The Power of Coffee Dates

Want to know my number one secret to growing—both in my business and as a leader?

It’s not marketing or perfecting my sales pitch. It’s not a coaching program or professional development.

It’s coffee.

Specifically, getting coffee with a wide range of people, consistently over time.

In the age of digital marketing, endless Zoom calls, and ever-transforming technologies, it can be easy to overlook the simple act of asking someone to coffee. But we are still hardwired for connection—one-on-one conversations with people who are doing interesting things and willing to offer insights and connections we didn’t even know we needed.

I came upon this well-kept secret of success almost by accident.

Back in November of 2015, I was reckoning with the fact that I no longer wanted to be an elementary teacher. Between constant curriculum changes, adopting one-to-one technology, toxic leadership, and a mountain of unrealistic expectations, I felt frazzled—like a first-year teacher five years in a row. But I couldn’t wrap my mind around leaving the career I had gone to school for. If I wasn’t an elementary teacher, what would I even do?

Luckily, I had the rest of the school year to figure that question out. I set a simple goal: reach out to at least one person a week who was doing something I found interesting or intriguing, and ask if I could buy them a cup of coffee and ask about their life setup.

I talked to someone from my church who wrote for a magazine. She connected me with a couple who had just returned from housesitting on an alpaca farm in New Zealand.

A colleague connected me to a former teacher who had started his own marketing agency. And my roommate introduced me to a woman who would later become both my mentor and a client.

With each conversation, my world expanded and my mindset shifted. I went from “What the heck am I going to do?” to “Which option do I want to choose first?” And when I started dreaming about freelance writing while traveling solo, I had an incredible resource to tap into—a network of people who were cheering me on, eager to make introductions, and excited to stay in touch.

When I settled in Northern California a year later, I used the same model of asking new connections for coffee. It was the single most effective way I grew my business to consistently reach six figures within a few years.

Over lavender lattes and peppermint tea, I met colleagues who became close friends, leads who became my biggest referrals, and even my first employee. People began reaching out to me for coffee—asking for advice, insight, or a window into the world of marketing.

Overcome the Excuses

I can hear what some of you might be thinking: That’s all well and good for you, Allie—but networking isn’t for me. I’m too introverted, too shy, too busy, or unsure of where to start.

I get it. Networking can feel hard. I’ve had plenty of moments pumping myself up in the parking lot, or feeling nerves similar to a first date. Who am I to ask this person to take time out of their busy day? What will we talk about? What if it gets awkward? Shouldn’t I be doing something more productive than going to coffee?

And yet—I’m always glad I did. I always walk away with new insights, fresh ideas, meaningful connections, or tangible leads. It always feels like time well spent.

As Porter Braswell shared in a Fast Company article:“Today’s leaders need more than strategy decks. As we face political uncertainty, technological advancements, and cultural shifts, no leader can afford to try to go it alone… Leaders should prioritize building connections just as intentionally as they do other aspects of their work. The future of business will be determined by those who connect and collaborate, and those who have built the trust required to make an emergency call at an odd hour.”

Just over a year ago, my family moved to the Midwest, and once again, I was at square one when it came to a business network. But instead of feeling overwhelmed, I knew exactly what to do. I started attending networking events, business card in hand, and following up by asking people to coffee.

This year, my goal is at least 50 coffee dates. Here are the strategies I keep top of mind as I reach out:

• Be good at first impressions. After networking events, I try to be brave and signal that I’m open to connection. I lean on Vanessa Van Edwards’ advice: open body language, warm eye contact, and thoughtful questions. (Think “Working on anything exciting lately?” instead of “So, what do you do?”)

• Be bold and curious. Even if it’s the speaker at an event or someone who seems intimidatingly cool, I don’t let comparison or my inner critic get in the way. People are often far more open to connecting than we expect. A follow-up email or LinkedIn message that’s direct, warm, and curious goes a long way.

• Use tech to simplify the process. I dislike the back-and-forth of scheduling emails, so tools like Calendly help remove friction and make saying yes easier for everyone.

• Be curious and offer value. Most people love talking about what they care about. Genuine curiosity builds trust. Following up—sending an article, checking in on a project, or making a thoughtful connection—amplifies the impact tenfold.

• Leverage their connections. Toward the end of a conversation, I often ask, “Who do you think I should connect with?” People are incredibly generous with their networks. I try to reciprocate by making introductions in real time when possible.

This isn’t just about growing a business or expanding social capital.

In a time marked by uncertainty, division, and rapid change, choosing to slow down and engage in one-on-one connection is a powerful leadership practice. It builds trust. It creates resilience. It reminds us that behind every role, title, or LinkedIn profile is a human being navigating their own questions and challenges.

A coffee date isn’t “just a cup of coffee.” 

It’s an investment in relationship, in community, and in the kind of grounded, human leadership these times are asking of us.

And that? That’s a quiet act of transformation.