Keith Watanabe * NET 2.0

The article from CIO.com naturally makes one reflect the other question that underpins the title: If we can recognize a bad candidate, then how can we recognize a good one?

To be perfectly honest, I've worked in few companies that had CIOs.  I have worked in companies that had CTOs and I do think the domains cross over.  Perhaps, we need to explore general characteristics of what may describe a "technological leader."

• Appreciates and understands technology.  I'm a firm believer that executives in these positions who meet this requirement tend to have followers with similar beliefs.  I'm not talking about getting yes-men, but those who are attracted by a person's smarts to want to work with these people.
• Has been in the trenches.  To work up to this level of executive, I think a person should spend significant time getting their ass handed to them in working with technology.  This does not mean hooking your monitor up to your desktop or turning your laptop on.  This is significant work dealing hands on with the daily rigors of the difficulties of technology.  They should have at one point been a system administrator, a developer, a QA person, a DBA, etc. so that they appreciate people working on issues at critical times.  Its hard for your staff to respect you if you lack knowledge.
• Business domain knowledge.  Knowing technology is critical, but also understanding how to apply technology to the business domain you're in charge of is equally pertinent.  One chief role of a technology executive, as I see it, is to be able to communicate to other executives the decisions made in the technology department.  For instance, I might understand web technologies very well, but I would have limited ability to go into a securities company and attempt to apply the same knowledge.  It's just not that simple.
• Ability to take ownership and responsibility during a crisis.  This seems obvious but one of the keys in the article about bad CIOs is that the bad ones are quick to blame and even quicker to run during a crisis.  Taking ownership means getting in the trenches with your team, trying to understand the core problems and giving your team the breathing room to fix situations.  Or accepting blame for failure without trying to point the finger.  Technology can be frustrating to deal with, but those who can keep their cool to me demonstrate that they understand how technology works and can explain failures.
  
• Having a broad field of knowledge of technology.  One CIO/Managing Director at a previous company was excellent in that he could talk about any range of topics in technology.  He didn't have to know exactly how each technology worked, but he knew enough to communicate with those reporting to him.  When you're given a position of responsibility like this, you should be able to cover a broad range of issues, especially if there's no person acting as your second (i.e. where a company has both CTO and CIO positions filled).
• Be willing to upgrade your knowledge constantly on technology.  If you want bragging rights of having the cutting edge technology, you better be on the cutting edge with the rest of the industry.  I think a good CTO/CIO still has some geekiness to himself/herself so that they constantly are examining the latest technologies and trying to differentiate between fads and real winners.
• Excellent people skills.  Being good with technology is just one aspect of being a technologist.  If you're isolated and doing a research project for yourself, you probably don't have to deal with anyone.  However, when you get to this level, you really need to be able to handle all types of personalities.  Again, this is a leadership position so aspects like communication, patience, understanding, all come into play here.
• Having a vision.  My previous CIO would take us into a room and explain his "vision."  The "vision" ended up being a kindergarten mat stuck on the wall with little circles plotting towards the finish line.  I considered this a horrible insult to my intelligence.  More than that, what was on the wall honestly was wrought by everyone else rather than him.  That's not a vision.  A vision is how you want to mold your department and the technology inside.  Great leaders create trends so others follow.  That's why they're leaders.
• Knowing how to prioritize.  I saw the opposite line in the article, but this is important.  Part of telling where your technologists should go is about prioritization.  That includes budgeting, allocation of people, deciding whether to outsource or not and when, etc.  Also, it means knowing when to schedule your projects.  This is all tactics.  You don't want to fire an empty gun at an incoming attacker.  Interestingly enough, the other day my boss wanted me to make changes to the system.  He asked me how long it would take.  There were two changes, one easy, one hard.  Then there was this research project.  The easy one was a low hanging fruit.  But the hard change would interpret my research project.  So I posed the question, "Which one should go first?
• A history of successes.  If a person is to be groomed into this position, he/she should have significant amount of successes that lead towards being promoted into such a position.  A person being hired into the position from the outside should have numerous success stories on his/her resume and these should be validated by the company.  Hiring a CTO/CIO is not the same as hiring a jr level developer.  Just because someone had the title of CTO/CIO in the past does not necessarily imply that they were successful at it.  Companies should carefully perform due diligence against such people who come through the side doors.
• Ability to build confidence quickly with the staff.  Leaders should never portray themselves as the new version of Adolf Hitler, unless they're a real military dictator.  But we're talking companies here, not war.  The thing is that I've found that executives easily have the ability to intimidate and that's the last thing you want to do with your staff.  In IT, people are extremely sensitive and the market is wide open for the most talented people.  So even if you're not the most tech savvy of CIOs/CTOs, the least you can do is cater to your talented people to help you out as you develop as a CIO/CTO in your organization.
• Be willing to protect your staff.  You are the hand that feeds but the mouths that are feeding also often times feed you.  Business people tend to pushy and lack understanding of what a techie does.  But as a techie yourself, you understand that a bug takes significant time to work on or that people require a good deal of time to launch a piece of software.  Business people don't understand these things and it's up to you to make them realize it by taking a stand against them.  One of my previous CTOs was a really nice guy, but the business people (especially the Vulture Capitalists) often times pushed him around.  He managed to protect the IT staff as much as possible, but he still was shoved around and eventually the company collapsed.  Likewise, a previous CIO would suck up to the business side and cater to them too much and then come down on the IT staff during failures.   You can't have these situations as a leader.  You need to take charge and show them that geeks have feelings and are critical components to the organization, not just some door mat.  Again, even if you lack understanding of technology, the best thing you can do is serve for your staff because they'll bolster you when you're weak.

Well, that's my thoughts.  I'm certain there's hundreds of other characteristics in becoming the idealistic CTO/CIO.  But I'll give you a little secret: if I were to become CTO/CIO, these are the things I'd do.