DoorDash has had a program since its early days called “WeDash” that requires every corporate employee (even the CEO!) to complete a set number of deliveries each year. This is a simple idea with huge impact! It keeps corporate employees connected to the work that’s actually driving the business. The program gives employees firsthand insight into customer expectations, merchant pain points, and the pressures gig workers face on the road. It also keeps leaders grounded in reality, not assumptions. 

For HR and leadership teams, this is a masterclass in designing a culture where decisions are informed by first-hand experience instead of distance from the day-to-day operations. 

Why programs like WeDash work 

They create shared understanding. When employees get out of the boardroom and into the environment where the service actually happens, they see challenges that rarely appear in spreadsheets. This gives teams better judgment and strengthens communication between departments. 

They increase empathy. Experiencing the frustrations and pressures that customers and workers face builds compassion. That makes leaders more thoughtful about policies, timelines, and expectations. 

They support better decision making. When people are close to the work, they notice the small but meaningful issues that often get lost at higher levels. These observations lead to stronger strategies, smarter process improvements, and products that solve real problems. 

They reinforce accountability. It is much harder to create hard-to-use tools, rigid processes, or unrealistic targets when you have personally felt the impact of those decisions in practice. 

The HR connection 

This approach is exactly what strong people leaders do. It mirrors HR practices like skip-level meetings and job shadowing to understand the daily experience of staff. It also aligns with principles of people-centered design: involve the users, hear from them directly, and regularly test assumptions in the real environment. 

For HR specifically, programs like this help build: 

• A culture of humility, where no one is too senior to understand the work
  • Psychological safety, because leaders show they value real employee experiences
  • Trust, since staff see leaders making an effort to understand their world
  • Engagement, because people feel their perspectives matter 

A takeaway for any organization 

You do not need food delivery drivers to create this level of connection. Any company can encourage leaders to spend time in core operations. This could include shadowing customer service reps, observing field teams, or rotating through different departments. 

When people leaders and executives stay close to the heartbeat of the business, the entire organization benefits. Decisions become wiser, culture strengthens, and the workforce feels seen and understood. DoorDash’s model is a clear reminder that leadership is most effective when it is grounded in real experience and human insight. 

 

Michelle MacFadgen, CPHR, is the Director of Client Engagement at uptreeHR, an outsourced Human Resource department for small to medium-sized businesses. Michelle and the team are based in Halifax, Nova Scotia.

To book a complimentary 30-minute consult with Michelle, click here.