CEO, Founder, or Other C-Level Exec

You’re reading an excerpt of Ask Me This Instead: Flip the Interview to Land Your Dream Job, a book by Kendra Haberkorn. This powerful work is written by a veteran recruiter for job-seekers who want to find their dream job—not just the next job. Purchase the book to support the author and the ad-free Holloway reading experience. You get instant digital access, worksheets and a question database, commentary and future updates, and a high-quality PDF download.

CEO, Founder, or Other C-Level Exec

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.

Peer or Team Member

There is a good chance you’ll get to meet someone during the process who would be a peer on the specific team you’d join. This conversation can be a powerful glimpse into an important business relationship, and the information you’ll gather from the interview as well as the questions that a peer might ask will illuminate critical elements of the role. Put simply, prospective peers are often closest to the details of the work to be done, understand the status, challenges and opportunities, and what it takes to be successful relative to the goals the team is responsible for achieving. They might also have a similar background or set of skills and capabilities and therefore ask very targeted or specific questions to evaluate your expertise and determine if you have the qualifications to meet the expectations of the role and work well with the team.

During the interview, they may play the role of a companion or partner that would be a trusted collaborator on projects and someone who will bring internal insight and context to support your integration and success. It’s also possible that they will take a more competitive approach and step into the interviewer role as someone who is not necessarily a judge (they are not the hiring manager), but also not a friend. They may challenge you subtly or directly to test the boundaries of this potential relationship while weighing the trade-offs of how you might make their life better or potentially worse.

In an ideal world, people in these roles want nothing more than a super talented, smart, capable team member to work at their side, but others will be threatened if they believe you will outshine them, “take away” something they enjoy doing, or upset a status quo that works for them.

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