4 Surprising & Productive Questions for Leaders

“The best scientists and explorers have the attributes of kids! They ask questions and have a sense of wonder. They have curiosity. ‘Who, what, where, why, when, and how!’ They never stop asking questions, and I never stop asking questions, just like a five year old.”
– Sylvia Earle, Marine Biologist, Explorer, Author, and Lecturer

Every idea begins with a question: What if…? Why wouldn’t…? Could we…? Does it…? How can…? And more!

This is how innovative products and new businesses are born. There’s a curiosity, a challenge, or a problem to solve and the entrepreneurially minded ask enough questions to (eventually) arrive at a viable and potentially profitable answer. Indeed, these questions and the basic hypotheses they help to form are the stem cells that grow and mature into successful organizations and firms.

But once those businesses are up and running, something strange happens: the questions tend to give way to statements––those of the entrepreneur, now leader and manager, who has become an operator. “Do this,” “Fix that,” “Cut back here,” “Add some there,” and so on.

The child-like curiosity that birthed the business diminishes and is replaced with directional commands designed to efficiently marshal people and other resources to accomplish the organization’s goals. After all, the popular paradigm is that leaders and managers running maturing or fully mature firms “tell” people what to do. While this is true when it comes to setting and communicating direction, otherwise well-intentioned leaders assume it’s their role 100% of the time. However, both research and anecdotal evidence indicate that in professional settings, a command and control operational leadership style isn’t scalable, exhausts both the leader and their team, and absolutely crushes the morale of highly capable staff.

Of course, there’s a better way: leaders should hold fast to childlike curiosity, talk less, and ask more.

There are four surprising and highly productive questions that successful leaders consistently ask to foster and further capitalize on the curiosity that started it all, while also engaging and growing their team. We’ll explore each in detail below.

Why am I talking?

This meta-question’s function is to create self-awareness. For example, do you have any idea how much time you spend directing and talking versus asking and listening? If you’re like most leaders I’ve met (including my coaching clients), until this moment, this isn’t even something you’ve thought about!

Do you have any idea how much time you spend directing and talking versus asking and listening?

The “Why am I talking” question not only forces awareness regarding the amount of space you’re occupying, but also encourages contemplation of the reason why you’re speaking in the first place. The reality is, sometimes we talk because we think we should be talking, or telling people what to do, or demonstrating our expertise, or filling an otherwise awkward silence. In fact, none of these are productive reasons why a leader should be speaking!

To get your airtime in check, consider monitoring your question-to-statement ratio. Effective leaders ask countless questions which empower others to think, to contribute new and different ideas, and to clarify their own weaknesses and opportunities for growth. I encourage a 20/80 rule of thumb with my clients: leaders should spend roughly 20 percent of their interaction time asking questions and the remaining 80 percent listening to the answers. This one simple practice is a powerful mechanism to motivate and grow your team while also generating more innovative and more complete thinking to fuel your decision-making process and yield even better outcomes.

The bottom line for every leader and manager: know why you are talking in any given moment, and if you don’t have a very good answer, stop. Gather your thoughts, ask a question, and then listen!

The remaining three questions are powerful examples of what you should be asking your people repetitively over time to elicit their best thinking and to help them learn, grow, and improve their capacity.

What do you think?

You’ve probably worked hard to surround yourself with a capable team, but have you created space for them to contribute to their full potential?

Asking, “What do you think” singlehandedly changes the game, shifting your leadership from “commander mode” to “collaborator mode.” It also challenges your people to think more independently and to share more of their (probably very good) ideas!

Keep in mind that it’s crucial to ask this question before you’ve shared your own thinking on any topic at hand! Otherwise, you risk setting the stage for “group think” where your people default to agreeing with you rather than contributing their own thoughts. To minimize this risk, use the best practice I teach my coaching clients: the leader ALWAYS speaks last during discussions and debates.

Asking “What do you think” challenges your people to think more independently and to share more of their (probably very good) ideas!

Once you’ve mastered the use of “What do you think,” you can deploy a slightly more sophisticated version of the question by asking “What do you recommend” instead. Here you’re not just eliciting their thinking, but also expecting them to do the work of synthesizing those ideas into a recommended course of action. This approach raises the bar on your team and challenges them to improve their thinking and contributions to the organization. Use both questions individually or layer them to raise the bar, engage, and elicit input from your team.

What have I/you/we learned?

As I recently wrote, it is critical for leaders and their teams to find time to pause, reflect, and learn. Although it sounds easy enough, in fact, this is a real challenge for many. When you’re running at a full sprint for most of the day, every day—oh yes, and your hair is on fire—it is exceptionally challenging to make time and space for learning! And yet, if you don’t, there’s no way out. You’re effectively sprinting on a treadmill: the view never changes and no matter how hard you run, you’re not going anywhere.

An After-Action Review (AAR) is a productive means of creating an organizational habit to pause, ask “What have we learned,” and ensure the lessons stick. At the conclusion of a project or periodically, as I do quarterly with my coaching clients, allocate focused time to discuss:

(1) what worked;

(2) what didn’t work (and needs improvement); and

(3) what you and your team have learned.

There’s one more step to the AAR that many organizations miss: share the lessons widely throughout your firm. In most cases, a project team’s learnings (or an executive team’s learnings from a given quarter) apply to many others within the organization. Be sure to create a simple mechanism to share the lessons of what worked and what didn’t work widely with your employees.

It’s important to note this question doesn’t just apply to groups; it is also fosters individual learning in a one-on-one coaching format. I’ve found that asking individuals, “What have you learned this week?” typically opens rich and valuable threads of reflection and conversation. Try it during your next 1-on-1.

Why does this matter?

When posed to others, this deceptively simple question prompts them to consider context; why something is or isn’t relevant. All too often, leaders are bombarded with information that others consider critical, but with some vetting, proves not particularly relevant to their priorities. Context always matters but is frequently neglected—often at great cost.

It’s a productive habit to establish context by asking “Why does this matter” before someone presents you with something, whether it’s data, an idea, a proposal, an update, or anything else for that matter. Doing so will create valuable insight, better focus, and fewer time-wasting conversations.

All of that said, you’ll glean even greater value from this question when you pose it to yourself!

Context always matters but is frequently neglected—often at great cost.

As a leader, it’s your job to ensure others have clarity about why an idea, project, or initiative is important to you and to the firm. After all, your primary role is to point to and communicate what matters most to your organization. In my 18+ years developing and coaching leaders, under-communication of context remains one of the most consequential unproductive leadership habits I observe, even in those who consider themselves good communicators!

For many, the primary culprit is the Curse of Knowledge bias. This cognitive bias causes us to inaccurately assume that others have the same information we do. In leadership or management, nothing could be further from the truth!

To appreciate how the Curse of Knowledge bias diminishes communication from the receiver’s perspective, think back to a time when you needed to interrupt someone telling you a story to have them backtrack and provide a missing detail because something didn’t make sense to you. In the instance you’re considering, the storyteller likely glossed over a point so well-known to them that they unconsciously assumed you knew it too, which ultimately led to your confusion.

The same scenario occurs constantly in professional settings. But when you add a power gradient to the mix—that the storyteller / communicator is more senior than the listener—it’s much less likely that the listener will interrupt you to ask for the missing information, that is, if they even realize there is missing information in the first place. Instead, the other person leaves the conversation without a clear understanding of what you expect, what they’re being asked to do, the context of how things fit into a broader picture, and more.

Asking others “Why does this matter” saves time and increases focus. Asking yourself “Why does this matter” inserts a conscious pause to ensure you’re providing the right context and content to those on the receiving end of your communication.

Conclusion

As the late, great engineer, statistician, and management guru W. Edwards Deming succinctly summed it all up: “If you do not know how to ask the right question, you discover nothing.”

When it comes to effective leadership and asking the right questions, quantity matters as much as quality. With these four questions in mind, begin monitoring your question-to-statement ratio and take aim at the 20/80 benchmark.

If you’re not asking enough, right questions—to others and to yourself—you’re neither fulfilling your own potential as a leader nor the potential of the capable people on your team. Even worse, if this is the case, your current leadership style isn’t scalable and is likely deteriorating the morale of your highly competent staff.

When it comes to asking the right questions, quantity matters as much as quality.

On the other hand, asking more and listening more enables your staff to perform at or near their full potential by giving them room and the expectation that they will. This approach, including the four surprising and productive questions we’ve covered here, ensures more engagement and better outcomes for the individuals on your team and, accordingly, for your organization.

What do you think?

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