When mentoring turns into career counseling

fork in the road

If you do a Google search on the word “mentor” after parsing a few pages of links at most you’ll find that there are basically four types of mentoring:

  1. Mentoring of youth – particularly disadvantaged youth, by adults in school, after school programs or camp.
  2. Career mentoring – where more senior employees provide advice and guidance to younger employees on how to climb the company’s career ladder.
  3. Sports mentoring – often overlapping with mentoring of youth, but similar to career mentoring where more successful and experienced athletes help others to learn the finer points of their chosen sport.
  4. Mentoring of entrepreneurs – the focus of Mentorphile, where experienced business people and successful entrepreneurs help the founders of startups with advice, guidance, and feedback.

But I’m starting to see something new the world of mentoring, perhaps because of its increasing popularity or because so many people are attempting to become entrepreneurs and finding that for one reason or another it’s not for them.

This doesn’t happen often, but it happens enough that it is worth bringing to the attention of mentors. We need to be alert to signs that a founder really might be better off pursuing a career rather than trying to start a company. I would strongly recommend against advising a founder to abandon their startup, but on the other hand it would be a mistake to abandon a founder who has decided a startup isn’t for them.

So how can we help? First we need to get to know founders beyond their pitch decks and their degrees. Find out what motivates them. Is it a desire to make money? To change the world? To see their idea spread? To help others? To keep up with their peers? Learning what it is that motivates the founder can really help when the founder comes to you as a few have, to say that they really want to pursue a career, not a startup.

Founders who simply want to make money most often can do better financially joining another founder’s startup or taking a position in the finance or high tech industries which pay high salaries. A founder who wants to change the world or see their idea spread may want to consider options such as joining a non-profit or perhaps a –B-Corp that is in alignment with their goals. Founders who want to keep up with their peers might be coached to viewing taking a career track as in no way inferior to founding a company, and actually more likely to lead to the outer trapping of success that they may value.

Advising the former founder to start “interviewing for information” instead of simply plunging into the job market can help them to discover the intersection between what they want and what is actually available in the job market. The founders I’ve worked with who have decided that startups are not for them have had deep STEM educations and job experience. Connecting them with their universities career centers or with other resources may be more helpful than trying to turn yourself into a career counselor. So being familiar with these resources in your area can be very helpful on those rare occasions when you find one of your mentees who really want to find a job, not found a company.

There are really two sides to handling the transition from founder to employee: finding a job that fit’s your mentees needs and wants, and helping them leave the world of startups gracefully, no matter what stage the startup is at.

Without exception the mentees I’ve worked with to date have been at the idea or idea validation stage. They haven’t formed a corporation or taken on an investment. They have engaged in the customer development process only to find a lack of deep interest on the part of customers or facing the mirror, their own lack of real interest in being an entrepreneur.

But even if a company has been founded and lauched a product there are good exit strategies, ranging from licensing the product to another company, handing off to a co-founder, or letting people know that you’ve found a more exciting opportunity at XYX Corp.

Investors and advisors are obsessed with product-market fit.  But rarely does the subject of founder/entrepreneurship fit come up. But when it does, if mentors are prepared to handle the situation, by knowing the founder, knowing their aspirations, and knowing local resources that can help the mentee transition to or back to a corporate job where they can succeed.

As I see it that’s the job of mentors: not to crank out more and more startups, but to help their mentees to succeed on their own terms. Having a mentee realize that startups are not for them and move into an exciting job in an established company is just as much as success for a mentor as seeing a founder decide to incorporate.

Not everyone is cut out to be an entrepreneur. It can be a difficult, stressful, and lonely job lasting years before any real satisfaction is attained. So for founders, it’s perfectly ok to realize the startup world is not for you. And for mentors, to be prepared to help any mentees who decide to take the career path instead of the startup path.


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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