“From the Desk of” is a new editorial series focused on the members of Round and how they lead. From startups to some of the world’s biggest tech companies, follow along to see how some of tech’s most successful technologists think about leadership within the tech industry.

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From Yahoo to Microsoft, Amazon to Stitch Fix, Sharon Chiarella has over 20 years of experience delivering rapid innovation and scalable technology to achieve high growth for some of the world's most successful technology companies. Now, as the VP of Consumer Experience, Chiarella leads the engineering, machine learning, and TPM teams responsible for delivering the Netflix famed consumer experience. We sat down with Chiarella for a conversation about how she leads.

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Describe your leadership style in three words.

Direct, Inquisitive, Tenacious Who inspired your leadership style? I’ve worked for and learned from so many great leaders. While at Amazon, I worked for Andy Jassy, CEO of Amazon, and Jeff Wilke, CEO of Amazon WW Consumer. Their leadership styles differ, but what I admire about both is their ability to think big and small simultaneously: they push for bold innovations while staying attuned to the details. Andy and Jeff also taught me how to think about scale and regularly evaluate my performance.

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What’s an inflection point that shaped how you lead?

When I was leading a team of 200 people, I became frustrated because I was no longer able to dive deeper into the technology I was working on, like I previously had when managing smaller teams. I hadn't adjusted how I was leading; I was either slowing things down by being a bottleneck for decisions or I was only superficially on top of the areas I owned.

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One of the systems I owned was in the middle of a significant migration. The team had been migrating one country stack at a time, starting with smaller, lower risk countries. They learned and optimized after each country launch. However, these migrations were not going as quickly as planned and we didn't have enough time to complete the work before our peak traffic was going to hit at the end of the year. Because I'd not been on top of the details, I didn't discover this until there was very little time (days) to recover and I hadn't inspected the team's contingency plan (they didn't have one). After the peak traffic period was over, we completed a retrospective.

The team primarily focused on the tech and migration plan issues that caused the problem. I did my own retrospective and after asking the 5 whys, I came to a few conclusions:

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1. This project was one of the key goals of the organization and rather than trying to stay on top of everything, I needed to create a mechanism to dive deeper on our key goals and our progress towards them.

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2. While the team was adjusting the technology based on new information from each country, they weren't adjusting their migration plan or timing. Similarly, they didn't have a contingency plan. These were obvious questions that should have been asked, so I developed a set of "go to" questions that allow my teams and myself to assess the plans. Example questions include things like: What's your contingency plan? What other options did you consider? Why is this the recommended course of action? I published these questions so that teams would know what questions I expected them to be asking and answering.

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3. The big lesson for me was that the team got in this situation because they were launching in low risk countries first. By doing this, they were eating into the calendar time before peak. While launching in low risk countries first seems like the lowest risk approach, it became high risk because the existing tech would not be able to support peak load in the larger countries. My takeaway from this is that sometimes doing the "low risk" thing can actually be high risk in the long run. Thinking of this issue as a risk management problem, rather than a tech problem, allowed me to level up my thinking.

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How do you empower those around you to help elevate their leadership?

I think leaders disempower their teams when they overrule their teams’ decisions or make decisions for them. Whenever I’m at odds with my team over a decision, I try to assess why we’re not aligned: Is there context I’m missing? Are our goals different? Sometimes the root cause of a conflict is easy to address; other times, the cause is a different tolerance for risk or out-of-the-box thinking. These aren’t bugs; they’re features. In such cases, I focus the discussion on the risk vs. reward of our various options.  

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I believe that great leaders build great teams that make great products. I push my leaders to think about how they’re building great teams and how they’re scaling. Many people tend to focus on short-term deliverables, but I encourage my leaders to also focus on the long term: where they imagine their team 18 months to three years from now.

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How is leading in tech different from other industries?

The tech industry changes at a much faster pace. We focus on taking risks and driving change instead of waiting for change to happen. Tech leaders have to look around corners, anticipate opportunities (or risks), and appropriately allocate resources and energy.  

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What makes you optimistic about the future of the tech industry?

Every new advance in tech helps solve existing problems and creates new ones. It also creates new, unexpected opportunities. I think that’s what I love the most about the industry. There’s always another wave to ride.