• Benny Reich

Mentoring 101.

Updated: Jan 25

Step by step product management mentoring.

In Mentoring Thinking I explained why it’s good to become a mentor. This time as a special tribute to Product League, a product management mentoring program run by volunteering product managers contributing to the community, I am giving tips on how to approach your mentoring. While I am referring mostly to product management mentoring, most of the advice is relevant for any type of mentoring.

Many of the below sections appeared first in Product League as a series of mini blogs.

What should you self-commit to, before mentoring? (and why!)

Appeared first in Product League Blog.

Being a mentor is not just a nice enhancement to your skills and activities on your CV. It is a commitment. You practically promise someone else that you are going to help them in both their career and self-development process.

Nevertheless, in our stressful and never-stopping domain of work, mentoring is a time and effort consuming process. In the end, both you (the mentor) and your mentee want to feel that you gained real value out of the experience.

The level of self-commitment depends tremendously on the type of mentorship you take upon yourself and how you frame it, both to yourself and to your mentee. In this post, we will take a deeper look at the different alternatives for mentoring framing and challenge ourselves to choose a mentoring frame/style that works to our needs.

Some categorize the experience into one of the following: ad-hoc mentorship, time framed mentorship, or goal-oriented mentorship:

Ad-hoc mentoring is when you provide your mentee with knowledge and advice on a non-obligatory basis, based on demand and interests with no clear schedule or agenda in mind. It may be a one-time encounter or a mentoring for life. The underlying assumption is that there is no commitment or any unspoken contract between the mentor and mentee. It looks more like a friendship. In such a mentorship setup it is usually less important to self-commit (it just happens by itself).

In both other types of mentorship, there is usually a more rigid setup between you and the mentee in which you agree to what you want to achieve. In such cases, it is better to ask yourself what are you willingly committing to before going into the process, communicate that commitment to your mentee and work out a plan that works for you both.

With a different portion of commitment and a higher degree of scheduling, we will find the other two types of mentorship:

Goal-oriented mentorship is when you start by defining an objective the mentee wants to achieve during the mentoring sessions. Once the objective is achieved, the sessions are usually concluded, or another objective can be agreed on.

Time framed mentorship is when there is an agreed period of time during which the sessions occur and after a certain amount of time, a new goal is set for the mentoring sessions. In such a situation, as you may want to achieve a few goals, the intensity of the sessions is very important.

Your self-commitment, the level of coherence of that commitment to your mentee, and your agreement on the terms would ensure a matching of expectations on both sides and will provide higher chances of fruitful discussions and a meaningful learnings experience.

Before diving into your mentoring adventure, I highly recommend to plan your commitment and set its values. Just like if it was a product! So what are your commitment’s KPIs?

  • Level of periodic engagement: Weekly, biweekly, monthly and for how long (half hour, hour).

  • Level of engagement aside from the meeting such as session preparation.

  • Your level of responsiveness. Through which platforms?

  • Type of engagement you are comfortable with: face to face, video conference, or both.

  • If you are meeting your mentee in person, where are your meetings going to happen? Both geographically and in terms of setting (office? cafe? home?).

  • What are you willing and allowed to share and discuss? Everyone must feel comfortable.

  • What would you like the outcome of the mentoring sessions to be? This is the time to set goals!

Read The Mentor Manifesto by David Cohen for additional inspiration.

How to approach your 1st mentoring session? (focus on what’s matter).

Appeared first in Product League Blog.

If I have to choose one “mentoring” advice to give you, it will be a very actionable one: If you want to be a good mentor, you have to start mentoring! Now.

Don’t delay setting the first session. Getting into a committed pace is very important to ensure you are both serious about the process and relationship. Don’t let the opportunity slip away and feel like an unwelcome burden, giving you a hard time balancing your life instead of nurturing it.

As in any other project, your first session creates the setup for the whole interaction.

The most important part is for both of you to get to know each other. Make sure the first session has the right casual but appropriate atmosphere and spend a reasonable amount of time on introducing yourselves.

Don’t make it only professional. Share a little of your personal life, your habits, and goals.

All of the above ensure that things are taken seriously and also help the discussion become both more professional and personal at the same time. It usually results in the mentee feeling more relaxed and willing to open up not only on the technical level but also on the emotional level.

The next important thing to tackle, before starting the journey, is for you and the mentee to set goals and objectives for your sessions together. Keep in mind that as I described in the last post — you don’t have to set your goals for the entire program and can choose to set different goals from time to time.

However, with no goals at all, it will be extremely hard for you to get somewhere (yes, I know, this is Product Management 101).

Here are the top 3 options for goal setting for PM mentorship:

  1. The mentee has some career goal he or she wants to achieve in the next year (e.g., moving from being a product manager to being a product management group leader). Try to break this big goal into small, ready to action items or topics you can work on in each session

  2. The mentee has some specific mid-term goals at work they want to do or achieve (e.g., initiate some new process at work). These will probably be action focused discussion-items. I will highly recommend for you to make a short list of those (preferably in the first two weeks of the mentorship program) and discuss each with each other. You, as a mentor, may find out that you find yourself related to some items more than others and can decide to focus on these subjects

  3. The mentee has no specific long-term or mid-term goal, and mostly want help in the day to day challenges. No worries!

Now it’s time for you guys to translate that daily product-manias into actionable discussion items you can base your meetings on.

Regardless of the goal, it is easier to tie the sessions to real-life problems and not to theoretic cases. Relating to real-life (preferably recent) issues, help guiding the mentee to challenge herself by asking the right questions. When the mentee asks too many theoretical questions, the session might easily slip into consulting instead of mentoring.

Last but not least, make sure to discuss your mutual commitments as mentioned above.

Once the primary goal is defined, and your commitments are clear, it’s easier to plan each session and make sure focus is maintained.

As we’ve proved before, mentoring is not so different from product management. Your primary role is to be the focus advocate and stir the discussions.

Face to Face vs remote mentoring

Appeared first in Product League Forum.

Mentoring (like interviews and management) is not just a methodological process, it’s also an emotional one.To give the best assistance to your mentee you need to be able to read between the lines and not just understand the technical, business or relationship challenges your mentee is bringing up, but also try to see how the things they bring up affect them emotionally.

The key to a breakthrough many times lies there.

I would recommend, if possible, to mentor face to face. Face to face mentoring is always better. It makes it easier to be there for your mentee when sitting in the same room in a relaxed (almost therapy like) environment.

It is harder to “crack it” when the mentor and mentee are not located in the same city and have a problem meeting face to face. Especially for us Israelis who are very informal (talking with our hands) people.

The challenges in remote mentoring are similar to any mentoring, but they are enhanced by the medium.While in a face to face mentoring you may easily get out of not preparing in advance by improvising on the go and reacting to body language and emotion, in a remote mentoring, the key for success is preparation on both sides. Otherwise, you get into awkward silences and meetings that end early and are not as effective as they could have been.

If remote mentoring is your only viable option, make sure to address the challenges properly (some of the advices below are good also for face to face meetings):

  • Keeping momentum is important. Make sure you have a meeting at least once a week or once a fortnight. Use video calls. If a video call is not an option, a phone call is also better than nothing.

  • Schedule a week in advance, so the “I am busy” excuse is not an option.

  • If for some reason the time becomes inconvenient, try to be flexible and find a new time in the same week.

  • Find a time in which each of you can be in a convenient environment. Make sure it is an environment and time in which a video call can be used conveniently without interruption.

  • Stay focused during the meeting. Keeping a focus on your mentee in a video call at all times is not easy. Sitting in front of a computer causes many of us to wander to other tasks in parallel. Treat it as if it is a customer call.

  • It helps to agree on the topic over emails in advance. This allows both you and your mentee to prepare and read ahead.

  • An email from the mentee covering his thoughts for the session beforehand can also help prepare both of you and allow to go deeper.

How to approach your last mentoring session.

For almost every mentoring a time may come when it ran its course. It may be because the time allocated for the mentoring is coming to an end, you have reached your goals, or sometimes you feel that the effectiveness has been exhausted.

Your last session is as important as your first session. Don’t make it a causal one. Plan for it and make it count. I would recommend covering at least 3 topics:

  • Key Takeaways. It is a good time to reflect on the things discussed and achieved during the mentorship sessions.

  • Retrospective. You always want to learn. A retrospective on your sessions and what each one of you takes from them is an excellent way to learn and improve.

  • What’s Next. It is a good opportunity to discuss future goals. Even though you will not be processing them together, it gives a feeling of “more” to the whole experience.

Analyze your mentoring experience

Learning from your experience is very important. You should analyze it both at the end of every session and also at the end of every period of mentoring.

You can do it by yourself, or you can also do it together with your mentee and try to get their feedback.

Some of the things you should ask yourself include:


  • Was I responsive?

  • Did I listen?

  • Was I committed?

  • Did I guide properly or tried to control?

  • Did I have enough empathy?


  • Was the mentee satisfied with the sessions?

  • Was the session valuable for the mentee?

  • Was the goal setup in the first session achieved?

Last but not least

Doing something outside your daily job to broaden your horizon is always good, and mentoring is one way out of many to do that.

Like everything else you may be doing, it is something that better be taken seriously and professionally. Whatever you do and how you do it, don’t forget to enjoy it and have fun along the way. Otherwise, it isn’t worth it.

Have Fun.

#productmanagement #mentoring #learning #softskills

Benny Reich