There’s a peculiar paradox in professional relationships that most people get backwards. When you need money—whether it’s funding for your startup, a job opportunity, or a business deal—your instinct might be to ask for exactly that. But here’s what actually works: ask for advice instead.
This isn’t some manipulative trick. It’s rooted in basic human psychology and the way professional relationships actually develop. When you ask someone directly for money or a job, you’re putting them in an awkward position. They have to evaluate you immediately, often with limited information, and the interaction becomes transactional. Most people will say no, not because you’re unqualified, but because they don’t know you well enough to take that risk.
But when you ask for advice, something different happens. You’re acknowledging someone’s expertise and experience, which people generally enjoy sharing. The conversation becomes collaborative rather than extractive. They’re not being asked to make an immediate commitment or pull out their checkbook. They can simply talk about what they know.
Here’s where it gets interesting. As people give you advice, they become invested in your success. They’ve spent time thinking about your problem, offering suggestions, sharing their perspective. Psychologically, we tend to like and support the people we help. It’s called the Ben Franklin effect—after you do someone a favor, you’re more likely to do them another favor in the future because you’ve already categorized them mentally as someone worth helping.
More practically, when you ask for advice, you’re getting something immediately valuable: information, perspective, and often introductions. The person giving advice might mention someone else you should talk to, or a resource you should explore. These connections compound. Each conversation opens new doors, and some of those doors lead directly to the opportunities you’re seeking.
The money or opportunity often follows naturally. Once someone has advised you, watched you implement their suggestions, and seen you’re serious and capable, they’re far more likely to invest, hire, or recommend you. You’ve built a relationship rather than making a cold ask. They’ve seen how you think, how you take feedback, and how you execute. You’re no longer a stranger asking for something—you’re someone they know and have already helped succeed.This approach requires patience. You can’t ask for advice on Monday and expect a check on Tuesday. But that’s actually its strength. The relationships you build are genuine and durable. The people who eventually invest in you or hire you do so because they actually know you and believe in what you’re doing.
Of course, this only works if you’re genuine. Actually take the advice seriously. Follow up and let people know what happened. Show them their time was worthwhile. Ask thoughtful questions that demonstrate you’ve done your homework. The goal isn’t to trick anyone—it’s to build real relationships with people who can genuinely help you, and whom you might be able to help in return someday.
The next time you need funding, a job, or any kind of opportunity, resist the urge to lead with the ask. Instead, identify people who’ve been where you want to go, and ask them how they got there. Ask what they’d do in your position. Ask what mistakes to avoid. You might be surprised how often the conversation ends with “let me introduce you to someone” or “actually, we might be able to work together on this.”
The money you’re looking for is usually on the other side of a relationship. And relationships don’t start with transactions—they start with conversations.
