Leadership and Self-Deception: Are You Getting in Your Own Way?

The leader who can't see the problem is, often, the leader

Most leaders I sit with don't come in saying, "I think I'm the problem." They come in describing a situation. A team that isn't performing. A peer who keeps undermining them. A board that doesn't understand the strategy. A direct report who needs to be managed more carefully than anyone else.

What they want, when they first come in, is a way to handle the other people in the situation more effectively.

What we usually find, somewhere between the third and tenth session, is that the situation they're describing has been quietly running through one lens the whole time. Theirs. And that lens has a few smudges on it they couldn't see from inside.

That's the territory of leadership and self-deception. Not lying to yourself in any obvious way. Not denial in the dramatic sense. Just a quiet, well-organised inability to see how you're contributing to the very thing you keep saying you want to fix.

This piece is for people who lead other people. Founders, partners, senior managers, heads of teams. It’s especially for those of you who got here fast and now find yourselves wondering why everything that worked before isn’t quite working the same way anymore.

What is self-deception in leadership?

Self-deception, in the leadership context, is the gap between how you're showing up and how you think you're showing up. It's the difference between the version of you that exists in your own head and the version of you that other people in the room are actually experiencing.

Most of us assume those two are roughly the same. They're not.

You think you're firm but fair. The person across from you experiences you as dismissive. You think you're being direct because you respect their time. They experience you as impatient. You think you're holding the team to a high standard. They experience you as someone they have to perform for, which makes them less honest with you, which makes them harder to manage, which confirms your belief that the team needs to be held to a higher standard.

The loop is the trap. And the trap is closed from your side, because you can't see the part of yourself that closes it.

This isn't about incompetence. Most leaders I work with are highly capable.

Self-deception isn't a skills problem. It's a perception problem about the self. And it gets worse, not better, with seniority, because as you rise, fewer people are willing to give you the kind of unfiltered feedback that could puncture it.

The cleanest definition I've found is this: self-deception happens when you stop being able to consider the possibility that you are, in this specific situation, part of what's not working.

How self-deception shows up at work

Once you start watching for it, you'll see it everywhere. It tends to wear a few familiar costumes.

The first is the explanation. Every difficult conversation becomes a story about why the other person didn't get it. "He just doesn't understand the bigger picture." "She's too junior to see what I'm doing." There's always a reason the friction is coming from them.

The second is the over-effort. You start working harder to compensate for the team you don't trust. You take on more. You review more closely. You become quietly resentful that no one else is putting in what you are, which confirms your belief that you're the only one carrying it, which makes you trust the team less. The team, sensing they're not trusted, performs to that ceiling. You read this as proof they were never going to step up.

The third is the polished public version. You give a clean answer in a board meeting about why the last quarter underperformed. You take responsibility in language. But internally, the story is intact. It was the market. It was the team. It was the timing. The taking-responsibility was performance, not posture.

A lot of the time, what looks from the outside like a confident leader is, on the inside, a person who can no longer afford to examine themselves too closely. Because if they did, the architecture of how they've been operating would have to shift. Self-deception in leadership is most often a coping mechanism that started doing its job well and then forgot to retire.

The 'box' concept: seeing people as objects, not people

There's a framework, popularised by The Arbinger Institute, that's hard to improve on for explaining what self-deception does to your relationships at work. They call it being "in the box."

When you're "in the box," you're seeing the people around you as objects. Things to be managed. Resources to be deployed. Obstacles in the way of your goals. People who exist primarily in relation to what they can do for you.

When you're "out of the box," you're seeing the same people as people. Beings with their own concerns, their own pressures, their own logic, their own dignity. They are not characters in your story. They are the centre of their own.

It sounds soft. It isn't. The shift between the two states is the single most

consequential thing in how a team performs around you.

When you're in the box around someone, they feel it. They may not be able to name it. But they sense, accurately, that you are not actually curious about them. And once they sense that, they start protecting themselves. They tell you less. They stop bringing the real problems to you, because the real problems require you to see them as people, not just as roles, and they can tell you aren't quite there.

You'll notice you have a different version of yourself for the assistant, the senior associate, the partner, and the client. Different not just in seniority of address, but in actual humanity granted. The amount of "person" you afford them tracks neatly with how useful they are to you. That's the box.

A useful question, if you want to test for yourself: when you think about a difficult person on your team right now, what comes up first? Their inadequacies, or their context? Both can be true. But which arrives first tells you where you are.

Leaders who struggle to examine themselves honestly are often confusing self-awareness with self-attack. How to Overcome Self-Doubt explores this distinction more deeply.

Signs you might be deceiving yourself as a leader

You won't always know. That's the nature of the thing. But there are some quieter patterns.

The same kind of person keeps "underperforming" on your team. Different hires, similar pattern. The variable, if you're willing to consider it, might not be them.

You can't think of a recent moment when a direct report meaningfully changed your mind about something important.

You give feedback in a way that you describe as "candid" and that they describe, when they're honest with someone else, as "harsh."

You hold the team to standards you don't hold yourself to. You're allowed to be tired. They aren't.

You notice that the people who do well on your team are the ones who don't disagree with you much. You read this as proof of your good judgement in hiring. It might also be proof of an environment where disagreement gets quietly punished.

When something goes wrong, your first instinct is to map blame. When something goes right, your first instinct is to assess what you did to make it happen.

You leave most meetings sure that you were the most reasonable person in the room.

If four or more of these feel familiar, the loop is running. It doesn't mean you're a bad leader. It often means you're a high-performing leader whose strengths have outgrown your self-awareness.

How self-deception destroys team trust and performance

There's a quiet, expensive cost to leading from inside the box, and it shows up in three places.

The first is in the speed at which information moves toward you. In a healthy team, problems surface early, while they're small and cheap. In a team led by someone who can't be honestly told things, problems surface late, when they're large and expensive. Teams operating under constant emotional pressure often drift toward patterns of exhaustion and quiet disengagement that look like performance problems on the surface. I wrote more about this dynamic in Burned Out or Overworked? How to Tell the Difference Before It Costs You Your Health.

The second is in the kind of talent who stays. People with strong sense of self, the ones you most want to retain, tend to leave environments where they're not seen as full humans. They leave quietly. They don't usually tell you the real reason. Over time, you end up with a team disproportionately made up of people who can tolerate being underseen.

The third, and most damaging, is in your own access to reality. Every leader needs a few people who will tell them the truth about themselves. If you've spent years in the box, you've also been training the people around you not to do this. So now, when you most need it, the truth isn't reachable.

For younger leaders in fast-moving markets like Singapore, there's an added layer worth naming. If you stepped into a leadership role in your late twenties or early thirties, you may have absorbed your style from people who were operating from inside the box at scale. What you learned to imitate was their coping mechanism, not their wisdom. That's worth knowing, gently.

Practical steps to get out of the box

This is slow work. Anyone who promises a quick shift is selling you something. What follows are practices that, applied with patience, make the loop visible to you.

The first is to start noticing your stories. Pick one person on your team you've found difficult lately. Before your next interaction with them, write down, in two or three lines, the story you're carrying about who they are. Now ask: is this the only possible reading of the same set of facts? Sit with that for a minute before you walk into the room. You'll be surprised how often you arrive less rigid than you would have.

The second is to separate the role you're playing from the person you are. You behave a certain way as the head of the team. None of that has to disappear. But notice how often you've stopped being able to drop the role. The identity has merged with the function. When that happens, every piece of feedback feels existential. Loosening that fusion is one of the most freeing things a leader can do.

The third is to ask better questions of yourself in difficult moments. Most leaders, when something goes wrong with a person, ask "what's wrong with them?" The question that actually changes things is "what might be going on for them that I'm not seeing?" Same situation. Different door.

A surprising amount of reactive leadership is actually driven by unmanaged anxiety at work rather than clarity or decisiveness. If this pattern feels familiar, Why Work Anxiety Makes Even High Performers Feel Constantly Behind explores this more deeply.

The fourth is to find one person who can tell you the truth and protect that relationship like it's expensive. A coach, a therapist, a peer who is structurally outside your reporting line. Someone whose feedback can't cost you anything materially. The absence of such a person is, in itself, a sign you've been managing your environment to keep difficult truths at a distance.

The fifth is to start saying less. Senior leaders talk a lot. They explain. They direct. Sometimes this crowds the room. The team can't think out loud, because you've already thought out loud, and they've absorbed your shape of the answer. Try, in your next three meetings, holding your view back until after two other people have spoken. Watch what happens.

The sixth is the smallest and the most powerful. The next time you find yourself building a case against someone in your head, mid-day, just notice it. Don't fight it. Don't try to be more generous. Just notice. Every time you catch yourself in the loop, the loop loses some of its hold.

Leaders who can’t extend grace to themselves rarely extend it to their teams either. Why Giving Yourself Grace Is the Most Underrated Form of Self-Love explores this dynamic more deeply.

Why executive coaching accelerates this shift

You can do some of this work alone. People do. But the limit is built in. The thing you can't see by yourself is the thing you can't see by yourself. That's the central problem of self-deception. The very mechanism that lets the loop run is the same mechanism that lets you keep believing you've already considered it.

This is why executive coaching, when done well, isn't about strategy or frameworks. It's about creating a relationship in which the things you can't see in yourself can be carefully, kindly, surfaced. A good coach doesn't tell you what's wrong with you. They sit with you long enough that what you've been avoiding starts to show up on its own.

The work moves through three rough phases. First, the things weighing on you have to come up. The pressure, the unspoken doubts, the parts of the role that are quietly exhausting. This is often called therapy, even in a coaching context.

Then, once that's cleared a little, the patterns can be looked at. Why you respond the way you do under pressure. Why this specific kind of person keeps appearing on your team. This is the counselling layer.

Only then can the third phase begin. This is the part that actually deserves the name "coaching." It's about who you want to become as a leader. The deeper version. The one your future team will be shaped by.

Most leaders I sit with arrive thinking they need phase three. What they almost always need first is phase one. And the difference, made early, saves them years.

For readers interested in the original framework behind ‘the box’ concept, The Arbinger Institute’s work on leadership and self-deception remains the foundational reference.

People also ask

What does self-deception in leadership actually mean?

Self-deception in leadership means losing the capacity to see how you're contributing to a problem you keep trying to solve from the outside. It's not lying. It's a quiet inability to consider that you might be part of what's not working. Self-deception is rarely about being a bad leader. It's about being a leader whose self-awareness hasn't grown at the same speed as their authority.

How do I know if I'm being self-deceptive as a leader?

Watch for patterns. If the same kind of person keeps "failing" on your team, if direct reports rarely change your mind, if the people you trust most are the ones who agree with you most, and if you tend to leave meetings sure you were the most reasonable person in the room, the loop is probably running. Another signal: you've stopped having recent memories of being told something hard about yourself by someone you respect.

What is "the box" in leadership and self-deception?

The "box" is shorthand from The Arbinger Institute's work. When you're "in the box," you're seeing people around you as objects or functions. When you're "out of the box," you're seeing them as full human beings with their own concerns and dignity. The shift between the two states is the difference between a team that gives you their best thinking and one that protects itself from you.

How does self-deception affect team performance?

In three main ways. Problems surface late, because no one feels safe surfacing them early. Strong talent leaves quietly. And your own access to honest feedback narrows over time, because the people around you have learned that telling you the truth costs them something. The financial impact of these three is usually large and usually invisible until something breaks.

How long does it take to genuinely change?

You'll notice subtle shifts within a few weeks if you actually do the practices. The deeper change, where your default operating mode moves out of the box more often than into it, takes six to eighteen months of consistent work. The leaders I've watched make this shift describe it as finally being able to access the version of themselves they'd always wanted to lead from.

A closing note

Leadership and self-deception isn't a flaw in your character. It's a structural risk of being in a senior role for long enough. Almost everyone who leads for a meaningful stretch of time falls into the loop somewhere. The question isn't whether you're vulnerable to it. The question is whether you have the support to notice when you're in it, and the courage to do something about it before it costs you the team you spent years building.

The leaders I respect most are not the ones who never sat in the box. They're the ones who climbed out and remembered, with some humility, what it had cost them while they were in it. That memory tends to make them better. Gentler. More effective.

If something in this piece felt familiar, that recognition is already the beginning of the work.

If you've read this and noticed yourself, I work with senior leaders, partners, and founders on exactly this kind of inner shift through one-on-one executive coaching. The work is private, deep, and paced to your real life. Write to me if it feels right.

Let’s have a conversation

10min

Book Now