Mentor Monday

A conversation with Cilian Fennell

Last week, the Highway1 cohort worked with one of our incredible mentors to hone their storytelling and pitching skills.

We sat down with Cilian Fennell of Stillwater Communications for a brief chat to gain some insight into his keen eye for narrative.

When you watch a company pitch, what are you looking for? What’s most important to you?
The first thing I’m watching for is structure: every chapter of a good book, every song has a structure. Where are they finding me? Where are they taking me? And what are they doing in between?

Next I want them to show me there’s a need for the product, and that they’re the team to do it? Can they show they have a route to market, have they mitigated risk, and what’s their ask?

I’ll explore for that while keeping in mind I don’t want everything to be formulaic; you have to leave enough space for the brand’s personality to come through. Is the tone of the company coming across? Are they very serious while trying to pitch a playful product? Do the image and the identity of this thing match?

I’m here for a week at the beginning and two weeks at the end. At the beginning, it’s really about chunking the pitch and having solid structure. I think I force them on a very macro level to articulate themselves better because I’m going in fresh and I need to understand what they’re about.

What’s the most common mistake you see in the early versions of pitches?
That the startup is too close to the product. At this stage, the CEO or whoever’s pitching is so deep in the product’s entrails that they’ve forgotten to step back. The audience has never heard of it before; there’s too many assumptions and expectations of their listeners.

They’ve forgotten to say very simply: this is what we do. Not only that, they’ve forgotten how. They’re so passionate that when they have to step back and say what their product does and why that’s important, it’s like being confronted with a new language — they’ve been utterly immersed in the product and they’ve forgotten how to articulate it to an outside world that’s never heard it.


What’s something you consider crucial that almost nobody does, at least when they first start out?
It takes a long time to go from twenty minutes to four minutes. You know that famous opening line? “Sorry for writing you such a long letter, I just didn’t have the time to write you a short one.”

The things that a company considers the most important to them are not the most important things to the audience. Some of them are obsessed with telling you how their product works, but really, the investor doesn’t care — she presumes it works.

What she’s interested in is: how does the business model work? Can it be manufactured, and is there a market to buy it? We have to make sure there’s enough room left in the pitch to talk about the business, and that’s a very important part: at what point in the pitch are we done with the product? Now that we’ve established what it is and that it’s useful, how is the business going to work?

Is that point different for different spaces?
It’s different for some products — medical devices are a much longer process just from an approvals standpoint — but it depends also on how far along the product itself is. Some products are still on the back of an envelope, and so they’ll be talking about design.

Others aren’t very well developed yet, and so they’ll be talking about the manufacturing. Some are actually done, and the opportunity there is to talk more about the business model.

What tells you when someone’s pretty much done with refining their pitch?
Do they know the flow of their pitch? Do they know where their audience is with each stage? I might take one pitch and break it down: this is the grabbing attention part of the pitch, here’s the teaching part, this is the inspiring part, now here’s is the asking part.

Once we know what each chapter’s supposed to be doing, we then test it against how the audience feels at each stage. Where are we bringing them? What do you want people to know, think, and feel about your product after your four minutes? At a minimum, you want them to know that it works, think it’s got potential, and be interested in the next conversation, which is about investment.

What’s your favorite thing about what you do?
Watching people develop. If you know you can teach other people about a thing, that increases your understanding of that thing. You can’t pitch a product until you’re happy with it. A lot of people try to teach tips and tricks and body language; I don’t. I work very hard on core belief: when you really believe what you’re saying, the body has a magical way of looking after itself. We don’t need tips and tricks when we’re telling our friends about something we’re excited about — our body seems to know what to do.

If we can really work on your belief in your product and your understanding of what you’re doing, then the articulation becomes much more natural and powerful. I love watching that grow. I love watching people get “aha” moments, when they’ve been trying to articulate what they do for ages and suddenly crack it in one sentence. That’s what I’m here for.

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