Chicago Legal Search, Ltd.

Personal Life

Gary A. D'Alessio has owned Chicago Legal Search, Ltd. since 1988. Prior to founding his company, Gary practiced law for more than five years at McKenna, Storer, Rowe, White & Farrug. For the past twenty-seven years, he has been a legal search consultant, who is very knowledgeable about the Chicago legal market and well-known in the legal recruiting industry. The former practicing attorney has been quoted on a wide range of topics regarding the legal profession in the Chicago Lawyer and Chicago Daily Law Bulletin as well as the Chicago Sun-Times. According to Gary's LinkedIn page, he has also been published in the American Bar Association's “Changing Jobs: A Handbook for Lawyers for the 1990's” and the Young Lawyers Section of The Chicago Bar Association's “Lawyers' Guide to the Chicago Job Market.” His company focuses on placing candidates in the Chicago metropolitan area, but also has joint venture affiliates in different cities that can place candidates anywhere in the United States. His company is ranked 14 in LawCrossing's 2013 Most Influential Legal Recruiters List.


Gary was born in Philadelphia, Pennsylvania, and was raised in the city of “Brotherly Love” and southern New Jersey. He grew up in a very supportive Italian American family and is the second oldest of four children. The legal recruiter graduated with a B.S.B.A. cum laude from Villanova University. He earned his J.D. from Tulane University School of Law where he formed a social organization called The Bar Review.

Gary is an entrepreneurial businessman as well as an avid traveler, having been to six continents. His favorite places are New Zealand, Sydney, Australia, Zurich, Switzerland, Tokyo, Japan, Madrid, Spain, Stockholm, Sweden and Lake Como, Italy. Gary said New Zealand is the “most beautiful place he has ever been.” While visiting Queenstown, New Zealand, he had the opportunity to go bungee jumping and paragliding. The legal recruiter said that the people of Sydney are “so friendly and a lot of fun.” He plans on visiting Antarctica in the future.

Gary also enjoys going to the movies, reading and spending time with his family and friends. Although he doesn't have a favorite book, Gary likes to read John Grisham and David Baldacci novels. He loves to eat at Mia Francesca, a restaurant that “features the zesty, earthy cuisine of Rome and the surrounding areas of Tuscany, Umbria and Lazio,” according to the restaurant's website. The recruiter said Italian food is his favorite cuisine and that Mia Francesca has a “nice vibe. It's not too big or pretentious and the food is consistently good.”

He roots for the Chicago Cubs and Bears. Gary lives five blocks from Wrigley Field and can see the field's bleachers and scoreboard from his roof deck.

Gary's Successful Career Path and Tips for Legal Recruiters

Gary was asked what it takes to become a successful legal recruiter. He listed three main qualities. He stated, “First and foremost, you need to really enjoy talking to and meeting people. You should always be actively recruiting candidates.”

Gary continued by addressing the second trait a recruiter should possess. He declared, “Persistence and fortitude. You must have a positive, upbeat attitude. If things didn't work out today, tomorrow is another day.” The legal recruiter called this feature a “gung ho attitude.”

The third point Gary pointed out was that legal recruiters should have a “professional attitude and be ethical because their professional and personal reputation is the primary reason clients and candidates chose to work with them.”

Did Gary transition into working as a recruiter or was he always involved in the field? The recruiter answered, “It was completely fortuitous. I was a litigator and received a call one day from a Chicago-based recruiter, who was originally from Connecticut, about another law firm job. When I told her I was from New Jersey, we had this rapid-fire conversation and immediately connected. She said her search firm was looking to hire a legal recruiter and said “You sound great on the phone. Would you consider working for us?'”

What motivated Gary to work as a legal recruiter? Was it just a simple phone call that lured him into the profession? He replied, “That recruiter's call was the genesis of my career switch, but I've always wanted to help people in some way.” The legal recruiter acknowledged that he has made an impact on so many people's lives; not just those of the candidates he has worked with, but also those of their families and friends. He claimed, “I feel professionally and personally satisfied whenever I can make a difference in people's lives and careers. I have helped a lot of people along the way, giving them guidance and multiple resources to use in their job search.” Gary added that he believes in being very candid and straightforward with people so they know where they stand.

The businessman talked about what he is known for professionally. The recruiter proclaimed, “I am known for my company, which is one of the oldest and largest legal search firms in Chicago. My company is consistently ranked in the top three in this city, which is the third largest legal market in the country. I'm also known for having successfully developed and maintained longstanding relationships with both clients and candidates. I am well-entrenched and respected in the Chicago legal community, and have earned an impeccable reputation.”

Gary also talked about his strengths and weakness as a recruiter. His strengths are “experience, knowledge and well-established client and candidate relationships.” As for weakness, Gary simply stated, “I always want to improve myself.”

When asked if he had a mentor, Gary asserted, “In terms of legal recruiting, I have been self taught.” He revealed he has been a mentor to many recruiters over the years. The legal recruiter stated, “I have only hired one recruiter who had prior legal recruiting experience so I have taught dozens of legal recruiters while running my company. Teaching is in my blood. My dad was a teacher and I was a substitute teacher and tutor while in college and law school. It's a role I truly relish.” Gary admitted that his family, especially his parents, had the most inspiring influence on him.

Gary gave his advice to new recruiters, highlighting two points. He said new recruiters “need to have extraordinary people skills.” Secondly, they need to “understand and appreciate the tremendous financial upside of a commission-based compensation structure as they are typically not paid a base salary. Also, there are highs and lows in recruiting so they cannot be risk adverse and have to maintain a positive attitude.” The legal recruiter added, “You must have a true love and passion for recruiting and helping people, and not be motivated solely by money to do this long-term. You should always do the best you can for your clients and candidates.”

Considering his twenty-seven years of experience in the legal recruiting industry, many readers may want to know where Gary sees the legal field in the next five years. The former litigator noted, “More AmLaw 200 law firms and intellectual property boutiques will consolidate, merge or dissolve in the next few years. Fewer new law school graduates will be hired by law firms because they have no practical experience and firms' clients don't want to get billed for services provided by first-year lawyers since they are being trained at the clients' expense. A premium will be put on hiring lateral attorneys, especially partners with significant portable books of business.” Gary also mentioned that more in-house attorney hiring will occur to help reduce outside legal costs.

What does Gary look for to find the right fit? What makes a great candidate? The successful recruiter said, “Due diligence. I like to meet with clients to get a better sense of their culture and working environment. I flush out to the “nth” degree their ideal job criteria before meeting with my candidates to make sure there is a potential good fit. The client's favorable perception of the candidate is critical in the hiring process. You really need to be probing in your questions as well as an effective listener to ensure you're properly qualifying your candidates.”

The recruiter said a great candidate “has to fit the client's substantive and cultural criteria. He or she must meet the requisite areas and levels of expertise, plus have a transferable skill set and compatible personality. Is this candidate a team player, self-confident, but not arrogant, capable of effectively dealing with clients and able to develop business? A critical part of the equation is one's personality. On paper, a candidate may have excellent academic credentials and great experience, but when you meet him or her, there may be a disconnect so he or she may not be as presentable, likable or marketable as you had hoped. I always tell candidates that timing is truly everything in one's career and life.”

So what is Gary's recipe for a perfect match? The recruiter confessed, “Both the client and candidate must be in sync. There needs to be a mutually positive feeling about each other. Both parties are looking for a successful, long-term relationship versus merely filling a job opening.”

Gary is a very confident businessman who doesn't get rattled easily. What is his biggest concern? How does he overcome fear? The legal recruiter was asked if he was concerned about another recession. He answered, “I've been through several recessions in my career. I'm always concerned about the welfare of my employees. Are they happy and enjoying what they are doing, and are they successful. I have never laid off anyone because of economic reasons. I care about them as individuals and consider them my colleagues, and don't treat them as just workers.”

The recruiter acknowledged that he overcomes fear with a “positive mindset. I always try to be forward thinking and rely on my years of experience. I have a positive attitude and approach things in a positive way. I'm generally calm, cool and collected, and try not to be too emotional.” Gary stated he hasn't faced many obstacles. He admitted, “I have a blessed life, supportive family and close friends and colleagues. I always tell people I'm not an optimist or pessimist, but a realist. My life experiences have been positive. Knock on wood, everything has been going well. I believe that health and happiness are really the keys to success.”

Has Gary learned something of value from his mistakes? The recruiter laughed and said, “Oh, sure. I hope you always learn from your mistakes. It's part of one's character, to grow and evolve since we're all fallible. You need to first acknowledge your mistakes and then learn from them so they don't happen again.”

So where does the businessman derive his confidence? The recruiter expressed, “It's a combination of things, including my experience, wisdom and knowledge about legal recruiting. Also, it's my basic personality. It's really important to be self-confident because candidates trust me with their careers and livelihood. Their next career move is in my hands and I take that very seriously. Earning the respect of my clients and candidates, and a healthy dose of self-confidence [is what I do].” This is what enables Gary to remain confident not only at work, but also in his life.

After nearly twenty-seven years in the legal recruiting business, Gary is still motivated every day because he enjoys making a “real impact on the careers and lives of so many people by either placing them with my clients or helping them with their job search to find a position on their own.”

His greatest accomplishment has been establishing his company. Gary stated, “I have developed a phenomenal reputation in the Chicago legal community. My pride and joy is how much Chicago Legal Search has impacted thousands of candidates' lives.”

Membership with Associations, Number One Priority Outside of Work and Future Goals

Gary holds a membership with the National Association of Legal Search Consultants (NALSC). The recruiter explained that they have a code of ethics and that clients can also join the organization. However, the majority of members are legal recruiters and search firms. The businessman also is affiliated with the National Association for Legal Professionals (NALS), the Chicago Bar Association, the Illinois Bar Association and the American Bar Association.

The legal recruiter made it clear that his number one priority outside of work is to “maintain a healthy and happy lifestyle. I don't dwell on work. I try to enjoy life. I think about work a lot since I run my own company, but I try not to eat, drink and sleep work.” Gary said he has no plans to retire in the foreseeable future because he loves what he does. He's already booked travel plans trough October 2013, heading to Florida, Palm Springs, California, his niece's wedding in Philadelphia, the Jersey shore, Cape Cod and a cruise in Europe.

Gary's professional goals are “to continue to increase the reputation of Chicago Legal Search and continue to make an impact on people's lives.” Personally, Gary plans on going to Antarctica, the seventh and final continent for him to visit, and staying healthy and happy.

See Chicago legal recruiters ranking on LawCrossing.