Because cross-selling, or cross-serving as some prefer to call it, can be a challenging endeavor in many law firms, and given James Barclay’s friendship, I didn’t want to miss his session at our recent Legal Marketing Association annual conference in Washington, DC.
James, who is the CEO of Passle, delivered a compelling session titled “Harnessing AI for Cross-Selling: Don’t Miss an Opportunity for Growth!” With his trademark humor, intelligence, approachability, and clarity, James guided us through a practical, numbers-backed exploration of how AI can help solve one of law firms’ oldest and most persistent challenges: getting lawyers to cross-sell.
James kicked off with an undeniable truth: cross-selling remains the most significant opportunity for revenue growth in law firms. He cited statistics from law firm leaders and marketers showing that more than 84% of firms admit to leaving money on the table due to missed cross-selling opportunities. That is a very large and startling number.
“If you’re an Am Law 100 firm, even a 10% increase in cross-selling could mean $135 million in new revenue.”
Despite its potential, few firms consistently do it well.
James challenged the audience to treat cross-selling not as a mystery, but as an internal communication and systems problem.
James traced the structural roots of the issue back to the Cravath system, developed in 1902. That model helped law firms grow in response to increasingly complex client needs, but it also created a hierarchy and specialization structure that often impedes internal collaboration today.
“Cravath transformed lawyers from individual actors into a cohesive force, but that cohesion is fraying.”
Fast forward to today, where hybrid work, global teams, and compensation models built around origination often isolate lawyers from one another, causing them to work in siloes. The result? Many attorneys are unaware of what their colleagues do, fear being perceived as salesy, or feel the “ick” factor, as James puts it, causing them to hesitate in trusting someone else with their clients.
I have seen this challenge in varying degrees ever since I was in-house as the senior marketer at Baker & Daniels. We must continue to chip away at this issue because it is costing our firms deals, dollars, and cohesion both within and outside the firm.
James shared data from 200+ general counsel, revealing a major gap in perception:
- GCs spend at least 8 hours a week staying informed…an ENTIRE DAY!
- They consume content in short bursts, often outside work hours.
- Half said they only work with firms that demonstrate subject-matter expertise.
And the unfortunate quote that James shared with us:
“The number one complaint from clients is: ‘You only talk to us when there’s a bill.'”
This mismatch between clients who want proactive, helpful insights and lawyers who fear being pushy creates a massive opportunity for marketers to bridge the gap.
James and volunteers from the audience highlighted solutions already working at law firms:
- Key client programs
- Fast Pitch Fridays, where attorneys explain their practice to peers
- Cross-practice group collaboration on content
- Internal success storytelling to show what good cross-selling looks like
- Partner retreats that encourage meaningful connection
One attendee shared that their firm had recently put a member of the management committee in charge of cross-selling to increase accountability and momentum.
Legal marketers are often told to “show the value of marketing,” but James, and speakers like my other dear friend and colleague, Gina Rubel, suggested a reframe:
“Don’t call it data. Call it evidence. Speak to your lawyers the way they hear best.”
Gina is a lawyer and the head of a very successful PR and Crisis Comms agency, Furia Rubel Communications, so the reframing comes authentically. Gina shared that this mindset shift can help you gain buy-in when presenting cross-selling success stories, especially when you frame them around shared client wins.
Here’s where the session became especially actionable. James walked through how legally trained AI can:
- Analyze attorney bios and blog content.
- Identify themes and client-relevant topics, both in bios and in content being created inside the fir.m
- Match those topics and thought leadership with other internal attorneys who should or could share it with specific clients who need to know about these topics and issues.
- Automate the notification to those lawyers so they understand why they might want to share that specific piece of content with specific clients.
- Provide easy, editable email templates that eliminate the “ick factor” so they can share something with their clients that they now know would be relevant to them.
As James said:
“AI doesn’t just write content. It can quietly orchestrate the distribution of relevant insight to the right people at the right time.”
James took a few quick moments to show us Passle’s approach to automating the bullet points I mentioned above. The Passle AI feature triggers new smart notifications, where lawyers receive an alert when their colleagues publish content that would resonate with their clients, along with a summary, a suggested email message, and an explanation of why it matters to their practice, company, or business.
- Cross-selling is the lowest-hanging fruit for firm growth.
- Law firms already have the necessary inputs (bios and thought leadership).
- AI helps streamline the messy middle, matching, summarizing, and sending
The time to act is now: As so many of us who spend time in the AI space have been sharing for a few years, “AI is the worst it will ever be today. It’s only going to get better.” As James shared, whether you complete this process manually or automate it with a tool such as the one he and his colleagues at Passle provide, it is essential to do so.
For a running collection of content created about the conference, please visit and bookmark this blog post and check back frequently as I will be adding to it over the next several weeks.
