Holly Buckley on Bad Career Advice and Breaking the Mold in Big Law 6-3-25

Summary

Becker Private Equity & Business Podcast Summary
Episode: Holly Buckley on Bad Career Advice and Breaking the Mold in Big Law
Host: Scott Becker
Release Date: June 3, 2025

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Introduction

In this insightful episode of the Becker Private Equity & Business Podcast, host Scott Becker welcomes Holly Buckley, a leading figure in the healthcare department at McGuire Woods. Holly brings a wealth of experience from the intersection of healthcare and private equity and is celebrated as a dynamic leader in her field. The central theme of the discussion revolves around the worst career and professional advice Holly has encountered and how she has defied expectations to achieve success in the competitive world of big law.

First Bad Career Advice: Doubting Her Fit for Big Law ([01:04])

Holly Buckley opens up about a pivotal moment in her early career when a law school professor doubted her suitability for a career in big law. As a first-generation lawyer specializing in healthcare transactions, Holly was navigating uncharted territory. She recalls:

“A particular professor 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.”
[01:04]

This unexpected criticism was based on the professor's narrow perception of the ideal big law associate—someone who quietly followed directions without challenging the status quo. Holly, with her strong personality and leadership qualities, did not fit this mold. Despite the discouragement, she pursued her passion and proved the professor wrong by establishing herself as an equity partner and a respected leader at McGuire Woods.

Overcoming the Naysayers ([02:41])

Scott Becker commends Holly’s resilience and highlights the importance of ignoring naysayers. He emphasizes:

“There are going to be naysayers, and I'm a huge believer in the concept. Don't believe the naysayers and thank God. How she did it.”
[02:41]

Scott reflects on how Holly’s success exemplifies the necessity of maintaining confidence in one’s abilities despite external doubts. He also notes that Holly’s intelligence and work ethic are critical factors that the professor may have underestimated during her early career stages.

Holly concurs, explaining that the advice she received was not malicious but rather a result of the professor’s outdated views on what constitutes a successful big law associate:

“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.”
[05:57]

Second Bad Career Advice: Dress Codes for Women ([08:26])

Shifting focus, Holly discusses another prevalent piece of misguided advice aimed at junior women in the workplace—specifically, the pressure to invest in expensive attire to make a professional impression. She states:

“Women need to probably let other women be unless asked. And in general, remember that people come from different levels of wealth and recommending people buy Armani suits and very expensive shoes may not resonate too well with others.”
[08:26]

Holly criticizes this advice as both insensitive and impractical, arguing that it overlooks individual financial circumstances and places undue emphasis on outward appearances rather than professional competence and personal growth.

Scott’s Agreement and Broader Implications ([09:44])

Scott Becker wholeheartedly agrees with Holly’s perspective on dress codes, emphasizing the importance of professional decorum without the necessity of extravagant spending:

“Having to show off to a fancy car or fancy clothes or that somehow that is a substitute for great substance and energy and drive is I think such misguided advice.”
[09:44]

He reinforces the idea that investing time and resources into self-improvement and career development should take precedence over superficial measures like wardrobe expenses. Scott’s alignment with Holly’s views underscores a broader shift towards valuing substance over style in professional settings.

Lessons and Insights

Throughout the conversation, Holly and Scott highlight several key takeaways:

1. Trusting One’s Instincts: Despite receiving discouraging advice, Holly’s decision to follow her passion and instincts led to her thriving career in big law.

2. Challenging Outdated Norms: Holly’s experiences illustrate the importance of breaking away from traditional molds and advocating for a more inclusive and diverse understanding of success in the legal profession.

3. Supporting Women in the Workplace: The discussion on dress codes emphasizes the need to respect individual choices and financial situations, advocating for a more equitable and supportive work environment for women.

4. Balancing Personal and Professional Life: Holly’s ability to excel professionally while maintaining a strong family life serves as an inspiration for achieving work-life balance.

Conclusion

In this episode, Holly Buckley shares her journey of overcoming misguided career advice and challenging conventional expectations within the legal industry. Her story serves as a powerful reminder to trust oneself, embrace unique strengths, and advocate for a more inclusive and supportive professional landscape. Scott Becker’s thoughtful questions and reflections further enrich the discussion, providing listeners with valuable insights into navigating and succeeding in the competitive world of big law.

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Notable Quotes:

• “Don’t let others project onto you their impressions and go with your own gut and make your own decisions and freely people.” — Holly Buckley [01:04]

• “Having to show off to a fancy car or fancy clothes or that somehow that is a substitute for great substance and energy and drive is I think such misguided advice.” — Scott Becker [09:44]

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This episode is a must-listen for professionals navigating their careers, especially those facing unsolicited advice or challenging traditional expectations. Holly Buckley’s experiences and insights offer valuable lessons on resilience, leadership, and the importance of defining one’s own path to success.

Transcript

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[Scott Becker]

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 Woods. She works at the intersection of healthcare and private equity and and is a tremendous leader, a force of nature. We're going to talk here today about a subject that we don't often get to visit with, but use 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 for me. But but give us a second on what what do you think of his bad career advice? What have you heard? What have you, what have you ever been told? Give us a few thoughts on what is bad career or leadership advice.

[Holly Buckley]

Oh, it's funny because I think that the two things that first came to mind are probably not very profound or helpful to 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. So the first was when I was in law school and I was looking to to 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 do 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 which is obviously a great place to work also and has a lot of opportunities. But 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 far in on big law and have done relatively well for myself and I think maybe the, the lesson from that is don't let others project onto you their, their impressions and go with your own gut and make your own decisions and freely people.

[Scott Becker]

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 at one of the top welfares in the country, does tremendously well in leadership and in depth 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 in 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 like to dig into this a 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 probably did it with your best interest at heart versus in a negative way. But help me work through that. 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 and she's quite determined and has a high motor and then ends up, you know, doing whatever, you know. I told her, oh, don't worry, it's okay, and she goes after it. How did it feel? Was the advice meant in a good way?

[Holly Buckley]

And.

[Scott Becker]

And how did you respond to that advice?

[Holly Buckley]

So 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. But 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, 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.

[Scott Becker]

I mean, 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 how well and you judge the book by the COVID you might think it's all big personal skills and not brilliant and hardworking as well. And how he's incredibly hard working, 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 a much more balance of what are your management skills, what are your ability to get other people to get stuff done the right, 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 hard working. 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 molderness. He was also brilliant and a great team leader. But sometimes our valedictorians are so good at being students. And I remember a brilliant University of 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 Howie that have that mix of all those skills and those skills to the mistake of the. The person who gave you this advice. Those skills, if you get through the first three years, become as much or more important 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. Let me double. Let me let you continue to double down and give us another piece of horrible advice you got.

[Holly Buckley]

I think the other piece of horrible advice that I hear really somewhat frequently, both directly and indirectly for more junior people is around women and their dress codes and different, more senior women's perception of how more junior women should dress in the workplace. And I think these comments in general are very misguided and I think are generally poorly received. So there's one particular line of this around how more junior women should have some very expensive, expensive pieces in their closet. A very expensive suit, say an Armani suit, very expensive shoes, and the message that that sends. And I think those, I mean, this is a totally different topic than kind of the first one, but it was again, the second thing that came to mind. And, and every time I hear these comments, I'm always just shocked that someone would make them. And there is not a scenario where they have been well received. And so I think in general, women need to probably let other women be unless asked. And in general, remember that people come from different levels of wealth and recommending people buy Armani suits and very expensive shoes may not resonate too well with others.

[Scott Becker]

I think this is actually a brilliant comment and it goes to the heart of things. Yes, you got to look sharp enough, you got to look clean enough, you got to look all those things. And I wouldn't discount that I'm not a great dresser, but I believe there's a certain level professional decorum and dress that's needed. Now, that doesn't mean I need a $2,000 suit or an expensive suit, particularly to look sharp and clean. Far more important than looking sharp and clean. In the old days, there's this ad campaign that said images, everything, and sort of to the point that you're making, I think this is the absolute wrongest advice. And sentiment there is out there at all. I think it's very, very important to be professional, come across clean and together. But having to show off to a fancy car or fancy clothes or that somehow that is a substitute for great substance and energy and drive is I think such misguided advice. And I, and I love that you talk about that. I love that. I think you are right on. And I think this concept that people should go out immediately when they start a job and spend thousands of hours on their wardrobe, no, they ought to spend thousands of hours on self improvement, starting to put money away, starting to do other things on the wardrobe is absolutely ludicrous. I could not agree with you more and I love that sentiment. Holly, as always, thank you for joining the Becker Private Equity and Business podcast. We are thrilled today as an aside to bring number one on the Apple Business News podcast today. God bless all of our listeners and our magnificent guest like Holly Buckley. And a special shout out to our producer Chanel Bunger, the best in the business. Holly, thank you so much for joining us.

[Holly Buckley]

Thank you Scott and massive congratulations to you and Chanel. That is just tremendous. And thanks as always for having me on.

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