Client Relationships Suffer as Lawyers Put Billing on Autopilot

Now is the time of year when many law firms pressure their attorneys to get their clients to pay bills before the end of the year. It's something that clients loathe just as much as their attorneys, according to today's guest on our podcast, On The Merits. Eric Dodson Greenberg, the general counsel of Cox Media Group, said the lawyer-client relationship can suffer when firms bill too aggressively and not thoughtfully enough—a problem made worse by the move toward automated billing. He said he's lost some trust in certain outside firms he's worked with when they send him surprise invoices. "What law firms have done is divorced the billing process from the exercise of judgment," he told Bloomberg Law editor Jessie Kokrda Kamens. "Law firms often prioritize that last push in December to get all that they can and not really focus on 'What's the relationship we inherit on January 1st?'" Do you have feedback on this episode of On The Merits? Give us a call and leave a voicemail at 703-341-3690.

OpenAI is a relatively new tech startup with the litigation demands of a massive Fortune 500 company. That means that Che Chang, its general counsel, has had to scale up his department fast. On today's episode of our podcast, On The Merits, Chang speaks with Bloomberg Law reporter Aruni Soni about how he hires lawyers to work for the ChatGPT maker and how OpenAI works with its outside law firms. On top of these usual legal officer duties, Chang discusses the "immense responsibility" of guiding decisions around the "future of human intellect." Do you have feedback on this episode of On The Merits? Give us a call and leave a voicemail at 703-341-3690.

It's been a difficult year for Brad Karp, chair of Wall Street law firm Paul Weiss. In January he suffered a heart attack and then, a few months later, he chose to strike a pro bono deal with the Trump administration to stave off a punitive executive order.  In a recent speech at a gala event in New York, Karp said the latter was more painful than the former. But during that speech, a fellow attorney stood up and heckled him—an indication of how raw feelings within the legal industry still are over the pro bono deals. Bloomberg Law reporter Mike Vilensky was at the event and saw all of this go down. He joins our podcast, On The Merits, to talk about who shouted at Karp, why, and what the two had to say to each other after the event concluded. Do you have feedback on this episode of On The Merits? Give us a call and leave a voicemail at 703-341-3690.

As Big Law looks for ways to scale up, McDermott Will & Schulte says it's looking at outside investment in the firm—a move that could set off a paradigm shift in how law firms run their businesses. If it does sell a part of itself to investors, McDermott would be by far the largest publicly known firm to take this step. Outside investment represents a new source of capital for law firms looking to expand, but does come with myriad risks and potential roadblocks. On this episode of our podcast, On The Merits, Bloomberg Law's Jessie Kokrda Kamens and Justin Henry talk about why McDermott is doing this now, whether they can pull it off, and how they're going to get around the ethical rules prohibiting outside ownership of firms. Do you have feedback on this episode of On The Merits? Give us a call and leave a voicemail at 703-341-3690.

The top lawyers at the largest publicly traded companies in America are being asked to wear many hats at once—and also getting paid handsomely to do so. That's the takeaway from a recent story by Bloomberg Law senior reporters Brian Baxter and Andrew Ramonas, who crunched data from SEC filings of S&P 500 companies and found out how much these attorneys are making. Alphabet's J. Kent Walker Jr. leads the list with a total compensation package exceeding $30 million. On this episode of our podcast, On The Merits, Baxter and Ramonas talk about who these highly paid executives are, the new responsibilities they have, and why they don't always hold the titles of "general counsel" or "chief legal officer" at their respective companies. Do you have feedback on this episode of On The Merits? Give us a call and leave a voicemail at 703-341-3690.

Most of the biggest law firms in the US have a two-tier partnership model, where some partners have equity in the firm while others don't. So it was a bit of a surprise when the firm Ropes & Gray announced last month it will be sticking with its one-tier model.  Is this a sign that the trend toward non-equity partners is starting to reverse? Not according to today's guests on our podcast, On The Merits, law firm consultant Janet Stanton with Adam Smith Esq. and legal recruiter Scott Love with The Attorney Search Group. They talk with Bloomberg Law editor Jessie Kokrda Kamens about how prevalent non-equity partnerships are, how they benefit law firms, and what firms need to avoid doing to make sure they work. Do you have feedback on this episode of On The Merits? Give us a call and leave a voicemail at 703-341-3690.

On this episode of our podcast, On The Merits, we take another look at the reasoning behind the deals law firms struck with the Trump administration earlier this year to avoid punitive executive orders. We previously heard from Yale Law School professor John Morley, who said these firms had no choice because an executive order could have kickstarted a devastating run on the partnership. Today's podcast guest sees it differently. David McGowan, a professor at the University of San Diego School of Law, says the firms that settled did so because they forgot the unique role they play in the American justice system and, instead, see themselves as more of business venture. "To me, the firms that have come to terms with the administration are signaling that, at their essence, they are financial services, financial adviser companies," he said. "I don't think that that is a given. I think that that is a choice." Do you have feedback on this episode of On The Merits? Give us a call and leave a voicemail at 703-341-3690.

Goodwin Procter made a splash this month when it announced it had raked in $2.7 billion in the 2025 fiscal year, a record for the firm and a 12% gain from the previous year On this episode of our news podcast, On The Merits, we hear from the firm's chair, Anthony McCusker, about how Goodwin managed this feat. He tells Bloomberg Law reporter Tatyana Monnay that he attributes the firm's recent success to a long-term strategic plan it developed called "Goodwin 2033." He also talks about where he thinks the legal industry is heading when it comes to tech—specifically, AI—and growing competition for law firms. "In a world where maybe the legal answer might be free, or quick to get into the world, clients are going to value that deep industry experience," McCusker said. "Clients are going to value that business advisory expertise that our lawyers bring. And so ensuring that we are preparing all of our people to be able to deliver that type of benefit to clients is one of the things we're really focused on." Do you have feedback on this episode of On The Merits? Give us a call and leave a voicemail at 703-341-3690.

President Donald Trump's attacks on law firms have hand their intended impact, even as courts shoot down executive orders against some as unconstitutional and the details of White House deals with others remain unclear, according to Yale Law School professor John Morley. "The point here is to extract a demonstrative form of obedience," Morely said. He said he's already seen a "chilling effect" with firms less willing to take on matters pushing back against the administration than in Trump's first term. Morley, who has studied law firm collapses, does not blame the leaders of firms that struck deals with the White House to avoid punitive executive orders. Court wins for the four firms who have challenged orders targeting them so far show that those firms made the right, albeit risky, choice to fight. "I am absolutely certain that, if one of these executive orders survived a temporary injunction proceeding, that would be the death of the firm," Morley said. "Or at least I think the probability is very high." Morley spoke to Bloomberg Law reporter Roy Strom on this episode of our podcast, On The Merits, about what has become of Trump's attacks on Big Law and what would happen if the President resumed them. He also discussed how they've changed the attitudes of his students at Yale about which firms they may want to work at in the future. Do you have feedback on this episode of On The Merits? Give us a call and leave a voicemail at 703-341-3690.

You don't get to be the oldest law firm in New York without weathering some rough spots. But this may be one of the most difficult periods Cadwalader, Wickersham & Taft has ever gone through.  The Wall Street firm, which this week announced a new managing co-partner, has lost nearly three dozen partners just this year. And not all of them have left because of the firm's controversial deal with President Trump for free legal services. On today's episode of our podcast, On The Merits, Bloomberg Law reporter Justin Henry explains why Cadwalader may be too specialized to thrive in today's full-service legal industry. He also talks about ways the firm can turn itself around without having to resort to a merger. Do you have feedback on this episode of On The Merits? Give us a call and leave a voicemail at 703-341-3690.