Midwest Region

Thank you to author Mia LaFlore, Sr. BD/Marketing Manager - Intellectual Property and Technology at DLA Piper and Planning Committee for the 2025 LMA Midwest Conference.

Session: Driving Profitability Through Cross-Selling
Speakers: Rob Randolph (Yate Collaborative) and David Sheppard (Sidley Austin)
Conference: LMA Midwest Regional Conference
Date: October 9-10, 2025, Chicago, IL

If you've ever sat in a cross-selling meeting where everyone's focused on filling white space on a spreadsheet, you know the drill. We look at our client list, identify what they're not using, and figure out how to push more services their way. Labor and employment here, litigation there. Check the boxes, move on.

But here's what Rob Randolph from Yate Collaborative and David Sheppard from Sidley Austin made crystal clear: we've been approaching this entire thing backwards.

It's Not About White Space. It's About Understanding the Client

The session started with a reality check that hit close to home. They asked us to identify which scenario best described our cross-selling efforts:

1. Strategic discussions about client business objectives that consistently result in new matters

2. General discussions that periodically result in matters

3. Partner-to-partner introductions that sometimes work out

4. Random partner introductions with no real results

Most hands in the room went up for options 3 and 4. Yeah. Same.

The problem? We're product-focused (our capabilities, our offices, our experience) when we should be client-focused (their pain points, their business objectives, their gains). We're trying to push what we want to sell instead of understanding what the client actually needs.

Cross-selling should start with identifying profitable clients (those who pay bills on time, provide good realization, and return year after year). Then understand what they need, not what we want to sell them.

The Uncomfortable Truth About Compensation

David brought up something uncomfortable but necessary: If your cross-selling efforts aren't aligned with your firm's compensation structure, they will fail.

This is where marketing and BD professionals can bring real value. We can flag barriers to management, gather intelligence about what's blocking collaboration, and advocate for alignment between stated priorities and actual incentives.

Client Feedback: The Secret Weapon

Here's something unexpected: There is no better way to cross-sell than through client feedback interviews.

David was emphatic. Every single client feedback interview he's done has included cross-selling opportunities.

Why? Clients want holistic services. They prefer one firm handling M&A, antitrust, executive compensation, and privacy rather than managing four different firms. They want to know about your services if they can help.

Critical distinction: This only works when positioned as listening, not pitching.

The Four-Step Client-Centric Process

The speakers provided a practical framework for developing business strategically:

1. Client Insight: Understand how they make money, what's preventing them from making more, and what their pain points are. Use a business model canvas to map client revenue streams and cost structure.
2. Value Proposition: Determine what outcomes are worth to them. If acquiring a company means $100M in additional revenue, a $10M legal fee becomes reasonable.
3. Solution Development: This is where cross-selling happens naturally. You're assembling the team needed to solve the actual problem.
4. Client Engagement: Arm lawyers with questions, confirm you understand their pain points, and co-create solutions when possible.

The Story That Drove It Home

David shared a powerful Sidley example. They had a major client with two business lines (private equity and infrastructure). Great relationships on both sides, but infrastructure work wasn't meeting expectations.

The problem? PE was buying businesses to flip in 2-3 years. Infrastructure was buying businesses to hold for 10-20 years. Completely different time horizons, completely different legal needs.

An executive compensation lawyer who doesn't understand that distinction will structure advice around a 2-3 year horizon (which doesn't work for a 20-year hold).

The solution: Once they understood the "why" behind the work, infrastructure lawyers started introducing specialists who understood that dynamic. They began getting portfolio company business too.

All from asking "why" and understanding the business objective (not just the immediate legal task).

Practical Application

The speakers made us work through a real case study. Tables identified creative approaches:

• 50-state regulatory surveys to take compliance burdens off the client's plate

• Proprietary tech solutions for portfolio management

• "Office hours" for emerging funds to build future relationships

• Repositioning strategies for converting office space to residential

The point was practicing client-centric thinking that starts with business problems, not our service offerings.

Key Takeaways

1. Start with profitable client profiles, not white space. Identify ideal clients, then understand their needs.

2. Address compensation barriers. Surface these issues with management and advocate for alignment.

3. Use client feedback strategically. Position conversations as listening sessions. Cross-selling opportunities emerge naturally.

4. Understand the "why" behind requests. Don't just fulfill immediate needs. Understand business objectives to identify broader solutions.

5. Create solutions competitors can't match. When you build something tailored to a client's specific situation, they can't easily shop it around.

The Bottom Line

Cross-selling isn't about selling. It's about solving client problems in a way that naturally requires collaboration across your firm.

When you truly understand a client's business model, pain points, and objectives, the "cross-sell" becomes a natural extension of excellent client service (not a separate initiative you're forcing onto the relationship).

Resource recommendation: Heidi Gardner's white paper "The Collaboration Imperative for Today's Law Firms" addresses this in depth.

Authored by: Mia LaFlore, Sr. BD/Marketing Manager - Intellectual Property and Technology at DLA Piper and Planning Committee for the 2025 LMA Midwest Conference