Cross-selling has been talked about for decades, yet very few firms feel they have really cracked the nut. That tension between the promise of cross-practice collaboration and the reality of cultural, structural, and psychological barriers set the tone for our CMO Series Live event in Chicago.  

Eugene McCormick moderated the conversation with legal marketing and business development leaders and strategists.

• John Sterling – Chief Strategy Officer, Chapman and Cutler
• Andrew Katznelson – Chief Marketing and Business Development Officer, Epstein Becker Green
• Mo Bunnell – Founder and CEO, Bunnell Idea Group

What followed was an honest, highly practical discussion about what actually moves the needle when it comes to cross-selling. Below are the biggest takeaways from the session, along with practical ideas which firms can put into action immediately.

The Business Case Is “Undeniable”, Yet Still Underleveraged

Eugene opened with some data points that everyone in the room recognized:

• It costs five to ten times more to win a new client than to deepen an existing relationship.
• Upselling current clients can increase revenue by 30 percent.
• Involving three or more practices in a client relationship dramatically boosts retention, longevity and profitability. 

Despite the upside, cross-serving a client remains one of the hardest things for firms to operationalize. The reasons, the panel agreed, are overwhelmingly human. Add in decades of siloed structures, the “my-client” mentality, risk aversion, and memories of one introduction that went badly years ago, and you have a recipe for hesitation, not collaboration. Cross-selling is not about pushing services; it is about helping clients solve problems. And clients trust firms more when multiple experts are invested in their success.

“Clients do not like you coming to them with something you want to sell. They love it when you come to them with someone to solve their problems.”  (John Sterling)

Best Practices: 

1. Start with the Client – Every successful approach begins with understanding client priorities, in their language, not legal jargon.
2. Make Introductions Easy – Lower the cognitive and emotional friction for partners by giving them a ready-made starting point.
3. Build Confidence and Reduce Fear – Partners worry about looking foolish or introducing the “wrong” colleague. Coach partners on how to present their colleague with context. Reframe selling as “helpfulness and curiosity.”
4. Reward Behavior, Not Just Revenue – Immediate, symbolic reinforcement works better than annual compensation changes. Celebrate those that succeed at every opportunity with public shout-outs, internal spotlights, and leaderboard recognition.

“You do not tell a dog to sit and then maybe give it a treat in 6 months or at the end of the year. It needs to be immediate to drive the behavior change.” (Mo Bunnell) 

“Start with the client — their needs, their reality. That is where the true opportunities are.” (Andrew Katznelson)

The analogy is being a caddy — tell the person how the hole is, which way the wind is blowing, what club they should hit — but eventually the partner has to take the shot.” (John Sterling)

The building blocks to cross-selling

Our panel was keen to underline that there was “no silver bullet” but that cross-serving a client effectively is a culture, a mindset and a series of consistent behaviors to deliver great results for your clients. It all starts with understanding the client's needs.

1. Structured Client Listening Tours – Have a managing partner and senior BD leader visit top 20 clients with a semi-structured question set.  A structured, off-the-clock conversation that simply asks: “what keeps you up at night?” or "what could we be doing better?” reliably uncovers opportunities. Encourage partners to use follow-ups like “Tell me more…” to chase emotional and business cues.
2. Gamified Check-In Program – Lawyers earn points for asking clients (live) about next-year priorities. Live conversations (NOT over email) make all the difference. Track laterals with accountability touchpoints and a 90-day plan for mapping clients to their capabilities.
3. Give-to-Gets – Create 5–6 short, specific, no-cost engagements without asking anything in return. It could be anything from 30-minute trend briefings, IPO or readiness checklists, to private equity or regulatory updates and tailored market snapshots. These small offers create natural openings for introductions and build confidence and the sense that “this person gets me and cares.”

“Start with the client. What does the client really want? If you do not know that, you do not know where the true opportunities are.” (Andrew Katznelson)

“Have metrics at every level (individual, practice, firm) to understand what you are trying to achieve.” (John Sterling)

“It is a thankless job. There is always a bio, an emergency RFP. The work never ends. You’re going to be dead and there will still be emails. So, pull back five minutes at the end of the day and write down how you moved things forward.” (Mo Bunnell)

The Chicago discussion made one thing clear: effective cross-selling is not a paint-by-numbers exercise. It requires empathy, accountability, curiosity, and a firm-wide commitment to helping clients, not pitching services. 

Some partners excel in live meetings. Others are strong connectors. Others shine in thought leadership. What matters is matching tactics to strengths, not forcing a single approach. For marketing and BD leaders who feel stuck in the day-to-day of their jobs, even a daily five-minute reflection, asking yourself: “What moved forward today?”  helps maintain momentum in a role where progress is often invisible. Professional services growth does not come from harder selling. It comes from deeper listening, better collaboration, and a culture that celebrates doing the right thing for clients every time. Cross-serving evolves as the firm evolves, and the playbook needs to evolve with it.