Gina came to the legal world at about the same age as my current assistant, in her early 20s. My then-wife, who worked with Gina in a busy real estate office, sent her my way after my assistant abruptly decided working in law was dampening her muse and moved to the country to return to her painting. When I asked her why she would urge me to poach talent from her office, she remarked, “Gina is young, quiet, somewhat shy, but talented. I am concerned, however, her confidence is being crushed by our office administrator’s management style.”
We gave it a go. Whatever shyness Gina had shrank as she responded to my snark. I took her with me when I joined a mid-sized firm a couple years later. She turned out to be so amazing that a mere three years later, she was in charge of evaluating new technology changes and onboarding all new legal assistants, paralegals, etc.
Leaving a firm I had been with for over a dozen years meant a lot of changes. New software. New processes. A new state and all that comes with it (e.g., figuring out where to shop, best routes to frequently visited places, recreating a social network). While I would have taken her in a minute, and she had previously moved with me once, the right move for Gina was to stay put. That added the need to train a new assistant to the list, upping the ante.
These edits took a lot longer than they did on “Gina time.” I was OK with that, although my client was pressing for a final by lunch. When I received the edits back, it became immediately clear to me (a) how horrible my penmanship must be, (b) how incomprehensible my editing style is to a novice, and (c) how I needed to figure out quickly how to “break it down” so that we could function as a team.
I made a second round of edits, taking care to write legibly. I typed a couple of new paragraphs from a different document I was reviewing that made sense to include while my assistant was inputting the first round of edits. My edits to what was by then a 4-page letter would have taken Gina 10–15 minutes to make. Moreover, she’d likely come back saying she had changed two other things because my edits were not as precise as what she knew would go out in a final.
I handed the document to my new assistant. I set my watch for 30 minutes as a reminder that it would be unrealistic to expect the edits in 10–15 minutes. I waited, perhaps not as patiently as was healthy, and was feeling stressed. About 45 minutes later, I went to get coffee, which took me past my assistant’s desk. She volunteered that she was “about done,” but her body language showed a high level of agitation. I took the risk of asking if she was able to decipher my edits and comments. Her face showed immediate relief, and she asked me a couple of questions. I explained some of my hieroglyphics that I took for granted, and I offered a couple of law-related Word tricks that I’ve implemented over the years.
I saw a final version of the letter, signed it, and got it out, perhaps 30 minutes later than the goal time. When I checked in with the client at the end of the day, he was more sanguine. He acknowledged he was pressing me because he felt stress from his clients to provide an answer. After that, I checked back with my assistant. This smart and delightful Gen Zer was visibly less stressed, so I asked for her honest feedback on the exercise.
She shared, “I was nervous, and that’s on me. I expect a lot from myself, and that sometimes means I put too much pressure on myself.” She added that she had not seen someone edit the way I did (essentially on the keyboard and ignoring the mouse), so that caused her to get down on herself. She did not say—mercifully—that the fact that “an old guy” was faster on the computer than someone who has been using one since first grade added insult to any injury.
I shared that I missed an opportunity to manage client expectations in a more proactive manner and that my “rust” from working with the same person for a dozen years resulted in assuming my assistant could read my mind in the manner to which I had become accustomed. I added that I probably transferred my desire to beat my client’s expectations to nonverbal pressure on her, and if that was the case, I needed to do better. We closed by talking about the need for self-compassion. Given she had just updated the index to my archive of this column, that seemed to resonate.
In the legal profession, of course, our clients often look to us to be sources of certainty and strength. They like when we convey an impression of invulnerability. I shared how I was feeling like a failure because I was behind on my deadline for this column, felt devoid of topics, and was wondering, “Is this a sign that I should hang it up?”
A “younger me” would not have displayed this vulnerability, particularly to someone 30-plus years my junior. But who knows, maybe this old dog is capable of learning a new trick.