Right Questions

July 26th, 2018 | Leadership
Guest Post by Aileen Gibb, Conversationalist, Master Masteries Coach (IAC), TedX Speak, Author

There’s a lot written these days about the benefits of leaders asking more questions rather than having to be the one who provides the answers. If you’re a leader who understands that the world is changing, who realizes that your style of knowing what’s right is no longer working — especially for the next generations you now manage in a fast-paced workplace and who seem to make things happen more creatively and expeditiously, albeit they might disregard what you consider to be the right way of going about things — how do you know or learn what questions to ask?

Many of my leadership clients on the receiving end of a conversation with me, will exclaim “What a great question, Aileen.” Some will write it down, planning to use it themselves. Some will ask me what other questions they should be asking.

I answer that I don’t know.

Although I have a seemingly endless repertoire of questions that I ask in coaching conversations, I don’t know what questions are right for you to ask in each of your conversations. So how do I know what questions to ask during a coaching conversation?

I listen.

Yes, that’s the only reference point I have for what questions to ask.

And it’s where the best questions come from.

I don’t know what questions to ask. Instead, I trust what questions are asked.

Questions are birthed from deep listening. Questions emerge from what you’re hearing. From what you’re sensing. From what’s already being said. Or from what is not being said aloud. The questions that make a real difference are the ones which take the conversation, the learning, the insights and the possibilities, to places you could not have planned in advance. In this sense questions are very dynamic, creative, responsive and emergent, relative to the specific moment you find yourself in.

Whilst you may have been taught to be prepared for a conversation. To think in advance what questions you want to ask, I suggest that those prepared questions form only the starting point for your conversation. They might get things going. They might warm things up a little. Yet the real questions will come as you listen in to each other’s thoughts, feelings and insights. Really listen. And when you do so you will find that new questions occur to you. Questions you could not possibly have prepared in advance.

Now there’s a conundrum here.

If you think that you have to have the ‘right’ questions. Or that you have to ask ‘great questions’ you’re going to miss the ‘real’ questions that need to be asked.


Because your focus is on yourself. You may have let go of wanting to be the one with the right answers. Yet now you want to be known for asking the right questions. You want to be the one with the smart questions. In a subtle way you still want to be right and in control of the conversation.

  • Real questions are not about controlling what direction the conversation takes.
  • Real questions are about following where the conversation wants to go.
  • Real questions are the scary ones you hesitate to ask because they seem too risky, or too provocative, or because you don’t already know the answer.

These are the questions we need. These are the questions which stop us in our tracks. Which challenge our perspective. Which shift our minds and open our hearts to new ways of doing, leading, learning and being. The very essence of questions, is that they set us out on a quest to discover something new.

There’s a phrase you may have heard or read in leadership articles that goes along the lines of “there are no right answers, only right questions.” The original quote from which I imagine this modern-day phrase to have emerged is from Ursula K. Le Guin who said: “There are no right answers to wrong questions.” I’d go farther and say that questions cannot be defined as right or wrong. There are only questions that you choose to ask in response to your current context.

What I do know is that the more questions you ask, the more you will learn and discover. And what you learn and discover will be related to how you craft and ask your questions. I’ve had over two decades (if not a lifetime) of practice in listening for the questions that want to be asked and practising how to craft them. I’m not perfect at it yet! It’s a lifelong exploration. I ask a question. Watch and listen for what happens. And then I ask another. And another. And another. At some point there is an insight or a breakthrough where the conversation shifts in an interesting direction that I had not, could not, have anticipated.

That’s when I know I’ve hit on a real question.

Like the revered management consultant, Peter Drucker, my first client, Keith, adopted the leadership stance of knowing that his “greatest strength as a consultant (or leader) is to be ignorant and ask a few questions.” Peter and Keith were of course far from ignorant. For ignorance is quite possibly the fear that drives us to be seen as smart enough to have the right answers. Rather, I’d say both were genuinely curious enough to ask questions to dig into the context in which they were operating. They never assumed to fully understand or to have the answers. Instead they loved to ask questions, knowing it would uncover deeper layers of connection, understanding and solutions.

So by all means, if you know a great coach or a leader who already asks great questions, learn from them. Not by writing down the questions they ask and replicating them. Learn by studying how they ask their questions. How they listen. Ask them where their questions come from. And study how their questions  have an impact on the people around them.

There’s a quote attributed to Bono (by whom I’ll confess to being inspired) that says: “we thought we had the answers, it was the questions we got wrong.” If you think you have the answers, then the questions are always going to be ‘wrong’. It’s when you don’t think or assume you have the answers that your questions will truly open up a new future. Don’t concern yourself with whether your question is right or wrong. Ask it anyway and find your next question in the surprise of what happens when you do.

Aileen Gibb is a master coach and conversationalist, who works with mission-driven leaders and their teams around the globe, inspiring conversation cultures in organizations large and small. Her book, Asking Great Questions: an Essential Companion for Every Leader, contains over 1500 questions and provocative statements to kick-start difference-making conversations with individuals, with teams and as a powerful self-reflection tool for leaders. Once a year she invites a diverse group of leaders into a week-long intensive to practice the arts of listening, questioning and conversation as a leadership edge. Send her an email to join her next sabbatical-like, life enhancing week @ aileengibb@icloud.com or connect with her on her website:  aileengibb.com



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