Conquering Age Discrimination – Turning Experience into Power

Posted on by Chere Estrin

The Charley Lesson: When Experience Speaks Louder Than Age

Charley had spent his career commanding authority, making critical decisions, and leading with confidence. His experience had shaped his reputation as a leader. But after retirement, he found himself in an unexpected position—working as a greeter at Walmart. He didn’t need the job, but he enjoyed the sense of purpose and interaction it provided. He greeted customers with warmth, embodying the same discipline and professionalism that had defined his legal career.

However, over time, Charley began arriving later than scheduled. His young manager, noticing the trend, decided to address the issue. Speaking in a slow, patronizing tone, he asked, “Charley, what would your previous job say if you kept showing up late?”

Charley smirked, pausing before responding, “They’d say, ‘Good morning, Admiral. Would you like a cup of coffee?’”

The manager turned red with embarrassment. He had assumed Charley was just another elderly man with little to offer, not realizing he was addressing a retired admiral—a man who had commanded fleets, managed crises, and built an impressive career on leadership and strategic thinking.

The lesson? Experience, leadership, and competence do not diminish with age. The legal profession, built on precedent, wisdom, and expertise, should be the last place where age discrimination thrives—yet, ironically, it does. Recognizing and overcoming these biases is key to staying relevant and advancing your career.

The Silent Challenge: Age Discrimination in the Legal Field

It is a paradox that the legal profession—a field built on precedent, wisdom, and institutional knowledge—would also be one where age discrimination is quietly taking root. Unlike other industries where seniority commands respect, the legal profession often prioritizes fresh talent, fast-paced adaptability, and cultural fit. Many seasoned attorneys, paralegals, and legal professionals find themselves sidelined as firms seek younger, tech-savvy hires who, in their eyes, better match the industry’s evolving demands.

This discrimination isn’t always blatant. It can be subtle—like being overlooked for high-profile cases or finding that networking opportunities start to dry up. Sometimes, it appears in hiring decisions, where experienced candidates are told they are “overqualified.” Other times, it manifests in casual conversations where partners joke about keeping up with the times or suggest that a more senior attorney should consider retirement. Often, seasoned professionals find themselves passed over for promotions, dismissed as “too expensive,” or subtly encouraged to step aside for younger, supposedly more “dynamic” colleagues. While the bias may not always be overt, the impact is real. Understanding the warning signs is the first step in countering them.

Here are the key signs of age discrimination:

  1. Job Rejections Without Explanation – You have the credentials, the experience, and the track record, yet you keep getting passed over for younger candidates.
  2. Overemphasis on ‘Cultural Fit’ – Hiring managers stress the importance of a “young thinking and dynamic culture,” which may be code for preferring younger employees.
  3. Lack of Promotion Opportunities – Junior colleagues receive promotions, while you remain in the same role despite your experience and contributions.
  4. Pressure to Retire – You notice subtle (or not-so-subtle) hints about your retirement plans, as if your experience and contribution mean nothing and you are expected to step aside.

Conversely, you may also be showing signs that you are out-of-date because you:

  • Still use AOL, MSN, Earthlink, Hotmail, Yahoo
  • Are seen using a typewriter instead of a computer or writing in a 3-ring binder (really)
  • Are only marginally aware of social media
  • Don’t pay attention to much of the news, let alone what is happening in your specialty
  • Have no social media skills. (You don’t have to chat about your personal life. However, you do need to get with professional programs: LinkedIn, twitter, tweet, Instagram or whatever the latest trend is.) 
  1. You Further Draw Attention to Being Out-of-Date Because You Use These Expressions:
    • It’s so gay
    • Back in the day
    • When I was younger
    • Man up
    • Bless your heart
    • Having a senior moment
    • You people (which can be discriminatory in and of itself)
    • Real men/women don’t
    • That’s what the internet is for
    • Work smarter, not harder
    • Back in the/my day
    • Boys will be boys
    • You can’t handle the truth
    • You’re just young. You’ll learn
    • Don’t worry, be happy
    • Life isn’t fair
    • You’re too sensitive
    • Those were the good old days
    • That’s just the way things are
    • Get over it
    • Everything happens for a reason
    • Snap out of it!
    • Stewardess
    • Lousy
    • Classy
    • Slacks
    • Pocketbook
    • World Wide Web
    • Gal
    • Stoked
    • Beat feet
    • Pad
    • Bust a gut
    • Bummer
    • Hang loose
    • Heavy
    • Spilt
    • Out to lunch
    • Drag
    • Stoked
    • Veg out
    • Talk to the hand
    • Not!
    • Yada yada yada
    • Whatever
    • You go, girl!
    • Da bomb
    • My bad
    • Groovy

Recognizing these patterns is the first step toward addressing and overcoming them.

How to Avoid Becoming a Target of Age Discrimination

While you can’t always control the biases of others, you can control how you present yourself. By staying proactive and positioning yourself as an indispensable asset, you ensure that your experience is recognized as a strength rather than a liability. Here’s how:”

1. Stay current with technology

Legal employers expect attorneys and legal professionals to be proficient with modern legal research tools, AI-based contract review platforms, and case management software, billing and other tools.

Signs you are technologically out-of-date:

  1. Don’t be computer pathetic! Anything technologically related and your answer is, “I am much better on substantive issues.” No. Those substantive issues most likely involve some kind of technology. 
  2. Get with the latest trend such as AI. Don’t be one of those who are saying “Those young people will never know how to use a book, and do it the hard way. They have an easy way out.” Have you considered that maybe it’s no longer necessary to “do it the hard way”.  They may be able to write the codes. Can you?

Instead:   

  • Enroll in online courses focused on legal technology. There are plenty of free courses you can take along with continuing legal education. You can get on software websites such as Relativity (the most popular litigation support software at this writing) and take the tutorial for free. Missing out on one of the most popular platforms is certain to hinder a positive perception about you. 
  • Attend industry conferences to stay ahead of emerging trends. Legal Tech, ILTA and other conferences are specifically aimed at technology usage by the legal industry. 
  • Obtain certifications in relevant legal tech, such as eDiscovery and AI-powered case analysis.
  • Ask a colleague to train you or sit in on the onboarding classes. 
  • Have the firm dip into its professional development budget and spend a little money on you.

2. Refresh your resume and LinkedIn Profile

Your resume and LinkedIn profile should reflect impact, not just years of experience. Showcase your ability to adapt and lead in today’s legal landscape.

  • Eliminate outdated skills and highlight relevant expertise. I can’t imagine why listing faxing or WordPerfect as skills on your resume would be relevant in today’s job environment. It’s as bad as saying you know DOS. (Remember DOS?)
  • Focus on measurable results rather than decades of service. Instead of saying, “What do you mean? I have 20 years doing this!” You might say, “By using the Acme platform, I was able to get three million pages of old insurance policies produced in two weeks rather than relying on old software that would have taken six weeks.” 
  • Avoid listing jobs older than 15-20 years unless highly relevant. Going past 20 years, you might list those jobs under “Relevant Positions” without the dates.

3. Modernize your communication style

Language matters. Your ability to communicate effectively in today’s legal world will impact on how you are perceived.

  • Use current legal terminology and industry jargon fluently.
  • Speak with confidence about new legal trends and practices.
  • Don’t like working with a younger generation because you feel you know more than they do? Maybe not. Learn to be collaborative. Say things like, “I didn’t know that. Tell me about it.” 

4. Don’t interview like a “person of a certain age”. Stop:

  • Fumbling with technology like Zoom or Teams and specifically not taking off mute when you sign on.
    • Employers hate to see you try to get the sound on when the meeting starts. Get the sound on before you log in.
    • Practice with a friend or work colleague
  • Assuming experience makes you a shoo-in
  • Mentioning your age or personal life
  • Treating younger interviewers as immature
  • Bragging about understanding modern technology
  • Being too talkative  

Understand the fears of hiring a “mature worker”:

  1. Fear of hiring somebody with 30-40 years of experience: “they’re not going to be coachable.“
  2. Conquer those misunderstandings by using in your examples [at the interview] a time when you learned something from a colleague, especially a younger colleague.
  3. Talk about what “we” would be doing.

The best places for “older” workers to find employment or move up the ladder are smaller or mid-size firms or small in-house legal departments. Look for someone who wants you. These employment opportunities are better because there is less competition, they hire quicker. The chances of winning the fight against big firms is not as successful.

5. Network across generations

Building relationships with professionals of all ages demonstrates adaptability and relevance.

  • Engage with younger attorneys, legal professionals and paralegals to bridge generational gaps.
  • Join mentorship programs to share your expertise while also learning from younger colleagues.
  • Attend networking events that attract professionals from diverse career stages.

6. Know how to answer discriminatory questions such as:

  • “How do you feel about everyone here being younger than you?” (This is an actual question asked by a Managing Partner to a 56-year-old candidate, a known expert in her field.)
    • Answer: “If what you are asking is, “Do I have the energy for the job, the answer is yes.” You might acknowledge a red flag just went up.
    • If you are working with younger colleagues:
      • Don’t say you can teach them.
      • Don’t tell them how you did it “before”. 
      • Mention you have worked with someone younger and give an example. 
      • Put them at ease and don’t be condescending. 
      • Role play
  • How long before you retire?
    • Answer: “If what you are asking is, “Am I here for the long haul, the answer is “yes”. 

Always understand what is behind the question. You don’t have to answer illegal questions, but a red flag should go up and you need to make a decision as to whether this is the place for you. 

7. Recognize the bias’s before you get trapped. People sometimes think that “people of a certain age”:

  • Have no energy: You are all about low billable hours, too many doctors’ appointments and are a 9 to 5er. 
  • Are just at work until Medicare kicks in and the 401k vests.
  • Have gone as far as possible.
  • Have no further ambition or motivation. 
  • Are just coasting – here for the benefits. 
  • Lack motivation. You are just suiting up and showing up.Refuse all overtime.

8. Talk the talk. Project an image of energy.

  • People start to discuss their ailments at around the age of 50, thinking everyone else will relate. Do not discuss disabilities. It’s so easy to complain about your back, that your knees hurt, that parts are sagging…….
  • Be able to quote sources. 
  • Talk about:
    •   A continuing legal education webinar you took
    •   What you did over the weekend: swam, ran, 
        hiked, golfed, played tennis or pickleball, coached Little 
        League, went bowling
    •   A non-fiction or popular book you just read
    •   Your workout
    •    An activity showing how alive you are in the
         community
    •    Involvement with a legal association
    •    Speaking engagements and articles written
    •    A vacation where you ended up walking a trail for miles

9. Invest in Continuous Learning

  • Adaptability is key. The most successful legal professionals stay informed and continually update their skill sets.
  • Participate in Continuing Legal Education (CLE) courses in emerging practice areas. If your firm will not advance the funding, give up your Starbucks and pay for it yourself. It’s the right investment. Add those classes to your profile to show you still have direction and that there is constant movement, and you are not brain dead. 
  • Stay involved in industry organizations and legal forums.
  • Be open to feedback and demonstrate a willingness to adapt to evolving trends.
  • Teach or write. It’s the old: if you teach it, you must know it.

You are told you are “overqualified” which may be code for “you’re too old”. Smile and say:

  • “Actually, here’s the good thing, you get an employee who doesn’t have to be trained, who can step right in and do the job.”
  • “I get a job I have always wanted. It’s no longer about the title. It’s about having a job that fulfills you. That’s me.”      
  • “I want to work and continue. Money is secondary.”
  • “This is a tight candidate market. I can help.”
  • “I have always wanted to work for “Giggle, Wiggle and Sniggle because….”
  • “I will get more involvement. More/less travel. Access to the latest technology.”
  • “Yes! I do have experience! Hiring/promoting me is great for you because I understand what it takes to be successful.”

The Younger Worker: Ageism Cuts Both Ways
The youngest team members can be bearing the brunt of workplace ageism right now, potentially impacting their careers. Older workers have always had negative-leaning opinions about the young.

Here are some words about younger adults. They are positive, have ambition, intelligence and are tech-savvy. The negatives, true or not, are that they are entitled, coddled, disrespectful and radical. Working habits of millennials and Gen Z, and their inclination to prioritize work-life balance, may cause older workers to chafe. Let’s recall that Steve Jobs was twenty-one when he founded Apple. We often underestimate how much younger people have to contribute. Hopefully, more employers are realizing it.

  • Acknowledge that youth have many good points.
  • You learn easily. “Quick learner” is your middle name. 
  • Ask older employees for advice based on their experience.
  • Understand the ideal older employee. Don’t disqualify them because somehow you think that their intelligence and knowledge has been drained out of their brains as they age. While some do remain computer pathetic, most do not. Afterall, it was their generation that invented or improved upon computers. 
  • Do realize that appearances matter. 
  • Get yourself out there. Volunteer for roles that convey seniority and leadership.
  • Do not overcompensate as you are what you are, and there is nothing wrong with that. There is also nothing wrong with practicing to be a little more assertive, but don’t try to portray a person that you aren’t (and don’t want to be).

Facing the Harsh Realities: The Legal Job Market Is Competitive

The statistics don’t lie:

  • 74% of job candidates over 40 report experiencing age-related challenges.
  • It can take 75-100 resumes to land a single interview, even in a tight candidate market.
  • On average, candidates must go through 5-10 interviews at different firms before receiving an offer.
  • Don’t blame age discrimination if you are tracking the norm. 

This means that even the most experienced legal professionals must actively work to remain competitive in today’s market.

Are you discouraged and want to sue? That’s not always the best strategy. It’s hard to prove. Talk with a lawyer, if you feel you have a case. Instead, consider using strong strategies. Anger and depression equal a waste of time. You do not have the power to change the market.

Why Your Job Search or Promotion Efforts May Be Failing

If you’re struggling to land a new role or move up the ranks? Take an honest look at these common missteps:

  1. Your Cover Letter Is Outdated or Generic – Using an uninspired, formulaic template will not get you noticed.
  2. Your Resume Is a History Lesson Instead of a Selling Point – Cut excessive details and focus on your most impactful contributions. I frequently see resumes going back to 1986. Understand that’s 40 years ago and its relevancy is long gone. 
  3. You’re Over-Reliant on Online Applications – Networking remains the most effective way to land new opportunities. Look at it this way: your colleagues know before HR that someone in the firm may be leaving, and that role is going to need to be filled. It may as well be you. 

Not advancing in your current role? Consider these reasons:

  1. You Haven’t Evolved – Doing the same job year after year without visible upward movement signals stagnation.
  2. Your Appearance Feels Outdated – While unfair, first impressions matter. Stop looking like your grandmother but at the same time, don’t try to be overly hip. Pay attention to details as seemingly innocuous as what style glasses you are wearing. 
  3. You Haven’t Invested in Professional Development – Staying relevant is non-negotiable.  Sure, you know all about personal injury. But are you aware of the new legislation passed two years ago? Are you operating on outdated premises?

People with high profiles rarely get turned away. You are too valuable and all law firms like employees with “stars on their doors”. On the other hand, you may hear that you are “overqualified”. Maybe you are, however, “overqualified” may be a code word for “old”. Employers may feel that you are going to demand a larger salary and have one foot out the door. They also may mistakenly believe something must be wrong if you are taking less. Note that another possible disqualifier is the word “seasoned”.

Position Yourself as a Leader.

Whether you are seeking a new job or seeking to move up in a law firm, age discrimination can rear its ugly head.  That’s when we tend to become over-zealous in our pitch. Rethink your presentation!

Here’s the flip side of the age-discrimination challenge: if you know what business pain you solve and can talk to hiring managers or partners about that pain, they can’t afford to care how old you are. When you stop talking about your skills and abilities — and offer up whining, please-like-me attributes that no manager can possibly evaluate, you are talking out of context and fading into the crowd like every other face. You can talk about something far more important. 

That important something is the business pain – the excruciating and expensive business problem that justifies the new person or position in the first place. If there’s no pain, there’s no new hire, no move up the ladder.

Just like a salesperson, you need to develop a Pain Hypothesis for your hiring manager or supervising legal professional.  If you answer questions in sheep-like fashion, trying hard to please, you are going to fail. Or, if you are seeking to carve a new position in your firm’s present structure, you will be rejected. 

This isn’t about your needs. It’s about what needs you can fill missing within the firm.  Look to fill the gap. It’s in the comparison process where topics like age can hurt you. “We could hire Philip, who could do this job in his sleep,” the manager might say, “Or Sarah, who’s going to grow into it but who could be here for years to come.” You don’t want to be in that police lineup, and the way out of it is to use your time to probe for business pain.

Get your manager talking about what’s really going on behind the scenes. You’ll find that the quality of the conversation shifts dramatically.  Here’s the perfect opportunity to allow your experience and recent continuing legal education work for you.

Suddenly, you’re a trusted advisor, a consultant digging to learn more about what’s not working.  Ask questions about the processes, the obstacles in a manager’s way and the thorny problems they’ve seen before in similar situations. This will vault you to a higher level of conversation, one that is much more valuable and memorable. Pain interviewing isn’t a cure for age discrimination, but it’ll give you a focus and an edge that will make discrimination a non-factor in your quest to improve your career.

The legal profession values intelligence, adaptability, and leadership—traits that only grow stronger with experience. By staying relevant, engaged, and proactive, you can make age discrimination a non-factor in your career. Remember: it’s not about how many years you’ve worked; it’s about how much value you continue to bring to the table.

About the Author

Chere Estrin has over 20 years of experience in the staffing arena, including executive positions in law firms, litigation support companies, and the legal staffing divisions of a $5billion publicly held corporation. She is CEO of Estrin Legal Staffing, a nationwide staffing organization. Ms. Estrin was founder of the Paralegal Knowledge Institute, an online CLE organization. She publishes the prestigious digital magazine, KNOW, the Magazine for Paralegals, and is the former Editor-in-Chief of Sue, the Magazine for Women Litigators. She is also the author of 10 books about legal careers for attorneys and legal professionals.

Ms. Estrin’s contributions to the legal industry have been significant, and she continues to play an active role in shaping the future of legal staffing and training. She writes the popular,

award-winning blog, The Estrin Report, and has been interviewed by CBS News along with many top publications, such as The Wall Street Journal, Fortune Magazine, Forbes.com, Los Angeles Times, Entrepreneur Magazine, Newsweek, The Chicago Tribune, The Daily Journal, ABA Journal, Above the Law, ALM, Law360 and many others. She has also been a speaker for many prestigious organizations and written hundreds of articles.

As the Co-Founding Member and President of the Organization of Legal Professionals (OLP), Ms. Estrin has guided the association’s development and implementation of the eDiscovery and Litigation Support certification exams (first in the country) along with Pearson Publications, a $7 billion corporation specializing in certification exams and educational publishing. She was also the Education Director designing, creating and executing online, live training programs with an on-call roster of over 500 instructors throughout the world. Currently, she provides webinars on legal career matters for LawPractice and Lawline, two of the largest attorney CLE online training organizations.
Ms. Estrin is a co-founding member of the International Practice Management Association (IPMA) and the Organization of Legal Professionals, composed of a prestigious Board of Governors inclusive of judges, an ABA President, and well-known attorneys. She is the recipient of the Los Angeles/Century City “Women of Achievement” award and recognized as One of the Top 50 Women in Los Angeles. Ms. Estrin has been writing The Estrin Report since 2005 and most recently launched her podcast, “Lawfully Employed”.

Reach out at: chere@estrinlegalstaffing.com or visit her website at EstrinLegalStaffing.com.