Stop Chasing Strangers: The Warm Ecosystem Strategy That Actually Works

(For small teams, teams of one, and everyone who secretly dreads cold outreach)

Let’s be honest: Cold outreach is awkward, uncomfortable, and often leaves you second-guessing yourself. You wonder, “Are these even the right people? Why am I bothering them? Did I say the wrong thing?”

I’ve been there. Cold outreach might build courage, but it also taught me this: You don’t have to find courage by reaching out to people who don’t know your work.

The Uncomfortable Truth About Cold Outreach

For most nonprofit leaders and fundraisers, cold outreach triggers:

• Fear of being ignored or judged

• Worry about not being “big enough”

• Pressure from leadership to deliver results

And layered on top of all that, the institutional pressure: Your board asks, "Any new corporate leads this month?" Your executive director asks, "So… how is outreach going?" It’s natural to want to meet expectations and deliver results. Recognizing these pressures helps us remember we’re all working toward the same goals.

Cold It makes us visible in uncomfortable ways. For small teams—especially teams of one—it can feel deeply personal.

But here’s the relief: You don’t have to start from scratch. You already have an ecosystem.

You Already Have an Ecosystem (Even If You Think You Don’t)

Many say, “We don’t know wealthy people,” or “Our board is small.” But your network isn’t about money or big companies—it’s about the people who care, even a little, about your mission. These connections are often more valuable than we realize.

The Three Circles of Your Warm Ecosystem

Circle 1: Closest Champions Founders, board members, volunteers, long-time supporters—people who already want you to succeed.

·      Action: Write down ten names. Invite each to a short, curiosity-driven coffee chat (“I’m exploring a corporate partnership idea and would value your perspective.”) No pitches—just listen.

Circle 2: Community Connections Vendors, partners, neighbors, families, recurring donors—those who greet you warmly, even if you don’t know their last name.

·      Action: Reach out for brief conversations. Ask what interests them about your work and what might engage companies like theirs.

Circle 3: Dream Corporate Partners (Describe, Don’t Name) Don’t chase logos. Instead, picture the type of partner you’d love to work with—those aligned with your mission and values.

·      Action: Focus on describing the qualities you seek, not specific company names. This creates real alignment and opens doors authentically.

The Shift: From Chasing to Inviting

You’re not chasing support. You’re inviting people to join something meaningful, offering purpose, community, visibility, and connection. When you see it as an invitation, your conversations become more genuine and rewarding.

How to Activate Your Ecosystem: The Coffee Strategy

Commit to ten coffee meetings—start with Circles 1 and 2. Ask questions like:

• “If you were me, how would you begin engaging companies?”

• “What do you think would excite professionals in our community?”

• “What’s our strongest value to a corporate partner?”

Bring warmth and curiosity to these conversations.

You might say to someone, 'I admire how you engage clients. How could we use some of those ideas in our outreach?' Simple acknowledgments like this help build trust and set the stage for real connection. This is how your network grows over time.

When (and How) to Ask for Help—The Alignment Rule

Don’t:

• Ask for money

• Ask for introductions right away.

Do:

• Ask for perspective

• Ask what would appeal to a corporate audience.

• Ask what they think your strongest assets are

• Say: “Would you be willing to meet with me a few times this year as a sounding board?”

People feel valued and included when you ask for their perspective. Often, introductions and new connections will happen naturally.

What Success Looks Like

After ten coffee meetings:

• You’ll speak about your mission with greater ease

• You’ll gain new insights and honest feedback

• You’ll identify new supporters and advocates

• You may receive warm introductions—no cold calls required

And remember, not every outreach will lead to a yes, and that’s perfectly normal. Progress is about learning and moving forward, not just results. Try to note three takeaways from each meeting to help you improve and keep your momentum going.

10 Coffee Meetings in 30 Days

You have everything you need to start. Commit to ten coffee meetings in the next thirty days. Your plan:

• Ten meetings

• Honest questions

• Focus on alignment, not just names

• Invite people into meaning

• Build your community before your strategy

If you try this and want to compare notes, feel free to reach out — I’d love to hear what surprised you.

You’re not chasing strangers. You’re growing your ecosystem.

You’ve got this.