Sukhinder Singh Cassidy

In the latest episode of A Call to Lead, I sat down with Sukhinder Singh Cassidy, who has seen it all in the tech and startup worlds. Sukhinder was an early leader at Google, where she headed Asia-Pacific and Latin America operations. She went on to run startups that merged tech and fashion (Polyvore and Joyus) before taking the helm of StubHub, the online ticket exchange company owned by eBay. On the side (because Sukhinder is a master multitasker, as we all aspire to be), she founded and has continued to build theBoardlist (an online platform to help women get on corporate boards) while she serves on the board of Urban Outfitters. I could give you a dozen pieces of leadership wisdom from this conversation with Sukhinder, but I'll keep the list to five points and hope you'll listen to the entire podcast to hear the rest.

1. Sukhinder talked about what she called “operating range,” what she defines as one’s ability to stay strategic or operate at a tactical level when needed. "One thing I look for in [people I hire] is a principle I call operating range—the ability to think about something at 30,000 feet and at 300 feet. The ability to roll your sleeves up and be at 30 feet if that's what it takes to get the job done."

2. We discussed how important it is as a people leader to let go of trying to manage everything and instead, try to build a team that will help manage your energy and focus. "When you're operating through other people, you have to decide whether you're managing everything or you're happy to let people manage you."

3. It’s important to embrace being in situations where you’re uncomfortable - it’s those situations, and sometimes moments of failure when you learn the most. "Don't be intimidated by the thing you don't know. Try it. I guarantee you're going to come out of it having learned something you don't know today. And by the way, failure is quite okay."

4. Sukhinder and I both serve on the boards of large companies and we talked about the fact that the results are clear on diversity in the c suite and the boardroom - companies with more diversity (of all types) at the top drive better bottom lines and better results. "If you want to modernize the boardroom, you need to modernize who's in the boardroom - who brings perspectives that are relevant to these new challenges.

5. We discussed what a challenging operating environment it is for CEOs and executives today - the sheer number of stakeholders, variables, and risks, sometimes unforeseen, seem to grow each day. And you have to operate with your head up as a result. "If I'm just heads down and I'm not aware of all the forces going on around me, my ability to do my job is fundamentally altered because out of left field is going to come something at me, which I thought I was in control of—and lo and behold, I'm not. You have to know when to be heads up. You have to know when to be heads down.

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