Put simply, a chance to talk with someone in this position is incredibly valuable and they may play a variety of different roles during the hiring process. In smaller-stage companies or roles in their direct reporting lines, they may be evaluating you based on functional, industry or technical expertise, leadership potential, or a wide set of competencies and capabilities they believe are key to success in the particular role, and also within the overall organization. It’s possible that they are close to the operations of a given team, project, or position, but don’t expect them to spend time getting into the weeds and don’t take them there with your questions (but do ask questions!).
If you’re interviewing at a large company or in an entry to mid-level role, you may not interview with the CEO. However, if you’re pursuing a role at a small company or startup, there’s a decent chance you’ll be able to cross paths during the hiring process with the CEO, a member of the founding team, or another C-level executive. Regardless of the company size, C-level leaders and founding teams have to operate at the 50,000-foot view, bringing together diverse topics, priorities, people, and processes into a cohesive, structured, and viable path forward. In some ways, these senior leaders are accountable to “no one” (they don’t have a boss), but they are also accountable to everyone (the full team, investors or board members, customers, shareholders and beyond).
In an ideal world, there is alignment from the leadership team all the way throughout and across the organization. In reality, that’s tough, so focus less attention on the specifics of the position and listen to their insight on themes, long-term priorities, and aspirations for the team and company to get an impression of how their leadership flows throughout the organization. In anticipation of this conversation, refine your elevator pitch and do extra research on the company and the leader’s background (by reading blog posts or articles, listening to podcasts, following them on social media, and watching interviews). During interviews, be prepared to speak not only to your own background and experience but a set of connected and expanded topics as well. This is a rare chance to demonstrate your presence, articulate your talents, and leave a lasting impression.