“How do I get across?”  he called out.

I was walking one of the side trails in the woods close to my home in Concord, Massachusetts. A warm December day. The normally frozen ground was soft and the spring-fed creek was a bit wider than usual with water-soaked ground on either side.

There was no obvious way. He was with his family – one of his parents (I’m guessing), a couple of young children,  and a dog, looking to complete the circuit trail around the pond that’s the centerpiece of the Woods, coming from the opposite direction.

From my side of the creek I could see that, short of walking his mother and his children through mud and water up to their boot tops, there was no way.  Stumped, as it were.  My friend and I turned and retraced our steps back the other way.  The family on the opposite side did the same.

That moment and his question, “How do I get across?”, describes a moment many of us reach in networking events when we meet someone new.  We start up some small talk – sports is a good topic this time of year in Boston – and then we get to “that moment” when a transition to more substantive conversation might be useful and we find ourselves wondering, “How do I get across” to the more substantive conversation, and saying, “Well, it was great talking to you,” and moving on in search of more solid, dry ground.

In the woods, we might (with great effort, lacking any tools) have shifted a downed tree or limb to bridge the bog. In conversation, with less effort, we can bridge with a question to learn something more interesting and (we hope) identify something about our conversation partner that might lead to mutual interest in continuing discussion at another time or, at least, recalling our conversation with pleasure the next time we meet.

“What question?”, one might ask, “to use as the bridge?”

Well, it depends. In a networking meet-and-greet, our main objective is to CONNECT with the people standing before us by either genuinely or disingenuously showing interest in them. (We are reminded of George Burns’ point, “When you learn [to fake sincerity], you’ve got it made.”  But, never mind.]

So, to make this conversational bridge, we can either go “with” the flow of conversation or “against” the flow.  Let’s say we’re small-talking about the New England Patriots and their upcoming Super Bowl appearance.

A “with the flow” bridge might sound like, “It sounds like the Patriots are a VERY important part of your life. How did you become so interested in professional football or the Patriots in particular?”  The answer to this question will probably give us some clues about other parts of our conversation partner’s life about which we can ask questions and deepen the conversation.

An “against the flow” bridge might sound something like, “It sounds like the Patriots are a VERY important part of your life. What’s the day job you do to support your professional football habit?”  This clearly signals, “OK, I’m finished with football, what else have you got?”  to our conversation partner.  The bridge is rooted in football and goes another direction.  Again, the answer to this question will probably give us some clues about other parts of our conversation partner’s life about which we can ask questions and deepen the conversation.

Once the conversational question bridge is down and we’re across, we can continue to explore their priorities, their point of view, their take on the world.  Questions like “What do you like about that?” or “How did you decide to do X instead of Y at that point?” or “Why are you doing X instead of Y? “  can be very helpful in elevating the conversation over the deepening mud of small talk so that, at the end of the discussion, we have a solid  foundation for conversation at a later time.