Twenty years ago, I was right there—hustling, grinding, trying to figure out how to get from Point A to Point B in my business. I was juggling everything: late nights, side gigs, unpaid work, and a dream that felt both alive and exhausting at the same time. I vividly remember sitting across from people who were further down the road than I was, full of questions, hoping they’d help me navigate the unknown. And honestly, most of the time, I didn’t even know what to ask—I just knew I needed help.
That’s why I get it. I get the urge to reach out and ask, “Can I buy you a coffee and pick your brain?” It comes from a real place. You see someone who’s further along, someone who seems to have the answers, and you want just a sliver of their insight. You want to skip the mistakes they made, maybe find a shortcut. I know, because I’ve been that person.
But now, 20 years into this journey, the tables have turned. My time—like yours—is packed to the brim with commitments. Between work, family, friendships, and those few precious moments I get to myself, I’ve had to learn to protect my time like it’s my most valuable resource. Because it is.
It’s not that I don’t want to help—I do. I love sharing what I’ve learned, hearing someone else’s dreams, and helping them make sense of the chaos. But when the invitation is framed as, “can I pick your brain?” or “can I buy you a coffee?”—it often comes across as undervaluing what’s being asked for.
So here’s the deal: if you want to connect with someone, especially someone who’s built something you admire, there are better ways to approach it. Ways that are more thoughtful, more effective, and that respect both parties’ time and energy.
Here are 5 ways to engage someone without asking to “pick their brain”:
1. Do Your Homework
Before you reach out, research the person. What have they written about? Where have they spoken? What projects are they working on? Showing that you understand who they are and what they value makes it clear you’re not just firing off generic requests. A well-researched question gets better answers.
Example: “I saw your recent blog post about X, and it really resonated with me. I’m struggling with something similar. Could you share how you tackled Y?”
2. Be Specific
“Can I pick your brain?” is vague and overwhelming. What are you really looking for? A piece of advice on marketing? Help figuring out cash flow? Insight on hiring? Be clear about what you need—and keep it short and focused.
Example: “I’m launching a business and struggling to attract my first customers. If you have 10 minutes, could you share how you approached that in your early days?”
3. Offer Value First
Relationships work best when they’re a two-way street. Even if you feel like you have nothing to offer, think about how you can be helpful. Maybe you know someone they’d want to meet. Maybe you’ve seen an article or tool they might like. Or maybe it’s just about offering genuine gratitude and enthusiasm for their work.
Example: “I loved your talk at [Event]. I shared it with my network because I think more people need to hear your message.”
4. Respect Their Time
Instead of asking for a coffee meeting, ask for a small, manageable amount of time—like a 10-minute phone call or a response to a quick question. Make it clear that you understand how valuable their time is.
Example: “I know you’re busy, but if you have 10 minutes for a quick call, I’d really appreciate your advice on X. If not, no worries!”
5. Be Patient and Gracious
Not everyone will be able to say yes—and that’s okay. If they can’t meet, thank them anyway. If they do give you their time, show up prepared and follow up with gratitude. And most importantly, implement the advice they gave you.
Example: “Thank you so much for taking the time to chat. Your insight helped me see things differently, and I’m already working on [specific action you took].”
When you approach someone thoughtfully and with respect, you’re far more likely to get a positive response—and maybe even build a real, lasting connection. Because at the end of the day, we all remember what it felt like to start out. We remember the struggles, the unknowns, and the people who took a chance on us.
So here’s my ask: Don’t undervalue yourself, and don’t undervalue the person you’re reaching out to. Be specific, be kind, and respect the journey they’ve been on.
And remember—you can buy your own coffee. 😉
About the Author
Matt Frary is a serial entrepreneur, growth strategist, and leader in the partnership and affiliate marketing industry. Armed with an MBA from Thunderbird School of Global Management and over 25 years of experience, Matt has successfully founded, scaled, and sold multiple companies, including SmarterChaos and ROI Rocket. As the founder of Chief of Chaos, Board Chair for Colorado Companies to Watch, and an advisor to Iterate.ai, Matt is dedicated to helping businesses grow with clarity and purpose. His contributions have earned him numerous accolades, including recognition in the Inc. 5000 Fastest Growing Companies and the Colorado Technology Association’s APEX Award for Most Innovative Entrepreneur. When he’s not building businesses, Matt can be found spending time with his family, working out at The NetWORK, or cheering on his kids at sports and equestrian events.