A question I often get asked is why being able to delegate and empower Team Members is such an important leadership skill. I truly believe delegating is one of the most underrated yet most transformative skills a leader can possess. On the surface, it sounds simple, but in practice, it is one of the hardest things to do.
As your business grows, complexity grows with it. No matter how talented, capable, or hardworking you are, there are only so many hours in a day and only so many things any one person can do. Ironically, the more competent a leader is, the harder it can be to delegate. We are used to doing things ourselves and doing them well, so letting go feels risky.
But here’s the catch: trying to do it all yourself creates a bottleneck. Instead of multiplying impact, your talent becomes a limiting factor. Important work gets delayed. Decisions stack up. The organization slows down. Empowering your team changes everything. When you delegate with trust and clarity, you free yourself to focus on what truly matters: big-picture strategy, culture, and growth.
At Whole Foods, I saw firsthand how powerful this principle can be in practice. Real estate was always a pivotal part of our growth strategy, especially in the early days, and something I genuinely enjoyed. I love the strategy behind it and believe great real estate is one of the most important factors in a brick-and-mortar business’s success. When we decided to expand into California and open our Palo Alto store, I moved out there for a few weeks to immerse myself in the area, studying the traffic, the people, and the overall feel of the place. I often joke that whoever invented the word “yuppie” must have lived in Palo Alto. But as we grew, it became clear that I couldn’t stay as involved in real estate—it was no longer where the company needed me most. Delegating this responsibility to others wasn’t just necessary; it was essential for us to continue growing.
Another example that comes to mind is my friend Walter Robb. In 2004, he was promoted from Regional President to Co–Chief Operating Officer alongside A.C. Gallo, and later they both held the title of Co-Presidents. During that time, Whole Foods experienced some of its greatest successes, thanks in no small part to these leaders’ efforts. Walter and A.C. were simply the best retailers I have ever known, and together they helped lead a remarkable era of expansion for the company.
At the same time, it was clear to me that Walter was ready for even more responsibility. He had strong relationships with other business leaders, communicated exceptionally well with investors, and had an impressive network in the broader business and political worlds. I didn’t want to lose him, and I knew the best way (and perhaps the only way) to keep him at Whole Foods was to promote and pay him more — but the only position above him was mine. Eventually, we decided the best path forward was to name Walter co-CEO. By doing that, I was able to delegate responsibilities that played directly to his strengths and interests, things like quarterly earnings, investor relations, and media, while allowing both of us to focus on the areas where we could have the greatest impact.
Experiences like these reinforced something I believe deeply about leadership: great leaders do not measure success by what they can do alone, but by what their team can achieve together.
