Getting Mentored Effectively

A Chinese manager of mine had a saying, “There are two types of people: introverts, and extroverts.” He watched over sales, hired friendly but aggressive extroverts, and although I can’t give props on ideology, the returns came in solid and steady. But damn, there were a lot of arguments. Mastering the art of networking can be very similar to sales: listen, relate, connect. Your killer network game doesn’t help when you’ve already made the inroads and now want to receive mentorship. So what does effective mentoring look like?

Know your goal!!!

You can’t get anywhere if you don’t know where you want to end up! Getting mentored means drawing on their past experience to improve your present. Boil down what you want to know or what you want to leave with. Maybe it’s people – a new connection or reference is a concrete thing you can walk away with. For a startup looking for investment, you may want to know what it’d take to get people coming to you for coffee. For one just growing, you may want advice on next steps to achieve a certain outcome. Now put it into one sentence.

The explorative, long-form sitdown chat is awesome. It’s where want want to be: bouncing ideas and riffing on approaches with Musk or Branson. But you don’t start with a whole Sunday to connect – you start with 15 minutes, if that. Make the most of it, have a goal – you’ll leverage it later.

Get your research in!!

Alright, chief, you got a game plan. Now review the playbook: for those you want to talk to, do your research!

You’re looking for something you can use to get to know them better or something they’re working on passionately: check out any YouTube speaker clips they might have put up from talks or conferences, a blog if they write one, and at least skim Twitter to get a feel for their style. Personality is a big player in how useful the interaction will be.

Look for matches between their experience and your goals. Are they masters of product, marketing, business leadership, or a tech ninja? Maybe they’re not in entrepreneurship at all – doesn’t matter. Know from what angle someone is most able to help. LinkedIn and CrunchBase/AngelList are good for this. If they’re investors, check through their portfolio – extra brownie points for referring to one of their companies and seeking to learn from something they did. You overachiever, you.

Ask specific questions!

“Well, what would you do in my situation?” – the worst question in a mentor-mentee relationship. Put your mentor in your shoes, and they come with the loaded baggage of experience, mindframes, resources, and probably a few tricks up their sleeves – likely few that you have. You want to do more than just get to know the way they think. You want to apply that thinking to your specific problem.

Not “Do you think this is a good idea?”

“What type of metrics would convince you we’re onto something?”

Not “What should we do next?”

“We’re trying to decide between A and B, which have X strengths/weaknesses. Which might make most sense if we’re trying to accomplish this specific goal?”

Ask questions you’ll find directly useful and actionable. Ask questions they’ll enjoy answering. Make it an intellectual exercise.

Listen – but guide the conversation

Absorb everything that’s giving you useful knowledge. Synthesize what was said for your own understanding and theirs. Then dig into it or move onto the next thing.

Challenge suggestions you want more clarity on or disagree with – if you’re simply nodding along, they’ll be as tuned out as you’ll be becoming.

Follow through, follow up

Useful advice, full notebook, back at your desk? Review and synthesize everything, meet with fellow team members to discuss if needed, but make sure you do something with the advice you’ve been given! You’re not going to get any smiles in coming back to a mentor without proof you’ve attempted to learn more about or implement a strategy. Bring work you’ve done, share what worked, what didn’t, and why. Return with more specific questions and a slightly more refined goal. But do return. A friendly email after the meeting is polite. Fill it with proof of what you’ve done since you last chatted, and you’ll have another meeting before you know it. Mentors love making an impact. Be that impact.

And don’t sweat it, you’ll be great.

I approached Boston unConference’s +100 mentor list, narrowed down those I wanted to talk to, guided the conversations with specific questions, and left with a follow-up plan after I had considered or implementation some suggestions. 20 minutes each with a CEO, a VC, and a Product Director.

The best moments of conversation were ones in which we interrupted each other because we couldn’t wait to jump on an idea. We cut off conversations about things we began to understand before the full thought was finished – to get to the next exciting thing. These mind flares are the sign you’re getting somewhere.

Even better? Leaving with questions unanswered on both sides. Few forces are more powerful than curiosity. Only have a silly 20-minute sitdown? Don’t cover everything – cover enough to get your value, and get them wanting to hear more. Keep on it. You may have just found yourself a mentor. You’ll be at those leisurely poolside chats with Branson or Musk mind melds before you know it.


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