Trillion Dollar Coach summary

Bill’s coaching career was over and, aged 39, he entered the business world. His first job was at the ad agency J. Walter Thompson. He showed the same enthusiasm in his new role as he had on the gridiron, and clients loved him – especially Kodak, who decided to poach Bill from the agency and install him as their head of consumer products in Europe. It was a brilliant start to a late-blooming career.

Things got even better in 1983, when Bill received a call from an old Columbia buddy. John Sculley had just left Pepsi to become the CEO of a tech start-up called Apple. Convinced he was on to the next big thing, John offered Bill a chance to get in on the ground floor. It was a huge move, but Bill accepted.

The first leg of Bill’s journey with Apple came to an end in 1990. In his last years at the company, he headed up a spin-off software venture called Claris. It did well under his stewardship, but Apple ultimately decided against making Claris public. That was Bill’s signal to leave and begin a new chapter in his career. He would spend the next decade at the tablet computer startup GO and software manufacturer Claris, before trying his hand as a business coach.

And his first client? His old employer, Apple. We’ve already seen that it was Bill’s sense of loyalty that brought him back to Columbia as a coach. Well, that quality ran deep. When Steve Jobs was forced out of Apple back in 1985, Bill was one of the only prominent team members to argue that the company couldn’t afford to lose their talented figurehead.

In 2001, when Bill started working with Google, the company was in the middle of a radical experiment. Fed up with top-down interference in creative projects, Google’s co-founder Larry Page had decided to do away with managers altogether.

Larry’s so-called “disorg” model seemed to be working, but Bill thought it wasn’t sustainable. Their argument went back and forth until Bill made a suggestion: Why not ask the folks at the sharp end of the action – Google’s engineers – what they thought?

There’s a common idea that people who show their emotions in the workplace aren’t as competent as their less “touchy-feely” peers. But that’s a fallacy. Few people know that better than the folks who worked with Bill.

Bill was famous for his personal warmth and informality. He gave his colleagues bear hugs, had a breezy – and often downright profane – way of talking, and wouldn’t hesitate to blow a kiss to a colleague on the other side of a meeting room. More importantly, he’d drop everything to help people out if they were in trouble. When Steve Jobs was incapacitated by cancer, for example, Bill visited him in the hospital every day.

In the 1980s, when Bill was first starting his Silicon Valley career, most executives at tech firms were men. One of the few women in a senior position at the time was Deb Biondolillo, Apple’s head of HR in the US.

Bill had noticed that Deb always chose a chair at the back of the room rather than at the conference table at the company’s weekly staff meetings. He asked her what she was doing all the way back there and told her to “get to the table!” One day, Deb finally took the plunge and grabbed a front-row seat. That’s when gruff executive Al Eisenstat sat down and asked her what she was doing there. Deb nervously told him she was waiting for the meeting. He eyed her suspiciously and then turned to Bill, who subtly indicated that he’d made the call. That, she recalls, was the moment she knew things would work out.

In the previous blink, we saw how Bill helped Deb Biondolillo get a place at the table. The reason he could persuade Deb to grab a seat next to an intimidating executive and Al Eisenstat to accept this was simple: they both trusted him.

But what is trust? Well, here’s how an influential 1998 article published in the Academy of Management Review journal defines the concept: trust is all about a willingness to take a chance because you have positive expectations for someone else’s behavior. And that’s often what makes boardrooms tick.