Top Ten Mistakes of Rebels at Work and One More for Good Measure

Looking over our posts at Rebels at Work, we have captured many lessons from the community’s experience, written about many mistakes and offered suggestions for how to avoid or minimize them. But perhaps it would be a good thing to capture most of them in one place. What follows is a list of what we think are the most common rebel mistakes. In some ways the list is an unpacking of the Good Rebel/ Bad Rebel chart, although I think we all know from painful experiences that “good rebels” can make audaciously bad mistakes. There’s one issue I haven’t included in this list that we have written about often elsewhere: dealing with conflict. We think avoiding conflict at all costs is a mistake; if your idea is meaningful and significant it will engender conflict. But the complexity of conflict can’t be captured by viewing it just through the lens of mistakes.

And now for our list, presented in an order of sorts.

Top Ten Rebel Mistakes

10. Assuming coworkers who are quiet, don’t express a view, or are dull are against you.

Most Rebels at Work have some unfortunate strain of DNA that forces them to speak up when they think something needs correcting. They then assume, I know I have, that those at work who aren’t as vocal don’t get it, don’t want to get it, or just want to get you! Don’t make this assumption and certainly don’t act on it. There are many good reasons why people stay quiet, having to do, for example, with temperament and personality. Some perhaps need to see more evidence before they can commit to a particular course of action. Others choose to defer to authority or existing practices, but, when a new course is set, get wholeheartedly behind it and offer sound improvements.

9. Breaking the rules because rules aren't for you.

Sometimes rebels can get so disgusted with the bureaucratic nonsense in their organizations that they start ignoring certain rules that particularly offend them. Of course, there is no dearth of such rules to ignore; bureaucracies create rules the way urban freeways create traffic jams—and pretty much to the same effect. But deciding unilaterally that you are not going to follow certain procedures is a reliable way of getting identified as a troublemaker in your organization—and thus being denied the maneuvering room and credibility you need to make something really important happen. Rebels need to learn to carry their indignations lightly.

I always thought of myself not as a rule-breaker but as a rule-changer.

8. Being Against the status quo instead of For something.

A common rebel mistake particularly at the start. You can easily see the problems in the current situation without having any idea of what you would do differently. Many rebels never get beyond the “diagnosing the problem” stage. In fact they appear to fall in love with the problems, admiring their many intricacies, reveling in their history. This is always a fatal mistake. The news flash here is that most of the defenders of the current system are painfully aware of its problems. They are not blind to its faults. Far from it. They have made a career of getting the work done regardless of the brickbats the status quo throws at them. The rebels’ tattoo of criticism just seems silly to these scrappy realists who have learned to just get on with it.

By always talking about what’s wrong, you also paint yourself into the pessimist’s corner. People will dread hearing from you at meetings. You become Dr. Doom. Nobody follows a pessimistic rebel.

7. Talking AT people, frothing at the mouth.

A close cousin of Mistake #8, frothing at the mouth is what happens when you as a rebel become so impassioned (or captured) by your change agenda that it becomes your only topic for conversation. You become not unlike a narcissist, only instead of being absorbed with yourself, you are obsessed by your vision. There is no conversational dynamic you cannot turn into an occasion to lobby for change.

A variation of this condition is when the rebel becomes a policy wonk. So even if you focus your attention on solutions rather than on making love to the problem, you can still be off-putting if your dialogue sounds like someone reading an operations manual out loud. Although at some point you will need to lay out how your alternative vision works, it is more important to spend time addressing the values and aspirational nature of your proposals. Linking your aspirations to the values already dear to your colleagues is a good first step.

6. Going All In the first time your organization pursues a strategic change effort.

This is a classic rebel error born out of enthusiasm and misplaced optimism. We all know this scenario.  After years of ignoring calls for change, the organization one day announces a strategic refresh. Perhaps they even appoint some known rebels to the working group that will devise the recommendations for the corporate board. A dangerous moment indeed. Although obviously some organizations will be sincere in gathering the input of rebels, others will either be going through the motions to deflect mounting criticism or—more likely—balk once proposals involving real change are tabled. Proceed cautiously. Don’t assume this is the moment to tell everyone exactly what you think. This is a situation where your befriending of bureaucratic black belts can really come in handy. Before you go all in, gather some good intelligence about how far the organization is really prepared to go.

5. Getting caught in the resource trap.

In those cases when the strategic change effort does amount to something legitimate, then another trap emerges.  Rebels can end up with programmatic responsibility for a change initiative. In these situations I have seen rebels get drunk with bureaucratic power. (A particularly bad drunk.)  Usually in an attempt to test the organization’s commitment to the new agenda, rebels demand that their initiatives be fully funded, even though the organization has already had to do some uncomfortable shifting of resources to free up the monies for the new initiative. In our experience, organizations that have decided to proceed with an important change effort are in a delicate mood; doubters probably still sit on the corporate board just waiting for an excuse to shut this silliness down.  Our advice: be a good corporate citizen. Only take on the resources you absolutely need to prove your concept. Think lean and mean.

4. Losing their Sense of Humor

Watching baby videos can help.


3. Flirting with the Dark Side

Things get dark for rebels when their only goal is to advance their own agenda.  Of course, your ideas are important, but more important than any single idea is the creation of an ecosystem in your organization that is permanently hospitable to honest reflection and change. Perhaps the greatest calling for Rebels at Work is to help organizations evolve from what they are now—protectors of accepted orthodoxy—to what they can become—discoverers and promoters of new ideas.

Rebels can also come to believe they own the change agenda in their organization. Their experiences and the way they like to do things become the new orthodoxy.

Avoid these behaviors at all costs.

2. Putting things in the wrong order.

Ironically, successful Rebels at Work must be able to mimic good bureaucrat behavior. Specifically, they have to approach their change agenda in a disciplined fashion and make careful and thoughtful decisions about how they will sequence their activities. What do they need to do first; what can come next; what can only be attempted after they have reached a critical mass of supporters.

A common rebel sequencing error, one in fact which I've been guilty of more than once, is advertising your reform intentions before you have assessed the organizational landscape in which you are operating. In the government making your goals public before you have a firm action plan only gives fair warning to all those who will oppose you.  They will sharpen their passive-aggressive claws to stop you before you even get started. There’s much for a rebel to do before they give fancy speeches or—God forbid—put together their Powerpoint deck.

And the last and arguably worst Rebel mistake is

1. Wasting your opportunites.

At some point we hope all rebels get several chances to speak to an important audience about their core beliefs. Or perhaps write an important memorandum that will be read by people with influence. When that opportunity comes, don’t fritter it away with an ill-prepared brief, particularly one that just feeds into the preconceived notions many in the organization have about Rebels at Work.

Be organized and substantive. Each organization has a different template for briefings that are to be taken seriously. A Rebel at Work is unlikely to be 100% compliant but don’t go so far off the norm that people aren’t comfortable listening to you and get lost. You don’t want your medium and media to obscure your message. I always want to inject some emotional value into my briefings and talks—often through compelling images, buts at some point I return to what the organization considers “serious.” It’s just a question of respect. Each of us can find a way to communicate our ideas that preserves our integrity.  We just have to think about it and prepare.

Do your homework. I cringe when I think of briefings I've attended where the proponents of new methods just didn't have their facts straight, got critical details wrong, or can’t answer the most fundamental question about what they’re advocating. Aaaargh! How do you expect me to care about your ideas if you don’t care enough to get the facts straight? Consult with everyone you can so that you anticipate likely questions.

Don’t try to fool your audience. Another cardinal sin. Oy! Have you been involved in preparing a briefing where you knew you didn’t have a good answer to a question, so you tried to orchestrate the briefing to avoid having that question come up at all? Is that ever a good idea? NOOO! I particularly enjoy asking the question the briefing team doesn’t want to have to field. I actually think you’re better off admitting up front the questions you still don’t have answers to. After all, change is a work in progress. (For more on this topic see avoiding the Athena trap.)

Tell stories. Have a narrative. Speak to people. See the discussion above about not being a policy wonk.

Take as much time as you need and not one second longer. My rule of thumb: the better you understand your idea, the more concisely you can explain it.


We promised one more mistake for good measure and it’s this:

The worst mistake a true Rebel at Work can make is never speaking up about what is important to them.


If you’re still reading at this point, thanks very much for your attention.