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.

Stuck on a tough problem? Want to be more creative or encourage creativity in others? Foster a could mindset. Rather than thinking about what should be done, ask what could be done instead. Doing so encourages us and others to take agency, consider new paths, and turn roadblocks into opportunities.

The same holds when asking others for advice. When asking for help, we tend to do so in a specific way: we ask people what they think we should do.

Though this makes sense in some ways, it’s not always the best approach. Asking what they think we could do will encourage them to think more broadly and give us better, more creative direction.

Life design brainstorming has four steps, and a very structured approach to coming up with lots of prototypable ideas. Typically, if you are the facilitator who brings the group together, you might have already framed the brainstorming topic. You want a team of no fewer than three and rarely more than six people who have all volunteered to help. Once the group is convened, the session proceeds as follows.

Most of the time when people tell us “our brainstorm didn’t work,” we find out that they framed a poor question—either one that already assumed a solution or one that was so vague they couldn’t get any traction for generating ideas. Watch out for this when you start to brainstorm with our four-step method.

2. Warming Up

People need a transition from their hectic, event-driven workday to a state of relaxed, creative attention if they are going to do a good job brainstorming. People need some support and a transitional activity to move from their analytical/critical brain to a synthesizing/nonjudgmental brain. It’s a mind-body problem and it takes some practice to get good at making such a transition. A good facilitator takes the lead and makes sure everyone is warmed up and feeling creative. This is essential if the brainstorm is going to be high-energy and generate a lot of ideas.