Getting Value from Skip-Level Conversations

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In 2015, I joined Pinterest as a software engineer after my company was acquired. Going from a five-person company to a 500-person company was daunting, especially since I had never worked in a hypergrowth organization. I talked previously about best practices for onboarding, but I want to specifically focus on an area that I sorely neglected: the skip-level one-on-one meeting.

Your skip" is the person your manager reports to, often a director or vice president. It's what happens when you skip" your manager up the reporting chain. Many of the ideas from a previous newsletter, Making the Most of 1:1 Meetings With Your Boss, carry over here, but skip-level 1:1 should be treated differently. The skip meeting can feel either nerve-wracking or irrelevant for many engineers, but it's actually a unique opportunity to accelerate your career.

Here's how you can get the most value from your skip-level meetings:

• Understand your organization's overall strategy. Your skip manager has a broader scope and set of responsibilities compared to most people you interact with. This means they are naturally equipped to answer questions around organizational strategy. Ask them what their priorities are, and how your work contributes to the priorities they care about.
• Share on the ground" insights. No matter how hands-on they are, senior leaders are often disconnected from day-to-day work. As an individual contributor, you are well-equipped to share the experience of getting work done, both the good and the bad. This can be especially valuable if you can proactively suggest ideas to improve everyone's productivity.
• Be honest with feedback. A truly effective skip-level meeting requires you to be unafraid to share real problems and provide honest feedback. This is an opportunity to discuss systemic issues that your direct manager may not be able to address on their own.

At Pinterest, one of the first decisions I had to make was about which team within the company I would join. Had I properly leveraged the advice from the director, I could have received valuable feedback about high-priority areas in the company. Whether you're new at a company or not, don't squander the value of building a relationship with your management chain.

-Rahul

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