One of the hardest things about running a business is human resources.  Picking the right person for a job can literally mean life or death for a company, especially as you move higher up the food chain.  Some may argue that a CEO is little more than a figurehead and the real heart and brains is the people in the trenches, and while that may very well be the case, no one can argue against the notion that a CEO holds great influence over a company’s trajectory, for better and for worse.  So let’s assume for a moment that the CEO or leader of any organization does hold the lion’s share of influence in determining the fortunes of all stakeholders (customers, employees, shareholders if applicable).  What traits do you want in a leader of a technically focused organization?  I have selected 3 of the most influential men that have worked at Apple Inc. to compare and contrast in this thought experiment.  

I will caveat this post by saying I have never met any of these three gentlemen.  Like most, my knowledge of their personality and leadership traits is limited to what can be gleamed from biographies, films, interviews, presentations, and second-hand accounts from industry insiders, friends, and media.  So perhaps the following is all but a misunderstanding of the reality, so let’s assume for a moment the stereotypical depiction of these three hold relatively true.  Here is my understanding of the three men:

1. Steve Jobs:  Visionary.  Businessman. Obsessive.  Perfectionist. Focused.  Showman.
2. Steve Wozniak:  Technical genius.  Passionate.  Lifelong learner.  Teacher.  Caring.  Honest.  Altruistic.
3. Tim Cook:  Operations. Production. Behind-the-scenes.  Thinker.  Git’er Done Attitude.  Citizen-minded.

As I work on my book about leadership and leadership, I keep coming back to Apple for many examples.  So to help flesh out that thinking I wanted to post this as a sort of rough draft.  It can be argued that these three men have very different personalities and skills, and yet because of common purpose have each contributed uniquely to the success of Apple.  So, that presents a unique question.  Who would you choose to be the CEO of your technology focused company?  Now, of the three only Jobs and Cook have served as CEO.  But let’s assume that Wozniak could have done equally well had he ever had the desire or opportunity.  Tough question.  Now, certainly no two companies are the same and each face unique challenges, but those differences aside, who would you choose?  I think the answer lies by asking yourself two questions:

1. Where is the company currently at in it’s life?
2. Where does it want to go?

I tried to boil down a company’s life to 3 distinct phases. In the beginning you are bootstrapped nobody looking suckle the venture capitalist honey.  Everyone is dreamy eyed and energetic.  16 hours days for weeks at a time are nothing!  Then, if you are lucky, you make it.  Your products or service becomes popular.  You can grow.  Money is no longer as tight, and you have a little more time to follow passions.  Then, inevitably you become the “old” thing.  The thing that is so last year.  Profits start to decline, growth isn’t quite as explosive.  Maybe you downsize a bit.  Sure you’r still doing okay.  But who want just okay?  Who do you want leading the charge in the years?

1. Startup Years:  You always need the Woz/Jobs combo in the beginning.  One to focus internally and get the damned product just to work.  Someone who can corral technical disciplines to march in one direction.  But you also needs the external pitchman.  The guy who can go out sell an idea, raise capital, schmooze.  Either a Jobs or Woz should work great for those early years.
2. The Good Times:  Once everyone loves you, the hardest thing is to get them to keep loving you.  I argue during the good times you need the Woz or the Cook type in charge.  With the Woz type you get someone who isn’t complacent to keep peddling the last year product like so many MBAs would advise.  In tech, only the paranoid survive and you can’t be afraid to cannibalize your own successful products with new risks.  A Woz type will want to keep making your product better.  On the other hand, people also like to get more for less.  A Cook type an help drive down your manufacturing and resourcing operations, drive you to efficiency so that you can drive down costs and increase profit.  Better yet, pass some savings off to customers in cheaper prices so they become repeat customers and add a little more profit to the bottom line.  Win-win!
3. Has Been:  Maybe you’ve IPO’ed.  Maybe you are a market giant.  But also likely there is a new younger, leaner whippersnapper biting at your heels.  You are so veste in supporting your legacy that innovation is hard.  In these times I’d argue that the Jobs or Cook type is necessary.  Jobs can be the magician.  Reminding people why they love your product so much.  They bring excitement back to an existing product line.  Or they can help envision the next big thing.  Of course, for the same reasons listed above, a Cook type may also be a good fit for the plateau years, at least for a while.  But remember in tech only the paranoid survive so don’t rest on those laurels too long.

The reality is any company would be lucky to have any of the three at the helm.  Even more ideally, someone who can emulate the best of all three would be ideal.  So before we wrap this thought up, let’s look at what characteristics, in my humble observer point of view, all three men shared:

1. Committed
2. Competent
3. Clear Communication
4. Forward Thinking
5. Connect The Dots
6. Willing To Be Wrong