The Mentoring Dilemma at Busy Law Firms

“I‘m supposed to talk with you about why I‘m not performing well.“

I could tell by her voice over the phone that she was not happy about this. Kelly‘s law firm asked her to contact me, an executive coach, to learn how to improve her game. She was a fifth year doing transactional work at a large New York firm.


“What do you think is the problem?“ I asked her.

“It‘s not what they think,“ she said irritably. “They think I am not performing at the level of a fifth year, that I need to be more organized and use better judgment, and stop procrastinating.“

“And what do you think is going on here?“ I asked.

“I think they are not mentoring me enough. They are not giving me the support I need to do the job well.“

We discussed her situation in more detail.

Kelly had begun her career at this firm as a litigation associate, but after a year she had requested a move to the transactional group where she felt more comfortable with the role and more interested in the work. She made that transition without losing any seniority, but she felt under pressure to perform at the level of a second year even though she was more appropriately a first year associate. Nonetheless, she worked hard and was gaining confidence at that point in her career, she told me.

However, the transactional group experienced a slowdown in business. Kelly was asked to return to the litigation group to help out doing discovery on a big case, or risk being let go. She went back to the litigation group with reluctance, hoping to return to the transactional group as soon as possible.

After the litigation matter settled, Kelly requested and obtained a return to the transactional group. When she returned to that group, however, there were fewer attorneys in the group. A year had gone by. All of the junior partners had been let go or had left of their own accord. Partners were doing the work that had been relegated to junior partners in the past. Consequently, the partners were extremely busy.

“And a lot more crabby,“ Kelly assured me.

Kelly returned to the group as a fourth year associate. She was also the most senior associate remaining in the group.

She struggled to get up to speed. Faced with a difficult question, or an instrument she did not recognize, or the need to make a crucial judgment call, she would ask one of her two partners for guidance. Very often they reacted to her requests with annoyance, telling her to use her own best judgment. But when she made a mistake after doing just that, the partners expressed their frustration with her.

Her reviews suffered because she was seen as inappropriately unsure of herself.

Understandably, after receiving this feedback, Kelly hesitated to ask for additional help from these two partners, for whom she did most of her work. She tried to get assistance from another partner in the same practice group, but he too was very busy.

Her reviews continued to be negative. Her partners now faulted her for procrastination and a slow turn-around time.

“What do they expect?“ she said. “When I get stuck I have no one to turn to for help. So I just sit here unable to figure out what to do. I feel sort of frozen. When I try to make a decision, I just don‘t have enough information to come up with a solution.“

Kelly‘s dilemma is not an isolated occurrence. With an increasing focus on managing costs, I am seeing many lawyers with similar problems. Some law firms have scrambled to keep associates, moving them into busier practice areas, while reducing the ranks of junior partners. Firms have made these strategic shifts to ramp up productivity and preserve senior partners. Kelly and others like her get into a Catch-22 situation. In her case, she could ask for help and risk being labeled as lacking judgment, or she could avoid asking for help but risk being labeled as a procrastinator. The underlying problem is that she needs more training and education to function well as an associate at her designated level.

These days more than ever before, busy partners want associates who will do their jobs without needing what partners think of as “hand holding“ and what associates think of as “mentoring“.

What are Kelly‘s options?

  1. She could try to find a partner, junior partner, more senior associate, or even a paralegal who would be willing to teach her.
  2. She could try to formulate one or two approaches based on what she does know, and request assistance from the partners who assigned the work when she is able to present more well-developed ideas or strategies. This would show the partners that she is capable of advanced legal thinking.
  3. She could try to find a mentor/teacher outside of the firm.
  4. She could ask to be removed from the ranks of the fourth years and “demoted“ to a third year status. (This approach would have been better at the time she moved back to the transactional group to keep the pressure down, but she did not anticipate this problem.)

Kelly‘s dilemma will probably require that she try to find a tutor/mentor/teacher on her own. She can try her law school professors. At least she could start there. Perhaps a recently retired attorney who practiced the same kind of law would be able to help her. She needs a sounding board for her questions and help developing better judgment. This approach has worked for some of my clients with similar problems.

Large law firms would do well to consider an internship system similar to the medical profession where new graduates could learn the basics, ask basic questions of their mentors and teachers, and gain experience without the threat of a negative review.

Get Unstuck from a Low-level Job

Are you stuck in a low paying job? Are you stuck in a job that does not match your need for challenge and development? If so, what can you do to move on?

stuck in a job

When the recession hit in 2009 and in the years that followed, new graduates, full of hope but burdened by debt, entered a job market that offered far fewer jobs than before. When jobs are scarce, people settle for jobs they may not want because they have to pay the bills. They take what they can get. Once in such a job, it can be hard to get out. This is also true of a career path. The path you start out on tends to be the one you stay on unless you affirmatively do something to change your career direction.

What strategies could help you?

Know What You Need

Remember to do your personal assessment first.

  1. What are your strong aptitudes or natural talents?
  2. What are your strong interests in terms of content areas and areas of frequent thought that are enjoyable for you? Are you a people person who loves to talk and connect with others? Are you more intensely interested in video games or problem solving? Do you want to work with your hands and see a finished product?
  3. What do you need in terms of a lifestyle? What amount of money you need to feel secure? What kind of work/life balance do you want?
  4. What do you need in terms of workplace culture?
  5. Knowing these things about yourself, where is the match likely to be good for you in the world of work? Talk with people doing the work you think you want to do and ask them open-ended questions to learn more.
  6. Where are the jobs? What fields are short-handed and looking for help? Often these are the rapidly growing fields. Often you can find them by looking at postings on sites like The Muse, Indeed, and others.

If you do your self-assessment work first, you will be headed in the right direction. My book, Job Quest: How to Become the Insider Who Gets Hired can help you to do this assessment work.

Explore the Value of New Skills and Education

Skills acquisition and a different or a more niched educational degree or certification can often help to reboot a career direction. I know that might mean more debt, and some people cannot afford to take more classes. If you have high student loan debt, going back to school online may be the only feasible option. When it comes to an online reboot of your skills, there are some fields that will accept such credentials, but others that will remain uncertain about the level of expertise you have gained. Wariness about online education is likely to dissipate over time, especially as market demand rises, but it is something to ask about and think about before you spend money and time taking online courses. How will your online education be viewed by a potential employer? Do a cost/benefit analysis.

It might be worth it to spend the money to go to school at an institution that is respected by and closely connected with the industry you want to join. Brick and mortar schools or training camps offer opportunities for creating relationships with professors and students as well as alumni and industry providers. These relationships can be priceless when it comes to finding a good job.

We are seeing good jobs evolve out of the tech revolution; jobs are plentiful for people with the right skillset. Many of these jobs are in new fields such as digital marketing, social media, software engineering, coding, web design, and much more. There are new kinds of institutions that train people for these new career directions and are also designed to open doors to jobs requiring the kinds of skills people need in the 21st century.

One terrific example is the Startup Institute located in Chicago, Boston, and New York. The Startup Institute offers an intense eight week course where you can learn new skills and network with people in the industry. There are also less expensive part-time course options at the Startup Institute where you can learn specific skills such as Javascript or web design. According to their website, 90% of their graduates get jobs in the start-up world after graduating. Their intense course offers web design, web development, tech marketing, sales and account management, introduction to data science, Ruby, and more. Their website says that although the experience “begins as immersion learning with a cohort of strangers – it ends as a network of mentors, entrepreneurs, practitioners and peers that you take with you for the rest of your career.”

That might sound overblown, but I personally know two people who went to the Startup Institute and landed terrific jobs after they finished. The website tag line has proven to be accurate for them.

Startup Institute is not the only option out there. See what you can find.

Don’t let yourself get stuck in a job with no future. Once you know where you want to go next in your career, explore new on-ramps to jobs by investigating educational institutes, boot camps, or local community colleges. Be sure to find some alumni to talk with to be certain that the program is worth the money you will spend to re-direct your career. But once you have a firm basis for trusting the program, take the leap and reboot your career direction. You will be glad you did!