Business Management
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Obsession for Perfection: lessons from misfit leaders who’ve changed the game

Excellence looks great from the outside but it’s a rigorous process of being consistent and practising your values and principles every day. Explore how misfits like Steve Jobs, Jeff Bezos, Dara Khosrowshahi, and more redefined each day as Day 1, constantly innovating and challenging norms. We unravel some actionable stories and strategies of innovation and customer obsession that shaped Apple, Amazon, Uber, and Airbnb.


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The world's greatest founders share an obsessive focus on the problem they're solving and the experience they want to create. Behind their success lies a rigorous daily commitment to core principles - treating each day as "Day 1" through an unwavering beginner's mindset.

True customer obsession demands more than platitudes about delighting users. It requires a culture of empathy, immersion in the customer experience, and relentless dedication to eliminating friction through obsessive attention to detail. The so-called misfits who change industries make the unusual unusually good. Here’s a look into how some iconic founders institutionalised profound customer focus.

Staying Beginners 

The secret sauce behind Apple’s products and experience was simply starting with the customer experience and going backward or adopting the first principles approach. The mantra seems simple but Steve Jobs was obsessed with creating beautifully designed simple products that anyone can use and would recommend to one’s friends and family. Tony Fadell (Father of the iPod) narrated a testament that shows Jobs’ conviction to this: 

Steve introduced a concept for himself and all Apple employees called Staying Beginners - to come in each day and see their own products through the eyes of their customers, “The one that has fears and possible frustrations and hopeful exhilaration that their new technology product would work straightaway for them.” This was an everyday exercise of focusing on those tiny little details to make them faster, easier, and seamless for the new customers.

The results of this were slow, small, sometimes absolutely micro improvements that compounded big time eventually. 

In the 1990s, purchasing a new personal technology product was often an exercise in delayed gratification. After saving up money over months or years, customers faced an additional frustration upon opening the box - a "Charge before use" sticker, forcing them to wait even longer before experiencing their prized acquisition. However, Jobs' obsession with crafting an unparalleled customer experience led Apple to eliminate this pain point entirely. All Apple devices were designed to come fully charged straight out of the box, allowing customers to dive right into the transformative experience as soon as they made their purchase. By going to such lengths to delight users at every step, Apple set a new bar for the industry. This painstaking commitment to enhancing the entire customer journey, no matter how small the detail, embodied Apple's user-obsessed philosophy and became the standard others had to match.

Apple made sure consumers never had to wait to use their new products.

Again, without deep care and intent this might have gone unnoticed, as was the norm. A misfit cared enough to change this. 

What True Customer Obsession Looks Like 

  • Amazon's vaunted "Day 1" culture of customer obsession has been reinforced over 30 years of growth to a $1.9 trillion market cap. To keep leaders grounded in the customer reality, Amazon employs an unusual practice: Every two years, all senior executives, including the CEO, spend two days training in customer service call centres - attending calls directly. 

To exemplify more on this philosophy, Jeff Bezos introduced the ‘empty chair’ strategy in all meetings. This involved leaving an empty chair at the conference table to symbolise the most important person in the room: the customer. Jeff even kept his email public for customers to reach out and had a notorious habit of sending a single-character email forward to his executives to solve those immediately.

  • Uber’s ‘Project Boomerang’ is another one for the tale that almost got its CEO Dara Khosrowshahi killed while on the road as an Uber driver. The project went on for months with him moonlighting as a driver to understand more about the ‘experience of being a driver’ and how to attract more customers to the app. Through the effort Khosrowshahi experienced many common Uber driver complaints, including harassment from riders, anxiety over maintaining a high rating, and a frustrating sign-up process.

The experience resulted in “Re-examining every single assumption that we’ve ever made.” he said, and changed the course of the company.

Uber CEO Dara Khosrowshahi on the streets
  • AirBnb’s office was an apartment where the whole team lived and worked together. As Brian Chesky says, they wanted to completely immerse themselves in building a culture that’s truly representative of what they’re building. Brian to this day lists out his personal home on AirBnB to exemplify their ‘host-centric’ approach and deliver the experience he would himself want and envision. 

P.S. You can book Brian’s lovely apartment here.

Going Beyond

A maniacal focus on enhancing the entire customer journey, obsessing over even the smallest details, forged deep loyalty that propelled transformative visions forward. What seemed unusual ultimately became the new normal. As Steve Jobs remarked, "You can quote them, disagree with them, glorify or vilify them, but the only thing you can't do is ignore them because they change things."

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