Conversations with your mentor can get monotonous over time, however, you can do a lot to get the best out of each session. If you admire your mentor at the law firm then you’re already halfway through getting the best out of your relationship with them – a mentor-mentee association is more like a family bond and it benefits you in that you get to see how the pinnacle of your professional journey as an experienced lawyer will be for you and it helps your mentor inspire a young professional to accomplish great things.

However, getting the best out of your interactions with your mentor is another topic. You need to do your part as well, there’s much you can do to make your talks fruitful and to get informed and inspired in every session. To avoid getting stuck in a monotonous circle, stay prepared at all times, explore things, prepare a list of topics you’d like to discuss, and most of all, take your meetings very seriously. In this article, I will discuss how you can uphold your part of the mentor-mentee relationship, but most importantly, my focus will be on helping you create a list of inspiring questions to ask.

Let’s begin!

Always Be Prepare For Your Meetings

Everyone is a rookie, the new guy – and one of the most rewarding experiences in the legal business is mentoring young professionals in their path to prominence and professional excellence. Mentors can have a lasting impact on the personal and professional lives of budding lawyers; law schools can’t cover everything. As with all other professions, the legal business is tough for beginners, but mentors can guide them through the rough parts and help them shine.

You need to understand this and appreciate the role that your mentor is playing in your professional life and realize that their contributions will be vital in making you a successful professional like them, someday. If you begin with appreciation, you’ll be in a much better position to get the most out of your meetings. Of course, you also need to show this appreciation to the mentor so that they feel that their efforts mean something to you and that you are willing to absorb as much information as possible.

The best way to do that is to be prepared well for every in-person meeting with your mentor. If you ask general and impersonal questions, they’ll feel that you’re just completing a formality – no one likes that. The quality of your questions will show your mentor just how eager you are and how much you want to learn, but you need to be prepared if you want to ask such questions. To prepare well, you’ll have to study hard, observe everything, even the small things, note the challenges that you face at the moment, and come up with a whole list of questions based on these experiences and observations.

Your list should cover everything, there are no good or bad questions, in the beginning, you just need as many entries as possible in your list. You can screen the list later on. Start with the general things, look up the important challenges you might come across when handling clients, preparing cases, dealing with the tough aspects of law, and so on. Move from general to specific situations so that you have a ton of different questions to ask in your next meetup.

Also, don’t forget your appointments with your mentor or be late for them – this goes without saying, but it is important to say so regardless. You need to show your mentor that you are eager for your meetups, and showing up late or missing your appointment goes against that. Be organized, color-code your calendars, set up reminders, and keep your meetings in your mind so that you never miss out on your chance to show your enthusiasm.

And, of course, before you show up, you need to show your mentor that you’ve done some work on your own as well, this shows initiative. After that, you can ask them all sorts of questions from your screened list. Plus, it would be a nice idea to insist on accompanying them to meet other professionals to observe how the legal business rolls.

Now that you’ve understood the basics of preparing for your meets, let’s move on to the part about your questions and analyze in detail the type of questions you should ask your mentor, and what kind of impact those questions will have on your learning experience.

The Best Types Of Questions To Ask Your Mentor At A Law Firm

As we’ve noted earlier on, the quality of your questions will show your mentor just how much you value your time with them, so be extra careful not to disappoint them. You don’t have to ask Einstein-level questions, but avoid the obvious ones – your questions need to be designed such that they get experience-based answers from your mentor. Just imagine how your mentor will respond to a particular question – does it stimulate an experience story in response, or can you hope to get some expert advice as an answer?

Of course, we’ve just begun scratching the surface.

Generally, there are four different types of questions you can ask, categorically speaking, and these categories encompass a ton of different questions.

Let’s review them one by one:

#1) Story-Based Questions

The first and most important type is a story-based question. These questions are both personal and will stimulate practical advice from your mentor. Everyone loves to talk about their experiences, especially their feel-proud moments, i.e. if they were confronted with some serious challenges they managed to overcome. This way, not only will you learn from their stories but also build a bond based on trust with your mentor.

The idea is both to get them to open up to them but also to learn from their success stories. Plus, you can relate to this stuff because everyone likes a story, especially something that motivates them to go on through the initial challenges of their professional field. However, you can’t go on with only such questions because they are only good for breaking the ice now and then, for more specific advice and insights, you may use situation-based questions.

Consider this question: “how did you manage to climb your way up to this position in the firm?” Firstly, it will prompt your mentor to share their experience with the firm. Secondly, you can relate to the answer because it will give you some guidelines on what you should aspire to do in the legal firm. Lastly, and most importantly, you’ll pick up on a ton of different ideas from the answer itself which will help you come up with more questions. The perfect ice breaker to unleash a barrage of discussion topics; plus, you’ll get to have frank conversations about your career goals.

Here are some examples of story-based questions to ask your mentor, not all at once though:

• Did you ever face failure in your professional journey in this law firm, and if yes, how did you manage to get back on your feet?
• Risks are scary, how did you learn to embrace them in the practice of law?
• Can you tell me about some recent failures or setbacks you faced, and how did you reverse them?
• Looking back five years in the past, are you where you thought you would be, and what made that possible?
• Did you ever feel, after landing a new position in the firm, that you were not completely qualified for the post, and if so, how did you move ahead?
• Reflecting on your past experiences, what do you feel you should have known when starting your legal practice with the firm, and how would that information have helped?
• What business skills are the most important but hardest to learn for both individual lawyers and those working with management in law firms?
• Did you ever work with a difficult client, if so, how bad were things, and how did you manage the situation?
• What is the single most important lesson you learned in your career as a legal professional, and how has that skill proven to be vital for your professional growth?
• How did you develop interpersonal skills to better handle clients and make them feel valued, safe, and at ease?

The important component of these questions is that they stimulate inspiring answers that can help you through a phase of your professional career. All of these questions are, in a way, personal, which means that you will get to know more about your mentor, besides the formal introduction. This way, you’ll be better aware of their strengths in the business and explore those areas even further. Just remember that the answers will be non-specific when compared to answers for specific queries, i.e. how to do something.

Let’s move on to the next type.

#2) Situation-Based Questions

Once you get the words flowing, you can truly get engaged in a meaningful conversation with specific, situation-based questions. The idea is to move from general to specific, and if you understand the basics of carrying a discussion forward, you won’t run out of ideas. It is best to pick up on bits from their answers to expand on that part of the discussion. Of course, that is not to say that you can’t come up with a list of situational questions yourself to ask spontaneously.

In either case, the idea is to learn about situations that either trouble you at the moment, did trouble you in the past, but you were unable to cope with them as effectively as you’d wanted to, or situations that you might find troubling in the future. Your mentor has gone through all that you are at the moment, or can at least relate to the situation, i.e. a legal issue. This means that if you plan on getting the most out of your talks, it would be best to learn from their experience in situations that are similar to yours.

Here are some examples of these questions:

• I tried to handle a delicate, challenging task last week, but I feel that I could’ve done a much better job, how could I have done a better job, or better yet, can you tell me how you would’ve handled things differently?
• Who do I need to align myself with in the law office management in this law firm business to succeed as a professional?
• Last day, my boss and I had a discussion, and they said that I need to develop a better professional strategy to progress in this business, how should I approach this problem?
• I feel a bit disturbed because my boss micromanages me all the time, I can manage things on my own, but I need to prove this to my boss, how do I do that?
• For professional growth, I need to be in touch with influencers and important professionals from all over, both from my firm and outside, how do I do that?
• How should I prepare myself for my upcoming performance review, how would you want to see one of your subordinates ready themselves in this regard?
• I am a bit divided between the professional options I have in front of me, how can I best choose which one is for me?
• How can stretch assignments help me further my career, what are the merits and cons, and would you go for it?

As noted earlier, these questions can be thought of beforehand, which would be more productive – it shows that you are aware of your professional challenges. However, if you’re a complete rookie and have not been too deep into the legal business, you can just pick up on topics to discuss from the answers to the story-based questions. Just be sure you stick to relevance when discussing these questions – one situation may feel more relevant at a point in time than the other.

#3) Questions About Self-Awareness

Self-awareness is the biggest driver of success in the professional landscape. This is perhaps the single most important thing you can look for in a professional environment, it gives you a sense of direction about what kind of professional you want to be. The basic idea is to get a mirror in front of you, so you see yourself the way others too – are you projecting the right vibes; is there something promising in you that others look at; are there any flaws that you could work on?

You only have something to gain – if your colleagues and superiors view you in a positive light, you’ll create a sense of confidence about yourself which will inspire you to be even better than how you are at the moment. Conversely, if there are things about you that others don’t care for or if you are projecting yourself in a less than ideal manner, you can improve yourself by knowing how you are being perceived by others.

Once again, you need to move from a general to a specific stance. You can start by asking questions like: “how do you think my colleagues and superiors look at me?” You need to see yourself in the mirror and your mentor will be the mirror, they’ll show you how you are being perceived by others. Based on their assessment, you can make things better. Ask for detailed feedback so that you can explore specific areas of improvement.

Here are some examples of questions you can ask in this regard which you can use to get some clues about the ways you can improve your perception:

• How do you think my personality fits into this organization, do people perceive me positively?
• What do you think are my strengths, and do I project them fine?
• How do you think my superiors perceive me?
• How do my colleagues and superiors talk about me in my absence?
• What do you think I can do to improve my perception in the eyes of other people?
• How can I project myself more confidently and positively for others?
• How do you think I come across when communicating with others, and how can I improve that perception?
• I send my immediate superior regular updates about my progress, does that make me come across as high-maintenance, and if so, how can I change that to appear more dedicated to my job?
• Can I do something to make my communication efforts more clear and concise?
• Last week I presented my ideas on what we could do to approach clients more effectively, how was my presentation, and what could I have done to make it better?

Through this self-awareness, you’ll be able to better assess yourself as a professional with strengths and weaknesses. The first step in addressing a professional issue is the acknowledgment that there is one, to begin with.

Explore your flaws because you have to kick them out.

#4) Skill-Building Questions

These are the most specific of all types of questions mentioned so far because in this case, you’re looking to improve some very specific professional areas about your personality. Communication, teamwork, leadership, professional expertise, professional conduct, core concepts, and so on – these are some of the many skill areas that you can work on. However, it is hard to know what areas you need to improve because this is something only an expert, via one-to-one coaching, can help you with; here are some examples:

• How can I better handle my clients?
• I want to ask for a pay raise based on my professional competence, can I role-play doing so with you?
• I think I need to improve the way I organize myself and manage my tasks, how do I do that?
• Sometimes I feel down and low in my routine, and I feel like it is important for me to re-energize myself when I am overworked, how do I do that?
• I have trouble with difficult conversations, can you recommend some resources for this?
• How can I deal with nervousness when dealing with a new client?
• I have been assigned to lead a group of my colleagues (personnel management) on a project, how can I do that most efficiently?
• What skill areas do I need to work on the most?

Bottom Line

In the end, your chance at success in creating a meaningful mentoring relationship will be determined by your commitment – if you are willing to make it work, things will come together. Communication is at the forefront of every interaction, and you need to understand how best to present yourself before your mentor, so they take you seriously and do all they can to help you grow professionally. Understanding the types and specifics of questions you can ask your mentor will matter a lot when it comes to presenting yourself, just be prepared, and the rest will work out itself.

Seeking practical advice from senior law firm attorneys is step one towards becoming promising professionals yourself, so make it count.