How to bond with your boss

I am sitting outside Starbucks waiting until 10 a.m., when I am to meet the CEO, who is waiting for me inside to talk about who-knows-what before we visit a client. I do not want to be one minute early in case I run out of stuff to talk about. He greets me with a huge smile, an energetic handshake, and a two-shot latte. “I got one for you,” he says. I do not tell him this will force me to get up from the meeting 20 times to pee.

He tells me he redid the entire presentation the night before.

He says, “How was your weekend?” I say, “Fine.” Why would he care what my weekend was like? And if he did care, he definitely would be unhappy to hear about it. I ask him how his weekend was because I am trained in the graces of human conduct. He says his brother got in a car accident.

He tells me about his brother. He tells me his brother is depressed and has not been functioning for years. No one knows what to do. He thinks the medication caused the accident.

I take a sip of my latte. What to say? I say, “It must be really hard on your family.” Yes. This is good. Compassionate yet vague.

CEO: Yeah. Depression is so hard to understand.

Me: I know. I have experience with it. People’s first instinct is to say, “Get up. Go do something.”

CEO: Do you know this from other people or personal experience?

I take another sip. Why is he asking this? Why is he having this conversation with me? I decide he needs a friend, and there is no one else he can talk to. I say, “Both.”

At this, he tells all and more. What drugs his brother takes. Why his brother won’t listen to anyone. He tells me his sister is also depressed. He tells me she used to be a real go-getter who could go for weeks without sleep.

I get the whole picture now. I tell him that actually, I know a lot about this stuff. The drug his brother is taking is usually prescribed for depression, but it sounds as though he and their sister are manic-depressives, and his brother’s reaction to the drug was typical for a manic-depressive. I tell him his brother and sister sound like they are at opposite ends of the same hereditary mental illness.

The CEO is wide-eyed. I am worried that he will think I am insane. I say, “Did you read that article in Fortune about CEOs who suffer from mental illness? I think it’s common.” I say, “I think, actually, that you are manic-depressive too, but you are manic, which is great for running a company.”

He says nothing.

I say, “You are lucky.”

He says, “Maybe not. You never know when you will be hit with something like this — when you wake up one day and can’t get out of bed.”

I am pleased that I used my coffee time with the CEO to bond — which is what all the how-to-be-great-at-work books tell you to do. And I think I made a good impression as being someone who has a well-rounded base of knowledge.