If you ask to “pick my brain,” I am probably going to ignore you. I’m not saying that to be a jerk or because I’ve suddenly decided I’m too important for the rest of the world. I’m saying it because that specific phrase has become a massive red flag for anyone who actually values their time.
It sounds harmless, right? It sounds like you’re being humble. You just want a little bit of knowledge. A little spark of insight. But what you’re actually doing is asking for a massive favor while offering absolutely nothing in return, not even the courtesy of a specific question. It is the professional equivalent of walking into a stranger’s house and asking to borrow their lawnmower, their gas, and their entire Saturday morning.
The rainy Tuesday in Seattle where I blew it
I know this because I used to be the person doing the picking. Back in June 2016, I was desperate to get into the tech scene. I found a guy named Mark on LinkedIn who was a senior engineer at AWS. He’d built some stuff I genuinely admired, and I thought the “proactive” thing to do was to reach out. I sent him a message: “Hey Mark, love your work. Can I buy you a coffee and pick your brain for 15 minutes?”
He actually said yes. We met at Victrola Coffee Roasters on 15th Ave. I bought him a $4.50 latte. I sat there for an hour and asked him vague, rambling questions like “How do I get started?” and “What do you think the future of the industry looks like?” I thought we were having a great time. I felt like I was “networking.”
I wasn’t. I was being a leech. I could see his eyes glazing over as he realized I hadn’t done even ten minutes of research before showing up. I was asking him to do the heavy lifting of my career for the price of a cheap coffee. I never heard from him again. I sent a follow-up email a week later and got total silence. I didn’t just fail to network; I actively burned a bridge by being unprepared. It felt like garbage.
Actually, let me put it differently—it wasn’t just that I was unprepared. It was that I was being lazy. I wanted him to summarize his twenty years of experience into a neat little package because I didn’t want to go through the messy work of figuring it out myself.
The brutal math of the “Coffee Chat”
I’m going to be honest about something that might make me sound like a snob, but I don’t care. I genuinely think people who send “can I buy you a coffee?” invites are often the most entitled people in the professional world. You are asking for an hour of someone’s time—which, if they are a consultant or a high-level pro, might be worth $200 or $500—and you’re offering a $5 beverage. The math doesn’t work. It’s an insult disguised as a gesture.
I actually tracked this for my own blog last year. I looked at 42 different requests I got for “quick chats” or “brain picking.”
- 39 of them were vague requests with no specific goal.
- The average time requested was 30 minutes, but they always try to go over.
- The response rate I gave to the “brain pickers”? Exactly 0%.
- The response rate I gave to the 3 people who asked one specific, 2-sentence question? 100%.
I might be wrong about this, but I think the rise of “inbound marketing” and tools like HubSpot have poisoned our brains. We think that everyone is just waiting around to provide “content” for us. But real people aren’t lead magnets. They have lives and deadlines and kids who need to be picked up from soccer practice. Asking to pick someone’s brain is like asking a chef for a “quick tour” of the kitchen while they’re in the middle of a Friday night dinner rush. It’s selfish.
Information isn’t a faucet you can just turn on; it’s a battery that drains when you short-circuit it with bad, open-ended questions.
Anyway, I’m getting worked up. I should probably mention that I also have a weird, irrational hatred for people who use Calendly for their personal lives. If you send me a link to “find a time on my calendar” for a casual catch-up, I’m probably never talking to you again. It feels so transactional and cold. But I digress.
How to actually get a “Yes” without being a parasite
If you want to talk to someone you admire, you have to stop being vague. Vague is work. Vague requires the other person to figure out what you need. Instead, you need to do 90% of the work before you even hit send.
I used to think being “available” was a virtue. I was completely wrong. It just makes you a target for people who don’t value their own time. Now, I only respond to people who show they’ve done the reading. If you ask me a question that can be answered by the first page of Google, you’ve already lost.
Here is the formula that actually works. It’s short. It’s blunt. It works.
- State exactly who you are in one sentence.
- Mention one specific thing they did/wrote that actually helped you.
- Ask ONE specific question that can be answered in under three minutes.
- Give them a “no-pressure” out.
That’s it. That’s the whole trick.
I once reached out to a writer I really liked—this was maybe two years ago—and instead of asking for a “chat,” I just said: “I read your piece on why most newsletters fail. I’m struggling with my open rates on Substack (they’re stuck at 22%). Do you think it’s the subject lines or the frequency?” He replied in ten minutes. We ended up emailing back and forth for a month. No coffee required. No brain picking. Just a real conversation between two people who care about the same stuff.
The uncomfortable truth about “Networking”
Here is the take that usually gets me in trouble: Most people don’t actually want advice. They want permission. They want someone they admire to tell them that their mediocre idea is actually great so they can feel better about not starting yet.
I refuse to be that person for anyone. I’ve become very protective of my time, to the point where I probably come across as cold. I’ve had people call me arrogant because I won’t “hop on a quick call” to help them with their startup idea. But the truth is, if your idea is so fragile that it needs a 20-minute pep talk from a stranger to survive, it’s already dead.
I’ve bought the same $120 notebook—the Leuchtturm1917, specifically the A5 dotted one—six times in a row. I don’t care if there are better ones out there. I like the consistency. I feel the same way about my network. I’d rather have five people I actually provide value to than 500 “connections” who only reach out when they want to suck some information out of my skull.
The quality of your network is directly proportional to how little you ask of it and how much you contribute to it. If you’re always the one asking to “pick,” you’re not a networker. You’re a mosquito.
I still feel bad about Mark in Seattle. Sometimes I think about finding him and apologizing, but that would just be another request for his time, wouldn’t it? Another way to make it about me. So I just stay quiet and try to be better for the next person who emails me.
Do you actually have a specific question, or are you just looking for a shortcut? Honestly, I don’t know the answer for you. But I know which one gets a reply.
Stop asking for coffee. Start doing the work.