5 Questions Leaders Should Be Asking All the Time

I believe there are some essential questions that are useful across a variety of contexts, including, and perhaps especially, the workplace. In fact, I gave a commencement speech last year on this topic, suggesting to students from the Harvard Graduate School of Education that there are really only five essential questions in life. Although the audience was future educators, I believe these questions are equally valuable for anyone in a position to lead or influence others.

1. “Wait, What?”
   Too often, we jump to conclusions without having enough information. We listen just long enough to form a quick opinion, and then we either endorse or oppose what has been said. This puts us at risk of making faulty judgments, leaving key assumptions untested, and missing out on potential opportunities. Leaders (as well as their employees) need to be able to ask colleagues and direct reports to slow down and explain in more detail what is being proposed, especially if something doesn’t quite sound right or seems too easy to be a lasting solution. Asking “Wait, what?” is an exercise in understanding, which is critical to making informed judgments and decisions—whether in the office or the boardroom.
2. “I wonder why …?” or “I wonder if …?”
   Children are far better than adults at questioning the world around them – nothing is beyond interrogation.  When children wonder why the sky is blue, they prompt others to think, reason, and explain things anew. Similarly, leaders have to remain curious about their organizations in order to bring new ideas to bear on longstanding challenges. Wondering why something is the way it is will sometimes lead to an unsatisfactory answer—as in, we do it this way because it’s easier and that’s the way we have always done it. But asking “I wonder why…” is the first step in overcoming the inertia that can stifle growth and opportunity for leaders and employees alike. That’s because it inevitably leads to the perfect follow up: “I wonder if things could be done differently?” This can begin the process of creating change by sparking the interest and curiosity of those with whom you work.
3. “Couldn’t we at least…?”
   Most of us have had the experience of sitting through a contentious meeting, where stakeholders are polarized, progress is stalled, and consensus feels like a pipe dream. Asking “couldn’t we at least?” is the question that can help you and your colleagues get unstuck on an issue. It can get you started on a first step, even if you are not entirely sure where you will end. Perhaps you might first find some common ground by asking: “Couldn’t we at least agree on some basic principles?” or “Couldn’t we at least begin, and re-evaluate at a later time?”
4. “How can I help?”
   The instinct to lend a hand to someone in need is one of our most admirable traits as human beings, but we often don’t stop to think about the best way to help. Instead, we swoop in and try to save the day. This frequently does more harm than good: it can unintentionally disempower, or even insult, those who need to take charge. So when a colleague or direct report is complaining about an issue or expressing frustration, rather than jumping to offer solutions, try asking, “How can I help?” This forces your colleague to think clearly about the problem to be solved, and whether and how you can actually help. It helps your colleagues define the problem, which is the first step toward owning and solving it.
5. “What truly matters?”
   This question might seem obvious, but I don’t think any of us ask it often enough. “What truly matters?” is not a question that you should wait to ask when you are on vacation or are retired. It should be a regular conversation, externally and internally. For example, it’s a useful way to simplify complicated situations, like sensitive personnel issues. It can also help you stay grounded when you have grand ambitions, like an organizational restructuring. And it can make even your weekly meetings more efficient and productive, by keeping people focused on the right priorities. Asking this often will not only make your work life smoother, but also help you find balance in the broader context of your life.

Leaders should ask these questions both on a daily basis and during critical moments. Of course, these aren’t the only questions to ask; context certainly matters. But I have found these five to be a very practical and useful way to ensure understanding, generate new ideas, inspire progress, encourage responsibility, and remain focused on what is genuinely important.

Source: 5 Questions Leaders Should Be Asking All the Time by James E. Ryan | Harvard Business Review

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