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What it’s Actually Like to Be a CEO

Amidst the epidemic of distrust and demonization that is sweeping our society right now, there are figures that don’t typically engender much sympathy or empathy. Politicians, media executives, rich people, and CEOs might top that list.


But when we dehumanize people we harm our wisdom, and those frequently reviled targets play vital roles in our societies, so the better we understand them accurately, and not through the lense of some caricatured cognitive distortion, the smarter we’ll be at understanding and changing the world.


I have never been a politician, a media executive, or rich, but I have been a CEO. Granted, of just a mid-sized nonprofit organization, so not quite the typical villain - I’ve spent most of my career as an activist throwing shade on big corporate CEO types. But both my own experiences and my experiences advocating with some of those ‘villains’ have led to me an increasingly empathetic perspective. Let me explain.


CEOs are just people, like anyone else. They are not really special in any particular way. Contrary to popular opinion, they’re not highly likely to be ruthless and devious, certainly not in the nonprofit sector, and even in the corporate sector it tends to be the ‘nicer’ folks that are able to keep both their boards and their teams happy enough to be productive.


I campaigned for a decade in a way that treated Monsanto like the Death Star of global biodiversity. Then I met the CEO, and spent a few hours with him. He was a genuinely nice, thoughtful guy, who genuinely believed he was helping to feed the world. I found him open to my arguments, and much to my surprise I found he and his colleagues had a mirror image of me, as a nonprofit CEO, making money by misleading people with enraging falsehoods that in some ways damaged democracy.


I remember when I met with a group of oil company CEOs, perhaps the easiest to demonize. But many of these people came from families who had worked in energy for generations - they saw themselves going into the wilderness and braving many risks and hardships to generate the energy that powers our civilization. They recognized the need to switch to sustainable sources, but much to my surprise they saw their work as a noble calling without which we would almost all be dead.


This is just to say that people aren’t really evil, and usually feel they’re doing the right thing, and CEOs are no exception to that, in my experience.


And while they may not be extraordinary people, they often face extraordinary challenges. I was extremely lucky to have an amazing board and team that I loved dearly. But even in my case, being CEO was no cakewalk. I want to highlight some of the challenges in this post, not to suggest that being a CEO is a nightmare, but just to help balance what I feel is an inaccurate popular picture.


Depending on how much you delegate, being a CEO can be intense. Any job can be, but the level of responsibility placed on you as a final decision-maker is somewhat unique. All the hardest, toughest problems come to you, and there’s lots of them. And you never have much time to deal with any of them, because there’s so many others to deal with. And you’re in a constant fight to not be ‘reactive’ to problems and focus on your proactive and creative agenda.


Part of the reason it’s tough not to be reactive is that you know that even if you absolutely nail 50 or 100 or 1000 tough decisions and thread tricky challenges or come up with that breakthrough idea, the one big mistake you make is all that anyone will care about, talk about, and judge you on.


I’ve long felt that ‘holistic evaluation’ is essential to wisdom. If you go around judging yourself or others by any single negative data point you come across, you’re going to have a highly dysfunctional view of the world. But our media and culture generally does not even remotely practice holistic evaluation. Have someone who has spent an entire lifetime of public service engaged in excellent work? Totally irrelevant if they said or did something offensive in the view of somebody else. Won’t even be worth a mention in the story.


And this dysfunctionally negative lense applies not just to the thousands of decisions you have to make, but the ones you don’t make, the ones your team makes, and to everything you say or do professionally or socially. You are constantly under scrutiny.


But that’s fine because you have all the power right? That’s what  being a CEO means? Wrong. It varies by the person, but CEOs are often highly constrained by large numbers of stakeholders and players, who may also have conflicting desires or agendas that the CEO must manage. You’re constrained, first, by your board and governance and investors and funders. Second by the media and brand risk and critics and activists. Third by partners and peers with whom reputation is important. Fourth by an immense thicket of legal regulations in many areas that it requires highly paid experts just to understand. Fifth by budget and finances. And sixth, and most importantly in some ways, by your own team.


This last one is worth explaining. There’s an image of CEO power in which the CEO says jump and any team member asks how high. Maybe that was true at some point in the past. But today the dynamics of a modern workplace are very different. First, you’re acutely aware that if you want to do a good job, the morale of your team is all-important. It’s like this precious flower that needs constant and careful tending to bloom. Each individual person needs a lot to stay motivated, but a team is a more complex and fragile entity, where even one or two people in a bad place can affect morale. The team morale ‘flower’ can be tremendously vulnerable. And it is *constantly* under assault.


At any given time, 25% of us are experiencing a diagnosable mental illness. Across our lives, 50% of us will. Even when we’re not struggling with a challenge like that, life events are constantly knocking us into darkness and negativity - breakups, loss of loved ones, failures, health issues, jealousy, conflicts. These things can be enough to knock us completely off our game, to spiral into dangerous conflict with colleagues or make serious mistakes that harm our work (mistakes that the CEO will often be held accountable for).


I would estimate that someone has some major adversity like this, on average, once every 2 years, lasting say up to 3 months. That means that at any given time, you’ve got 10-15% of your team going through some period like this. We all know how crazy and complicated we humans are, but we typically only really see through the masks we put on when we’re in close relationships with people, friendships or romantic relationships. But as a CEO, you get a real sense of this more generally - because personal hardship almost always manifests in one way or another in the workplace.


You can respond to this with a kind and wellness-focused culture. But that doesn’t necessarily help, especially lately. Increasingly our culture embraces “emotional reasoning” in which we are encouraging each other to believe that our strong negative feelings necessarily correspond to some external facts or reality. So when someone is unhappy or anxious, it’s someone else’s fault. Ironically, the more kind and caring you are as a workplace, the more you can get blamed, at least for not ameliorating any discomfort someone is feeling.


I’ve been struck for example by some recent resignations of CEOs after staff members committed suicide. All our psychologists tell us that depression is an illness and that blame for suicide isn’t appropriate. The victim’s parents, siblings, friends, romantic partners, exes, are all absolved of blame, even if they were in conflict or abusive. But the victim’s workplace? Guilty.


There's another major problem with having a kind and caring workplace to help your team do their best despite life's hardships: attachment. Relationship psychology and organizational behaviour have recently merged to study attachment at work. All the research suggests that the more attachment (the more trust, more affinity, deeper relationship) steadily breeds more excellence. That is, until the employee leaves. When 'relationship dissolution' is even contemplated (regardless of whether it's quitting or being fired), the consequences tend to be driven by the person's attachment style. People with a secure attachment style tend to leave constructively. People with other attachment styles can behave in less constructive ways, and those can include retaliation.


This used to be a temporary hardship because workplaces were physical places that you physically left when you left the job. But now teams and workplaces are increasingly virtual and exist on social media. So in the Facebook age basically the people who leave or are fired congregate around a permanent virtual office water cooler in the center of your 'office', and the most irked of them form a filter bubble that is keen for gossip that confirms the worst beliefs of their former bosses, which they then spread to your existing team, board and partners. And this water cooler group isn't small. A normal healthy organization might average around 5 years tenure per staff member, or retain 80% of its staff each year. That's 20% of your team going through relationship dissolution each year and joining the water cooler club.


And this brings me to a major CEO terror - Human Resources. If someone makes a complaint of some kind of mistreatment, it can tie you up in legal and administrative process for months, and have a profoundly dispiriting effect on your team. If a full scale investigation is launched you can be disabled as a CEO for months. If they threaten to go public with their complaint, your board can drop you like a hot potato. It’s worth stressing that their complaint doesn’t have to be fair or true. Once they make it, you are legally extremely constrained about what you can do - anything you do that that employee might regard as negative - such as not promoting them or making some negative comment - can be seen as ‘retaliation’ for making the complaint, which is illegal, and will certainly cost you your job. And while anyone else is free to coordinate and lobby for their perspective, you can be strictly barred from any relevant contact with your team or board or others while an HR process is underway.


Human beings vary by personality and by what psychologists call “affectivity”. People who are high in “negative affectivity” are far more likely to be critical, to distrust, to negatively misperceive people and events, and particularly to regard powerful figures like CEOs in the worst of lights. They're also much less likely to have secure attachment styles. Many CEOs I know spend much of their time in constant caution if not fear of those on their team that lean toward this kind of orientation.


Some of those people are aware of that power, and milk it. A significant percentage of people (and interestingly, a much higher percentage of those on the political far left and the far right) share the ‘dark triad’ traits of subclinical psychopathy (cynicism, callousness, low or selective empathy), Machiavellianism (ambition, cunning, deception), and narcissism (entitled self centeredness). These people can be dangerous to any human endeavour, whether they be at the top of the team hierarchy or the bottom, and can easily game HR processes for their ends. The private sector has evolved a number of practices to game HR constraints in favour of managers, for example by constantly writing up employees for small violations, so they can be fired for cause at any time. But in the better organizations, and in the nonprofit sector, I think it’s not an exaggeration to say that in some important ways the constituency of the highly negative run the show - they determine the boundaries of what’s possible - anger them, and the CEO is out.


This can often put a straightjacket on the decisions and changes you want to make as a CEO. You see what’s wrong, what could be improved, but people fear and dislike change. And laying people off in particular is an earthquake to that fragile flower of team motivation you are constantly tending. This is why most organizational change processes fail, and why standard practice is to bring in a ‘change CEO’ to take the brunt of the hatred and then leave, allowing a fresh face to come in.


Sometimes the animosity you get as a CEO seems unhinged, unreasonable. The kind of stuff politicians get all the time. I think once powerful people are dehumanized it’s open season for conspiracy theories and vitriol. But I’ve also spoken to psychologists who talked about our complex relationship with power. Often our relationship to external power is a mirror image of our relationship with our own power. When you are uncomfortable with your own power you can feel strong animosity towards someone with power, especially if they seem comfortable in it. These dynamics can go even deeper, with many people projecting their parental relationships onto their bosses, with all kinds of weird effects. Ironically, these effects can be even stronger the more respected you are by your team. What this means in practice is that to be a CEO is to be constantly wading through the emotional projections of others, much like any person must, but more intense.


And it is intense. If you have a large team, you may only speak individually to a given team member once every few months, or even years. To you, it’s a brisk comment as you’re rushing to a high-stakes meeting with a splitting headache and have got a thousand things on your mind, and you’ve forgotten it one minute later - to them, every word you say could be remembered (or misremembered) for years and have a potentially profound effect on their view of you and the organization. When you say something that bears on them, the effect is even more intense. Because rightly or wrongly they feel you have ultimate power over their livelihood, so all their fears and insecurities as well as hopes and dreams can get engaged with what you say. For these reasons, a lot of CEOs try to be “Chief Encouraging Officer” and only say positive things to most staff. Saying something negative, even if it’s fair feedback, can have disastrous consequences and generate deep antipathy in some cases.


But, you say, you can’t be a good leader if you want to be liked all the time right? If you try and please everyone you won’t get anything done.


This is where the board comes in. CEOs are not the boss, unless it’s a 100% privately owned company. The board is the boss, and the CEO is an employee like everyone else. In the nonprofit sector the board is typically a group of people who are required by law to be somewhat independent, which means they don’t have much skin in the game in the organization. That means that if anyone targets them with some kind of leverage or actual or threatened bad publicity, they are faced with a cost benefit analysis that is heavily weighted towards making the problem go away. If the threat is big enough, it’s often far easier for them to rein in or fire a CEO than it is to take the heat for supporting them. In the nonprofit sector, boards are infamously controversy averse and risk-allergic, which massively constrains the scope for CEOs to fire people, innovate and take risks, or make enemies. For a board, the CEO is almost always expendable.


This also makes the nonprofit and corporate sectors tremendously vulnerable to authoritarian movements and tactics, a problem we're seeing unfold in many countries across the world right now. If you wonder why cancel culture (and there are both left and right wing versions of it) is so successful despite the vast majority of people being against it, this is why.


BUT, as a CEO, you can’t just be nice and try to keep everyone happy. Because you are also accountable for results, and that does indeed inevitably mean making some people unhappy, sometimes. Chances are, whatever industry you’re in, it’s not easy. There are competitors, risks, metrics you need to hit or beat, and an overall sense of whether you’re doing poorly, well, or knocking it out of the park. To do well, you absolutely have to fire some people, say no to others, give others tough feedback, make tough and unpopular decisions, take risks, and be willing to fail. You can be a mediocre CEO by keeping nearly everyone happy, but you can’t be a good one. Especially if your ultimate motivation is not to keep your job, but to make a difference in the world.


BUT, to navigate all these challenges well, identify what’s going wrong and when, spot upcoming problems, and even get ahead of disasters, you absolutely need to have a steady flow of accurate feedback from your team. And this is no easy thing to get, especially if it pertains to you and decisions you’ve made. Most people are very hesitant to give critical feedback to their boss.


You can bend over backwards to invite it, praise people who give it, have anonymous surveys etc, but for many reasons (fear of being thought of poorly, wanting to protect a colleague etc) it can be incredibly difficult to get honest feedback and accurate information about the most sensitive matters.


This is triply so for your blind spots, the places where you can’t see the value at first of feedback. Your team can become extremely hesitant to press any point, but it’s often your blind spots which pose the most danger to you and the mission. You can rely on outside experts to kick the tires but they’re expensive and they too can only see so much, and others may be hesitant to share with them, and there’s a million things to be across.


And the real kicker is that when you make tough decisions and say no to people and fire some, it can trigger all the trust and authority dynamics mentioned above that make others far less likely to feedback to you. Your team may talk at length about you on social occasions, and you’ll hear snippets of bizarre and wholly untrue things that come to be believed (some positive, some negative) but getting anyone to actually share it with you much less discuss its truth is a very tall order, often because their colleagues swore them to confidentiality. The CEO is a favourite target of gossip, venting, and disinformation and much of it is beyond your control.


It’s when you combine ALL of these dynamics at once - constant human personal hardships and adversity, complex relationships to authority, hostility to and fear of change, toxic personalities, HR processes and board dynamics, team morale and productivity, exit and former staff, media critics and brand risk, gossip and feedback, legal and financial risks, and the requirements of the mission you serve, and see that they ALL interact with each other in either positive or negative spirals, that you can see how precarious the position of a CEO can be.


So the caricatured image of a CEO is of some arrogant all-powerful psychopath who tramples over people on a whim. But the truth I’ve encountered is more often of good and decent people up against huge challenges, constrained in every direction, and sometimes dancing on the head of a pin in a hurricane trying to accomplish their missions.


The final challenge is that amidst all of this, your job as CEO is to overcome your fears, trust your team, listen to critical feedback, believe in yourself, bring hope and vision, and lead from inspiration and example. To maintain your own “positive affectivity” and motivation and enthusiasm and constantly grow as a leader.


That’s actually a wonderful part of the job, in the sense that it can draw out the best in you, and become almost habit over time. I’m supremely grateful for my own experiences, including of adversity and mistakes, and would recommend the experience to anyone who’s up for a challenge.


I hope that image helps balance the caricatured one, and helps us all be smarter in how we engage with CEOs as we try to build a better world, and better workplaces, together.

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