Why I keep a running list of questions to ask other speakers

Every working day, somewhere between the morning coffee and the first email, I open a note on my phone and add a line. Sometimes it is a half-formed thought triggered by something I heard at a conference dinner in Brisbane. Sometimes it is scribbled on the back of a programme during a panel at the Sydney Opera House. Other times it arrives on a long-haul flight, while the in-flight map inches across the Indian Ocean and someone three rows back laughs at a joke I wish I had written down. The list is messy, sprawling, and never properly organised. It is also the single most useful professional tool I own.

I have spent two decades on television sets, in green rooms, and on stages where the microphone matters more than the camera. The question I am asked most often is not "how do you prepare for an interview" but "how do you stop running out of things to say." My answer is uncomfortably simple. I do not rely on confidence, charm, or the hope that inspiration will land. I rely on the list. The list is the engine room. It fuels the conversations I have on air, the keynotes I deliver, the podcast episodes I record, and the boardroom conversations I am invited into across Australia and the UK.

This is a piece about that list, and about the strange, generous art of being a person who asks. It is also about how a habit that started as a survival mechanism in a busy newsroom has quietly become a way of life. If you are a speaker, an aspiring speaker, or simply someone who wants to get better at the conversations that shape your career, the next few minutes are for you. You can find more pieces like this in the officialandreamclean.com/articles archive.

The habit behind the habit

The first version of the list was a folded piece of paper in the back of my diary, dated 2001. I was twenty-something, newly minted as a presenter on a regional news programme, and terrified of being found out. My producer at the time, a patient Welshman called Gwyn, told me something I have never forgotten. He said the person who asks the better question wins the interview, not the person who knows the most. From that week onwards, I started writing down anything that made me tilt my head. A statistic that did not add up. A phrase that sounded good but felt hollow. A guest who looked comfortable saying nothing.

Over the years, the list has changed shape. It migrated from paper to a battered Moleskine, then through a series of phone apps, then to a single recurring note I keep pinned at the top of my screen. The discipline has not changed. I try to add at least one question a day, even on an ordinary day. The questions are not all brilliant. Some are obvious. Some are duplicates. Some I will never actually ask. The point is not the quality of any single entry. The point is that I am training my attention to notice gaps. A gap in my own understanding. A gap in the public conversation. A gap between what a speaker says and what they actually mean.

There is a particular kind of focus that develops when you know you have to write something down later. I notice when a speaker opens with a joke that has nothing to do with the topic. I notice when a corporate CEO uses the word "synergy" as a shield. I notice when a Melbourne audience leans forward, and when a Perth audience starts checking its watches. None of this is accidental. It is the list, working quietly in the background, sharpening what I see.

What the question list has taught me about audiences

Speakers often treat audiences as one large thing. A crowd. A market. A demographic. The list taught me to think about them as collections of small, specific, slightly impatient human beings. Each person in a room of three hundred has turned up with their own internal question list, their own silent version of mine. If my keynote does not intersect with at least three or four of those private lists, the room will drift. Phones will glow. Handbags will rustle. The applause will feel polite rather than warm.

When I look at my list now, it has sorted itself into loose categories. Questions about craft, about why a particular speaker chose to start where they did. Questions about courage, about the moment a person decided to say the difficult thing out loud. Questions about business, about how a speaker prices their work, builds a roster of clients, and protects their energy between gigs. Questions about identity, about what changes in a person when they walk onto a stage and three thousand people fall silent. The most useful questions sit at the overlap of those categories.

The list has also taught me to listen for what is not being said. In Australian corporate events, I have watched brilliant executives deliver immaculate presentations that somehow leave the room untouched. The slides are good. The data is sound. The speaker is polished. And yet. The "and yet" is where the questions live. Why did the speaker avoid mentioning the restructure that everyone knows is coming? Why did they thank the marketing team and not the operations team? Asking those questions, even silently, changes the way you prepare your own material.

Negotiating the stage and the fee

For a long time, I thought the interesting work happened on stage. It does not. The interesting work happens in the week before, when you decide what you are worth, what you will and will not do, and how you will say no without closing a door. Speakers, particularly women, often underestimate this part. We focus on the slides, the wardrobe, the run-through, and treat the conversation about money as a minor inconvenience. The list taught me otherwise. Negotiation is a performance, and it deserves rehearsal just like any other.

I keep a separate section of my notes for the practical questions. What is the brief, really? Who is the audience, and what do they fear? What is the budget range, and who controls it? What does success look like for the client, and for me? These are not rude questions. They turn a vague invitation into a properly scoped engagement. Without them, you end up delivering the right speech to the wrong room. If you are new to this part of the work, my guide on negotiating speaking fees walks through the conversations step by step.

The Australian market has its own rhythms. Corporate budgets in Sydney and Melbourne often lock in six to nine months ahead, meaning a speaker who wants a busy spring is talking to procurement in autumn. Brisbane and Adelaide work on shorter cycles, but the rates are usually lower, which is a useful data point rather than a ceiling. Perth events lean heavily on the resources sector, and the briefs are often blunt in a way that international clients are not. Knowing these patterns does not make you a better speaker. It makes you a more honest one, and honest speakers get rebooked.

Australian stages and how they shape the conversation

I have spoken in most of Australia's capital cities, and the rooms are not interchangeable. A Sydney audience, particularly in the financial services sector, will forgive a slow start but will not forgive vagueness. A Melbourne crowd, especially during the International Comedy Festival, has finely calibrated bullshit detectors and will reward specificity. Brisbane rooms are warmer, more generous, and slightly less convinced that you have earned the stage, which is usually a healthy thing for a speaker to encounter. Adelaide's Festival season pulls in a more literary audience, and the questions afterwards tend to be longer and more philosophical. Perth audiences are patient, practical, and unfussy, a kindness to anyone still finding their voice.

The smaller cities matter too. I have spoken at a regional council event in New South Wales where the audience of eighty farmers taught me more about resilience than any keynote I have given since. I have done a women's leadership breakfast in Hobart where the conversation ran an hour past the official end time. I have been part of a panel in Canberra on women in media that was the most rigorous interrogation of my career I have ever experienced. Each of those rooms produced a question that went straight onto the list.

The Australian business events market has grown over the last decade, and is no longer the preserve of mining magnates and banking lunches. Tech conferences in the eastern capitals, wellness retreats in Byron Bay, education summits in Cairns, and creative industry gatherings in Fremantle all book speakers now. The appetite for honest, lived-experience storytelling is strong. The appetite for keynotes that sound like they were written by a committee is fading. Speakers who arrive with a real list of questions about their own work tend to do well. Speakers who arrive with a script they have not interrogated tend to disappear.

Building your own question list

If the idea of a running list appeals to you, here is where to begin.

• Choose one place to capture questions, and use it every day for at least a season before changing anything. Phones, notebooks, voice memos, all work. The medium matters less than the consistency.
• Write the question exactly as it occurred to you, even if it sounds rough. Polish later. The point of the raw version is to capture the precise gap in your thinking.
• Include questions you are slightly embarrassed by. Those usually turn into the best keynote moments, because they are the questions the audience is carrying too.
• Review the list once a week, even if only for five minutes. Notice patterns, notice which ones you keep avoiding, and notice which ones have already been answered.
• Carry the list into conversations without performing it. Mention a question to a peer. Ask it of a speaker you admire. Listen to the answer without rushing to your next point.
• Use the list before you accept any brief. If your existing questions do not intersect with the proposed topic, either renegotiate the brief or pass. There is no shame in passing.
• Protect the list from people who want to optimise it. A clean, organised list is a less useful list. The mess is where the insight lives.

None of this is theoretical. Speakers who keep a list are more relaxed on stage, more generous in conversation, and quicker to spot when a room is ready to hear something harder. The list is, in the end, the most honest colleague any of us can have.