Dinsmore Women's Week Q&A: Anna Dailey

Anna Dailey's Path to Equality

As part of Dinsmore Women's Week, we are highlighting a number of the fantastic women who help make Dinsmore a thriving national entity. Next up is Anna Dailey, who truly embodies the struggle for equality and ultimate triumph female lawyers have faced over the last half-century. Until this month, Anna was the office managing partner in Charleston, West Virginia. Learn more about her below.

1. What is your current role at Dinsmore, and can you describe your career path to success thus far?

I am an equity partner and serve on Dinsmore’s Board of Directors and our Executive Committee. I am concluding a second three-year term at the end of this year. I was also the Charleston office managing partner for six years until I happily turned over the reins to Ashley Pack this month. I turned 65 this past May and will enter my first year of senior partnership in January of 2020.

My path to success was as tortuous as any winding road in Southern West Virginia. I went through high school in three years, starting in Los Angeles, second year was in Buffalo, NY and the final year was in Tullahoma, TN. I wanted to attend Vanderbilt University, only an hour’s drive from Tullahoma. My high school counselor told me not to apply to Vandy because someday I would get married and have children, and I had no business taking a spot at Vanderbilt that could be filled by a man instead. Rather, I should attend Motlow Community College. When I told my father, he said I could go to whatever college accepted me.

I started Vanderbilt in 1971, but all too soon, I discovered music, fun, and a hippie lifestyle. By my second year, I had stopped attending classes without withdrawing--a colossal error in judgment when it came to my grade point average. I was also clocked doing 108 mph in a 90 mph zone on my way from Nashville to Atlanta for a Frank Zappa concert, an escapade that made my father say he would no longer "put jet fuel into a prop plane." I moved in with my parents, who had moved to Huntington, WV, where I got a minimum wage job as a psychiatric aide in a state mental hospital. After a year, I was ready to return to Vanderbilt, this time paying my own way by using my savings and working in the campus library, where I could also study.

While I did well enough on the LSAT to be accepted to law schools, my grade point average suffered from that semester of all F’s. An attorney friend of my father’s, Jim Porter of the prestigious Huddleston Bolen firm, interviewed me and agreed to write a letter of recommendation for law school. It was five pages long, as he had to explain why he was recommending me despite my colossal errors in judgment during my freshman and sophomore years. Thanks to Mr. Porter, I was accepted at WVU law school. However, my hippie days were not entirely behind me, and when I graduated, I took a job at Legal Aid in Martinsburg and spent time trying to unionize farm workers for a salary of $13,500.

Three years later, I jumped at the chance to take a $25,000 job with the federal government in Pittsburgh, representing the Office of Surface Mining. Within two years, my salary had climbed to $32,500. However, bored with the slow pace of that work, I accepted a $30,000 job in Charleston, WV with our of-counsel partner Forrest Roles at his boutique labor law firm that represented several coal companies. Together, we went through some of the most violent strikes in the coal fields, representing Massey, Pittston, Arch, & Peabody. I learned traditional labor law, union avoidance and collective bargaining from excellent mentors. I also made life-long friends with several coal industry people. In the mid-90s, as the tort lawyer replaced the union rep and labor work began to dwindle, I read Who Moved My Cheese and began to learn employment law. By the time our little boutique labor law firm joined Dinsmore in 2003, I was a partner and had tried multiple jury trials, been to the U.S. Supreme Court as co-counsel with now-Chief Justice John Roberts, and my skill set and business generation more than eclipsed the bad judgment of my college years.

Before merging with Dinsmore, we considered merging with a couple different West Virginia firms, but my experience with Dinsmore stood out starkly for its inclusivity. After meeting Susan Zaunbrecher and studying the firm’s website, I knew I had found a welcoming home. Dinsmore had many women superstars; in fact, many were far more successful than me. I was sold! Happily, Forrest Roles and my other partners also liked the idea of merging with Dinsmore. That was 16 years ago. At Dinsmore, I thrived. My client work expanded, and I got the opportunity to help other Dinsmore lawyers and their clients. Each year, I’ve made new colleagues and friends at Dinsmore. In addition, because community involvement is one of Dinsmore’s pillars, I sought out opportunities for more involvement in community and civic organizations. Last but not least, I learned the value Dinsmore’s marketing team can bring to your legal career.  

While my career path was tortuous, it has been successful due to lots of luck, constant intellectual curiosity, and a desire for success that motivated me to work hard.

2. Dinsmore has repeatedly been named a top national firm for women. How has the firm’s focus on inclusion and equality benefited you personally?

When I interviewed with Dinsmore in 2002, I saw that Dinsmore had a higher percentage of women attorneys and women partners than my prior experiences and many of the women partners were far more successful than me. Dinsmore's women attorneys were not brief-case carriers or spending a life-long career as second chair, as I witnessed in many West Virginia firms. The expectations at Dinsmore were different: Women partners could be, and were, much more. Because the firm’s financial information was open and transparent, I saw women were as financially successful as men. I also saw women partners appointed and elected to leadership roles.   

In this environment, I have benefited personally. But, I have to add that one of my happiest experiences at Dinsmore is witnessing women assume leadership roles at much younger ages. Inclusion and equality have given women lawyers opportunities that were very rare during my 40-plus-year career. I also think it’s significant that Dinsmore works with lawyers who need or want to be able to work part-time and part-time lawyers can still be partners in the firm.

3. What advice do you have for women starting their careers?

I have five items of advice, but the first four apply to both men and women starting their careers:

  • First, learn to be a really great lawyer.
  • Your career/workplace relationships are more like a movie than a snapshot. Do not make a life-changing decision based on a few snapshots; it’s the movie you need to be judging.
  • While billable hours are important, so is the occasional non-billable exercise of intellectual curiosity or a deep dive on an issue you may not be able to bill for in this era of insurance-company-mandated restrictions. Do not let those rules stop you from digging in so you can become a great attorney.
  • Avoid youthful indiscretions like mine.
  • Women, you can learn a lot from being second chair. But understand you need to eventually become the solution to your clients’ legal problems. Doing that requires you to gain and display the confidence to take the reins and step out of that shadow. Career success means people want YOU to give the advice. This does not mean you stop being part of teams or turn down work.

4. What was your first job, and what is your best story from your time working there?

My first full time job was as a psychiatric aide in a state mental hospital. While there, I witnessed one of the other aides mistreating a patient, and I reported it to the charge nurse. I was later called to the hospital administrator’s office, where I was reprimanded. That’s when I decided I needed to finish college and go after that law degree I dreamed of while watching Perry Mason.

5. What’s something people would be surprised to learn about you?

See my response to Question 1 above. There are all kinds of surprises there. The last surprise is that I grew up in Canada from first to the start of eighth grade.