Being brave enough to ask the questions that matter

One of the common misconceptions about mentorship and leadership is that they require having all the answers. In reality, the best mentors and leaders are those who ask the most meaningful questions.

What matters most when asking questions is the state of mind and presence of the person asking them. In leadership coaching, particularly as taught by an organisation called Being Leaders, this is referred to as a leader’s Way of Being, which encompasses their mood, thoughts, body, and self-perception—essentially, how they show up.

Your experience, as well as that of the person you're engaging with, will be shaped by your Way of Being—by the state you’re coming from. So the real question becomes: What state can we work towards to become better askers of questions? How can we create more meaningful experiences and better outcomes for our mentees and those we lead?

This morning, I came across a beautiful quote from a book called The Gene Keys by Richard Rudd, which captures the essence of what I want to communicate in this newsletter:

In a previous episode of this newsletter, we discussed the power of the heart as a sensory organ and its ability to feel signals and send them to the brain. I believe that the best questions come from the heart—these are often the questions we’re afraid to ask because they don’t always follow a logical path. Instead, they may emerge suddenly, as if we’ve sensed them.

These questions might feel “out of left field,” but they are often the most powerful. They can open up new perspectives for the mentee and create a more profound experience for both of you. As mentors, these heart-driven questions allow us to trust the process and let go of the need to over-intellectualize.

Introducing these types of questions into conversations can be challenging, especially when you’re just starting to practice voicing them. Here are a few prompts that may help when you feel a question is important to ask:

• “Something has come to mind—do you mind if I ask?”

• “I have a question that feels relevant—can I share it with you?”

• “I wonder if… or I wonder how…”

As you grow more confident, you may find that you no longer need to preface or soften your questions. Early on, though, using a framing like this can bridge the gap between not asking and asking.

Over time, the more questions you ask, the more you’ll build this muscle and develop confidence in your innate wisdom. This will allow you to bring unique value and insights to your relationships—as a mentor, a leader, a friend, a partner, or simply as a curious human experiencing the wonder of what it means to be alive.

Thanks for being on this journey!

Natalie Shaw
CEO @ OneUpOneDown