Shoshana Winter has spent more than thirty years in marketing and communications, working across early-stage tech companies, advertising agencies, and client-side marketing. An extrovert and, by her own description, a student of human behaviour and curiosity, she has moderated panels throughout her career, often on the subjects of women in business and mentorship at a time when senior female leaders were scarce.
Now Chief Executive Officer of Converge, an independent performance marketing agency, she approaches executive dialogue not as a performance to be delivered but as an environment to be created, one where smart people can talk honestly and leave having learned something.
How did you first start your moderation journey?
Shoshana reflects on moderation as a long-standing and natural part of a career built on engaging smart people about an industry she still loves.
“The notion of moderation is a form of reaching a lot of people. I am an extrovert, and I am both a fan and a student of human behaviour and curiosity, so it is a very natural environment for me. I find it a genuinely engaging format, because you hear things that are more spontaneous. You do not really know what people are going to say or how they will respond to each other. The first time was probably decades ago, on the agency side, often around women in business and mentorship, which was an important topic as I grew in my career, because there were not a lot of female senior leaders.”
What excites you about an unscripted roundtable?
Shoshana contrasts the intrinsic pressure of the stage with the safety of the dinner table, where the moderator’s job is to create an environment rather than to perform.
“On a stage you have to be very conscious of your own performance: how much time you take, whether every panellist gets equal air time, whether you are covering the brief. At a dinner with twenty or so people, your job is really about creating an environment where people engage with each other in a way that feels natural.
In both occasions where I had notes, I did not get through all of them, because you have to allow it to breathe. The human insight is that we are craving real-life connections with peers. This format feels safe; there is no skin in the game, and you get an intimacy that our current business environment does not naturally create.”
How has the roundtable format evolved?
Shoshana notes that despite decades in the industry, she had never encountered this particular format until recently, and explains why conference-based versions never felt the same.
“I have attended conferences, spoken at them, and helped put them on, and I had never seen this format until The Ortus Club and one other organisation. At a conference you still feel the pressure, because you know you are at a conference, so it does not elicit the same result as a standalone moment in time. A lot of the time people show up saying it is their first time and they have no idea what to expect, so you get this natural curiosity as well. That is what makes it special.”
What has moderating taught you about senior leaders?
Shoshana is struck less by any single revelation than by the simple fact that busy leaders keep choosing to show up.
“What surprises me is that people are going at all. There is more opportunity to learn and hone skills, online and offline, than anybody knows what to do with, so there is a lot of noise. Yet there is a tremendous amount of pent-up demand for people to be around peers in an intimate way. Even with a free dinner, you still have to persuade someone to spend three hours not knowing what will happen. The most surprising thing is that people take the chance, devote the time, and show up with real engagement and seriousness. It speaks to the fact that you have unlocked an unmet need.”
How do you keep discussion alive?
Shoshana explains that reviving a room comes down to active listening and making people feel that what they said mattered.
“I think humans are searching for ways that they matter. What makes a strong moderator or interviewer is really listening to what one person is saying and using that as data to go back to them. If it goes quiet, I look at the topics we have not covered, then try to recollect something two different people said and re-engage them, building on what happened earlier.
It is effective because it makes people feel they had an impact and that they are, for a few minutes, the centre of attention, which they are. And because it picks up on something that was already a topic, it is not that difficult.”
What would change about how you moderate in five years?
Rather than predicting a fixed evolution, Shoshana frames each session as a chance to learn something she can carry into the next one.
“Every time I do anything like this, my hope is that I learn something from the experience itself. It does not have to be that I should have done it another way; it is more that it is interesting, I wonder what would have happened if. In my last session, it felt like I was losing control, because it drifted into a very unusual direction.
Part of me wondered whether I could have shifted where the wind was going. So I cannot tell you what will change in five years, but I hope that every time I get to do this, there is something I can take away that makes me try something new the next time, because it feels like a dynamic thing.”
What’s one question you will never stop asking?
In a closing reflection, Shoshana turns the lens on her own industry and the growing failure to truly listen.
“Why do people not listen? As a communications executive for thirty years, my job is ultimately about getting people’s attention, so our ability to listen, hear, and understand should be intrinsic to our work. Yet more and more, conversations are not about listening; they are about talking, and if that is all it is, you may as well do it on Instagram.
The whole purpose of being in real life, one on one, is to connect, and that comes from hearing someone. I find everyone’s story unique and interesting, but too often people let someone talk while they are already on to the next thing. People are so worried about defending themselves or being right that they stop taking in anything uncomfortable or new.”
Join the Conversation: The Ortus Club’s Executive Network
Across Shoshana’s insights on moderation as active listening, the pull of the intimate format, and the deep need to feel heard, one pattern is clear: these are not challenges solved in isolation. They require the kind of high-trust, in-person dialogue that transcends the noise of the algorithm and the pressure of the conference stage.
Her vision of the moderator as a genuine listener reflects a broader reality: today’s leaders cannot rely on crowded feeds and clinical events to build the relationships that matter. The most effective executives actively seek out peer dialogue as a strategic necessity, a place to lower their guard, learn in real time, and feel that their contribution counts.
At The Ortus Club, we host curated executive roundtables that bring together senior leaders facing these exact challenges. Step away from the noise and engage in the kind of open, high-value conversations where the real magic of business happens: smart people, together, actually listening to one another.
Frequently Asked Questions
Q: Why does the intimate dinner format work better than a conference stage?
A: It removes the pressure of performance and the sense of being watched. With no audience and no skin in the game, participants lower their guard and connect human to human, producing more honest and spontaneous conversation.
Q: What is the core skill of a good moderator?
A: Active listening. The strongest moderators genuinely hear what each person says and use it as material to re-engage the room, connecting earlier points so participants feel their contribution mattered.
Q: How do you revive a conversation that is dying out?
A: Review the topics not yet covered, recall specific things different participants said earlier, and bring those threads back to re-engage them. This makes people feel their input had an impact and builds naturally on what was already discussed.
Q: Why is there growing demand for in-person executive forums?
A: Remote and hybrid work, algorithm-driven feeds, and large, sales-heavy conferences have left leaders craving real connection with peers. There is significant pent-up demand for intimate, in-person settings where genuine exchange can happen.
Q: What does Shoshana see as the biggest communication challenge today?
A: A widespread failure to truly listen. In an increasingly polarised and distracted world, too many conversations are about talking rather than hearing, which undermines the connection that in-person dialogue is meant to create.
