Seven Deadly Sins of Mentoring

There is much more to a good mentoring program than simply pairing an experienced manager with a future leader. Here are our seven deadly sins of mentoring, which have the ability to turn any well intentioned mentor/mentee relationship into little more than an occasional coffee and chat between colleagues.


In most organisations which set up a mentoring program, the mentors are picked from a group of volunteer or ‘volunteered’ senior managers or experienced managers. They are given little instruction on what it means to be a mentor and no appraisal of their mentoring skills. They remain largely ignorant of what skills they need to improve to be an effective mentor and of what a genuine mentoring process looks like, sounds like and what it should deliver. The most common error in mentoring is selecting poor mentors and not up-skilling those who have the potential to be good mentors.


Directive coaching is a legitimate part of the arsenal of a mentor. However, when that is the only method a mentor uses or it forms the dominant method, the mentee’s ability to grow and be empowered to confront issues which trouble them and make good decisions on their own is severely diminished.

A good mentor will encourage a mentee to research the topics of interest, perhaps directing them where to find help, discuss what they found and think about the topic now, perhaps share an anecdote of their own related to the topic, ask facilitative questions of the mentee and use non-directional coaching techniques supported by an occasional application of directional coaching.


Another key weakness in the setup of an organisational mentoring system is the notion that mentors and mentees should meet regularly, setting up a time in the diary. While this well intentioned in that it strives to ensure there is regular discussion, it leads to the mentee and the mentor not discussing the mentee’s needs at the time of need.

To be a mentor means you have to be available at the time of the mentee’s need. Having no conversation for a month or even a week leads to disconnects between the mentee’s needs and thoughts and actions that can render the mentor/mentee relationship virtually useless.

Mentors need to spend time with their mentees, especially in the first weeks and months building a relationship. The mentor needs to coax from the mentee and share with the mentee experiences that demonstrate the values that each have. The mentor needs to build rapport to build trust. Mentoring does not exist in a trust vacuum.


Mentees at times will not want to face some of their challenges, preferring to talk about them in a reactive negative manner rather than determining what they can control and proactively taking steps to gain that control.

Mentors that acquiesce to a mentee’s desire to not tackle any issues which may be preventing them from progressing as a person do the mentee a disservice. That is not to say that discretion should not be used with topics which are particularly sensitive for the mentee. A mentor is not meant to be a psychologist and does more harm than good when attempting to be one.

However, it is incumbent on the mentor to help the mentee face their challenges and work through them as if eating that ubiquitous elephant, one bite at a time. The key skill here is questioning skills. Being able to ask situation questions, problem questions, consequence questions and benefit questions (of a changed behaviour or gaining of a new skill) helps mentees progress from not wanting to talk about topics to finding a way to see the benefits of confronting the challenge.


Anecdotes about life-experiences pertinent to the topics of interest to the mentee are good ways to build relationships and have the mentee perceive that the mentor can offer some practical advice built from experience. However, over doing the anecdotes to the point where it becomes in the mentee’s eyes ‘yet another story about my glorious career’ spells the death knell of a mentor/mentee relationship.

While it is important for the mentor to benefit from the relationship, a mentoring program is about the mentee and their needs and wants not the mentor’s.

Another common fault is when mentors cannot understand why a mentee is unable or unwilling to tackle a challenge that the mentor themselves tackled and conquered easily. Mentors need to park the ego and ask questions of the mentee to understand what lies behind the reticence and facilitate their journey rather than saying, ”It’s easy, I did it!”


Whilst it is good to establish the context of a topic by speaking about general principles and getting the mentee to research the principles of a topic, at some stage the discussion between the mentee and the mentor must reach the specifics of the topic.

Talking in generalities seems to be a modern disease built on the explosion of self-help books and management models over the last twenty years. Mentoring in a way that uses these models to illustrate, and does not go any deeper into the application of a model and its limitations to the mentee’s specific issues and business environment, sells the mentor and the mentee short. It also certainly results in the mentoring program being much less productive than it otherwise could have been.

Mentors should use models to illustrate but if they cannot help the mentee apply it in detail to their business situation, then they should not use them.


Mentors need to have agreed a coherent set of objectives for the mentoring relationship. In addition, they need to establish some ground rules for the engagement which include, but are not limited to:

  • Frequency of contact
  • Protocols for emergency contact
  • Topics to be discussed
  • Topics off-limits (mindful of the deadly sin of acquiescence)
  • Turn-around time for interactions by email
  • Respect
  • Preferred method of contact.

With the right structure, commitment and training, a good internal mentoring program yields benefits to the mentee, the mentor and the organisation. To ensure your program enjoys success, be mindful of the seven deadly sins.

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