Have you finally dedicated yourself to starting a side hustle or launching your dream business? Good for you — taking that leap is courageous and inspiring. Now that you’re on your way, you’re sure to face a series of milestones and challenges, including some that may be more than you or your mentor are capable of figuring out on your own. Though it’s awesome to find the confidence to approach a professional you admire, investor and author J. Kelly Hoey recently told us why you should never ask someone if you can “pick their brain.” Turns out, doing so is not a compliment; it can be a career-killer!

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“Asking to pick someone’s brain over coffee to gain advice or form a relationship is actually likely to put a kibosh on the possibility,” Hoey explains. “For me, a ‘pick your brain’ email signals a lack of prep for any sort of real meeting or ongoing email exchange. Even more, it shows disregard for the value of time and hard-earned expertise.” Yikes! So what to do before you enthusiastically fire off a message asking to connect in hopes of gaining insight into anything related to your career or business? Hoey instructs us to remember the following points:

1. You can find basic information somewhere else. You’re likely reaching out because the person you’d like to chat with has a successful track record. Maybe you run in the same professional circles, have mutual friends, or have noticed them on social media. In any instance, Hoey suggests sifting through info available publicly instead of asking for a nonspecific meeting. “Answer your own questions on their remarkable career path and educate yourself on what they’ve actually done, in detail.” She tells us that while reading all that info, you’ll probably discover how they actually like to be contacted and share career advice.

2. Your question has probably been asked and answered before. “The person you want to speak with likely has a point of view — which is why you want to talk to them, of course — so sleuth around beyond the one article or tweet that sparked your interest in talking to this person,” Hoey advises. “Do they blog, vlog, or contribute regularly to a publication? Read and watch all of this!” For even more clever insights, Hoey recommends reading The Pop-Up Paradigm ($16) by Melissa Gonzalez, who wrote her book after receiving endless requests to meet for coffee.

3. Experience should be valued. Since you’ve already started working on your side hustle or business, you know how much persistence and dedication launching a new endeavor takes. “This plays a big part in career success,” Hoey reminds us. “Drop the notion that a chance meeting over lunch or sprinkling of career fairy dust will… transform your trajectory.” What to do instead? “If you value someone’s insights, value the time they’ve invested in their career too. Are you asking for a coffee date as a way to avoid paying the real price for the person’s knowledge? If so, you’re not only undervaluing them, but also how much you value your own career. To learn, know what the person offers — such as an online course, hourly coaching option, or weekend bootcamp — and consider signing up. Or, if the person you admire speaks frequently, consider attending, and have your ‘pick your brain’ question ready for the Q&A session after their formal remarks.” Great advice!

4. Time is precious and limited. “Our two most valuable assets in life are reputation and time,” Hoey explains. “Reputation is earned through the work we produce combined with how we interact with others to get stuff done. Reputation is built (and reinforced) over time — and while it can be lost, with time we can earn it back.” She reminds us that time itself, on the other hand, is limited. “It might be a 24/7 world, but that’s the irony: There are only 24 hours in a day.” Asking for a brain-picking session doesn’t value someone’s time like the priceless commodity it really is.

Still have a burning question that hasn’t been answered through your superb online sleuthing or other attempts? Hoey tells us that sending an email with a super-specific, thoughtful question is completely okay. She even gave us some suggested language that’ll help you make a smart and professional impression right off the bat: “I’ve read through your posts on Medium on switching careers and watched your interviews and TED talks. My specific question relates to… Can you direct me to an answer? I suspect you’ve been asked this many times before, and I might have missed the post in my research.” Perfect!

5 Ways to Respond When Someone Wants to Pick Your Brain

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On the flip side, now that you’ve started work on your own venture, you might receive your own requests for brain picking! If this is the case, Hoey prepped us with five considerate responses you can use instead of ignoring a message from someone who wants your help. To save yourself even more time, set up templated email responses you can use with an email tool like Streak for Gmail (it’s a game-changer).

1. Be gracious. Hoey suggests saying something like, “Thanks for reaching out! It’s a huge compliment to receive requests like yours,” before re-directing the requester to a resource or letting them know you’re unable to share the info they’ve asked.

2. Acknowledge their question. Try something like, “I get this question a lot; it’s the reason I wrote this blog post,” with a link. It’s simple and straightforward.

3. Decline and politely redirect. Though declining can feel like a difficult thing to do, Hoey suggests a way to handle it: “The best place to find me in person is at one of my upcoming events listed on my website.” Tailor your response so it fits your biz and schedule, and you’ll be good to go.

4. Educate with extra info. See the request as a great opportunity to further educate someone who admires what you do. Have a newsletter? Let ‘em know they can sign up to receive additional tips. Do you regularly author blog posts for a specific site? Link to your column so it’s easy to stay in the loop.

5. Find other ways to be helpful. You might not be able to help everyone personally, but you can always share your favorite reads and resources. Hoey offers a message such as, “If you’re really interested in switching careers, you may also want to read X or join Y.”

How do you approach people you admire for advice? Share your tips with us on Twitter @BritandCo.

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