How to Ask to Pick Someone’s Brain—Without Being Annoying

When you reach out to people you admire, asking them to chat about their careers, you probably think it’s an obvious decision for them to help you. After all, who doesn’t want to use their hard-won expertise to catapult other people to success?

Well, I’ve got some bad news for you: Agreeing to meet up with you is not an easy decision for these people. In fact, in many cases, they would much rather say no.

It’s not that they’re heartless and don’t want to help, it’s just that they get a lot of these asks. You’re not the only one who wants their advice! And, unfortunately, they only have so much time to give away. In fact, the New York Post reported this week that some experts are starting to feel so taxed by the asks for help, that they’ve started charging for it (and not just the price of the cup of coffee you’re offering to buy them).

So, what can you do if you really want some guidance from someone you admire? Follow the five-step process below for asking someone busy for help—without being annoying—and you’ll make it hard for him or her to say no.

1. Soften Them Up

Obviously, people are generally more willing to help a friend for free than a stranger. So, you should start by making this person like you! If you have any connections at all, take full advantage of them. Use LinkedIn to see if you have any mutual contacts, or email your network to see if anyone knows this person. Then, if you do have anyone in common, see if they’d be willing to intro you (and vouch for you in the process).

Of course, this isn’t always possible, in which case, make sure to start your message by explaining why you’re reaching out to this person specifically, as opposed to any number of the other experts in the field. It could be something you have in common (“I noticed you went to American University as well—go Eagles!”), some work of his (“I heard you speak at the World Business Forum on Innovation recently and was really struck by what you had to say”), or something specific about her experience that draws you to her (“I know that you successfully transitioned from marketing to editorial, a move I am currently trying to make”). Even a small connection can help you stand out from the other dozens of messages in someone’s inbox.

2. Don’t Suggest a Coffee Date

Somewhere along the way, asking to “sit down for coffee” became the status quo for requests like this. In some ways, it makes sense—it’s shorter than lunch, more professional than drinks—but when you really think about it, it’s not that convenient for the person you’re asking. When you count the time commuting, ordering coffee, sitting down and making small talk, and actually answering your questions, most coffee dates will take almost an hour. And that’s a lot of time to give!

Instead, ask for something that’s even easier. Suggest a phone call—it’s often more void of small talk than coffee, and your contact can do it from anywhere. If you really want to meet in person, offer to stop by his office and meet. Or, go somewhere she will already be—ask if she’ll be attending an upcoming industry conference or networking event and suggest you chat there (as a bonus, you may get introduced to other people, too).

3. Say How Much Time You Need (and Don’t Ask for Much)

In your email, you should say exactly how much time you need (and not ask for more than 15 minutes, 20 tops). If you just generically ask for time to talk, people may assume the worst and think it will take an hour of their valuable time. But prime them with a number, and suddenly it doesn’t sound like so much to give. A simple, “I’d love to hop on the phone for 10 or 15 minutes sometime in the next couple of weeks!” works perfectly.

As part of this, be prepared to be flexible with your time. If you really want someone’s help, you’re not exactly in a position to say, “I can only talk during lunch or after 6 PM.” Offer to meet whenever works for your contact, and if he responds and says he has time, but only at 8 AM—do it.

4. Make Your Ask Really Specific

Similarly, you should be very specific about what you want to talk to this person about. Vaguely saying “I’d like to talk to you about your career” sounds huge and may make your contact think this is going to take a lot of brainpower. But by saying, “I’d love your thoughts on how you successfully turned a freelance writing gig into a full-time position,” she’ll likely realize how little effort she’ll have to put into helping you out.

5. Be Grateful

In other words, use your manners! Even before this person has agreed to talk to you, mention how you know his time is valuable and that you really appreciate him considering chatting with you.

You can even offer to do something in return. Try: “I really appreciate you considering sharing your time with me, and if there’s anything I can do in return, please let me know.” Even if your contact doesn’t need anything from you, it shows that you’re willing to give a little, too.

A final note: You want your ask email to be short and sweet, so you should pack all of this into no more than five or six sentences. You don’t want this person to waste all his or her time on you just reading your email!

And remember—if you’re friendly, accommodating, and maybe even a little flattering, people will generally do their best to help. You won’t always get a yes, but you’ll definitely have a better chance of leaving the right impression.

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