It Doesn’t Take a Wizard to Build a Better Boss

Like most people, I’ve spent my career working with the Scarecrow, the Cowardly Lion, and the Tin Man.

Welcome to the Land of Oz — and a career path that looks like the Yellow Brick Road. Dorothy’s adventure, it turns out, is the perfect metaphor for a world of work where almost everyone’s boss is either unintelligent, indecisive, or irascible. I know this from studying bosses in hundreds of companies — and from my own career. Based on my experience, all bad bosses fall into three groups: the boss with no brains; the boss with no courage; and the boss with no heart. In other words, like most people, I’ve spent my career working with the Scarecrow, the Cowardly Lion, and the Tin Man.


I started down this road in 1978 when I joined the Harvard Business School faculty. One of my first assignments was to teach MBA students about leadership. This seemed to me completely backward. After all, few of us ever achieve the exalted position of leader; all of us find ourselves at one time or another in the role of follower.

So for the past 18 years, I’ve made it my business to spend much of my time studying the accomplishments of the bossed rather than the boss. In the process, I’ve discovered some truths at the heart of the relationship between the boss and the bossed:

  • Everybody hates the boss. Maybe not all the time or every day — but at one time or another, everybody goes home from work, sits down to dinner, and complains bitterly about what’s wrong with the boss.
  • Everybody complains about the same things: The boss doesn’t listen. The boss doesn’t offer encouragement. The boss doesn’t recognize superior effort. Whatever the specific language, the theme is always the same: there’s something wrong with the boss.

Along with these universal truths, I’ve discovered a number of absolutely pragmatic — and surprisingly counterintuitive — conclusions:

  • You cannot change the boss. Everyone tries; it never works. Complaining about the boss won’t make the boss a better boss. It will make you a bitter employee.
  • You cannot simply adapt yourself to whatever the boss wants. This old-fashioned, 1950s “Company Man” view of the world is obsolete. The world moves too fast for sycophants.
  • Nor can you declare yourself empowered and become boss-free. Sorry. Hierarchy is here to stay; the boss is still the boss — and often for good reasons.

All of this suggests a hard fact of business life: there is no wizard who can build you a better boss. You, however, can build a better you. You can sharpen your skills, advance your career, develop your character — and do it by learning from your boss’s foibles and frailties. In other words, as unconventional as it may seem, with few exceptions, the worse you think the boss is, the better the opportunity is for you.


Ultimately The Wizard of Oz is about two things, the same two things much of work life is about: asking the right questions and taking the situation in hand. These are the keys to building a better you — whether or not you improve your boss.

“I won’t try to manage things, because I can’t think.” — The Scarecrow

I. The Scarecrow: The Boss Does the Talking, You Do the Thinking

How stupid was Steve DeSimone?


The year was 1970 and antagonism was high between college-aged Vietnam War protestors and middle-aged law-and-order cops. Steve drove a red GTO and the cops were constantly giving him tickets for seemingly minor infractions.

One day, I walked out with him into the parking lot. “Steve,” I told him. “I think I’ve figured out why the cops are after you.”

I pointed to his vanity license plate that read “SDS,” for Steve DeSimone — or Students for a Democratic Society, the antiwar student group.


DeSimone was my boss; he directed a state youth opportunities commission, a post he’d gotten for one reason: his dad ran a major union. I was his deputy. It was my second real job; I was all of 19. The work: design a first-of-its-kind statewide employment program for teenagers and get a federal grant to finance it.

On my first day at work, I discovered that Commissioner DeSimone would be around for only two days before taking two weeks off. So I went to him with a rookie question: “What do you want me to do?”

His answer: “Two things. First, get that grant. Second, get me good press.”


That was it. DeSimone might have been stupid, but at least his goals were clear. In that instant, I recognized that I had a choice. I could either decide to do nothing more, sit around and whine about my boss, or I could make him look good in exchange for designing and running the whole job program myself.

At the time, it struck me that making my dumb boss look smart was a very small price to pay for all the running room I was being given. Apparently my predecessor hadn’t seen it that way. He’d left the post in a funk.

My reaction was: Who’s the dumb one here? If your boss is a Scarecrow, his stupidity is your opportunity. So what do you do?


As much as you can. Take on as much work and as much responsibility as you can handle. Do the work. Then do the briefing necessary to keep the boss well-informed and comfortable. And most important, do whatever it takes to make sure the boss gets all the credit for all the work you do.

What do you not do? Don’t listen to your ego. Worrying about getting credit is the worst mistake you can make. If you’re doing all the work — going to the late-night sessions, developing the strategies, seeing them through to implementation — then others both in and out of the organization will have a clear understanding of your contribution. Those who matter will know that you’re the source of the ideas.

What do you get out of working for a Scarecrow? An opportunity you couldn’t possibly have with a smart, high-powered, mentor of a boss: the opportunity to immerse yourself in boss-like work years before you might otherwise have the chance.


What do you give up in a situation like this? Absolutely nothing.

But if Steve DeSimone’s willingness to let me do the thinking for him represents the best-case Scarecrow scenario, there is also a worst-case scenario: a stupid boss who wants to micro-manage the organization.

I have not only worked for this kind of boss, I was one. It was my first job after graduate school; I had been hired by a major manufacturer and sent to a Midwestern factory to learn the ropes, managing the night shift. When the time came to report for my first night after training, I was more than ready. I’d read the performance charts and knew I could boost productivity and do it literally overnight.


When my shift reported, I immediately began rallying the troops. I told them that I’d figured out how we could cut the amount of time it took to do an equipment change. I even jumped onto one of the forklifts to demonstrate my more efficient method. Mistake. Big mistake. Before I knew what had happened, the whole crew had walked off the factory floor and into the cafeteria. I had single-handedly triggered a wildcat strike.

At that point I did the only thing a young manager knows to do: I called home, woke up my wife, and asked her what to do. Her advice: apologize. So I went into the cafeteria and did as I’d been told. Peace was restored — and I’d learned an important lesson about the bosses and the bossed. If I tried to act “bossly” about things I knew nothing about, I could only screw things up. The routine work was under control. If I really wanted to be the boss, I needed to find ways to add value — otherwise, the best I could do was to get out of the way.

When the boss is both stupid and meddlesome — as I was — you have to find a way to teach him that lesson, politely but firmly.


“I haven’t got any courage at all. I can’t even scare myself … I’m afraid there’s no denying, I’m just a dandelion.” — The Cowardly Lion

II. The Cowardly Lion: Do You Have the Courage of Your Boss’s Convictions?

For years, I had a boss who refused to take a stand. He wouldn’t sort out the disagreements between battling subordinates. He routinely postponed decisions until they were made by default. In all those years, not once did he solve a professional problem I brought to him.

When he finally retired, I sat down to write him a letter, mostly to address my own frustrations. When I finished, I had written one long thank-you. What I realized was that at a half-dozen critical points in my career, my boss’s refusal to act had forced me to act on my own behalf. And each of those points had turned out to be essential to my personal growth.


I learned from him that the boss who lacks courage — like the boss with no brain — can be a valuable person to work for.

Start by trying to understand what makes the Lion quiver. In other words, when you complain that your boss lacks courage, what exactly does that mean? Is the boss slow to act? Too timid?

Perhaps what the boss lacks is information, not guts. There isn’t a subordinate who hasn’t made a proposal to the boss, only to be told to find more data to support the recommendation. And there isn’t a subordinate who doesn’t consider such a request to be a sign of executive gutlessness and bureaucratic indecision. But to the boss, information is courage. The subordinate’s job is to supply the passion. The boss’s job is to make sure that the data supports the passion. That’s not cowardice; it’s competence.


Or maybe the boss simply has a different view of the world. The next time you think the boss is ducking an issue, step back and reframe the problem. Ask yourself what the boss’s perspective brings into the picture that you don’t see. Does the boss work on a larger canvas, introducing departments, competitors, or issues that your view excludes? Or are you framing the issue in the wrong way when you present it to the boss?

If you’ve run yourself through those questions and the boss still comes up gutless — well, there are, of course, bosses who genuinely lack courage, bosses who’ve gotten to where they are by avoiding mistakes, by avoiding decisions. Those are the bosses who make every decision a gut check — for you.

When the boss is a coward, you have to ask yourself tough questions. You have to decide when something is important enough for you to take it on. You have to decide what battles are worth fighting. You have to decide how much courage you have — and in the process, measure your own bravery.

Dealing with the Cowardly Lion means you have to stop whining. Make your decision, then try to get the resources and support you need to move ahead — remembering that it’s always easier to ask forgiveness than permission.

As you become more of a self-starter, you’ll learn that working for a Cowardly Lion can be more rewarding and fulfilling than working for a Lion King. You learn how to calibrate the risks you take; how to measure what it takes to get things done; how to scramble when an effort falls flat; even how to value caution. And most important for your own growth, you find out where your convictions and your comfort zone intersect.

“Just to register emotion…if I only had a heart.” — The Tin Man

III. The Tin Man: The Boss Carries an Ax

Bosses often have to be demanding, brusque, impatient. Bosses have to set high standards, make tough decisions, push the organization. But when you’re on the receiving end of a blast from the boss, “tough-minded leadership” feels more like insensitivity and brutality. As unpleasant as it can be, working for a Tin Man often turns out to be one of the most beneficial learning experiences — if you can figure out how to avoid the ax.

Working for a boss who’s tough on purpose can teach you lessons you’d never learn any other way. People who’ve worked for a Tin Man often find themselves saying, “He took us places I never thought we could go.”

A Tin Man also teaches the value of mental toughness. When you work for a Tin Man, you learn the mental discipline that competition demands — and you come away from the experience with higher performance standards and expectations for yourself and those around you. Finally, working for a Tin Man is an introduction to the passion of business. While a Tin Man may not always have a heart for the people around him, he almost always has an inextinguishable commitment to the business.

I saw this in the middle of my career, when a new boss took over as a change agent for our smugly satisfied organization. Without recognizing it, we’d allowed our success to make us complacent. His job was to wipe out the complacency and recharge the organization’s sense of purpose — and that took direct confrontation.

In his first week, he marched into a meeting brandishing a memo written by one of our senior team members. There wasn’t a line on the page that hadn’t been marked up — it looked like a red pen had leaked all over it. He spent the first 30 minutes of the meeting destroying the memo — the ideas were useless, the recommendations were laughable. Then he marched out of the room.

We sat in stunned silence. None of us had ever witnessed such a blistering attack. When we could talk, we all agreed: the boss was a jerk; he was out of line. Privately, we all knew that the old days were over; we’d have to change or leave. There was a new sheriff in town — and he was wearing a tin badge where his heart should have been.

Watching this Tin Man at work taught me the difference between a boss who’s tough on purpose and a boss who’s just tough on people. The first difference is motivation. As events unfolded, it became clear that he wasn’t just playing head games. He was using every edge and angle he could in order to break through our complacency. Nothing was too trivial to make the point — not even the shortest in-house memo.

The second difference was the target of his criticism. He didn’t whip people — but he did flay their work. The distinction is critical: everybody’s work was open to criticism and in need of improvement. He didn’t play favorites; nobody was immune and nobody was a scapegoat.

The third difference was the way he modulated the criticism. He believed in a work-hard, play-hard ethic. We learned to argue and fight for what we believed in, then put the disagreements behind us and move on — together. Gradually we shifted from thinking the boss was a jerk to seeing the method in his madness. And gradually he toned down the volume and frequency of his attacks.

When the boss is a Tin Man with a purpose, there are ways to survive and even thrive. For example, if the boss doesn’t acknowledge the emotional consequences of his behavior, then you have to keep emotion out of your side as well. The criticisms aren’t personal, so don’t take them personally. Focus on the content, not the style.

Sometimes you can’t get the boss to listen. Try examining what you’re doing to get the boss’s attention. Does the boss respond better in the morning? In a team meeting or one-on-one? Are there people the boss does listen to — and what can you learn from them? Are you presenting ideas to the boss in the best form? Do you even know how the boss likes to get information — memos, e-mail, phone mail, in person?

If the boss is simply a hardass, then develop a support system elsewhere: colleagues who appreciate what you do for them, subordinates who recognize your willingness to do battle on their behalf. Although we all prefer to work for bosses who have some interpersonal skills and sensitivity, the hard truth is that it isn’t the boss’s job to make you feel good. If you do work for a Tin Man, however, you’ll often come away with an appreciation for the importance of heart — and with much stronger skills.

“Here, Here! What’s all this jabberwock when there’s work to be done?” — Auntie Em

IV. Building a Better Boss: The Wizard Is You

Bosses are just people. When you confront one you don’t like — whether Scarecrow, Cowardly Lion, or Tin Man — take a step back, ask yourself what the problem really is, see if there isn’t a hint of opportunity lurking within the boss’s glaring inadequacy.

Make sure you don’t become the kind of boss you’re angry about having. It’s easy to let your boss’s attitude infect your own. Remember what you don’t like about the boss — then take pains not to become your enemy.

Be realistic. The best strategy for dealing with a really insufferable boss can be to plan your exit. Determining that you’ll be gone from your job in one year can be liberating: it can release a lot of built-up emotional pressure, change your day-to-day attitude, and sometimes even allow you the perspective you need to solve problems that once seemed intractable.

Remember that everyone complains about the boss. And almost every great boss is only great in retrospect. The lessons emerge after the pain subsides. What remains is the wisdom you gained from difficult experiences. The words of the Wizard of Oz are instructive. Chided by Dorothy for being “a very bad man,” the Wizard corrects her. “No, my dear,” he tells Dorothy, “I’m a very good man. I’m just a very bad wizard.”

Finally, when you’re working for a Scarecrow, Cowardly Lion, or Tin Man, take responsibility for as much of the situation as you can. Your boss’s problems aren’t your fault; they don’t even have to be your problems. And sometimes you can change the dynamic with a problem boss simply by calling on your own strengths — remembering that “boss” is a title more often than it is a verb. Once you take the initiative, you are starting your own journey down the Yellow Brick Road toward building a better you — and leaving it to the boss to build a better boss.

Professor Len Schlesinger ( builds better bosses at the Harvard Business School. His most recent book is “The Real Heroes of Business … And Not a CEO Among Them” (Currency/Doubleday, 1994).

“10 Questions to Build a Better Understanding of the Boss”

“Boss to Self: How to Build a Better Me”

“Managerial Wisdom from the Journey to Oz”