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CHAPTER ONE What It's Really Like to Be an Executive at a Startup—and How It's Different from Being a Director or Manager

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Is being a startup executive really that different from being a manager or director? Yes. But probably not in the ways you think.

Prior to becoming a startup executive, my view into the role was limited. I saw how the “executives” behaved in our one‐on‐one meetings and while presenting to our entire company during all‐hands meetings. I noticed how they emailed, messaged, and comported themselves at the office. I observed how they spoke in our companies' all‐hands and how they behaved at holiday parties. I watched them, as most startup employees do their leaders. (If you're reading this, know that people are paying attention to your behavior.) But my view wasn't close to the full picture of what their roles demanded.

At various companies I'd worked for, many of the executives' calendars were fully booked in meetings so often I wondered how they got any work done. What were they doing during these blocks? Beyond their busyness, I wondered what that translated to in terms of what their jobs required on a day‐to‐day, weekly, or quarterly basis.

Now that I'm an executive, I understand that the bulk of work done by an executives team is challenging to grasp as an individual contributor or even mid‐level manager. While there's been a movement to increase transparency across the startup ecosystem and more companies openly share their operating principles and salaries to their employees and even to the public, much of the inner workings of a startup leadership team are hard to see if you're not a part of it. This chapter covers what a startup executive role involves behind the scenes, including insights from executives on what their work‐life entails on a daily, weekly, and monthly basis.

“The more senior you are, you execute less, and you have to be efficient with your time and need to empower your team to achieve your goals,” says marketing executive Rachel Beisel. “You're in a lot of meetings because you're often the facilitator between departments and between employees in those departments.”

The reason that executives spend so much time in meetings is that decision‐making is their most important responsibility. While startup leaders will always execute to some degree at earlier‐stage companies (including the founders and CEO), their ability to strategize and decide is why they exist at the company.

“As a founder, I have decision fatigue,” said AQUAOSO CEO and co‐founder Chris Peacock. “I expect my executives to constantly make good decisions in their areas, even in the absence of all of the data.”

Executives are charged with managing managers, meaning their direct reports generally have their own reports. This “skip level” hierarchy requires executives to empower their reports to make good decisions and own their areas.

The level of hands‐on work you do as an executive will vary based on your startup's stage and maturity. Early on in a startup, you'll be spending more time on execution, doing things like shipping a new landing page, or editing copy, or creating financial models. These deliverables are a big part of how your success is measured early on. But as your company grows, you'll need to delegate and manage other people who can do those things while you manage their productivity.

Lead Upwards

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