It’s not some complex cloak-and-dagger scheme; it’s often just a few words in a talent review.

• “She’s doing a great job, but I don’t think she’s ready.”

• “He needs another year.”

• “We really can’t move anybody until we get through this quarter.”

Now, maybe those assessments are accurate. But they could also be code for, “This is my best employee, they’re the lifeblood of my department, and I’m not losing them.”

If you’ve ever wondered whether some of your leaders are keeping their best people out of the talent pool, there’s data to back up your suspicions.

A study examined personnel records and surveys at a large multinational manufacturer, including responses from more than 3,000 managers. Seventy-five percent of surveyed managers said talent hoarding occurred at least from time to time.^[i]

Imagine that one of your departments has a terrific employee, let’s call them Pat, who catches mistakes, handles difficult customers, keeps projects moving, etc. Basically, the department’s performance depends on Pat.

Now imagine that another department has an opening that could be a terrific next step for Pat. They’d be great at it, but their current manager knows that replacing them will be really painful, and nobody else has offered to help cover the work.

So when somebody asks whether Pat’s ready for that next step, the manager finds a reason to say, “Eh, not quite yet.”

That manager protected their department’s results in the short term, but a few floors away, the executive team is scratching their heads, wondering why the company doesn’t have stronger internal candidates and a deeper talent pool.

Now, here’s an interesting twist from the study. When managers learned they’d be moving to another team, and they had less motivation to hide their current employees, applications from their employees for internal jobs increased by nearly 80%.

In other words, employees were far more likely to pursue bigger and better opportunities when their manager’s incentive to hold on to them weakened.

That’s really what should bother CEOs. Even with an internal job board, a succession plan, and a nice statement about developing people, some of your strongest employees won’t (or won’t be allowed to) pursue new opportunities.

Here’s how you can correct this.

Read more

Jensen Huang, Nvidia’s founder and CEO, reads about a hundred emails from employees every day. Years ago, those emails alerted him to one of the greatest business opportunities this century: employees noted that researchers were using Nvidia’s gaming chips for machine learning. That tiny nugget of insight prompted him to focus Nvidia’s investments in the tools that would make it an AI powerhouse and the world’s most valuable company.^[1]

Most CEOs would never have gotten that insight because the people who had it were frontline employees; the folks actually down in the weeds seeing this market need firsthand. Executives and managers weren’t giving him that insight in their fancy presentations and meetings. Huang’s secret weapon was a simple email from employees called Top-5 Things, or T5T.

As CEO, almost nothing you hear is unfiltered or ‘free from spin.’ By the time a problem reaches you, it’s passed through layer-upon-layer of managers and executives trying to make it look “manageable” or spin it positively. And I guarantee that at least one of your employees has a brilliant, transformative idea that’s been watered down or pushed aside by some manager or executive.

The T5T email

At Nvidia, every employee, at every level, is asked to send a Top-5 Things (T5T) email with what they’re working on and what they’ve recently noticed in their market: customer complaints, competitor moves, technology shifts, and projects that look like they’re going to slip.

Here’s the specific format that Huang uses (and further down, I’ll give a couple of variations that you might find even easier to implement):

You’d been thinking about the idea for weeks, and someone who heard about it 3 minutes ago found the hole in it.

You weren’t careless; it’s just that nobody around you spotted (or mentioned) that flaw before the meeting.

AI can be an incredible tool for pressure testing your decisions, for poking holes in a plan before others get the chance. But that’s not what most executives experience, because, as you’ve probably noticed, AI has a butt-kissing problem. And you need a few prompts to make it stop.

Your AI Has a Butt-Kissing Problem

ChatGPT, Claude, Gemini, Copilot, (it doesn’t matter which one); they’re all trained to be helpful and agreeable.

Paste in your plan and ask “what do you think?” and you’ll usually get a nice summary of your own idea with a few compliments attached.

Ask it to find a study proving your pricing theory, and it may produce a convincing citation to a study that doesn’t exist. For a quick email draft, that’s annoying, but for a decision you’re taking to the board, it’s dangerous.

Make AI Argue With You

You can ask AI to challenge your idea repeatedly, from different angles, without worrying about making the conversation awkward.

Think about what happens when you ask a colleague to poke holes in your plan. They might raise a few concerns, but as the conversation continues, they may start wondering how much criticism you actually want. They’re sitting across from the CEO, listing the ways the CEO’s idea could fail, and they can see your face.

With AI, you can keep pushing. Have it examine the assumptions behind your plan, build the strongest case against it, or question it from the perspective of a skeptical director. Each approach gives you another opportunity to discover something you hadn’t considered. That’s what the four prompts below are designed to do.

The 4 Prompts for CEOs

I use some version of the following prompts with executive coaching clients before any high-stakes presentation. You paste your plan or your deck notes into whatever AI tool your company has approved for confidential material, then run these one at a time. Each one attacks your plan from a different angle.

Read more

In a new study published in the Quarterly Journal of Economics, the people who most wanted to be the manager didn’t just fail to beat managers chosen completely at random, their teams actually performed worse.

A team of economists brought 555 people into a lab and put them into three-person teams; one manager and two workers.

Before anyone got a role, everyone rated how much they wanted to be the manager on a 1 to 10 scale.

• In half the sessions, the job went to the people who wanted it most (almost half of them answered with a 10).

• In the other half, managers were drawn by lottery, including people who didn’t want the job at all.

Eager managers underperformed

First, teams led by managers who really wanted the job performed worse than teams led by managers chosen by random lottery.

How much worse? The researchers calculated that handing the job to the eager volunteers hurt team performance about as much as picking a manager with a dramatically lower IQ score (roughly the 16th percentile instead of the 50th).

Second, managers mattered a lot. The quality of the manager had roughly as much impact on team performance as the combined skills of the workers. In other words, a great manager boosted the team’s performance about as much as upgrading the skills of both workers.

Why did the eager managers struggle?

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That’s the conclusion of a study titled “Set Up for a Fall,” from researchers at the University of Michigan and Northwestern. Over six years, they tracked and surveyed 451 CEOs of companies with over $100 million in sales. They also surveyed more than 3,000 of the executives and board members those CEOs dealt with, and asked a pointed question: How often do you flatter this CEO?

The typical fellow executive or director admitted to complimenting the CEO’s strategic insight (in a slightly exaggerated way) about 3.6 times a year.

And about 3.3 times a year, they admitted to agreeing with the CEO on a strategic issue when they didn’t fully agree.

Those are per-person numbers. So if a CEO is regularly talking with two dozen peer executives and board members, the CEO is hearing an inflated compliment or a faked agreement more than once a week.

Here’s where this gets dangerous. The CEOs who received more flattery rated their own strategic judgment and leadership significantly higher than their peers rated them.

And then the researchers looked at what happened when these companies underperformed their competitors. CEOs who’d become overconfident from all the flattery were significantly less likely to change strategy. They didn’t shift spending on R&D or advertising, and they didn’t reshape the business portfolio. They just kept doing what they were doing because they were overconfident in their strategic judgment and leadership (from all the flattery).

Of course, not adjusting the strategy kept the company’s performance low. And low performance that persists while the CEO refuses to change direction is usually what pushes a board to remove its CEO. Among companies whose performance was already well below average, a CEO who received a modestly above-average amount of flattery was 64% more likely to be forced out (fired) over the following two years.

More Blind Spots

One of my studies at Leadership IQ hit this from a slightly different angle. We asked 1,204 employees to identify their boss’s blind spots, and the average boss had 3.6 blind spots. The most common blind spot, tied for first place at 48%, was overestimating their own performance or leadership ability. (Sound familiar?)

It gets worse at the top. Among C-suite leaders, 58% were seen as overestimating their performance, compared with 44% of leaders at other levels. And 45% of employees said no one feels safe being honest with their C-suite boss.

But this is probably the scariest finding: When we looked at bosses who’d been told about a blind spot, only 16% changed. And none of those 16% had the overestimation blind spot. Leaders who overestimate themselves don’t just fail to see the problem, they seem to lose the capacity to act on it even after someone points it out.

The Fix For CEOs

I can’t give all this bad news and not offer any kind of solution, so I’m going to provide two variations.

• First is the process I go through with my executive coaching clients.

• Second is a version you can run on yourself (or if you don’t have an executive coach).

In the flattery study, the CEOs most likely to change strategy when performance dropped were the ones who sought advice from people outside their circle of friends, and from people with different functional backgrounds than their own. And frankly, one of the most common reasons that CEOs come to me for executive coaching is just to get a source of truth from somebody who has no reason to flatter them.

Note: There are CEOs who ask me to interview their executives and board members to surface the unvarnished truth that they’re withholding from the CEO. But much of the time, the CEO has that truth locked away in their brain, and they just need somebody to dig it out.

The Executive Coaching Version

To move past the flattery-induced overconfidence and fully activate a CEO’s critical self-awareness, we have to do three things.

The first is attribution. Flattered CEOs blamed the market or their managers’ execution for poor performance and never the strategy. So one of the first things I do is walk a CEO through the last several times the company missed its numbers (or fell short on a goal, etc.), and for each one I ask: What did you tell the board (or your executives) caused that? Then: What would a skeptical outside investor say caused it?

When those explanations are laid out clearly, two patterns often emerge: Execution blame, which sounds like “The sales team isn’t selling it right.” And temporal deflection, which sounds like “It’s too early to tell. Give it another quarter.”

When every bit of underperformance falls on somebody else, that’s a pretty clear pattern, and most CEOs see it when it’s laid out this clearly.

The second is consensus. Flattered CEOs overestimated how widely their peers shared the good opinion of them, partly because they’d heard the same compliment from so many people. So I ask: Who was the last person to change your mind about something strategic, and when was that? If the answer is a name from three years ago, the CEO isn’t hearing disagreement anymore.

The third is testability. I ask: What would it take to prove your strategy wrong? Not “could it be wrong,” which every CEO will politely concede. I want at least three specific signals in plain terms: a win rate below a specific number, or a customer segment that stops renewing. If you can’t name what would change your mind, you’re already locked into a dangerously overconfident mindset.

The DIY Version

You can do a version of this by yourself, but because humans aren’t known for an abundance of critical self-awareness, you have to build in some protections.

Do the attribution audit in writing. List the last five times the company underperformed expectations. Next to each, write the cause you gave at the time, in one of four columns: market, execution, strategy, or something else. Now look at the strategy column. If it’s empty, either your strategy has been right through five consecutive misses or you’re not being critical enough of your strategy.

Invite disagreement by name. In your next three strategic meetings, pick the person who knows the relevant data the best and ask them directly for the strongest case against your position. Not “any concerns?” but “Sarah, you know the customer numbers better than anyone here. What’s the best argument that we’re wrong?” Then keep a simple tally: how many times in a month does someone actually push back on a strategic view of yours? If the number stays near zero even after you’ve asked by name, that’s usually evidence that you’re being flattered.

Write down what would prove you wrong. State your current strategy in one sentence specific enough to be false. Then write at least three signals that would tell you that assumption no longer holds, and a performance threshold that would trigger a formal strategy review. And give a copy to someone else. Do this while things are going well, because we’re a lot more likely to just double down when the going gets tough.

One last thing. My blind spot research found that leaders who overestimate themselves almost never change on their own, and the flattery study found that CEOs can’t detect the flattery aimed at them. It’s an unfortunate side effect of holding a position of power. It’s also why the CEOs who handle this well almost always have at least one person in their life whose only job is to ask them questions nobody else will.

“I don’t want to directly accuse my executive team of holding back and not telling me the truth, but I’ve got a sneaking suspicion that we’ve got some groupthink happening here.”

That ‘sneaking suspicion’ is how groupthink manifests; it’s rarely a giant red flag announcing that your executive team is about to make a terrible decision. It’s a subtle series of one executive softening a serious objection, while another shuts down because somebody told them they’re being too negative. Bit by bit, dissenting voices are silenced, and you’ve got what looks like ‘agreement’ (on a decision that at least a few people know is bad).

So here’s what I did with this executive team.

Analyze the transcripts

They had been using an AI notetaker for their meetings, so we had lots of transcripts. The first thing I wanted to analyze was what happened after someone raised a concern. Were objections fully discussed and analyzed? Or were they dismissed and shunted aside?

You can examine your own meetings the same way. Paste a speaker-labeled transcript into an AI tool approved for confidential company material and use this prompt:

An AI prompt to examine your meeting transcript

Review this executive team meeting for observable signs that 
useful disagreement was cut short.

Decision being discussed: [decision and context]
CEO or meeting chair: [name]
Transcript: [paste transcript with speaker labels]

Find up to five exchanges worth reviewing. 
Look for concerns or alternatives that were dismissed, ignored, or left unexplored, 
and changes in expressed views after the CEO or another senior executive spoke.

For each exchange, quote the concern and the immediate response, 
identify the speakers, and give the timestamp if available. 
Otherwise, number the transcript paragraphs and cite those numbers.

Explain whether the response addressed the substance of the concern. 
Describe the person’s subsequent participation, including whether they 
returned to the objection. 
Note plausible alternative explanations for the pattern you identify.

Present your findings in a table: 
quoted exchange and location; possible issue and alternative explanation; 
exact words the chair could have used to examine the concern.

Use only evidence in the transcript. 
Don’t infer private beliefs or treat silence as proof of groupthink. 
Don’t estimate speaking time from untimed text. 
If the evidence is weak or no clear examples appear, say so.

Also identify one exchange where disagreement was handled constructively, if present. 
Finish with one specific change to test in the next meeting.

Read the flagged exchanges yourself. A quiet executive might have nothing more to add, so you want to look for a recurring pattern in how the team handles disagreement.

What the transcripts revealed

This executive team had been discussing a significant investment into a new market. The sentiment was generally positive, but the CMO worried about brand and customer reactions, while the head of R&D raised concerns about technical feasibility.

After a concern was shared or an objection raised, the other executives would say things like

“I think you’re being too pessimistic,”

“That’s not really a major issue,”

“Let’s focus on the positives,”

“We can’t let perfect be the enemy of good.”

Those polite responses were enough to send a message: conform, get in line, we don’t want to hear your concerns. Following each response, the CMO and R&D head would then say very little for the rest of the meeting.

NOTE: This phenomenon is frighteningly common. In one of my studies, with 1,089 senior executives, only 14% strongly agreed that their team was comfortable disagreeing with each other. You can see where your own team stands with my 15-question Executive Team Health Survey, which includes instructions for running it anonymously and benchmarks to compare your results.

Groupthink takes hold when the desire for harmony in a decision-making group overrides a realistic appraisal of alternatives. For a CEO, that can mean making a decision without hearing the concerns of the very executives who will have to make it work. Or even worse, you end up making a terrible decision.

Even if your team is awesome, the pressure to conform is so insidious that it can happen unconsciously. With this executive team, we changed how people prepared for meetings and how their ideas were heard. Here’s how you can apply the same approach.

Stop groupthink before it starts

Analyzing transcripts gives you a great post hoc analysis, but it’s even better to stop groupthink before it starts.

A day or two before your executive team meeting, send this note. You want each executive’s thinking on paper before they’ve heard which way everyone else is leaning.

The one-page limit helps keep this from becoming a speechmaking contest or a test of endurance. If you don’t have time to send instructions days before the meeting, give everyone a few minutes to think and write before the discussion begins.

Researchers from INSEAD and the Wharton School discovered that instead of the classic brainstorming approach, where everyone gets together and throws out their ideas spur-of-the-moment, thinking independently before the group convenes delivers significantly better results.

Teams where people thought independently for a measly ten minutes before convening as a group generated about three times more ideas than those that only brainstormed as a group. And the ideas from the group that thought independently first were rated as having more business value and more likely to be purchased by customers.

The difference in the quality of their ideas was so large that an average idea generated from the independent thinking approach could rank thirty places higher in a list of one hundred ideas when compared to an idea generated from traditional brainstorming. A paltry ten minutes of thinking independently could be the difference between having a good idea and having a great, potentially game-changing idea.

Bottom line: Give people time to formulate a view before hearing everyone else’s. Quieter executives get a chance to prepare, and you have a record of what each person thought before the group started influencing them.

Give their objections a proper hearing

When your team gathers, give each person a minute or two to share what they’ve written before the discussion begins. If you’ve previously seen your team struggle to share their unvarnished thoughts, collect their responses and read them aloud yourself. You control the order and the attention paid to each person’s input.

In the case of this tech CEO, that’s what he did. In some particularly crucial meetings, he read aloud everyone’s written responses himself. The team also reordered its discussions, intentionally bringing dissenting voices to the forefront. [NOTE: If you’re a subscriber and want help applying any of these tools with your executive team, feel free to reach out to me at mark@leadershipiq.com].

When someone responds to a concern with “Let’s focus on the positives,” use this sequence to give the objection a proper hearing:

“Before we move on, let’s understand the concern. [Name], what specifically are you worried could happen, and what are you basing that on?”

“What evidence do we have that addresses this concern? What would we need to check?”

“Given what we’ve heard, should we change the plan, investigate further, or proceed while accepting this risk?”

Record the concern and the decision. If it needs investigation, name an owner and a deadline for bringing an answer back.

You can decide to proceed despite an objection. The executive raising it should be able to see that the team examined it and explain why the decision went the way it did.

Check whether the next meeting changes

Once you’ve changed how you prepare and run the meetings, examine the next few transcripts. Use that AI prompt from earlier and check whether objections are being explored and the people raising them continue contributing. Reviewing subsequent transcripts will help monitor your progress and spot any backsliding into old patterns.

Before you close your next executive team discussion, make sure the objections have been examined. If a concern disappears from the conversation, you should be able to explain what resolved it.

• The executive team made a decision, and you’re not sure everyone’s going to support it once they’re back in their departments.

• In your meetings, you can tell not everybody agrees, but nobody’s saying so out loud.

• Two of your executives can’t work together without you in the room.

• You’ve gotten surprised by bad news that one or more of your executives clearly knew earlier than you.

What those have in common is that you can’t fix them by asking people individually. If you ask your CFO whether the team has hidden agendas, you’ll get the answer people give their boss, which is that things are mostly fine and could be tightened up a bit. Nobody who reports to you is going to say that the team you built has a problem, and they’re especially not going to say it in front of the other people on it.

So the only way to learn what your executives actually think of the team is to let them say it without their name attached.

This post gives you the 15-question Executive Team Health Survey, with instructions for running it anonymously on your own team, and the comparison scores from 1,089 senior executives who’ve already taken it.

When your results come back, you’ll know four things you can’t know today.

1. Whether the issue is one executive or the whole team.

2. Whether your executive team’s challenge is accountability, candor, commitment, learning from its own mistakes, or just the meetings themselves.

3. Which of the fifteen questions to fix first.

4. And how far your own view of the team is from the team’s view of itself, which is usually the number CEOs least expect and most need.

Let’s dig into each of the 15 questions, what they mean, and how to conduct this survey with your own executive team.

But there’s a problem when CEOs interview candidates. And it’s a strange one, because it’s not a CEO weakness that causes trouble, it’s actually an overwhelming CEO strength.

The research on CEO personalities consistently shows that they’re assertive, verbally adroit, and most importantly, relentlessly achievement-oriented. You’ll rarely hear a CEO tell someone, “It’s totally fine that you didn’t pull it off, just try better next time.” CEOs don’t just dislike failure, they hate it. And they push everyone around them to overcome it.

You Need To Let Candidates Fail

The attitudes that sink a new hire are exactly the ones you miss when you don’t let a candidate fail. The Hiring For Attitude research on more than 20,000 hires found that 89% of hiring failures are attitudinal, not skills-based (attitudes include characteristics like coachability, motivation, and temperament). Those are the traits a candidate only reveals when you leave them room to give a real answer, including a bad one.

Watch how it goes wrong. The CEO asks, “Could you tell me about a time you made a mistake at work?” The candidate says something like, “Yeah, I missed a big deadline on a client project last year. I underestimated how long the build would take, and it slipped.” Then the candidate stops talking.

To the CEO, that unfinished answer is intolerable. So they jump in. “Well, what did you do about it?” Or, “How did you recover?” Or, “What was your next step?” In the CEO’s mind it’s almost unthinkable that a person would make a mistake and just sit there, not immediately moving to correct it, learn from it, and turn it into some burst of transformational growth.

But the candidate already told you they don’t think like that. They made a mistake, they accepted the mistake, and maybe they’ve quietly accepted that they’ll make others like it. It’s not the ideal answer. But it’s the true answer, and it’s exactly the answer you needed to hear.

The Five Words That Ruin Interview Questions

This doesn’t only happen live, in the moment. A lot of the time the answer is already baked into the question, waiting there before the candidate opens their mouth. Here’s a common one:

“Could you tell me about a time you lacked the skills to complete an assignment, and how you overcame that?”

The last five words, “and how you overcame that,” hand the candidate the answer to the question. You’ve just told the candidate you want initiative, learning, and a problem that got solved, so that’s the story they’ll build, whether it’s true or not.

Imagine a candidate who has lacked the skills to complete an assignment 100 times. In 99 of those times they waited around for help, blamed the assignment, or turned in weak work. And then one time they actually figured it out. Those five words tacked on to the end of the interview question, (”and how did you solve it”), instruct the candidate to bury the 99 failed examples and tell you about the one rare success. You end up interviewing the best five seconds of someone’s career and calling it a pattern.

The fix is almost insultingly small.

That’s one of the findings from the study “CEO Stress, Aging, and Death.” Originally circulated as an NBER working paper and later published in The Journal of Finance, the study’s mortality analysis includes 1,900 chief executives of large U.S. companies.

CEOs have stressful jobs, but this analysis reveals disturbing truths about the effects of those pressures on mortality and aging. (By comparing wealthy CEOs facing different working conditions, the researchers were able to separate the effects of job pressure from financial hardship.) Even among executives unlikely to struggle to pay the bills, the health costs of stress were substantial.

About 40% of the CEOs studied experienced industry-wide distress. The researchers defined distress using a decline of at least 30% in the median company’s stock price over two years. The Great Recession, for example, exposed lots of industries to this kind of pressure. And obviously, plenty of industries are facing similar pressures right now.

Looking at industry-wide declines helped the researchers study pressure that extends beyond the decisions of an individual CEO. You can be doing a lot of things right and still find yourself running a company in an industry that’s suffering.

Then, using machine learning, specifically convolutional neural networks, the study analyzed more than 3,000 pictures of CEOs taken before and after the Great Recession. The software estimated apparent age: how old someone looks.

Taken together, these findings should make it harder to wave away prolonged stress as something that simply comes with the job. The costs can show up in a person’s face and in their life expectancy.

It’s tempting to assume that CEOs are especially well equipped to handle stress. After all, people who aspire to the top spot have chosen a career track with long hours and consequential decisions. But choosing that career doesn’t establish how much stress someone can withstand.

Here’s how I turn that question into a practical exercise with executive teams.

1. Have each executive take two minutes to write down specific pressures they personally experience in their role, including priorities that keep changing and decisions that remain unresolved while they work around them.

2. Compare the lists and identify which pressures the executive team’s own decisions or habits are creating.

3. Pick one you can reduce in the next 30 days.

4. Agree on exactly what will change and who’s responsible for making it happen.

5. At the next meeting, ask the affected executives whether that change actually reduced the pressure.

Their answers will tell you whether you solved the problem or simply had a good discussion about it.

The study doesn’t tell us how many years any particular management change might add to someone’s life. But it does give us a compelling reason to examine the pressures we’ve come to accept. Before you and your executive team take another stressful quarter as proof that you can handle anything, identify which pressures you could stop creating for yourselves.

Thousands of leaders and professionals have taken the free online test “How Do You Personally Feel About Change?” One of the questions asks respondents to select from these options:

• I undertake career/business changes that others describe as difficult or audacious.

• I undertake career/business changes that are achievable and realistic.

• I don’t undertake very many career/business changes.

If you’ve ever struggled to convince people to start a really big change, you won’t be surprised to learn that less than a third of respondents undertake changes that are difficult or audacious. Generally people either avoid change or they undertake changes that seem more achievable. All the clichés about change being hard and people avoiding change are pretty accurate.

But while this is true overall, I discovered big differences in how people view change when I dissected the data by position. For instance, 45% of top executives undertake changes that others describe as difficult or audacious. But for frontline employees, that number is only 27%. So in the average company, the CEO is 66% more likely to want audacious change than the employees.

The following chart shows the data for all job levels:

You can see from the chart that there is a very strong linear relationship between how high a person ranks in the company and how much they undertake audacious change.

Frontline employees and junior managers are more likely to enjoy the traditional status quo, and if they do embrace change, it’s more likely to be cautious and measured.

By contrast, CEOs are much more likely to be the change advocates I call Venturers. Venturers are motivated by risk, change, and uncertainty. They thrive when the environment or the work is constantly changing. They tend to like challenges and jump at the opportunity to be the first to do something new. And that means they’re also not terrified of failure, especially if they know they’ll find a chance to try again.

Venturers prefer adventure to security. In fact, they find doing the same thing every day incredibly boring. They like to break through their comfort zones, so they regularly challenge themselves with audacious and difficult challenges.

Venturers have some very distinct personality characteristics. And it’s no small coincidence that these characteristics are found more often in CEO roles than in frontline employees or junior managers. In fact, we might surmise from this data that perhaps one way to increase your odds of becoming CEO is to undertake more difficult and audacious change. It’s no guarantee of career success, of course. And obviously, if 45% of CEOS undertake big changes, that means 55% either embrace a more cautious change or avoid change altogether. But the linear relationship between one’s rung on the career ladder and audacious change is really striking.

It’s also a good measurement with which to evaluate your fellow CEOs. Do they undertake audacious and difficult change, or are they more cautious and circumspect?

Is undertaking audacious change an inborn personality characteristic? Is it learned? Or is it some combination of the two? The truth is, we don’t definitively know, but it’s a good bet that both nature and circumstance have a role to play.

It is true that some people are more predisposed to undertake significant change, climb higher mountains, and tolerate more risk. And this is generally observable in even very small children. On your local playground you’ve probably seen some kids who look like they’re ready for the X-Games while others seem intimidated by the monkey bars.

But it’s also true that CEOs are often under great pressure to undertake audacious change. Boards regularly compare their CEO to executives like the late Steve Jobs, who talked about making a dent in the universe, or other larger-than-life personalities. And if you’re the CEO being compared to Steve Jobs, you are going to feel pressure to undertake more audacious and difficult changes, just to have any hope of comparing favorably.

So what should you do with all this information? Start simply. Look at your current company. Are there lots of big changes or are things pretty status quo? Once you have a handle on your current environment, do an honest assessment of yourself. How would people describe your approach to change? And how does that assessment fit within your current environment?

Let’s assume, though, that you mean what you say about wanting independent thinkers running your departments. There’s still a hidden danger that undermines even the most talented management teams: groupthink. It leads to poor choices and missed opportunities, and in extreme cases, catastrophic failures.

Groupthink occurs when the desire for harmony or conformity in a group results in irrational or dysfunctional decision-making. Members of a group suppress their own opinions and adopt the opinion of the rest of the group, even when they privately disagree with the consensus. And for a CEO, the most expensive version of groupthink isn’t the kind that happens among frontline employees. It’s the kind that happens among the managers who decide what you get to hear.

Consider the cautionary tale of Nokia, once the world’s leading mobile phone manufacturer. Despite recognizing the need for a more advanced operating system to compete with Apple, Nokia’s managers hesitated to openly admit their current system’s shortcomings. In 2007, Nokia produced more than half the planet’s mobile phones and, by 2013, they were demolished by Apple, Google and Samsung. The managers’ reluctance to voice concerns led to a culture of obfuscation and contributed to the company’s downfall in the smartphone market.

In the words of one manager, “Why tell top managers about this? It won’t make things any better.” If you’re a CEO, read that quote twice. It’s a middle manager explaining why you were the last to know.

So it’s crucial to hire managers who can resist the pull of groupthink: leaders, whether formally titled or not, who are willing to speak up, challenge assumptions and bring a different perspective to the table. But how can you identify those people during the hiring process?

One effective strategy is to ask candidates the following question: “Could you tell me about a time your idea or opinion was rejected?”

This question reveals a great deal about a candidate’s ability to handle dissent, maintain their convictions and navigate a room that isn’t on their side. When you ask it, keep it simple and open-ended.

Resist the urge to tack on additional prompts or leading phrases. Interviewers routinely add qualifiers like “and how did it work out,” “and how you solved it,” or “and how you did so successfully.” While well-intentioned, these additions steer candidates toward more positive, resolution-focused answers. By keeping the question bare, you let candidates reveal their real approach to handling rejected ideas. And this matters twice as much when the CEO is the one asking, because a manager-level candidate sitting across from the CEO already wants to give you the tidy version.

Let’s examine two potential responses to this question, one that suggests a tendency toward conformity and another that indicates leadership potential.

A less desirable response might sound like this:

“In a leadership team meeting, I suggested a new approach to our marketing strategy, but the VP didn’t like it. I figured she probably knew better than me, so I dropped the idea and went along with what everyone else wanted.”

This answer suggests a candidate who’s prone to conformity and unlikely to persist in the face of opposition. They abandoned their idea the moment someone senior pushed back. Put that person in charge of a department and you’ll have a manager who agrees with you in every meeting, which is exactly the manager Nokia had.

In contrast, consider this more promising response:

“In a previous role, I proposed a significant change to how our customer service team was structured. Initially, my idea was met with skepticism from the rest of the leadership team. Instead of giving up, I took the time to gather data supporting my proposal. I then scheduled individual meetings with the people who had the biggest concerns to understand what they were worried about and refine the idea. My original proposal wasn’t implemented exactly as I’d envisioned, but those discussions led to a hybrid solution that incorporated elements of my idea and addressed the team’s concerns. The new structure ended up improving our customer satisfaction scores by 15%.”

This response demonstrates several qualities that help a manager resist groupthink:

1. Persistence: The candidate didn’t abandon their idea when faced with opposition.

2. Adaptability: They were willing to refine their proposal based on feedback.

3. Data-driven approach: They gathered evidence to support their position.

4. Collaboration: They engaged in individual discussions to address concerns and build support.

5. Outcome-focused: They stayed focused on the goal rather than being wedded to their original idea.

Hire managers who exhibit these qualities and you’re more likely to build a management team that resists groupthink and makes better decisions, including the decision to tell you something you don’t want to hear.

It’s important to note that hiring for these traits isn’t about creating conflict or disruption for its own sake. It’s about building a management layer where different perspectives are valued and critical thinking is expected. That means actively seeking out alternative viewpoints, encouraging your managers to voice concerns, and demonstrating that it’s safe to challenge the status quo, including when the status quo is your idea.

That last part is on you. A CEO plays the decisive role in whether dissent is welcomed or merely tolerated. It’s not enough to hire managers who can think independently; you have to keep that ability alive once they’re inside, and managers watch what happens to the first person who disagrees with the CEO far more closely than they listen to what the CEO says about openness. Model the behavior you want: show that you’ll change course when someone brings compelling evidence, and thank the manager who brought it, in front of the others.

So when you’re hiring managers, look beyond technical skills and experience. Seek out people who can think independently, persist in the face of opposition, and work with others to refine and improve an idea. Ask the question above and let the silence after it do its work.

The goal isn’t to hire contrarians who oppose every idea. It’s to hire managers who can think critically, express their views respectfully, and work constructively with others to reach the best outcome. Build a management team of leaders rather than followers, and the next time one of them sees what Nokia’s managers saw, they’ll tell you.