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The Art of Mentoring – Tips for the Aspiring Mentor

By Julian Mercer

I have observed over the years that young professionals frequently express an interest in having mentors, and that many experienced professionals are also eager to be mentors. But in practice, it is often difficult to connect the supply and demand or to sustain those connections over time. Conversations with frustrated mentors and mentees have highlighted several reasons why making those direct connections are hard, and why disconnects happen.

First of all, there are basic demographic issues. Many volunteer mentors are nearing the end of their careers or have retired and have the time and inclination to mentor as a way of passing on their knowledge to the next generation. It’s a noble aspiration, and my observation is not meant to discourage older professionals from volunteering as mentors. But the mentor’s experience may be at a higher level of the business, and based on a different skillset, business environment or culture with different problems than the younger worker is currently dealing with. What I hear from many prospective mentees is that they would prefer a younger, but successful mentor, who is more familiar with the challenges they are facing at that stage of their career and level of responsibility.

Another problem is that many aspiring mentors possess a wealth of life experience and practical know-how that they are motivated to pass along in order to “give back.” They may be motivated by the mentorship they received as young professionals, and because they have the time and are looking for productive ways to use it. If this is their first experience with mentoring, then this desire often manifests as what I like to call the “Teacher Syndrome.”

Most young professionals are happy to have left the classroom and aren’t looking for mentors to be teachers. They don’t want to be lectured, even if they are polite listeners. They tend to disengage if a mentor tries to solve their problems for them by telling them the “right” way to handle it.

What mentees are looking for is someone who will listen to their problems and ask questions, or give them useful bits of information that encourages them to look at their current challenges from a different angle. The types of questions that help them identify and assess their options, formulate their own solutions, and develop a personal strategy on how best to proceed. If you ask the right questions and resist the urge to tell them the answer, they will come up with a solution that will give them valuable insights and experience — even it if fails. That type of mentoring approach is empowering because the mentee feels like they created and own the solution, which builds confidence and encourages initiative.

A third area of disconnect is that many young professionals who want mentors are really looking for individuals who can help open doors for them through their business contacts, and help them up the rungs of the career ladder into positions of greater responsibility and higher compensation. That is fine, and a good mentor should be willing (within reason) to make use of their contacts and to make calls to help advance the careers of their mentees. But the reality is that many would-be mentors no longer have those types of contacts to offer.

A fourth area of disconnect is that many mentees are not looking for a traditional mentorship relationship, but are actively observing and emulating the behaviors of the role models they see around them. This type of passive “mentorship” occurs frequently without any form of direct communication. Young professionals naturally will look at how successful colleagues handle problems, communicate and practice leadership. They may draw lessons and take inspiration by observing several “mentors,” who may be unaware that they’re providing that type of support and guidance.

So, for the experienced professional interested in becoming a mentor, what are the skills and behaviors that you can learn and practice to become an effective mentor? Here are nine aspects of successful mentorship that I have observed:

1) Always Start with A Conversation on Goals and Expectations

A good mentoring relationship starts with an honest discussion about what each party hopes to get out of the experience. It is also where both parties can set boundaries and discuss logistics on how, when, and where mentoring will occur.

By understanding and honoring each other’s boundaries, both the mentor and mentee can maintain the mutual respect necessary to maintain the relationship over time. It is also the first opportunity to learn more about the mentee’s challenges, goals, desires, and feelings so that you can assess how to best engage, encourage and support them.

2) Stick to Relevant Knowledge or Qualifications

A good mentor has specific knowledge and practical experience that they can share that is relevant to the needs of the mentee. If the prospective mentee needs help that you don’t feel qualified to give, where you lack experience, or haven’t followed your own advice, then it’s often best to decline the invitation to mentor. At a minimum, avoid giving advice on topics you aren’t qualified to speak to.

3) Listen and Ask Questions

The quickest way to shut down communication between you and your mentee is to talk and not listen. Mentees are often looking to a mentor for affirmation and may value the opportunity to vent as much as they might appreciate getting advice on a solution to their problems. They may just want to be heard, because their colleagues or managers are not open to their suggestions.

Once they’ve said what they need to say, then asking questions is a way that you can communicate that you were listening. The questions could be as simple as “how did that make you feel?” or “what do you think you should do next?” or “do you have any ideas for how to handle the situation?” And if your mentee feels too insecure to ask you for advice, you can use questions to draw them out, which will help earn their trust and build their confidence.

4) Hold Opinions Until Asked

Advice is basically a form of opinion, informed by knowledge or personal experience. Don’t offer opinions unless asked or invited to share them. And when you share an opinion, make sure to explain the reasons why you arrived at that conclusion, including the experience(s) that informed your view. Understanding your rationales and the context that gave rise to them will enable the mentee to assess your opinion and its relevance to their needs. Like a picture, advice offered in the form a real-life anecdote is worth a thousand words, in terms of aiding the listener’s comprehension and understanding.

With respect to career-related mentorship, your mentee should be allowed to make their own decisions, especially about their career path. Your job is to understand their aspirations and to help them identify options and learn how to see opportunities. Give them useful information about options and things to consider, but don’t inject your own preferences, desires or opinions with respect to their choices.

5) Make Sure Your Criticism is Constructive

A good mentor will be called upon from time to time to give constructive criticism. Good practitioners of constructive criticism know to be specific, to be non-judgmental and non-emotional, to eliminate bias, and to invite the recipient’s feedback. Just as in personnel management, it’s important to focus on the issue and not the person.

Good criticism is truthful but tactful, and designed to help your mentee achieve success when the next situation or opportunity rolls around. Criticism that comes across as judgmental, hostile or condescending will undermine trust and can shut down the mentoring relationship. It can put your mentee on the defensive and make them unreceptive to advice or diminish their confidence in themselves.

There are many ways to deliver constructive criticism, one of which is by sharing a story about a similar mistake you made and what you learned from it. Use of humor and self-deprecation to deliver the message is also a useful tactic. It also helps to leaven the bad news with good news by pointing out something positive. If there are no positives in the situation, then you can remind them of the progress they’ve made and previous achievements as a way of encouraging them to persevere.

6) Practice Empathy and Patience

Empathy and patience are perhaps the two most important attributes of a good mentor. Mentees need to know that you care and that you are not there to judge. If they’re having a bad day and need some positive feedback, then empathy helps you focus on meeting that need instead of using the cause of their bad day as a teaching device.

Empathy and patience are skills that can be learned and practiced. The key attributes are thoughtful listening; putting yourself in the other’s shoes; avoiding emotional reactions; using various techniques to manage difficult conversations; showing curiosity and a willingness to step outside your comfort zone; and being cognizant of any personal biases that could lead to judgmental responses or put the mentee in a more negative frame of mind.

7) Know When to Defer

Just because you may “know better” doesn’t change the fact that your mentee needs the experience of making decisions for themselves. At some point, they will be called upon to find creative solutions to a problem while under great pressure and while wrestling with competing demands on their time and attention. That kind of skill only comes with experience and practice. A good mentor knows when to step back and defer to the mentee’s own process, giving them the chance to apply what they’ve learned and to learn from their successes and failures.

When you’re mentoring a work subordinate, deferring is also about giving them responsibility, trusting them to make their own decisions, and having the patience to let them learn from their mistakes. Giving them that kind of opportunity demonstrates trust and builds loyalty.

8) Practice What You Preach

Practicing what you preach is ultimately about following your own advice and keeping trust with your mentee. That consistency helps validate your advice. Your mentee can also learn a lot by simply observing and assessing how you put your advice into action.

If you share a workplace, they will also learn from how you handle responsibility, how you behave toward and interact with others, how you deal with adversity, and how you react to success. They can learn the importance of sharing credit to motivate the team, and how to give constructive criticism from the criticism you give to your colleagues and direct reports. If you are modest about your success, show humility and empathy to colleagues, and are calm under pressure, they will learn to react in the same way. If you accept responsibility for mistakes and fix them, they will be encouraged to do the same. They’ll learn how to build teams, manage processes, successfully pitch an idea, and overcome bureaucratic hurdles by observing your successes and failures doing the same. And if you are an effective leader, you will communicate leadership skills almost by osmosis.

9) Keep Confidences

A strong mentor-mentee relationship may evolve beyond workplace issues or professional career choices into the realm of sensitive personal issues related to finances, relationships or personal behaviors. If you are going to allow those types of issues within the boundaries of your mentor-mentee relationship, then it is critical that you keep those confidences. Bad advice or a breach of confidence on a sensitive personal matter can destroy trust and end the relationship.

Closing Note

This was a long read, and I hope you found the time invested useful. Mentoring can be a very rewarding experience and a great way to “give back” and honor those who were your mentors. It can also be frustrating and may require patience in order to see a payoff to your efforts. There are no perfect mentors, and you can learn from your mistakes, get feedback from your mentee, and adapt as you go. If you hone these mentoring skills, you are more likely to have a successful and satisfying mentoring experience. And one day, you may have the distinct pleasure of having a former mentee credit you for their success and follow in your mentoring footsteps.


Julian Mercer

Julian Mercer is a retired executive, with more than 30 years’ experience in the technology sector as a leader, manager, consultant, and teacher.

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