The Most Difficult CEO Skill

Jansen Ko
8 min readMay 31, 2019

Fight Club

Recently I find myself struggling to keep my mind in check. Before I got into business, I’ve set a rule for myself: Don’t do anything that doesn’t allow me to sleep well at night.

For some nights now, I’ve been tossing and turning for hours before I doze off into a restless slumber. After 3 hours I’m roused from my sleep. The mind is racing. There are so many things that I’m responsible for and have yet to do. It’s 5am and I’m wide awake. I force my eyes shut and try to go back to sleep, but to no avail. Guess what. This sounds like the definition of not sleeping well at night. It looks like I’ve flouted my own rules.

In popular media, reporters gravitate towards the glitz and the glamour of entrepreneurship. They write about businessmen at the height of their success. From their vantage point high up in the clouds, it’s all rosy and life’s good. These people are held up as shining examples for everyone else to follow.

But I have the nagging feeling that the truth is far from that. What about the people who try and fail? What about the people who are stuck, unable to move backward or forwards, unable to solve intractable problems stacked one on top of another? What about the people who are forced to choose between worse and worst? What about the mental torture that they are put through, day in and day out?

I owe a duty to my family. I am supposed to be a custodian of family wealth. That wealth is hard fought and hard won. Instead, am I destroying it? I owe a duty to my shareholders. I convinced them to embark on this venture. Instead, did I bring them down a one-way street to failure? I owe a duty to my early employees. These people placed their trust in me, joining me when the place was merely a hole in the wall. Instead of leading them well, am I leading them off a cliff?

I know now that there is a hidden fight club of management. The first rule of CEO psychological meltdown is don’t talk about the psychological meltdown.

I’m just a little girl lost in the moment
I’m so scared but I don’t show it
I can’t figure it out, it’s bringing me down
I know I’ve got to let it go and just enjoy the show
Just enjoy the show

- The Show, Lenka

If I’m Doing a Good Job, Why do I Feel So Bad?

Nobody becomes a start-up founder unless they have a strong sense of mission. Financial gain is not what’s most important to the best entrepreneurs. They want to change the world. Money is a secondary objective. It is the means to an end, not an end unto itself. They are willing to trade a big salary, security and 99.99% of their time because they can’t imagine doing anything else.

I must be accomplished and smart enough that people will want to work for me. Yet, I cannot come across as being condescending or talking down to people. I must put on a different persona with each profile of people I meet with, lest my straight-talking approach offend the sensibilities of people not ready for radical candour or thoughtful disagreement.

A start-up founder can be accomplished and smart, and charismatic enough to attract people to work for them. But they might not make a good CEO. The truth is that everybody learns to be a CEO by being a CEO. I’ve never been a CEO before. On a daily basis, I face a broad set of things that I don’t know or require skills I don’t have. Everybody expects me to know them, because I’m the CEO. I’m supposed to have deep domain knowledge across the spectrum of operations, human resource, marketing, sales, finance, and more. I have never performed any of these roles on a professional level before. How am I supposed to pick up these skills while running a business? It’s like trying to ride a broken bicycle and fix it at the same time.

I’ve received comments that I’m not a good mentor. I struggled with that for a long period. Personally, I don’t believe that I’ve ever had a mentor. I’m a self-starter and most of what I know is through observation, asking the right people, reading, reflection and trial and error. I’ve always thought that good mentorship is about pointing the right direction, giving resources, clearing paths of obstacles, then getting the hell out of the way and letting them work their magic. I’ve learned that this approach only works for a person with high intrinsic motivation and a good appetite for hard work. It’ll be foolhardy to make that assumption of everyone.

That comment really hurt. But I’ve accepted that I cannot be a good mentor in things that I don’t have knowledge of. I’m also responsible for setting the direction of the organization and managing on multiple fronts. I do not have time to hand hold and spoon feed. I do not have the magic pill for intrinsic motivation.

If I’m Doing a Good Job, Why Aren’t I Getting the Results?

A friend was facing some difficulties in running his business and asked me for a chat. Normally I’ll decline such invitations, mainly because I’m inexperienced and probably struggling as much as him. I also put caveats up front that my knowledge is only applicable to a limited domain, and that he should adapt it for the context of his own business.

So we had a 2-hour long conversation, where he asked and I shared. At the end of it, he seemed suitably convinced. I guessed he got all the answers he wanted, except one. He asked me, “Hey you sound like you know your stuff and is quite competent. But why aren’t you getting the results?” That line reverberated like a crack of thunder across my mind.

Well.. I guess the harsh truth is that I don’t know that much, and I’m not that good. Despite my best efforts, things might not end up the way I want. And this is the precursor to another business truth.

Even in the best-case scenario that I know what I’m doing, things can still go wrong. The market is a dynamic place. New competitors are constantly arriving on the scene. Existing players are not going to sit back and let you take market share from them. They won’t go down without a fight. And yes, that means all the dirty tricks you can think of — price wars, staff poaching, outright copying. You name it. It will get ugly. Consumers’ tastes and preferences are constantly changing, as is the state of the economy and their propensity to pay for what essentially is a want and not a need.

When the complexity grows, something is bound to go wrong. At a certain level, your company will do things that are so bad that you never imagined that you’ll be associated with that kind of incompetence. Seeing people waste money, fritter away each other’s time and do sub-par work can make you feel bad. As the CEO, it might well make you sick. To rub salt in the wound, it’s my fault.

Nobody to Blame

I’ve joked that every single problem in the company is my fault. It would be funny if it wasn’t so true. The fittings are falling apart? It’s my fault because I didn’t choose more cost-effective ones when we fit out the place. The sign-up process is manual and cumbersome? It’s my fault because I didn’t design and manage the process well enough. The staff are leaving? It’s my fault because I didn’t push the business fast enough to give them the growth they want. The customer is not buying the product? It’s my fault because I didn’t communicate our value proposition well enough.

Unlike some hired gun who can come in and place the blame on his predecessor, I’ve got no one to blame because I’m the founding CEO.

Every problem in the company is indeed my fault. Being responsible for everything and getting shitty results weigh on your consciousness.

It’s a Lonely Job

When the going gets tough, discussing fundamental questions about viability with employees can have obvious negative consequences. Employees rightly care about their own self-interests and will work for you so long the interests are aligned. They may not have mental capacity to understand the many moving parts that keep the ship afloat. They may not have the mental maturity to talk about the hard thing about hard things. I can understand that; I was an employee once upon a time. If I screw this up, I could well go back to being an employee.

Discussing it with the shareholders or board of directors might also be fruitless because they are too far removed from the problem. They simply do not have the contextual knowledge to make the best decisions. It will take a good amount of time and a lot of effort to get them up to speed, but even so they may not understand the nuances completely. They might be tied down with other obligations and lack bandwidth to contribute in a manner that is meaningful for the business.

You’re all alone. But it’s okay. You’re alone, but not lonely. You stand on the shoulders of all the titans who come before you. There is always a way out.

The Point of No Return

Eventually they’re gonna know who’s right
To make a stand you got to win the fight
Can’t stand the heat then just stay out the light
For you might never make it out alive
You gotta live without the columbines
Let everybody hear your battle cry

Yeah we’re gonna be legends
Gonna get their attention
What we’re doing here ain’t just scary
It’s about to be legendary
Yeah we’re gonna be legends
Gonna teach ’em all a lesson
Got this feeling that we’re so sweet caring
It’s about to be legendary

- Legendary, Welshly Arms

In 49 BC during the era of the Roman Republic, Julius Cesar conquered a vast expanse of territory and won honour for his countrymen. Over the previous decade his men had witnessed the honing of his skills as a military commander and political strategist. Alarmed by his growing power, the Senate ordered him to disband his army and return to Rome. To keep his army and remain in Gaul meant forfeiting his power to his enemies in Rome. Crossing the Rubicon River into Italy would be a declaration of war. It must have been a very difficult decision. He led his men across the river and declared iacta alea est. The die is cast. He became one of the greatest of Roman Emperors .

In 1519 AD, during the Spanish conquest of Mexico, upon landing on the shores, the Spanish commander Hernan Cortes gave the order to burn all the ships. It would have “made sense” for him to retain a ship or two as an escape option. But he knew that the only way to keep himself or his men from quitting is to take the option of retreat off the table. His men would have to conquer or die. History tells us that his men fought ferociously and overpowered the natives, who vastly outnumbered them many times over.

To know when to cross the Rubicon and burn the ships — that’s the most difficult CEO skill.

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Jansen Ko

Writes about random muses. Writes to sharpen clarity of thought.