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Sybil Procedure: Millennials and boomers are stronger together

Sybil Dunlop//July 19, 2019//

Sybil Procedure: Millennials and boomers are stronger together

Sybil Dunlop//July 19, 2019//

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Sybil Dunlop
Sybil Dunlop

There are tons of articles about working with millennials these days.  Authors have no qualms insulting millennials in the process. They are selfish. Special snowflakes. Entitled. And want to have it all.

But every generation has characteristics. And in this article I wanted to focus on another generation. What is it like to work with those nearing the end of their careers?  Aging boomers. These folks were born between 1946 and 1964. The oldest of the 79 million baby boomers reached age 65 in 2011 and the youngest will get there by 2029. They run our law firms. They are our clients. And they can be difficult to work with.

I’ll start with a disclaimer. Complaining about generational traits is akin to believing horoscopes. These traits can’t possibly define everyone born in the years following World War II, just as every August baby is not an attention-seeking Leo. Moreover, age discrimination is real. The Implicit Association Test reveals that most Americans have a harder time associating positive words with older faces than younger faces.

But having issued my disclaimers, I’ll plunge in and identify a few traits that appear more common among senior attorneys than junior attorneys.

Senior attorneys aren’t always the most woke. Most senior lawyers with whom I work want to treat people fairly. But growing up in a different era means that they aren’t always aware of the ways in which we create workplace cultures that can be exclusive. We can’t refer to our African American associate as “articulate.”1 We can’t talk to our clients about “problems in the inner city.” And our clients shouldn’t be making comments about Jewish attorneys liking money.  At a recent legal dinner in our community, a senior lawyer told me that he referred to female attorneys as “attorneyettes.” I tried to avoid visibly rolling my eyes.

Senior attorneys may not realize that the law has changed. As a child, I remember asking my mom why it took her so much longer than it took me to fasten her seatbelt in a new car.  She said, “I’ve seen a lot more types of seat belts than you have, so I have to think about it more.”  This explanation made sense, and it also explains why more senior attorneys may not realize that the Rules of Civil Procedure have changed or case law regarding discovery responses has evolved. They have seen the law take many different forms and it may take them a while to realize that the standard on a motion to dismiss is now Twiqbal instead of Conley v. Gibson.

Finally, senior attorneys may not recognize the difference between personal preferences and “the right way to do something.” I’ve sparred with more senior attorneys when their approach is simply different than my own—they want to send a deficiency letter and I want to start things off with a friendly phone call. They don’t want to start sentences with “and,” while I believe that sentence-starting conjunctions are perfectly acceptable and often desirable.2 The client doesn’t want to grant a courtesy extension, and I’m OK with it. And don’t get me started on the one space vs. two spaces after a period debate.

How to navigate these issues? The same way that authors advise us to talk with millennials—open and honest conversations. When a senior attorney, with no malice, reports that an African American associate was “articulate” during an oral argument, I think I have an obligation to respond, “That’s awesome!  But can I send you a New York Times article about the word ‘articulate’ and why some folks might be offended by it?” When they cross my radar, I will always share caselaw updates or developments with clients and partners. And when my personal preferences clash with a more senior attorney’s, I’ll make my best pitch for my method, but defer to the person running the case.

Despite these issues, however, I’ll end with a bit of an ode. Senior attorneys have seen a lot. Due to the breadth of their experiences, they tend to be unflappable when the inevitable surprises in litigation occur. They can offer perspective (that terrible deposition really wasn’t so bad, and you’ll have hundreds more). And I’m always surprised at how accurately a senior attorney can guess what the next side’s offer will be in a mediation, and that’s because they have a seen this process unfold before.

So my final takeaway is that we are all stronger together. When we create a legal team that has a depth of experience, a knowledge of the most recent legal developments, and in which smart people can wrestle with strategic decisions together, we will get great outcomes. Indeed, research conducted at Google demonstrates that teams achieve the most extraordinary results when group norms facilitate collaboration and cooperation among diverse participants. When group norms discourage collaboration, the collective intelligence of the group can never exceed that of any one individual. But collectively, we bring a whole lot to the table, together.


  1. “The word perfectly conveys, to quote George Bush, the soft bigotry of low expectations. It literally comes down to that. When people say it, what they are really saying is that someone is articulate … for a black person.” Anna Perez, former deputy assistant to President Bush and communications counselor to Condoleezza Rice when she was national security adviser.
  1. Legal-writing guru Bryan Garner agrees. (“The shorter word affords a brisker pace.”).

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