Attention To Details

Why the little things matter

Willie Sutton, one of America’s most infamous bank robbers, captivated the public with his audacious heists and sharp wit. Born on June 30, 1901, in Brooklyn, New York, Sutton grew up in a working-class neighborhood. Although his childhood appeared unremarkable, Sutton displayed a natural aptitude for crime early on. His career as a bank robber spanned over four decades, during which he reportedly stole millions of dollars and achieved legendary status.

Sutton’s moniker, "Slick Willie," was earned through his meticulous planning and ingenuity in avoiding capture. Known for his disguises, he often posed as a postal worker, a policeman, or even a maintenance man to gain access to his targets. His attention to detail and ability to think several steps ahead made him a formidable adversary to law enforcement. When asked why he committed such crimes, Sutton quipped, “Because that’s where the money is.”

He also famously stated, “Success in any endeavor requires single-minded attention to detail and total concentration.” This philosophy, while unexpected from a career criminal, holds profound truth for any field of work or endeavor. Sutton’s meticulous preparation underscored his ability to anticipate challenges, exploit opportunities, and avoid costly mistakes. His life of high-stakes crime, though far from virtuous, illustrates the power of paying close attention to the little things.

I’ve written before that if I do have a superpower it is long-suffering. I think the military taught me that, among lots of other things. On the opposite side, of the many weaknesses that I have, the one that stands out for me is attention to detail. By nature, I am much more of a broad-stroke, big-picture type of person. The details bore me. If this is a surprise, then I’ve done my work properly. I have mostly been an advocate for doubling down on your strengths since you enjoy them more and your return on the investment of effort is much greater. However, I have backed down on that stance a bit and admitted that if a weakness was holding you back, you have to focus on improving it. This is what attention to detail was for me.

“Details make perfection, and perfection is not a detail.” – Leonardo Da Vinci

As you might expect, the military is pretty big on attention to detail. I’m sure lots of other professions where people’s lives are on the line such as medicine are as well. I’ve found software engineering is very tolerant of lack of attention to detail, in part because of the iterative nature of code, test, code, test, etc. A thread on Reddit from a couple years ago mentioned that “getting good at TDD [test driven development] is a godsend for this.” While I never put this all together, it makes perfect sense that this is why I’m a big fan of paired programming and test driven development. Two sets of eyes are better than one and I know when it’s done because it passes the tests. Or, all of this could explain why I’m not a very sought after software engineer.

In my early years in the military it was repeatedly pointed out to me, in the form of pushups and other punishments, that I lacked this important skill of attention to detail. I hated this. I hated that others around me had such fine attention to detail and I didn’t. At some point I vowed to work on this. Now, many decades later, I’m pretty decent at paying attention to the details. I’ve trained myself so much in this regard that it irks me to no end if I miss something small like a typo in an email or misspell someone’s name. I’m also not super tolerant of others in this regard either.

However, in the world of software engineering, there’s a built-in tolerance for imperfection. Iterative processes like test-driven development (TDD) and agile methodologies allow for a certain degree of trial and error. You write code, test it, and refine it until it works. This approach reduces the immediate penalty for missing a detail, creating an environment where small oversights are less catastrophic than in, say, aviation or medicine.

“Details matter. It's worth waiting to get it right." – Steve Jobs

However, even in tech, the stakes can quickly rise. A poorly reviewed pull request can lead to security vulnerabilities. A misunderstood analysis can result in wasted development cycles or a product that misses the mark. Software engineering tolerates some error but only up to a point.

In other business disciplines, the margin for error is far smaller. A misplaced decimal in a financial forecast, a misinterpreted clause in a contract, or an oversight in a compliance document can lead to reputational damage, financial loss, or even legal repercussions. These are areas where attention to detail isn’t just valuable, it’s critical.

The world doesn’t reward grand ideas when their execution falters on the details. So, I made a deliberate effort to improve. Over years of practice, I developed systems and habits to mitigate my natural blind spots, from leveraging tools like checklists to embracing collaborative methods like paired programming. Attention to detail became not just a necessity but a personal point of pride. Here are a few practices that have helped me and others improve:

Embrace Checklists: Pilots, surgeons, and astronauts all use them for a reason. Checklists reduce cognitive load and ensure you don’t overlook the basics, even under pressure.

Collaborate Intentionally: Two sets of eyes are better than one. Whether through paired programming, peer review, or simply having a trusted colleague double-check critical work, collaboration helps catch what you might miss.

Develop Structured Routines: Attention to detail thrives on predictability. Establish habits for reviewing your work, whether it’s rereading emails before sending or double-checking numbers in a spreadsheet.

Seek Feedback: When others point out mistakes you’ve missed, don’t bristle, learn. Over time, you’ll start to notice patterns in your oversights and can work to address them.

Mastering attention to detail doesn’t mean abandoning your big-picture thinking. Rather, it’s about integrating the two. When you combine strategic vision with precise execution, you create a powerful advantage. Leaders and teams who excel in this balance are trusted, not just for their ideas but for their ability to deliver on them flawlessly.

Steve Jobs, co-founder of Apple, was legendary for his obsession with detail, a trait that shaped the company’s ethos and its products. One telling example was his insistence that the inside of the Macintosh computer be as meticulously designed as its sleek exterior, even though most users would never see it. Jobs worked closely with engineers to ensure the internal circuit boards were neatly laid out and aesthetically pleasing, believing that craftsmanship should be consistent, even in unseen aspects. “For you to sleep well at night, the aesthetic, the quality, has to be carried all the way through,” he said. This relentless focus on perfection didn’t just create beautiful products, it inspired a culture of excellence that set Apple apart, making its devices icons of innovation and design.

As Sutton, Jobs, and many others’ lives demonstrate, success, no matter the field, requires focus on the small things. Attention to detail is not just about avoiding mistakes; it’s about building trust, reliability, and a reputation for excellence. The world may admire the dreamers, but it rewards the doers who get the details right.