The Coffee Conversation

Several weeks after my first layoff, I felt stuck. I was spending hours looking for jobs, tailoring my resume, and hitting “submit” on roles that looked promising. But nothing was happening. The process felt mechanical. I was doing the work, but I wasn’t making progress.

A role eventually came up at a company that I had a professional acquaintance at. Instead of dropping another resume into the void, I sent him a message and asked what he knew about the team. A couple of exchanges later, he offered to introduce me to the hiring manager.

I could have sent my resume right then. But instead, I asked if she’d be open to grabbing a coffee. No pitch. No pressure. Just a conversation to learn more. Fortunately, she said yes.

She told me about the work, the team dynamics, the challenges they were facing. I wasn’t trying to sell myself (yet)... I was listening and relating. By the end of that coffee, we were becoming friends. I was a person she knew, someone she could advocate for. And guess what? I landed a role on the team.

That single cup of coffee changed the trajectory of my career.

The reasonable, but unnecessary, hesitation.

The first is small talk. People say, “I hate small talk. It feels so awkward.” But small talk is human talk. It’s where you connect with someone on life outside of work. It’s how you find out they just sent a kid off to college, or that they’ve been training for a half marathon, or that they tried a new restaurant in town. Those seemingly throwaway details are what make a conversation memorable. They are the connection.

The second hesitation is the fear of putting someone out. We tell ourselves, “They’re too busy. I don’t want to bother them.” But here’s the thing: people like to help people. If you’re thoughtful, if you accommodate their schedule, if you keep the time commitment reasonable, if you pick up the coffee, you are not putting them out. In fact, you’re giving them a chance to do something that most people find satisfying: share advice, offer perspective, or feel useful to someone else.

The third hesitation is not knowing what to say. That anxiety is real, but the solution is preparation. You don’t need a script. You just need to know the essentials—where you’ve been, where you’re going, and why you wanted to connect with this particular person. That’s reasonable homework for what could be a life-changing door.

When you move past those hesitations, you see why coffee works.

The humanity in coffee.

From a job search perspective, a good friend of mine set himself a weekly goal of twenty informal meetings (mostly coffee chats) after being laid off. Over time those conversations made him visible and memorable, which landed him a dream job with a great company.

From a growth perspective, another friend who was laid off turned 'grabbing coffee' into a project... committing to having one hundred coffees with friends and professional connections. His objective? Learn from others. When we had our virtual coffee, he had a spreadsheet of the lessons learned from every conversation. And now he's writing a book about the project.

From a community perspective, my other friend started a program called One Million Cups to ignite entrepreneurial communities across the country. The mission was to host weekly coffee gatherings for entrepreneurs and supporters to engage and collaborate. This program took off because people craved connection.

These aren’t flukes. Sociologist Mark Granovetter famously wrote about the “strength of weak ties.” Your closest friends and colleagues know many of the same people you do. But acquaintances (at the edge of your network) often connect you to opportunities you’d never find otherwise. Coffee conversations bring those weak ties to life.

Broader and Deeper Connections

Here’s how you can put this into practice:

Reach out to someone you already know. A former colleague. A manager you worked well with. A friend you haven’t caught up with in years. You’ll be surprised how often opportunities surface when relationships are refreshed.

... Saying, "I was just thinking of you" is a perfectly normal way to start a conversation.

Reach out to someone new. That hiring manager you’re curious about. A LinkedIn acquaintance you admire. A friend of a friend you’ve always wanted to meet. Coffee is a low-pressure way to make the first interaction human.

...Saying, "I'm connecting with leaders in XYZ space, and your profile stood out" is one way to start the chat.

Treat it as an informational interview—without the jargon. Come prepared with curiosity and a handful of thoughtful questions, but let the conversation breathe. The value isn’t in ticking through a list, it’s in building rapport.

Keep it simple. Respect their time. Be genuinely curious. Share your own story clearly, without overselling. And if you can, buy their coffee. The best conversations happen when they know you are gracious for their time and perspective.

Virtual Can Work. Not everyone you'd like to connect with is within a 15 min drive, so it's okay to make it virtual. Of course, it's not the same energy exchange as in-person, but it's still better than not connecting.

At minimum, human connection is good.

So here’s my encouragement for you this week: don’t spend another night scrolling job boards. Don’t wait for another networking event to come along. Instead, invite one person to coffee. One conversation may not change everything, but I'm certain it's worth the effort.

Get caffeinated with your network. See where it leads.