Becker Private Equity & Business Podcast
Holly Buckley on Bad Career Advice and Breaking the Mold in Big Law 6-3-25
Tue, 03 Jun 2025
In this episode, Holly Buckley, Chair of Healthcare at McGuireWoods, joins Scott Becker to share two pieces of the worst professional advice she received.
Chapter 1: What is the worst career advice you've ever received?
This is Scott Becker with the Becker Private Equity and Business Podcast. We're thrilled today to be joined by Holly Buckley. Holly leads the healthcare department at McGuire and Woods. She works at the intersection of healthcare and private equity and is a tremendous leader, a force of nature.
We're going to talk to her today about a subject that we don't often get to visit with, but used this subject recently with another guest and just had a wonderful podcast. The podcast topic today, Holly, is what's the worst career advice or professional advice you've ever received? You don't have to note who it was from.
I hope it wasn't from me, but, but give us a second on what, what do you think of as bad career advice? What have you heard? What have you ever been told? Give us a few thoughts on what is bad career or leadership advice?
Oh, uh, it's funny. Cause I think that the two things that first, uh, came to mind are probably not very profound or helpful to, uh, a broader audience, but I will share them nonetheless, just because they're the first thing that came to mind and you took me by surprise with the topic. But I think maybe there's a broader lesson that can be pulled out of them.
Chapter 2: How did a professor's opinion shape your career?
So the first was when I was in law school and I was looking for work after law school. And I'm a first generation lawyer in my family. And I didn't really even know what a law firm was. When I went to law school, I kind of knew I was doing healthcare transactions and didn't really know the venues to do that.
And there was a particular professor that had a pretty defined view of what a big firm lawyer looked like. And he told me that he did not think that I was big law firm material and that maybe I should seek a job in government, which is obviously a great place to work also and has a lot of opportunities.
He judged me based on his perception of what he felt big law was and what government was and what he thought I was capable of or fit for. And it was a surprise to me that he would have made that pronouncement. And he apparently was wrong because I'm pretty, pretty far in on big law and have done relatively well for myself. And I think
Maybe the lesson from that is don't let others project onto you their impressions and go with your own gut and make your own decisions and freely try to decide the advice of people.
Chapter 3: What lessons can we learn from bad advice?
Yeah, so let's take a second on that because I think that's absolutely fascinating because there's so many different ways. One is I'll vouch for Howie. She's become an equity partner, a leader, one of the top lovers in the country, does tremendously well in leadership and in debt for clients.
economically does well, all those kinds of things and also runs a fantastic family with her husband and two daughters. So in terms of her success, it's been incredible success. It continues to grow in that success. So obviously you ended up being right at this and choosing where you ended up doing.
The second thing is I always have this concept I work with and almost anything anybody's ever done successfully and there may be exceptions to this, there are going to be naysayers. And I'm a huge believer in the concept, don't believe the naysayers, and thank God how he did it.
Third is, and I'd like to dig into this a little bit further, the person who gives that kind of guidance, when he gave that guidance, and I think it's a he, I'm not sure, but you'll tell me, or he or she, because I might know who you're talking about, I'm not sure, but that person said, probably did it with your best interest at heart versus in a negative way. But help me work through that.
Chapter 4: How to deal with naysayers in your career?
What was your perception of that? Were you taken aback? Did you view that as fuel for your fire? I know that I have a daughter who's incredibly talented, incredibly motivated. And if you ever tell her she can't do something, She may be upset for the moment. And when she's upset sometime, I will make the mistake once in a while of coddling her. And that goes very poorly.
And then she jumps back after whatever she's trying to do. She's quite determined and has a high motor. And then ends up doing whatever. I told her, oh, don't worry. It's OK. And she goes after it. How did it feel? Was the advice meant in a good way? And how did you respond to that advice?
Sure. I don't think the advice was meant in a good way. And I was taken aback and it was fuel for the fire. In hindsight, I think the advice was given based on this person's perception of what a really good big law junior associate looked like. And I don't know that that was necessarily me. And I did do relatively well as a junior associate.
I think he perceived that I was not someone who would kind of quickly fall in line, put my head down and just do exactly what I was told. And he, there was a certain kind of group of associates or of law students that this particular person would tend to support more. And they tended to be people who are much kind of quieter and fall in line.
And I didn't really fit the mold that he thought you needed to be successful. Now, I think that the world has changed a lot. And I think we now expect more junior folks to be bigger thinkers and to push us as more senior people. And so I think his view was maybe a little antiquated. I don't think it was ill-intentioned when he said it.
I think it was his genuine belief that I wouldn't necessarily do well.
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Chapter 5: What does it mean to break the mold in big law?
Chapter 6: How has the perception of law firm success changed?
And I didn't really fit the mold that he thought you needed to be successful. Now, I think that the world has changed a lot. And I think we now expect more junior folks to be bigger thinkers and to push us as more senior people. And so I think his view was maybe a little antiquated. I don't think it was ill-intentioned when he said it.
I think it was his genuine belief that I wouldn't necessarily do well.
I mean, there's so much there. People that don't know Holly, she has a big personality. She's a natural leader. And they might discount the fact that she's also incredibly bright. She graduated from high school at 16, went on to college at 16. That's incredible. And I tell the story often because it shows sort of the motor and intelligence of the person.
But if you don't know Holly well and you judge the book by the cover, you might think it's all big personal skills and not brilliant and hardworking as well. And Holly's incredibly hardworking. She's incredibly gifted and smart. And so what happens is in these early years as an associate, the pendulum is much more focused on smart and task oriented. Just you get things done and are you smart?
And then in big law, as you move up several years, it becomes much more balanced up. What are your management skills? What are your ability to get other people to get stuff done the right way? What are your abilities to work with clients?
And so as I listen to what you're saying and I hear this, he might have misjudged your sheer intelligence and work ethic, which is a key part of success in the early years. And then as you get further into law, it's this mix of management skills, leadership skills, personal skills. to go with very, very bright and very hardworking.
And it's a fascinating thing because the most successful lawyers at the big firms, at the biggest firms, are often really smart people. We have another colleague who's a valedictorian who breaks the mold on this, but he was also brilliant and a great team leader. But sometimes our valedictorians are so good at being students. And I remember a brilliant Chicago lawyer we had who was brilliant.
but couldn't get past the task thinking into the bigger thinking of how are we going to really take care of clients and help them move their business forward. And it's people like Holly that have that mix of all those skills and those skills to the mistake of the person who gave you this advice,
Those skills, if you get through the first few years, become as much or more important of the skills in the long term of a career. So it's a fascinating perspective that he had versus the antiquated view that he had versus what really is what makes it go over the long run. That's fascinating. Holly, let me let you continue to double down or give us another piece of horrible advice you got.
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