What Amazon Customer Service Taught Me About Leadership

Hello,

On my first opening day as superintendent in the district where I work, we did the standard opening day fare. We celebrated service anniversaries. We welcomed new hires. We talked about the year ahead. Those rituals are important, and they deserve time and attention.

I also wanted people to know a little bit about me, not just my role, but how I think. At one point, I said, “I’m going to hell.” Everyone laughed, which was the goal. I explained the reason I am going there is that I shop on Amazon way too much. It is incredibly easy. Everything is right there.

But what really keeps me coming back is not convenience or selection. It is their customer service. I talked about how easy it is to return things, how little friction there is when something does not work out, and how rarely I feel blamed for needing help.

Then I told them this: when they come to me, I want it to feel like Amazon customer service. I cannot always give people what they want. I cannot fix everything. But I do believe that adults do not ask for help easily, and when they do, I have a responsibility to listen.

People appreciated the message. You could feel that in the room. But appreciation and trust are not the same thing. Words land differently than actions, and people understandably wait to see whether what is said will actually hold up. That pause makes sense because trust is built on experience.

Amazon understands something fundamental about human behavior. People do not mind being told no nearly as much as they mind being made to feel small for asking. Amazon makes it easy to return things, even when the situation is not perfect. I have been helped outside the return windows. I have received replacements without being asked to send the original item back. More importantly, they remove the emotional cost of needing support. That feeling, more than any policy, is why I keep shopping there.

Leadership in Theory

The same dynamic shows up in leadership, whether we acknowledge it or not. Adults hesitate to ask for help for many of the same reasons children do. They fear judgment. They fear consequences. Hierarchy only amplifies that fear.

I was reminded of this recently when I saw a post on social media about a child at different ages confessing things to their parent.

At age three, the child breaks a mug and tells their dad. His first words are, “I’m so glad you told me,” and he helps clean up the pieces. At age five, the child pees their pants at a friend’s house and tells their dad. He wraps his sweater around them, helps them clean up, and reduces the embarrassment. Years later, the child is leaving for university, overwhelmed and homesick, and calls their dad, knowing exactly what he will say. The situations change, but the response does not.

The story is not about what happened. It is about what the child learned over time. Each response reinforced the same message: it is safe to tell the truth here. That is leadership in theory. Creating conditions where people feel safe enough to speak, especially when something is uncomfortable, unfinished, or not going as planned.

Leadership in Action

Theory, however, is easy to agree with in the abstract. What matters is what happens when someone takes you at your word. A couple of months after that opening day, I learned how closely people were watching.

After working with a small team, I shared a change that was going to take place. Not long after, a teacher approached me and expressed concerns about the decision. In that moment, the specifics of the change mattered far less than the response it would receive. How I reacted would either validate what I said on opening day or quietly undo it.

I thanked her profusely. I told her that I am many things, but a mind reader is not one of them. I would never have known how she felt unless she told me. I thanked her for trusting me enough to speak up and told her she had given me a lot to think about.

Then I did the part that turns listening into action. I shared her feedback with the team, asked us to pause implementation, and requested that we revisit the original decision in light of what we had heard. That did not guarantee a different outcome. It did guarantee that her voice mattered.

Leadership as Service

This is where leadership stops being about position and starts being about service. Amazon did not earn my loyalty by being perfect. They earned it by consistently responding in ways that make it easy to ask for help without fear or shame. They understand that how they respond matters more than whether the answer is yes.

Leadership works the same way. It is not about meeting the needs of the leader. It is about being in service to others, especially when the answer is complicated or disappointing. I cannot always say yes. I cannot always change the outcome. What I can always do is respond with respect, curiosity, and care.

That is why I continue to shop on Amazon, even knowing I probably should not scroll quite so much. More importantly, it is why I believe leadership lives or dies not in decisions, but in responses.

~Heather

P.S. This week’s Catch of the Week is honoring African American history. Not as a single month or moment, but as a core part of our shared story. African American history is American history, shaped by brilliance, resilience, creativity, and leadership in the face of exclusion and injustice.

Honoring this history means telling the full story. It asks us to acknowledge both the harm and the contributions, the barriers and the breakthroughs. It requires moving beyond surface level recognition and toward honest engagement with whose stories are centered and whose voices are heard.

For educators, leaders, and communities, this work is ongoing. It shows up in what we teach, what we value, and how we create spaces that reflect truth and belonging. When we engage African American history with intention, we do more than look back. We build understanding, responsibility, and a more inclusive future for everyone.

P.P.S. Please remember to...

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