A Mentor’s Tale: How Startup Weekend Taught Me to Be a Better Mentor

be a better mentor

[first published on LinkedIn Pulse – Entrepreneurship & What Inspires Me]

Learning from first time entrepreneurs how to be a better mentor

*Startup Weekend is a global network of passionate leaders and entrepreneurs on a mission to inspire, educate, and empower individuals, teams and communities. The 54-hour events help developers, designers, marketers, product managers and startup enthusiasts come together to share ideas, form teams, build products, and launch startups!
Does it not usually go the other way around, though? An event catering to budding entrepreneurs relies on mentors to teach guide the presumably inexperienced participants, it’s just how things are meant to be.

During my recent experiences at Startup Weekend*, I found that to be far from the norm, that mentees can teach their mentors a thing or two, and that’s a very good thing — we’ll see why and how I was taught to be a better mentor.

Get a fresh perspective

Those who have been in or around startups for an extended period of time — and in highly competitive entrepreneurial environments this might mean as little as a few years — can quickly exhibit signs of idea fatigue. It is often said that ideas are a dime a dozen, that they are virtually worthless without a proof of concept, execution, and delivery; the idea itself does not make an entrepreneur.

While I agree that this is true to a large extent, I arrived to the realization that it is often a matter of allowing your mentees to go slightly beyond an elevator pitch (a commonly cringe-worthy experience in any case) in order to uncover what their idea and vision truly are about.

On more than one occasion I was surprised by first-time participants at Startup Weekends or similar events. Some had zero entrepreneurial experience but had ideas consisting in a new spin on an old concept. Their perspective, unspoiled and unbiased by the constant overload of other people’s ideas that old-timers in the startup scene often suffer from, might teach the old dog in you some cool new tricks.

Tip New entrepreneurs might not be yet well-versed in articulating what their idea is about but that does not render the idea itself worthless. Rather than insisting that they see the world through your lenses, ask that you borrow theirs for a little while.

Embrace the contagious enthusiasm

Having spent roughly 7 years in and around startups, I understand how easily one can become unimpressed by the stream of new ideas presented on Friday evenings at any Startup Weekend event. How many new ways of slicing bread can there be, after all? How many delivery services does a tiny city need? How many photo sharing apps?

Enthusiasm in itself isn’t necessarily valuable. I should know, I get excited to no end over a slice of watermelon. Enthusiasm about an idea, though, appears to be intimately linked to one’s drive and willingness to overcome obstacles in order to see that idea put in practice.

Allowing yourself to absorb your mentees’ enthusiasm is not always easy but I found it to be an invaluable exercise that helped me understand how to channel that energy from shrouding the intangible (“This is amazing!”) to serving the actionable (“I cannot wait to test this!”). Working “with” one’s enthusiasm and not “in spite of it” is one of the best things you can do for an entrepreneur.

Tip Try to get past the awkward moment in which something gets described as “the new Facebook”, “the new Uber”, or some other seemingly over-the-top assertion such as “it will disrupt the global mobile industry”. It usually stems from a lack of experience combined with bursting enthusiasm, not from a lack of humility or common sense. Listen to new ideas like you’ve never heard a pitch before; dig past the hyperboles to see whether you can bring to light something worth pursuing.

Use the mentor whiplash

Mentor whiplash is a pretty scary thing and it has been discussed numerous times in a variety of contexts. Fred Wilson’s post does a great job at addressing it and suggests a number of ways to counteract it.

In a nutshell, mentor whiplash describes the situation in which an entrepreneur receives plenty of advice and feedback from many mentors / VCs / advisors and they blatantly contradict each other. It’s the constant pull and push of an idea, a product, a strategy. The resulting confusion and frustration can quickly escalate to levels where it’s nearly impossible, even for the experienced, to see where they’re going. Intense settings such as Startup Weekend seem to aggravate the whiplash effect, given the short interval of time in which participants meet mentors firing pieces of advice in rapid succession.

While it’s a mentor’s duty to warn entrepreneurs of such dangers and suggest ways of wriggling out of them, the mentor whiplash phenomenon can also be turned into something positive. Take it as a learning opportunity. Accept the possibility that your own experiences are just that, your own, and they might not apply to others.

Tip Ask your mentees to summarize what other advice they have received. Is it radically different than what you would suggest? If so, rather than blindly pushing what worked well for you into someone else’s project, stop for a moment and analyze other people’s viewpoints. There’s usually more than one right way of doing something. Your job, as a mentor and advisor, is to guide, not to impose.

I am certain that there are many other ways in which mentors and advisors can learn from those they guide; I am barely scratching the surface here. What are some other opportunities for improving yourself and be a better mentor that you can share with us all?

Photo: Joshua Earle via unsplash.com