What 3 CEOs Learned After Spending a Day in Their Employees’ Shoes

UPDATED: May 23, 2023
PUBLISHED: May 22, 2023
barista making coffee drink

You might remember watching episodes of Undercover Boss, the television show that had leaders and CEOs doing everything from trudging around in sewers and serving food alongside their employees. Recently, some CEOs and other C-suite leaders have been reviving the philosophy from that reality show, jumping on this trend of getting in the so-called trenches with employees to better understand their own companies.

Uber CEO Dara Khosrowshahi spent not just a day but several months working as an Uber driver in San Francisco. The Wall Street Journal reported in early April how he jumped behind the wheel of a modest secondhand gray Tesla using the name “Dave K.,” only to report back that he agreed with drivers’ complaints—“The whole experience was pretty clunky,” he said in the article. Since that experience, he’s using his new knowledge of how things really work on the literal street level to create a company-wide “transformation,” including a better tipping policy and improved communication processes.

In March, Starbucks’ new CEO Laxman Narasimhan pledged to do the same, which he announced in a letter to employees upon starting his new role: “To keep us close to the culture and our customers, as well as to our challenges and opportunities, I intend to continue working in stores for a half day each month, and I expect each member of the leadership team to also ensure our support centers stay connected and engaged in the realities of our stores for discussion and improvement,” he wrote, noting that he plans to earn his green apron every day.

Here’s what other CEOs and leaders say there is to be learned from walking a day in employees’ shoes.

If you are ready to listen, you’ll see the inefficiencies and opportunities.

Sarah Luna, the president of Xponential Fitness, “the largest global franchise group of boutique fitness brands across a variety of verticals,” according to their website, oversees around 250 employees. The former president of Pure Barre, she decided to spend some time in the daily lives of employees’ shoes before stepping into her leadership role after her current company’s acquisition of the brand. 

“I felt it was important to understand the challenges that studios, franchisees and employees were facing on a day-to-day basis,” she explains, noting that Pure Barre was in the midst of determining the best sales model and trying out new membership options. “As a franchisor, it’s my top priority to provide the best support possible to franchisees, so I need to know what kind of obstacles, distractions and inefficiencies are happening at the studio level so we can find solutions and come out stronger.”

She saw “face to face” how those new implementations were impacting employees and clients, starting with a 5 a.m. wake-up to be able to check members into a 6 a.m. class. “I was handling the challenges that our employees face daily, whether that was changing toilet paper rolls in the bathroom or finding a substitute teacher or selling a membership,” she says.

It was this distinct reminder of how hard employees work every day, and how “well-orchestrated and choreographed” the experience has to be, that helped her determine that economy of operations should be top of mind in any decisions the company makes. “I think there’s a misconception that running a fitness studio is easy and success just happens. That is not the case at all,” she says.

The changes from her time in the studios were tangible and specific, “Down to the type of cubbies we were installing in studios to how the brand’s app functioned for members,” Luna notes. She also learned about the degree of fatigue franchise owners were experiencing, through her conversations with leaders at that location, after multiple leadership changes. “So whatever changes we had planned for the brand needed to be thoughtful and proved out. We have to make sure to deliver on anything we roll out across the system,” she says.

She has some tips for other CEOs wanting to give this a try:

  • Do less talking and more listening so you can pick up on “subtle cues” around the inefficiencies and opportunities. 
  • Be in uniform to blend in with the other staff, rather than looking like the president of the company, so people feel comfortable sharing complaints, ideas and feedback.
  • Be open to feedback, even if it’s tough to hear.

You might find out just how much your work matters to clients.

“Christopher Rim, the [28]-year-old founder and CEO of Command Education, has mastered the art of Ivy League admissions so you can, too,” according to the New York Post. Rim runs a consulting service for families who have kids hoping to get an acceptance letter to a top school, and though he has always been “deeply involved” with his lead mentors, he recently became a full-time mentor for the day. His goal? “To get back to my roots and reconnect with the passion that led me to found Command Education.”

So, he joined five calls and completed in-depth research to prepare for and follow up on those sessions, which involved mentoring prospective college students from around the world. “The content of those calls varied greatly by client: The first student in Saudi Arabia is working to launch a small business, so we brainstormed a marketing campaign to recruit initial clients,” he says. “My next call was with a parent of a rising senior, who had a series of questions about best practices for applying to prestigious colleges in 2023. The last three calls of the day were with that mother’s student, and then with two U.S.-based sophomores—one is in the midst of scaling her passion projects and the other is negotiating the terms of her upcoming summer internship.”

What Rim saw is a symptom of the college application landscape—dramatically more competitive admissions processes and the stress that puts on families. “My day in the life of a mentor was a much-needed reminder of how important our work is, not only for students’ academic success, but also for their personal flourishing,” he says. He also learned about how his employees would prefer a bit more structured time for team collaboration and analysis, rather than impromptu or unofficial conversations. “They expressed that scheduling more structured time for team analysis would allow them to more frequently enlist the expertise of their fellow mentors when coming up with creative solutions for their students,” he continues.

He has some advice for other CEOs that he learned through this experiment:

  • Implement intentional strategy sessions for their entire team.
  • Rely on team members’ voices to determine the most productive way to incorporate these sessions.
  • Try any of the following: “An open dialogue, a meeting with a prewritten agenda or a session with explicit expectations and outcomes… collaborative working will enrich the culture of your organization and lead to increased productivity,” Rim suggests.

Your team will feel seen, heard and validated.

Sure, you might be in this experiment for process improvements. But a potential positive side effect is the immense validation your team may feel as you experience what they do on a daily basis, from pain points to wins. That’s what Chintan Shah, president and managing partner of KNB Communications, a boutique marketing and PR firm that specializes in healthcare, health tech and life sciences, experienced.

He decided to completely oversee two client accounts, from onboarding through final summary meeting detailing with deliverables and impact, with the mission of learning more about what their new customer engagement process looked and felt like up close. “I found it helpful to learn how this process resonated with our customers, the type of information they were willing to share (and not share) with us and what questions we should ask our customers early on in the relationship,” he says. He learned what account directors, who typically oversee this process, might need in terms of support going forward, too.

He found out how “emotionally attached” you become to clients. “An account director really feels the client wins and setbacks—a connection that likely wouldn’t transcend to me in my regular role as president,” he explains. He met with his team after his experiment. “The validation and acknowledgement of the program that we had designed felt great for everyone involved! Individuals felt heard and appreciated,” he continues.

Here’s what he recommends for other leaders considering trying this out:

  • Be humble about what you learn—go into the review with the mindset that no job is beneath you. 
  • Invest in the process, and understand it can take multiple sit-ins and customer experiences. You should commit to doing this more than once. 
  • Recognize that there is not a one-size-fits-all approach to success. It’s OK to gain multiple perspectives. 

Photo by PeopleImages.com – Yuri A/Shutterstock