Leading With Beautiful Questions

Many years ago, we got inspired by Warren Berger’s book, “A More Beautiful Question: The Power of Inquiry to Spark Breakthrough Ideas.” The basic premise of the book and the post we wrote at the time was that leaders simply don’t ask enough questions when they bump up against uncertainty.

Since then, two things have happened. Mr. Berger wrote another book tying the art of inquiry to generating breakthrough ideas (which we all need today), and the world has started to get wobbly. Every leader we work with and talk to is grappling with the issue of how to drive growth in uncertain times. And they’re also looking for ways to unlock new and different thinking on their teams for how to grow. This creates the occasion for us to update our own thinking on the value of asking questions—beautiful questions—to choose the way forward.

Uncertainty can feel familiar

Say that you and some friends are backpacking through a place you’ve never visited before. The call you took from the trailhead drained your phone’s battery and your navigation app is useless (doh!). Your destination is a campsite next to a breathtaking alpine lake that is a jewel of the mountain range and a like-amplifier on your Instagram feed. When you come to a place where the trail forks, with no signs marking the way, one of your hiking companions (who has years more experience in the outdoors than anyone else), declares, “it has to be this way.” 

Who hasn’t been here before?

Either on a trail or in a conference room, strong opinions emerge, experience speaks loudest, the phrase “trust your gut” gets bandied about, and the bias for action short-circuits the deeper process of inquiry. What should you do? Follow experience and take the trail to the left? Trust your gut that tells you not to trust that other person’s gut? Or do you pause to ask a few questions? 

Introspection v. action

When we translate this scenario to the current business environment, it mirrors a lot of today’s context: navigating landscapes (economic, market, technology, talent, etc.) that are unknown or unpredictable with limited information to guide you to the promised land. It feels like every day there is a crucible moment that can slow down progress or knock your leadership team out of alignment. And alignment is the key issue here. 

A basic assumption in team dynamics is that too many questions will slow us down, and that quick answers will speed us up. This is true, but only to a degree. Without alignment around those answers, you’ll actually move more slowly people will drag their feet or hold back in other ways until the direction proves to be correct. It’s like a cycling peloton that rides single file—you can’t draft off each other in this formation. 

On the other hand, lemmings show incredible alignment. But maybe they should learn to ask a few more questions.

The question leaders face during times of uncertainty is whether they should lead with answers (and keep the foot on the accelerator) or lead with questions (and do the soul-searching that builds conviction and alignment)? We think the answer is both. And here’s a simple framework for how to do it.

Identify the operating narrative

Simply put, times of uncertainty = times of fear. When we perceive danger, our amygdala gets activated, and our fight, flight, or freeze instincts take over. Expansion, contraction, or stasis. And when this happens, we begin constructing our own narratives based on how we individually deal with fear. 

One person might choose to avoid risk (not taking another step forward), while another wants to leap into bigger risks (bushwacking to the nearest peak to get a better perspective). Your fellow hiker could employ head-in-the-sand behaviors that delay conflict (acquiesce but then grumble the entire time), while another could rebel (go back to the car to charge the phone). While these could all be appropriate actions, they put your organization at risk because they skip the most important step for how teams move through uncertainty. A leader needs to establish a unifying narrative first to build alignment. And then the action can follow.  

Ask beautiful questions

Because we all have different relationships with uncertainty, we need a way to get onto common ground. And the best way to do this is to ask questions that reframe the situation.

Berger’s books highlight how when we’re children, we’re full of questions because nothing is at stake when a kid asks a question. But as we mature many of us lose the willingness to reveal what we don’t know (except for the stellar innovators and leaders who are always in learning mode). By offering helpful guides to using a flow from “Why?” to “What if?” to “How?” Berger shows us how to gain awareness of what people want and need, what they’re avoiding, and where the new opportunities lay. 

Unfortunately, when the tension is running high and the talk turns to execution, people want answers and action rather than another @#!$& beautiful question. And there’s a price attached to this anti-question bias in business. As companies push away from asking bigger questions in the spirit of addressing short-term needs, they stop looking for the opportunities, trends, and threats that are just around the corner. And they let external narratives (the economy is slowing and companies in our industry must cut X, Y, and Z to survive) take over when they should be formulating their own stories (e.g. by shifting our efforts or leveraging our unique strengths, we can set the stage for the next five years of growth).

The best part of this is that questions are free, with the only cost being the amount of time you invest in exploring them. And by undertaking this process, can achieve results that range from alleviating stress to re-framing your opportunities to unlocking entirely new ideas for your business. 

To give you a sense of how asking beautiful questions can help you shift your narrative, below are a few inspired by Berger’s books:

• Why are we in business? (And by the way, what business are we really in?)
• What if we become a cause and not just a company?
• What fears are holding us back?
• What do we stand against?
• Who does our company look like at its very best?
• Where in our company is it safe (or unsafe) to ask radical questions?
• Does our mission make sense? Do we embrace it? Does it unify us? 
• What are we doing the way we’ve always done it?  Is it still working?
• Where is the place we can be a start-up again?
• If money were no object, how might we approach our work differently?
• How might we create a culture of inquiry?
• Does our future make us feel like dancing? How could it?

You’ll notice that these are open-ended questions that don’t necessarily have right or wrong answers. They’re not koans intended to stump people, but by they do have the power to get people into healthy debate (a conversation you enter into with a willingness to have your mind changed). And these questions are by no means exhaustive. Think up a few of your own that will rattle the cage (in a good way) during your team’s next meeting.

Translate questions into actions

Spending time in shared inquiry is the quickest way to regain alignment when things are wobbly. As a regular practice, it deepens alignment that allows your team to make decisions faster, think bigger, and reach higher levels of performance. By discussing these questions in ways that activate both the head and the heart, you identify the right actions to prioritize that will move the needle for your business while also keeping employees engaged and inspired.

When you’re aligned as a team and everyone feels that they’ve had their say, execution becomes easier. Decisions are more intuitive. You form collective gut reactions that honor everyone around the table. And you locked in on the key priorities for moving into the unknown. You might realize that the way forward lies in focusing on core customers. Or innovating your go-to-market motions. Or giving everyone in the company a day to reflect on a single question that will unify the team. Action is a force of expansion, and aligned action is the quickest way to make progress toward your shared goals. 

Your brand strategy is an alignment tool

Your brand strategy can be the catalyst for a culture of inquiry. Many of Berger’s questions are fundamental to building a brand that is authentic and differentiated. When your brand seeks to embody a purpose beyond profits, you get to explore the motives, orientations, and attitudes of your company. You create the space to ask difficult questions that lead to revealing and powerful answers that are rooted in meaning and emotion. This leads to a brand that navigates the world in a more purposeful way, asking the questions that need to be asked of itself, and discovering the meaningful connections that help them prosper.

Ask the questions. Live the answers. And thrive.

Emotive Brand is a San Francisco branding agency