I recently scheduled a dinner for design-build thought leaders here in Richmond and invited a group of designers, architects, and builders to spend an evening together. My hope was to begin building a stronger sense of community and foster peer learning. Some of the invitees I knew well, so connecting with them was relatively straightforward. A quick email or text was enough. The people I didn’t know, though, proved to be a very different challenge. I sent out direct emails, but reaching out cold in 2025 is nothing like it used to be. Gone are the days when you could simply pick up the phone and make contact. Most of us (including me) now block calls from unknown numbers, and with the latest iOS updates, the same is true for text messages. Unless a sender is already in your contacts, their messages often never surface.
These obstacles made me stop and think about what cold calling really means today. If we are going to cold call or text, it needs to come from a place of permission. In other words, you must offer something of real value in exchange for someone’s time. In this case, my dinner checked that box, and I felt good about the invitation. But because the concept itself is unfamiliar, the natural response for many people is to put their shields up and delete or ignore. So how do we break through the clutter? I decided to lean into five methods to redefine cold outreach and build trust while educating potential prospects:
| Method | Use Case | Priority |
| Warm Email | Thoughtful intro with a clear call to action | High |
| Personal Text | Short, casual, and value-driven ask | High |
| DM (LinkedIn/Instagram) | Soft entry with shared context or mutual connections | Medium |
| Warm Call | Scheduled conversation with known context | Medium-Low |
| Cold Call | Last resort or follow-up after no reply | Low |
From my experience, social engagement layered on top of in-person connection gives you the permission you need to ask or reach out cold. Without that groundwork, people’s defenses go up immediately. Another cardinal sin (which I committed) is to reach out to someone asking them for something (even to attend a free dinner) without having a fact pattern of what Jesse Itzler calls the “three C’s” (Connect, Console, and Congratulate). This is a long-game process of dollar cost averaging communications over time, building trust and gaining permission for asks like my design-build dinner.
Also by Henry Clifford: Empowering Employees to Make It Right
At the end of the day, cold outreach isn’t really about the ask at all. It’s about what Gary Vaynerchuk calls “jab, jab, jab, right hook.” In other words, give, give, and give some more before you ever ask for anything in return. When we consistently show up with value, whether it’s an introduction, sharing an article, or simply praising someone’s work, we earn the right to make an ask later.
This has been a humbling exercise. I realized that even though I know many people within our industry, I have not been as personally active in the design-build community in my own backyard. I clearly have some work ahead, but this process has been a valuable lesson in building a new cadence of outreach and engagement.
Also by Henry Clifford: Dodging Dysfunction
How are you redefining cold outreach in your business?
Stay frosty, and see you in the field.
