This returns us again to the central point of this section; the primary challenge you face is not in increasing creativity per se, but in making your company receptive to the vast amounts of creativity that already exist. The point is not to build a company that depends on you for its innovation, but to continually work towards an organization that is as receptive to new ideas as if those ideas had come from you.

Here’s how to avoid the traps that inhibit a questioning culture in many organizations:

1. Avoid Using Questions Like a Hammer. In companies that swing the questioning pendulum too far in the direction of intense inquiry, you often find know-it-alls using questions as a way to stroke their ego and show off. When questions are used as a hammer to drive an existing viewpoint rather than as a flashlight to shine light on new ones, you don’t elicit productive reflection. To remedy this, focus on empowering rather than disempowering questions, which we’ll outline in the ModEl Practices section of this chapter. When in doubt, offer a healthy mix of authentic empathy and sharp curiosity in your questions. I once offered the following private feedback to a constant questioner who was grandstanding a bit and creating unneeded tension in the room: ‘Wisdom is whatever is left after you’ve run out of your opinions. Be careful not to use questions as a means of just expressing a strongly held belief.’

1. Know When It’s Time for Questioning and When It’s Time for Efficiency in Decision-making and Execution. A questioning culture can slow things down and, if it’s a hierarchical organization like the military, it can lead to confusion in strategy or lack of leadership direction. So it’s important to recognize if your organization isn’t built for questioning at times when the pressure is on, deadlines are looming, and stakes are high.

3. Foster Candor and Psychological Safety. Part of the reason many employees don’t feel comfortable asking tough questions is a fear of reprisal for being a ‘troublemaker’—or even losing their job. Author Edgar Schein poses a very important question that leaders can be asked as a measure to determine the level of psychological safety in an organization: ‘If I am about to make a mistake, will you tell me?’ If there is not enough candor and safety built into an organization’s culture to honestly answer yes, then the next question becomes, ‘What do we need to do differently to develop and create that kind of culture?’ Without it, people may take a less candid CYA (Cover Your Ass) approach to communication.

4. Be Clear That Alignment Is the Ultimate Goal of Questioning. A questioning culture is not synonymous with democratic decision making, although they’re often confused to be the same. Companies that do this well make very clear when it’s the right time for questions and potential disagreements and when it’s time to align. It’s critical to be explicit about this. Pat Lencioni’s book Five Dysfunctions of a Team (which we used as an Airbnb leadership team) gives good direction on how to clarify the difference between debate and alignment.

5. Make Sure Senior Leaders Are Actively Engaged in the Questioning Process. If senior leaders don’t actively take part in the questions and debate, whether it’s because they’re not in the room or because they are preoccupied on their phones or laptops, it sends a deadening signal to everyone else. Additionally, when a truth has been uncovered through the questioning process, but senior leadership doesn’t see it or take action, this can dissuade energy expended by the group in a future debate.

CONTRARIAN THINKING. If a problem’s been around for a while, it probably can’t be cracked with conventional thinking. Seek out the positive deviants, like Nucor and Haier. Borrow ideas from other domains, like biology, startups, and crowdsourcing. Rigorously challenge your deepest assumptions. Do all this, and you’ll increase the odds of finding a novel solution.

COMPASSION. People aren’t merely skeptical; they’re cynical—and with good reason. Everyone’s fighting their own corner and looking out for their own interests. When asked to help, most people will ask, “What’s in it for me?” To jump this hurdle, you have to put others first. When colleagues see you working to understand their needs, when you help them craft their experiments, and ensure they get the credit, they’ll start to trust you. When your compassion shines through, people will take risks with you and pick you up when you fall.

CONNECTIONS. Building a community is the most important thing an activist can do. This is the ultimate multiplier of individual effort. Employees eager to try something new often make the mistake of asking their boss for permission. Usually they get shot down, or win only grudging support. This isn’t entirely the manager’s fault. A priori, it’s hard to know whether an underdeveloped idea is brilliant or batty. Since great ideas are rare, the default setting for most managers is to say no. So don’t go up, go out. Talk to your peers. Find a few colleagues who will help you build and run an experiment. It’s easy for a manager to say no to a lone supplicant, but much harder to turn aside a small band of partisans who are passionate about making things better and have already made a start.

Systematic sloughing off of the old is the one and only way to force the new. There is no lack of ideas in any organization I know. “Creativity” is not our problem. But few organizations ever get going on their own good ideas. Everybody is much too busy on the tasks of yesterday. Putting all programs and activities regularly on trial for their lives and getting rid of those that cannot prove their productivity work wonders in stimulating creativity even in the most hidebound bureaucracy.

Systematic sloughing off of the old is the one and only way to force the new. There is no lack of ideas in any organization I know. “Creativity” is not our problem. But few organizations ever get going on their own good ideas. Everybody is much too busy on the tasks of yesterday. Putting all programs and activities regularly on trial for their lives and getting rid of those that cannot prove their productivity work wonders in stimulating creativity even in the most hidebound bureaucracy.