The Conversations That Lead to More Work (and Stronger Relationships)

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I once heard an interview with a successful chef who trains his team to never ask the diner, “How is everything?”

Why? Because rarely does it reveal anything useful. The answer is almost always the same: “Fine.” Ask canned questions, get canned answers.

Instead, he teaches his servers to ask better questions.

“What’s been your favorite dish so far?”
“Was there anything you’d love to see on the menu next season?”
“Do you usually eat this style of food, or is this new for you?”

Those questions create a moment. They open the door to connection, to insight, and yes — to repeat business.

I thought about that again recently while coaching a group of lawyers who were trying to deepen relationships with existing clients. One of them said, “Every conversation feels like I’m just giving updates, answering questions, and moving on.”

Exactly. That’s how most client conversations go: Update. Question. Decision. Rinse and repeat.

And while there’s nothing wrong with those interactions—they’re necessary—they rarely lead to bigger conversations, stronger relationships, or new work.

So we talked about a simple mindset shift to move conversations beyond the immediate billable matter.

If you want to be the lawyer who gets the next call—ot just the one handling the issue in front of you—you need to step outside the boundaries of the current matter and get the client to think more expansively.

That means making space in your conversations to ask about:

Business Strategy

“What are the biggest growth opportunities you’re pursuing this year?”
“Where’s the business headed, and what’s changing along the way?”

Industry Context

“What’s new in your world? Anything competitors are doing that’s caught your attention?”
“Any upcoming events or shifts in your industry that could affect your priorities?”

Personal Goals and Challenges

“How has your role evolved lately?”
“What are you most focused on right now — and what’s making that harder?”

None of these require a long lunch or a client retreat. They just require intention. Five minutes of a conversation that isn't about the active matter can open the door to work that isn’t yet on the table—but should be.

Try This

In your next client call, ask one question that’s not about the matter in front of you.

That’s it.

Listen. Take notes. Ask a follow-up. You’ll be surprised how often a deeper need comes to light—something they hadn’t quite gotten around to calling a lawyer about.

And here’s something else that often happens: When you ask what they’re seeing in their industry, they’ll turn around and ask what you’re seeing.

Clients want the advantage of your unique vantage point. You work with multiple companies, often in similar sectors or facing comparable challenges. You see patterns. You notice trends. You’ve had conversations they haven’t.

Be ready for this. You should want this.

It’s your chance to deliver value in the moment—not just through legal analysis, but through context, insight, and perspective. That’s how you become not just the lawyer handling the matter, but the one they want to call before the next one even arises.

It’s not about turning every conversation into a pitch. It’s about showing up with curiosity and context. That’s how you go from being a service provider to a trusted advisor.

And those are the lawyers clients want to give more work to.



Jay Harrington is president of our agency, a published author, and nationally-recognized expert in thought-leadership marketing. 

From strategic planning to writing, podcasting, video marketing, and design, Jay and his team help lawyers and law firms turn expertise into thought leadership, and thought leadership into new business. Get in touch to learn more about the consulting and coaching services we provide. You can reach Jay at jay@hcommunications.biz.


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