Right Questions – Guest Post on Bob Tiede’s Leading with Questions Blog

This was my most recent guest post for Bob Tiede’s Leading with Questions Blog:

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.

You can find the original post – along with many other great articles on the subject of leading with questions here https://leadingwithquestions.com/leadership/right-questions/


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Aileen Gibb
My work has taken me around the globe and to conversations with people from many different nationalities, cultures and organisations. Wherever I've gone, the power of real conversation, founded on intentional listening and enlightened questioning, has been welcomed. It’s a core piece of our humanity to create the space for conversations that matter and to build connection and meaning with members of our family, our business and our communities.