help signEven the most successful people get stuck sometimes, and in these moments, advice makes all the difference. From life to love, business, and health, the insight of others is invaluable.

Consider the case of Andrew Lee, a young entrepreneur who sold his startup, JamLegend, to Zynga in April 2011. When facing new business ventures, his team of mentors helped him persevere, as he explained in a recent interview:

“Our investors had great industry experience. It’s not often that you find people who understand what you’re going through,” Lee said. “They were instrumental when we were acquired. They helped us understand negotiations and how to do the negotiations right. They had been through more of this than I ever had.”

Advice is an asset that we must actively pursue, but what’s the best way to reach out to a casual acquaintance or complete stranger? The reality is that most people are terrible at asking questions. It takes an approach that is both a science and art. Ask the right questions, and communicate what you need – here’s how:

1. Keep it streamlined.

Mark Suster is a venture capitalist who focuses on early-stage startups. In addition to his position as Partner at GRP Partners, the largest VC firm in Southern California, he’s an angel investor, business school board member, and founder at a mentorship program to help young startups get funded. Long story short: he has a lot going on, but he likes to help people.

Entrepreneurs ask him for advice all the time, and he’s noticed one common mistake:

“In today’s era, we’re all asked for help, favors or introductions all the time. Most of us want to help. But many well intentioned entrepreneurs are sloppy about how they ask,” he said.

When asking for advice, you need to assume that your contacts – while wanting to help—are super busy. You want to provide them the resources to process information as quickly as possible. Suster recommends keeping messages short and focused. If you need to send additional information, include an index or PowerPoint deck.

2. Think “question” instead of “questions.”

When entrepreneur/blogger Leo Widrich began building his projects, he found himself needing advice. Reflecting on his past experiences of reaching out to others, he explains his key mistake – a lack of clarity.

“I used to pour out my life story to everyone I thought might be able to help me with a little bit of advice. Dozens of sentences involving what I am doing, no clarity at all, and no question at the end, apart from a vague ‘What are your thoughts?’” Widrich said.

Then, Widrich received a response that transformed his approach: “Can you send 1 short specific question?” from Noah Kagan of Appsumo.

To advice-seekers, Widrich recommends sending four sentences at most. The first two or three should be words of honest appreciation. The last sentence should be a focused question.

Beyond the benefit of presenting yourself well, you’ll be forcing yourself to think about your problem with more structure.

3. Leverage social media.

Social media bridges communication gaps.

One example, HealthTap, is a social platform where doctors give patients advice for free. Another example is Q&A engine Quora, which attracts business leaders and educators.

Consider the experience of Nikila Srinivasan, a recent grad who was curious about a career in product management. By following the product management topic on Quora, she connected with Jeff Eddings, a product manager at StumbleUpon. Now, Nikila reports to him as an associate product manager.

“Thankfully, my now-boss, then-Quora connection Jeff Eddings turned out to be very approachable and willing to answer a million questions from an eager wannabe product manager,” Srinivasan said.

4. Pay it forward.

Make an effort to give as much as you get. Find a way to help the person who is helping you, and try to make yourself available to others. Keep the ecosystem balanced.

This post originally appeared on the author’s blog.

Canadian Dan Martell is CEO/Founder of, Co-Founder of Flowtown (Acquired ’11), Founder of Spheric Tech (Acquired ’08), Mentor @ 500Startup. Investor in many.

The Young Entrepreneur Council (YEC) is an invite-only organization comprised of the world’s most promising young entrepreneurs. In partnership with Citi, the YEC recently launched #StartupLab, a free virtual mentorship program that helps millions of entrepreneurs start and grow businesses via live video chats, an expert content library and email lessons.

Photo By: marc falardeau