They say when you find the right person you just know.

Why do we embrace this notion for love and friend relationships, but create our most pivotal career relationships from job titles or at best, text-based inventories of skills? Mentoring is about so much more than a discrete transfer of skills - it’s about sharing the real failures and successes we inevitably encounter in our professional lives.

I’m grateful to have mentored as a technical lead, founder, and girl scout. I’ve had excellent short and long-term mentors and I’ve also connected with “mentors” who I wasn’t sure what to talk about with next. I’ve seen mentoring relationships between people of all ages and from casual to corporate environments and noticed a few common factors of success.

Chemistry

• You have to straight up like each other. Mentors must genuinely care about their mentees as individuals so they will share time and experiences openly, without resentment. Mentees must feel a strong enough connection to overcome the discomfort of asking tough questions and to internalize the mentor’s advice.
• Corporate mentoring programs tend to match purely based on divisions or job ranks, and their programs are valuable for networking, but rarely as effective as matches with an emotional bond.

Shared Values

• Sharing similar life values makes it more likely you’ll be comfortable with similar tactics for dealing with problems, and that you’ll both listen to each other.
  For example - I believe strongly in the free culture movement. It would be hard for me to take the advice of a technical mentor who believed in technology that strongly limits use in order to protect copyright holders, such as DRM. Without a strong basis of shared values, the depth of our relationship and ability to explore solutions together would be limited. I also might snarl at them, which could compromise our chemistry.
• Communities (vs. corporations) often spawn excellent mentoring relationships, even if they don’t deliberately facilitate, because of the strength of shared values among members.

Transparent Goals

• Both mentors and mentees must articulate and share their goals. Otherwise, you’re just hanging out.
• At the end of a session, and routinely during the active mentoring relationship, both sides should be able to ask “did you get what you hoped for out of this?”.

Once you’ve developed a relationship with someone you can learn from or share your knowledge with, the details of when, how, and how often suddenly don’t seem like such a chore. You’ll be free to focus on sharing and improving through mentorship.

Ready to mentor? Reach out to your communities and join the mentoring topic on Ohours*, which has additional tips for mentoring.

*Note: I’m an advisor and obsessive avid user of Ohours.