Chapter 10. Give This Chapter to Your Boss

As a rebel, you may want to give this chapter to your boss so that she can better appreciate your value.

As a boss, you may want to understand how to support and lead people in your organization who are constantly trying to change things and introduce new ideas. Then again, you may be a skeptical boss wondering, “Just who are these rebels and what are their motivations?”

Dear Boss,

The first and most important thing to understand about managing a rebel is that this person is not your enemy or even necessarily a troublemaker. In fact, he could be your most valuable employee, helping you identify risks, solve problems, and create better ways to work. The second thing to realize is that many of the young, talented people coming into the workforce think that you want new ideas. They are native rebels who assume that part of their job responsibility is to find ways to improve things at work.

Leaders today talk about the need for more innovative and authentic work environments so that problems can be solved faster, unnecessary bureaucracy trimmed, and opportunities seized. This is exactly what rebels can help you with. It’s what they are especially equipped to do, intellectually and temperamentally.

That said, we realize as former managers of rebels ourselves how tiring it can be to supervise someone who constantly generates ideas, asks endless questions, provokes controversy, and occasionally shows frustration and anger that feel uncomfortable or even disruptive.

This chapter helps you understand how to manage a rebel so that you can benefit from her talents and minimize stress. Rebels need bosses who are self-aware, provide concrete support and a safe environment for honest discussions, and serve more as coaches than old-school command-and-control bosses.

We’ll talk about:

  • What motivates rebels and how they differ from troublemakers
  • How to create the right work environment
  • What kinds of work to give to rebels
  • What kinds of coaching and support rebels need from you so the relationship works for everyone

What Motivates Rebels

To understand how to better manage rebels, it’s helpful to understand what makes them tick, their value, and how they differ from whiners and malcontents. The first and most important thing to understand about managing a good rebel is that this person is not a troublemaker (see Table 10-1).

Table 10-1. Bad rebels versus good rebels
Bad rebelsGood rebels

Complain

Create

Assertions

Questions

Me-focused

Mission-focused

Pessimist

Optimist

Anger

Passion

Energy-sapping

Energy-generating

Alienate

Attract

Problems

Possibilities

Vocalize problems

Socialize opportunities

Worry that…

Wonder if…

Point fingers

Pinpoint causes

Obsessed

Reluctant

Lecture

Listen

Rebels will name the elephants in the room, see new ways to solve problems, bring outside ideas into the organization, and be the first to try new approaches. Our research has found that rebels are especially good at pointing out problems and challenging ineffective sacred-cow practices. Both of these qualities are essential to real innovation but are often shunned in organizations.

Rebels also see risks and opportunities sooner than most people. This is a tremendously valuable competence in an age of rapid change, smaller windows to take advantage of opportunities, shrinking budgets, and increased risk of your organization becoming irrelevant.

One way to look at rebels is as “intrapreneurs” bringing entrepreneurial thinking, speed, and competitive instincts into the organization. They spot ideas and see ways to make them real. The challenge is that rebels often move ahead of most people in the organization, and it’s difficult for nonrebels to fully understand how the rebel’s idea could work given the current realities. One of the jobs of a rebel’s manager is to help build bridges from what exists to better solutions, as uncomfortable as those solutions may at first appear to the nonrebels.

Rebels Want Change That Really Matters

One of the great misperceptions about rebels is that they are trying to change everything or thrive on rocking the boat. Not so. They want to do great work. They want to change things that hold the team back from being its most effective. They are not anarchists. They don’t want to reinvent every wheel. They’re much too practical to change what’s working well.

They do, however, put a lot of effort into eliminating business practices and bureaucratic rules that slow progress without adding value. Bureaucracy creeps slowly. Consensus bloats processes. The “need to know” inflates what needs to be included in standard reports. Legal and quality control “extra safeguards” minimize risk and lengthen the time it takes to get work done. Insecure and inexperienced people add layers instead of revising what exists.

After a while, few people inside the organization can see what’s dragging things down or even understand what the regulation or rule means. If they do, they don’t know how to fix it. That’s where the value of rebels comes in. Unlike troublemakers who rail and rant about how screwed up things are, rebels are often fixers of bureaucracy and unproductive processes. They want to change the rules to reduce the chaos of complexity, creating streamlined order so work can get done faster.

In fact, the mantra of rebel Lars Bjork, CEO of Qlik, is “Love order; hate bureaucracy.”

“Order is where you put a process in place because you want to scale the business to a different level,” he says. “Bureaucracy is where nobody understands why you do it.”

While many people talk about problems at work, rebels recommend possibilities. Whereas troublemakers can become selfish, pessimistic, and obsessed with railing about problems at work, rebels recommend what can work, bringing in ideas from outside the organization and remaining optimistic about what can be accomplished.

They Care More About Work Than Most

Did you notice in Table 10-1 that we said rebels reluctantly recommend solutions? Most rebels are not motivated by recognition, nor do they want to be viewed as heroes. They simply want to solve problems and improve how things are done, either at a small tactical level or by suggesting wide-scale strategic shifts. They want to make a difference. They have a hard time ignoring a problem that they can see a way to solve. Some find it impossible.

Rebels also care more about their organizations than many people. That’s why they’re willing to engage in the controversy and conflict necessary for change and to risk being snubbed for unpopular ideas.

A rebel’s ideas and relentless energy can exhaust or threaten their colleagues and bosses. People sometimes keep rebels at arm’s length, even those who appreciate the value they bring. You may appreciate the rebel’s ideas, but not really want to deal with what’s needed to create change. Good rebels are not “yes people.” They like to really dig into a problem or opportunity, challenging assumptions, asking probing questions, and brainstorming possibilities. Because so many at work like to quickly get to consensus and move on, they sometimes want to avoid a rebel’s creative process. (And we wonder why organizations aren’t more creative and innovative.)

What Signals Are You Sending to Your Team?

The benefits of helping a rebel succeed are considerable. The consequences of ignoring them are also considerable.

If you consciously or unconsciously shut down rebel thinking, you send a signal to the organization that creativity, diversity of thinking, and change are not welcome. When that happens, your best talent usually leaves and the culture becomes complacent. Few are willing to risk their reputations to rock the boat. The culture accepts good enough as good enough.

In today’s hyper-competitive world, how many organizations can survive with a “good enough” culture? How many can survive without the creative thinking needed to solve problems? How can any organization survive without some rebels?

Creating the Right Work Environment

Creating a clear organizational vision, making it safe to disagree, and developing organizational habits that keep the culture open to change are the most useful ways to create a productive work environment for rebels (and for everyone else).

Be Very Clear About Success

When a rebel clearly understands what the organization is trying to accomplish and why, he can focus his energy on creating ideas that support that goal or vision. Without a clear vision, a rebel may go off in many directions, some helpful and others not so much. It’s hit or miss because the rebel doesn’t know what success looks like to you. It’s important to clarify:

  • The organization’s core values
  • The outcomes you are aiming for
  • Where you are trying to go

With this clarity of purpose, the rebel can find better ways to achieve your aspirations. Your role as manager of a rebel is to set the vision, not to tell the rebel to follow a prescribed process or rules to get to that vision (unless, of course, there are significant legal or regulatory risks that could jeopardize the organization if you adopted a different approach). If there is an easier, faster, more rewarding way to get from here to there, why wouldn’t you want to consider it?

Your goals may seem crystal clear to you, but don’t assume they are to your employees. Rebels frequently lament the absence of clear organizational goals.

Clarity about values and outcomes also becomes the filter through which you and the rebel can evaluate and prioritize. This takes away some of the drama and disagreement over whether you like an idea. The filter is more concrete: “How does this idea help accomplish our goals? How does it improve upon the way we do things today?” Again, rebels express enormous frustration over the fact that their ideas are often dismissed without being evaluated based on sound criteria that align with organizational objectives.

Make It Safe to Disagree

How you respond to ideas sends a signal to your entire organization about just how safe it is to propose something new. If you provide thoughtful and useful feedback, approve some experiments, and provide people time to further explore a possibility, they will see that you welcome new ideas and that people in your organization can grow professionally by going beyond their job descriptions. Your organization will become known as a place people want to work because it’s open to doing things differently and better, and you, the manager, believe that employees are a great source of new ideas. Encouraging talent attracts talent.

The most important aspect of creating a safe environment is often the most difficult thing for a manager to do: make it safe for people to disagree with one another and with you.

Many managers mistakenly believe that a workplace with little disagreement is a healthy workplace. Others just can’t stand the uncertainty and disruptive nature of disagreement and controversy. It’s unlikely that any meaningful change can happen without controversy. People would rather do what has worked than have to learn something new or admit that a process or program they created is no longer relevant.

Controversy and disagreement are not about fighting, with one side right and the other wrong. It is a process of examining different views, honestly and frankly discussing the possibilities and potential downsides, and learning. Collaboration requires frank conversations and occasional disagreement. Unlike in sports or public debates, there are no winners or losers. There is no right or wrong in disagreeing at work; it’s about learning to make the ultimate decision stronger.

Make it safe for people, especially rebels, to disagree with you and others in the organization, to ask provocative questions, and to challenge programs, processes, and even (perhaps especially) your opinions. It’s your responsibility to ensure that people feel comfortable asking honest questions and raising genuine concerns. This runs counter to the “strong leader” archetype many of us carry around in our heads, but it is nevertheless essential if you want to ensure that your organization considers all points of view. (This archetype, by the way, provides a convenient excuse for individuals in the workplace not to be more proactive in offering suggestions.)

Meetings are an especially important place to create such an environment. To encourage honest opinions, carve out as much time for questions and conversations in a meeting as you do for the presentation. As the manager, set the tone by asking questions like:

  • How would our competitors view this decision? Would they welcome what we have done? How would they try to take advantage of it?
  • How else might we solve this problem? Have we let ourselves spend enough time really digging into what might be possible?
  • What are we missing?
  • What hasn’t been said that needs to be said?
  • What’s one thing we can do to explore this direction?

Relationships, Messengers, and Heroes

Go out of your way to tell rebels that you’re interested in their ideas. Find time to get to know them outside of official occasions that bring you together. Listen without defensiveness. Engage your curiosity. Ask good questions to understand their thinking and share your thinking and experiences. Try to see through a new lens. Tell them what you appreciate about their ideas. Challenge them to take their thinking further and figure out how they might create experiments to test whether the idea would provide the assumed benefit.

And never shoot the messenger, the bearer of reality, the person who is brave enough to tell you the truth. The rebel is your ally and possibly the one person who can save or improve your reputation by alerting you to danger and recommending a new way forward.

Similarly, don’t make the rebel a hero no matter how good her ideas or yours.

The problem with the heroic leader or rebel is that there isn’t such a thing, at least not for long. An organization incurs considerable risk if it becomes overly dependent on any individual as the wise decision maker. The person anointed as hero is also at considerable risk of believing what people say about him. As former Secretary of Defense Bob Gates once said, “There is something about having great power…that skews people’s judgment.” Work environments are at risk without sound judgment. Never risk this by getting sucked into hero worship.

Beware Your Biases

While managers espouse transparency and employee authenticity, they often judge a rebel’s ideas by how he looks or talks. “If only he were more professional and understood how to work in an organization like ours,” managers often say, which is code for “It’s hard for me to take his ideas seriously.” Or simply, “He’s not like me.”

Take an inventory of your biases. Be fearless when you do, then stay alert to them. (Ask a trusted colleague or two to help you identify your blind spots.)

People should be able to come to work as they are, not trying to look, speak, and use language like everyone else to try to fit in. Effective rebels are both authentic and transparent, sometimes to a fault. They care more about ideas and making a difference at work than they do about creating “the right” impression.

A question to consider: do you inadvertently evaluate people more by their appearance and demeanor than by their ideas?

Create Organizational Habits that Enable Change

Another ingredient of creating an effective work environment for a rebel—and perhaps all employees—is to cultivate healthy organizational habits so that change is less disruptive. You might think innovation is about bringing out the next groundbreaking digital device. It’s not. It’s simply imagining and implementing new, better, more satisfying habits.

How can you as a manager create a culture that adapts to change and even looks for opportunities rather than fights new ideas? Such a culture, in effect, might eliminate the need for rebels.

Consider regularly asking questions that make you and your team think about what you do. During your annual planning process, hit the pause button and set aside time to reflect and discuss things like:

  • How do we know when it’s time to refresh our processes and doctrine?
  • Do we have a review process to help us determine when we need to change something? Who’s involved in that process?
  • What are the habits of my organization? (One useful definition of innovation is “the opposite of habit.”)
  • What initiatives have been successful in our organization? What contributed to the success and how can we use those practices again?
  • How easy is it for people in our organization to experiment with something new? Is it much easier to keep doing what we’ve always done? Do individuals in the organization have to be courageous superheroes to experiment?
  • Are we creating enough small-scale experiments to test our ideas and learn what does and doesn’t work?
  • Do we spend more time on problem solving or on imagining what could be possible? What is the right ratio when we are doing our annual planning? Do we let the calendar or a change in leadership dictate our strategic process? Or are we always observing our environment so that we are receptive to new ideas?
  • How do we balance the paradox of getting work done with finding new ways to work? Of adhering to standards and processes versus taking risks to get to a better outcome? Of rewarding employee cooperation versus recognizing employees for challenging the status quo?
  • What is our process for filtering ideas? Are they helpful filters or blinders?

“Innovation is one of my employer’s five key values,” an MBA student told us, “but I feel many of the organizational leaders don’t embrace it. It’s just talk.”

Innovation can’t be just a word in your mission statement or something that a special task force works on. The climate for new ideas and suggesting ideas needs to be welcoming. Rebels keep telling us, “Management can’t just shoot down our ideas if it wants to grow and prosper.” They also keep asking questions like, “What can we do when management treats us unprofessionally when all we are trying to do is to protect the company from risk and help it succeed?”

As you look at habits, consider spending some time on empathy, the ability to understand how it feels to work in your organization, and particularly what it feels like being a rebel. Is it a safe climate? Are ideas welcomed or even tolerated? Do employee ideas ever penetrate the middle-management ozone layer? Without this sensitivity, it may be difficult to create an adaptable organization. You may be creating greater organizational risk because some managers aren’t allowing new ideas in.

An accurate understanding of organizational realities is a real blind spot for many managers, even those who are very good leaders in other respects.

Don’t Expect Rebels to Have All the Details

The final ingredient for creating a safe environment is not to respond to a rebel’s idea by asking, “Well, how is the whole thing going to work?” Or worse, “You’ve got five minutes. Convince me this can work.”

This is a real leadership moment for a manager. Don’t be the boss whose expectations for neat and orderly change are so delusional that you force your enthusiastic future-thinkers to become hypocrites and package their proposals in slide decks that promise an unrealistic level of certainty. If you demand certainty, you not only will buy into intellectual fraud; you also will eventually tear the heart out of your change champions. We advise rebels to do their homework before presenting their idea and not to conceal its weakness with clever packaging. For your part, ask good questions and explore consequences, but be realistic about how much you can know ahead of time. The real way to test an idea is to experiment with it.

Approach change for what it is—the normal (and messy!) course-correction process that keeps your organization alive. Things externally and internally are constantly changing, and we adjust and adapt in response. Adaptive change keeps organizations healthy, much more so than the big idea, which rarely happens and is often yearned for so that people don’t have to do the hard work of constantly adjusting to new realities.

Give Rebels the Right Work

What kinds of work should you give to rebels? We have three recommendations:

  • Give them real work.
  • Challenge them.
  • Put them in key positions.

Real Work, Not Innovation Task Forces

Don’t consign rebels to an isolated innovation lab or assign them to task forces that are not essential to the organization’s goals.

Rebels know that being asked to do “rebel work” is a career killer. Most rebels are already distraught at having to choose between speaking their minds and stoking their careers. Rebels often hear in performance appraisal sessions that while their work on such-and-such change initiative was admirable, it distracted them from the organization’s mission. Don’t make this phenomenon worse by heaping more such assignments on them.

The Thorniest Problems

Assign rebels to your most challenging problems, when your performance as an organization is on the line. Rebels have a keen ability to create clarity from complexity. They excel at creating new ways to solve problems. Give them a concrete challenge, milestones, and deadlines along with the right resources and support. Take your hands off the controls but coach them along the way.

We have found that rebels can stretch farther and achieve more than you or they thought possible. But as their leader, you must give them cover and protect them from the naysayer chorus who will try to resist or even block their ideas. As a rebel leader, you must believe in your people and what they are trying to accomplish.

Be clear about delegating. Make sure you and your colleagues have a shared understanding of the project. We’ve seen instances in which managers asked a rebel to take on an important organizational assignment and then got cold feet halfway through because the rebel’s approach was so novel. The manager started second-guessing the rebel and asking for more frequent and detailed reports and status updates, distracting the rebel from the real work.

Reports are unlikely to allay your fears, and requiring them sends a signal to the rebels that you’re not sure they can do the job. Instead of demanding reports, drop in regularly on project meetings and ask direct questions about what’s working well and where the group feels stuck or could use help. Unnecessary reports increase unnecessary bureaucracy. Rebels are fighting unnecessary bureaucracy so why heap more on them? Help them with the real work and reduce the busy work.

Positions for Understanding the Organization

Consider giving the rebel work that will help him understand how the entire organization works. Every organization has key positions that lubricate all the other processes—positions like executive officer or chief of staff. These are usually filled by classic high-performing hard chargers. Try a different approach. Bring someone who is known for having different ideas into these positions. We guarantee the benefits and payoffs will be huge. The rebels will learn to be much more realistic and effective in their approach to change, and the executive team will benefit from a more nuanced and forward-looking perspective.

The Art of Managing Rebels

Effective management is an art. Managing rebels so that everyone benefits requires some specialized approaches to this art.

No Lip Service

Saying that you support the idea espoused by a rebel is significant, but not significant enough. Everyone in the organization will look to see if you back up your words with actions.

One clear step is to provide money for implementation. In some situations (for example, in most government agencies), shifting resources is not that simple or can only be done at certain times of the year.

Other concrete ways to support rebels include inviting them to present their initiatives at senior leadership meetings and boosting their status and recognition, both of which can be far more desirable than even money. Consider providing funding for them to visit another organization that has created a similar program. By funding such site visits, you convey to them—and others in the organization—that you value their work and want to help them learn all they can.

Beyond General Coaching

The other type of support rebels need from you is coaching. Rebels at different stages in their careers need coaching in different areas. In general, rebels need particular help and guidance in the following areas.

Help them understand the organizational landscape

Few rebels are corporate or bureaucratic natives, so they naively propose ideas without understanding the process for getting ideas adopted. As their coach, help them understand how the system works and why previous reform efforts failed. Suggest that they get to know people who are experts at getting things done in the organization. Guide them on how to roll out a program to build credibility and gain organizational support. Putting things in the wrong order can jeopardize adoption. You know this; they do not. Help them learn the ropes.

Teach rebels to be prepared

Rebels tend to have great instincts and quickly see ways to improve things. Sometimes they promote their ideas too soon and lose credibility. Ask your rebel good questions to help her think through her idea. Help her understand critical research to support her points. Guide her in anticipating resistance and preparing for objections. Learning to build a case is rarely taught in schools, but it is an important skill for rebels. Help rebels learn to build cases for change that can succeed in your workplace.

Show rebels how to present ideas

It’s so sad when a person uses the same 50-slide PowerPoint deck about his idea in every meeting. Rebels can fall in love with the details of their proposal and want to go through each and every slide with each and every person who expresses the slightest interest. Save this person from becoming a bore. More important, teach the rebel how to create a presentation or meeting strategy. What does he want people to think after hearing his ideas? What does he need them to do? Based on these goals, what should be presented—and what is unnecessary? The objective is to be to be as succinct as possible. Help the rebel influence opinion, not simply present an idea.

Help rebels use controversy productively

Knowing how to engage in productive controversy and healthy dissent is both an essential leadership and rebel competency. Help them learn how to:

  • Show how the benefits of controversial ideas outweigh the risks.
  • Ask good questions that elicit helpful input.
  • Listen to people and express appreciation for their comments, even if you don’t agree with them.
  • Disagree without being disagreeable.

If you can coach a rebel on these skills alone, you will make a lasting difference in her career as well as her effectiveness in your organization.

Guide rebels on the next steps

When rebels fall in love with their ideas, they can’t see clearly. They have difficulty knowing whether support for their idea is increasing, waning, or just not there. They don’t see that they’re getting frustrated and angry and alienating people. They can’t see that they’re exhausted and need a vacation.

As a coach, ask questions to help your rebel find insights about what to do next. Sometimes you may have to be more direct to help rebels know where to stay focused, what to pull away from, and when it’s time to let an idea go because the timing isn’t right or the idea just isn’t going to work. Managers provide much-needed perspective so that a rebel can see the next step. Great managers do this in a way that makes rebels feel appreciated and valued.

Are Rebels Worth the Effort?

People often ask us whether managing a rebel is more work for a manager. Of course it is. Rebels aren’t passive order-takers, but most could be considered an organization’s high potentials, people who can significantly improve the performance of the organization. And they are not only high potentials in leadership, but in all positions.

Traits of high potentials, according to Cornell University labor management professor Samuel Bacharach, include guts and the courage to take risks amid uncertainty. They’ll make tough decisions even if there’s a chance they’ll fail.

Rebels bring guts and courage in spades. They need you to help them understand how to get to know the organization, how to earn respect from others for their ideas, and how to pace themselves so they don’t burn out. Do they require more from you as a manager? Initially, yes. Is the return on your time worth it? Most definitely. They are high performers.

The most surprising value of managing rebels, however, is that they help you grow and become a stronger, more effective leader. A rebel’s curiosity, commitment, and passion will inspire you to see new possibilities for your organization and for yourself.

Questions to Ponder

  • When you think about rebels, what biases come up for you?
  • What might be different if you viewed rebels as allies?
  • On a scale of 1 to 10, how safe do people in your organization feel it is to disagree? What could you do to make it safer for people to have honest conversations about issues important to your goals?
  • What habits are you developing so that new ideas are not an event, but part of how you and your team work?
  • Who are the rebels in your organization? Are they doing the right work?
  • What kind of coaching do team members need from you to learn how to sell new ideas to the organization?

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