Dear Startup: A Faux Advice Column for Better Mentoring

by Duy Tran, guest blogger & faux advice columnist

ncblog-abbyIf someone decided to write a “how to” guidebook for mentees seeking effective mentors, I believe it might read like a dating advice book!

This is not surprising, if you stop and consider it, because a good mentor-mentee relationship is supposed to be emotionally stimulating AND tangibly beneficial.

Good mentors can be more than strictly business partners where only clear goals and objectives are set, yet it is also different than merely a friendship because some level of giving is still expected in a mentorship.

Thus, I’ve distilled all the insights and advice I received in my conversations with former mentees and mentors in a faux advice column where current mentees, mentors, and program leaders can improve their “game.”

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Dear Reader,

In the real world, Prince(ss) Charming doesn’t gallop into your life and sweep you off your feet, and you shouldn’t expect to find a good mentor through serendipity. Tony Aguilar from Student Loan Genius emphasized the need to hustle, hustle, hustle; in other words, put yourself out there!

Kim Gorsuch from Weeva corroborated and expanded on this advice by suggesting to think of interactions as belonging to three different tiers:

  1. tier one is the first date, so to speak, where you assess mutual interest
  2. tier two is when a mentor becomes interested in your venture and decides their expertise to help you, but it is more of a one-time situation
  3. and tier three is when the mentor becomes so invested in your venture that they embed themselves into your team for the long run and help you grow over time

Tier 2 and 3 interactions are the ones you’re shooting for, but that is only possible after many, many tier 1 interactions.

Now, of course, every entrepreneur knows that hustling is a key component of success, so what’s so insightful about this advice, anyways?

Well, a topic that was raised in every single one of my conversations was that oftentimes these initial interactions are mandated, forced, or otherwise inorganic. Thus, it becomes difficult for a mentor to become invested in your venture.

This is where having honest communication is absolutely crucial. Founders I spoke with would really appreciate it if mentors were upfront about not being interested in a venture instead of stringing them along. Transparency, even if it’s a little uncomfortable, would go a long way in increasing the efficacy of tier 1 interactions.

However, don’t be disheartened if someone isn’t interested in your venture because they can still be invested in your success. If half of the transparency equation is mentors being brutally honest, then the other half would mentees “being themselves.”

It would be a good idea to pitch yourself so that uninterested mentors can refer you to a different mentor or even convert them into a cheerleader for your venture. In fact, there was unanimous consensus that one of the best, if not the best, aspect of mentorship was having a mentor as your cheerleader.

Kim Updegrove of Milk Bank of Austin said that an invaluable aspect of her mentorship is her mentor telling her she can do it, that being overwhelmed sometimes is normal and that she can push on.

Entrepreneurship is hard and you can get all the best advice in the world, but it’s all useless if you don’t have the willpower to execute those advice. Look for mentors that will emotionally support you in addition to offering their expertise.

Of course, the burden of good mentorship should not fall solely on the shoulders of the mentees and mentors, which means that program leaders who manage mentor networks really ought to consider some rudimentary matchmaking framework. This will allow for mentees and mentors to look for common ground and build upon it.

Suggestions during my conversations included specifying whether or not the mentor was also looking to invest, opt-outs for different types of ventures, and being forthcoming about their time commitment.

Program leaders wouldn’t even need to reinvent the wheel: there are plenty of matchmaking models that are already quite successful. Examples range from dating sites – I wonder what a “Tindr for mentorship” would look like – to more complex and thoughtful models, along the lines of roommate matching at colleges.

Finally, be flexible and allow yourself to be challenged. One founder suggested not having too much of an agenda when looking for mentors.  Otherwise, your worldview is too myopic to incorporate any major or unconventional advice that seeks to address critical flaws in your venture.

It is also useful to avoid overestimating your abilities. Going back to the basics can prove to be useful when reassessing your business model, either as validation or recognizing the need for change.

Being challenged is also good for mentors! A founder really appreciated when her mentors had differing opinions and they would debate their advice because that discussion leads to a more nuanced and holistic understanding of the situation.

So, Dear Reader, to summarize, when it comes to ensuring a more successful mentor relationship:

  • Put yourself out there!
  • Honest communications is absolutely critical
  • Look for a mentor who is a true cheerleader
  • Find common ground and build upon it
  • Be flexible and allow yourself to be challenged

ncblog-homeawayGood luck and keep searching for that Mr. or Mrs. Right Mentor. Hopefully, by following this advice, there will be celebration bells of a different kind ringing in your future!

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