“Red totes never sit.”
It’s a simple mantra in the warehouse at Sweetwater, an online music retailer in the US. Red totes hold express orders, so they get packed first. Previously, all orders were packed in blue totes, rendering express orders indistinguishable until someone scanned their labels.
It’s one of those “Why didn’t we think of this sooner?” systems that came about in early 2020 when CIO Jason Johnson joined warehouse staff to handle a surge of orders—an unanticipated side effect of the COVID-19 lockdown.
Johnson’s warehouse shifts today aren’t necessitated by global disaster, but something he puts on his calendar once a month. “As an associate, in fact,” he clarifies. Try as he might to blend in, his presence does have a certain wheel-greasing effect; simple ideas like the red totes are a lot more likely to become standard procedure when he’s around.
Having tech leaders on the floor isn’t just about erasing the middleman, though. It also eliminates operational silos, accelerates business objectives, and boosts employee retention. Johnson’s approach—and those of other CIOs—shows why the best tech leaders refuse to choose between being tech-deep or business-focused, and how that dual fluency drives success.
Breaking down silos
Only 23% of frontline workers think senior leaders understand their day-to-day reality, according to a recent ZipRecruiter report. For most executives, that’s a culture issue. For Chief Information Officers, or CIOs, it’s an operational blind spot that directly impacts the systems they’re responsible for building.
CIOs have a unique vantage point in that they’re responsible for both the technology that powers operations and understanding the business processes that technology serves. When that information comes secondhand through tickets, reports, or user feedback, critical details get lost in translation.
The risk of that disconnect is well-documented. Varun Ragbir, a CIO in healthcare IT, warns that leaders who stop engaging with the technology they oversee “may lose credibility, make misinformed decisions, and ultimately limit the organization’s ability to adapt.” Without hands-on involvement, he argues, CIOs risk “outsourcing critical thinking to vendors or internal teams,” creating gaps in efficiency, security, and innovation.
This involvement doesn’t have to be anything complicated. “I will literally sit down with a sales engineer, plug a headset into their phone, listen to the call, and watch them use our tools,” Johnson explained in a recent interview. “A lot of times that feedback doesn’t come any other way.”
In other companies, this sort of data collection might be delegated to middle managers who later present their findings in slide decks. But when CIOs and other tech leaders actively participate in daily tasks, they spot and solve inefficiencies immediately, helping the business to execute faster.
Drills, not screwdrivers
Another way the best tech leaders break down silos is by aligning operations with the company’s strategy or mission. According to Forbes Tech Council, this ability to accelerate business objectives should be a given for not only CIOs, but their reports, too.
“I don’t say this to be pretentious,” starts Johnson. “But one of my core beliefs is that most folks who don’t think in technical terms—they have screwdrivers, right? And here comes IT with a drill.”
“When we see a user copying and pasting between two fields in an app we built, the user thinks that’s just how the app works. That’s how they were trained to use it. Meanwhile, I look at that and think, man, we could put a button there to do that for you. I can save you a step. I can make it more efficient.”
It’s this interplay of technical and operational thinking that improves not just software functionality, but entire organizational workflows. IT departments can build this practice into their culture from day one. Johnson’s new hires spend their first week rotating through different departments so they can see what daily challenges look like across the organization—an immersive experience rather than a quick tour.
But institutionalizing the practice isn’t enough—leaders must model it themselves. Johnson packs boxes on the warehouse floor for several hours at a time because, he explains, “you won’t see the same opportunities if you only do it for 20 minutes.”
Some leaders take this a step further. Thoughtworks CIO Jessie Jie Xia recently “demoted” herself to the role of coding intern for four days to understand an AI-enabled development method her team was implementing. By coding with her team, she could test whether the method would actually scale, and earn the credibility to lead the change.
Leaders who work alongside their teams build more than better systems—they build loyalty. And that loyalty shows up where it matters most: retention.
Operations first, retention follows
IT departments are usually notorious for their high turnover rates. A 2025 tech report from Europe cites an attrition rate of 21% for operations roles—an increase of 35% from 2024. Reasons range from burnout to dissatisfaction with compensation, culture, or management.
Over his five years as CIO, Johnson has maintained 97% retention while scaling from six to 250 employees. Two key factors drive that retention: one, a culture in which honest feedback is encouraged. “When someone walks into my office and tells me I messed up—I rejoice in that,” he says. “These conversations help me to learn and grow, and when you have people learning and growing together, they tend to stick around.”
Two, Johnson makes sure his team knows the “why” of their work. A 2025 Deloitte survey found 89% of Gen Zs and 92% of millennials consider a sense of purpose to be important to their job satisfaction and well-being. When employees understand their impact on the company, they feel more invested. “You have to let people know what they’re doing matters, and connect that back to the business win,” says Johnson. And that connection is a lot easier to make when leaders aren’t isolated in the C-suite.
Key takeaways
Johnson’s approach demonstrates what’s possible when CIOs prioritize operational immersion, but the principles are highly replicable:
- Start small. You don’t need to pack boxes or take on an internship; instead, start with 30 minutes shadowing another department.
- Institutionalize it. Build operational exposure into onboarding, like week-long rotations through different departments.
- Model the behavior. If you mandate it for your team but don’t do it yourself, it won’t stick.
- Act on what you see. The value comes from incorporating feedback immediately, not just observing.
Wherever your team’s work happens—on the floor of the warehouse, over a sales call, or within a help desk queue—that’s where insights live. Go find them.
