What's It Like To Work For Tim Cook? A Former Apple Sales Exec Dishes

Apple CEO Tim Cook booted out two top executives last week, and some observers were surpised to see that Cook, who seems like a soft-spoken, amiable Southerner, can also play rough. "Cook has shown a ruthless side," Charles Arthur of the Guardian wrote. 

One person who wasn't surprised by Cook's toughness was David Sobotta, a former Apple sales executive who just published The Pomme Company, a memoir of his 20 years (1984-2004) at Apple. Sobotta didn't report directly to Cook, but as director of Apple's federal sales group he had a lot of contact with Apple's current CEO, who joined Apple in 1998 to run operations and, later, was executive vice president of worldwide sales.

Since 2005 Sobotta has written an Apple-centric blog called Applepeels. Last fall he wrote to Cook informing him that he also intended to write a book about Apple. Sobotta quickly received a letter from Apple's legal department, one that left him "extremely upset" and ready to abandon the project, he says.

If you're a hard-core Apple fan it's a good read, if only to get a little taste of what life is like inside Apple. (In a word: Tough.)

Sobotta insists that he has no ax to grind even though he remembers Cook humiliating Sobotta's team at a sales conference by putting up a slide with a picture of a toilet plunger as commentary on the group's performance.

I emailed Sobotta and asked what he thought about Cook getting rid of Scott Forstall, who ran iOS development, and John Brownell, who Cook had hired to run retail less than a year ago. Via email, Sobotta shared the following:

Not A People Person

"Well, for starters, Cook is not a people person," Sobotta writes. "He certainly will not stand behind someone if the going gets rough. He is not that kind of guy. I sense no personal loyalty in him, and I suspect employees already understand that.

"Tim will react to the numbers or his fear of being wrong quickly. Fear of being wrong is a managerial trait that runs strong and deep in Apple because of the way Steve ran the company. Even the appearance of being wrong when in the end you might be right is dreaded at Apple.

"You don't make mistakes at Apple and get a second chance. That often hinders decision-making and creates a lot of passive-aggressiveness between teams that should be cooperating." 

A Poor Judge Of Character

"I haven't followed the saga of the new retail guy so he might have been a terrible hire, but that would also fit the Cook pattern. The people I saw him hire were not good ones. I don't think he relates well to people. Based on some of the people he has stuck with, I think he is poor judge of character. 

"Apple never had a disciplined way of making decisions. It was always whoever got Steve's ear that won. Certain people always had the inside track. Likely the way to win now at Apple is to blow in Tim's ear."

Tim On Tech

"Technology-wise, I think Tim Cook is a lightweight. I never felt passion for technology from Tim like I did from Steve and some of the great engineers."

A Manager, Not A Leader

"I would expect that Tim is having a hard time herding the chickens. From what I saw of him, he was something of a loner. He is not a warm guy nor is he the type to go wandering the halls or Caffe Mac to find out what is happening. His preference is to tinker with spreadsheets and numbers. He is not a natural leader. He's a manager.

"From what I saw, Tim is the kind of guy who would just fire some folks rather than try to sort out what is working and what isn't working. I never felt like he wanted to get down into the details unless they were numbers. I also think he can easily be swayed by someone who protects him from the messy parts of running a company."

The Painful Part

"I use Mountain Lion and Windows 7 both every day.  Windows works better. It pains me to say that. I would rate Apple's screwing around with the 'Save As' command [Apple removed 'Save As' from OS X Lion but restored it, sort of, in Mountain Lion] as one of the dumbest user-interface decisions in the history of computing. I'm not sure pulling DVD drives out of iMacs is much better.  Certainly the maps decision [in iOS 6] will haunt Apple for a long time.

"It is going to get worse at Apple. It is not a sustainable business culture."

Apres Steve, Le Deluge?

"There are three factors that I see, the first being the business culture within the company. While the company needs strong leadership after Steve Jobs, anyone at Apple will tell you that taking risks and showing leadership (rocking the boat, trying something new) are not encouraged. With an environment like that, strong leaders end up butting their heads against the wall, and either leave on their on accord or get asked to leave. The company has a strong 'manage up' culture so it is not unusual for Apple managers to not really have a clue what is happening in their customer base.

"Second, Apple doesn't develop its own talent. The company has a strong propensity to hire folks from outside the company. The new folks come in, spend a year figuring which end is up, and end being very frustrated. [The experience is] demoralizing to the people who now report to them and who already knew what their bosses just spent a year learning. It is a horrendous way to run a company."

What's The Next Great Thing?

"The third is that Apple is a `next great thing' company, and that in and of itself is unsustainable. They haven't found the next great thing after the iPad and iPhone, and their shares in both those areas are slipping. Of course they are ignoring traditional computers to a large extent.

"I could add a fourth [factor] related to the third point, but it's debatable. Always in the past when Apple screwed up or got too cocky, they could fall back on a core group of `prosumers' who were dedicated to Apple's products. I think Apple has lost or is in the process of losing those folks, but I have no way to measure that other than I know a fair number of folks like myself that are no longer Apple products evangelists.

"I got a note from [a former Apple colleague] last night that it was time to replace his wife's MacBook and he offered to get her whatever she wanted. She chose Lenovo."

David Sobotta's book, The Pomme Company, is available in Kindle format from Amazon. Don't hold your breath waiting for an Apple iBooks version.

Top image courtesy of Reuters.