Workplace Jiujitsu #17: How To Approach Skip-Level Meetings As An IC

As an IC, you are generally busy with technical implementation. But taking the time to speak with your boss’ boss through a “skip-level meeting” is a high risk, high reward strategy for growing your network and accelerating your career. 

The best time to do it is when you or they are new. It can serve as an introduction. By building rapport, in the best of cases, you can gain a mentor, a sponsor, advice, or insights. On the flip side, skip-level meetings can also be professionally damaging by hurting your relationship with your manager.

To minimize the downsides, be transparent about it with your manager before the meeting. It’s not pleasant to be sidestepped and blindsided. During the meeting, make sure to give the impression that you are energized, motivated, and happy to be at the company. Remember that anything that you say in the meeting will likely come back to your manager, so prefer to not air grievances and criticisms. 

From their side, they get the benefit of having another connection with an employee that can give them insights into team dynamics and an employee’s perspective on the company. But make sure to not waste their time. A cadence of 6 months is a good one to respect their time and maintain the relationship. Come prepared with a list of questions or topics. 

Upcoming projects, department-wide technical vision, industry trends, perspective on leadership, company strategy, and career advice are fair topics to discuss.

If the meeting goes well, great. You expanded your network and did not burn the relationship with your manager. If the meeting does not go well, you have learned more about the company culture and know to not schedule another one.

From my personal experience, a skip-level meeting I had gave me valuable insights into the origins of the company I worked for. I learned about the evolution of the engineering culture and the role of team size in shaping organizations.

Cheers.