He did a range of jobs in New York, starting with being Santa. (Santa dos and don'ts number 4: "Drinking hot chocolate with whipped cream while wearing your beard may make a big mess.")
One of his best jobs was in a sandwich bar, building bespoke sandwiches for Manhattan customers in a hurry. He wasn't very good at it because he was slow and lacked dexterity. But he liked pleasing customers and he appreciated the way his co-workers - all much younger - treated him.
"Halfway through my first day, the manager put a hand on my waist and one on my shoulder.
'Would you do me a big favour?' he asked.
'Sure,' I said.
'Would you please not cut everybody's sandwich in half? If they ask you to cut it in half, then do that. But don't offer to cut everybody's sandwich in half. You're slowing the line.'"
It was that sort of plain discourse that Cheever appreciated. "My co-workers weren't always friendly, but they were always present, always direct. There were squabbles but little hypocrisy. I was part of a team. I felt loyal, included."
In education we make great play of the importance of teamwork, but we aren't always good at the direct, straight talking that is surely necessary. If people don't say what they mean, if they hold back for fear of offending, then sooner or later the team will fall apart.
It is probably something to do with the role of the teacher, traditionally someone who encourages and cajoles, helping pupils over obstacles and avoiding direct confrontation. So the anger that is sparked off in a staff meeting gets played out somewhere else - at home, perhaps.
"He's stark raving mad."
"I see. Did you tell him that?"
"Of course not. Do you take me for a fool?"
Someone who understands the importance of honest talk is writer and lecturer Susan Scott, who works with organisations both in the United States and here on what she calls "fierce conversations" - "fierce" meaning direct and passionate rather than angry and confrontational.
Her message is that work, relationships, the whole of life in fact, are driven by a series of conversations.
"What gets talked about in a company, and how it gets talked about, determines what will happen," she writes.
That is so true. I meet a lot of school senior managers who have done excellent things. They tell me about them - how this or that has changed.
And all the time I'm trying to imagine the meetings and the conversations that have taken place along the way - because I know that it was through a long series of such conversations (some awkward, some inspiring, some dismal, some merely timely) that the thread of improvement was woven.
Disaster is the same. It comes gradually through a series of failed or missing conversations until it catches up with itself and there is a sudden dip.
"What we see is the sudden part," Ms Scott explained in a TV interview.
"But of course it happened gradually. What were they pretending not to know?"
What she advocates is clear, unambiguous, honest and uplifting talk. Any single conversation might turn out to be the most important one you have ever had.
"A leader's job is to engineer epiphanies - one conversation at a time,"
she says. "Conversations that reveal we are capable of original thought.
Intelligent, spirited conversations that provide impetus for change.
"And yet often the talk is only of measured results, of economic indicators."
Sincerity is high on Ms Scott's agenda. "We all know people who are looking at us, body towards us, but aren't really here at all," she says.
When Ben Cheever left the sandwich bar, he took away good memories.
"The bread is fabulous. I hope they remember the second gimmick too, though. It is kindness."
Selling Ben Cheever, Bloomsbury, 2001. Susan Scott www.fierceinc.com Gerald Haigh is a former head who writes about education