Choosing the right executive coach is key to a successful engagement. You are looking for chemistry because it is a relationship like any other. Hopefully, you have some “aha” moments, even in the first conversation, to give you a flavor of what is possible and what that could feel like going forward. You should ask some questions about the frequency and cadence of the coaching conversations, what topics you might want to discuss, and what success would look like for you at the end of the engagement.
I typically recommend to anyone looking for coaching that they talk with several people and have “chemistry conversations” with at least two. You will get a feel for the coach’s style in those conversations. Understand their questioning approach and determine if it is right for you. Is the coach a bit more direct? Can the coach be a little bit softer in their approach? Sometimes people’s preferred way of being held accountable has a different flavor. You will want to look for a coach that can support your preferences, whether gentle or more direct. Often an executive coach who gives you feedback more concretely can allow you to move forward quickly. However, at the end of the day, it has to be a relationship of trust that supports you in a way you can digest, internalize, and ultimately creates the path to your development. The critical piece is finding somebody you connect with and who can help you move your leadership game forward and upward.