How Asking Questions Builds True Communication Confidence

What if the secret to real confidence in communication isn’t about having all the right answers, but about asking better questions? Welcome back to Speaking with Confidence! I’m Tim Newman, your host and a recovering college professor turned communication coach. In this episode, we dig deep into the misconception that confidence means certainty and flip the script to show how the best communicators are defined not by what they know, but by how curious they are. Joining me today is Michael Ashford, a dynamic communication and leadership coach, longtime marketing executive, and two-time TEDx speaker. Michael Ashford is passionate about empowering people to communicate in ways that traditional education rarely touches, helping us inspire change, drive action, and resolve conflict more effectively in our lives. Together, we explore Michael Ashford’s journey from nearly failing out of college as an engineering major to finding his true path in journalism, a shift that taught him the importance of aligning passion, curiosity, and personal fulfillment. He shares how letting go of other people’s expectations and finding his own voice became foundational to his confidence and success. Here’s what we cover in this episode: The false belief that confidence requires always being right and what true confidence really looks like Michael Ashford's honest story of personal and academic failure, and how curiosity led him to a career aligned with his values The pivotal role of communication skills in every aspect of life and leadership Why the education system fails us by prioritizing certainty over curiosity and the ability to ask better questions How to break out of the sunk cost fallacy in careers, relationships, and heated debates The impact of information overload and social media on our ability to trust, listen, and connect The practical power of curiosity how asking more questions shifts conversations, builds trust, fosters empathy, and increases genuine confidence Tips for anyone wanting to be a better communicator today: ask more questions, get curious about your own motivations, and embrace the “power of the pause” before responding How true introspection and questioning our own beliefs lays the foundation for alignment, fulfillment, and lasting confidence This episode is packed with real talk, actionable strategies, and stories you can relate to whether you want to communicate better at work, defuse conflicts at home, or just find your own unique voice. Dive in, and discover how you can become the curious, confident communicator you’re meant to be. Timestamps: 00:00 Starting a Podcast and TEDx Talk 04:47 Questioning career path choices 08:59 Overcoming fear of speaking up 13:07 Fixing communication in education 16:53 Unpredictability at individual level 17:47 Teaching kids conflict communication 20:51 Impact of global concerns on relationships 24:58 Interviewing diverse perspectives on policing 27:19 Documentary on Climate Conversations in Oregon 33:18 Gen Z anxiety and resilience 34:31 Dealing with anxiousness in debate 39:52 Forming early political beliefs 41:30 Questioning Beliefs and Personal Alignment 46:06 Focusing on long-term health goals 48:28 Reflecting on personal authenticity 52:06 Effective communication strategies