• Abhishek Singh

9 reasons why conventional Mentorship often fails, and there is a saviour each time.

Updated: Jul 24



We all love Mentorship, and each of us is incredibly thankful that so many gifted, talented and benevolent people exist to enrich lives of multiple others around them so that the latter is more successful or happier over the variety of occasions they partner with their mentors. Most successful people today do attribute at least a part of their success to their mentors/coaches/guides, which could very well be school/college professors or colleagues at work. The best of mentorships share a bond of mutual respect, trust, emotional bonding, and importantly an Outcome-driven approach. BUT, unfortunately, the vast majority of mentorships turn out to be just reasonably good, instead of long-lasting enriching partnerships. Here is the why behind this fixable & impactful problem:

  1. Great breadth & expertise don't go hand in hand: Mentorship is a formal relationship b/w mentee & mentor over a period of time, wherein a Mentee tries to learn as much as possible from an experienced Mentor. While emotionally fulfilling and convenient, it is not possible for any 1 Mentor to be significantly more skilled or experienced than their mentee for every major task the Mentee wants to excel in. Human problems are diverse if you sum up the professional, social & personal aspects of it, and it could get hard for 1 Mentor to come across as a 1 size fits all solution for the same for every mentee. Additionally, few mentees alone might not be able to exploit & grow a mentor's abilities to its fullest. This could prove to be a sub-optimal development for either side.

  2. Incentives are often imperfectly aligned: Sure, a Mentee might gain relevant expertise or skills from a mentor's experience, but often this partnership is not mutually beneficial. How is the mentor gaining in terms of skills/experience, if the task being discussed is not exciting or impactful enough? Also, is the mentor getting paid fairly for his time & expertise? If not, then this kind of partnership is not sustainable in the long run for great mentors who can monetise somewhere else for their skills, and that adversely affects mentees in the long run as well. Additionally, a mentee might get matched to a mentor who might somewhat limited expertise in focus areas that matter immensely to the mentee.

  3. Inadequate use of time: In cases, when objectives and execution are not clearly aligned, often the mentee ends up not getting enough time or the mentor ends up having spent too much time on a Mentee. The culprit here is much lesser of the people involved and more of the nature of the partnership as 2 stakeholders embarked upon a somewhat longer duration of engagement.

  4. Personality mismatch and lack of choices: Infrequently so, but there would be situations that you get paired up with a mentee or mentor whom you may not admire much for their execution, ethics or gesture. If it is about working with them for just a few sessions, it might not make any difference, but partnering with them over a considerable tenure of several quarters or years might make work less enjoyable. Does this remind you of images of an annoying child boss/coach or rebel employee/student? The real issue out here is not the undesirable counterpart but your lack of freedom to get a new counterpart who matches better with your preferences.

  5. Limited networking for either side: 1:1 relationship have their fair share of joy with both sides getting sufficient time to discover each other over a tenure of time, and getting to better understand each other's preferences/abilities. This can, of course, lead to a more personalized experience for either, which is always cherished. The flip-side here is that since your time is divided with much fewer people, you benefit from limited expertise and from experienced/knowledge of fewer people. As a mentor, you have lesser mentees to guide and grow your skills. This means you are learning lessor for the time spent (everything is the same) and you walk out with a smaller network towards the end of the partnership, which is less desirable as compared to having a larger network.

  6. Limited perspectives for either side: On the same note as above, fewer people in your network leads to you benefiting from fewer perspectives when you are solving problems for yourself or your mentees. Having fewer perspectives can lead to limited approaches, ideas & hypotheses, which often proves to be a disadvantage.

  7. Tenure based mentoring instead of Expertise/experiences based: Traditional Mentorships often foster a great emotional bond, but often this bonding comes from tenure or length of mentorship. While this does create a great working experience for both mentee & mentor, it often does not lead to their most optimal career development. For example, if you are in school and your assigned mentor is one of the senior researchers, they will be of great benefit to you when it comes to advancing your research & technical chops, but let us say if your goal is to submit a B-plan based on your learning so far, won't you benefit from partnering with

  8. Dispute mediation: If and when things go sideways, how do we resolve things amicably for both stakeholders to ensure a smooth landing or a stable flight onwards? Do we always have a non-partisan 3rd party that is available to find a fair, fast and convenient solution every single time?

  9. Lack of performance pressure: While we are no lovers of stress and work anxiety, but legend has it that complete lack of the same for one side, can lead to a sub-par experience for the other side. Does this give you a flashback of any experience in a bureaucracy or any unreasonable authority that you were dependent on? We feel your pain from 1st hand experience and are building a solution that will go a long way to ensure both sides feel compelled enough to perform their best when in a partnership.


While the above list makes the point but it doesn't stop there. We repeatedly want to point out that the fault is much lesser of the individuals participating and more in the nature of how a traditional mentorships work. Humans are unique and what makes them unique are their situations & problems, so it makes a lot more sense to have solutions for mentorship that can be personalised for each person for each kind of situation they come across. This is exactly where Micro-Mentorship shines brightly over the shoulders of its older & traditional cousin Mentorship. Micro-Mentorship is expertise or instance-based learning which is fast-paced, outcome focussed and focuses on taking a 360 view for every person. We are talking about covering personal, social & professional aspects for every human across every major situation/opportunity they come across. It is hard if not impractical to expect traditional mentorship to fulfil the same.

At Headstrt, we see Micro-Mentorship as a global & impactful solution for most people. We believe a large & engaged Micro-Mentorship graph can easily overcome the listed shortfalls when executed in a transparent, empathetic, convenient, affordable, timely, and outcome-driven manner where both parties are empowered in a world of choices, for every high stakes situation they run into. We are currently working to bring this in the palm of all our users through our Cross-Platform app. Beta Signups are open, so we would love you to check out our site.

Investments | Headstrt - Wisdom Sharing Platform
Social | Headstrt - Sharing Wisdom
Social | Headstrt - Sharing Wisdom

©2020 by Headstrt Inc.