Unlock Career Growth With Skip Level Meeting Tips

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In 2015, I joined Pinterest as a software engineer after the acquisition of my business. Going from a company of five people to a 500 -people company was intimidating, especially since I had never worked in a hypergrowth organization. I have already talked about best practices for integration, but I want to focus specifically on an area that I cruelly neglected: the head-to-head meeting at the skip level.

Your “jump” is the person to which your manager reports, often a director or vice-president. This is what happens when you “jump” your manager in the report chain. Many ideas from a previous newsletter, by drawing the best party of meetings 1: 1 with your boss, transport here, but Skip-Level 1: 1 should be treated differently. The skip meeting may feel scary or not relevant for many engineers, but it is in fact a unique opportunity to speed up your career.

Here’s how to get the most value of your skip levels:

• Understand the overall strategy of your organization. Your skip manager has a wider scope and set of responsibilities compared to most of the people you interact with. This means that they are naturally equipped to answer questions concerning the organizational strategy. Ask them what their priorities are and how your work contributes to the priorities that are close to their hearts.
• Share the ideas “in the field”. No matter how practical they are, senior leaders are often disconnected from daily work. As an individual contributor, you are well equipped to share the experience of doing work, both good and evil. This can be particularly precious if you can proactively suggest ideas to improve everyone’s productivity.
• Be honest with the comments. A really effective leap level meeting forces you to be afraid to share real problems and provide honest comments. This is an opportunity to discuss systemic problems that your direct manager may not be able to address themselves.

In Pinterest, one of the first decisions I had to make was what team in the company I would join. If I had exploited the director’s advice correctly, I could have received precious comments on areas of high priority in the company. Whether you are new in a company or not, do not waste the value of establishing a relationship with your management chain.

—Rahul

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