How to Stab Your Boss in the Back

If you have ever entertained thoughts of overthrowing your toxic, out-of-touch boss, the tale of Shakespeare’s Macbeth should serve as a caution: Macbeth, a general, is praised by the king for his valor. One night Macbeth encounters three witches, one of whom tells him that he shall one day be king. Macbeth decides to hurry things along, murders the King and frames the King’s bodyguards. Macbeth gets the crown but is looked upon suspiciously by his rivals-one of whom does Macbeth in.

Obviously, you don’t want to kill your career. Stabbing your boss in the back (even if your department really would be better off without him) is an expedition riddled with peril. So what’s the upwardly mobile IT manager to do?

Be subtle, and let your leadership skills and the facts about your boss’s performance speak for themselves, say career coaches and recruiters. According to Martha Heller, a career coach and managing director of the IT leadership practice at executive recruiting company ZRG: “If you are seen in any way as Machiavellian or underhanded, you will not have the reputation of having integrity and you won’t get the gig.”

How successful you will be also depends on how far up the ladder you’ve already climbed. For instance, a CIO role is hard for any internal candidate to win: Recruiters and career coaches estimate that an open CIO position is filled externally about 60 percent of the time. The reason? Internal candidates usually lack the broad experience necessary to thrive in the C suite.

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But as this how-to guide points out, it is possible to oust your manager and slide into his job. Best of all, you can do it without being a bad guy. By establishing strategic partnerships with the people who have the ultimate hiring and firing power, and by rallying support from those who would be your troops, you can make a case for why a regime change could be healthy for the business. However, once you achieve your goal, you’ll need to be sure you can tackle the problems that led to your boss’s ouster, or you could end up suffering his fate.

1: Assess your boss: Is he or she vulnerable?

Before you decide to put your plans for a coup in motion, you need to make sure your boss is vulnerable enough to be ousted. The red flag for a vulnerable manager is not necessarily a failed project (though those do raise some eyebrows) but the point when he or she becomes the aloof spouse in the unhappy marriage between the business and IT. “If I am interviewing a recently let-go CIO, I usually find that they took their eye off the ball and weren’t busy managing their business relationships,” says Karen Rubenstrunk, an executive recruiter with Korn/Ferry International.

When a manager loses touch, it’s often because she became complacent. CIOs, for example, tend to hold their jobs longer than they used to and have more time to get comfortable. In fact, according to the most recent State of the CIO survey, the average CIO tenure is now more than five years—more than enough time for a leader’s perspective to become narrow.

Patricia Wallington, who spent 10 years as CIO of Xerox, learned a few things about self-preservation. She says she held the job for so long by becoming an agent and facilitator of change, not a hindrance to it. Now, as an executive coach, she says C-level managers who fail to do the same become vulnerable to being overthrown. “They become entrenched in a particular view,” she says. “They have an image of how things should be done, then they stick with it rather than show a willingness to adapt.”

2. Assess yourself: Are you a compelling alternative?

Regardless of how much you disagree with, or even hate, your boss, consider whether you would really do a better job. Odds are, if your boss has fallen out of touch with his superiors or business counterparts, it’s not because they don’t like his taste in movies: It’s because they disagree about some key initiatives. And your boss might be right.

With his higher-level visibility, maybe he sees something that you don’t. Korn/Ferry International’s Rubenstrunk says IT managers typically have between 40 and 80 percent of the visibility into the business that their boss does. “Their perspective is limited,” she says.

But if you’re privy to 80 percent of what’s going on, you can probably make educated guesses as to where the boss is going awry. You might be able to tell when he isn’t dealing well with politics, she says, or is not being assertive enough with new ideas.

According to Susan Cramm, president of Valuedance, an executive coaching firm, if you’re climbing the ladder toward an executive position you also need broad experience, across all functions of IT (and, preferably, across areas of the business as well). “I had a client who had only worked in infrastructure and he told me he wants to be the successor to his CIO. I told him: It’s never going to happen,” she says.

In addition to knowing all the angles of IT and the business, it helps to be a superstar or to possess the charismatic qualities that typically propel people into executive positions. One way to hone that reputation is to win awards, according to Shawn Banerji, an executive recruiter with Russell Reynolds. “Sometimes an award is legitimate and sometimes it isn’t,” he says. “But they show to the rest of the organization that a person has ambition.”

3. Show you’re a leader

Napoleon wouldn’t have become emperor of France if he hadn’t commanded loyalty from his troops, and the same is true in IT. To get support from the people you want to lead, don’t say catty things behind your boss’s back or promise anything you can’t deliver yourself.

Instead, demonstrate the leadership qualities you know they desperately want to see from their manager, who consistently falls short. “You can learn a lot just by listening,” says ZRG’s Heller. “If the guy never makes it out of his office, then you should make the rounds,” she says. “If the staff says he’s all talk and no action, you want to make sure you’re the guy who makes a promise and then follows through.” Then, says Russell Reynolds’s Banerji, they may begin to imagine what life would be like with you in charge.

When your boss takes a vacation or goes on a long business trip and you are put in charge, you have a golden opportunity to show how you would do the job. Heller suggests you might even ask your boss to give you an “acting” title while he or she is away—a subtle way to market yourself as a leader.

Just as you rally the troops in the trenches, you need to impress the other generals, too. If you are running a key project, then you should jump at the opportunity to speak at a budget or executive committee meeting where your project is on the agenda. If you can convey an executive presence, says Heller, they won’t wonder what it would it be like if you were in charge. They’ll already know.

4. Cultivate relationships with businesspeople

Establishing allies on the business staff can be tricky, especially at the highest levels. Talk about ousting a CIO with his C-level boss and you may get him fired. But you might fail to secure the CIO position for yourself because those same people you lobbied won’t trust you.

Korn/Ferry’s Rubenstrunk tells of a coup at a large, vertically integrated organization. The CIO had lost touch with the business and was frequently on the road. While he was gone, his lieutenant started meeting secretly with key executives over lunch and coffee. The lieutenant became instrumental in ousting his boss, says Rubenstrunk, but he didn’t get the job because the executives didn’t want such a blatant backstabber on their team.

A better tactic is to become indispensable. Volunteer for key projects—especially the ones nobody, including your boss, wants to touch. That will provide you with legitimate reasons to speak with businesspeople frequently, says Valuedance’s Cramm. And it will give you an opportunity to shake any perception among business leaders that you’re just a techie rather than a strategic business thinker. In fact, Cramm knows one IT lieutenant who missed his chance to become a CIO when he didn’t sign up for a key project. When the CIO was fired, the company hired someone from outside.

In addition, don’t bad-mouth your boss. Let the facts speak for themselves. If people try to bait you into talking about your inept superior, resist joining in, says Cramm. Instead, ask questions that allow them to vent their frustrations, and then provide context for their complaints. If someone asks you about a project your boss dropped the ball on, you can explain: “A lot of companies approach those kind of projects this way, but Joe decided to do it this way.” If you appear objective, you’ll be more credible, Cramm says.

5. Keep your hands clean

If your boss is fired and you get the job, you want it to be because you are really the best person for the role, not because you played politics. And if your coup fails, you don’t want to find yourself on the unemployment line.

One way to minimize evidence of your involvement is to avoid leaving a paper trail. “Never anything over e-mail. Never,” says Korn/Ferry’s Rubenstrunk. Or, as the turn-of-the-last-century Boston political boss Martin Lomasney is said to have advised: Never write if you can speak, never speak if you can nod, never nod if you can wink. “If you put anything in writing, assume your CIO is going to see it,” says Heller.

Also bear in mind that career paths often cross multiple times. “You want to make sure your boss doesn’t turn around and say you betrayed him, because you will rely on him later on in life to give you good recommendations. And before he leaves, he’s going to ask you what role you had. You’re going to want to answer him honestly,” Heller says.

Heller offers this example: Say you and your boss have always been at odds over a decision to outsource. In internal IT discussions, you go on record as supporting outsourcing, while he still refuses to look into it. Months later, a new CEO comes on board and asks you to join him for lunch. He asks you your opinion on outsourcing. You answer candidly—which eventually leads to the CIO’s ouster. When you have your final lunch with that CIO and he asks you whether you pushed him out, you can be honest about your differences without seeming underhanded.

Or at least as if it’s nothing personal. It will have been, after all, a business decision.