Advice to My Young Associate Self

By Ivy B. Grey

I can vividly remember what my young associate days were like. As part of the class of 2008, I graduated with classmates who had offers rescinded or who were furloughed as the economy tanked. Good grades were no longer enough, an offer was not a guarantee of a job, there was no longer time to ramp up in an apprenticeship format, and our mountains of debt made failure not an option.

I wish I’d realized earlier that getting my job in BigLaw was not the end goal—it was just the beginning of an arduous journey that only a few can survive. While I still wince at some of the mistakes that I made then, I have enough hindsight to learn from them. And now, as a legal tech entrepreneur, I can see how much easier I could have made things for myself. Here are six tips to make sure you don’t have to learn things the hard way.

Trust is hard to earn, but easy to lose.

Trust is what earns you the opportunity to keep working and proving yourself. Nothing builds trust better than consistently producing correct, high-quality, timely work product. In particular, assigning attorneys are carefully reviewing your written work. Your worries about showing that you can provide stellar legal analysis will make you forget that you need to be meticulous in presenting your work. Yes, those nitpicky typos really do matter. And, no, your analysis is not so nuanced and brilliant that you can skip proofreading! Your analytical skills are expected to be in their infancy, but you will be expected to demonstrate diligence immediately.

Beware that a reputation for sloppiness is nearly insurmountable. Unclear writing, abundant typos, and incorrect citations will cause other attorneys to think that you are careless. Even one sloppy project can destroy that trust—and you may not get a second chance. Avoid this by accepting the premise that details are important and you are susceptible to error. Use tools like jEugene and American Legal Style for PerfectIt to ensure that your writing is error-free. These programs are inexpensive so you can afford to buy them for yourself. Your reputation is worth it.

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Mistake response defines you.

The question is not whether you make a mistake, it’s when. How you act in response to your mistakes will determine if you get another chance. Accepting responsibility for your mistakes shows humility, that you take ownership over your work, and that you can learn from your mistakes. So reflect on how the error occurred and how it can be prevented in the future. Seek out training at your firm or local bar association so that you can have a better understanding of the practice or procedure. Make checklists so that you can become systematic about checking for details that are easy to miss.

Commit to learning your firm’s technology that can help avoid these mistakes. For example, your firm probably has a case management system that helps with client deadlines. Use this system along with your own personal calendar to stay on top of deadlines and prompt you to start projects with enough to time to complete them (even with interruptions). Humbly showing that you have learned from your mistakes—and that they will not be repeated—shows that you are a trainable team player. Digging in your heels and blaming others marks you as difficult and untrustworthy.

Check for blind spots. You don’t know what you don’t know.

Blind spots are biggest when you first begin to practice law. As you gain experience, you will develop judgment and gain a better sense of where the blind spots might be. Until then, keep in mind that you don’t know what you don’t know. There are points of law that you will not know are relevant and there are items on checklists that you will not know exist. You can begin to uncover your blind spots through mentoring, actively reading bar publications, listening to podcasts, and participating in your local bar association. I found this problem most striking with research. With research we can simultaneously feel like we know everything and also feel like we know nothing. It’s easy to follow a trail that makes you feel like you’ve mastered the subject but turns out to be irrelevant, while missing the most important and relevant case.

Legal research tools like CARA can help you check your research after you think that you are done to make sure that you’ve addressed the relevant law. The research librarian can also help you to build a better understanding of your topic before you get started. You may also have a seasoned legal assistant who has a wealth of knowledge. So swallow your pride and have your assistant review your work. Listen to their advice and their explanations for why they check what they do and the way that the firm does things.

More does not mean better.

A longer, more complex brief, memo, or contract is not necessarily a better one. Needless language or complexity provides more room for error. This is contrary to what we learned from law school! It’s a challenge to switch from minimum page requirements to page limits. But the more that you understand something, the shorter the document that you will use to describe it and the simpler terms you will be able to use. This ultimately serves your clients better because they will understand the matter better, too.

Keep it simple, keep it concise. Read Ken Adams on contracts and use WordRake to cut out superfluous language. If possible, leave time to edit the next day when it will be fresh in your mind and easier to cut unnecessary text.

Looking busy doesn’t help.

Endlessly toiling over an assignment may look like an answer, but it isn’t. Spending 12 hours to find a solution that you could have reached in two hours does not make you a hero. It makes you slow and demonstrates lack of judgment.

Try setting a timer for half of the time that your assignment should take. When the time is up, assess where you are and whether you’ve gone off on a tangent. Use the remaining time to get back on track. If you have discovered that this is indeed a bigger assignment than anticipated, discuss it with the assigning attorney. The assigning attorney may help you focus so that you can meet the deadline. And if the project truly is larger than anticipated, they will appreciate the ability to make adjustments before the assignment is already late.

Start from scratch, but don’t go it alone.

Don’t fall into the trap of relying too heavily on precedent documents. While it is not necessary to re-invent the wheel, be aware that precedent documents may lead you astray. Precedent documents can obscure the fact that you do not understand the assignment or your client’s goals. Start by outlining your assignment on your own. Do not underestimate your ability to determine the necessary elements. For example, if you are selling a tract of land, then you know that you need to describe the property, who is buying, who is selling, for how much, and when. Then list all of the risks and concerns that you learned about when you received the assignment. Now you can look for precedent documents that closely match your project. You can also search for provisions to insert that meet your client’s needs. If there are items in the precedent documents that you did not choose to include, then you can analyze the purpose that they serve and get advice about including them.

By starting the project on your own, you develop judgment in your practice area and you force yourself to understand all of the pieces of the puzzle. Blindly copying and pasting can introduce errors and shows that you are not committed to learning. That said, use your mentors and your document bank! This is not the time to go it alone and create new documents entirely on your own. The goal is to think critically and work efficiently.


The challenges my class faced in 2008 were unprecedented at the time. However, many things for young attorneys have become even harder. It’s now expected that great swathes of young attorneys will simply leave after two years because they are burned out, there is a crushing amount of work (or lack thereof), or they made rookie mistakes that led to bad reputations. However, just as the challenges have become harder, legal technology is making things easier for attorneys that seek it. No one likes learning new systems, but every technology I’ve mentioned above is designed to be easy to learn and have you up and running within 10 minutes. And because many legal tech tools are inexpensive, you can afford to invest in them on your own. So even if your firm is slow to adopt the latest apps, you don’t have to be. Be humble, listen to what’s going on around you, understand that the firm has systems for a reason and that they’re often more useful than you realize. Then use legal technology to use your time more effectively, impress your seniors, and get ahead!

Ivy B. Grey is the author of American Legal Style for PerfectIt, which is a proofreading and editing program for lawyers that runs inside of MS Word. It adds polish, reduces frustration, and saves non-billable time. Ms. Grey is also a Senior Attorney at Griffin Hamersky LLP. She's been named as a Rising Star in the New York Metro Area for four consecutive years, and her significant representations include In re AMR Corp. (American Airlines), In re Dewey & LeBoeuf LLP, In re Eastman Kodak Company, and In re Filmed Entertainment Inc. (Columbia House).

This article was originally published in Law Technology Today on April 26, 2017.

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