The Origin of Grit: On Understanding a CEO’s Past

I truly believe that the success of an organization is deeply tied to the people leading it. The best way for me to trust in a company’s future is to try and anticipate how its leaders will react when things go off script. Because things never go according to plan. Not fully. Not for long.

What you need are people who can adapt, create, rebuild, and still inspire others to move forward no matter what. That kind of mindset, that kind of resilience, doesn’t show up in just anyone. It’s rare. It takes a very specific mix of personality and toughness that you don’t often find in so-called “normal” people.

So I asked myself: is there something these exceptional leaders all have in common?

And the more I studied their stories, the more I realized how much of it traces back to their past. Because who you are is shaped by what you’ve lived. And when it comes to how someone deals with pressure, I don’t believe people truly change. We just become more of what we already are.

I- What their past tells me about them

This is something I have never really heard when assessing CEOs: understanding their past. But to me, it is crucial. When I look for information about a leader, I always try to understand where he’s from. A rich family? A meritocracy star? Or a rebel that was sent into the sidelines very early on?

Which kind of traumas he had during his childhood? What kind of things bothered him or obsessed her when she was younger?

Because it is not a myth that our childhood shapes us. We often repeat the same patterns as we experienced early on and even when you did the work and spent thousands of dollars at the shrink, you can never erase what most impacted you. Very often it was witnessing an injustice done to yourself or someone else that you couldn’t fix. An event or a situation that shocked you so strongly that it was written in your flesh. And then, you spend the rest of your life keeping this bitter taste in your mouth like eating an old chewing gum you can’t spit. Something so deeply ingrained in you that it just eats you alive or becomes your life mission.

That is why I am looking at CEOs pasts.

Why? Because then, I know that if I can find the root of his hunger in something painful that she transformed into light rather than rotting inside, nothing can stop her from accomplishing his vision.

It is especially true for founders and smaller companies. The grit must come from something greater than just success, money, glory or power per se.

Suffering is a pain that has no meaning

It is surprisingly often that we see that great leaders have this one thing in common: a high tolerance to pain and a drive that they can’t explain. Sometimes, they don’t really know why they’re doing what they’re doing but they know they can’t stop. We can all agree that trauma or negative events per se is not “good” – it’s the adaptation and recovery process that yields growth. In essence, some individuals manage to not just bounce back (resilience) but to bounce higher, developing greater wisdom or purpose than before. For example, trauma survivors might discover a renewed sense of meaning or mission, a drive to help others or to live life more fully, that they directly attribute to overcoming their darkest moments. It’s important to note that PTG (post traumatic growth) doesn’t negate pain; rather, it means growing from pain.

Being a leader is, by their own admission, a painful experience. And more than anything, it’s a lonely one.

So they need to make sense of it—otherwise, they can’t endure it for long. Whether they’re trying to prove something to themselves or to someone else, most of them end up attaching meaning to what they do. Often, that meaning points to some positive outcome in the future. But the root of their drive? It almost always lies in their personal history.

Trauma as a compensatory motivation

Trauma can instil a powerful drive to achieve, sometimes as a form of compensatory motivation. Psychotherapists who work with high achievers observe that many are fuelled by a “burning desire to compensate” for early wounds or insecurities. In other words, the individual strives to prove their worth, escape their past, or fill an emotional void through accomplishments. The trauma becomes a driver for extraordinary effort. For instance, someone who grew up in poverty might develop an urgent ambition to attain financial security and status.

Ego restoration is another framing. If childhood pain wounded one’s self-esteem, success and recognition may unconsciously serve as healing balm. As one analyst noted, these individuals often believe they succeeded “because of, rather than despite, misfortune,” using hardship as motivational fuel. However, this drive can be double-edged – while it pushes them to excel, it may leave underlying issues unresolved (leading some successful people to still struggle privately with trust or anxiety). This is why we see sometimes some discrepancies between professional and personal success.

A negative event alone doesn’t make someone a great leader. More often than not, what sets them apart is an extraordinary sense of optimism. A deep belief that things can improve, that they can make them better. Maybe that’s the real key to finding someone who can build a successful organization. Hardship only reinforces it. It sharpens their resolve to push further, to excel in the one thing they’re truly good at.

Unapologetically themselves

“In the process of developing their identity, individuals may seek congruence between their input and perceived output into the environment through a continuous, self-adjusting feedback loop. People experience stress when they receive feedback that is incongruent with their self-perceived identity”. Burke, 1991 

That’s something I’ve consistently seen in great leaders: they’ve been unapologetically themselves, often from a very young age. As weird, intense, or offbeat as they were, they didn’t try, or maybe just couldn’t manage, to fit into society’s norms. Most of the time, they know exactly who they are, and they have no intention of softening the edges just to make others more comfortable. It’s more of a “you stay or you go” kind of culture.

Nassir Ghaemi, a professor of psychiatry and pharmacology at Tufts, put it well: ‘normal’ people tend to conform, to compromise, to play it safe. But it takes an original mind, restless energy, and a taste for risk to lead anything meaningful.

Leaders are agents of change. Their actions ripple outward, they shape others more than they’re shaped in return.

And yet, what fascinates me most, is that even when it’s painful, people often stay around them. We’ll explore that magnetic, sometimes irrational loyalty in the next piece, focused on “The Present.”

The case of family businesses

Family businesses are a bit different in the sense that they might not have been founded by the current leaders. In this case, the story is a bit different because you cannot directly link the culture of the organisation to the leader in place. But most of the time, they know very well the history and the roots of the company. You can quickly assess if they are here as a duty, to honour what have been built, to continue sharing and growing the values of the organization or if they have more shallow motives, or even if they don’t really know why they’re here. 

II- How to assess a CEO’s past?

Treasure hunt

How can we uncover what’s the true drive of that person that we don’t know, that we might not be able to meet right away and that is most of the time quite secret?

Well, drill down the internet is one thing. Through normal and deep web search thanks to OSINT tools. Read EVERY single piece, interview, video or information about him. At least, have a broad understanding of who he is, where he comes from and draw hypotheses. It happens that I invest or investigate companies just for their founders.

Just ask and listen

If you can meet him, in person, it becomes quite easy then. Just forget about yourself and open up to what he tells you, not only with the words (most of the time it’s polished), but with his body, the way he talks, where he places his hands, is he comfortable?, who is surrounding him? What does the room look like? What does he dress? Is he trained for communication? If yes, find a way to crack him open slowly, and filter the true personality from the polished one. If not, gather as many verbal and non verbal insights you can. Never, ever draw conclusions before the end of the meeting, he will sense that you judge him (positively or negatively) and it will mess up the interview. Don’t take notes, just listen. It makes it more confidential, and he will feel more comfortable sharing if he knows there is no trace of it.

It does not have to be blunt or too personal. It has to be gradual. Obviously, if you ask about their childhood traumas, they will simply shut down and end the meeting. But start with something related to his past experiences, listen, smile, create a safe space to share. And most of the time, they will share more than you asked.

When you ask atypical questions, they go outside of their comfort zone and get closer to the truth than just the typical investor recital.

Note: what I share here is also true for interviewing fund managers. They are also humans assessed for their long-term performance after all.

Here is an example of questions I can ask to gather information on their past:

• What made you so successful until today?
• What are the experiences that shaped you?
• Can you go deeper on that experience? (one that you find relevant and sometimes one that is at the beginning of his career so you can directly go to the old past)
• What did you study in school? Is it a good memory? Does it help for what you do today?
• Were you ever passionate about that topic (school major or atypical interest you might have spotted during the conversation) before?
• How did you end up in this industry?

For each question you ask, focus on the outcome, the small details that come out. Because if you use these details that he gave in his answer, ask questions about it in return, he will unlikely refuse to answer since he is the one who pointed it out in the first place.

Just follow your curiosity.

Always keep in mind the ultimate reason why you are here: understanding the root of his grit. 

No information?

And when I don’t have any information on him or her, I just put the case on the waitlist until I get more info. It happened for Grenke a few years ago. I prefer passing on a case if I can’t investigate who she is. Because it is such an important part of the organization. If you don’t know who is the captain, it becomes challenging to join the boat for an transatlantic. And even many do invest without knowing, because they just “assume” the captain is well trained and capable, I prefer not taking the risk.

Keep your emotions under control

The hardest thing in this is to separate the “I like him” part from the “He is the right one to lead this organization”. It’s not because the CEO is a jerk that she is necessarily bad for the organization. For some businesses it may count but for others not, depending on the nature of the organization, the culture, the kind of employees you have (engineers dominated or non educated people for example), the industry, and the maturity of the company. I always tend to prefer founder led businesses because I believe they built it around themselves, they built something that is tailor made from and for them. I don’t think anyone creates something that is misaligned with what he likes or believe in in terms of culture, management, structure, etc. A founder builds a culture that reflects its values.   

But that will be for later!