Tim Ogle’s moderation journey began at PA Consulting, where, as a side responsibility to his main consulting role, he picked up a broken sales training programme and discovered, within the first hour, that it was really an exercise in moderating a hugely sceptical, mixed room.
Since then, his moderation work has expanded to private equity leadership groups, global sales leadership workshops, and trade forums, alongside his core freelance practice in sales training, sales strategy, and sales coaching. For Tim, moderation is inseparable from curiosity: the discipline of asking better, more pointed questions so that senior leaders do the work of exploring their own thinking.
How did your moderation journey begin?
Tim traces his first real moderation experience back to a sceptical, mixed-opinion room at PA Consulting.
“I worked in a company called PA Consulting, and as part of your job you had to have a side purpose, which was to help progress the capability of the firm. There was a sales training programme that was broken, and I realised one hour into running it that this was a huge moderation job. You had twenty people in the room, hugely sceptical, most of whom didn’t want to be in sales, and it became this world of helping people migrate their mindset. People left the room after two days going, ‘I get sales now, I don’t feel scared anymore.’”
How has your moderation style changed?
Tim reflects on how his style has matured from confident but occasionally clunky challenge into something more deliberate and elegant since his PA Consulting days.
“I think a couple of things have changed since then. I’m probably more prepared, thinking through the scenarios that are going to come about, even if you can’t anticipate everything. I’ve also become more determined in pushing people, really challenging them to say what they actually think and why, and occasionally setting people off against each other. But I think I’ve done it with a bit more guile and elegance. I started doing it quite clunkily, and the result was that I’d sometimes wind a couple of people up, which I never intended. Now it’s smoother.”
How do you prepare to moderate an event?
Tim describes a two-directional preparation process, studying the people in the room before zooming out to the macro forces shaping their industries, while admitting his fatigue with the repetitive nature of AI conversations.
“I’ll look at the people coming, because they’re the audience, the customers, the people who are really here to learn. I’ll look at their roles and their backgrounds, understand the dynamics of what’s likely to be in the room, the personality types, and anticipate some of the problems they’re going to be experiencing. Then I’ll look at the more macro things in the market that are likely to be influencing where they operate.
The obvious one right now is AI, and to be fair I’m getting bored of it, because I must have heard forty discussions on that in the last year, and there’s very little new thinking coming out. It’s the same conversation happening forty times in different places. So the challenge is finding a way to get more engagement and some new insight out of it.”
What has moderating taught you about senior leaders?
Tim explains that working with senior leadership groups has reaffirmed, rather than surprised, his belief that executives lack the space to challenge their own thinking and that they generally welcome being pushed.
“Senior leaders don’t have all the answers, although some of them think they do. They don’t have enough time to explore their own thinking; they sit in a bubble of lots of people saying yes to them, and very few people challenge them. I think challenging them is a good thing, because it helps them reflect and expand their own thinking. It’s very easy as a senior leader to sit there going, ‘I know everything,’ or to feel that everybody expects them to know all the answers, so they can’t show any weakness. I think the art of moderating with senior leadership groups is being willing to take them on a bit, push the boundaries, and give them the space to explore their thinking.”
How has moderating contributed to your growth?
Tim connects his growth as a moderator directly to his decision to go freelance five years ago, describing the value of bringing an outside perspective unconstrained by any single company’s internal rules.
“I went freelance about five years ago, and I don’t have a proper job anymore, which I’m really happy with, because I’m busier than I’ve ever been. One of the reasons I’ve been brought in is because I have that freedom of thinking; you’re not constrained by the rules you’re sat within.
You get to work across many companies and many industries, and you’re not locked into any single ecosystem, so you can bring that thinking to lots of groups by sharing snippets or asking really interesting questions that get people to take themselves down that route. It’s reaffirmed how valuable it is to have external people working around you, because we bring a different perspective, we bring pragmatism, scepticism, challenge, and positivity where it’s needed.”
What is the one question you’ll never stop asking?
Asked to finish the sentence, Tim resists settling on a single line and instead names the family of follow-up questions that define his curiosity-driven approach to moderation.
“I can’t answer that in one thing, because the one thing I will always ask is, tell me more about that, to expand and explore. Or it’s, how did you come to that conclusion, or why do you think that, what caused that thinking? So I haven’t got one answer; there’s about three things in there which I’ll never stop asking. That’s the curiosity kicking in; that’s why I want to know why, and what, and how, and then bring other people into it, such as, where do other people stand on this particular perspective?”
Join the Conversation: The Ortus Club’s Executive Network
Across Tim’s insights on elegant challenge, two-directional preparation, and the discipline of curiosity, one pattern is clear: senior leaders rarely get the space to interrogate their own thinking inside their own organisations. They need a peer-level, outside perspective to do it.
His vision of the moderator as a curious outsider reflects a broader reality: today’s executives cannot rely solely on internal consensus to stress-test their strategy. The most effective leaders, especially those navigating repetitive, hype-driven conversations like AI, actively seek out peer dialogue as a strategic necessity to find genuinely new insight.
At The Ortus Club, we host curated executive roundtables that bring together senior leaders facing these exact challenges. Step away from the echo chamber and engage in the kind of open, high-value conversations that push your thinking further.
Frequently Asked Questions
Q: What does it mean to moderate with “elegance” rather than confrontation?
A: It refers to challenging participants’ thinking in a way that draws out honest views without provoking defensiveness, using tact and timing rather than blunt or clumsy pushing.
Q: Why do senior leaders welcome being challenged in a moderated setting?
A: Because they rarely have time or space within their own organisations to test their thinking; most people around them default to agreement, so a moderator’s challenge helps them reflect and refine their views.
Q: How does preparing for a moderated session work in practice?
A: Effective preparation works in two directions: researching individual attendees’ roles, backgrounds, and likely concerns from the bottom up, while also tracking the broader market and industry forces shaping the room from the top down.
Q: Why might repetitive topics like AI be a challenge for moderators?
A: Because many discussions on hyper-trending topics cover the same ground without producing new insight, moderators must work harder to find fresh angles and provoke genuinely new thinking.
Q: What advantage does an external, freelance moderator bring to a leadership group?
A: An external moderator is not constrained by any single company’s internal rules or ecosystem, which allows them to bring outside perspective, pragmatism, and challenge that internal voices may be less able to offer.
