Temptations of successful leaders: audit the win before it audits you

The hardest conversations I have are rarely after a bad year. A bad year keeps a leader curious. They want to know what went wrong, they read the data, they ask the uncomfortable people into the room. The hard conversations come after a great year, when the board is pleased, the press is kind and the leader in front of me has stopped asking why.

I have held that role for more than 25 years as a CEO, and I know how easy the next move feels after a win. Take the credit, raise the target, repeat the formula. It is only later that you find out how much of the result was timing, a competitor’s stumble or one person on the team you had not fully noticed.

So here is my claim, plainly. The most dangerous week in a leader’s year is the one after a win, because success quietly removes the reason to ask why. Growth breeds comfort, and comfort dresses itself up as wisdom. The answer is not to celebrate less. It is to examine wins with the same rigour you give losses, and to install the guardrails while you still have the credit to do it calmly.

The parent chapter, why successful leaders stall, lists the temptations I see most often: certainty, heroics, insulation, the appetite for the familiar, the calendar as proof and the quiet exemption. This article goes one layer down. Why does success make capable people stop learning, and what exactly do you put in place in the working week to stop it?

Why winning switches off learning

Francesca Gino and Gary Pisano spent years on this question and found three impediments that travel together.

The first is attribution. When we succeed, we credit our talent and our strategy, and give short shrift to environmental factors and luck. When we judge other people’s success, we do the opposite. The second is overconfidence. In one of their studies, managers who were asked to recall a success went on to make more optimistic forecasts and take bigger bets than managers who recalled a failure. The third is what they call the failure-to-ask-why syndrome: success does not trigger the investigation that failure does, so nobody revises the theory of how the business actually works.

Their opening case will be familiar to anyone who has raced. The Ducati Corse team entered MotoGP in 2003 treating it as a learning season, fitting the bikes with sensors and debriefing riders after every race. Then it finished second overall as a rookie. With each success the team focused more on winning and less on learning, and analysed little of the data it was collecting. Confident, it radically redesigned the bike for 2004: more than 60% of the 915 components were new. The bike had serious handling problems. Only the perceived failure of a third-place finish made the team start learning again.

I recognise that sequence from sport and from the boardroom. A rookie season goes well, the team stops reading the data, and the next decision is bigger than the understanding behind it. That is the temptation in its purest form. It is not laziness. It is confidence running ahead of insight, and it is why I insist that winning is an inside job: the scoreboard tells you that you won, never why. Left alone, the same confidence hardens into the fatal flaws that derail leaders.

Jim Collins puts the warning sign in a single contrast. Decline is likely when the rhetoric of success (“We’re successful because we do these specific things”) replaces understanding of why those things work and under what conditions they would stop working. Read that against your last board pack. Which sentences explain the win, and which only repeat it?

There is a personal version too. Rasmus Hougaard and Jacqueline Carter describe the inflated ego that comes with success — the bigger salary, the nicer office, the easy laughs — and the way it narrows your field of vision and makes you easier to manipulate. Their example is a new chief executive handed a key card that took the lift straight to the top floor, past everyone else. Every win hands you another key card. Some of them you should give back.

The three guardrails, built properly

The focus area I work on with clients names three guardrails: rotating devil’s-advocate roles, reverse indicators and post-win audits. Each one sounds obvious. Each one fails in a predictable way when it is installed lazily.

A post-win audit

Gino and Pisano point to the after-action review used by the military, which asks four questions after every significant event regardless of outcome: what did we set out to do, what actually happened, why did it happen, and what will we do next time? The discipline is in the regardless. Most companies only hold the meeting after a miss.

I add one sorting step. List every factor that contributed to the win, then mark each as something you controlled or something the market, a competitor or luck handed you. Gino and Pisano suggest the same classification. The second column is where the danger lives, because that is the part of the result you are about to budget for again.

They also make a point in Why Leaders Don’t Learn from Success that I now repeat to every leadership team after a good quarter: “If the chief lesson of a successful project is a list of things to do the same way the next time, consider the exercise a failure.” Replication is useful. It is not learning.

Rotating dissent

A devil’s advocate who is always the same person becomes background noise within a quarter. A devil’s advocate who is never thanked stops trying. So rotate the role, brief it specifically and reward it in public.

The most useful brief I know is the premortem. Gary Klein designed it for project planning: the team assumes the plan has already failed and generates plausible reasons why. The value is that people with reservations can speak at the outset without seeming disloyal. After a win, that permission matters more than ever, because questioning the formula now feels like ingratitude.

Reverse indicators

Every headline metric deserves a companion that would move first if the headline were flattering you. I ask leaders to put one beside each number they are proud of.

The right-hand column is not a set of targets. It is a set of cross-examinations. If one moves the wrong way for two reviews in a row, the conversation changes. The same thinking applies when you set next year’s numbers: goal setting that works starts from what you understand about the last result, not from the last result plus a percentage.

What the temptation looks like in the working week

The Center for Creative Leadership has studied derailment since 1983 and names difficulty adapting to change as the most frequent cause. Its explanation is uncomfortable: many executives resist change because their past successes tell them they do not need to, and they fear that changing might lead to failure. That is the temptation described from the outside.

From the inside, it rarely feels like resistance. It feels like focus. A pattern I see often looks like this. Imagine a CEO who has just closed the best year in the company’s history. In the next strategy session runs an hour shorter than planned, because “we know what works”. The one director who asks about the second column of the audit gets a polite answer and no follow-up. The new market that would have made the team beginners again is deferred to next year. Nobody has made a bad decision. They have simply stopped making new ones.

The tells are small and specific:

• Strategy meetings get shorter after a good quarter, not longer.
• The phrase “we already know this” closes a discussion more than once a week.
• The person who raised a doubt last month has not raised one since.
• Next year’s plan is this year’s plan with larger numbers.
• You can explain what you did, but not why it worked.

None of these needs a villain. They need a win and no sensor.

Arguments

The case for

The evidence that success switches off learning is not a single study. Gino and Pisano found the pattern in racing, entertainment, pharmaceuticals and software, in the field and in the laboratory. In one of their experiments, people who succeeded at a first problem spent significantly less time reflecting on their strategy and were more likely to fail the second. Collins found the same pattern at company level, in institutions that were sick on the inside while still looking strong on the outside. CCL found it at career level, in executives whose past success made them resist the change that would have saved them. Three different lenses, one mechanism: the win removes the question.

The practical case is cost. Guardrails installed after a win cost a meeting, a role and a column on a dashboard. Guardrails installed after a miss arrive as a restructuring.

The case against

The strongest objection is that this is how coaches create work. The numbers are good, the team is tired and the last thing they need is someone interrogating their success. There is truth in it. A leadership team that has just delivered a hard year can read a post-win audit as ingratitude, and a leader who never lets a win land will drain the energy that produced it.

There is a second objection. Confidence is a real asset. Teams follow leaders who believe in the plan, and endless questioning can slow a company that needs to press home an advantage. Sometimes the formula really does work, and the correct move is to run it harder before competitors copy it.

Both objections hold in specific conditions. In a genuine turnaround, after months of strain, the priority is recovery and a short list, not an audit. And when a window is closing, speed beats reflection, provided you schedule the reflection for when the window shuts.

Where I stand

I do not ask leaders to celebrate less. I ask them to sequence it: celebrate first, then examine within a fortnight, then decide what to scale. In my 7-step coaching process, this sits across three steps. Awareness is where the post-win audit lives, because it replaces the story you tell about the win with evidence about it. Improvement is where rotating dissent becomes a habit rather than a gesture. Impact is where reverse indicators join the dashboard, so the board sees the cross-examination alongside the headline.

If the formula really does work, the audit will say so, and you will run it harder with better reasons. If it does not, you will find out while you still have credit. Either way, you leave the win understanding it.

Try this

Run a forty-five-minute post-win audit on your most recent success, inside the next fortnight.

1. Choose the win. Pick the result you are most proud of from the last six months.
2. Ask the four after-action questions in order: what we set out to do, what actually happened, why it happened, what we will do next time.
3. List every contributing factor on a whiteboard. Mark each one “ours” or “given to us”.
4. Rotate the challenge. Ask the most junior person in the room to run a premortem on next year’s version of the same plan.
5. Add one reverse indicator to the board pack, beside the headline number the win produced.
6. Write down one thing you will stop doing because of what you learned, and tell the team.

Then answer these on your own:

• What did I stop questioning after the last real win?
• Which part of last year’s result would I be embarrassed to learn was luck?
• Who in my team has stopped bringing me doubts, and when did that start?
• What key card did success hand me that I should give back?
• Which beginner’s bet have I deferred because it would make me look average again?

Where to go next

Temptation is the first stage of a sequence. Left alone, it hardens into a pattern other people pay for, which I cover in fatal flaws of leaders, and eventually into a culture that copies it, the subject of leadership pitfalls. If the temptation you recognise is mostly about what you cannot see, common leadership blind spots is the closer read.

The racing parallel is not decoration for me. Sport keeps an honest scoreboard, and it punishes a team that stops reading its own data. I write about that in from elite sport to the boardroom and in what elite sport taught me about boardroom performance. If you would like a room that is allowed to examine your last win with you, executive coaching is where that work happens, and you can book a 30-minute strategy call when you are ready.