Embrace the awkward in conversations

This week, I read a great Twitter thread by the previous CEO of Segment, an analytics software company. He described being against hiring a salesperson he didn't think would be an excellent cultural fit with the engineering managers he'd have to persuade.

But, alas, he was proven dead wrong over the years. Surdi, the sales manager, did a stellar job and exceeded his expectations. The key to his success? He cut to the chase and asked customers questions that made them feel awkward and uncomfortable but yielded treasure troves of insights for the company.

Where other salespeople got customers used to being talked at about a product, Segment took the opposite, dialectic approach. The safe, "tell me what you think about the product," questions were replaced by the earnest, "Why did you have us here today?" or "Why don't you just build Segment yourself?". Bolstered by success, the question got even bolder: "Who's the ultimate economic decision maker on this? You?". Frankly, they were right to do so, especially with companies with labyrinthine sets of stakeholders and politics that would waste their time.

Cut to the chase. Most meetings suck: they're unclear about their purpose and go on for too long because everyone is usually too afraid to be the one to cancel. Even researchers think they're a form of therapy for cogs who don't understand their purpose in the machine and need to reassert it or reassure themselves that their work still matters. And small talk sucks, too, in all relationships. But we stretch out chats about the weather, travel, education, commutes, and the price of things when we could establish a real connection with someone. Life is short. The clock is ticking. Other people's patience is not infinite.

Replace small talk with big talk.Why are we so incapable of it? Why not ask about what matters right from the start? Why talk about commutes and weather when you can talk about dreams, beliefs, hopes, and fears? It shouldn't be hard to ditch the habit, but it is. What's the worst that can happen? At best, you'll have a great experience and deepen your relationship with someone. At worst, some funny story to tell later. Embrace the awkward: questions or silence even.