“Can I pick your brain?”

No. Usually.

I get these requests all the time. And I am generous with free advice. Even so, how I respond is based on on where you land on two separate scales.

How specific are you?

“Can you help me with x?” is a lot different from “Can I pick your brain?”

The more specific your request, the more likely I am to want to help you.

Here are some requests to which I often say yes:

• “Can you help me define my book idea?”
• “Can you help me decide on a publishing model?”
• “Can you help me to figure out which of these book ideas are the most promising?”
• “How can I conduct consumer research on my idea?”
• “Should I work at Forrester Research?”

These are specific things I know about. I will turn you down if your specific requests are out of my expertise.

• “Can you help me with a social media strategy?” (No, I haven’d done that in 10 years or so.)
• “What did you think of the CES announcements?” (I didn’t go, thankfully.)
• “How should I evaluate a person I am trying to hire?” (I don’t know, I’m not an expert on that.)

I usually turn down general requests (but see the next section).

• “Let’s brainstorm where marketing is going.”
• “I want to catch up on the research industry.”
• “I’m at a crossroads in my career journey.”

How well do I know you?

I’ll go a long, long way for somebody I’ve worked closely with, either as a colleague or as a client.

I have some flexibility for people I’ve been connected with, even if they are not close friends.

I have very little interest in vague requests from people I’m just Facebook friends with.

How this goes together

Here are some queries I’ve devoted time to recently.

• “Can you help me with insights on how to succeed as a freelancer?” (Request from someone I’ve connected with frequently and productively over the last 10 years. I’m not an expert, but she deserves whatever help I can give.)
• “Can you help me decide which book to do next?” (From a client whose book I edited.)
• “How can coaching help me be a better writer?” (From a random blog reader, who is now a potential client.)
• “I’ve left my job — can we brainstorm some ideas?” (From a guy I worked with and respected as both a colleague and client.)

Here are some I’ve turned down.

• “Can we catch up?” (From a guy who worked where I did, but we didn’t interact much.)
• “Can you and I work together on a piece for my new blog?” (From a Twitter follower.)

What you should do

If you’re fielding queries, do what I do: balance how well you know the person against how specific they are. If you can help them briefly, do it. If they’re a friend, be more generous. (That’s just basic humanity.)

If you’re asking someone for help, research what they do. Then ask for help in a way that acknowledges that expertise and background, and with enough specifics that they would have a reasonable chance to answer.

We’re mostly not selfish. We’d like to help. And each time we do help, it means somebody else in the world who can refer us a good person to work with.

But that only works if you ask a question we know how to answer.