15 Grave Mistakes To Avoid Making With Your Mentee

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Members of Forbes Coaches Council

The Forbes Coaches Council has put together a list of the biggest mistakes a mentor can make in their relationship with mentees. The Forbes Coaches Council is an invitation-only organization for business and career coaches.

Here’s their list, but as per my usual practice I’ve annotated the items with my own comments. Read the original article to see the explications from the Coaches Council. While I’ve written elsewhere about the differences between coaches and mentors, perhaps Steve Blank’s definitions are the best illustration.

Mentors, teachers and coaches advance your personal career. If you want to learn a specific subject you find a teacher or take a class.

If you want to hone specific skills or reach an exact goal, hire a coach.

The one that founders sometimes forget is the mentor. If you want to get smarter and better over your career, find someone who cares about you enough to be a mentor.

So with those distinctions in mind, let’s go through the list.

1. Lacking Integrity

Having no hidden agendas is perhaps the number one criteria for the MIT Venture Mentoring Service, and VMS polices this policy very carefully. The most common agenda I’ve seen in mentors is that they are either interested in investing in the company or in selling the company professional services, legal, financial or strategic. Another may be a desire to actually join the company. Obviously any agenda will severely bias a mentor, so founders are well advised to make sure their mentors don’t fall into any of these categories.

2. Not Setting Goals For Mentoring Relationship

The first mentor meeting is key to avoiding this issue. It’s very important for mentors to understand what the mentee is looking for in the relationship: advice? guidance? feedback? If the mentee is looking for help raising capital or in finding customers that’s generally not what mentorship is about and while a mentor may provide this type of help on occasion, it should not be the goal of the relationship.

3. Betraying Confidentiality

All MIT VMS mentors sign an NDA and as part of the first meeting we inform the founders that we are all under non-disclosure, so they can feel comfortable discussing their company’s business with us. What mentors sometimes forget and founders often forget is flagging issues that they are sensitive and company confidential.

4. Getting Stuck In The Mentee’s Emotions

Where I’ve seen mentees get emotional is when they are faced with severe conflict within their team, often with a co-founder, and they feel stuck, frustrated and upset because they don’t see how to get out of what they view as a crisis situation. This is when mentors do have to remain calm, cool, and collected and be careful not to take sides. There can also be a temptation on the part of experienced mentors to play amateur lawyer in an effort to help the founder. The best approach is to help the mentee elucidate the problem, including its history, and then point the founder to appropriate resources, such as VMS legal office hours or the organizations like the Boston University Law Clinic. 

5. Lacking Insight

It’s not possible for a mentor to have insight into every company and every founder – mentors are far from omniscient. The best we can do is to clearly explain the basis for any advice or guidance we provide and frankly admit where we may not be able to help – such as solving a complicated IP dispute – and if possible, referring the founder to other resources.

6. Not Honoring Their Uniqueness

As part of first meetings we always inform founders that what mentors offer is advice, we don’t dictate behavior. In fact we make it clear that sometimes mentors will disagree on the best advice for a founder. It’s up to the founder to decide what advice to follow. Every startup is unique, but it’s easy for an experienced mentor such as myself to fall back on tried and true advice – I’ve caught myself doing this on occasion. That’s why team mentoring is so effective, as varying viewpoints will counteract any tendencies to providing advice, guidance or feedback that doesn’t take the uniqueness of the founder and his or her situation into account.

7. Not Taking Time To Make Time

Respecting each other’s time and schedule is a commitment that both mentee and founder need to make. Meetings need to start and end on time. And as one athlete said recently, “If I’m on time, I’m late.” If both mentors and mentees get into the habit of being 5 minutes early that can not only help meetings start on time but also allow for a few minutes to socialize without taking away from mentoring time.

8. Scolding Them

Mutual respect is key to the mentoring relationship. Mentors have to be very careful when providing any negative feedback. The best approach when disagreeing with a founder’s actions or plans is to first question them. Then to use examples where those actions or plans haven’t worked for others. All criticism needs to be constructive, meaning helpful, positive, productive, and encouraging.

9. Devaluing A Mentee

As above, mentors need to respect founders; founders need to respect mentors. There have been two occasions in the past 8 years of my MIT VMS mentoring that I’ve had to ask to be taken off a mentoring team as I felt that the mentee did not respect the process and therefore I didn’t feel I could help them. If you find a mentee who is too prideful, arrogant or just doesn’t want to engage, the best solution may be to terminate the relationship.

10. Not Allowing Failure In The Relationship

Mentors have to be careful about being overly directive. We have to allow founders to fail. What’s most important is how they react to failure and how we can help them when they do fail. But if you go into mentorship thinking it’s your job to prevent any and all failures on the part of your mentee you are both bound to be disappointed and bound to do a disservice to your mentee.

11. Being A Poor Role Model

This mistake is most common in corporate coaching vs. startup mentoring. But many mentors are active entrepreneurs or board members. So obviously you need to walk the walk, not simply talk the talk in your behavior outside the mentoring relationship.

12. Not Helping Mentees Develop Their Own Vision

Mentors need to understand the strengths, values, and passions of their mentees. Then we need to help them develop a mission that’s aligned with those characteristics. It is both too easy and very dangerous to try to craft a mentee’s vision for them.This can be tempting when seeing a talented mentee who is struggling to develop a vision. Helping to develop, clarify and communicate a vision, yes; providing the mentee with your own vision, no.

13. Failing To Set Up A Roadmap For The Relationship

For mentors of founders this is all about setting expectations. Mentoring needs to be an on-demand service to founders, not a demanded-upon service pushed on founders. So at first meetings it’s always important to outline what a mentor can and can’t do and how it’s up to founders to take advantage of the service provided. Mentorship is not a business relationship where there is a contractual quid pro quo, it’s a volunteer service designed to help founders succeed.

14. Not Trusting Your Mentee

Trust is critical to all relationships but even more important when mentoring a founder who may be betting his or her career on their startup’s success. These are high stakes indeed! So what is trust? It means that the mentee can rely on the mentor for unbiased advice, and confidence that the mentor has his or her best interests in mind, and has no hidden agenda. Trust also means having an obligation and responsibility, as mentors must have, to do right by their mentees. If founders can’t trust their mentors they will not be open with them and a successful relationship can’t be built.

15. Having An Agenda

Actually I so have two personal agenda items when I mentor: one, is to learn, either about a new technology, product or business model or new business issue, the other is to see my mentee succeed. There’s nothing like hearing that your mentor just raised capital, as one of my founders just has done or has succeeded in securing multiple pilots with important customers, as two others have done recently. But any other agenda is going to distort the relationship. If you want to invest, join an angel network. If you want to sell professional services, don’t do that under the guise of mentorship; and if you want to join the company or act as a consultant, step back from your mentoring role.

So that’s a very long lists to “Not to do’s”. And as mentioned above, the list was generated by coaches, not mentors, so some of the advice is better suited to a corporate career coaching environment than mentoring entrepreneurs, but it’s all worth keeping in mind, whether you are a mentor or a founder seeking mentorship.


Author: Mentorphile

Mentor, coach, and advisor to entrepreneurs, small businesses, and non-profit organizations. General manager with significant experience in both for-profit and non-profit organizations. Focus on media and information. On founding team of four venture-backed companies. Currently Chairman of Popsleuth, Inc., maker of the Endorfyn app for keeping fans updated on new stuff from their favorite artists.

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