By Andrew Dick
October 15, 2025
Oringinally published in Law360 (link to article)
In today’s legal market, landing new work isn’t about having the longest deal sheet or the most decorated bio. It’s about showing up with curiosity, commercial awareness, and the ability to engage in a meaningful way from the start. In this competitive environment, general counsel are not just evaluating what you know — they’re watching how you think, how you listen, how well you prepared and whether you are mindful of the larger business context.
The most successful attorneys treat the pitch process as the beginning of a relationship, not a one-off sale. They ask thoughtful questions, connect the dots between legal and business priorities, and offer insights that make clients feel like they’re already working together. These moments of connection often matter more than credentials.
In this article, I’ll share seven practical tips based on what general counsel say actually moves the needle during the RFP process.
If you’re in the room (or on the call), the client already believes you have the technical chops. Repeating your resume doesn’t move the conversation forward — it stalls it. GCs aren’t hiring bios; they want to know how you think and what it’s like to work with you.
Start by getting right to the heart of the matter. Ask smart, strategic questions that show you’re not only thinking about the legal matter in the RFP, but also about the company’s broader business goals and strategy. Ask what the client’s objectives are for the matter — don't assume you already know. Ask how similar issues have been handled in the past, where the internal sensitivities lie, and what success looks like from their perspective.
This kind of questioning shows that you’re thinking holistically, not in a vacuum — and it builds immediate credibility. It signals that you’re approaching the conversation as a business partner, not just outside legal support for a discrete matter.
If you’re pitching a company, you better know exactly what they sell — and ideally, have used it yourself. For consumer-facing companies, that means downloading the app, buying the product, or walking through the customer experience first-hand. For B2B offerings, it means reading customer reviews, listening to investor calls, browsing industry commentary, or exploring how the product is positioned in the market.
This level of familiarity not only shows initiative — it also demonstrates that you’re genuinely interested in what the company does and how it creates value. It also gives you the language and context to ask better questions and offer more relevant insights during the pitch.
Nothing builds credibility faster than showing you’ve taken the time to understand the very product or service that the company — and everyone inside of it — is working very hard to sell.
3. Offer Value Right Away
Clients remember who gave them something useful — not just who gave them a pitch. If you can share a strategic thought, flag a potential risk, or suggest a resource that adds value in real time, you’ll make yourself memorable.
Even something simple — like noting a new classification risk in a state they have employees or pointing out an upcoming SEC rulemaking that might affect their industry — signals initiative and awareness. Even if your insight isn’t directly related to the matter at hand, it shows that you’re invested in helping the client succeed.
This creates momentum. It also reframes the conversation from trying to win a piece of business, to trying to understand how best to support the client’s goals and needs.
4. Tailor It to the Business, Not Just the Matter
Too many pitches are overly focused on the legal matter underlying the RFP without placing it in the broader context of the company’s strategic objectives. Great outside counsel ask how the matter connects to the business’s priorities, pressures, and timelines.
Before the meeting, listen to the client’s earnings calls, industry news, and recent developments. Use that information to frame your questions and insights. Think about what may be influencing how the client is approaching this matter. Are there investor pressures, fundraising milestones, internal policy shifts, or employee morale concerns that might shape how legal issues are framed or resolved? Asking questions that take into account the company's timing, strategy, and internal dynamics shows you’re thinking beyond the issue — and that you understand legal decisions don’t happen in a vacuum.
When you speak in business terms, you signal that you’re a strategic partner, not just a legal technician.
5. Make It Feel Like You’re Already on the Team
The most effective pitches don’t feel like a pitch at all — they feel like the first working session. When you ask meaningful questions, listen closely, and build on what you hear, you help the GC experience what collaboration with you would actually be like.
Reach out in advance of the pitch with pointed questions or to gather relevant context. Are there business dynamics or internal sensitivities that would help you tailor the conversation more effectively? That simple step shows initiative, professionalism, and respect for the client’s time.
Just as importantly, follow up after the pitch. Revisit questions that came up during the discussion or circle back with clarifications or resources. Clients remember who stays engaged after the meeting, not just during it.
It’s not about reading from a slide deck. It’s about engaging in a real conversation.
Clients want to know: Can I trust this person to show up well in front of my CEO? Can they flex with changing priorities? Do they think beyond the brief? You want the GC to walk away thinking, "I already feel like we’re working together."
6. Prepare Like It Matters, Because It Does
You can’t expect to stroll in with a generic pitch, recite a few past wins, and rely on your law firm’s brand name to carry the day. Clients expect more and they can tell instantly when you haven’t put in the work.
Preparation is table stakes, but you’d be surprised how often attorneys underprepare. Clients notice.
Read the company’s latest 10-K. Know who their competitors are. Understand their market pressures. As noted above, reach out in advance (if appropriate) to ask a few framing questions. These steps don’t just help you tailor your pitch — they demonstrate that you care.
Preparedness is one of the clearest signs of respect. And in a pitch process, respect builds trust.
7. Listen Like a Business Partner
Pitch meetings shouldn’t be monologues. The best conversations happen when lawyers listen more than they speak.
Ask open-ended questions. Pause before jumping in with a solution. Reflect back what you hear. Clients want to feel heard — not sold to.
When you approach the meeting with curiosity and active listening rather than a canned pitch, you’re more likely to uncover the real priorities and pressures behind the matter. That leads to insight that you can leverage to set yourself apart.
Final Thought
The pitch process isn’t a performance. It’s a preview. How you show up in that moment shapes how the client imagines working with you going forward. If you approach it with curiosity, clarity, and care, you won’t just increase your odds of winning the work, you’ll lay the foundation for a long-term partnership.
And at the end of the day, that’s what clients are looking for from their law firms.
Andrew Dick is VP of Strategic Initiatives at The L Suite where he runs Client Quotient™, an on-demand learning platform with GC insights to help law firms understand what clients want.
GET STARTED
©2025 Client Quotient. All Rights Reserved.