411: Caring, Campaigns & Communication: The Dovetail Solutions Story

On this episode of the Leadership with Heart podcast, I’m joined by someone very special to me, Andy Boian, founder of Dovetail Solutions and a longtime friend and collaborator. Andy first joined me on the show back in 2020 and was also featured in my book The Art of Caring Leadership. Since then, a great deal has changed, both for him and his company, and I was thrilled to bring him back to discuss where he stands now as a leader and how his journey has unfolded.

We discussed what it means to grow an organization with intention, to lead by listening, and to cultivate a culture where people feel safe enough to share their truth. Andy shared how he continues to live by the philosophy of speaking last, something he mentioned in our first interview that has stuck with me ever since. It’s not just a tactic; it’s a way of honoring the voices around him and building trust from the inside out.

Andy also opened up about how his company has evolved over the past five years, how they’ve weathered disruption and grown their reach, and how he’s now thinking about legacy. He shared that he’s entering a season of succession planning, gradually preparing to pass the torch while continuing to serve as a mentor and advisor. His desire to give back, to teach, and to write about what he’s learned was inspiring to hear.

We also discussed the role of AI in communication and storytelling as well as the importance of maintaining the human element in our work. As a speechwriter, Andy knows that words matter, but so do context, presence, tone, and lived experience. AI can assist, but it cannot replace the empathy or emotional insight that comes from years of connection.

What stood out most in our conversation was Andy’s consistency. He still believes in telling the truth, even when it’s hard. He still creates space for people to think, feel, and lead themselves toward their solutions. And he still leads with care, humility, and a deep understanding that trust is earned every single day.

If you’ve ever struggled with how to hold space as a leader, how to grow through grief, or how to lead a team without controlling every detail, this conversation will offer real encouragement. Andy reminds us that leadership is not about being the loudest voice in the room. It’s about knowing when to step back, when to listen, and when to let others rise.