Leadership Lessons in Healthcare and Law with Holly Buckley of McGuireWoods LLP 10-28-25

Summary

---

Podcast Summary: Becker Business

Episode: Leadership Lessons in Healthcare and Law with Holly Buckley of McGuireWoods LLP
Date: October 28, 2025
Host: Scott Becker
Guest: Holly Buckley, Chair of Healthcare Department at McGuireWoods LLP

---

Overview

In this enlightening episode, Scott Becker sits down with Holly Buckley to explore leadership lessons in the intersecting worlds of healthcare, law, and private equity. Buckley, known for her candid and evolving leadership style, shares practical experiences and philosophies on vision, execution, handling setbacks, nurturing new leaders, and maintaining team morale through turbulent times.

---

Key Discussion Points & Insights

Balancing Vision, Strategy, and Execution

• Closed Loop System: Buckley explains her approach to connecting vision, strategy, and execution by treating them as a "closed loop system" instead of separate or competing priorities.
  • "The high level vision is what each executable needs to be measured against… it's really helpful when you're looking at executable tasks… to say: is this consistent with the strategic plan?" — Holly Buckley [00:41]
• Strategic Alignment: She stresses the importance of using a strategic plan—both at the firm-wide and departmental level—as a compass for every significant decision.
  • "Where it's not [consistent], it becomes much easier to set it aside or terminate it… So I think it's just important that you're continually coming back to the vision and saying: is this consistent?" — Holly Buckley [01:18]

Overcoming Leadership Setbacks

• Direct Communication & Self-Awareness: Buckley recounts her initial struggle with being perceived as intimidating, leading her to avoid direct communication with junior staff out of concern for coming off too strong.
  • "I would often try and send the message through somebody else… but I realized over time that my message was getting lost and it wasn't being delivered how I would deliver it." — Holly Buckley [02:54]
• Learning to Be Authentic: She learned that authentic, direct communication, even at the risk of being seen as blunt, was preferable to muddled, indirect messaging.
  • "I needed to set aside some of my fear… and just be myself and talk to people… And I could generally temper any of the intimidation that I was worried about by tempering the message appropriately." — Holly Buckley [03:43]

Developing the Next Generation of Leaders

• Stretch Assignments & High Expectations: Buckley advocates for giving promising team members significant responsibilities—what she calls "stretch assignments"—without preconceived limitations.
  • "Don't put your self-imposed limitations on somebody. They will often far exceed your expectations if you let them try." — Holly Buckley [05:20]
• Visible Decision-Making: She believes in making her own thought processes transparent to emerging leaders so they can gain pattern recognition and develop their individual styles.
  • "Make decision making visible… let them see how I'm thinking about it… They will likely have a different leadership style than I do… but by letting people see your leadership thinking… they can then use that to inform their own style." — Holly Buckley [06:01]

Maintaining Morale and Trust Through Ups and Downs

• Avoiding Overreaction: Buckley notes the importance of not being "overly reactive" to daily fluctuations in morale.
  • "It's very easy, as an action-oriented person, to hear things and feel like you need to immediately act upon them… that often isn't always the right answer." — Holly Buckley [08:26]
• Balanced Communication: She emphasizes knowing the right moments to communicate and fill informational gaps, but advises against excessive reaction to every complaint or rumor.
  • "Trying to be candid, clear, and communicative is really important, but just not overly doing that and overly reacting to everything you hear." — Holly Buckley [09:15]

Host Reflections and Memorable Moments

• On Leadership Growth: Scott Becker praises Buckley’s growth:
  • "I've been a firsthand observer of your evolution as a leader, and it's been remarkable… exceptional." — Scott Becker [04:18]
• The ‘Let It Go’ Principle: Becker echoes Buckley's thoughts with a relatable metaphor:
  • "If you see something that disagrees with you… you're not required to write a three paragraph essay responding to it… so many things in leadership… somewhere in between is often the right balance." — Scott Becker [09:45]
• On Taking Action: Buckley reflects on not needing to act on everything immediately:
  • "It's amazing—sometimes if you don't immediately act on things, sometimes they just take care of themselves." — Holly Buckley [10:38]

---

Notable Quotes & Timestamps

• "The high level vision is what each executable needs to be measured against." — Holly Buckley [00:45]
• "I realized that I needed to set aside some of my fear… and just be myself and talk to people." — Holly Buckley [03:35]
• "Don't put your self-imposed limitations on somebody. They will often far exceed your expectations if you let them try." — Holly Buckley [05:20]
• "Make decision making visible… letting them see how I'm thinking about it…" — Holly Buckley [06:01]
• "Trying to be candid, clear, and communicative is really important, but just not overly doing that…" — Holly Buckley [09:15]
• "Sometimes giving things a little bit of time to mature… sometimes they just take care of themselves." — Holly Buckley [10:38]

---

Important Segments & Timestamps

• Vision and Execution — [00:41]
• Lessons from Setbacks — [02:10]
• Developing New Leaders — [05:03]
• Maintaining Team Stability in Uncertain Times — [07:54]
• Host Reflections and Wrap-Up — [09:25 - 11:12]

---

Tone and Style

Throughout the conversation, both Becker and Buckley maintain a candid, down-to-earth, and encouraging tone. Buckley is introspective and practical, openly sharing her missteps and learnings. Becker is affirming, reflective, and adds light-hearted analogies that emphasize the value of balance and authenticity in leadership.

---

This episode offers actionable leadership wisdom and relatable first-hand experiences for professionals striving to grow as leaders in any high-pressure service environment.

Transcript

[A]

This is Scott Becker with the Becker Business and the Becker Private Equity Podcast. We're thrilled today to be joined by Holly Buckley. Holly's the leader of the healthcare department at McGuire woods and she also works at the intersection of health care and private equity. We're going to talk to Holly today about leadership and talk about a number of different subjects related there. So the first question, Holly, I'll ask you is this. You've had this great leadership career. You've been an incredibly evolving and learning leader. How do you tend to balance your vision and strategy with execution and getting things done? How do you think about those things?

[B]

Thanks, Scott, and thanks for inviting me to join you. I think you've got to consider them as a closed loop system versus a trade off of one versus the other. And the high level vision is what kind of each executable needs to be measured against. And I think that's where it makes it really helpful to have a strategic plan. And at the firm we have a kind of a firm wide strategic plan. And then at the department we have our own strategic plan that's derivative of the firm's strategic plan. And it's really helpful when you're looking at executable tasks and particular things that you're focused on to say, is this consistent with the strategic plan? So you kind of have that guiding light. And where it's not, it becomes much easier to set it aside or terminate it and say that's not what we're going to focus on right now. And then kind of reorient what you do need to focus on. So I think it's just important that you're continually coming back to the vision and saying, is this consistent? And then it's got to pass a much higher bar if it's not consistent with the overall strategic plan and vision.

[A]

Thank you very, very much. And talk about in leadership, talk about if you've ever had a setback and what you've learned from that setback or a challenge or something that sort of went the way you didn't want it to go. That led to great learning. Any thoughts there?

[B]

Yeah, and I think for me it's less of a specific event and more of a evolution. And so people have always commented that I'm a direct communicator and others have taken it a step further and said that I can be intimidating, which I find I'm always somewhat surprised by, which maybe shows a little bit of a lack of self awareness, but I don't think I should be intimidating to people. But apparently some People I am. And so when I was first in the department chair role, I would often be hesitant to communicate directly with people, especially people who are a lot more junior than myself, or if I had to deliver a tough message, because I was worried that the message would come across a lot stronger than it needed to. It was maybe a course correct versus something really serious. And I would often try and send the message through somebody else, someone kind of in between, so as it didn't come across too heavily or. And intimidate someone or make them feel worse than they needed to. And it was really just a kind of a minor thing. But I realized over time that my message was getting lost and it wasn't being delivered how I would deliver it. And the. The. Yeah, the message was just not the right message. It wasn't the message I wanted to be communicated. And so by me not communicating myself indirectly, it was. It was missing the. Missing the boat. And so I realized that I needed to set aside some of my fear of being direct or intimidating and just be myself and talk to people when I felt that I needed to talk to them about what I needed to talk to them about. And even if it maybe did come across in, you know, as direct or in an intimidating manner, it was still better than being indirect and going through someone else. And I could generally temper any of the intimidation that I was worried about by tempering the message appropriately. So I think that was probably my biggest learning and coming into this role.

[A]

Thank you. And I, quite frankly, have been a firsthand observer of your evolution as a leader, and it's been remarkable how much you've grown and matured as a leader over the last decade. It's really remarkable to watch and just exceptional. Think a little bit about. You've done a great job. And I view it as one of the critical characteristics of. Of leadership, of developing the next generation of leaders. How do you think about cultivating the next generation of leaders and any thoughts or pieces of advice for people that you look for as you try and nurture people and develop people. But what you've done with the next generation, I view, is so important. Take a moment and talk about any thoughts or advice there?

[B]

Yeah, I think probably a couple of things. I think one of them, and this is applicable in terms of legal skills as well as leadership skills, but it's the idea of stretch assignments and not thinking about what somebody's ceiling is and what an appropriate task is, and really just trying to kind of throw the world to someone and letting them fail, but with a Safety net is a great way to let someone excel. So don't put your self imposed limitations on somebody. They will often far exceed your expectations if you kind of let them try. When you've got someone who you believe is the next generation leader because they've demonstrated those traits as being a total self starter and having a can do attitude and just continuing, continuing to put themselves in the, in the position of somebody above them, letting them soar, they will often do. And I think the more practical advice I'd give is to make decision making visible and to potentially overshare some of the time with some of those next generation leaders in terms of some of the things that I'm dealing with and thinking about and let them see how I'm thinking about it and considering it and the factors that I'm weighing and even the back and forth that I may go through so that they build some pattern recognition in terms of what I'm doing and how I'm doing and why. And they will likely have a different leadership style than I do. And I think for most of us, we've modeled ourselves on multiple other people to kind of find the authentic leadership style that works for us. But by letting people see your leadership thinking and decision making, they can then use that to inform their own style and how they're going to become a leader in the future or today.

[A]

No, And I think that's fantastic. And I think that transparency and decision making and talking about things and working through them is so important to maintaining trust and growth in people. Talk a little bit about. We've already talked a little bit about how your leadership approach has evolved over the years. And I've watched it talk for a second about maintaining sort of trust, morale, positivity, when there's periods of disruption, when there's challenges in morale, when people are overwhelmed. How do you sort of work to make sure you sort of keep people stable and centered and calm through different periods of challenges in the professional services environment, Workflows go up and down when they're really busy, people are stressed or they're not busy enough, people are stressed. How do you sort of maintain that centered notion of. Through periods of ups and downs?

[B]

Yeah, I think it's a couple of things and I think some of them are kind of opposite. So on the one hand I try not to be overly reactive. And so one thing that I found is probably a slightly younger leader in the scheme of law firm leadership is that because I'm closer in proximity to some of the more junior folks than some of Our more senior leaders who may be sitting in my role in other places in the firm. I probably hear more, I don't want to call it noise in a dismissive way, but more noise than more senior folks in that I get a lot of the chatter and a lot of the, a lot of any discontent might get to me a lot quicker than it might get somebody more senior. And it's very easy as an action oriented person to hear things and feel like you need to immediately act upon them and do things. And that often isn't always the right answer. But on the other hand it is knowing kind of when to communicate, when to speak and share, share truth, some realities and fill the void so that, you know, rumors and chitter chatter doesn't fill that. And so I think trying to be candid, clear and communicative is really important, but just not overly doing that and overly reacting to everything you hear.

[A]

But I think that's so important not to be so reacted to everything you hear because it leads to this yo yo kind of management, almost like a ping pong type of management versus a little bit like, okay, I hear you. We're working through this, we're figuring it out. Thank you so much. I couldn't agree with you more. I love that take on it, quite frankly, it's not having to react to everything I saw. The, you know, one of my favorite things I saw yesterday was somebody saying that, you know, if you see something that disagrees with you on Facebook, you know, you should remember that you're not required to write a three paragraph essay responding to it. You're free to just let it go. And I think so many things in leadership, one of the best leaders I ever worked with was a kind of laissez faire leader and would let a lot of things go unless they were really important and wasn't overreacted to everything. And I was never as laissez faire as that person. But somewhere in between is often the right balance. And I, and I love that concept and take.

[B]

Yeah, I think that's right. And I think I probably err a little bit towards your direction of feeling the need to act on things as soon as they happen. But it's amazing sometimes if you don't immediately act on things, sometimes they just take care of themselves. And sometimes giving things a little bit of time to mature and either evaporate or to actually become something that's timely.

[A]

Right, Got it, got it. No, thank you. I could not agree more. And so forth is great. Holly, you are a remarkable leader. I appreciate you so much spending time with us today on the Becker Business and Becker Private Equity podcast in talking to us about leadership. I've watched your leadership evolutions, but nothing short of remarkable. Thank you for joining us today.

[B]

Thank you. Have a great week.