In How to Find a Business Lawyer: A Practical Guide, we looked at how to identify lawyers who might be a good fit for the work you have in mind. For your initial meetings with those lawyers, here are some talking points you can use to get the best possible support for your company.

Start by giving a clear picture of your business

Share enough context so that the lawyer can offer useful comments right away:

• Where you are in the journey. Are you at the idea stage, getting traction, or expanding into new markets? Are you raising money, or bootstrapping? Just a few founders, or hiring a team? If you’re comfortable, share simple numbers like headcount or revenue range.
• A description of your product or service, and your revenue model. Advice for a B2B SaaS company will look very different from guidance for a consumer-focused clothing manufacturer. 
• The kind of help you need. The more clearly your question is defined, the faster you’ll get useful feedback. For example:  
  • Instead of “We’re at the stage where we need a corporate lawyer,” try “We’re forming an LLC and want to make sure the ownership split is documented correctly.”  
  • Instead of “Can you draft a contract that protects us?” try “We’re negotiating a master services agreement with our first enterprise customer. Our biggest concerns are getting paid on time, keeping our process confidential, and limiting our liability.”

If you can, send a short email ahead of time with high-level key points. Even a quick summary can turn a generic call into a productive one.

Questions to ask lawyers

After you’ve introduced yourself and your business, here are some questions that will quickly determine whether the lawyer is a good fit for your projects.

1. “What work do you do — and what work *don’t* you do?”

The lawyer should define their practice area clearly, giving examples of matters they’ve handled that are similar to yours. Be cautious if someone insists they can do everything by themselves. That said, you may want a firm (or a lawyer with a strong network) that can cover multiple areas. Here, a good answer can sound like “I handle corporate and contracts, and refer healthcare regulatory questions to an expert in my network/at my firm.”

2. “Do you work with businesses like mine?”

Listen for experience that matches your size and stage, not just your industry. If the lawyer mainly represents individuals, they may not appreciate how urgent business deals can be. If they represent huge companies, they may overcomplicate routine work. If they usually represent the “other side” of your deal (for example, they work for investors and you’re raising money), they may not naturally focus on your concerns. You can ask directly: “How many contracts like mine do you do per year?” or “What size company do you normally support, in terms of annual revenue?”

3. “How would you approach my issue?”

Can the lawyer explain how they would approach your issue, in plain language? Many lawyers are able to produce an uninterrupted “wall of sound” that is highly polysyllabic yet 100% content-free. Please feel free to interrupt this politely with “Can you walk me through the actual steps you’d take?”

On the other hand, if the lawyer gives a succinct, understandable set of options, that’s a good sign. A strong attorney can translate complexity into a clear (if not always simple) plan.

4. “Do you have any questions for me about what we sell and how we make money?”

Your lawyer doesn’t need to be an expert in your product. But they should be able to understand your business model quickly — or at least ask insightful questions until they do. If you have a tech company, it’s helpful if they’ve used or otherwise experimented with the type of technology you’re selling.

5. “How do you balance risk and speed?”

Every founder lives with trade-offs. A lawyer who obsesses over every boilerplate contract term can slow you down. A lawyer who’s too casual can expose you to unacceptable risks. If they hold forth on court cases, intricate contract wording, or government bulletins, they may be experts in these areas rather than business-focused. If they dig deep into your pricing, distribution strategy, differentiators, or competition, it’s more likely they’re in touch with the commercial market.

6. “What deliverables will I actually get?”

Once you and the lawyer have discussed the scope of the product, you can ask for more information about what exactly they’ll do for you. Is it a set of corporate documents? A contract markup? Compliance advice? The answer can go into your engagement letter or retainer agreement so you can both be on the same page.

7. “How long does this kind of matter usually take?”

The lawyer will almost certainly not be able to promise a date, especially for filings subject to government approval and contracts that need input from the other side. However, they should be able to give a range of typical timelines, and explain what can expedite or delay the project.

8. “How will billing work?”

Whatever the model, the lawyer should be able to explain billing clearly and tell you what a typical total cost looks like for similar matters. The most common approaches are:

• Hourly billing. Often the easiest way to compare across lawyers. Ask about hourly rates and how they track time.
• Flat fee. Works best for routine, predictable work. Make sure you understand what’s included—and what triggers extra charges.
• Subscription / monthly plans. Can be helpful if you expect ongoing questions and want uninterrupted access, e.g., a fractional general counsel arrangement.

You may also want to get information on how the lawyer manages to a budget, and when they flag that scope is expanding.

9. “What do you need from me?”

What input does the lawyer expect from you as part of the legal process? You’ll be called on to make decisions that may affect your company for years to come. Your lawyer should be able to give you options and explain how each will affect you.

Red flags

How the lawyer interacts with you is as important as their legal knowledge. Watch for these warning signs:

• They hold forth on where they went to school, awards they’ve won, or prestigious jobs they’ve held, but don’t have much to say about how they’ve helped actual clients.
• Their client list is impressive but irrelevant (for example, they’re all large corporations when you’re a small startup).
• They don’t ask questions about what you do and don’t seem particularly interested in learning about your business.
• They can’t or won’t explain how they plan to handle your project.
• They talk over you or rush you.
• They seem evasive about fees or timelines.

Finally, as you would with any professional, check with the state to confirm that the lawyer is licensed, and do a quick online search to double-check their reputation.

The value-added lawyer

We hear a lot about 10x engineers; is there such a thing as a 10x lawyer? As important as it is to keep you out of court and close deals on time, can a good lawyer bring more to the table? Here are real value-adds to listen for:

• A broad and deep network: referrals to skilled accountants, insurance brokers, tech providers, or specialist lawyers when needed.
• Market awareness: knowledge of what’s normal in deals like yours, which is especially helpful for first-time founders.
• Negotiating on an equal footing with larger, more experienced investors or customers: no need to be overwhelmed by 60-page contract templates when your lawyer is on call for a quick turnaround.
• Structure and follow-through: great lawyers manage details and predict next steps so you can stay focused on running the business.

The ROI of the right counsel

Hiring the right lawyer can offer a return on investment beyond closing a deal or avoiding a compliance mistake. It’s about getting clarity from someone who has seen your situation many times before — so you make better decisions, faster, with fewer surprises.

Go into the interview aiming to answer one question: Will this person help my business move forward? If the answer is yes, the relationship can pay for itself many times over.

 

If you have any questions about how to find and interview the right lawyer, please feel free to contact us. We’re happy to have a conversation about your business, no matter who you end up hiring.