Why Executives Leave

Henry Ward
7 min readFeb 17, 2023


I wrote this three years ago to help my employees understand why executives leave Carta. I’m sharing now in the hopes it will help CEOs, executives, and employees better understand executive departures.

How to think about executive departures
In January and February I did a few office visits where people asked me about recent executive departures. I realized that many of the questions were because I haven’t given employees context on how I make these decisions, what I expect of executives, and how executives are different from most employees. Since then I’ve been thinking a lot about executive departures and the reaction from employees. Specifically I’ve been thinking about two questions:

  1. When an executive leaves, why do employees think the company is in trouble or I have trouble keeping execs?
  2. Why am I surprised employees think that?

My answer is that employees and ceos have different, perhaps even orthogonal, lenses when evaluating executives. If beauty is in the eye of the beholder, so is executive performance.

There is no A for effort
Most employees are given credit for trying hard. If a new onboarding manager isn’t able to get a customer live when they were supposed to, we give them a lot of credit for doing their best, working hard, and doing everything they could to succeed. Even if they don’t succeed we keep encouraging them to work hard and get better.

On the other end of the spectrum is me. I get zero credit for effort. Nobody cares how hard I work. Customers don’t care, investors don’t care, employees don’t care, the market and the world doesn’t care. Nor should they. If I don’t make payroll, don’t raise money, don’t grow the business, don’t build new products, it doesn’t matter that I tried really hard to. And that is how it should be.

Executives are more like me than a new onboarding manager. But it can be easy to forget that. Employees, particularly those working directly for an executive, will feel it is cruel and unfair if I depart a beleaguered executive that is working hard but struggling to be successful. They think it is unfair because it would be unfair if it happened to them. And they are right. But executives don’t get credit for effort. Only results. Steve Jobs describes this shift from effort to results based evaluation as a person’s career matures. I think it is a fundamental lesson in thinking about careers.

As a career unfolds and you get closer to the ceo, the evaluation of an employee moves from effort to results. A Director might get some points for effort but more for results. A VP might get slightly less points for effort but still can earn a few. But at some point if flips completely to results. At Carta today, that is when you become an executive. You don’t have to be an executive to act this way. But you have to act this way to be an executive.

A great boss does not equal a great executive
Most executives are good bosses. Employees like, and often love, working for them. They would not have become an executive if that were not true. Just as a person moves up in their career, results matter more and effort matters less, being a good manager matters less and being a strategic asset to the ceo matters more. Let me be clear. It isn’t that being a good manager doesn’t matter. It becomes a given. I expect executives to be good managers just like I expect them to work hard.

Most employees evaluate their manager on how good a boss they are. As they should. But I don’t. Nor should I. Just like I shouldn’t evaluate them on how hard they work. It is a given. And similarly the board doesn’t evaluate me on whether I’m a good manager. It is a given in order to get the results I need from the company.

Instead I evaluate executives on their strategic value to the organization. That is difficult for most employees to evaluate because they have limited visibility across the organization. They can see things in their department very well. But it is harder to look across departments. That’s why employees feel betrayed when an executive leaves. They think “Henry! Why would you get rid of my manager who is such a great boss?? That’s so wrong!” It is also why executives often feel they are being unfairly evaluated. Most of them succeeded in their earlier careers by being a good boss. That is how most junior and middle managers are evaluated. But then the rules changed on them. They become evaluated on much more than being a good manager.

Another version of this contrast is a person’s skills versus their output. Most employees are hired, at least initially, for their skills. In contrast I am not hired for my skills. I’m hired purely for what I can do with them. This is why employees are shocked when a talented executive is departed. “Henry! How can you let such a talented executive go?? We wouldn’t let a talented junior financial analyst go so easily!”

Of course execs are talented. They wouldn’t have become execs if they weren’t. But like some professional cyclists are faster on the flat courses and others are faster in the mountains, some execs have trouble translating their talents into performance in our terrain. It is the rare and versatile Tour de France winner that can win in a variety of terrains. And execs at Carta have to succeed in a variety of terrains.

Which brings me to my perspective on what it is like to be an executive at Carta.

A true meritocracy
If a junior employee makes a mistake, as long as they are doing their best, we forgive the mistake and call it a learning opportunity. Executives are given much less leniency. Executive mistakes are expensive. The margin for error is low.

The expectations are also high. Being an executive at Carta is, and should be, a meritocracy. To understand how meritocracies work, and how hard they can be, it is worth listening to Tony Romo’s press statement when he was replaced as the starting quarterback for the Dallas Cowboys. One of the most poignant moments was when he described football as a meritocracy.

You see football is a meritocracy. You aren’t handed anything. You earn everything every single day, over and over again. You have to prove it. That’s the way that the NFL, that’s the way that football works.

Carta is a meritocracy. Especially at the executive level. Executives, including me, have to earn the right to play every single day. That is what the team deserves.

Most people want to be part of a meritocracy. Until they are. It is difficult for most people to hear they are not doing a good job. It is especially hard for executives because they have been successful at almost everything they have done in the past. That’s how they got to being an executive in the first place.

For many, failing is such a rare occurrence in their careers that it is almost incredulous. They are convinced it can’t be them. It must be the ceo, the other execs, or the company itself. They are like the the elite peewee child football player that goes on to becoming a junior highschool star, highschool star, and college star, but then struggles in the NFL and blames the league. What’s wrong with the coach, this team, or the NFL??

When I’m having a departure conversation with an exec they almost universally tell me I am making a mistake. They’ve been successful their entire career. Why wouldn’t they be successful now?? It must be that something is wrong with me, the other execs, or Carta.

I tell them they could be right. I could be a bad coach and not seeing how great they really are. I don’t have a monopoly on being right. But I ask them to give me the benefit of the doubt and reflect on their role in getting us to this point. Even just for a day. Otherwise there is nothing to learn from the experience at Carta.

Please listen to or read Tony’s transcript. It is one of the best words a human has ever said about being part of an elite team.

An unfair fairness
It may seem unfair when an executive, especially your executive, leaves. But keep in mind a couple of things. First, they are paid a lot of money. Second, they choose to be an executive. Part of being paid a lot of money is that you have to earn it every day.

It may seem unfair to the executive to depart them if they are not producing results. But think of the unfairness to everyone else if we don’t. Employees, shareholders, customers, future customers, and all the people we haven’t touched yet, lose if we don’t make hard decisions. And these are very hard decisions. I can assure you these decisions do not come easy. To take away someone’s livelihood, to impact them and their families, to impact the employees they work with, is personally angst ridden, anxiety provoking, and saddening. It is the worst part of my job.

But Carta, and the future we are building, is bigger than any one of us. I have to remind myself of that. And that goes for me too. I hope I get to work at Carta until I’m too old to. But Kings and Queens rarely die a natural death. We see the great founder/ceos of our generation, Gates, Jobs, Musk, Bezos, Zuckerberg, that go the distance. They are the exceptions that prove the rule. Most founder/ceos don’t go the distance. Statistically, I am more likely to be fired from Carta than retire from it.

So I have to earn it every day, too.