The Route

These Questions will Guide you to Richer Conversations

Hey, I’m Penny Terry and I love writing about ‘soft skills’ while simultaneously hating the phrase ‘soft skills.’ At the moment I’m writing a 10-part series about hosting everything from meetings to podcasts, to events. Even if that doesn’t feel like your thing, I reckon you’ll get more out of it than you expect. We all host something, most days. Either way, we’ll return to regular programming once the series is done.

---

You’ve made it. You’ve reached the part in this series where we focus on the interview itself - how to guide a conversation to sound natural while still uncovering valuable insights.

Like most of us, you’ve probably had some basic training in how to ask questions. Maybe you’ve been told there are open and closed questions. And, like me, you might have wondered, but that can’t be it, can it? You were right to wonder. There’s so much more nuance to asking good questions. That’s exactly why I developed the Question Compass™️ - a tool to help navigate conversations and figure out which questions to ask depending on the answers we’re after. But before we dive into how it works, let me take you back to where it all started

While you might think the Question Compass began during my time as a radio host, its roots go much further back to my very first job (long-time readers may remember this story from The Penny Drop last year).

I grew up on a farm and like most farms, it had lots of fences that created paddocks, and into each paddock, there was a gate. (Hmmm, real thought-provoking stuff so far, eh? Stay with me.)

I bloody love gates. They make me feel quite powerful. (Again, stay with me.)

When I was a kid, I used to ‘go to work’ with Dad on the farm, and my job was Chief Gate Opener (aka: C.G.O.). Don’t laugh—a C.G.O. deals with important and often tricky business.

As Chief Gate Opener, there were lots of different sorts of gates I’d have to know how to open. Some were simple to open as the strainer posts were straight, the strain on the gate was perfect, and I’d simply unhook the latch, and it’d swing open. But often, I’d come across a gate where the hinges were gone, and I’d have to lift it up to unhook the latch, then carry the weight of the gate as I opened it.

When opening gates for stock, I’d also have to consider where they were coming from and where they were going. Some gates led them into big open paddocks, while others guided them into narrow laneways.

I reckon my expertise in gate opening, informed my expertise in question asking. Because questions are a lot like gates. Some are easy and obvious to ask, while others can feel heavy and remain heavy until an outcome or learning is found. Some open up our brains to big pastures, while others direct us along a particular road.

Either way, it’s knowing how to ask the right questions in the right situation that makes us powerful. We’re carving out the route as we go.

I reckon every host needs to be a Chief Gate Opener. We need to understand when to open certain gates in order to guide the conversation along the right path. Some questions are light, exploring experiences, while others are heavy, delving into the beliefs shaped by those experiences. Then there are wide questions, which open up ideas, and narrow ones, which draw out the details.

All of these directions are included on my question Question Compass to help hosts guide the way. Here’s how it works:

Getting our bearings:

Let’s go through the key directions so you can get a good picture of the compass in your head.

• North: This is where we ask light questions, focused on surface-level stories and circumstances our guests have experienced.

• South: In contrast, heavy questions live here, focused on beliefs—digging deeper to understand what our guests have made those experiences mean.

• East: Wide questions open up ideas—they’re expansive, allowing people to explore possibilities and philosophies in broader contexts.

• West: Narrow questions focus on details—they’re about zooming in on specifics, helping us avoid assumptions or biases and get clarity on our guest’s perspectives.

However, most of the time, we’re not working strictly in one direction—we’re navigating the diagonals, moving between these quadrants as we guide the conversation.

North-East: Searching (Ideas and Experiences)

In the north-east, we’re in searching mode. We’re looking at both ideas and experiences, trying to get the big picture before we zoom in. This is where we’re learning about philosophies (the wide view of how someone sees the world) and circumstances (the personal context they’re in). It’s about exploring their environment—both personally and globally—and understanding the broader situation. This stuff is usually pretty light and easy to ask about.

North-West: Extracting (Experiences and Details)

In the north-west, we shift to extracting. We’ve gathered the context, and now we’re pulling out the stories and specifics. It’s about diving deeper into the person’s experiences, drawing out the concrete moments, decisions, and characters that form the narrative. We’re moving from broad ideas into narrower details that make the story real and grounded. Again, this is the top half of the compass and it’s all pretty light and easygoing.

South-West: Clarifying (Details and Beliefs)

Now, in the south-west, it’s time for clarifying. Here, we focus on the details and beliefs. These are the heavier questions, where we get to the heart of what our guest really thinks and feels. We’re exploring their perspective—how they interpret those details—and uncovering the solutions they believe in. This is where the conversation gets deeper and more thoughtful. It’s where draw out the pull quotes.

South-East: Expanding (Beliefs and Ideas)

Finally, in the south-east, we move into expanding. After drilling down into the details and beliefs, now we open things back up again. Here, we explore reflections and possibilities. We’re helping our guests reflect on what they’ve learned and consider what might come next. It’s the space for them to imagine, dream, and expand their thinking.

Using the Compass:

How we use the Question Compass depends on several factors - the type of interview, the audience, and the person we’re talking to (see The Calibration). While balance across all quadrants is ideal, each conversation is unique, and shaped by its situation, relationship, and context. Some interviews may need a lighter, future-focused approach, while others require deeper dives into the past.

The Question Compass isn’t just a tool for preparing and navigating interviews in the moment; it’s also incredibly useful for revealing our own question-asking biases. It can help explain why we might be stuck getting only surface-level answers or why an interview may feel too heavy too quickly. Understanding these patterns allows us to ask more well-rounded questions and have richer conversations.

This Compass has taken me a whole childhood of gate-opening (plus a few decades of actual work) to develop and master. If you want to dive deeper and truly master it, I’ll be taking participants through it step by step in my Ask Better Questions workshop coming up in a few weeks (see details below). After this, you’ll earn yourself the title of C.G.O.

Ultimately, if we’re not opening gates, we’re going nowhere. We’re just stuck in the ute, on the other side, with Dad.

---

Two awesome opportunities:

1. Be Interviewed.

Sometimes as leaders, we need to call in the professional C.G.O.’s (Chief Gate Openers), because we’re too close to our own stuff and we can’t see the wood for the trees… or the paddocks for the gates….

One of my absolute favourite things to do is interview people and help them uncover hidden problems, untapped potential, and buried legacies. But this isn’t just an interview - it’s a full professional development package:

🔸 Pre-interview mentoring session to guide you on how to be a great guest and uncover your best stories

🔸 Tailored preparation to help you dig out key themes and present your ideas effectively

🔸 Flexible interview format - 1 hour via video platform, in-person, or live on stage at your event

🔸 Post-interview feedback and professional aircheck so you hear what was revealed and can refine your message

🔸 Professionally edited final product tailored to your needs. Whether it’s a polished origin story for your website or onboarding, useful collateral for strategy sessions, short social clips, or a report highlighting qualitative insights for decision-making, we’ll ensure the final product serves your goals perfectly.

If you’d like to find out more about the whole process, let’s have a chat and see if it’s the right fit for you.

2. Be an Interviewer.

Get to know the Question Compass. The first workshop in my upcoming Hour of Power Series is a deep dive into the Question Compass. Good timing, right?

It’s awesome for experts, leaders, interviewers and facilitators. You’ll get the full framework to keep (crafted into a handy reusable worksheet) and you’ll learn how to use it to guide well-rounded, rich, and respectful conversations. Check out the full series below - you can join one or all of the sessions, and even book a one-on-one with me.