Why Does Mentoring Sometimes Fail?

Mentoring partnerships don’t always work out. It’s possible for this to not be the fault of either party, it’s just that things didn’t click relationally or circumstances suddenly shifted. It happens. But there are some very common reasons why mentoring becomes disappointing from the mentoree’s point of view and several of these are avoidable. Every mentor who desires to serve their mentorees well needs to keep an eye on these factors to make sure they are not falling into bad practices.

I’ve listened to hundreds of mentorees reflect on their experience and these are the top six reasons they identify as those that cause mentoring to fail.

  1. Too much telling, not enough asking and listening. Although this varies somewhat according to culture, the vast majority of mentorees do not come to a session with their mentor looking for a lecture. If they want to get expert input on a topic, they will find a podcast for that. The mentoring session is a special place where they can find an interactive conversation and they don’t have to apologise for being the centre of attention.
  2. Mismatched expectations. This starts with the word ‘mentoring’. People understand different things by this term and, let’s be honest, it really can take many different forms (see my post on ‘Modes of Mentoring’). Investing time at the outset to clarify and align expectations will pay huge dividends.
  3. Haphazard connections. Without appropriate planning and scheduling to set up mentoring sessions at regular intervals, mentoring conversations tend to only take place when there is some sort of trigger event – usually a negative one. That does not lay a good foundation for working together positively towards the growth and development of the mentoree.
  4. Lack of depth. This might be experienced as a disappointing level of emotional rapport, intellectual engagement or spiritual discernment, or even a combination of those things. It’s an error for the mentor to always keep things bright and breezy in an attempt to make mentoring sessions an enjoyable experience. Equally, it’s self-defeating for mentorees to only share at a surface level, staying in ‘safe’ territory. It’s vital for mentoring partnerships to get out of the shallows and ‘swim in deep water’, always with the proviso that you call for help if you start to drown!
  5. Poor continuity. This can happen when a mentor fails to keep track of the mentoree’s story and does not pick up on things from previous conversations. It’s frustrating for a mentoree to have to repeat the background to their circumstances, and disappointing if their mentor does not remember a significant point from the previous session. But mentorees can also contribute to the problem if they don’t do the hard work of identifying the key issues they wish to grapple with and stick with those issues even when it gets difficult.
  6. Inconsequential conversations. How will everyday life be different for the mentoree as a result of a mentoring session? If it’s hard to answer that question, chances are the mentoring partnership is heading for a fail. Consequences may come in several forms. Sometimes it’s a particular action step that the mentoree decides to carry out. Or it might be a new way of seeing their situation, an insight, a fresh approach. Or it might be some encouragement that the mentoree receives, an inner strengthening or release of a burden. Pleasant catch-ups without consequences become a boring waste of time.

Much of the responsibility for avoiding these pitfalls rests on the shoulders of mentors. But mentorees also must realise that they could be contributing to the very factors that make the mentoring partnership unsatisfying for them. Perhaps you could use this short list as a conversation starter in your next mentoring session.