Having regular conversations with your manager is important to ensure that you are on track for your desired career growth. But just as important is to occasionally have similar conversations with your skip level leaders.
When it comes to skip level one-on-ones, there are three key outcomes to look for. First, is to build a relationship with your leaders. Second is to have an opportunity to highlight your contributions to the organization. And third is to have more insight into the direction that your leader is driving the team. Even just requesting the one-on-one will help you stand out when it comes time for promotions because most people never request a skip level meeting. This one act shows your leader that you are proactive and interested in advancing your career.
Building a relationship. Unless you work for a very small company, your leaders are responsible for a lot of people; potentially a couple of hundred in larger companies. It is very rare for your skip level manager to know much about you individually. Requesting a one-on-one with them allows you to get to know them on a more personal level and for them to get to know you better. People are more likely to help people they like, so establishing a positive relationship and not just engaging in small talk should improve your chances of better assignments and eventually career advancement.
Showcasing your contributions. When the conversation eventually turns towards your work, this is your chance to practice your presentation skills. Episode 056 covered Presenting to Leaders (https://www.managingacareer.com/56); revisiting that episode should help you here. If you think about the scope and timelines that you are responsible for compared to those of your skip level leaders, their focus is on larger efforts and longer time horizons. So, as you describe your recent accomplishments, make sure you focus on describing them in relationship to the bigger picture. Many of the insights from Episode 44 - Reporting Status (https://www.managingacareer.com/44) apply when communicating verbally, too. Focusing your contributions in terms of value produced will ensure that your skip level leader can relate what you do to the things that they care about.
One of the benefits of presenting your contributions in the context of value to the organization is that it signals to your leader that you are starting to think strategically. Back in Episode 49 (https://www.managingacareer.com/49), I cover several ways that you can transition to more strategic work and having your skip level leader recognize that growth should help.
Gain Insight. The third goal of a skip level one-on-one is to learn about the direction of the organization from your leader. The purpose of this isn't to feed the rumor mill. Use this time to understand the drivers for the decisions that they make and figure out how those drivers can also be applied to your priorities. How can you leverage these insights to devise an idea that involves a bigger scope than your current level of responsibilities? Don't try to...
