How is the legal profession evolving, and what does it mean for your career? In this episode, host Tony Sipp welcomes a very special, nationally renowned, guest, Chere Estrin for a look into the future of the legal workplace.

Estrin is a guiding force in the legal profession and a nationally recognized voice on career development in the field. She’s the CEO of Estrin Legal Staffing, the author of 12 books, and the creator of the podcast Lawfully Employed and The Estrin Report blog. 

Hear how to adapt and stand out and what traps you need to avoid in the new world of law. AI has jolted the industry, but it’s not just about technology. Paralegals are being tasked with increasingly complex duties, you’ve got to keep your skills current and show initiative every day. 

Estrin provides insights and advice you can use now, whether that’s in your current job or when searching for your next step. The moves you make today can make or break your career. Start “future proofing” your life and getting ahead now.

Mentioned in This Episode:

The Estrin Report, blog

Lawfully Employed, podcast

“If I Lost My Job Tomorrow, Here’s How AI Would Fix My Resume Before Lunch,” by Chere Estrin

“Hot Flashes, Cool Resume: Still Billable. Still Brilliant. Resumes for Legal Professional Women Who Aren't Done Yet,” by Chere Estrin

“Power Plays” by Chere Estrin

Other books by Chere Estrin, Amazon.com

Previous appearance on the Legal Talk Network, Lawyer 2 Lawyer: “Paralegals: The Backbone of the Law Practice”

International Paralegal Management Association (IPMA)

IPMA 2025 Annual Conference & Expo

NALA, The Paralegal Association

NALA Conference & Expo 2026

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Ever think of hanging up a shingle and going it alone as a freelance paralegal services provider? It can be done and there is a demand. Working in a firm isn’t your only option.

Guest Corrin Swintosky is a freelance paralegal professional at her own company, Lucid Legal Support LLC, who specializes in helping small and midsize law firms increase efficiencies by providing extra help with criminal law cases as needed.  

A former probation officer, Swintosky’s passions include helping expunge criminal records, getting offenders back on their feet and get their lives back on track after minor offenses and missteps. Even a minor mark on a person’s record can create barriers to housing, employment, voting, and everyday life. 

Hear how Swintosky as a one-person show balances tech and business skills, how she learned to work side-by-side with attorneys, and how she leans confidently into her expertise. 

Mentioned in This Episode:

“New York Clean Slate Act Takes Effect on November 16, 2024, With New Obligations for Employers Running Criminal Background Checks,” LawAndTheWorkplace.com 

“It's Time for a Federal Clean Slate,” The Clean Slate Initiative 

NALA, The Paralegal Association

NALA Conference & Expo 2026

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How do professionals in the legal community help protect and enhance the civil rights we all deserve? Guest Capri Maddox is the executive director of the Los Angeles Civil + Human Rights and Equity Department, working to ensure Los Angeles is a city of belonging, justice, and a welcoming space for all. 

She’s an attorney, but she also worked as a paralegal professional, and she recognizes how big projects depend on every level of the legal team. 

As a former prosecutor, Maddox says she knows no city can arrest its way to safety. Described as “a powerhouse of purpose,” she believes the only way to ensure public safety is to make sure everyone feels included, feels represented, and feels that justice works for all, not just a few. 

Her team’s latest campaign is a simple, yet powerful project called “Just Say Hello.” The idea is that if people say “hello” to a stranger once in a while, it can create a friendlier, more inclusive city. As she notes, it’s unlikely someone will mistreat someone if they’ve just said “hello” to each other. Hear how we can all do something in our own communities to ensure everyone feels welcome, respected, safe, and empowered.

NALA, The Paralegal Association

NALA Conference & Expo 2026

Los Angeles Civil + Human Rights and Equity Department 

LAIsForEveryone.com

“LA Civil Rights Celebrates ‘Just Say Hello’ Campaign Citywide for International Friendship Day 2025” 

The LA For All Campaign

“I Belong. You Belong. We Belong. Theme for Fourth Annual LA For All Week” 

LA Law Day 2025

Using social media? The campaigns’ hashtag is #LAIsForAll

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Paralegals can find themselves on an island at the workplace, left without training, mentorship, and opportunities for growth and advancement in a sink or swim environment. It doesn’t have to be that way. 

Guest Eda Rosa is a former paralegal who founded her own firm, Eda Rosa LLC, in 2017. The legal consulting and training company is dedicated to transforming the legal industry from the inside out. Rosa says CLE classes are fine for the nuts and bolts, but what about training to avoid burnout and build “soft skills” that make life and work better? 

Training shouldn’t stop with paralegal classes and company onboarding. Continuous education and team building exercises ensure teams remain strong and develop as a unit. Every player on a legal team has a role, failure to bring along every player hurts the entire firm. 

Hear how Rosa “learned by doing,” growing into her own professional self, earning a master’s degree in law, and then turned her insights into a mission to help paralegal professionals advance their careers and live their best lives both in and out of the office. 

Resources: 

Previous appearance on the Legal Talk Network, Legal Rebels, “What Does the Future Hold for Licensed Paraprofessionals?” 

NALA, The Paralegal Association

NALA Conference & Expo 2026

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We’re at an interesting and dynamic point in time for immigration law, with Supreme Court rulings and presidential executive orders reshaping the field and challenging the system’s status quo. 

The administrative area of immigration law is especially difficult for legal professionals. In an immigration hearing, the judge is essentially on the same “team” as the prosecutor, and because immigration policies are largely under the federal executive branch, the rules seem to shift every four years with a new presidential term. 

Guest Nikki Mehrpoo is a former judge, a scholar, and the first and only California dual certified legal specialist in immigration and Workers’ Compensation law. She is a lawyer as well as a professor of law at West Los Angeles College. She recently created the  MedLegal Professor, a project dedicated to the ethical use of AI technologies in the field of law and medicine. 

In this timely episode of Paralegal Voice, Mehrpoo unpacks recent Supreme Court rulings, executive orders, and even the use of AI facial recognition that are reshaping the field of immigration law. As a legal professional, what we think we know may be subject to change day by day, ruling by ruling. 

Mentioned in This Episode:

Previous appearance on Paralegal Voice, “Digging Into California Workers’ Compensation (Plus, Career Advice From a True Pro)” 

LAPA

Noem v. Perdomo, SCOTUSblog coverage

“Immigration Officers Intensify Arrests in Courthouse Hallways on a Fast Track to Deportation,” Associated Press

“ICE Awards Clearview AI $9.2M Facial Recognition Contract,” Biometric Update “Nevada Judge Takes Creative and Unusual Approach to Combat AI-Generated Fictitious Citations,” LawNext

“The EU Artificial Intelligence Act”

Clearview AI

NALA, The Paralegal Association

NALA Conference & Expo 2026

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The paralegal profession is evolving at breakneck speed, driven by emerging technology such as AI and the era of “video connectivity” brought on by the pandemic. It’s up to paralegal associations to keep up. 

Guests Milady Cambare and Travis Chow are veteran paralegals and the respective presidents of the Orange County and Los Angeles paralegal associations. They share how their associations are working to stay ahead of technology and ensure no member is left behind or left out. 

Today’s information jungle can be beneficial, including social media, Chow says, and paralegals need to keep up with the array of technology. But, Cambare adds, there is still space for in-person events, such as dinner cruises, conferences, and even ice cream socials. As tech takes over more of our lives, she says it’s vital that associations remember the importance of in-person events that connect generations of paralegal professionals.

Cambare and Chow are trailblazers in the paralegal field, envisioning the future of paralegal associations and championing the value of membership, networking, and lifelong learning. Hear how association membership and engagement is more important today than ever before. 

The paralegal profession is evolving at breakneck speed, driven by emerging technology such as AI and the era of “video connectivity” brought on by the pandemic. It’s up to paralegal associations to keep up. 

Guests Milady Cambare and Travis Chow are veteran paralegals and the respective presidents of the Orange County and Los Angeles paralegal associations. They share how their associations are working to stay ahead of technology and ensure no member is left behind or left out. 

Today’s information jungle can be beneficial, including social media, Chow says, and paralegals need to keep up with the array of technology. But, Cambare adds, there is still space for in-person events, such as dinner cruises, conferences, and even ice cream socials. As tech takes over more of our lives, she says it’s vital that associations remember the importance of in-person events that connect generations of paralegal professionals.

Cambare and Chow are trailblazers in the paralegal field, envisioning the future of paralegal associations and championing the value of membership, networking, and lifelong learning. Hear how association membership and engagement is more important today than ever before. 

Mentioned in This Episode:

Google Meet

Zoom

Survey Monkey

Orange County Paralegal Association

Los Angeles Paralegal Association

NALA, The Paralegal Association

NALA Conference & Expo 2026

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Guest and professional legal recruiter Tracey Perkins says in 2025 every paralegal professional should know the importance of technology, especially AI. But she stresses the best paralegals always manage the tech and never let the tech manage them. AI is a tool that can spur efficiency, but it will never replace the mind and analytical skills of a skilled paralegal professional.

In the rapidly advancing world of legal tech, grit matters. You’ve got to keep up. Pushing yourself through even the toughest challenges builds the professional you are destined to become. Perkins is a paralegal professional, educator, and legal industry recruiter who has driven herself forward for more than 20 years. She brings the lessons she learned to every aspect of her life and strives to share each one with every student and every job seeker.

Plus, learn insider tips for when you’re applying for a new position: Don’t include photos on your resume, learn to professionally format everything. Time is money, so get to the bullet points and focus on clear, concise communication. No fluff, no fillers. (And please, no silly email addresses, keep it professional). Hear Perkins’ golden rules for building professional relationships and her pro tips for your LinkedIn page. Get fired up and get hired.

Mentioned in This Episode:

CliftonStrengths assessment

NALA, The Paralegal Association

NALA Conference & Expo 2025

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AI is coming, and it may be coming for your job. Guest Dan Lear, vice president of partnerships at the digital case management company InfoTrack, shares how paralegal professionals can adapt and remain vital. Spoiler, you can’t ignore the AI revolution, but you can learn, evolve, and deliver insights and human skills that AI simply can’t match. 

File, case, and data management has come a long way, from physically moving boxes of paper filings to electronic management, and Lear has done it all, from moving paper files to his current position legal tech. Along the way, Lear advanced from a file clerk position to a career as a paralegal professional, then earning his law degree. Now he’s exploring and embracing AI capabilities.

Having worked as a paralegal, Lear understands how vital the profession is to the practice of law, at times even “training” newly minted attorneys as they transition from learning the principles of the law to actually getting the job done. 

As Lear explains, lifelong learning, networking, and building strong connections will become increasingly important moving forward, whether you’re a newcomer to the field or an experienced veteran. 

Mentioned in This Episode:

“Behind the Curtain: A White-Collar Bloodbath,” Axios

“Tech CEO Warns AI Will Eliminate Jobs. What Can You Do to Protect Your Career?” ABC7 Los Angeles

“The Free-Time Paradox in America,” The Atlantic

Claude AI

ChatGPT / OpenAI

Google Gemini

Off The Record

NALA, The Paralegal Association

NALA Conference & Expo 2025

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Guest Linda McGrath-Cruz worked as a paralegal professional in private practice and in-house (including Royal Caribbean) for 28 years, and she’s a leader for the Paralegal Navigating Perilous Waters cruise, a CLE paralegal conference that takes place on a cruise ship (how cool is that?). 

She is currently the program coordinator and a full-time faculty member in the paralegal program at St. Johns River State College in Florida, a hands-on, real-life program that helps students get jobs and then get the job done. She is also the founder and leader of the social media program Perfectly Paralegal, a community that offers resources, support, and continuing education to paralegal professionals nationwide.

We all need NALA continuing ed credits, but why not make it a family vacation on a cruise ship? Courses on the Perilous Waters cruise are arranged to provide both credits but also leave time for networking, sharing tips, and having fun. Make it a family trip, a friends group outing, or a company event. Learn while you sail. 

Whether it’s in the classroom or on the high seas, McGrath-Cruz is dedicated to sharing what she’s learned with practical teachings that make you better and advance your career. Get excited and get involved.

Mentioned in This Episode:

Paralegals Navigating Perilous Waters Cruise, March 6, 2026 

St. Johns River State College Paralegal Program

NALA, The Paralegal Association

NALA CP exams

NALA Conference & Expo 2025

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Guest Huascar Matos is a paralegal professional and the new president of the International Practice Management Association (IPMA). He has a varied background including a degree in Spanish and time in the fashion and art industry. After an unusual and unexpected path, he has found himself as a director of paralegals at the firm of Foley & Lardner. 

It’s an exciting time for the IPMA as members consider international expansion, the “elephant in the room” of artificial intelligence, and the evolution of a constantly changing profession. AI may shake up the game, but Matos reminds us the legal profession is never static, enduring the shift from paper to e-discovering, the addition of computer capabilities, and other technologies. 

Paralegals, Matos says, will adjust and adapt as they always have. Being part of an organization such as IPMA helps paralegals understand new trends and learn new skills. Robots are not going to take over your job, but AI could help you do it better. 

Hear about Matos’ own career path and the advice he has for those new to the profession. Stepping up, volunteering for new duties, and learning as you go will build your career and get you noticed. Don’t put yourself in a box. Be a “legal MacGyver.” 

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