3 CEOs That Keep Their Hands Dirty For Hard-earned Insights

I am not talking about startup CEOs. Those guys are supposed to get their hands dirty to scale. What I am talking about are CEOs that still keep their feet and ears on the ground to find the truth, even when their companies are already mature.


As the world was returning to normal after the historic pandemic, Dara Khosrowshahi, CEO of Uber, realized that his company had a driver supply shortage that could threaten the future of his company. Due to stay-at-home orders, drivers needed to find another way to maximize their earnings. Without drivers, the whole experience on Uber app would have deteriorated and Uber’s business would have suffered. In addition to offering financial incentives to lure back drivers, Dara signed up as a courier himself and ferried folks and delivery orders around San Francisco. The goal? To understand what else the company could do for drivers. The plan worked as the CEO uncovered the following shortcomings:

  • The old onboarding process for drivers was clunky and unfriendly.
  • Drivers were punished for not taking the trip whose destination and fare were uncertain.
  • Drivers were at times confused about where to pick up food at partner merchants.
  • The app combined two separate deliveries at one merchant, but didn’t inform the assigned courier

Naturally, no competent CEO would have let these issues go unaddressed. Dara instructed his team to introduce fixes with urgency. As a result, Uber is now friendlier to drivers, recovered faster post-pandemic and is in a much stronger position than its rival Lyft. Per WSJ:

Driver Danny Jacob dumped Lyft after Uber introduced pay and destinations disclosure in Chicago in September. He said the ability to see where he was going and the value of the ride was liberating, and Uber kept him busier because he could switch between rides and food delivery. 

Driver engagement at Lyft dropped after Uber’s summer rollout, according to people close to Lyft. The company’s product managers scrambled to match Uber’s changes, replicating many features months later. 

I recently took a ride to Omaha Airport with a Somalian driver. I asked him about two features recently introduced lately by Uber: Reserve rides and the ability to see the route and fare of a trip in advance. The driver said that while the former wasn’t as particularly helpful, the latter was the best feature that Uber has ever introduced and made his life so much better. Dara pushed his team to move up the timeline on the feature. Had he not had that frustrating experience himself as a driver, who is to say when Uber would have had that rollout.

Fun fact: Dara has completed over 100 trips himself so far.


Laxman Narasimhan officially took over the CEO role of Starbucks in March this year. He and his predecessor, Howard Schultz, spent a lot of time discussing future priorities for the iconic company. They agreed that Starbucks must be more disciplined in cost management and efficient if they are to expand the store network.

To that end, Laxman dedicated months to familiarizing himself with the operations by becoming a certified barista and working for several hours a month at different stores. His goal is to understand better the pain points of baristas and how to streamline the ship. The new CEO already identified two issues. One is that Starbucks has a variety of cups and lids; which makes the job of a barista difficult and supply chain more complex and expensive. The other is that baristas are usually overwhelmed by the rush hours in the morning.

Dick’s Sporting Goods

Ed Stack, former CEO of Dick’s Sporting Goods, is the son of Dick Stack, the founder of the company. Ed’s father used to tell him:

“If you had a visitor there, you wouldn’t keep doing what you’re doing. You’d drop it to say hello and make him feel at home.”

Source: It’s how we play the game

Ed carried that mentality throughout his career. He made a habit of walking the stores every month and talking to store managers. His goal was to listen to the managers’ concerns as well as to learn what customers saw and said.

From one of those store visits, a manager in Baltimore mentioned to Ed that kids went to his store asking about a brand called Under Armour. Ed had never heard about this brand before, but decided to place an order and run a test in a few stores. Under Armour merchandise flew off the shelves, prompting the retailer to move the apparel brand to more prominent sections. From there, the relationship blossomed as Under Armour contributed meaningfully to Dick’s bottom line. Had there not been the fateful visit, who’s to tell that Under Armour would have ended up in Dick’s stores?

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