High-performance leaders realize that more often than not they just don’t know how their people really feel about their leadership. Pushback, having the courage to question a leader and point out that his or her behaviour is counterproductive, can help a leader make a better, truly informed decision. The wise and mature leader will welcome the push-back: And it will make his or her job easier.

The most important book on leadership was written in 1837, by Hans Christian Andersen. It’s called The Emperor’s New Clothes, and if you’re not familiar with the story, here’s a summary. Two scoundrels pay a visit to an emperor. The emperor is famous for his vanity, particularly as far as clothing is concerned.

So the scoundrels pose as tailors, and tell the emperor that they have a marvellous new cloth, which is so finely wrought that only those of royal pedigree can see it at all. They suggest that they make a suit of clothes for him to wear in the upcoming parade.

The emperor, worried that he can’t see the cloth at all, asks his courtiers for guidance, and they, not wishing to seem ill-bred, unanimously agree that it is very fine cloth indeed. The suit is made – the two tailors make a great show of working night and day with looms, thread and needles which no one else can see-and the emperor dons his new clothes to take his place at the head of the parade. He strides out proudly in front of the assembled crowds, and they too, assuming that an emperor would do only what is proper, acclaim his outfit, while keeping their doubts to themselves, and wishing that they could see the cloth.

It is only when a small child cries, “Why, is the emperor naked,” that the people, the courtiers and the emperor realize that they’ve been deceived, by which time the scoundrels are far away.

It’s a deliberately exaggerated story, but it goes directly to the essence of many flawed human interactions. We’re often so intimidated by the power of others and the pressure to conform to the opinions of our peers that we ignore or suppress what our own senses are telling us. And if enough people fall into that trap sooner or later – well, if the leader isn’t exactly striding naked down the high street, he’s likely facing a fractious team, a disgruntled workforce or unhappy customers. Or, much worse, he or she faces an angry board, an SEC enquiry or shareholder lawsuits which, all in all, might make a stroll in the buff seem the more appealing option.

Yet all too frequently, many organizations don’t function the way they should when bosses aren’t challenged. Sherron Watkins believed so much in Enron and its leadership that she put her job on the line by telling chairman Ken Lay that she suspected Jeff Skilling and Andrew Fastow were engaged in corrupt activities. If Douglas Faneuil had stood up to his boss, Peter Bacanovic, at Merrill Lynch, about the mishandling of Martha Stewart’s sale of ImClone shares, the world might have been spared several sentencings, wasted tax dollars and many a tabloid headline. And certainly the scandal of sexual abuse in the Catholic Church in Boston demonstrated a dysfunctional organization, whether it came from “poor record-keeping” as Cardinal Bernard Law suggested, or a massive failure of leadership by the Cardinal, as others believe.

We can only assume that there are plenty of other organizations where unethical behaviour either goes unpunished or falls just short of being illegal. While the examples here are calamitous, I suspect that most organizations stop working the way they should long before a calamity occurs. These are the organizations where the right people don’t get promoted, where intramural conflict simmers endlessly, and where the best decisions don’t get made.

The leader in you

So, if you don’t want to be a victim of a bad boss – or of an otherwise good boss who is kept woefully in the dark – you must preserve your self-esteem and integrity by knowing how to push back, by knowing how to tell the Emperor that he or she is wearing no clothes. A key point here is that the emperor in the fairy tale, like so many bosses today, didn’t realize his predicament until someone else told him about it. More often than you might assume, bosses are in the dark about how their people really feel about their leadership or their agenda, their priorities, or about key decisions (which is why the really wise bosses solicit feedback from their subordinates). As the Hans Christian Andersen tale so delightfully illustrates, it’s scary to tell a superior that you don’t agree with him, that his priorities may be askew, that her actions are ill-timed or that her behaviour is inappropriate. It’s so much safer to tell the boss (the person with more power than you – the power, moreover, that could affect your career) that you agree. After all, you reason (as did the emperor’s subjects in the tale), the boss probably knows more about what is going on, so any intervention would make me seem stupid. If everyone else is in agreement, I must be wrong in some way. Better to sit tight and try to figure out why later on.

But if every subordinate thinks like this, who’s going to tell an emperor that he or she is naked? As a leader, you are. If you don’t, you’ll lose your self-respect. Or go home every night and kick your cat. Or yell at your kids. Or argue with your spouse or partner. Their boss, meanwhile, is in the dark about what’s wrong, and doesn’t have the information he or she needs to make a better decision. It’s a lose-lose proposition.

The hardest concept to get people to buy into is that, as a leader, they’re obligated to tell bosses when they’re naked. Not allowed-to-tell-if-the-moment-is-right, not supposed-to-tell-unless-other-circumstances-intervene, not permitted-to-tell-if-the-boss-is-open-to-it, but obligated-to-tell-however-painful-it-might-be. To be able to do so, however, you need to set the ground rules early and re-establish them often. With every boss, quite early in the relationship, you must let him or her know that you intend to demonstrate intellectual integrity. The key here is to do it artfully and sensitively.

The art of push-back

Most bosses like the power and authority they’ve worked hard to acquire. And with the success they’ve achieved, bosses can come to believe that their way is the right way, the best way-perhaps even the only way. It’s what led to their success, and it’s why bosses can easily mistake a contrary view from a subordinate as insubordination, rather than feedback To avoid this trap, leaders need to establish at the outset that they intend to tell their boss what he or she needs to hear, as opposed to what he or she wants to hear. It’s essential to tell a boss early in the relationship, before contentious issues arise, that you’re sure he or she wants an honest and straight point of view. Because contentious issues will arise, and when they do it’s too late to prepare a boss for push-back. Once you’ve set your boss’s expectations in this way, reiterate your position often, so that your boss understands that you equate intellectual honesty with loyalty, not with insubordination, that your motivation is professional commitment, not mutiny.

It was particularly crucial for me to follow this approach when I started working for our new division president – we’ll call him Dave. Everyone knew about Dave. He was one of the youngest division presidents – a superstar who had achieved sensational results in his past few assignments. Passionate, intense and strong-willed, Dave was held in high regard by his peers. But there were caution flags as well. He was known to be impatient, wanted most things done yesterday, and expected his people to do things his way. All in all, he was considered an intimidating boss.

I figured I’d better go slow with Dave and not throw my legendary “Tell it like it is” fastball for a few weeks.

After a couple of weeks, I saw Dave’s towering strengths first-hand – he was very bright, creative, decisive, and obsessive about winning in the marketplace. True to his reputation, however, Dave was all about push – he’d decide, without much consultation, what he wanted to accomplish and how the team should go about delivering it. And he had little patience for debate.

After a particularly bruising meeting in which Dave expressed his strong dissatisfaction with the implementation of some of his decisions, he brought the session to an abrupt close, and ordered that we reconvene the next day, after some members of the team took corrective measures to fix the problem. It was obvious that he was pretty angry. I figured it was now or never – this was the moment of truth.

As people began leaving the conference room and heading back to their offices, I approached Dave and asked if he had a minute to talk. He nodded, which I took to mean a reluctant “Yes.”

We entered his office, and his opening made it easier for me to do what I felt was needed. “What’d you think of the meeting?” he asked.

“Do you really want to know?”

“What’s that supposed to mean?”

“Dave, you and I haven’t worked together before, so I don’t mean to come across as a professional critic. But I figure you’re paying me to give you my best thinking on stuff. I mean-I think you want my honest opinion.”

“What are you trying to say, Mike?”

I swallowed but my mouth was dry. I wasn’t sure where this was going to end up.

“Dave, I owe you the truth in this job. And I think you want my points of view, even if they don’t agree with yours.”

“Keep going.” I had Dave’s attention, although he was clearly uncomfortable.

“You asked me what I thought about the meeting. So let me tell you, even though you may not like what I have to say. But like I said – I think you want me to be honest and give it to you straight. Not only about the meeting issue but on other stuff that comes up. For as long as I work for you. That’s the way I plan to operate with you.”

“Go ahead, I’m listening.”

So I proceeded to tell Dave that I thought chewing out individuals in a team meeting was a mistake, that it wasn’t the best way to elicit commitment from subordinates, and that his meetings appeared to be his, not the team’s.

He listened impassively, which I thought was unusual for such a quick-tempered personality. And then he said, “What do you think I should do now?”

“I’ve got a couple of ideas. First, apologize privately to Kate and Brian. I’d also set aside time at tomorrow’s meeting for all of us to build an agenda for next week’s meeting – and all our meetings. Probably most important, we should spend most of tomorrow’s session trying to figure out how this thing got screwed up. You know, try to sort out as a team what we did wrong so we don’t have the same implementation problem again.”

Dave listened carefully to this. “Anything else?” “No…just thanks for letting me tell you what was on my mind. Hope it was helpful.”

I got up to leave, but Dave had something else to say. “I heard you were independent. That’s your reputation, you know.”

“Yeah, I guess I am independent – but that has nothing to do with what I hope you see is my commitment to you and this organization. That’s exactly why you deserve my honest point of view for however long I work for you.” I left his office, breathing a very deep sigh of relief that my pushback hadn’t set him off. Dave subsequently took my advice. He apologized to Kate and Brian, refrained from chewing out people publicly, and was able to improve the quality of our team meetings.

Key language for effective push-back

In these situations, it’s crucial to set the terms and conditions as early as possible with your boss. You need to use phrases such as “I owe you the truth” or “I assume you’ll want my point of view, especially if it differs from yours” or “I may disagree but it’s because I’m concerned about our success and our performance.” (Saying “our success,” rather than “your success,” signals commitment and a sense of joint endeavour.) Rather than use phrases such as “I don’t agree…” or “I think you’re making a mistake…,” it’s generally better to begin with: “Another option we might want to consider…” or “Before we move forward maybe we should talk about…” or, “One of the things that concerns me about this approach is….”

If in doubt, ask questions that seek a broader understanding of your boss’s motivations and reasoning, rather than stating your concerns directly. Knowing how and when to push back may take some practice – and you have to really know your boss – but there should be no question in your boss’s mind as to your willingness to do it, and no doubt as to the reasons why.

And remember, we’re not talking here about situations where it’s difficult to figure out what you think is wrong. The point of the fairy tale is that no one had the courage to speak up, despite the fact that the emperor’s nakedness was obvious. Indeed, one of the flaws with the preoccupation with smart people is the assumption that intelligence is the single determinant of an employee’s value to an organization. But so many of the recent corporate downfalls seem to be much less a result of employees’ lack of brains (intelligence) than of their lack of smarts (wisdom). Intelligence is necessary if one is to be a high-performance leader, but it is not sufficient. The courage and the wisdom to know when and how to push back are what distinguish great people from merely good ones.

One final point from what I think is a very rich story: The emperor had no one to turn to for advice other than his subordinates. It’s lonely being a leader, and feedback tends to flow down the organization, not up, so the loneliness is accentuated if the leader has a poor indication of how he’s doing. High-performance leaders realize that more often than not they’re in the dark about how their people really feel about their leadership. If push-back is positioned so that it is questioning rather than challenging, and so that it encourages rather than curtails further debate (and thus generates more information on which the leader can base a decision), wise leaders will welcome it. It makes the job easier.

The essential point is that for the good of the boss, for the benefit of the business and, most importantly, for their own sense of self-worth, high-performance leaders have the courage to tell bosses when they’re naked.