Self-Confidence – in – Chief

I was watching a television show the other night about a young man who wanted to be a standup comedian. He got on stage and did his routine (as bad as it was) but soon realized that he lacked the self-confidence to be a comedian.

I realized that for any job: comedian, doctor, or chief, a certain level of self-confidence is required to be successful.

Great leaders have a strong presence and bearing. They are unflappable people that never let you see them sweat. Everything from how they carry themselves to how they speak and dress ooze self-confidence.

How does a chief become self-confident?

  1. Learn you are not perfect. There are never right or wrong answers to complex business decisions. The best that you can do as a leader is to gather all of the information you can, do a cost-benefit analysis of potential options, use your best judgment-and then make a decision.
  2. Commit. (I learned this on the golf course.) Commit and go for it. Don’t second-guess yourself. Believe in what you are doing and with positive expectations toward the achievement of your vision.
  3. Failure is always a possibility. You are going to make mistakes. Learn from them and move on–don’t dwell on them.
  4. Put on a brave front even though you are scared on the inside. Everyone can be afraid at times. If you are a leader, your direct reports will read this. If you show a lack of courage, you will begin to damage your employees’ self-confidence.
  5. Find happiness and contentment in your work. Do the best you can. Follow your heart. When you win, celebrate. When you lose, just start over the next day.

The Near Perfect CEO

Have you ever wondered what qualities make for a “perfect” CEO? Here are two lists that describe the qualities that make for a near perfect CEO.

22 Traits of a Perfect CEO

  1. Secure in Self
  2. In control of attitude
  3. Tenacious
  4. Constantly Improving
  5. Honest and Ethical
  6. Thinking before talking
  7. Original
  8. Publicly modest
  9. Aware of style
  10. Gutsy/a little wild
  11. Humorous
  12. A tad theatrical
  13. Detail oriented
  14. Good at their job and willing to lead
  15. Fighters for their people
  16. Willing to admit mistakes, yet are unapologetic
  17. Straightforward
  18. Nice
  19. Inquisitive
  20. Competitive
  21. Flexible
  22. Good storytellers

How To Think Like a CEO by D.A. Benton

In addition, Robert Beauchemin ( wrote a great piece on the “Personal Characteristics of a Great CEO”. In this article, Robert does a great job of describing 14 uncommon personal characteristics for a CEO.

  1. Stamina
  2. Educated
  3. Visioning
  4. Listening
  5. An eye for talent
  6. Passion
  7. Discipline
  8. Communications
  9. Follow through
  10. Technical, Selling and Leadership
  11. Controlled Emotions
  12. Adaptability
  13. Level 5 Leadership
  14. Ethics


Corporate politics is the bane of many executives. It is everywhere in a company. There is no escaping from it. Because of the level the CIO reaches in an organization it is a fact that he/she will be dealing with political issues daily. So if you cannot run from it, it is best to play with in it and win.

Most executives are horrible at politics. Most think they are good at but in truth they are not. It is not their fault. There really is no school to go and learn how to deal with politics. You learn how to deal with politics from the street.

Politics in general has a bad reputation, however, there is also a good side. The good of politics is figuring out how to shape your agenda so it fits in a way that is positive for everyone affected.

A CIO that regurgitates tech jargon and buzz words will not get ahead in the game of politics. Politics is about selling. People make decisions emotionally and use their intellect to rationalize these emotional decisions. If you want to accomplish anything you will need to sell to the decision-makers. That means understanding the decision-makers background and thought process. Like governmental politics it means figuring out who will be on your side, who will fight for you, and who can be persuaded and how.

Now the dark side of politics can be more vicious. Let’s face reality; it is also the most interesting. Backstabbing happens to all of us at some time in our careers. It is the nature of the beast. All you can do is figure who the person is and how they are trying to do it, and plan your moves to counter them. It is a game of chess.

To win, you must always remember that corporate politics is a game with high stakes. Never forget that being a CIO means being a politician first and foremost.

Further reading about corporate politics:

Corporate Politics-The Elephant in the Room by Mark Beckford

Winning At Organizational Politics Without Losing Your Soul by Dan King


For those of you who are history buffs, Ronin was the term used to describe a samurai with no lord or master. There was essentially no leader for them to follow.

Recently, the chairperson of the board I sit on resigned. He is moving on to bigger and better things in the local political party. I wish him all the best on his future endeavors. The problem is he was one of those charismatic leaders that got things done. His leadership unified the board. His absence now leaves a vacuum that might be difficult to fill with someone of equal quality. The board is now in limbo about its direction.

So what happens when an executive (CEO, COO, President, or CIO) resigns? Obviously, there will be anxiety and feelings of betrayal and uncertainty from everyone. This is normal and human nature. Remaining executives should take the time to talk to their staff and each other. It is best to have open discussions even when you do not have all the answers.

Remember this is a time of change and change can bring both opportunities and threats. How you take advantage of the opportunities and mitigate threats will decide if your firm will be successful or not during this transition.

According to the Bushido Code, a samurai with no leader  was supposed to commit oibara seppuka upon the loss of his master. I am glad times have changed…

Modesty and Humility – Leadership Style

For those of you that read my blog regularly, you know that I am constantly analyzing what traits make a good leader so others and I can incorporate these traits into our management style.

I discussed this topic in “6 Ingredients of Leadership”. Leaders should have vision, passion, integrity, trust, curiosity, and daring to be effective leaders. While reevaluating this post I came up with other traits that I think are important to effective leaders. These traits might seem trivial but if you look at truly effective leaders these traits round them out and make them more effective leaders.

Modesty – Modesty means the quality or state of being unassuming or moderate in the estimation of one’s abilities. Good leaders need to have modesty in abundance. A modest leader should accept criticism and understand his/her limits. On the outside a modest leader might seem quiet and reserved, but to those who come to know them, they are intense workers who are obsessed about getting results. A modest leader should not have an ego. Modesty helps a leader make good choices while maintaining a leveled head.

Humility – Humility is defined as modesty or lacking pretence, not believing that you are superior to others. Humility is a trait that is often overlooked in leaders. It is often looked at as a weakness when, in fact, it can be a tremendous asset to being an effective leader. A leader that is humble rarely allows the power of his/her position to cloud their judgment. If you recognize you are not perfect it creates an environment where those around you feel comfortable making mistakes and taking chances. You look for the opportunity to learn something new and use every opportunity to make others feel valued. The act of being humble assumes you do not have all the answers.  A humble leader knows that change is constant and they can keep up and grateful for the opportunity to learn something new and reinforce knowledge they already possess.

Being and effective leader means accepting your strengths and weaknesses. The more we know about ourselves the better we can be as leaders.

Intimate Leadership-Leadership Advice from Star Trek

Star Trek 2-Wrath of KhanRecently, HBO has been repeating Star Trek: The Wrath of Khan. I am not sure why they repeat this particular movie over and over again but I try to watch pieces of it whenever it is on. Yes I am Trekkie at heart. I have been since I started watching reruns of Star Trek with my father in the 70s.

When you watch something this many times you begin to pick out details and maybe over analyze it too much. For those of you who are not familiar with the plot: the crew of the Enterprise reunites; battles Khan Noonien Singh with casualties; and wins to save the universe. You get the idea. What is interesting about this plot is this is the one that Spock sacrifices himself for captain, ship, and crew and ultimately dies in the end.

I started to think about Leader (Kirk) and follower (Spock) relationships. Why would anyone sacrifice himself or herself? The relationship between Kirk and Spock go beyond captain and first officer. Their relationship is a particularly close interpersonal relationship. Both Spock and Kirk know and trust one another very well and are confidants of one another.

Being an intimate leader means your relationships with your followers goes beyond a typical superficial relationship. You form a closeness and bond with your followers and they with you. You trust them and they trust you. This is the ultimate relationship. You are willing to sacrifice all things, including your life, for each other. How many of us can truly say we are willing to sacrifice for our staff? Or are our staff willing to sacrifice for us? Granted, we probably would not sacrifice our life. Do you have that kind or relationship? Do you want that kind of relationship?

The relationship between leader (manager) and follower (staff) is important in that a strong bond allows you to accomplish any task and overcome any obstacle. The relationship between Kirk and Spock allowed them to boldly go where no man has gone before.

Transactional Leadership vs. Transformational Leadership

“Effective leadership is putting first things first. Effective management is discipline, carrying it out.” – Stephen Covey

Are you a transactional leader or a transformational leader?

A transactional leader is focused more on completing a series of goals or “transactions”. Power is given to the leader to evaluate, correct and train followers when productivity is not up to the desired level and reward effectiveness when expected outcome is reached. Transactional leaders have short-term views and are focused on the present.

A transformational leader creates value and positive change in their followers. A transformational leader focuses on “transforming” others to help each other, to look out for each other, to be encouraging and harmonious, and to look out for the organization as a whole. In this leadership, the leader enhances the motivation, morale and performance of the group. Transformational leaders have long-term views and are focused on the future.

Any executive: CEO, CFO, or CIO needs to strike a balance between transactional and transformational leadership qualities. Creating forward movement in any company requires a mixture of both. There is no magic ratio. To be a successful leader one needs to find the right balance that works for him/her.

Qualities of a Boss

“The best executive is the one who has sense enough to pick good men to do what he wants done, and self-restraint to keep from meddling with them while they do it.” -Theodore Roosevelt

My CEO was a great chief executive officer, manager, and leader. I couldn’t ask for anyone better to lead a company or to report to. I started to think about the qualities that made him who he is–his leadership style. What is that “stuff” that made me stay with him for so long? I came up with three qualities: competence, trust, and loyalty.

Competence – My CEO was able to lead the organization successfully. Competence commands respect. While you can have the tile of CEO, can you lead as a CEO? Incompetent leaders have followers that do not respect them, which leads to a weak organization. Competence is developed over time and from different situations. It is a product of life and formed from the circumstances you encounter. My CEO led other financial firms prior to joining our company. He was also ex-military and a veteran. From those experiences he gained the competence to lead.

Trust – If competence is the foundation then trust is the house. Competence leads to trust. My CEO tried to form a relationship with his department heads. We were not just cogs in the machine, but to him we were vital to the operations of the business. There was mutual trust – he trusted us and we trusted him. He had high standards and communicated those standards to us and we knew why they were high.

Loyalty – How often can you say you are loyal to someone? There is your spouse, your parents, maybe even your best friend. But can you say the same for your boss? Loyalty is built over time and from events. I knew my CEO for over 11 years. We went through good times and bad. He took care of me until the very end. Even now that I am no longer with the firm I am still loyal to him.

Competence, trust, loyalty, are characteristics to being a good leader. My CEO gave me motivation, direction, and purpose. As I move into other positions my goal is to further develop and hone these characteristics myself to be a better manager, leader, and chief information officer.

The Clique: As CIO Are You Part of It?

One of the items that can make a CIO a success is the ability to be a part of the leadership team. Every firm has its own defined leadership team. As CIO you should be part of this team.

Within the leadership team there is yet another clique. The people in this club are the real power. They are the decision makers and power brokers. As CIO you might be part of the leadership team but not part of this clique. As CIO it is important to be a member of this clique-if nothing else but to successfully carry out your agenda.

The point of the clique is access-access to information, gossip, and politics. For example, I often had lunch with my CEO and COO-a privileged not given out to many. Not a formal scheduled lunch but more ad-hoc; a quick bite at the local diner. Therefore, it was a special honor to have lunch with them and engage in conversation. When I say conversation, I am not talking about the usually pleasantries about last night’s ball game, but conversations only heard by a few. The inner sanctum if you wish. This level of relationship is formed over time once trust, respect, and loyalty are built (loyalty being key). You should not expect to have these conversations immediately.

Becoming part of this clique is vital because most of a company’s operations are conducted outside of documented processes. Yes, I said it. If this comes as a shock then you are truly an outsider. Yes, there are processes in place but once you have these informal pre-conversations then pre-approval is granted. So the documented process is just a matter of dotting your ‘I’s and crossing your ‘T’s. This is important to further your agenda. I have seen IT executives at all levels fail to have these pre-conversations with the key power brokers – leading to problems and even failure.

If the CEO or COO searches you out to talk about non-business issues then chances are you are in a good position. Don’t abuse this position. As quickly as it comes it can also be quickly taken away.

As CIO you must be an executive officer-a leader, not only in title (those five letters in chief hold meaning and prominence), but also in how you carry yourself and act. The position of Chief Information Officer is an executive one. While you could say you are part of the team are you really part of the clique?