We’re living in an age of information. No matter what you’re looking for, there’s a YouTube video or a book or website that can answer questions, provide more data or instruction. For every inquiry, there are specific answers out there with step-by-step instruction. In meetings, we each strive to answer every question or uncertainty that may be raised.

However, now more than ever, we’re also stumped by some pretty complex challenges that aren’t answered simply with a Google search or a quick fix. Not knowing is a very vulnerable place to land in today’s world, so we like to jump into a tested solution as quickly as we can. Some of the questions seem so unanswerable that it's easy to ignore them and soldier on, focusing on quick wins or the urgent issues facing us in the moment. 

Instead of taking the context of your workplace or your life for granted as “business as usual” in order to cement our beliefs, we could ask bigger questions to dig into what’s actually going on within the project, our relationship, or our lives. 

Here’s a story that illustrates my point. I am a hobbyist beekeeper with a few backyard hives. Whenever this comes up in casual conversation, usually the response is: “Is it nice to have honey?” or “I hate bees. Don’t you get stung?” 

There are actually not questions but simple micro-conclusions establishing that bees are either a good thing or a bad thing. Sometimes another question or two, but usually we think bees are good or bad depending on our experience. We ask a half-question or make a statement that reinforces our opinion. Bees good = honey. Bees bad = stings. 

Think of the missed questions, the missed conversation, the things we could have learned together with other questions. “What’s the most fascinating part of beekeeping?” “What made you decide on this as a hobby?” “What is happening to cause bee populations to collapse? Do you think it can change?” And sure, asking a larger question takes time and some curiosity, but it’s also a seldom used muscle in our culture.

Alternately, once a year, I go to my son’s preschool to talk about bees. However, I don’t get to talk much. Instead of a Q&A format, it’s just Q&Q and more Q. Asking more questions about questions. My first visit was scheduled for 10 minutes (due to limited attention spans of 4 year olds) but I ended up staying there for 45 minutes of nonstop questions. If you’re a parent, you may know this instinct for questioning all too well. 

But so what? You don’t want to sound like a kid with too many questions.

Well, let’s apply this same principle to your life or your leadership. You’re living life, it’s fine. Maybe not great but okay. Sometimes really good, but also a few things that consistently drive you bonkers.  But notice how quickly we jump to “but this is how it is” and shut down before asking ourselves any other questions? We’re committed to our stories. Besides, opening Pandora’s box is too risky. It’s not our responsibility. We’re in constraints we can’t control. Better not to dig into questions. And, who has the time?

My clients dive into questions with bold curiosity. We open up topics about what really matters to you as a leader. In leading a team or a family or simply leading your life, it's incredibly normal and expected to have breakdowns or blindspots in life. But let’s hold them with curiosity instead of judgement. Let’s see what we learn about ourselves instead of condemning ourselves to the same patterns.

So, what really matters in your life?

Again, we can jump to stock answers “Family! Friends! Health!” But when we press on with more questions, we gain a richness and wisdom that simply wasn’t there before. What matters right now? What matters to your future? When you look at the actions you’re taking in your life today, what outcomes do you expect to get? What did you value 10 years ago?

This isn’t navel gazing or an exercise for the sake of nothing - these questions frequently open up issues we were previously blind to and can now take action on with clarity and energy.

It’s wonderful to see my clients light up with new realizations. They double down on goals because they are re-energized. Questions reveal blocks that have hindered our progress, our leadership and our presence in our own lives. When we see the situation more clearly, we can dissolve and overcome the challenge.

Try it.

Everyday this week, get into a habit of asking a question. Instead of saying “Got it. I’m on it” or making an assumption that you already “know”, push yourself to ask a question. See what happens. What are you curious about? It can be simple. You don’t even have to answer or find an answer immediately but open the question to open the possibility. 

“Does this still matter to me/our company? Why? If not, can it be more relevant?”

“What are my values? How do those show up in my life? Are they the priority I say they are?”

“How can I ensure my time spent each day ties back to my goals? How much time each day do I actually spend on my goals? Have I estimated progress towards my goal? Am I on track? What needs to change?”

“Is my manager (team, family) satisfied with this outcome? Have I asked them if it meets their standards or where it needs to be improved?”

“Who do I trust most on my team? in my life? What makes them trustworthy to me?”

“I’m curious about X, is there someone who has experience with this?” 

“Am I moving in a direction that I want to be moving? What is my destination?”

“What am I committed to NOT doing?”

Yes, it takes some time and reflection to both ask and listen. But answers can be surprising and illuminating.  The next post will cover types of questions that can start rich conversations. 

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Courtney Kaplan works with people to support them in leading a satisfying life driven by their values and their unique goals.