The 3 Hardest Words in Management

What are the 3 words that managers find hardest to say?

They are possibly the 3 words that parents find hardest to say to children.  They are 3 words that teachers very rarely say to their students.

They are not “You’re the Best”. They are not “I love you”.  What might they be?


The 3 hardest words for a manager to say are “I don’t know.”

The need to act under the lack of full information does not give the excuse of not needed to do the work.  One must do the work to examine the data that is available, to seek advice from wise counsel, to speak to others who have experience; but the analysis once done, must end.  A decision must be taken by the leader.

Orchids are not Fragile

I am reading Nassim Taleb’s latest book “AntiFragile” at the moment.  I received 2 gifts of this book for Christmas – I do hope it is not because I am generally seen as “fragile” and in need of some increased strength…

I remember a conversation with my friend Xavi, who runs a gardening business.  We were talking about Orchids.  He explained “there is a widespread idea that Orchids are difficult plants, they are fragile.  This is not true.  Any plant that has survived the millions of years of evolution to survive in its form today is in no way fragile.  It is not suited to certain environments, but it is not fragile.”

Most complex organic systems not only survive uncertainty, chaos, disorder, time… they thrive.  They grow stronger though dealing with their environments.  There are forests that need fire – certain trees can only grow past a certain point if they face fire.  A human muscle will atrophy if not used, it will grow stronger through being worked, through being damaged.

Modern education equates volatility with risk, equates non-standard with failing.  Statisticians hate the outliers.

Nassim’s central idea is that we cannot predict risks, but we can predict a system’s capability to cope with risk.  We cannot predict an earthquake, but we do know whether the 400 year old cathedral or the poorly built modern apartment block will fall first.  We cannot predict a financial crisis, but we can predict which bank will fail first.  We cannot predict loss of employment, but we can see which human will come back strong the fastest.

Leading in the Real World

The real world has surprises.  Hemmingway said that the “true” parts of his stories were the most un-believable.  Fiction is never as crazy as reality.

There are 3 things a good leader must learn to be able to do:

  • Act under Uncertainty
  • Take the Painful Decisions
  • Own the Decision

Acting Under Uncertainty

I teach a class towards the end of the course on the MBA program where my objective is to create uncertainty.  As the students give their answers, I give no expression, neither verbal nor non-verbal as to whether I agree with their answer.  This creates tension in the class.  The students are used to a class where they say their answer and the professor either writes it up on the board or grimaces.  If the professor writes it up, I got the answer right.  If the professor grimaces, I change my answer until I get a nod and a note on the board.

I believe education from “The All-Knowing Professor” creates a dangerous tendency for future leaders.  In the real decisions of life, there is nobody there to nod their head, nor to say “no” or “incorrect”.  There are many people making lots of noise, and the leader needs to commit to their course of action without achieving 100% consensus, or 100% of the information that could prove the course of action.  Leaders must be able to do enough work to be fairly sure they have a good course of action, and then commit to that course of action; and get others to commit.

If MBAs are learning always to wait for someone else to give then certainty, then they are not learning to lead.  We need to ensure that tomorrows leaders are getting practice in the world of uncertainty.  They are getting practice at having to move forward without all the information.

Taking the Painful Decisions

Odysseus must choose between definitely losing a few of his men by passing closer to Scylla, or possibly losing all of his men passing nearer to Charybdis, the whirlpool.  There was no “good” alternative.  MBA cases, video games, TV series tend to allow the hero to find a “good” outcome.  They allow the business to survive with nobody losing their job.  They allow the main character to finish the journey and get back to a comfortable life.  If you have a good option and a bad option, this is not a decision.  It is obvious.  A leadership decision is always between 2 bad options.

Many of school’s choices are between a good and a bad outcome.  Most of life’s choices are between two bad outcomes.

Own the Decision

When I was young, 12 or 13 years old, I was once caddying for my father.  We were at a par 3 and we discussed what club to hit.  I suggested a 7 iron.  He thought it was not enough, but after a pause, took the 7 iron anyway.  He had a look at the green, the flag.  He took a few practice swings. He stood up to the ball.  He swung the club making good contact with the ball.  It soared up and was in line with the pin.  It hung in the air for 2, 3 seconds… and then dropped…  15 meters short, landing in the sandy bunker.

He made a pained grunt and as he returned the club to me I said “sorry, I gave you the wrong club”.  He said, “No, you are the caddy, but I am the golfer. I chose wrong.”  At the time I remember feeling bad.  I felt that I wasn’t “respected” by him, that he didn’t treat my advice as serious advice.  Now I think that he acted then as he has always acted.  He owned the decision.  I gave advice, but at no point did it become my “fault”.  He owns his decisions, whether in golf, in business or in life.

Blainroe golf club 15th hole, where I learnt my golf

Learning to take responsibility for the choice, where it is the leader themselves who must choose, is a challenge.  It takes psychological maturity to own a decision that cannot necessarily be justified with the data.  It takes psychological strength to deal with the slings and blows of others who have not had to take the decision.  Leadership is solitary.  Any education of leaders must help the leader find the mental strength necessary to be alone.

Being alone and being lonely are different.  Alone is a choice.  Lonely is the desire to have someone else to take away the burden.

A good leader has mentors, friends, advisors…  but when the decision comes, it is they and they alone who are responsible.

Increasing your Question to Answer ratio

In an uncertain world, the art of “Muddling Through” is of greater importance than the art of long-term strategic planning.  Dealing with the chaos requires accepting the chaos, and then taking quick steps to understand the map, the compass.  In management life, giving answers shrinks our understanding; asking questions increases our understanding, our capacity to adapt.

How many of your statements are answers and how many are questions?

The person asking the questions is in control of the conversation.  It is hard to remain open to other’s ideas.  It is hard to stop saying what it is that I want to say, and giving the other what it is that they need to hear.

The Best Questions…

  • The best Leadership Question:  “What is the next right thing to do?”
  • The best Teaching Question: “What do you think?  What other options do you see?”
  • The best Coaching Question: “You have achieved what you set out to accomplish.  Imagine yourself there.  What does it feel like?”
  • The best Friendship Question: “How are you?”
  • The best Parenting Question: “What was the best moment of your day?”
  • The best Sales Question: “(I understand that price is important.)  What other criteria are important in making this decision?”  (The implicit question: “What are you comparing this to?”)

These questions come from my blog series The Origin of Leaders over at ActiveGarage.com.

What do you think?

Let me see how many times I can say “I don’t know.  What do you think?” today.

So… in the comments below…  What do you think?

29 responses to “The 3 Hardest Words in Management”

  1. as a leader I believe we have to do few things to take decisions
    1. Widen options. Look beyond your problem, anologies, ask help from people who had experienced similar issues etc.
    2. Always test assumptions. We are driven by confirmation bias. I find this most difficult.
    3. Distance myself from problem. A lot of time egos take control.
    4. Accept that I can be wrong.

    Similar too what you said in your article. I hope new IESE classes are challenging you.

  2. Very good article.
    I will soon have to take an important decision that will have an impact on my career and life. I’m asking myself if I should go to university when I finish my program or if I should start my business. I already have a business plan that got reviewed and approved but I don’t have money. Whether I go to university and my parents pay or whether I start the business with an investment. The university is a good option and starting a business is a risky decision, so I can say bad option. You said it’s obvious to go with the best option. In this case would it be stupid to start the business?

  3. I was moved …. no hit by the statement : Fiction is never as crazy as reality.

    But when I re-read it, well it couldn’t have been said any better.

    This was my first intro to your article ; got ‘led’ to it through twitter … shall share it on LinkedIn.

  4. As usual, so well written. My takeaways-
    1. Anything which has survived so much change, is not fragile. Understanding this changes perspective … the way we look at ourselves, others and things around us.
    2. I liked your point about uncertainty and how B-schools fail to give right perspective.

    At the end, to say “I don’t know” is a double edged sword. There is always a chance of your being perceived as weak/unaware. So, a leader has to be really good at work and have the ability to articulate it in a way that drives forward looking positive discussion.

    1. I agree… the double edged sword… there is a style of saying “I don’t know” but with body language that doesn’t position me as weak and uncertain, but strong and open to understand other perspectives – it is the body language/self belief that is projected that is more important… 😉

  5. […] Neill habla en su magnífico post “The three hardest words in Management” de la necesidad de saber decir “I don’t know” ante preguntas cuya […]

  6. Hello Conor

    I recently came across this model called “Cynefin model” which describes how we choose in complex environments


    Snowden, the creator, explaining it:

    Best regards

    1. thank you for this information – I’ll check it out 😉

  7. Duncan Armitage Avatar
    Duncan Armitage

    Great site Conor. Stumbled here via Facebook….classic avoidance behaviour on my part. Facilitating leadership workshop tomorrow so my surfing benefitted from your insights. Hope all is well and I will be back here. Dunc

    1. Thanks Duncan, plenty of inspiration came from your leadership philosophy 😉

  8. The golf story you shared is interesting. There is a difference between owning the decision as a leader which in the right circumstances is admirable and important and allowing our people to take ownership themselves. There can be a tendency to suffocate others by taking ownership too much and too often. Those around us learn and contribute more when we are able to delegate responsibility, that is why we hire smart people, isn’t it. We increase the output we get from others when we give them room to make decisions then ask questions. Why did you make that decision? What would you do differently next time and Why?

    I like your “Best questions” Thanks for another thought provoking post.

    1. Thank you. 😉

  9. Different managers (and people more generally) have different sets of three words that they find hardest to say and they vary according to the interplay between situation and personality.

    Some managers find it easy to say “I don’t know” when asked questions by team members because they don’t care enough to find answers or can’t be bothered to make the effort to say the words or think of an answer even if they know enough to do so. There are other managers who, as you point out, have to be seen to be all knowing at all times just as there are managers who struggle to say “Am I wrong?”, “I need help” , “Thanks for that”, “Life comes first” or “That is cool!”

    There are those who cannot say “I feel awful” and others who do nothing but complain. There are many who say “Will this work?” but some who cannot say “Why not try?”. Your blog post, for me, is even more useful when we consider what three words, or so, we tend to use a lot and then consider whether we ever use the opposite, and whether we should start.

    We can all become caricatures of ourselves over time, particularly if we are shielded from change by our hierarchical role and culture. Reversing some of our ‘bingo’ phrases will relieve colleagues of the tedium of having to say “Not that again” ever time we open our mouths and help us to avoid insanity by “Doing something different” and treating each day as though it’s “always the beginning”…

  10. Was reading your suggestions to being more of a leader to your audiences , i think thats how i am in a sense ,just havent paid that much attention but with the daily decissions i have i will look closer @ what im doing. I no iam a leader but need more positive influence with my surroundings.

  11. Hi Connor, thanks for your post. I think it is great. I do agree with you, specially in the “own the decisions” part.

    What makes me sad is that I do not know if the people who must choose a person to lead a company, a department or a project team, would choose a person like the one you describe, a leader. In my experience, I’ve seen Human Resources managers choosing the one that has always an answer, who speaks in very technical slang that not everybody understands but seems very “professional”, the one who masters the action of blaming others… Only when things become really tough or wrong they choose the leader you have described, if they have the chance.

    Don’t you have the same experience? In the same way that schools love to teach problems that have answers, I think managers and HR managers love to hire people who always have an answer not people that ask questions.

    Thanks again.

  12. Great article. I could not agree more that our educational model needs to reach a better balance between knowledge and personal abilities. Teaching how to team work, to communicate effectively and to take decisions and accept consequences would be necessary if we want future directives to be leaders too.

    1. Yep, the world is getting ever more volatile and connected… education is preparing us for standard days… but life will have fewer and fewer “standard” days in future. We need to be preparing ourselves, and our next generations, for dealing with change, dealing with “wow, I never thought that would happen” days 😉

  13. Miguel Irisarri Avatar
    Miguel Irisarri

    Surprinsingly, too many managers unable to say “I don’t know” reach the top position of a company. I wonder if the shareholders are aware about what could be the value of their companies with better leaders.

    1. Yep. John Wayne remains a leadership role model for many 😉

  14. I don’t know

    1. You nailed it 😉

  15. Wrestling between the typical default path of “giving answer to question, receive feedback” and the desire to engage in a more revealing cycle of “ask reply question that acknowledges I understand question while at the same time pulling the questioner further toward revealing what he really wants to know is a challenging goal that I want to explore more. Have you found this successful or frustrating in more personal conversations with those familiar with you?

    1. In Entrepreneurs Organisation forum meetings we speak about responses being Non-Gestalt, Gestalt 1 or Gestalt 2.

      Non-gestalt is advice. “You should sack him” being an example of non-gestalt listening – I am imposing my own criteria on your situation.

      Gestalt 1 is sharing a relevant experience from a similar context. “2 years ago I had a great employee who didn’t get along with the rest of her team…”

      Gestalt 2 is sharing something that connects on the emotional level, but may at first seem to have nothing to do with the initial problem being shared. “My parents moved house when I was 14 and it had a big impact on how I related to my circle of friends…”

      The deepest listening is to the emotion behind, and to the reason this problem is important in the context of the life of the person. The shallow listening is to figure out what advice to throw out to them.

      The challenge of any “tactic” for listening, is that the tactic itself is not the purpose. Passing a medical exam doesn’t prove I could be a doctor, it proves I can pass a medical exam. The “recipe for listening” approach can’t work without an understanding of the deeper purpose. However, I think we need to learn the two in tandem – a tactic to have another tool when faced with a challenge that seems obvious to me, but has my friend totally blocked.

      1. I remember several years back, during my time in middle school, being more quiet than the average, but not by design. Other students it seemed always had the right thing to say at the right time while I struggled to become engaged in the rapid fire dialogue of school yard talk. Alas, it was just not my style. I am the person that needs more time to think before I can respond. My brain just does work fast enough to banter easily.

        Your blog post, for me, requires several rereads, looking for verbs and following the train of thought, not unlike many I presume. I will go against the advice of Abraham Lincoln, “Better to remain silent and be thought a fool than to speak out and remove all doubt”, by agreeing with you that a tandem approach seems the concise well spoken path, notwithstanding the devil is in the details. If you were to describe the tandem approach as a street intersection, what would you call the street names?

      2. While reading my posted post I noticed my use of the quote seemed to imply a risk of foolishness to agree with your comment. That is not what I wanted to say, it came out all wrong. Please excuse my efforts. I was trying too hard to give my answer to your question. I have much to learn. I better go reread the blog again and take the advice of Abe closer to heart.

      3. 😉 blog is exactly that, a place I write stuff I am thinking about, that is 60% sound, often flawed. The comments and debate help me think deeper. If I “know” the answer, better to write a book or a journal article 😉 thx for keeping me improving

  16. I like very much the comparison you make bw/ real life decisions and the Scylla and Charybdis choice. It is easier both teaching and understanding reality through a manichean perspective, but it is just this, a way our mitochondria feel more relaxed. Life, as every human being older than 30 knows, is a complex polyhedron you will never understand in depth, so better take the risk, keep on moving, and learn!

    1. Hehe, and how to accelerate this idea of how complex life is before we hit 30? and some people hit 50, 70 or never… I do think that schools love to teach problems that have answers.

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