Startup Mentoring Sessions: How to be a decent, maybe even good startup mentor.

Dec 4, 2012 · 7 min read · 3,768 views

How to be the perfect startup mentor? I don’t know. But following the best practices mentioned in this article I got personally at least to the “not-so-shitty” level. I am happy to share my notes and hope there are some take-aways within for you as well.

The guys of TL;DR at Seedcamp Paris

_This blogpost is about mentoring session formats as you see in most incubators, startup weekends or acceleration events. Startups own a table, mentors circle in groups from startup to startup. This post is part of a two-blog series about this topic. This time I am focusing on the mentor’s side of the table. But good Mentoring is about both sides of the table. And while both sides are equally as likely to f_ck it up – wrong mentor’s advice can easily result in long-term damage for the startups.*

Checklist for First-Time Mentors…

1. Attitude

You are an industry veteran. Damn… all the things you have seen, the stories you can tell. You did startups before it was cool. You have been up and down the startup roller-coaster several times, you are experienced. You have been picked by all the best - mentored at Seedcamp and Ycombinator… The kids nowadays have it so easy and still they are so arrogant… Don’t recognise your experience… You have been to the field…… You are like the rambo of startups, battle-scared to the bone, loaded with a machine gun of advice, ready for destruction…… Cut that crap.

The true A-players in the world are humble and open.You don’t have to proof yourself to no-one and you know that there is always someone better out there. Be a true A-player, don’t play one.

Even if startups don’t respect your experience or disregard your advice, stay positive. Ignore their ignorance and take is as a sign of their potential – good founders are often stubborn idiots in their early days. Keep the good spirit and stay kind and helpful, all the time.

2. Pick your weapon of choice.

You are experienced in several things, that’s good, but don’t try to be jack of all trades. Nobody needs your 0,2cents about everything, they need the big-buck stuff. Focus on your strengths and be the experts for these topics.

If you are not an expert for a given topic and you have nothing to add that helps 10x - just keep silent or refer to people that might be able to help and let them move on to the next question. If they insist to get your advice make sure they are aware that this is just an opinion not based on own experience. You are not there to answer all questions, you are there to answer a few questions really well.

Pro-tip: Have links ready to the ressources you anyway mention all the time. Be ready to give these links (or search term) right at the venue.

3. Listen & Understand it from their point of view.

The number one thing startups complain about their mentors is that many are incapable to listen (thus truly comprehend). Sometimes a mentor believes to have a better idea about what they startup should do, no matter what they want to do. They complain that many mentors just try to force a conversation to their topic or opinion. Very often mentors rush into answers after hearing half the problem, because they want to get an idea or story that just came to mind of their chest. Don’t be that kind of mentor.

Never rush into answering
Listen patiently
Write your thoughts down
Give them one focused answer
Walk them through and catch them where they are
Show empathy and understand their point of view.

Empathy requires something extremely difficult: accepting the fact that we are not and never will be in the other person’s shoes. There’s no rational, universal course because individuals have different goals, different worldviews and different experiences. – Seth Godin

4. Do ask, don’t tell.

Don’t push your knowledge on the founders, instead focus on asking the “right” (slow) questions and help them to get their thoughts forward.

“Tell me and I forget. Teach me and I remember. Involve me and I learn” – Benjamin Franklin

I highly agree with Fred Destin, who advocates using the socratic way for startup mentoring.

Additionally there is one book i would like to highly recommend everyone to read. And when I say everyone I mean everyone who interacts with other human people. For me personally (as a half-social geek) it is one of the most important books I ever read.

How to Win Friends And Influence People – Dale Carnegie

5. It’s not You VS Them, It’s You AND Them

There is a tendency of mentors trying to “ask the really hard questions” or “roasting” or “judging” them. That’s not what it is about.

“So… what is your revenue model and how are you going to scale it?” - other mentor

“Really…? Really? Of all the problems they have right now, this is your question?” - Stiar Tali

Focus on topics that are actually providing value to the startups right now.

Be aware of their current stage of company/concept maturity and adjust accordingly.
Focus on stuff that’s problematic and actionable for them right now.
Be as honest as you can about problems you see, no need to fluff it.
Help them see upcoming challenges and risks.
Help them to see common mistakes in their approach/structure/patterns.
Look for analogs or antilogs of other companies (eg ask about failed companies or competitors in their space) and see what they can learn from them.
Never get them defensive that’s when they stop learning.
Very important: Don’t share opinions, share experiences.

I highly recommend @destraynor’s post as a starting point on how to find great questions.

6. Learn to let go.

Some founders are just very early in their personal progress. They are “visionary” first-time founders, all over the place, ignorant and super cocky about it.

No matter how spot on your advice is - if the team doesn’t pick it up, there is no way you can make them.
No matter how big their potential startup idea is - if the team is not “ready” they won’t get nowhere.
Sometimes your advice is just plain wrong, but don’t know it yet.

Just accept it and move on. It’s not your obligation to force-feed anyone to success.

7. Always leave on a positive note.

Mentoring sessions tend to focus on the negatives, the things that don’t work, the stuff take will kill the business. And believe me speaking for hours about the problems of your company makes you regret ever starting that damn thing.

Always try to mention the things you like throughout the session, but especially leave on a positive note. Finish the session by saying what you really like about their business/startup. It will leave the whole mentoring session in a positive light.

Exchange contact details and offer direct actionable help. Always offer to send intros if you think you know people that can help them.