In my twenty plus years in law, I have hired more than a hundred attorneys as both the managing partner of a large law firm and now, as a founder of a boutique office.  Hiring isn’t one of those things we learn in law school, and most of us have no choice but to get better through trial and error.  And wow has COVID made things harder.

I have certainly made my fair share of hiring mistakes, but I have also found some of the greatest lawyers, partners, and friends who have made my professional and personal life better.  Here are the seven things I wish I knew earlier about hiring associates.  In addition, I have created this CHECKLIST to pass along the dos and don’ts I have learned and the practical considerations we often overlook when we hire.

1. What Are You Looking For?

This may look so obvious as to be silly — but stick with me for a minute.  Failing to give long-term thought to who and what you are looking for is by far the principal mistake in hiring associates (or even a lateral partner).  Are you looking for a “worker bee” to immediately jump in because you have an overflow of work, or are you looking for an originator who can someday help you support the practice and generate work?  

More often than not, we as lawyers tend to be reactionary in our hiring.  When faced with a crushing workload, I have a partner who routinely says “I need a warm body” to help me get all this work done.  However, reactionary hiring because of short-term circumstances isn’t going to advance your firm in the long run.

Instead, you need to ask yourself:  “What do I need over a one, three, and five-year horizon?”  Ask yourself, what is your highest and best value in the business of law?  Ask yourself, what is our business model and how would a new associate advance that model?  Should you be spending more time in court and with clients?  Or should you be spending more time on marketing your practice?  Regardless of your answer, you should begin by hiring someone who can relieve you of the stuff you shouldn’t be doing.  What characteristics do you need?  Not all people are the same.  Do you need someone with a court presence or somebody who prefers to write at their desk or work remotely?  Do you need someone with the skills to meet with and put clients at ease?  Do you need someone who can put in grueling hours for a year or two?  Do you need someone that will be able to generate some of their own work in a year or two?  

What does this person look like?  Some lawyers are better in court, some prefer to write in the background, and some excel when they are in the community generating new work.  Generally, I am looking for someone who is eager to be my student.  To learn the way I write, to learn the way I tell a narrative, and who is willing to learn and evolve.  Regardless of your answer, the hiring strategy, process and timeline of hiring will be different based upon your individual needs.  In hiring there truly is no one size fits all method.

2. Experienced Versus Newbie.

Without a doubt, every lawyer with a busy client base has said these words: “Wow, could I use an associate with three to five years of experience!”  But, this is the most common hire that fails.  We mistakenly believe that there is a one size fits all for mid-level associates – as if they have interchangeable skill sets, the ability to work in any office environment or in the new remote world, and who don’t come with the baggage of being trained with someone else’s bad habits.  Unfortunately, this is not reality.

The real question is whether it is easier to find someone in the marketplace who has exactly the skills you need, or whether it is better to spend the time and money to train them to be exactly the lawyer you need.  My experience is that associates you hire when they are young, train from scratch, and build into the lawyers you need are much more likely to stay with you and your firm for the long term.  They are more likely to become your partners; they are more likely to advance the same business goals, and they are more likely to adopt and advance the values and culture you have built your firm on.  And perhaps the most overlooked benefit is that they don’t come with the burden of having to break someone else’s poor training and bad habits.  

Undoubtedly, there is a trade-off in that “newbies” are less productive and can take months (and likely more than a year) to become economically viable.  And at the outset, this may feel like two steps forward and a step and a half back. Often they can’t, and won’t, provide the immediate relief you are looking for, but will pay off in the long term.

Alternatively, you may want to explore more flexible arrangements.  I have found the lifestyle that accompanies the full-time practice of law is inconsistent with the needs of many of the most talented and experienced lawyers. According to the ABA, there are literally hundreds of thousands of lawyers who have left the practice of law because of the desire to raise children or take care of family members.  These attorneys have different goals and needs.  And if you are open to accompanying their desire to work part-time or remotely, you can really expand the pool of potential applicants.

3. The Interview.

In my experience, the interview should be 70% learning about the candidate and 30% pitching your firm as the place to work.  While there is an oversupply of attorneys in general, skilled associates with the experience you are looking for will probably be difficult to find, and the good ones have multiple choices.  Thus, I have seen time and again (and made this mistake myself) where the interview becomes a pitch in trying to sell the associate on your firm.  Usually, this strategy ends badly as the interview loses its primary purpose, which was to learn about and test the candidate.  

You are going to spend more time with your associates than you are with your family; you are going to pay them hundreds of thousands of dollars over the coming years; and picking the right candidate is of critical importance.  Test them on their skills.  Don’t be afraid to give them hypotheticals on real-world legal questions.  How they approach your question, and how they communicate their response is often more important than whether they know the answer off the top of their head.  Was their analysis well thought out?  Was it superficial?  Was it designed to give you the answer you wanted instead of the answer you needed?  

Don’t go into an interview without knowing the questions you are going to ask.  Of course, you want to keep it conversational, but at the end of the day there is a baseline of critical information that is necessary to make an informed decision on a hire.  Ask them about their achievements.  Find out what motivates them.  Figure out whether they are a natural optimist or pessimist.  And write down their answers – but don’t write down your opinions or notes during the interview.  That process will come later when you make a holistic analysis of the candidate.

4. Set Job Expectations In The Interview.

It took me a decade of hiring to figure this one out.  In my earliest hiring interviews, I disproportionately focused on the best qualities of my firm and our practice.  I told candidates about the great people, I told them about our lives, our successful wins, and how great it is to be a practicing lawyer.  But that’s not all there is to the practice and business of law.  There is also the grind, the late nights, the hard work, the feeling of pushing a rock uphill.  More than once I have hired associates who came in late and left early because they concluded my firm was the right “lifestyle firm” for their needs (something I wasn’t trying to encourage).  If you need your young associate to be the first in the office and the last to go home, you need to directly convey this in the interview.  Tell candidates the hours you expect them to work on a monthly basis, discuss whether that is consistent with the lifestyle and career they are looking for.  Tell them whether your work style requires them to be in the office or if they can work remotely.  Figure out what drives each candidate: Is it money?  Is it time with family?  Is it flexibility in their work schedule?  Is it social recognition?  Or is it that they want to be your partner someday?  These are questions that need to be answered in an interview and not something to work out after they begin.  Hiring can’t be aspirational.

5. Don’t Forget About The Conflicts.

Failing to deal with conflicts has bitten me a couple of times over the years.  While it might not be something to deal with in the first interview, before you extend an offer, you need to figure out whether your candidate can work on your cases.  We tend to hire from the pool that we are most familiar with, and that means there tends to be overlap in our cases – whether we know it or not.  Hiring an associate who cannot work on your caseload either because of their direct conflicts or because of their imputed conflicts (the hidden danger) can be devastating to your productivity and your bottom line.  Here, there is no one size fits all answer, but you need to ask at least the files the candidate is currently working on.  I suggest that prior to making a formal offer, you tell the candidate you intend to make an offer but need to clear conflicts first.  Ask them for a written list of clients they are currently working for.  And you should be prepared to send the candidate a list of your current clients.  With a more experienced attorney or partner you will want to dig deeper.  While sometimes a sensitive issue, you probably want to find out who their current firm’s top 10 clients are and what cases they have been working on.  Depending upon your practice, you may want to go back two or three years to ensure you avoid conflict issues.  However, you develop your strategy, the key is to make sure a hidden conflict doesn’t undermine the very goals you had when you set out to expand your firm.

6.  Fail Quickly – Sometimes You Are Going to Get It Wrong.

Regardless of how thorough your interview and hiring process, sometimes you are just going to get it wrong.  And in those moments, fail quickly.  Don’t try to force it.  Hiring is in many ways like a relationship, you know when it works, and you know when it doesn’t.  When you try to keep an employee out of some sense of loyalty or guilt, you aren’t doing yourself or your business any favors.  And you are definitely not doing the associate any favors!  While I have hired more than a hundred attorneys, I’ve been forced to fire nearly half of them.  And I can say, with one hundred percent confidence, if they aren’t working out for you – you aren’t working out for them.  Never has an attorney I’ve fired failed to find a place more conducive to their personality and skill set.  Firing a lawyer does not mean you make them and their family homeless.  Quite to the contrary, in the long run, people find the right job and the right place to work.  In my twenty-plus years, I have never looked back and said, “I shouldn’t have fired that person so quickly,” but I certainly have suffered the consequences of not terminating an employee who didn’t fit sooner.

7.  Finally, Trust Your Instincts!

Hiring is like great art ─ you know it when you see it.  Finding the right associate is much more than finding great qualifications on their resume.  It’s about a cultural fit; it’s about shared goals; it’s about being able to make a human connection; it’s about finding someone you feel comfortable trusting with your most valuable business asset – your clients.  If your instincts are telling you that something isn’t right, that’s a good sign the fit is wrong.  If you are second-guessing yourself even before you make the job offer, it is definitely the wrong fit.  In a dozen or more instances I have “stretched” to convince myself that the candidate was right.  Often it is because they looked great on paper or I needed immediate help, but in every instance I stretched, it turned out to be the wrong person.  The nuances of finding the right employee are often difficult to identify, but you know it and feel it when it’s wrong.


Expanding your practice and your firm can improve both your quality of life and your profit margins, but it can also have the opposite effect.  The difficulty in finding (and keeping) the right associates in an ever-changing marketplace is becoming more difficult.  Associates are less loyal and the cost of employees is on a constant march uphill.  But when you do find the right candidates to bring into your firm – it can be transformative to your practice.  

And don’t forget to download my CHECKLIST, which is a practical guide built upon two decades of learning what works…and what doesn’t. 

Greg Garman , Co-Founder Lawclerk

Greg Garman , Co-Founder Lawclerk


Related Posts…