Have You Hired Your Boss Lately?

Throughout my career I have found interesting and satisfying employment and extracurricular opportunities in many different, though entirely predictable ways. I relied on my schools' formal recruiting processes, job application websites, the referrals of friends and strangers, and recruiters. Of course, I also used social networking tools such as LinkedIn, where I normally heard from recruiters, managers, and leaders. I lived a very standard, predictable prospective candidate experience. 

Everything changed about eight months ago. I was happily employed and decisively loved my job. Though I was contemplating future opportunities — three to five years in the future — I was neither looking for a new position, nor had I narrowed my goal as to what I would be looking for. I even loved my routine, to the extent that you can have one when working at a startup.

One sunny day as I was returning from lunch, I received an unusual LinkedIn invitation to connect with Jesal Shah, a fellow startup attorney. After a few pleasantries, Jesal went straight to her pitch. She first told me about ClearSlide, her amazing employer, and how much she loved her job. She then gave me a flattering compliment about my achievements and told me that I would be a perfect candidate for the head of legal opening at ClearSlide. Finally, she asked me if I would be interested in the job opening and being her mentor.

Forget about the job, I was interested in meeting Jesal! Numerous articles are written about how to effectively find and ask for mentors and sponsors. Nearly every article claims that a direct request may "kill the mood" and put too much pressure on a potential mentor-mentee relationship, not unlike asking for an intimate relationship on a first date. Yet there it was: a very direct, in no uncertain terms, request for mentorship, which I admired and loved.

Jesal's direct request, sandwiched between compliments and promises of amazing experiences, worked. Perhaps the directness of her request resonated with me because I'm fairly direct myself. Indeed, the same set of facts may have led to a different outcome with a different person. Yet my near-instant response to Jesal — "When do you have time for coffee?" — suggests that sometimes, all you have to do is ask directly and in no uncertain terms.

The next day's coffee meeting with Jesal was another new experience for me. She grilled me in great depth about my interest and experiences with mentoring. She asked for examples, specific circumstances, and actual outcomes of my mentoring relationships. She was eager to learn, and clearly had skin in the game.

I have experienced numerous interviews and screening questions throughout my career. Jesal's series of in-depth questions were uniquely focused on my mentoring and management skills. In fact, it was so in-depth that toward the end of our coffee I offered her an opportunity to contact my mentees and ask them the very same questions directly.

Eventually, after meeting a few more people, I accepted the job at ClearSlide as head of legal. Eight months later, I can confidently say that it has turned out to be one of the more satisfying mentoring relationships I have had throughout my career. A number of factors contributed to the success of this relationship.

First, Jesal knows what she wants, where she is heading, and what kind of help she would need on her journey. It is much easier to be direct and to the point when your objectives are apparent, and not mysterious, especially to you. As you reach this clarity for yourself, asking for a mentor, even directly, is an obvious natural outcome.

Second, Jesal's questions carefully screened for a mentor role that makes sense in light of her career goals, personality, and overall fit. In the end, there is no objectively perfect mentor even though there may be a "perfect" mentor for a specific person's specific goal. Just like with any interview, it is worth taking the time to understand yourself and your goals and to make an effort to screen for the one person who is willing and able to help. 

Third, Jesal was actively on a mission to hire a committed manager to help her on her quest. During interviews, consider hiring your perfect manager, leader, or colleagues. Use the interview time as an opportunity to ask them directly if they are willing, outline your expectations for this relationship, and have them confirm that it is agreeable. Make the mentoring relationship a job criterion and hire against it as you would for any other substantive or soft skill. Getting on the same page about mentorship expectations during the interview certainly streamlines the relationship.

While it can be nerve-wracking to disregard the norm and directly ask for a mentoring relationship, for the ambitious, clear-minded professional being honest and direct can certainly pay off. Taking this bold step could lead to a giant leap in your career and personal satisfaction. At worst, you'll realize that the opportunity and mentor wouldn't be the right fit, and at best, you'll form a lasting and satisfying professional relationship! Don't be afraid to turn down an opportunity if you sense that the mentoring relationship wouldn't be ideal or suited to you and your goals. Every interview is a chance not only for your boss to hire you, but for you to hire your boss. After all, every relationship, including mentor-mentee relationships, is a two-way street.

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