Build A Culture Of Big Thinking With 5 Simple Questions

As I reflect on three decades of leading marketing teams across companies like Hershey, Capital One, TD Ameritrade, and General Mills, I’ve come to believe that whether you’re selling credit cards or candy bars, digital services or Hamburger Helper, there’s one universal requirement for success: creating the right culture—the feel of the room, the tone in the air, that hard-to-define-but-critical mix of restless energy, hunger for challenge, confidence to strive, open dialogue, and sense of safety in failure.

And while it’s hard to quantify and dissect, it’s easy to detect: Sometimes you feel the difference walking from one company to the next. Sometimes the change can be as localized as walking down one flight of stairs. At the end of the day, I don’t think there’s any single factor as powerful in determining which companies, which divisions, which teams consistently do great work.

Achieving this kind of fertile, creative culture calls for leaders to walk a number of delicate balances: creating space but defining boundaries; allowing exploration while setting a direction; fostering ownership while maintaining accountability; bolstering spirits while setting a high bar for greatness. It’s all too easy to squelch a group’s energy by being overly directive or by ham-handedly pointing out weaknesses in logic or shortcomings in fragile ideas. Nothing shuts down creative energy more than the feeling that the boss already has the answer she really wants.

As I was coaching my daughter, who is in the process of taking on a new management position in her company, I was reminded of a remarkably simple yet powerful tool that has helped me foster this kind of culture as I’ve moved across companies and industries: the question.

The humble question can serve many purposes: push thinking, challenge logic, open possibilities, clarify direction. Done right, it accomplishes all of this without crushing spirits, undermining ownership, or limiting thinking. Here are my favorite questions to probe, clarify, challenge, and encourage:

“How did you …?” This is a great level-setter for early in a dialogue. “How did you arrive at X as a conclusion?” “How did you become convinced that this was the right way to go?” This allows you to probe the underlying logic and soundness of thinking and perhaps indicate some skepticism, without witheringly pouncing on gaps and flaws. If there are weak links in the logic, they will likely be self-discovered in the explanation. You may also find more rigorous grounding than you originally perceived, which you’ve discovered without misguided criticism.

“What if …?” This is the classic invitation to open thinking, creating an invitation to think the improbable and model the vulnerability of throwing out an outlandish idea: “What if we made digital experience part of the actual ice cream product—personalized flavors, Rocky Road fan groups, calorie counters?” This question also allows you to refocus or steer a straying or unproductive dialogue back to a direction you believe to be more fruitful without undermining engagement.

“What else …?” A time-tested tactic in idea generation, well articulated in Edward de Bono’s “Six Thinking Hats”, is to keep digging and digging past the point where you think the well has run dry: “These are all good. What else can we think of to drive trial with no extra investment?” It’s at that moment when you’re forced to really stretch that the unexpected ideas pop, that the self-editing and presumed limits fall away and allow the big thinking in the room.  Asking “What else …” is also far more engaging than, “All these ideas will never work. We’re not done here.”

“Where else …?” I’m a big believer in learning and shamelessly stealing from beacons of success. Capital One made beacon analysis something between an art and a religion. Asking a team, “Where else has this been done really well?” can force people outside their own backyard to extrapolate principles and approaches. This question also enables the creative collision of wildly disparate industries and settings, which can further stimulate fertile thinking.

• “When can we …?” Another proven prompt of boundary-busting thinking is the application of time pressure. Asking “When can we get an MVP in 20 customers’ hands?” can set expectations for rapid forward motion, without aggressively and dejectingly demanding the impossible. But perhaps more importantly, this open yet urgent question can also help free people from some burdens they may have assumed: standards of perfection, rules of how things get done, limits on resources, cumbersome governance and approvals. Turning up the gas in the right way can end up being incredibly energizing and freeing to a great team.

A simple and humble tool, the question can be an incredibly effective way to elevate thinking and turbo-charge output while at the same time energize and encourage your team. So what if you asked more questions and when can you get started?

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