The right question can help a founder challenge assumptions, uncover blind spots, and look at a problem from a different perspective.
A well-timed question can expose something the founder hasn’t considered.. Questions like “Will someone actually pay for this?” force founders to separate enthusiasm from evidence.
Asking questions is encouraged at a Bootstrappers Breakfast meeting. Terry’s goal isn’t to have all the answers. It’s for founders to leave the table thinking differently about their businesses than when they arrived.
Terry, thank you for everything you bring to Bootstrappers Breakfast and, especially, for the thoughtful questions you ask founders around the table.
What makes your approach so valuable is that you create an environment where founders can think out loud, examine their assumptions, learn from one another, and arrive at their own conclusions. You know when to ask another question, when to challenge an idea, and when to give someone the space to work through a problem.
That spirit is at the heart of Bootstrappers Breakfast. The meetings aren’t lectures where an expert tells entrepreneurs what to do. They are conversations where founders share experiences, ask questions, compare approaches, and help one another make better decisions.
About Terry Holmes
Terry Holmes is a workplace relationship consultant and founder of The Good Org, LLC, where he helps organizations strengthen communication, relationships, and their ability to navigate change. Drawing on more than 15 years of experience in marketing technology, Terry brings a practical understanding of the challenges facing fast-moving organizations.
His expertise includes leadership development, group dynamics, change management, and organizational behavior. He has worked with organizations including Apple, eBay, Kaiser Permanente, the City of Berkeley, and the State of California. Terry serves as an adjunct professor of Organization Development in the MS in I/O Psychology program at SJSU. He is also a lecturer and Interpersonal Dynamics Facilitator at Stanford Graduate School of Business.