The Fancy Style Of A CEO


No it’s not about socks.

The most important element of a CEO’s style of clothing are hats. We need to wear so many hats and change them so often that it’s a wonder that most of us don’t suffer from bipolar disorder (or don’t we…)

The variety of situations we face on a daily basis demands us to act from a different perspective (or putting a different hat on). Sometimes we need to wear/ manage more than one hat at the same time.

As in life, some hats will suit us better than others. It is important to be aware which ones we feel most comfortable with and which ones fit awkward on our heads. Knowing that a hat does not appeal to you doesn’t mean never wearing it. On the contrary, learning when to put this hat on and wear it with style may bring a major improvement in your performance as a CEO.

Here’s a list of 17 hats that I use on a regular basis. Try them on:

  1. A secretary on asteroids – Sometimes there are just too many little tasks which require your attention. They are manageable, kind of routine, but they need to be done (e.g. emails; phone calls; getting through a couple of contracts). Every couple of days I set an hour or two for those and enter “the secretary on asteroids” mode. (A secretary on asteroids = being efficient in completing a big number of small tasks)
  2. The general – Let’s be straight here. There are cases when you need to put away all “inclusive leadership” concepts and take the captain seat. Times which require taking tough decisions and executing them (e.g. layoffs; closing projects; etc.). It’s the authoritative hat.  These are the times when your actions are not met with cheerful laughter and  may even paralyze your team. But after all a CEO’s job is to lead the organization in the right direction, not to be the most loved person in the room. (The general – making tough decisions and executing them)
  3.  Fat Tony – This and the following characters are “borrowed” from Nassim Taleb’s “The Black Swan” (they are introduced in the beginning of chapter nine). Fat Tony is the street smart guy. He is the type that would much rather ask for apology then ask for permission. As a CEO of a small company I too need to “push the limits of the rules” from time to time. (Fat Tony = being street smart)
  4. Dr. John – He is the learnt type. He can deep-dive into large amounts of data, can read graphs, can draw conclusions based on numbers. He builds models, relies on textbook wisdom and statistical models. No matter how sterile it may seem, when it comes to budgeting, organizational structure, yearly planning… etc., this hat comes handy. (Dr. John = being analytical)
  5. Michael Jordan – MJ is often referred to as the greatest basketball player of all times. Most times when there is a critical situation Jordan would take the lead, making the last critical shot of the game. He’s remembered for many successful finishes which won great sport battles and even championships. Though, if you dive into his playing history a little bit deeper, you would find that he also took a lot of unsuccessful last shots causing his team to lose those games. As a CEO you won’t be making the right decision every time. But when a critical situation arises and everyone else is afraid/unstable/hesitating, you need to take responsibility and make your shot. (Michael Jordan = responsibility in critical situations)
  6. Onassis – Aristotle Onassis is mainly known for two things: 1. being rich and 2. marrying John F. Kennedy’s widow. A thing that is less known is that he was a connector. He was the type of social animal whose charm would open doors and break the ice with almost anybody. He spent a lot of his time socializing and he was a great master of this art. Every CEO should have a connector hat in his wardrobe.  (Onassis – being able to communicate and connect with all kinds of people)
  7. De Bonno – Very often we have to get our organizations out of a mess or face quite an unorthodox situation. This is the time to put the De Bonno hat on. Eduard De Bonno is one of the most renowned creativity thinkers and he has consulted a number of Fortune 500 companies how to resolve complex issues using creativity approaches (By the way, one of De Bonno’s most famous concepts is “six thinking hats”). (De Bonno = creative approaches)
  8. The celebrity – As CEOs most of the time we are quite into demand. All kinds of people and tasks require our attention. At some point you need to shift your paradigm and realize that you cannot be there for anyone who asks for your time (or else you are acting away from your own priorities). There are times when we need to put the celebrity hat on, meaning being unreachable. Just like celebrities, you cannot answer every email, request, question which is heading towards you. (The celebrity – being out of reach for the people and tasks which are outside your priorities)
  9. Martin Luther King Jr. – The art of presenting ideas in a way that engages people is crucial for our profession. It’s not that you can’t be a successful CEO without infecting people with (your) ideas. But the ability to inspire will take your game to a whole new level. So make sure you put this hat on when presenting new projects, when announcing yearly results, on All-hands meetings, etc. Do not wear it all the time as the effect will wear off. (Martin Luther King Jr. = the inspiring leader)
  10. The consultant – The hat of an outsider helps you judge a certain situation in the organization much more clearly. Put it on and you will get a different perspective. Imagine that it is not you but a friend that faces the case and you need to advise him/her. (The consultant – the outsider)
  11. Nostradamus – As a CEO you need to look into the future regularly. Put this hat to see what lays ahead, what will happen in the next year (or ten), where you want to take the organization to. (Nostradamus – the visionary)
  12. The Godfather – No, it’s not about not paying taxes 🙂 The thing that has most impressed me in this character is his ability to stay clear-headed in critical situations. We need to do so too. And it’s not as easy as in a movie. (The godfather – staying cool in critical situations)
  13. The housekeeper – A housekeeper is a person who keeps things in order. As a CEO you need to do that, too. The only difference is that you do not use a broom but processes, organizational structure, project plans etc. The housekeeper cleans and then it gets messy; the housekeeper cleans again and then it gets messy again. It’s a cycle. The natural tendency of processes, organizational structure and project plans is also to get messy. That’s why you need to put the housekeeper’s hat on, on a regular basis.
  14.  15. 16. 17.  And last, but not least – The servant (serving your people); the psychologist (trying to understand); the seller (the persuasive hat); the ant (working hard) are the four hats we should never take off

The art of being a CEO is being able to match an occasion with the hat it requires. E.g., putting a hat of a general when you need to wear the one of a psychologist (or a hat of a secretary on asteroids when you need to wear the one of a visionary, and I’ve done that) won’t bring results no matter how comfortable the hat is. But hesitating for too long which hat to put on is worse.

Here’s a simple exercise for you to do after finishing this article. It takes up to 5 minutes and will enhance the value you get from this article manyfold:

Write a list of all the hats and put a number (0 to 5) next to each hat – 1 meaning “I feel very uncomfortable wearing this hat”; 5 meaning “with this hat on I am on my best”; 0 meaning “I’ve never tried this hat on”.

The fives are your strengths as a CEO. Chances are, they define your management style. Keep your focus on them!

What do you do with lower numbers? Your task is to bring each hat to a level of “comfortability” of at least 3. It’s not part of the five-minute assignment. In fact for some hats it will take years or decades, different approaches and tons of effort from your side. Right now, being aware of the 5s and 1s is your goal!

About me: Apart from acting as a CEO of DEV.BG (the biggest IT community in Bulgaria) I help CEOs of small companies build their business. If you face a case I can help you with, drop me a message on LinkedIN.

Excuse my English 🙂 English is not my mother tongue and as you have seen it may be improved. Though, I believe that my level of command of the language covers the basic criteria in order for me to convey my ideas.


  1. Nice post, I enjoyed it! It sounds so hard to choose the right hat for the right time. I wish there was a magic mirror to show how they fit you. I think they would look awkward on me, they are all men’s hats, apart from the ant maybe 😛 .

    Looking forward to the next post!

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