Tag: asking

In theory, there’s nothing wrong with seeking mentorship to gain experience or offering mentorship to give experience. In fact, advice is still something I seek, as I’m still on the green side in the larger landscape. In reality, every person only has 24 hours in a day and limited bandwidth, which inhibit the quantity and quality of mentorship even if the mentor wants to. Providing mentorship, after all, requires mentors to accept the opportunity cost to do something else they could be doing, and prioritize the learning exchange. I characterize mentorship into two categories: passive and active. Passive mentorship is where one purely obtains advice from a mentor, whereas active mentorship is where advice is coupled with hands-on learning experience.

Mentorship is often seen as a huge time commitment, which is why when asked to provide mentorship, many potential mentors, who have yet to commit a large chunk of their schedule to advisorship, turn it down, as soon as they get the request. Having led three mentorship programs across two organizations, as well as hosting founder brunches and brunches with strangers for peer mentorship, here’s why most prospecting mentees are turned down: ensuring value and capping the mentor’s own downside.

Ensuring Value

When mentors are approached, the two most frequent asks are: “Can you be my mentor?” and “What can I help you with?“

The former, “Can you be my mentor?“, often scares many mentors away. Just the word ‘mentor’ or ‘mentorship’ incites the connotation that the mentee is setting a high bar of attention expectation, which in undefined with no clear asymptote or time horizon, in sight. Something I learned over the years, unless I am the one hosting a mentorship program, is that the best mentor-mentee relationships, never mention the word ‘mentorship’, at least not in the first few exchanges. The question itself is nebulous in nature. The nebulosity leaves the mentor needing to expend their creativity to guess what mentees would like to learn. A better approach would be to have a targeted question detailing exactly what you want to learn, with evidence of putting in work to resolve the question beforehand.

Here’s a format I personally use when reaching out for advice, or for passive mentorship:

“I’ve been obsessed about X recently, and have tried out Y and Z, to produce Y’ and Z’ results (where I expected Y* and Z*). As someone I deeply respect in X industry and whose insights I have used in trying out Y and Z, what might I be misunderstanding or should have done differently? If I caught you at a bad time of the year, is there someone or some literature you can point me to, to help me achieve the desired result?”

The latter question, “What can I help with?“, unfortunately, is evidence that the prospecting mentee has not done their diligence. Take for example, helping a VC. There are really only five ways to help:

• Deal flow – amazing startups that fit the partner/fund’s investment thesis
• Sales/BD intros – firms that are buying, partnering, or co-investing into the fund’s portfolio
• Portfolio support – helping the fund’s existing portfolio startups with their various impending dilemmas
• Follow-ons – downstream investors for the fund’s portfolio
• LP (limited partner) intros – high net-worth individuals or groups who may fund a VC’s next fund

In knowing one’s specific skill set and network, ideally, a prospecting mentee can help where his/her strengths lie. This is also true on a broader scale, when offering help to friends, acquaintances, and just people who need help, knowing what kind of help they need and when they need it means the world to those in need. After all, a friend in need is a friend indeed.

Capping the Downside

Most mentors, either explicitly or implicitly, want to ensure the experience is valuable and productive to the mentee, leaving the upside to be essentially limitless – for both the mentor and mentee. Having a set of clear measurable goals, one, defines the time horizon, and ,two, helps the mentor understand what is valuable to the mentee. A good reference point are how companies structure KPIs, or key performance indicators. At the same time, clear, measurable goals helps the mentor cap their maximum downside, so the relationship won’t end up becoming a slippery slope. Consider what the mentor has to risk to help the mentee: time, attention, money, reputation, opportunity cost, “knowledge IP”, and so on.

Per the format I use as I mentioned before, it caps the maximum time investment a passive mentor needs to provide to the length of time it takes to answer one question. Or if they’re short on time, I have recognized that they’re busy, and have given them an easier ‘out’ to the question.

In closing

This piece isn’t meant to disincentivize people from seeking help and mentorship, but rather to provide another perspective to those of us, including my younger self, who have yet to figure out their own approach to mentorship or are looking to explore other methods or just to peer into my mental calculus. Mentorship, at the end of the day is an investment – an attention investment. As with all investments, the goal is to lose little, win big – or how we like to say in VC, “de-risk the investment.” The upside, or if I’m continuing on this VC analogy, the return on investment, or ROI, knows no bounds. Even for the mentor, who at first glance, may seem to be losing more than winning, gains the satisfaction and pride of paying it forward, a new friend, and leadership skills, even before what the future may realize.

After all, some of the greatest figures in history and in our world today grew from mentorship: Socrates to Plato, Ralph Waldo Emerson to Henry David Thoreau, Ed Roberts to Bill Gates, Maya Angelou to Oprah Winfrey, Sire Freddie Laker to Richard Branson, Bill Campbell to Steve Jobs, Steve Jobs to Mark Zuckerberg, and the list goes on and on. As many studies have shown, and of course, with a few caveats, happiness can be achieved by spending money on others. In this case, that money is time and attention.