Law Practice

Two Truths and a Belief Part 3 - Truth #1

Truth: Most of the work “demands” that I received were actually “requests.”

Many days my job as an associate felt like a marathon session of task “whack-a-mole.” Picture me, perching before my keyboard, intent on my computer screen, batting down each rapid-fire email request that came my way. “This needs to go out immediately!” “Please turn the next draft.” “Please explain your comment to Section 8.6(b) of y-document.” “We need to jump on an all-hands call for this matter to review z-document. I’m only available in the next hour - please coordinate and run the call.” Every request felt urgent, and I registered every request as a “demand.” By this, I mean that while I retained some powers of prioritization, I basically believed that each “demand” must be complied with precisely as the demander communicated it - I had no wiggle room in form, substance or timeline, and I certainly didn’t have the option to decline. Herein lies the key distinction between a demand and a request. There are multiple possible responses to a request (accept, reject, propose an alternative), but a demand is inflexible.

My mindset about work requests left me feeling totally at the mercy of my email inbox (and the phone, and the partners, etc. etc. ad infinitum). Work requests became the tyrannical ruler of my life and I lived in fear of the next “demand” that I would somehow have to figure out a way to accommodate. No joke - my stomach would drop to my feet and my heart would race every time I saw a new email in my inbox that I wasn’t expecting or that came at an odd hour. I lived with the sense that no matter where I was or what I was doing, a work request could always come along and derail it simply by arriving at a particular time. I’ve had clients tell me they also live with this sense, and that it feels “suffocating.”

This mindset also clearly has limits. What happens when the requests are coming in too fast to be dealt with and are piling up in your inbox? Or the requests are in conflict with each other? Or the requests are completely outside of your realm of knowledge or current capacity? Or the request comes at 7pm when you’re putting you kid to bed, at 9pm when you’re enjoying a moment with your spouse, at 11pm when you’re laying down to sleep, at 1am when you wake up to pee, or on your vacation? If all of these requests are “demands,” then you have only one choice, to comply precisely as asked, even if that’s actually bad for the work product, a client, or your mental and physical health.

Working with requests is a fairly common theme in coaching engagements - requests are tricky. But, there are some contextual factors specific to law firms and lawyers that are fertile ground for the particular kind of confusion that I struggled with.

First, lawyers are generally perfectionistic and risk averse. If there is the chance that one in five requests is actually a demand, it is more in keeping with our habits to invent a “legal fiction” and chose to operate as if all requests are actually demands. We take the least risky path (often without a real understanding of the scope of the risk) because we’re always “thinking like a lawyer” and “issue spotting” (i.e. worrying). Then we label it a “best practice” and drill it into associates skulls.

Second, we operate in an professional services context where there is an inherent imbalance of power between the client and the attorney. The client gets what the client wants. Many lawyers also espouse the belief that they simply cannot negotiate with their client’s requests if they want to keep the business. And, as an aside, many associates believe that the quickest way to stop getting good work is to say “no” to a request (any request).

Third, firm lawyers are stressed, over-committed, and under-resourced. They are also not trained to be managers. And, most of the work requests a young lawyer receives are from other lawyers. So, something as simple as framing a request for delivery of work product with enough buffer-time for review and revision often comes out like “I need this ASAP!!” A bit dramatic, no?

And fourth, to this amply-stocked tinder box we add the accelerant of our ethical obligation as lawyers (which I’m in no way criticizing) to zealously represent our clients. And there you have it. Look, Ma! Proof that I must immolate myself upon the pyre of my professional obligations!

Clearly the way I operated, treating each request as a inviolable demand, was reasonable under the circumstances. Ultimately, though, I bumped up against the limits of it’s utility and I had to make a change. Things would fall through the cracks. I’d become entirely overcommitted and then underdeliver. I’d spend evenings doing nothing but sitting in front of the TV and refreshing my email inbox because I was afraid to be too far away from a computer. And I was totally sick of living in fear.

So, I experimented with a new strategy. I hypothesized that most of the asks were true requests and that I had options about how to respond to them. At first my strategy took longer - I had to actually assess my workload, understand the scope of the request, and get clarification from the requester around the nature of any related deadlines and work product. Then I would respond. Sometimes, I would propose an alternative from the initial ask. Sometimes, I simply accepted. And sometimes it was the best response to decline. Soon, this became automatic. Nine times out of ten it was quickly apparent that I was, in fact, dealing with a true request. And, in the tenth instance, a true demand became more immediately obvious.

Under my new strategy, I continued to be “responsive” to work requests in a conscientious way. And I continued to meet deadlines. But I made a shift in my process. Would it serve you to be conscious of your own process for handling work requests? What is your automatic response? And why? Is it appropriate? Always? If not, when and why not?

If you feel like you’re in an un-winnable war with your inbox and want to talk about about coaching on responding to requests, please go to the Schedule a Call page to schedule your call online. Or you can reach me at

What's Next: A Fork in the Road

This weekend, I ran into a law school friend who I’ve not seen for awhile in the grocery store. It was one of those sweet moments where I witnessed my old friend as if in a double-exposed polaroid, simultaneously fully inhabiting his current moment - standing in the checkout line with his wife and infant son - and yet somehow still standing for the memory of all those prior shared experiences - 1L year, exam cramming, and study-abroad summers.  

“Hey! Jen! Congratulations! I’ve been meaning to reach out and talk about your career move!  So…what exactly are you doing?”  We hugged, and as I greeted his little boy and reintroduced myself to his wife, I realized that the moment was more than just a nice coincidental meeting - it was instructive.  There’s a story to tell to all of you out there.  And it’s time to tell it.

Three years ago, I was three years into my career as a lawyer and I was coming apart at the seams.  You might not have known it to look at me, but I was.  I was working with a wonderful group of humans (who happened to be lawyers) in a very small office of a national firm that specialized in finance and danced opposite the Biglaw players on major deals.  I had just clocked my busiest year yet in a roller-coaster practice area that tended to rise and fall with the markets.  I was getting excellent experience, running deals as a third year associate that many senior associates would kill for, and there wasn’t a single “ogre” in group.  So why, then, did I feel like a desperate caged animal?  

Some of you reading this who are attorneys may just intuitively “know” the answer to that question, even if you don’t know my particular circumstances.  Law firm life is really hard.  And I am by no means the first, second, or third person to say so.  In my efforts to be the “perfect associate,” as measured by work-quality, relentless issue spotting, responsiveness, and productivity (read, hours billed), I’d backed into a way of living and working that was slowly choking me to death.  I do not mean to suggest that one cannot be a “good associate” and, you know, survive to old age.  Just the opposite really.  But, unfortunately for me, I didn’t then know how to do that.  Why?  Well, that’s another blog post entirely, but I’ll say this: Because, early in my career, no one taught me or showed me what that would look like.

Now, I also don’t mean to suggest that I, Jen Overall, am in possession of the single, magical piece of knowledge that can transform a nightmarish work situation into a generative, life-giving one.  I am not.  But, I will tell you that with some time, focused attention, and excellent outside support from my therapist/coach, I learned a new way.  And, as a result, my lot as a lawyer improved.  I didn’t change the profession as a whole, but I learned to navigate it more effectively and healthfully.  

This change also created the mental space (which honestly, felt miraculous in and of itself) for me to reconnect with what really mattered to me. My favorite aspects of practicing law have always been 1) the never-ending learning, and 2) the never-ending teaching.  Really, at a basic level, this polarity forms the “what” of the job description of an attorney.  Learning/teaching is what we do as counselors for our clients and what we do as employees and leaders within a firm.  In my daily practice, I found that I could take or leave the actual subject of this learning/teaching (i.e. the law…please don’t tell my law professors, it’s not their fault), but the process - now that lit me up.  So, it’s perhaps not surprising that once I caught wind of a profession where learning is both the subject and the object of the job, I was hooked.  In pursuing a coaching certification, I dived deeply into the “how” and they “why” of adult learning and development, into the evidence-based techniques that can support transformational growth and learning in service of both meaningful real-world goals (making partner, finding “whole-life” balance, learning to delegate, learning to lead an effective team, or building a book of business) and profounds shift toward generative ways of living and working and increased mental complexity. 

So, here I am.  The rest of this story is as yet unwritten.  I’m accepting clients, some of whom I expect will be standing precisely where I stood three years ago and looking for the outside support that a coach can offer.  I’m also designing a course for on-ramping first-year associates to teach what I wish someone had taught/showed me at the outset: how to crush a legal career without (accidentally) crushing your soul. I am also joining, through my writing, my research, and my daily work as coach and consultant, the growing chorus of voices calling for creative and systemic changes in the legal profession that support growth and profitability alongside improved well-being of attorneys and staff, meaningful growth in diversity and inclusion, and reclamation of the professions’ innate duty to embody ethical leadership.  

I’m thrilled to share all of this with you. Let’s roll.