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.
Why Cross-Selling Is the Growth Engine Hiding in Plain Sight
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.
A Brief History of Why Law Firms Struggle with Cross-Selling
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.
This Isn’t New
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.
What Clients Actually Want: Connection and Relevant Content, Not Silence
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.
What Marketers Can Do Right Now
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.
Speak Their Language: Make the Case With “Evidence”
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.
How AI Can Turbocharge Cross-Selling
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.
Final Takeaways: The Future Is Now
- 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.
Conference Content Can Be Found Here
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.
About Nancy Myrland
Nancy Myrland is a Marketing and Business Development Advisor, specializing in Content, Social & Digital Media. She helps lawyers grow their practices by integrating the most important marketing practices to build their reputations and relationships, which in turn leads to the growth of their practices.
Highly regarded internationally as a top independent* LinkedIn consultant, Nancy is a highly respected LinkedIn trainer and content marketing specialist. She helps lawyers, law firms, and legal marketers learn and implement content, social, and digital media strategies that cut through the clutter, making them more relevant to their current and potential clients.
She is also a personal branding speaker, trainer, and advisor, helping legal and business professionals understand the importance and the impact of defining and reinforcing their personal brands.
Nancy is also the founder of the hybrid self-study and online course about LinkedIn, The Linked Course*, where she personally guides lawyers through the sequential creation of their LinkedIn profile and presence.*
As an early and consistent adopter of social and digital media and technology, she also assists firms with blogging, podcasting, video marketing, voice marketing, livestreaming, and AI discernment. Nancy also works with numerous firms and lawyers on Zoom and virtual presentation training and coaching to help them excel when presenting online.
She also helps lead select law firms through their online social and digital media strategy when handling high-stakes, high-profile cases and executive orders.
Long story short, Nancy spends a lot of time helping lawyers and legal marketers with:
- LinkedIn Profile and Presence
- Podcast Launches and Consulting
- Content Marketing Strategy
- Marketing and Business Development Plans
- AI Discernment
- Personal Branding, and
- Zoom and Virtual Presentation Training and Coaching
*Nancy is not an employee or consultant hired by LinkedIn, although she was named a LinkedIn Top Voice on the platform in 2024! Top Voices is an invitation-only program featuring a global group of experts on LinkedIn covering a range of topics across the professional world, helping members uncover valuable knowledge relevant to them. Top Voices was previously known as the Influencer program before October 2022. Top Voices are vetted to ensure that they meet high trust standards, are consistently active on the platform, and share valuable expertise through content that demonstrates their unique, original contributions to a topic.
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