By UpCounsel Immigration Attorney Denise McGettrick

Whether you’re running a startup in its first year or a midsize company with dozens of employees, legal hurdles are a fact of life. However, before you even begin to address them, you must overcome an even bigger challenge: finding the right attorney.

For people without a legal background, such as CEOs, the process of finding and hiring an attorney can be stressful and time consuming. They don’t always know what questions to ask or what indicators to look out for and might end up with an attorney who isn’t really right for the job or the company.

The good news is that businesspeople definitely don’t have to resign themselves to picking the first attorney whose resume crosses their desk. In fact, when armed with a list a pertinent questions, people without a legal background are empowered to evaluate an attorney comprehensively before trusting them with the company’s future.

1. What experience do you have handling projects and companies like mine?

It goes without saying that you want to hire an attorney who has experience, but it’s not just the amount of experience that’s important, but also the kind.

That’s why you shouldn’t be satisfied with a one-word answer to this question. Instead, ask for details: When and where were the projects handled, and what was the outcome? Of what size and in what industry were your previous clients? After all, if you’re a biotech startup trying to hire employees in California, you likely won’t want to work with an attorney who has only handled employment matters for a large financial services company in New York.

2. Are there any conflicts of interest that I should be aware of?

Attorneys are responsible for divulging any potential conflicts of interest, even if they are never directly asked a question about them. However, it’s usually not a bad idea to inquire about them yourself.

What constitutes a conflict of interest? In short, it’s any situation in which an attorney would have an incentive to act in a way that benefits a counterparty.

For example, if you are negotiating a contract with another company and the lawyer representing you has worked with that other company in the past, your lawyer might be reluctant to fight on your behalf. They might not want to risk offending the counterparty and damaging their relationship with them because doing so would result in lost business opportunities for the attorney.

3. What strategy do you have in mind?

This one is straightforward. Any attorney who has put time and energy into considering your project should be able to give a well-developed answer to this question. If you encounter an attorney who can’t, move on.

4. What will this cost me?

While most attorneys will quote you an hourly rate or a fixed fee upfront, it’s important that you understand what this quote does and does not cover. For instance, will you also be responsible for reimbursing the attorney for expenses, such as transportation?

If you have a strict budget, this is also a good time to let the attorney know that.

5. How much time will this take?

Although unexpected challenges sometimes arise and cause deadlines to be pushed back, attorneys should be able to give an estimate of how long each phase of the project will take. Make sure that these estimates seem reasonable and fit with the timeline that you have in mind.

6. What mode of communication do you prefer?

Clear, timely communication between attorneys and clients is essential, and it’s important to hire an attorney whose communication style is compatible with your own.

For example, if you prefer to discuss business matters over the phone during your commute but your attorney relies almost entirely on email and rarely picks up the phone, you might not be able to talk to your attorney as often or as freely as you’d like. This impaired communication can have real consequences if an important detail slips through the cracks, so make sure that you and the attorney agree on how best to communicate.

8. How do you envision our professional relationship?

If you’re searching for an attorney with who can serve as a trusted advisor in the long term whereas the attorney is only looking for a short-term gig while they are between jobs, it’s probably best that you turn elsewhere for legal help.

This is far preferable to working with an attorney and developing a relationship with them only to discover that they no longer have the bandwidth to counsel you after the first project.

9. What’s a challenge that you’ve faced when working with a client and how did you resolve it?

If this question sounds familiar, that’s probably because it is. Questions about challenges and conflict resolution are a favorite among interviewers, no matter the position or industry, and with good reason. The manner in which people approach conflict reveals a lot about how creative and solution-focused they are, which is an important thing to know about any attorney who you’re considering hiring.

10. What about this legal area usually confuses your clients the most?

An attorney who can answer this question well is an attorney who is attuned not only to the legal challenges at hand, but also to the way clients think about them. They’ve also likely worked with clients like you. They’ll be able to provide context upfront that answers your questions before you find yourself confused by a complex legal issue or legal language.

Additionally, when a question does come up, the attorney will likely be able to answer it in plain English.

11. When was the last time you said “no” to a client?

While you don’t want to hire an attorney who will challenge your every move, you also definitely don’t want one who is so afraid of getting fired that they’re reluctant to question you when they have a legitimate concern.

This question can help you gauge the attorney’s moral compass and the strength of their convictions.

12. Who is your favorite fictional lawyer?

This question may be unorthodox, but an attorney’s answer is actually a great indicator of how they see themselves and their role. Is their idol a fighter? A thoughtful judge? A power-hungry potentate?

Consider whether you’d want that character on your team.

13. Is it more important to maximize revenue or minimize risk?

There is no one right answer to this question. Every attorney and business person has a different idea of how much risk can be tolerated, and the more similar your appetite for risk, the better you will get along.

The Takeaway

No matter who you’re interviewing, it’s difficult to gain a complete picture of someone’s capabilities and personality over the course of an interview. This difficulty is compounded when you’re someone without a legal background who’s interviewing an attorney.

Nevertheless, there are several questions you can ask an attorney that are designed to reveal how this individual thinks about legal issues and how they approach business relationships. Knowing this information will enable you to weed out the attorneys who don’t fit your specifications and hone in on one who does.

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About the author

Denise McGettrick

Denise McGettrick

Denise graduated from DePaul law school and has bachelor's degrees in economics and journalism from UT Austin. She is a Board Certified Immigration attorney with over 11 years of experience in obtaining employment based immigrant visas and work authorization for talented and extraordinary ability foreign talent. She focuses on serving startup companies and is active in connecting with talent in the technology, startup, and investment communities.

Denise’s prior experience includes over 10 years at top immigration boutique firms. She lives in Houston and represents business immigration clients from around the globe, including those who prefer communicating in Spanish.

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