When A Homeless Man Changed My Mind - Radiant

The Radiant Blog

Posted by Andrew VanderPloeg

Cardboard Sign

That image represents one of the traditional ways that people in need ask others for money. But what if there was a better way?


Last week Thursday night, I was in Toronto to support a friend who was playing a gig at Lee's Palace. Lee's is a historic place that has hosted some of the biggest names in music and so the experience was one that a few of us didn't want to miss supporting him in. By the time we all arrived, there were 7 of us gathered from different places (London, Cambridge, Toronto)

After the show, we hung around the area, picked up some pizza and then ended up catching the end of the NBA finals at a nearby establishment, which ran until almost midnight. As we all prepared to go our separate ways, we stood on the street and chatted, saying our goodbyes.

As we were standing there, a homeless man walked up and started talking to one of my friends about his T-shirt. He spoke softly and in the cacophony of a Thursday night in Toronto, you had to lean in to hear him. The conversation developed and they ended up chatting for about 5 minutes. Then he asked me a question and I chatted with him for another 5 minutes. Then he started talking to another one of my friends as well, and in each case, he demonstrated a surprising knowledge of many, many places and topics. For instance, after asking where we were from, he proceeded to explain a number of connections that he had with London. Each of us, therefore, felt a connection to him and had developed a bit of a relationship through the common interest/knowledge/experience.

Now, to this point, he hadn't asked for money and although each of us wondered if it was coming, there were no hints that he was going to ask. To that point, 15 minutes in, all he seemed to want to do, was just talk to some other people. I remember thinking to myself that I actually didn't know if he was going to ask at all. I wondered if perhaps, all he wanted was to talk. As I think about that in retrospect, if I'm honest, that lack of certainty of an imminent request for money caused a lot of my usual guard to drop.

However, a request for money did come. But when it did, it came in context of one of us asking him if he had a place to go that night and how he was managing living in Toronto. In response, he highlighted some of the great places that he can go to get food and shelter. It was at that point, only when WE had brought it up and only after developing a connection with us for 15 minutes, that he finally (and rather sheepishly) asked if we did have any change.

It strikes me more now than it did that night, but as I think about it, that was an absolutely unbelievable example of how to approach any kind of transaction - approach your audience, engage them in things they are interested in, genuinely listen and care about what they say, and then, if the opportunity arises (which it always will if you are patient), you'll have the chance to make your pitch and when you do, the experience will be better for everyone.

How was it better for everyone?

To be honest, I rarely give money directly to homeless people. It's not that I don't want to give, it's more that my giving to them happens through established programs with accountability built into them. But in this case, I broke my usual rule. Through relationship, this gentleman made me want to give something to him - enough for me to forego my usual conviction and giving strategy.

This all led me to the realization that, even if he wouldn't put the term on it, this homeless gentleman had a far firmer grasp on good branding than many, many organizations do and we have a lot to learn from him.