great work. He is often challenging the status quo in his quest to develop the right culture and systems for creation of excellent Companies and Products.

After a tour of addresses across South Africa, Cliff moved to Stockholm where he led a team of Coaches at Spotify for 4 years. Now he helps Scale-ups remove their Growth pains, enabling to Create Focus, Find Leverage, and Build Habits.

He was my guest on the Lean Whiskey podcast, episode #19, back in August, 2020.

In this episode, Cliff shares his favorite mistake story about a time when he got some “fairly brutal feedback” about his normally direct style of communication. Why did that knock his confidence back for a few months? What did he learn and how did he adjust?

Questions and Topics:

  • Decision to work on yourself vs. finding a better fit?
  • What did you learn about this? Moderate it? Finding more of your self confidence again?
  • 2 insights that really helped him
  • I’ve interviewed two former Spotify people (Ward Vuillemot and Kevin Goldsmith). How would you characterize the culture of learning from mistakes there?
  • Reflections on your time at Spotify?
  • Balancing autonomy and alignment?
  • Avoiding a mistake at one extreme or another?
  • Habits – James Clear — Atomic Habits
  • Flight Levels Academy — founder and still a little involved

Navigating Mistakes in Professional Career: Learning from Cliff Hazell

Among the most accomplished careerists, few can match Cliff Hazell, renowned for his relentless pursuit of great work and his ability to overcome challenges frequently faced within professional environments. With a knack for challenging conventional wisdom, he is known to erect and nurture suitable cultural environments and systems necessary for excellent company and product development. In his quest to bring out the best in organizations, his journey has seen him rise from the beautiful landscapes of South Africa to bustling Stockholm.

While in Stockholm, Cliff led a team of coaches for Spotify for a noteworthy four-year period. His current pursuit includes aiding ‘scale-ups’, organizations seeking to expand their operations smoothly. His role often involves assisting these companies in addressing growth pains, enabling them to focus, identify leverage, and establish professional habits.

However, success was not always a given. Cliff, like every other person, has had to grapple with various mistakes in his professional journey. Among these, one stands out as his ‘favorite’. It offers a profound learning experience.

Cliff Hazell’s Favorite Mistake

Cliff’s favorite mistake occurred in the course of his usual work, which is often characterized by a very direct approach. Notably, this happened while working with a team at Spotify. This well-established team occasionally found itself entangled in circular debates which hampered progress and productivity. At one point, during an in-depth discussion about recruitment, Cliff lost his cool. His outburst, rather than causing the needed improvement, left an uncomfortable rift within the team. This mistake provided a valuable lesson about considering the potential impact of one’s reactions in such contexts.

Insights from the Mistake

In the aftermath of this episode, Cliff felt his confidence knocked considerably. He receded from being actively involved in various projects. This experience made him realize that overconfidence can easily lead one to make rash decisions that may not yield the intended result. However, under-confidence can also be problematic as it can prevent one from taking important initiatives.

To become more effective at handling such situations, Cliff engaged the help of a coach. Over time, he learned to assess the situations accurately, prepare himself accordingly, and deliver an appropriate response. All these actions have since become key aspects of his professional approach.

Another learning point for Cliff was the need to understand and take into account what other people are looking for in a particular situation. This realization made him shift his focus towards meeting people where they are, asking pertinent questions that would guide them towards the right direction.

Reflecting on the Spotify Culture

Spotify is known to have a culture that fosters learning from mistakes. Despite facing challenges from time to time, Cliff affirms that Spotify generally excels at continuous learning. The company’s culture embraces agile implementations at a frequency and cadence rarely seen in other organizations.

However, Cliff cautions about the common desire to visit or join companies for their perceived ‘perfection’. He insists that no company is perfect but rather, each has its unique set of challenges and opportunities. Instead of seeking perfection, he suggests people think about the types of problems they enjoy working on and find a company that provides such challenges.

From Overcoming Mistakes to Developing Professional Habits

Over the course of his impressive career, Cliff Hazell has found that overcoming mistakes and embracing growth opportunities often leads to the development and strengthening of professional habits. The experiences gained from these lessons, particularly the insights from his favorite mistake at Spotify, have informed Cliff’s coaching approach and ultimately paved the way for his work in aiding ‘scale-ups’.

Considering Occupational Preferences and Company Culture Dynamics

One important lesson that Hazell shares involves scrutinizing one’s preferences in selecting an appropriate work environment. He encourages an in-depth consideration of the challenges one enjoys working on and advises positioning oneself in an environment that offers similar scenarios. For instance, if one prefers a structured system with defined roles and responsibilities, a more corporate, scaled company may be appropriate. Alternatively, if an individual dislikes that structure, a startup setting may be more fitting. In any case, reflection and self-assessment play vital roles in identifying one’s preferred working environment.

Moreover, the balance between autonomy and alignment in a company’s culture is a key dynamic to consider. Drawing from his experiences at Spotify, Hazell elaborates on the unique challenges a rapidly scaling company faces. For instance, he observed that while excessive autonomy could lead to a lack of alignment, stifling rules could also inhibit innovation and growth. In essence, an appropriate balance is essential to foster a productive professional environment.

The Pursuit of Balancing Autonomy and Alignment

Finding the perfect balance between autonomy and alignment is not a straightforward task. It tends to involve much trial and error, as a move to the extreme of either end could be problematic. However, according to Hazell, the key lies in the ability of the company to adapt and correct its course.

One interesting point that Cliff raises relates to the challenges associated with an overabundance of autonomy. This can create a situation akin to herding cats, causing the company to spread its resources too thin and dissolving its cohesion. On the flip side, rigorous alignment can lead to a lack of space for innovation and creativity.

Many organizations toggle between these two extremes, leading to expensive restructuring and transformational shifts. The question of autonomy and alignment is best addressed by a careful evaluation of both aspects and a thorough discussion regarding the computations of moving too far in either direction.

Recognizing High Leverage Points

In the course of his work, Hazell pays keen attention to high leverage points. These are areas that, once addressed, can lead to significant changes within the organization. He argues that the process of finding these points can be simplified by thinking of alignment and autonomy as conflicting points on a spectrum. By focusing on the positive and negative outcomes of both, a company can have a healthier conversation regarding the balance and prevent any abrupt changes that could disrupt the organization’s stability.

Promoting Habit Creation

In recent years, Hazell has cultivated a keen interest in the concept of habits. He stresses that behaviors within a system largely depend on the system itself and recommends introducing appropriate types of frictions to guide behaviors in a desired direction. This could involve removing barriers to innovation or introducing elements that keep the company on its desired path.

Focusing on catalyzing habits rather than procedures can accelerate the process of growth. Additionally, it allows the company to learn from its mistakes in a more systemic way that encourages constructive growth. This, in conjunction with the ability to recognize high leverage points, plays a pivotal role in steering a company towards its goal.

Navigating Various Organizational Stages

The organizational stage that a company is in profoundly affects the dynamics at play. As Hazell explains, the guiding principles used by a new startup with an intentional culture will differ greatly from those employed by a scale-up that has an established, though possibly unintentional, culture.

Understanding these distinctions helps in developing a tailored approach to addressing issues specific to each stage. For instance, a scale-up would focus more on meeting demand effectively, while a new startup would spend more time figuring out what works. As such, the stage an organization is at becomes a determining factor for the nature of the problems to be solved and the solutions to be implemented.


Cliff Hazell’s insights underline the importance of learning from mistakes in professional environments and how these lessons shape professional habits. By considering occupational preferences, examining company culture dynamics, striving for a balance between autonomy and alignment, promoting the creation of habits, and understanding various organizational stages, companies can facilitate growth and continuously develop towards their goals.