Share article:

10 Interview Questions Lawyers Moving to Business Should Ask

Lawyers spend a lot of time asking questions, and this skill will be critical to finding success in a new job.  To find the right fit, you’ll need to get answers from a lot of people – including your network, prospective employers and, perhaps most importantly, yourself. Here’s a list of 10 questions you should ask about any new role you are considering – along with advice on who and when you should ask.

1. What are the biggest challenges and opportunities facing [COMPANY]?

Many interviews often start with a description of what the hiring organization does, and some interviewers often then include a discussion of strategic opportunities as well as how your specific role can help address them. This knowledge will be critical to your success both as a candidate and an employee and it’s important to spend some time discussing it. If you have personal contacts at the company, reach out to get a candid read on any challenges. 

2. What is the culture like at [COMPANY] and what kind of person is successful there?

If you are coming from Biglaw realize this concept of culture may be completely foreign to you.  While the firms all claim to have a ‘culture’, outside of platitudes offered by the marketing department or recruiting department, few do.

Company culture and lifestyle can play a critical role in how happy you’ll be within a specific job and it’s important to ask about this as well. However, negative issues may not surface during the interview process. Probing deeper with personal contacts can be particularly helpful here: Ask about work-life balance, promotion paths, whether the company is open to employee feedback and what the company has been doing to promote diversity and equity. If you don’t have a personal contact, check out company reviews on sites like   

3. How long have you been at [COMPANY] and what do you like best about it?

This question is another great way to understand company culture – and also get a better feeling about the team you might be working with. In addition to hearing some positive aspects of the company, you’ll also learn what your hiring manager values. And you may discover potential issues – for example, if an interviewer responds, “I never get bored because things keep changing,” that might not be a fit for a candidate seeking stability. 

4. Why is this position available?

It’s important to understand whether a role is new or, if established, why it is vacant.  For a new role, follow up by asking about why the company decided to add this role at this time as well as the resources that will be available. If the justification for the role isn’t clear or if the tools needed for success aren’t available, you could be set up to fail. For existing roles, if the prior employee was promoted, that’s a great sign. Alternately, if the role has been subject to constant turnover, watch out.

5. What are the primary responsibilities of this role?

Hopefully you should have received a detailed job description prior to any interview – but unfortunately, job descriptions can often be very generic, or include a lengthy laundry list of tasks without highlighting what is truly important. Use the question to get a true understanding of what you would be doing in this role – and be wary if different stakeholders don’t seem aligned.  

6. What is the reporting structure for this role?

It’s important to clarify this as quickly as possible during the interview process: It tells you how senior the role is, can give you a better understanding of the strategic focus of the role and of course lets you know who your potential new boss might be as well as how many employees you might be managing. Accordingly, make sure to ask about this during initial screening calls, and feel free to ask hiring managers for more detail. For senior roles, you should also ask about the senior leadership structure and if you’ll be part of the leadership team. 

7. How would you define and measure success for me in this role?

This is an excellent question to ask hiring managers, and an important way to understand whether a role will be a good fit. Use this question to see how your skills will align with manager expectations, and help them visualize you in the role. Be prepared to respond with examples of how you’ve accomplished similar goals in the past.

8. What would you expect me to accomplish in the next 30, 60 and 90 days?

Asking about near-term goals for the role will help set you up for success if you do join the company – and also provides another opportunity to discuss your own background and how you can help. Insights you gain from this question will also help you determine what to highlight in additional interviews. And if few stakeholders agree on these near-term goals, that’s again a definite warning sign.

9. What is the compensation for this role?

Many candidates often struggle with how to discuss compensation. Ideally this is addressed early in the process with a talent acquisition contact, so you know you are aligned before engaging in deeper conversations. It’s important to understand the full suite of benefits that impact compensation: Bonuses, equity, PTO, healthcare and investments in training can all contribute. However, it’s likely best to ask about most of these after an offer has been made.

10. What are the next steps in the interview process?

As you close an interview, it’s always good to ask about what comes next. Not only does this tell you what to expect, it also shows you are interested in moving forward. And in some cases, hiring managers may show how interested they are in their response. During initial calls with internal and external recruiters, feel free to ask detailed questions about the number of interviews that are typical, whether a presentation or case study will be required, timing and who are the key decision-makers. If it seems appropriate, you may also want to ask how many candidates are being considered and whether any are internal candidates.

These questions should provide you with a strong understanding of any prospective employer as well as whether a potential role is a fit. However, it’s important to remember that you shouldn’t expect to get them answered all at once. There’s  a happy medium when it comes to questions: Candidates that don’t ask any questions don’t seem engaged, while those who ask too many may seem too demanding.

Prioritize questions for each discussion based on what is most appropriate and “read the room” to make sure you aren’t peppering interviewers with too many questions. Also remember that you can continue to ask questions after you’ve received an offer if you feel unsure. While there’s no such thing as a stupid question, it’s always helpful to ask the right person at the right time.

Share article:

You’ve Lost Your Job, Now What

You’ve Lost Your Job, Now What? If you’ve considered more than once leaving law for an alternative career, as painful as losing a job is, you may have gotten the proverbial blessing in disguise…


The ex judicata Checklist for Lawyers Who Want to Transition to a Nonlegal Career

Making the leap from practicing attorney to businessperson is almost certainly the most daunting professional challenge you will ever undertake…


Beyond Law – Finding Success in Alternative Careers

A lawyer’s education and experience ensure a skill set that readily transfers to virtually any corporate role, from marketing and business development to labor relations and human resources…