I have a confession. I'm a pain in the ass (arse, for my colleagues speaking proper English) to work with. I thrive on impossible challenges and expect those I work with to do the same. Growing up, my dad's constant refrain was "Nothing is impossible. Some things just take longer." So it's no surprise that I see leaders who are similarly pains as role models.
I've been lucky enough to meet many of these like-minded pains, but I never had the chance to meet Steve Jobs. I have, however, had the chance to meet Apple's co-founder Steve Wozniak on several occasions.
Having been an Apple user from pre-Macintosh days, I have to admit that meeting the Woz for the first time was a thrill. During our first meeting, we talked about everything from slide rules (you know, the things NASA used during Apollo 13 to figure out really complex math problems that computers were just too slow at!) to the first Texas Instruments calculators to his thoughts about cybersecurity.
We then meandered through a bit of computer history, talking about the early years at Apple, the excitement of breaking new ground, the beauty of great engineering, and why a well-laid-out motherboard is a piece of artwork.
Eventually, however, our conversation made it over to the topic of the other Steve. At the time, Steve Jobs had just made public that he was dealing with some health issues, the same ones that would eventually take his life.
It wasn't clear how severe Jobs's condition was, but I wanted to be sensitive to the context of what was going on, as well as the complexity of Jobs and Wozniak's relationship and Woz's current role as an outsider. So I tried to tread lightly. But I was incredibly curious about the reputation Jobs had for being intolerant of anything less than peak performance. I had always wondered how Jobs got the most out of his people if his private persona was anywhere near as abrasive as his public one.
"We all like praise, but it is in the challenge we overcome to earn it that we find satisfaction and fulfillment."
Woz was amazingly transparent about pretty much everything I asked. So I finally put it to him bluntly: "Was Jobs really as much of a pain in the ass to work with as many people make him out to be?"
The answer I got reminded me of how my one-time mentor Peter Drucker used to answer my truly ridiculous questions without telling me just how ridiculous they were. He'd say, "Well, Tom, I think that's the wrong question." Woz did something very similar. He answered by sharing a story about Jobs from their early days at Apple.
As Woz told it, Jobs had a habit of sometimes just popping into meetings. He'd quickly survey the room, take stock of the problem being addressed, and without so much as five seconds of prelude announce to the people there, "You can do better than this." And with that, he'd leave the meeting. His comment wasn't necessarily delivered with a tone of arrogance or even disappointment, but rather as a statement of fact--simply put, "Don't settle!"
Big deal, right? I mean, the initial reaction is "What the hell does he know about this problem and how tough it is. After all, we've been at it for days, and this is the best we can do!"
Well, it sort of was a big deal, because when Jobs told you that you could do better, you somehow wanted to figure out how.
As I listened to Woz tell the story, I was transported back to when my kids were much younger and I was coaching them for a creative problem-solving program called Destination Imagination. Destination Imagination was all about challenging kids with tough and intricate problems that they needed to find solutions to on their own, with zero parental or adult involvement. So why have a coach if the coach can't actually help you with the solution? Well, what amazed me was that my principle role ended up being to simply tell them they could do better than whatever limitations they chose to latch on to. It was fascinating, because no matter how well they thought they had done they were almost always able to do significantly better when they were challenged to do better.
Granted, as an adult coaching kids you have an inherent advantage in that they will believe you when you tell them they can do better. However, that is also the primary role of a true leader. In many ways, that's what Jobs was doing. It wasn't lost on him that he had an amazing aura that imbued his actions and words with more meaning than most mere mortals'. Yet, as leaders, we are all called to set the bar for our organizations, our people, and, yes, ourselves.
While it may feel good to tell people they've done well, to laud their efforts and celebrate their wins, it is far more important to first challenge them. We all like praise, but it is in the challenge we overcome to earn it that we find satisfaction and fulfillment.
Don't let that small piece of wisdom slide by. Drucker would constantly remind me that the greatest role of a leader is to challenge people. He felt strongly that this one quality was the core value of all great leaders and managers. Through challenge, we prove to those who chose to follow us that their capabilities are far greater than their expectations of themselves.
Note, at no time did I say that you'd be thought highly of when you are putting forth challenges that seem unreasonable, unrealistic, and downright absurd. You're a leader, a pain in the ass. Deal with it!
Nothing is more powerful, meaningful, or fulfilling than allowing someone to experience the realization that they are stronger, smarter, or simply more resilient than they thought they were.
Any person who gives you the chance to experience that is a person you will follow to the ends of the earth, no matter how much of a pain in the ass they are.