Chocolate Layer Cake Content

And other key techniques to create great profile content from First Round's Camille Ricketts.

Stewart Butterfield. While the name is now iconic as the founder of Slack, I couldn't recall it before our late 2013 interview though the partners at my firm First Round said an abundance of glowing things about him. I called him up at our appointed time without a real sense of what the story would be. We ended up having one of the most incisive, structured, and deeply wise conversations of any of my interviews.

This is saying a lot. At the time, I had interviewed upwards of 150 of the brilliant people building, marketing, managing and selling technology today for The First Round Review — our publication that surfaces wisdom for entrepreneurs and those who aspire to this tremendous task. Each of these people had stood out in their own way. I think Stewart sticks in my mind because of how precisely and fully he answered my questions about Slack’s go-to-market strategy (now recognized as one of the best-executed plans, perhaps ever). The resulting piece became one of our most popular articles, but the real win for me was that talking to him made me a better interviewer. 

I’d been a journalist and a marketer and an editor for a number of years. Yet Stewart made me realize that the quality of any article depends on the quality of the interview more than anything else. The way that Stewart answered my questions — ordered, measured, detailed, embroidered with examples — made me rethink how I could more proactively surface deep, sequential and organized information. 

This is why I love writing profiles. Everyone I speak to teaches me something new. I’m permitted to have the most profound “getting to know you” conversations possible. I’m challenged to have the writing reflect not just their knowledge, but their tone, their disposition — how they truly think and sound. Along the way, I have learned a number of tactics that have increased my success rate substantially.


Take Their Story Seriously

You have an immense responsibility in telling someone else’s story, so to the best of your ability, it should start with them. Don’t propose a topic by telling the interviewee what their subject is. Instead, keep things open ended to get to the good stuff. 

Today, I always start a piece with a kick-off call with a prospective interviewee. It only takes 10 to 15 minutes, but it makes us partners in picking a topic. What I tell them is that the perfect article will lie at the intersection of what they’re super jazzed to talk about and advice that our readers will find actionable, and ideally, non-obvious. More than 80% of the time, they have something top of mind that we can unpack together. If and when they don’t, I’ll draw on Peter Thiel and ask them to tell me one thing they do in their job that’s different from their peers in the field that has made them successful (thanks to my colleague Shaun Young for this tip — it’s highly effective). Choosing the topic together increases their enthusiasm, ensures that they will in fact have a lot (sometimes even too much) to share, and underscores the goal to provide extreme utility to readers in both our minds. It’s the perfect primer. 

Ask Thoughtful Questions

I take notes on kick-off calls and use them to formulate questions — only about 5 — to send the person as a follow-up. To come up with them, I simply follow my own personal curiosity in the selected area and how this individual became so skilled at it. The most important thing is to word and order them in a way that will parallel the story I’ll eventually write. 

For instance, if I’m writing about scaling an engineering organization, I want my first question to take me back to the beginning of the person’s experience. I’ll want it to establish their credibility and serve as an apt opening to a type of hero’s journey. The middle questions will tackle the primary challenges they faced and the tools they used to prevail. And the last question will always nod to the future — a feint toward what they will do or think about next, how they will scale what they pioneered, what they’re excited to build now.

The question recipient is advised to marinate on this list before the interview. They don’t have to take notes or answer them immediately, simply tuck them away in their subconscious. You won’t believe how much better your interviews will be if you do this. It was like night and day for me.

Create a Layer Cake Story Structure

During an interview proper, I observe the three-tier story system. It never fails to (on one hand) make me think of chocolate layer cake, and (on the other) to draw out the most detailed, useful information from a conversation. Here’s what it looks like roughly:

  • Cake Layer 1: I ask a pretty broad question from the list of 5 I sent over initially. Examples: How do you think about hiring junior data scientists? What’s the most important thing a designer can do when working with a PM? How do use 1-on-1 time with your direct reports? What does your mentorship program for interns look like?
  • Chocolate Frosting (a.k.a. the most important part): I ask one to three follow-up questions to get to the specific how or what they actually do underpinning the answer they just gave me: Yes, but what interview questions do you actually ask? When you share mock-ups how do people comment and respond to each other constructively? How do you walk through and solve challenges with your direct report? How often do mentors actually meet with interns?
  • Cake Layer 2: I ask for examples: Tell me about a time you did this. Is there a story that comes to mind when you say that? When you were at X company, what did this look like? Who were the people involved? What did they say?

The objective is to define an area of interest, quickly get to the actions involved in it (after all, this is what readers can actually learn from and replicate), and use examples to help everyone visualize exactly how an action or piece of advice worked in practice to make it memorable.

Bring Your Best Energy

The single most important tool you have at your disposal to ensure a successful interview: your own energy. If you bring a lot of enthusiasm, warmth and, yes, what might be characterized as downright joy to be speaking to the person in question, you’re going to elevate the experience for you both, elicit much better stories, unearth information that is not easily or usually shared, and, frankly, have a much better time. Human being are mimics to lesser or greater degrees. We mirror each other to create and build rapport. So if you turn the volume up to 8 when the room is at a 5, there’s a good change your interviewee will crank it up as well to match your mood. A 5 gives you the terse, the obvious, the flat. An 8 will give you the colorful, the vulnerability, the spark of interest that readers will feel. 

One of my favorite people to interview is Katia Verresen. She’s an executive coach with many high-caliber clients who I can’t name. But suffice it to say, this woman transforms careers. And it’s no wonder. Her personal energy lights up every room she enters, and all it costs her is a smile, excitement in her voice, and presence in the moment. Whenever I interview her, I end up asking even better questions, going in unexpected directions, and delving deep into funny stories that come up incidentally but connect back perfectly. I’ve seen this work time and time again. Turn up your energy before every interview just a bit.

Realize It’s a Gift

Lessons like these are the constant and continuous byproduct of writing about people for a living. It’s kind of an incomparable profession when it comes to how often something someone says surprises the hell out of you, touches your heart or reshapes your worldview. For me, learning how to do this well has been a deliberate process, honed through various related jobs as a journalist, in PR, in my current role. But it’s a process that always plays second string to the newness of every interaction. You can have your tools at the ready (and you should), but you always have to be prepared to go off script. 



Camille Ricketts, Head of Content & Marketing for First Round, is always looking for new ways to spread the word about First Round's programs, investments, and initiatives to reimagine venture capital. She pioneered the First Round Review to deliver incredible stories and actionable insights to entrepreneurs. Previously, she shaped content strategy for major microfinance nonprofit Kiva, and managed public relations for electric vehicle maker Tesla Motors. Before that, she worked as a journalist, covering green technology for VentureBeat, and culture and lifestyle for The Wall Street Journal in New York and London.