6 Things You Should Never Ask Your Mentor

If you have a great mentor, they’ll make you feel like there’s no such thing as a dumb question–but a few requests are off-limits.

6 Things You Should Never Ask Your Mentor
[Photo: Flickr user david basulto]

Successful entrepreneurs who had a mentor during their rise to success will always stress the important part this person played in their development and growth as a founder. However, many new or failing entrepreneurs are unsuccessful in their efforts to land a good mentor–not because their resume isn’t good enough to be impressive, but because of how they approach the person.


When you’re approaching a prospective mentor–and even after you land a great one who agrees to take you under her wing–there are a few things you want to make sure you never ask:

1. To Take A Leap Of Faith

Successful people may take calculated risks from time to time, but they don’t flat-out gamble with their time or effort. This means you can’t approach them starting from absolute scratch. If you want one of these people to give you the time of day, you need to show them you have chops by building something on your own and generating at least a little traction first.

2. For A Step-by-Step Roadmap

No successful person wants to hold your hand and walk you through every single thing you have to do. This would likely take even more time than it would for them to start a new, successful venture of their own. This is way too big of a commitment to ask for at your stage.

3. For A Handout

Successful people don’t become successful by just giving things away. Your mentor is giving you their time and their battle-tested advice already, so don’t push it. If you’re looking for funding, connections, referrals, or anything else, make sure these are voluntarily offered rather than asked for, or you risk putting an unnecessary strain on a critical relationship.

4. For Seed Capital

While this is briefly touched on above, it’s worth emphasizing in particular. You may end up getting mentorship from investors, but you should not look for investment from a mentor–especially early on. This person has already taken a huge chance on you, and it’s likely been a relationship where they’ve given a lot without much gain. Instead, try offering this person advisory equity in what you’re building for free in exchange for their continued time or effort. You’ll probably get even more value from this than you will from their money.

5. To Become A Paying Client Or Customer

Don’t try to sell your mentor anything. Keep in mind that tons of people are trying to do this to them every day, and if you want an ongoing relationship with them, you must not be one of these people. If you build something incredible and they organically sign up or buy from you, great. But it’s only okay if it happens without you asking.


6. For Trade Secrets

Your mentor has likely built their business over the course of many years using a considerable amount of blood, sweat, and tears. Any advice or guidance they give you should be voluntary. Don’t ask them to give away the farm–especially early on. This kind of access should be earned. They’ll only provide it to somebody they both deeply trust and believe in, which takes a pretty significant amount of time and effort to establish.

The key thing to remember is that in any relationship, it’s worth taking a step back to examine how your actions could be received by the other person, and if those results are the ones you want. This becomes much more important when this relationship could be the one person that could get you your dream job, land you your lead investor, or help you fix problems costing you millions of dollars.

Travis Steffen is a serial entrepreneur with multiple successful exits and is currently the founder of UP ( Travis is one of numerous founders and VCs sharing their insight and advice with other entrepreneurs at MentorMojo–an entrepreneurial e-learning platform. Follow him on twitter @TravisSteffen.

Young Entrepreneur Council (YEC) is an invite-only organization comprised of the world’s most promising young entrepreneurs. In partnership with Citi, YEC recently launched StartupCollective, a free virtual mentorship program.