Asking for Mentorship

asking for mentorship

Don’t.

… would be my short answer.

The longer answer… I’ll start with a story.

My First Mentor

This is embarrassing to admit, but 6 years ago, I barely knew what a resume was. As a hint of my ignorance, my first ‘resume’ was 3 pages long, double-spaced, and included two lines explaining a babysitting license I got back in middle school. So, within 10 seconds of it going up, I signed up for the resume workshop. In my hurry, I signed up for the first spot with the first “critique-er” I saw.

When the fateful day arrived, he didn’t show up at our appointed time. After waiting 15 minutes and asking the workshop leads, it turned out he was stuck in the depths of traffic.

But hell, I wasn’t going to go home empty-handed. So, I went around the bustling room, catching each “critique-er” there whenever they had a break, to ask them to look over my sad excuse of a resume. By the end of the two-hour workshop, I had taken notes about the flaws of my resume from every alumni there – half of whom ran through various interview questions with me – except for one. The one I had initially signed up with.

After hearing gossip and rumors from the alumni of how brutally honest he was, I had to meet this mysterious fellow. Eventually, he arrived. And luckily, the alumni invited me to join them for a late dinner. And that night, he left me with one sentence: “If you want my advice, you better take it seriously.” Not in the sense that I need to follow exactly what he tells me, but that I won’t hear then forget it the next morning.

Over the years, I’ve truly appreciated the analytical mind he brought to temper my creative mind. His advice saved my neck saved my neck at multiple crossroads of my career. He was able see around the corner when I couldn’t – a tactical mentor. Though I didn’t use his advice every single time, I always came back to him with the post-mortem.

  • How did I use his advice?
  • If I did, what was its impact?
  • If I didn’t, what was my internal calculus for choosing so?

He never pressured me to use his advice, nor did he ask that I report back to him each time. But I did. Over the years, I’ve been there for his highs and lows, just like he has been there for mine. Before we became mentor and mentee, we realized we had become friends. Ironically, to this day, he still hasn’t seen my resume.

The Bigger Picture

You might call it availability bias, but over the 6 years since then, I’ve reached out to many people – punching above my weight class, inspired to seek mentorship. But out of all the 20+ people that I asked for mentorship on the get-go, not a single one was willing to take on the responsibility for a stranger. And rightly so. Like any other relationship, mentorship requires time and commitment. Without any precedence, it’s hard to make that decision with asymmetric information.

The Venture Parallel

Even as investors, who notoriously have to be willing to not only mentor others through “just a pitch”, but also commit dollars to where their mouth is at, each round of startup funding takes at least 60-90 days of diligence and working together, before we invest. Our goal is to be ‘the best dollar on your cap table‘.

In a literal sense, a dollar is a dollar. Whether you get it from your parents as an allowance when you were 7 years old or from your managerial salary at 27 years old, it’s the same. But, in venture, there’s ‘dumb money’ – money in its most literal sense. And there’s ‘smart money’ – money that comes with advice, resources, social and professional networks, and help.

In most cases, an early-stage founder wants ‘smart money’. In that frame of mind, you want the investor(s) that have the best networks, the best resources, the best expertise, and possibly, the best brand, at your stage of a business. So your pitch should be hyper-specific. As with any ask in the world, nothing is ever guaranteed. But, to increase your chances of a “yes”, the best founders build that relationship before they need to fundraise.

Circling Back

For any other person out there, whose day job isn’t to take measured capital risk, you’ll have to work even harder to convince someone to take that leap of faith with you.

When you ask for mentorship, or advice, in general, follow through with it. Make it known that it is valued. And, show your progress after having tried it out. No person speaks hoping to reach deaf ears. So, if you don’t think you’ll have the mental and physical bandwidth to turn advice into action, don’t ask for advice. And definitely, don’t ask for mentorship. It’s not worth your time or theirs.

As a footnote to myself and to others who may be seeking advice, even with this mindset, there’s no silver bullet. Be curious. Be mindful. And, be creative. My favorite creative ‘ask’ so far is “I will pay you to work for you”.

And to my first mentor, Happy Birthday!

Photo by Juan Pablo Rodriguez on Unsplash


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Investing in Mentorship

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.