General Practice, Solo & Small Firm DivisionTechnology & Practice Guide


Zen and the Art of E-mentoring

By Martha A. Mills

I was the University of Minnesota Law School’s first e-mail mentor. The University initiated its e-mail mentoring program last year in an effort to link first year students with practicing attorneys, who could provide career advice; information about the legal profession; and assistance in navigating what many consider to be the hardest, most challenging year of law school. I was excited and honored to have been asked to inaugurate the program, particularly because I too had benefitted from such a mentorship a couple of years ago when I went back to school for an advanced degree in telecommunications.

My e-mentor was Pat. Pat and I could talk— really talk—about intellectual as well as personal matters. He always had a slightly different outlook on issues, that I found sometimes fascinating, usually helpful, and always interesting. I respected Pat a great deal and appreciated the way he challenged me to look at and expand myself, my abilities, my career, and my life, in ways I had not done before. Pat included me in his own life and concerns as well; he valued my opinions and even consulted me for advice on occasion. I expect the reason that Pat did this was because I returned his respect, his interest, and provided a differing viewpoint.

Pat and I communicated solely through e-mail for a little over a year before we even spoke to each other on the telephone. And it was not until some time later that we actually met in person. Of course, we got along splendidly. However, I still think our most satisfying and rewarding conversations took place by e-mail.

Positive memories of my own e-mentoring experience spurred me on as I embarked upon the challenge of initiating an e-mail relationship with my young mentee. My first message to him said simply:

I would be pleased to be whatever a mentor might be for you—a friend, sounding board, advisor, shoulder to cry on, encourager, resource for information, or whatever else may be useful. I tend to think that this e-mail mentoring may work much better than face-to-face where communications are more stilted and less frequently available. Let us prove it to the school—they need a few lessons in how well electronic communications work!!

My law student mentee and I started out by describing our backgrounds. He told me about his family, his travels, and his interest in international law. I told him about myself, my career, and my experience as a judge. We liked each other almost immediately. As the year wore on, in between our busy schedules and activities, we managed to communicate on a variety of topics, including the fact that we both celebrated Orthodox Easter; my opinion about a certain California death penalty case; his plans to go to Russia for the summer; and the behavior of Judge Ito during the OJ trial, to name a few. Some of our most recent discussions have concerned the firms that he is interested in interviewing with for second year summer employment. I offered to help him in his endeavors and wrote to people I knew at the firms in an effort to smooth his introduction.

As of the writing of this article, my mentee and I have not yet met in person. However, by the time this article is read (and hopefully enjoyed) by the readers of Technology and Practice Guide, we will have met and I am sure that our meeting will validate the impressions that we both have formed through our e-mail contact.

I f you are interested in becoming involved in an existing e-mentor program check with:

•your alma mater;

•the local law schools in your city or state; or

•your local bar associations—particularly their young lawyer sections.

The Value of E-mentoring

The most important benefit of the e-mentoring program offered by the University of Minnesota School of Law is that it provides a shoulder to cry on for first year students who seek advice, encouragement, or merely a sounding board to ask a “stupid” question. Furthermore, it offers an opportunity for students to communicate with practitioners who are actually doing what the students aspire to do, in a nonthreatening environment. In fact, not too long ago, my mentee confided to me that he thought it was “awesome” that as a first year law student, he was able to talk to someone of my “vast” experience.

Many schools and organizations have instituted mentoring programs (generally of the personal meeting/telephone call variety). However successful some of these programs may be, I believe that most truly effective mentor relationships simply happen; they are not prearranged. Often the mentor is not even conscious of serving in that role and the mentee is not aware of it either until much later. E-mentoring can be a powerful tool in making a prearranged mentorship work and can be a valuable component of any more conventional mentor/mentee relationship, whether between student and professional, associate and partner, or any other combination. E-mail can be more conducive to getting to know and feeling comfortable with the other person, than face-to-face contact. This can be particularly true when an inexperienced mentee is paired with a very senior level person, as it lessens the intimidation factor considerably.

Also, unless you are told or have ESP, you will not know whether the person you are communicating with is male or female, of another race, or disabled in some way. This allows you to really get to know the person without being prejudiced by irrelevant biases or snap judgments. E-mail engenders a freedom of communication that tends to be more relaxed, friendly, and personal in nature, which is conducive to frank and open discussion between mentor and mentee.


Mentoring via e-mail offers considerable flexibility that traditional mentoring does not, by allowing people to communicate across barriers of time and geography. It facilitates communication between the parties to the “e-mentoriage” despite their hectic and many times incompatible schedules, which gives it practical advantages over real-time communications. It is asynchronous, so that one has access to it at any hour of the day or night. One person can go online to send or receive messages at a convenient time for that person, and the other person can do the same at his or her own convenience. And despite the difference in time, they are still able to communicate with each other. For instance, my mentee may have a problem that he wants my advice in resolving. The only problem is that it is 2:00 a.m. in the morning. Although he would never call me at that hour for advice (well, I hope not anyway!), he can unburden himself by jotting down his problem in an e-mail message and sending it to me at that time, secure in the knowledge that I will respond in due course.

In general, e-mail allows us to be thoughtful in our interaction, as we have more time to think in wording our communiques.

E-mail can be sent to and received from any place on earth, so long as there is an accessible computer with a modem and a telephone line. Actually, wireless e-mail is becoming more readily available, so the need for a phone line may eventually become moot. The ability to send and receive from anywhere, and the advantage of being able to do so at your convenience, make e-mail unparalleled in usefulness.

E-mail is the ideal way to provide friendship or support to someone whose contacts with the rest of the organization are, by reason of geography, work schedules, type of work, or condition of health, irregular. Perhaps a young lawyer in a firm’s office in Topeka is working in a specialty area and is teamed up with an attorney in the firm’s Los Angeles office who works in the same area. Or a part-time lawyer, a home-office lawyer, or a road warrior, is teamed up via e-mail with a full-time employee in the office. Or someone with the inability to keep regular office hours due to health or disability is partnered with someone who can.

Add to all these advantages the expanding capabilities of e-mail. Not only can I send my mentee an e-mail message, but now I can embed web addresses, film clips, photographs, sound clips, and more, into my message. These promises of enhanced communication add even greater attractiveness to e-mail.


If there is one downside to using e-mail as the primary form of communication, it is the inability to take advantage of visual cues to gauge the meaning of the other person’s comments. Therefore, it is helpful to use emoticons such as “(smile)” or “:-)” to designate when you are just kidding or being facetious. Use of these simple, and sometimes very clever, emoticons can go a long way toward preventing misunderstandings that can damage the mentor/mentee relationship.


The University of Minnesota is currently gathering data on the overall success of its e-mentoring program. Personally, my experience as an e-mentor has been a very rewarding and enriching one. I believe that my mentee and I have established a mutually beneficial relationship in which we are both comfortable in sharing our aspirations, concerns, and opposing viewpoints. If our e-mentoring test case is representative of the law school’s program as a whole, I would say that it has been a resounding success.

Martha A. Mills is a former judge of the Cook County Circuit Court in Illinois. She is currently a partner with the law firm of Bellows and Bellows in Chicago. Ms. Mills can be reached at

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