Why successful leaders stall: temptations, fatal flaws and pitfalls

Success creates cover. The stall rarely arrives as a scandal. It arrives as comfort after a win: the formula that just worked, the room that has learned not to contradict you, the calendar that proves you are still essential. I have held that role across more than 25 years as CEO, and I now sit with people who are still winning on paper while something in the operating system has already started to idle. The numbers can look fine for a long time. That is the danger.

I group three focus areas because they are one sequence, not three seminars. Temptations of successful leaders are the invitations — the pull towards ease, certainty and self-protection when the applause is still warm. Fatal flaws of leaders are what those invitations become when they harden into a pattern other people pay for. Leadership pitfalls are what the culture copies once the pattern has a title and a parking space. Temptation, flaw, pitfall. The diagram at the top of this chapter is the whole argument in one line.

Jack Zenger and Joseph Folkman said the quiet part in 2009: poor leadership in good times can be hidden; poor leadership in bad times is a recipe for disaster. They were looking at 360-degree feedback, not at a mood. If you only inspect the chief executive when the quarter misses, you will be late. The work is to see the temptation while the numbers still flatter you.

Two other facts sit on my desk when I talk about stalls. The Center for Creative Leadership has spent decades on derailment — promising careers that come off the track. An inability to form strong interpersonal relationships, built on trust and mutual understanding, is one of the patterns they keep naming. And Gallup, in a study of 7,272 U.S. adults, found that one in two had left a job to get away from their manager. Managers also account for at least 70% of the variance in engagement scores. The stall is not a private aesthetic problem. It leaks into whether good people stay.

This chapter is not a diagnosis. I do not treat burn-out, and I do not replace a clinician; if what you are seeing looks like a health matter, stop reading me and get qualified help. I will name the invitations that follow a win, the flaws that end careers, and the pitfalls that tax a culture after the applause — then ask you to put a sensor on the one already in the building.

Temptations of successful leaders

The temptation of a successful leader is to protect yesterday’s formula and call it standards. Growth breeds comfort. Comfort dresses itself up as wisdom.

I watch this after a good year more than after a bad one. A bad year at least keeps you curious. A good year gives you evidence that you were right. The room learns to bring you confirmation. The diary fills with people who need you to remain the person who just won. Herminia Ibarra described a cousin of this as the authenticity paradox: clinging to a familiar self can stop you becoming the leader the next chapter requires. After a win, “this is just how I lead” is not integrity. It is often nostalgia with a P&L.

The invitations are predictable. I will name the ones I see in the chief executive role, not as a museum of other people’s sins, but as a checklist you can run on yourself this month.

Certainty. You stop asking what could derail us. Pre-mortems feel like negativity. Devil’s advocates feel like disloyalty. The last strategy worked, so questioning it feels like ingratitude. The tell in the working week: the same three people speak, the same frame wins, and “we already decided this” closes rooms that should still be open.

Heroics. You remain the person who can personally rescue the week. The company lets you, because it is easier than building an owner. You call that high standards. It is a refusal to scale. After a win, heroics get rewarded in public, which trains the next layer to wait.

Insulation. Good news travels towards you; bad news waits for a better moment. You are busy. You are travelling. You have earned a little protection. Direct reports start managing your mood. That is not loyalty. That is how you become the last to hear. I wrote a longer treatment of that isolation as a design problem, not a personality flaw. The temptation is to leave it undesigned because the quarter was kind.

Appetite for the familiar. You hire for pace and likeness. You resource the product you already understand. You decline the market that would force you to be a beginner again. Comfortable competence is a narcotic. It feels like focus. Sometimes it is focus. Often it is fear of looking average in a new room.

The calendar as proof. You start advertising hours. Presence becomes costume: looking busy instead of landing a decision. After a win, busyness can look like commitment. It is frequently avoidance with better lighting.

Exemption. The rules you wrote for everyone else develop a quiet clause for you. You skip the operating review because you were “in it all week”. You rewrite the deck at midnight and call it care. You keep a shadow channel into a function that has an owner. Success makes the exemption feel earned. The team experiences it as the real org chart.

The lamp is not the enemy. The unexamined flight into it is.

None of these require a villain. They require a win and no sensor. Install the guardrails while the applause is still warm: a post-win audit with someone who does not need you to be impressive; a rotating dissent role, thanked in the room; one reverse indicator next to each vanity metric; one ritual you will not skip because you are the boss.

Run the left column against last month, not against your self-image. Temptation is physics. Put friction in while you still have credit. Wait until the numbers turn and the guardrails will look like bureaucracy.

If the “win” has left you flat, humourless and unable to recover, that may not be a temptation pattern. That may be a burn-out risk the board will notice late. Different work. Stay hungry without becoming a hazard.

Fatal flaws of leaders

A fatal flaw is a pattern other people already pay for — and that you can no longer honestly call a one-off. Insensitivity, broken trust, a gap in developing people, a gap in meeting goals, a gap in strategic thinking: those are the ones I keep meeting in the chief executive role. They are not mysterious. They are expensive because success has been covering them.

I do not recite ten flaws as a parlour game. I use the study as a mirror with a date on it, then I work the pattern that is live. In coaching I see a shorter list that still covers most of the damage.

Insensitivity. Not “being direct”. Direct can be a gift. Insensitivity is when the other person leaves the room smaller, and you treat that as their fragility. It shows as public humiliation dressed as candour, humour that always points down, and a tin ear for the cost of your last remark. Daniel Goleman, looking at nearly 200 large global companies, treated emotional intelligence as the sine qua non of leadership — the thing without which technical brilliance does not carry. You do not need his whole model. You need to notice whether people still think in front of you.

Broken trust. Promises that slide. A story that changes with the audience. Credit absorbed; blame distributed. Trust is slow to build and fast to invoice. Once it is broken at the top, every process becomes a workaround. People copy the workaround and call it culture.

Not developing people. You still like talent. You just do not spend the hours that turn talent into a bench. Feedback is annual, generic or missing. High performers get more work instead of a path. Pretenders stay because the conversation would be awkward. The Center for Creative Leadership keeps returning to the human side of derailment: difficulty building and leading a team, problems with interpersonal relationships. An inability to form strong interpersonal relationships — built on trust and mutual understanding — is not a soft extra. It is how careers come off the rails while the spreadsheet still looks tidy.

Not meeting goals. This one hides in charm. The room likes you. The quarter does not arrive. Failure to deliver is a breach of trust even when everyone enjoys the meeting. CCL is blunt: even someone great with people is in jeopardy if they do not drive results towards business objectives. Charm without a scoreboard is a flaw with better manners.

Thin strategic thinking. You are still the best operator in the building, and you have made that your identity. The next horizon has no owner. Adjacent bets are either impulsive or endlessly deferred. Vision and direction were on Zenger and Folkman’s list for a reason. A leader who cannot point is a leader whose team will invent their own map — or wait.

Not walking the talk. The values on the wall and the exemptions in your diary. This is the flaw teams spot first and name last. They will not put it in the engagement survey. They will put it in the corridor.

Not learning from mistakes. The post-mortem that is actually a defence. The same miss with a new excuse. If you cannot extract a lesson and change a behaviour by a date, you are not experienced. You are repetitive.

A blind spot and a fatal flaw are cousins, not twins. A leadership blind spot is something you cannot see and others have not yet named safely. Tasha Eurich found that 95% of people think they are self-aware and only 10–15% are — which is how flaws stay fed. A fatal flaw can be visible, including to you, and still practised. “I know, I know” is not repair. Repair is a different working week, with a witness.

A flaw is a pattern you can still turn from. A pitfall is when the path itself starts to crumble.

What to do with a live flaw, without theatre:

Name it in one sentence a direct report would recognise. If they would not, you are still in self-mythology.

Put a sensor on it. For insensitivity: a standing question after hard meetings — “What did I miss about how that landed?” For broken promises: a visible list of commitments with dates, reviewed weekly. For developing people: two hours a week that cannot be stolen by a fire you should not be fighting. For goals: a board you cannot charm your way around.

Practise the replacement in the room that matters, not in a journal. If the flaw is interrupting, the replacement is a closed mouth for the first ten minutes of the next operating review. Small. Dated. Inspectable.

Ask someone who will not lose their job for telling you the truth. If you have no such person, that is already the stall. Design it. Do not wait until you are lonely and calling it resilience.

If several rows sting, do not pick them all. Pick the one the people closest to you would pick. Then tell them you are working it, and give them permission to catch you. Unannounced self-improvement is how leaders stay in the 95% who think they are self-aware.

Can a high performer with a flaw be coached? Often, if they will look at the receipt. I will not sand off a personality, and I will not promise the board a new human. I will put a sensor on the pattern and practise a different working week. If they will not accept that others pay for the pattern, you do not have a coaching brief. You have a decision. Delaying that decision is how a flaw becomes a pitfall with a department around it.

Leadership pitfalls

A pitfall is what the organisation copies once the leader’s pattern has been normalised. Temptation is private. A flaw is personal. A pitfall is cultural. That is why it is so expensive, and why it is so easy to miss while the applause is still on the website.

I use “pitfall” for the traps that damage a career, a culture and an organisation at the same time. Isolation. Signal overload. Short-term tunnel vision. Heroics as a system. Polite silence. Each one starts as a reasonable response to a real pressure. Each one, left in place, teaches the company the wrong lesson.

Isolation as an uninsured risk. The chair withholds honest mirrors: the team manages you, the board samples you, your peers are also your market. That is structural. Leaving it undesigned is the pitfall. You delay irreversible calls because there is no one to pressure-test the frame. You over-share with the wrong audience. You go flat, and the company reads it as strategy. Trust under pressure is the later chapter on earning trust and having the conversation you have been postponing. Here the point is simpler: if you have no place to think, the stall will look like a personality until it is a number.

Signal overload. Everything arrives as urgent. You become a sorting office. The pitfall is not the volume; it is using volume as a substitute for Choices. The team learns that the way to get airtime is to escalate. Your diary becomes a museum of other people’s adrenaline. Short-term tunnel vision is the cousin: this quarter’s fire is always more vivid than next year’s capability. You can be busy, admired and slowly obsolete.

Heroics as a system. What began as your temptation is now how the company runs. People wait to see whether you will enter the channel. Owners do not own. The bench does not form. When you finally try to step back, the place wobbles, and you take that as proof you were needed. It is proof you built a pitfall and called it standards.

Polite silence. Gallup found that one in two people in their study of 7,272 U.S. adults had left a job to get away from their manager, and that managers account for at least 70% of the variance in engagement. People do not always fight. They leave, or they stay and stop telling the truth. A culture of manners around a flawed chair is a pitfall with a retention cost. You will not see it in the all-hands. You will see it in who declines to join, who declines to stay, and who has already gone quiet.

The cover of good times. Zenger and Folkman’s warning again: poor leadership in good times can be hidden. A rising market, a legacy product, a heroic sales lead — any of these can hide a pitfall for years. Then the cover comes off in a single quarter and everyone is shocked. They should not be. The corridor knew.

CCL’s derailment work is practical if you refuse to treat it as a poster: difficulty adapting to change, building and leading a team, delivering results, a narrow strategic orientation, and problems with interpersonal relationships. A pitfall is usually one of those five, installed as “how we do things here”.

Success creates cover. The stall starts as a temptation, hardens into a flaw, then becomes a cultural pitfall.

Catch it early. The same irreversible call on the agenda for the third time. Rescue behaviour into a function that has an owner. Humour and curiosity leaving the table. A capable person leaving because they could not get near the truth. The real plan living in the corridor.

Course-correctors I actually use: a small council allowed to disagree with you on a cadence; a day of “what would we not do again”; a talent look that names pretenders; a diary rule that protects thinking time the way you would protect a customer. None of this is original. All of it is rare in a company that is still winning.

If the stall is shading into depletion, read the signals as operating facts, not as a moral tale. This chapter will not fix a health problem.

Boards have a job here they often duck. They wait for a miss, then they commission a review. Earlier signals were available: the CEO joining meetings they used to delegate, the jokes dying, the same call slipping a month. A chair who will not let the board see how they are running the role is already in the isolation pitfall. A board that only wants theatre is helping.

Reflection questions

Answer these on paper, then ask one person who will not need you to be impressive to mark where you are lying.

1. After the last real win, what did I stop questioning — and who has started protecting my mood?
2. Which pattern would the people closest to me name as the one they already pay for, and what would a different working week look like this month?
3. Where has a personal exemption of mine become “how we do things here”?
4. If a capable person left in the last year, what did they say in the last honest conversation, and what does that have to do with me?
5. What support have I actually designed for the isolation of the top job — sparring partner, peer truth, a board conversation that is not theatre — and what is still wishful?

If the cover is still on and you can feel the idle, bring the live pattern into a room that is allowed to tell you the hard thing. I will not sell you a personality transplant. I will work the temptation, the flaw with a receipt, and the pitfall the culture has started to copy. Book a 30-minute strategy call when you are ready to name the one you are already in.