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Making an Ongoing Mentoring Relationship Stronger and More Productive
by Dan Pinnington
August 2004

Every mentoring relationship must find its own equilibrium and path. As time passes the partners will get to know each other, and a stronger personal relationship will develop.

As the relationship progresses, there are several things that mentor and mentee can to do make it work better. Effective communication and candid feedback are key. Both partners should try to ensure time is used as effectively and efficiently as possible. And, both mentor and mentee should monitor the learning process and progress, to ensure that the mentee’s learning goals are going to be reached.

The Art of Positive Feedback

One of the most important aspects of a mentoring relationship is how the mentor provides advice and feedback to the mentee, and how the mentee responds to that communication.

Giving feedback in a positive and constructive way is often difficult for mentors. At the same time, receiving that feedback without getting defensive is often difficult for mentees. To ensure it is well received, feedback should be thoughtful, specific, timely, candid, and constructive. When considering how to frame communication with a mentee, focus on the mentor’s key role: to nurture the mentee’s growth by facilitating an accepting, open and affirming learning atmosphere.

For example, when asked a question, avoid the temptation to instantly offer an answer. Instead, work at listening to the question and understanding the issue with which the mentee is struggling.

Then challenge the mentee to think the question through to a solution. Using open-ended questions that start with “how” or “what” often help direct the mentee to the answer. This technique will help the mentee develop the ability to critically think through problems and arrive at a solution on their own.

Finally, celebrate the successes, and don’t shy away from talking about the failures, and what can be learned from them. This will help the learning process and build the mentee’s confidence. With patience and time, the partners should develop a good rapport and become more comfortable with openly and freely conversing with each other.

Overcoming Obstacles

Like all relationships, mentoring comes with its share of unanticipated obstacles. Some will be under the control of the mentor or mentee, others will be external to both. Some may even result in the termination of the relationship.

The most common obstacles are:

  • the mentee wants too much time;
  • the mentee needs too much help;
  • the mentee seeks help on personal or other issues that are outside the agreed upon boundaries for the relationship;
  • the mentor is too busy or is inaccessible; or
  • other unforeseen or unexpected circumstances affect the ability of one of the partners to participate in the relationship as originally agreed.

The key to overcoming obstacles is to make sure both mentee and mentor expect them, and are prepared to promptly and properly deal with them. A partner who is upset or struggling with some aspect of the relationship should be candid with the other partner. The partners must be prepared to discuss the nature of any problem, why it is an obstacle, and then work together to resolve the issue. If the problems continue, the relationship should end.

Making Efficient Use of Time

A mentoring relationship will involve less time if the partners effectively manage the time they have. To accomplish this, try the following:

  • Schedule meetings in advance.
  • Be serious and diligent about scheduling and keeping appointments and returning e-mails and phone calls.
  • The quality of time spent together is more important than the quantity of time spent together. Do not multitask at mentoring meetings; both partners should focus solely on the issues at hand.
  • Maximize the time spent together by fully preparing for any discussions or meetings.
  • If appropriate, start each session or discussion with a progress review or update so as to focus the session in on the critical issues.
  • If appropriate, book a follow-up session at the conclusion of a meeting or discussion.
  • Monitor the time that is being spent on mentoring and look for opportunities to more effectively or efficiently use that time.

If changes occur that make existing time commitments a problem, don’t automatically abandon the relationship. Explore options for maintaining the relationship. Take a timeout if necessary, and, if possible, reconsider the time commitments so that they work for both partners.

Evaluate The Relationship as it Progresses

Once underway, most mentoring relationships require little intervention. To improve the relationship, mentor and mentee should consider meeting at some agreed interval to evaluate how things are progressing.

Ideally the timing of these meetings should be set at the start of the relationship. In the first year, frequent meetings—perhaps every quarter—are likely necessary to help fine-tune the relationship and address minor unanticipated difficulties. Once things are running smoothly, meeting every six months or so is likely sufficient. Of course, unanticipated difficulties would necessitate a meeting.

In preparing for these meetings mentor and mentee should ask themselves the following questions:

  • Are we on track to reach the goals of our mentoring relationship?
  • What do I think about my mentor/mentee?
  • What is working well, and why?
  • What could be working better?
  • What changes can be made to make things work better?
  • What are we spending too much time on?
  • What are we spending too little time on?
  • How well are we communicating?
  • Is there anything we can do improve our communications?
  • Is there anything we can to do more effectively use our time?
  • Are there any other changes we can make to improve the relationship?

The mentee, who is the primary beneficiary in the mentoring relationship, should be proactive in making sure that this review process occurs. Evaluating the relationship’s progress reminds both partners of its goals, and helps them focus on how to improve the relationship going forward.

A formal review and clear end to a mentoring relationship can make it a more positive learning experience for both mentor and mentee. This is the case regardless if a mentoring relationship is ending because its goals have been reached, if it has run out of steam, or has to be terminated due to other unforeseen circumstances.

The end should be seen as an opportunity to review what did and didn’t work in the relationship, and more importantly, to reflect on the results, so that every lesson that can be learned from the relationship is recognized. Both partners should celebrate its successes, acknowledge its failures, and conclude the relationship with positive feelings. A small token of appreciation from mentee to mentor also may be appropriate.

Partners who are interested in continuing to work together could use this formal ending as a spring board for new discussions aimed at setting new goals for a new mentoring relationship.

If the relationship is being dissolved, the mentor may be willing to continue acting as a resource to the mentee, albeit on a less frequent and more informal way. In many cases, the partners opt to stay in touch after the relationship is concluded.

And to bring the process full circle, mentees should consider passing on the knowledge and skills they gained by entering into a new mentoring relationship – as a mentor.

Ideally, working with a mentor should be one part of an overall career map or plan. If you are a sole practitioner or a member of a small firm, you will have a great deal of control over your destiny. If you are a member of a medium or larger firm, the firm will likely play a larger part in setting your goals and destiny. In either case, it is important that you assume the responsibility
for planning and mapping out your future.

Consider your career in the larger context of your life. Step back and take a look at the bigger picture. What is most important to you? Identify the things that will generate your greatest interest, enthusiasm and energy. This will help you to identify a career that will be personally satisfying to you. Personal satisfaction is important to happiness and success, both inside and outside of your legal career.

You should develop a career map and action plan that is goal oriented. Where are you today? Where do you want to get to? What do you have to do to get there? Set specific goals, and list the steps necessary to reach these goals. Next work to implement this plan with a detailed time table and to-do list. Discuss your plans with your mentor, and discuss ideas on
how you can work together to attain these goals.

Identify your strengths and weaknesses. Look for opportunities that let you leverage your strengths. Take steps to increase your skills in weak areas. This can be done through continuing legal education, workshops or other skill enhancing activities.

As you proceed with the execution of your plan, review your goals and evaluate your progress. Update and adjust your plans as required. Again, discuss and review your progress with your mentor.

Mentoring programs are coming back into vogue at law firms. The benefits of having a formal firm mentoring program include the following:

Faster integration of associates into a law firm: Participating in a mentoring program will help associates learn a firm’s polices and procedures, and get acquainted with lawyers and staff.

A clear road map of expectations for practice development: A mentoring program will give an associate a road map of how they should be progressing, and a clear understanding of what is expected from a practice development point of view.

Associates will have a broader perspective: Associates who are encouraged to participate at different stages of a variety of different matters will have a better understanding of the practice of law.

Although law firm mentoring programs vary in their formality and complexity, certain steps are critical to creating a successful mentoring program, and a firm where mentoring is part of the firm culture.

The 1996 Report of the Professionalism Committee produced by the Legal Education and Admissions to the Bar Section of the American Bar Association contains an excellent model mentoring policy. It contains extensive annotations and would serve as an excellent precedent for a firm implementing a mentoring program.

This is an excerpt from the Managing a Mentoring Relationship booklet, published by the Lawyers' Professional Indemnity Company.

Dan Pinnington ( works for the Lawyers' Professional Indemnity Company ( to help the 20,000 practising lawyers in Ontario avoid malpractice claims. He speaks and writes frequently on a variety of risk management and legal technology topics. Through practicePRO ( he provides Ontario lawyers with practical how-to resources aimed at helping them succeed in the practice of law.