I the concept of rebels in the organization -- and am the rebel. It has not always been with a positive outcome. I am wondering if you have any ideas on how to find the “protectors” within an organization for these people. Specifically, if one was to interview for a job, how would you know if this potential boss would give the rebel freedom and protection?

The right boss can help guide you through the complexities of organizational politics and decision making, and provide an environment where you feel safe challenging the status quo and creating new ideas.

Here are some job interview suggestions I like for figuring out whether a person would be a good "rebel" boss:

1. What is the organization trying to achieve?

This reveals whether a clear organizational purpose exists. When there is a clear purpose, rebels have a much easier time because they can link their  new ideas to how they support the big organizational goal or purpose.  When goals and purposes are fuzzy, rebels can get caught in an unproductive eddy of questioning the validity of the proposed idea.

2. What’s possible that hasn’t yet been done in this [field|company|organization) or What are the greatest opportunities for the organization?

This helps you see if the potential boss is a forward-thinking idea person. (Aside: A corporate rebel recently told me that her new CEO  told the top execs to stop thinking about new ideas and focus their energy on executing his strategy (which they disagreed with).  That no-possibilities boss is losing some of his best talent.)

3. What do you especially like about the organization’s culture and work environment?

The response to this will uncover whether the person is positive and appreciative of the strengths of the organization, or a Debby Downer who defaults to problems and negativity.  From my observations, positive, optimistic bosses are more open to –and appreciative of — rebels.

4. What’s the best assignment/project you’ve ever been involved with?  What made it so fulfilling?

Does the person  most value implementation or creating new things? This idea helps you understand what makes the person tick.  Rebels need a boss who veers more to the creating new things mindset.

5. How do you support people who question approaches that may no longer be effective and see alternative ways to do things?

How a person answers this will be more telling than the words themselves. Is the person comfortable with the question?  Does the answer flow easily and naturally — or does it take a bit  to find the words? Does it sound like the person truly values truth-telling idea people? Or do you detect some annoyance? Does the response indicate that people regularly bring up ideas and the boss has a genuine and comfortable way to support those people and ideas?

Lastly, look around the work environment.  Do you sense a lot of energy and positive buzz?  Or is there a hushed, disengaged feeling? I know this is a bit touchey-feely, but the environment speaks volumes about whether it’s a place rebels can thrive. After walking around the offices of a big ad agency last year, I instantly knew the company was not steeped in creativity.  It was too quiet. People were heads down in their cubicles. There were few fun things tacked around cubicles and common spaces. Sure enough, eight months later I heard the agency had lost three big clients.

Ask your potential boss good questions, and find time to walk around.

-- Lois Kelly