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.

The kind of dialogue we wanted to foster is called assertive inquiry. Built on the work of organizational learning theorist Chris Argyris at Harvard Business School, this approach blends the explicit expression of your own thinking (advocacy) with a sincere exploration of the thinking of others (inquiry). In other words, it means clearly articulating your own ideas and sharing the data and reasoning behind them, while genuinely inquiring into the thoughts and reasoning of your peers. To do this effectively, individuals need to embrace a particular stance about their role in a discussion. The stance we tried to instill at P&G was a reasonably straightforward but traditionally underused one: “I have a view worth hearing, but I may be missing something.” It sounds simple, but this stance has a dramatic effect on group behavior if everyone in the room holds it. Individuals try to explain their own thinking—because they do have a view worth hearing.

Your coach then interviews these people [people important to your life and wellbeing] and asks for open feedback on what they think could be holding you back or could become an obstacle to your success. For instance, as Goodman learned with respect to her own leadership, cutting people off in their presentations was inhibiting the free flow of information and, even worse, preventing her from hearing from her own high-potential employees.

Your coach then synthesizes this information for you. As Goldsmith’s clients will tell you, that initial, honest conversation can be tough, as it often challenges your own perceptions, and not necessarily in a pleasant way. Together, you and your coach decide what actions you would like to take to start working on the implications of the feedback and what evidence would suggest that you have been successful in addressing them.

Radical self-inquiry is the path to seeing habits and patterns. Questions that drive us toward that insight are endlessly helpful:

• ‘What parts of me are being projected onto the other person?’ 

• ‘How do I reclaim those parts of me?’ 

• ‘What do my reactions say about me?’ 

• ‘Why do I do what I do?’ 

• ‘Why do they do what they do?’ 

• ‘What need for love, safety, or belonging might they be trying to meet with their irrational behavior?

I suggested she use a tactic I learned from training in nonviolent communications: OFNR. O, for observation of undeniable fact. F, for feeling and assumptions about motivation and other interpretations of facts. N, for needs—individual as well as collective needs. R, for request . . . a request for an alternate way of behaving.

‘Start with the facts,’ I told her. He left the office earlier than expected and he did so without telling anyone. ‘Then,’ I explained further, ‘share how his doing so made you feel’ —in this case, disrespected. ‘Then share with him the collective need . . . that everyone in the company has a need to feel respected. Then,’ I told her, ‘make a request. If he needs to leave early, ask that he let you know in advance.