How to Reach Out to a Stranger for Career Advice

This article originally appeared on Live in the Grey.

We’ve all been in this situation: you find out about some amazing human being who embodies everything you admire and aspire to be. Suddenly, all you want is to meet this person, to absorb their awesomeness and maybe have some of it rub off on you. You feel like they could teach you so much about life and work and success. But how do you actually make this a reality?

The problem is that, often, people like this are incredibly busy and get many similar requests. So you really have to stand out (for the right reasons) if you’re hoping to get a second of their time.

Having been on both the giving and receiving side of the random-reach-out, and observing how higher profile people filter such requests, I’ve learned a few lessons about what does and doesn’t work. So that your requests don’t fall on deaf ears, I’m sharing those lessons with you. Here’s how to increase your chances when you ask someone for their time:

1. Getting introduced in person > Everything else

The best possible way to catch someone’s attention is to get introduced by someone that they know and respect. It will lend you immediate credibility in their eyes. As annoying as the old adage “it’s all about who you know” may be, it makes a lot of sense. Think about it: if a friend or trusted colleague asks you to meet with a smart, capable friend of theirs who so excited about you, how likely are you to say no? It’s much harder than saying no to an unsolicited email. If you’re not in the same friend group as this person (which is likely the case), consider if you know anyone who works at the same company. LinkedIn is an indispensable tool for finding any second-degree connections within your professional network.

The second thing to know is that if you can be introduced in person (at a networking event, social gathering or other casual setting), you’re sure to at least get a little conversation time in (and hopefully build upon the moment to get a full fledged coffee date). If you can’t get an in-person introduction, having your friend let them know in person and following up in an email trumps an email-only introduction trumps a social media introduction.

2. Choose wisely

I mean, listen, any human alive would probably benefit from a meeting with Beyonce or Bill Gates or Michelle Obama. But what you really want is to find someone who speaks to your own journey in a personal way. Choose someone whose path you can relate to (and therefore, someone who will be able to relate to your path). Not only will this help you narrow down your options to people who are a little more attainable and likely to be in your network, it will also help you with tip #3.

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3. Find common ground

When someone gets an email or a message from you, you will begin as a mere group of words among a thousand other things on their mind. It’s your job to become a tangible and interesting person to them as quickly as possible. The best way to do this is to share things you have in common with someone. This also becomes part of the reason you’re reaching out to them. It could be that you’re both passionate about the same cause; or have a similar background; or are part of the same community; or participate in the same organization; or attended the same school, camp or fitness class; perhaps you just both worship the same musician.

The more someone can see themselves in you, the more compelled they’ll be to respond. It’s great to get specific, but so you don’t come off as stalker-y, be sure to explain where you learned your specific information.

4. Provide value: Have something to say or share

If you really want to increase your chances of getting someone to pay attention to you, you have to prove to them why it’s worth their while and not just yours. There are kind and available souls out there who get a lot out of simply giving advice, but that won’t always be enough. Did you recently learn about a great resource for your shared industry that you could introduce them to? Are you part of an organization that would be of interest to them? Is there a conference you think they would be a great speaker for? Did you write a blog post on what you admire about their company?

Providing them value doesn’t necessarily mean they’ll immediately get something out of what you share, but demonstrating that you want to give and not just take will make a big difference.

5. Make your flattery specific and personal

We all love being flattered, but simply piling on the ‘you’re so great’s’ can feel disingenuous or self-seeking. To get beyond this impression, first, be specific with your praise. Tell them about the line that resonated with you in their most recent article for Mashable, or about the brilliant innovation in their work project. Second, pair your praise with candor. Don’t try to overwhelm them with positive accolades, but instead tell them how you honestly feel and make it personal.

So, instead of “I think you are such an amazing creative director,” try “More than any other creative director, your work really speaks to me. Your recent holiday campaign really blew me away. I think it’s a combination of the emotional sensibility you bring to projects and your work ethic. They’re traits I aspire to improve in myself, and I appreciate having someone to look up to.” See the difference?

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6. Don’t be vague about what you want

The worst trap you can fall into when reaching out to someone is having them suspect that you secretly just want a job or a favor you aren’t divulging. Make sure that you are clear about your wants and expectations, but don’t force someone into a corner before ever having met. That’s not to say you can’t ask for something further when your meeting goes well. But at the outset, stick to asking for time and offering value.

7. Create an agenda to get the most out of your meeting

Once you’ve actually gotten your coveted meeting, prepare, prepare, prepare. That means researching the person you’re meeting, companies they’ve worked for, news about your common industry or organizations, and whatever else might be relevant. Then, craft an agenda that you can easily refer to if the conversation runs dry or gets awkward. You most likely wont have to refer to it, but the process of making it will help you keep great topics of conversation top of mind.

8. Express your passion

People love other passionate people. It’s exciting and contagious to be around someone who exudes energy when you get them started on their interests. So be sure that your passion for your own goals and interests comes across loud and clear. Whether it’s being able to delve into a topic or showing some of the work you’ve done that shows your commitment, if you demonstrate that you care others will care.

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9. Follow up quickly

After your meeting, if things went well (or even if they didn’t), be sure to follow up by the next day to thank them for their time. If there was an article you promised you would share or a connection you said you would make, be sure to do that. And keep the door open for future interactions. When you get a response, connect with them on LinkedIn, Twitter and other social networks to keep in touch.