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Don’t Hesitate to Tell the Boss He or She Is Wrong

There’s nothing worse than not wanting to roll out of bed in the morning and head for work. Many people feel that way. Some let their friends know when they get there that they’d rather be anyplace else, doing anything else, for anyone else.

Instead of feeling like it’s a wonderful world, they feel downright blue about their place in life. Someone once said, “The biggest troublemaker you’ll probably have to deal with watches you from the mirror every morning.” That may be true, and if it is, you’re the only one who can fix it. New town, new company, new job, new boss? Any and all of those alternatives are possible. But maybe what you really need is a new start and a new attitude.

However, when it’s less about you than it is about your boss, that presents a different and more difficult problem. If the boss is here to stay, invest in determining what is wrong and how to fix it. That might require an attitude adjustment in terms of accepting the boss—right or wrong, good or bad—as the person who calls the shots.

Over the course of my professional life, I couldn’t wait to get to work, do my job, and do it well. Success at it was my reward, and I have found that success begets success. It can also be shared with others who work for you so that their mood and motivation match yours.

Along the way I hit a bump in the road. My old boss, whom I admired and respected, retired. My new boss, who was admired for what he had previously achieved professionally in his life, was totally out of his element. No experience in this newly assigned field yet put there because of his overall reputation up to that point.

It didn’t take long for a collision to occur on this particular road of life we were on together. He was very self-assured and outspoken in his views. It was in the third week or so of the morning staff meetings he chaired, and a dozen or so of his senior assistants attended. We were gathered in his Pentagon office when the confrontation occurred.

As the chief of media relations for the army, I apprised him of a press report critical of the army on a particular issue. “That’s the problem,” he barked. “The press reports things as they want to see them, not as they actually are.” Careful, I thought to myself; hold your tongue. The relationship with my new boss was young. No need to damage it at such an early stage or at all.

He went on to say, “If it hadn’t been for a critical press, we would have won the war in Vietnam.” As a Vietnam veteran aviator, he saw it from his point of view. As a Vietnam veteran infantryman, I saw it differently. We didn’t lose the war; we simply didn’t win it, not because of our tactical inadequacies or failures in the field but because of our strategic incompetence at the national level. He was wrong with the glittering generalities he put forward in a heated and pointed way. For a good part of that meeting and on subsequent occasions it was evident that he had a beef with the press.

Clearly he saw me as part of the problem. Since to his way of thinking I dealt each day with those dastardly reporters, I must be on the side of the enemy. At least I sensed he believed that.

There were numerous clashes when he and I simply did not agree. He had a slight advantage—he was a general, I was a colonel. I paid him his due respect, but I never hesitated to tell him when I thought he was wrong, always giving him the reasons for my point of view.

One might argue that when you are at odds with the boss, silence is sometimes the tactically best answer, and that may be so if you choose harmony over honesty. You are never going to move the needle, however, if you don’t express your opinion on things you feel strongly about or, better yet, you know to be true.

I parted company with my general and boss who hated the press a year or so later and went to a much better job working for a man far more understanding of the role of the press in a democratic society. Ironically, years later the general with whom I never saw eye to eye tracked me down telephonically. He had retired and had been asked to look for a candidate to work as public relations counsel for former President Ronald Reagan at his official office in California.

I thanked him for his interest in considering me but declined, telling him I had a job I enjoyed immensely. It did my heart good, however, to realize that despite our disagreements in days past, he felt confident enough in my skill set to offer it up to the president. Perhaps, just perhaps, my honesty was one of the qualities that passed his litmus test.

Not that any two circumstances or relationships with bosses are the same. But one thing is a constant: the openness and honesty you need to have with your boss when that person is not correct or is not using proper judgment.

If you tactfully explain to that person what is not right or needs to be done differently, he or she may well respect you and your opinion more than would be the case if you never offered it. No one likes to be told they are wrong, but if they’re smart, they’ll prefer that to making a mistake.