Hey Jon. Thanks for reading the article & posting a comment. Interesting question.
I haven't and I feel that it could get a bit more akward, if you haven't established some sort of connection first.
Another reason against it might be that if the other person blanks out, you don't know enough about him to fill the void. In the example I've given with Matthew, when he blanked I knew enough about him and his endeavour (writing a book) to come up with a few ideas how he could do research for his book.
On the other hand, asking this upfront sets the tone for the entire meeting. That is also a great benefit.
Yes, I have. A few months ago in a meet up in Europe. I didn't know anyone and I thought that it could be a nice way to break the ice as this is the way I naturally behave, I mean offering to help people out.
What I've got as feedback went from weird looks to passive-aggressive responses. I was as disappointed as I was shocked. Why were these people reacting so rudely to an honest selfless offer?
A few hours later hanging out with totally different people at another pub I've got way better output out of this behavior.
My conclusion was that in this business people are so used to harsh conditions that they aren't even able to acknowledge that something good is being given out of nowhere.
Anyhow just don't. Or, at least do what the OP did, talk to the person around an hour before making the offer. Because anything less than that is a guaranteed way to get weird responses.
I've had people try it on me. It was incredibly awkward. It did come off as arrogant. And the first thing it made me wonder is 'wtf? who are you?'
I don't know if it was tone, timing or something else, but I don't think it should be a cold opener. There needs to be some small talk beforehand, a decent understanding of what someone is doing.
If you and I talked and I just told you what I'm working on and you actually seem engaged, interested and knowledgeable then asking 'Is there something I can do to help you?' might be a natural and genuine statement.
Taking advice/help from someone requires some degree of trust, establish a little before trying this imo.
It's useless to ask "how can I help you" unless they already know how you could help them. They can learn that if you first introduce yourself, tell about your life and your business, etc.
From Christoph's post:
> After about an hour of covering topics ranging from places to see around the area to consulting gigs to building a SaaS application, I asked him one very simple question: "How can I help you?"
The question works because before he made it to his interlocutor, he had already told his history. The interlocutor had enough information about him to know what to answer when he made the question.
