Mastering Mentoring 7 How Are We Doing

A Mentoring relationship is intended to be satisfying and mutually advantageous to both parties, so both people feel they are doing something highly useful. 

I think it is a good idea to check in on how things are going occasionally, but not so often it becomes a burden.

How Are We Doing

Plan to initiate a discussion of how the relationship is progressing. Have both parties describe what is going well and also any things that are getting in the way.  Be as candid as possible in these discussions, because this is how you can manage the relationship for optimal benefit in both directions.

Don’t settle for someone saying “things are going fine,” and leave it at that.  Ask more probing questions like:

  • What do you want to work on?
  • Where do you need support?
  • Do you have the resources you need?

Feel free to make up your own questions based on the unique relationship you have with the other person. Just come to an agreement that this is an informal process you can use to maximize the benefit.

Working this reflection into your routine will help keep the relationship fresh and growing for both people, but there is a precaution to address.


The key point to remember is to not let the process itself become a burden or a barrier to trust.  When the discussions of how we are doing become the main event, then you have gone too far.  I suggest if you are meeting in person or remotely, on a weekly basis, the frequency for this self-evaluation should be about every 2-3 months, but you get to choose the right frequency for you.

These relationships are multi-leveled. They involve specific skills, styles, insights, emotional intelligence, leadership, team building, personal development, and a host of specific topics depending on the people involved.

Each person should understand that it is safe to speak up if something isn’t working.

Keeping any mentor relationship fresh and useful for both parties requires some introspection. The trick is to find the right pattern and timing for these evaluations. It is a matter of personal preference and style. 

Bob Whipple, MBA, CPTD, is a consultant, trainer, speaker, and author in the areas of leadership and trust.  He is the author of: The Trust Factor: Advanced Leadership for Professionals, Understanding E-Body Language: Building Trust Online, Leading with Trust is Like Sailing Downwind, and Trust in Transition: Navigating Organizational Change.  Bob has many years as a senior executive with a Fortune 500 Company and with non-profit organizations. 

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