The American entrepreneur and self-confessed underdog revealed he had severely questioned his competency while serving as CEO for Pure Software – going so far as to ask the board to sack him, twice.
Hastings admitted he felt “under water a lot of the time,” and felt like a failure because he was particularly bad at hiring – he’d had to re-hire a new VP of sales every year for five consecutive years.
“I just couldn’t pick,” he said. “I kept picking the wrong type of person because I just didn’t know that much.”
While Pure Software sales doubled every year for six years, Hasting’s confidence continued to nosedive; “The real thing is that I felt like a failure because I was clearly making these [sic] big wrong decisions,” he said.
In front of the board
Pushed to breaking point, Hastings approached the board and asked them to dismiss him.
“Twice they said that ‘Yeah, you really are making the big mistakes, but we would still rather have you do those mistakes than do the other set of risks.’ It gave me absolution or resolution because they were kind of my confessors and then I could forgive myself.”
Onwards and upwards
“One of the hardest things is when you make big mistakes as a leader is to be able to forgive yourself, because for the sake of the enterprise you just feel terrible,” Hastings said in the interview, which was part of a Kleiner Perkins workshop.
“And yet you have to realise that, hey, if you gave it your cleanest, most ethical and hardest thinking shot, then that is all you can hold yourself accountable for. Not the outcome. But that’s hard,” he continued.
While Hastings’ hiring skills once leaved something to be desired, he insists they’ve since improved. So what’s changed?
“I do a lot of references and am basically of the view that people can buffalo you for four or six hours, so don’t pay too much attention to the interview,” he explained. “The interview is like a narrowing round. Then you really go deep on the blind references.”
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