How to Win Legal Clients: 5 Takeaways from Legal Leaders

The legal market is changing. Client expectations are rising. Technology is reshaping how work gets done.

But the fundamentals of winning and keeping clients haven’t disappeared.

Expertise still matters. So do responsiveness, trust, and results. What’s changing is what clients expect around them and what separates one legal provider from another.

During our recent webinar, How to Win Legal Clients in a More Competitive Market, senior legal and business leaders shared what they value from external counsel, what gets their attention, and what keeps legal service providers at the top of their list.

The panel brought together Jennifer Armstrong of TD Bank Group, Karen Uehara of AltaGas Ltd., Steve Cimicata of Volaris Group, and Chad Aboud of Goodlawyer, moderated by Apertera (formerly Alexa Translations) CEO Gary Kalaci. 

Watch the webinar below to earn 1 hour of Professionalism Content and explore the five takeaways that sparked the most discussion.

Table of Contents

Know the Client’s Business, Not Just the Law

Legal expertise is still the baseline. But clients are looking for more than the right legal answer.

They want external counsel who understand how their business actually works: their priorities, pressures, risks, opportunities, and pace.

Karen Uehara emphasized that in-house teams aren’t simply solving legal questions. They’re solving business problems. That changes what valuable outside counsel looks like. The strongest advisors understand the context surrounding the law and turn their expertise into practical, relevant advice. 

That knowledge also compounds over time. Steve Cimicata described the value of working with firms that understand his organization, its internal processes, and its key players so well that they can effectively step in when needed.

The takeaway: Expertise gets you in the door. Understanding the business makes you harder to replace.

Use Technology to Create More Space for What Clients Value

Technology proficiency is quickly becoming an expected capability. For legal professionals, the bigger opportunity is what that technology makes possible.

Jennifer Armstrong pointed to speed as a major driver of client satisfaction. Clients expect crisp, timely advice, and increasingly expect their external counsel to use AI and other tools effectively to deliver it.

Chad Aboud took that idea further. Technology can remove administrative and repetitive work, freeing up what he called “cognitive load” to learn more about the client: their company, industry, priorities, language, and ways of working.

That extra capacity can then go toward the work clients value most: applying judgment, anticipating needs, and building stronger relationships.

The takeaway: Use technology to create more capacity for the client.

Adapt to the Client, Not the Other Way Around

The strongest client relationships are built on a deep understanding of how the client works.

That means learning their teams, processes, communication preferences, and expectations, then adapting your approach accordingly.

Steve Cimicata described relationships with firms that understand his organization so well they know the internal processes and key players and can effectively step in when needed. That familiarity creates value that takes time to build and is difficult for another provider to replicate.

Gary Kalaci summed it up as being adaptable: ask clients what they need, understand how they work with their teams, and find ways to cater your approach to them.

The takeaway: The more seamlessly you can work within a client’s world, the more valuable the relationship becomes.

Relevance Beats Generic Outreach

In-house legal leaders are inundated with emails, updates, and pitches. Breaking through starts with relevance.

Karen Uehara described relevance as part of the “secret sauce” for retaining and expanding client relationships. The most valuable outreach reflects an understanding of what is happening in the client’s business and why it matters to them.

Chad Aboud made a similar point about starting from a place of curiosity. Instead of sending another generic legislative update, do the work to understand what the client cares about and tailor the conversation accordingly.

That requires more effort. It also gives clients a reason to pay attention.

The takeaway: Know what matters to the client before you hit send.

Build Trust by Giving Value Before Asking for Business

Strong client relationships are built over time. Every useful interaction creates another opportunity to strengthen trust.

Jennifer Armstrong emphasized the value of proactive communication: staying in touch, being a sounding board, and maintaining relationships as clients move throughout their careers.

Chad Aboud framed the same idea as a bank account. Before asking someone for business, make deposits in the relationship by offering something valuable, whether that’s a useful introduction, relevant insight, opportunity, or connection.

Those deposits add up. And when the time comes to ask for something, there’s already a foundation of trust behind the relationship.

The takeaway: Give first. Build trust before you ask for the business.

Want to explore more practical insights like these?
Visit our free, accredited CPD Resource Hub to watch additional webinars, listen to podcast episodes, and earn CPD credits on demand.

Frequently Asked Questions

1. What do in-house legal teams value most from external counsel?
In-house legal teams value expertise, responsiveness, and reliability, along with a strong understanding of their business. External counsel who understand a client’s priorities, processes, risks, and ways of working can provide more practical advice and become more valuable over time.

2. How can legal service providers differentiate themselves as AI and legal technology become standard?
Technology proficiency is increasingly expected. Differentiation comes from how legal service providers use the capacity technology creates: applying judgment, understanding the client’s business, anticipating needs, and building stronger relationships.

3. What business development approaches are most effective with in-house legal leaders?
Relevant, personalized outreach is more likely to resonate than generic pitches. Understanding what matters to the client, providing useful insights or introductions, and building trust before asking for business can help create stronger long-term relationships.