Dr. Andrea Hollingsworth
I’ve learned over the years that care doesn’t always look soft. Sometimes its truest expression is the hard conversation you’ve been putting off, the decision that’s right even though it will disappoint people, or the change you have to lead before anyone, including you, feels ready for it.
I’m Dr. Andrea Hollingsworth, and I coach executives and senior leaders who want to do those hard things well, with a clear head and an open heart, holding high standards for performance while staying genuinely connected to the people they lead. As a researcher, author, and trained psychotherapist, I work with you on both what you’re facing at work and what’s happening underneath it, so that you can stand steady, clear, and connected even in seasons of intense pressure and change.
From the outside it looked like a very successful career, and in many ways it was, but what nobody saw was that much of that success was being driven by a relentless inner voice telling me I was a fraud, that I would never be good enough, and that I should either give up or grind harder. I burned out and walked away from my dream job at Boston University at the age of 36.
That experience changed the course of my life, and today I bring together my research, my clinical training, and years of working alongside leaders to help you lead and succeed from a steadier and kinder place than the one I was driving from back then.
I call my work therapeutic leadership coaching, because the challenges leaders bring to me are rarely only professional. The personal, the relational, and the professional are woven together, and pulling them apart usually means leaving out the part that matters most. So yes, we’ll set goals and find practical solutions, which is the heart of coaching, and we’ll also make room for the reflection and healing that help those changes really last.
Together we might work on softening the inner critic that keeps you replaying a meeting long after it’s over, setting boundaries without the guilt, staying grounded through change you can’t control, or finally having the conversation you’ve been putting off. Sometimes we begin with an exercise I call Future Me, where I invite you to picture yourself at ninety on a park bench, looking back on a life well lived, and to notice which values that future you embodies, because those values have a way of showing you what matters when today feels overwhelming.
I once worked with a CFO whose company was going through a long, slow acquisition. On video calls he looked composed, but underneath he was struggling mightily with self-doubt and an inner critic telling him he didn’t have what it took to lead his people through uncertainty, loss, and big change.
Alongside his leadership goals, we explored where that voice came from and found practical ways to soothe it, to let go of what he couldn’t control, and to trust himself again. He found the grounding he needed to lead well through a year and a half that was hard on everyone.
I use AI tools in my own work every day, and I’ve come to believe that as technology takes on more of what we do, the human things a leader offers are becoming more valuable, not less. People can tell the difference between real care and a simulation of it, and they do their best work where they feel seen, safe, and supported. That kind of leadership begins with how you treat yourself.
You can tell me what’s going on and what you’d love to be different, and together we’ll figure out whether working together feels right. There’s no pressure and no pitch, just an honest conversation between two people.
Coaching partnerships run for six or three months, and I also offer single 90-minute sessions for when you need a thoughtful outside perspective on something happening right now. We’ll talk through what fits on our call.
You’ve probably heard the phrase, “wounded people wound people.” That’s true. But it’s also the case that “transformed people transform people.” If something here speaks to you, I’d be honored to walk alongside you.
Through practical exercises and real-world strategies, you’ll develop the skills to lead with compassion while staying agile in an ever-evolving landscape.