Over the past 2 years, I have published over 200 interviews for amazing founders, operators, and investors across industries ranging from social to healthcare to enterprise to fashion and more. I work on content full time at Zageno (a Series B, General Catalyst backed startup), head content for Elpha (community of 45K+ women in tech), direct content for Harvard in Tech and Techstars Boston, and write for TechCrunch, Pinduoduo, and BIOS. Here, I share my biggest learnings about how to create interview based content from doing effective cold outreach to having great interview conversations to writing tactical interviews to building your brand through content. Cold outreach Instead of framing it as a favor they would be doing for you, frame the interview as an opportunity for them to build their brand, get free media coverage, and generate awareness for their company and work. Present the interview as an opportunity. Show your give first mentality through listing a few ways you can support them, such as sharing product feedback, introducing them to investors or talented candidates, or connecting them with customers or partners. Even if they do not take you up on your intro offers, you show your deep understanding of their needs and show that you genuinely care. People are much more likely to engage with others with a give first mentality. List 2-3 ways you can help. Name other people you have interviewed, especially high profile ones, or interesting companies you have worked for. By leveraging social capital, you establish your legitimacy, build trust, and catch people’s eye, incentivizing them to even open and read through your cold email. Leverage social capital. Share examples of past interviews and be explicit about how much time you need from them and in what time frame. People are hesitant to sign up for ambiguous asks and ambiguous projects. Remove all the uncertainty upfront. Be clear. Beyond referencing their role or generally stating how incredible they are, be specific. Mention a project they did several years ago unrelated to their current role that they may be especially proud of. Allude to a personal passion they have, such as running or baking. Refer to a less well known platform they were featured on months ago. Show that you took the time to get to know them. People want to feel special. Add personalization. Interviewing Go beyond big name people and companies that have already been heavily covered by other media. For example, one of my favorite interviews to cover was with a solo, nontechnical, female founder in the travel tech space in the midst of COVID. While her company did not yet have a massive brand reach, the unique challenges she faced and overcame led to incredibly tactical advice relevant for many founders and operators. Similarly, when you see a company with an exciting growth story, look beyond the founders to silent operators in the company who may have driven the growth, such as their head of growth, director of marketing, VP of sales, or early business development hire. By unsurfacing under appreciated stories, you can fill a content white space and approach a story from a genuinely novel and unique angle. Find under appreciated stories. It can be awkward to have the first interaction be the interview itself. If time allows, have an initial call to answer logistical questions, get comfortable with each other, know what to expect of the other person’s communication style, and better understand their superpowers to craft more relevant questions for them to marinate on. Have a get to know each other call. You should *not* stick to a script of questions during the interview itself because the follow up questions are oftentimes most important, but you should share some topics and overarching questions for the interviewee to marinate on. Even if your questions are centered around their experience and other topics they are familiar with, many memories and insights are buried deep inside people’s minds. If they read your questions and topics in advance, they can mull them over in the back of their minds for a week or two before your conversation, which helps them make connections they would otherwise not be able to make on the spot. Share questions in advance. Interviewees think we only want the big picture, but the most actionable advice is the most micro. Instead of high level taglines like “hire great engineers” (which no one would disagree with and hardly represents novel insight), ask *how* they hired great engineers. What interview questions did they use? What channels did they leverage to source the talent? How did they pitch their company and the role to close the top talent? What types of training and onboarding practices did they implement to grow great talent in their companies? Ask *how* 3 more times than you think you need to. Put yourself in the shoes of your readership. Is this advice they could immediately use without external support? Get to the atomic unit of advice. Writing Instead of having to innovate on structure each time you write an article, remove that obstacle for yourself upfront. Find a structure that fits your style and stick with it. For example, my typical structure is a summary of the interviewee’s story followed by paragraph long highlights of their key insights. Find the structure that works best for you. For example, when I interview people, I do *not* write down every word they say. Rather, I listen first and think about what insight I can draw from the stories and messages they share. I then take notes from that perspective to help streamline my writing process. Take notes with your structure in mind. . I do not record my interviews because people open up more that way, and I more effectively actively listen when I take notes. But as a result, it is easy to forget the nuances from the interview, such as which stories the interviewee emphasized, which stories they shared with excitement or regret or sadness, or the tone of their voice or the subtle changes in their facial expression when they relayed certain messages. So I usually write the same day the interview takes place. I may edit later on, but getting the full story on paper even in draft form helps in preserving all of these nuances. Write as soon as possible Branding It can be easy to lose track of everything you publish. Even a chronological list of your publications is insufficient because it has no meaning. I have aggregated my interviews in 2 ways: on organized by tactical category (categories include things like doing user research, finding co founders, learning about new spaces, scaling companies, and leading large teams) to make it incredibly actionable and on which doubles as my main website where I categorize things by role type (operator, investor, founder) and industry so people can navigate based on their own goals and interests. Aggregate all your interviews. my Coda page my Notion page I use both LinkedIn and Twitter but have found LinkedIn to be the most fitting social network for me. I am less able to come up with pithy, witty phrases throughout the day and like to share more long form content, so LinkedIn has been more aligned than Twitter as a platform to share my content. After publishing my article on Medium or Substack or elsewhere, I share via LinkedIn (aiming to share 3-4 pieces per week to stay active but not overwhelm my audience). By doubling down on 1 main social platform, I reap compounding benefits in growing my audience and cultivating my relationship with them. Find a social channel. I respond to every (nonspam) social comment on my articles natively and via the social platforms I share them on. Doing so incentivizes more people to engage since they know they will be heard and helps to bump your post up in social feeds after your initial posting. Respond to every social comment. Ask your interviewees questions that let them shout out people they admire, appreciate, or work with. Ask about their portfolio companies, board members they enjoyed serving with, role models they look up to, and mentors they are grateful for. The people and companies they shout out are also incentivized to share your content, thereby further amplifying your articles. Empower more brand ambassadors. What one word do you want to be associated with? If you are the 20th person associated with 10 topics, you are effectively not the go to person for any topic. Go for depth instead of breadth. Have a clear end goal in mind so you can optimize your decisions along your journey more precisely to build your brand in a focused way. Have a clear end goal. Can you create a community around your readers? Can you do a meta analysis of the content you have created? How can you get more mileage out of your content through strategic resharing and developing multimedia content? Spend 30 minutes each week to think about how you can go above and beyond. Think about how to build further.

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How Publishing 200+ Interviews Changed My Approach To Interview-Based Content

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How Publishing 200+ Interviews Changed My Approach To Interview-Based Content

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Jessica Li

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