The best business leaders, entrepreneurs, diplomats, teachers all have at least one thing in common: they ask great questions.

They ask questions that force listeners – employees, staff, students to move beyond simple answers:

• answers that test their reasoning,

• answers that spark curiosity, and

• answers that generate new insights.

They ask questions that inspire your employees to think, and to think deeply! Some business leaders, those with varying years of experience and perhaps the confidence of an organization behind them, are tempted to think their job is to always have the right answers. It’s not, AND no one said you must have ALL the answers either. No one said you have to be the smartest one in the room. However, great leaders inspire curiosity, creativity, and deeper thinking in their employees. It starts with asking the right TYPE of questions. Any answer is only as good as the question asked. People are only going to hear what they want to hear…when the listener lacks color and context.

I find it useful to remember the statement often attributed to Albert Einstein that if he had an hour to solve a problem, and his life depended on it, he would spend the first fifty-five minutes determining the proper question to ask. Asking deep, thought-provoking, introspective questions is not a simple task. It requires us to look beyond simple solutions and to encourage colleagues to do the same. It requires courage and tact, to generate hard questions without sparking defensiveness, as well as being open to new ideas and to questioning untested assumptions. It requires being willing to listen and follow up.

I believe there are some essential questions that are useful across a variety of contexts, including, and perhaps especially, the workplace. We set the tone as successful business owners with the proper Mindset. I’m a proponent of the belief there are only five essential questions in life, and these questions are equally valuable for anyone in a position to lead or influence others.

“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, false beliefs 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.

“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. As adults, no one really cares “why” just get it done and over with is some people’s POV. In the TV series, Ted Lasso, one of the themes in the dartboard challenge was to be curious, not judgmental. The right mindset sparks curiosity and inspection. Similarly, leaders must remain curious about their own organizations 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. Asking “I wonder if…” is the first step in overcoming the inertia that can stifle growth and opportunity for leaders and employees alike. The answer invariably leads to the perfect follow up:. “I wonder if or how can things be done differently?” This question begins the process of creating change sparking the interest and curiosity of those with whom we work.

“What will it take…?”

Most of us have had the experience of sitting through a contentious negotiation, where stakeholders are polarized, progress is stalled, and consensus feels like a pipe dream. Asking “what will it take?” is the question that can help you and your colleagues get unstuck on an issue. It can get you started to a first step, common ground, even if you are not entirely sure where you will end up. Perhaps you might ask, “Couldn’t we at least agree on some basic principles?” or “Couldn’t we at least begin, and re-evaluate at a later time?” Common ground in contentious environments is uncommon and THAT’S what we must have to get the results we MUST have to succeed, thrive or even exist!

“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 help. It helps your colleagues define the problem, which is the first step toward owning and solving it.

“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 you should wait to ask when you are on vacation or are retired. It should be a regular conversation, externally and internally with everyone associated with your business. For example, it’s a useful way to simplify complicated situations, such as sensitive personnel issues, a strategic direction, whether to take on investors, sell some or all of your enterprise. It can also help you stay grounded and gain clarity when you approach that fork in the road.  It can  make 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 rhythm in the broader context of your life.

Business owners and leaders would do well to ask these five questions daily and during critical moments. Of course, these aren’t the only questions to ask; context certainly matters. These five questions are very simple, although not easy, practical and can be replicated and useful to ensure understanding, generate new ideas, inspire progress, encourage responsibility, and remain focused on what is genuinely important.

We’re known for going deeper asking thought-provoking questions to uncover what matters most for you as a seller. Is it a walkaway amount, the opportunity to have a second bite of the apple, or something else?  When you choose to engage JSP, we use our proprietary Data Asset tool which accelerates your current state and what your future state may look like. Time is your greatest currency and if used improperly will kill any potential deal in play. As your stake-in-the-ground advisor, we’re here to support you regardless where you are on your journey.