Behind the Scenes of My Podcasting & Interview Process

Since I announced my book Dabblers vs. Doers a few months ago, I have been in a process of research for the book that includes interviews with various creative professionals. I decided to share that primary research live as it happens via a podcast and accompanying blog posts. Just look at these awesome people I have spoken to so far:


Today, I want to give you a behind-the-scenes look at that process.

Who I choose to interview

When I first considered doing interviews as part of the research for my book, a few names popped into my head right away. Some were people I knew, others were not. In general, I find myself focusing on creative professionals who are mid-career; those who have found some success and are working hard to balance the drive to create meaningful work with the difficult demands of that process. These are also people who have figured out how to live a healthy life outside of work itself.

In other words, I wanted to talk about their struggle in that place where these things break down. Because “doing it all” is a process, not a destination, and the reality of that is what my book is all about. How we take personal risks in our professional journey.

I sought people from a wide variety of fields, each broadly defined as a “creative professional.” So far, I have spoken to:

In reviewing this list, what becomes immediately apparent to me is how difficult it is to define each of these people with a single role. Each person, even just professionally, assumes many roles.

As I conducted each of these early interviews, I found that we went deep in so many ways, but that one narrative seemed to jump out at me for each. Some have discussed coping with deep depression, or working through their experience of being an extreme introvert, with learning disabilities, among so many other deeply personal topics.

After I did about 10 interviews, I began asking a handful of friends who else they recommend I interview. That immediately produced a list of 5-10 suggestions (which I am still working through).

But then those names produced even more recommendations. I nearly always ask an interviewee if they have suggestions for someone else I should interview. So now I am working three degrees away from where I began: asking a friend who I should interview, interviewing that person, now interviewing someone that person recommends.

It’s so cool to dig in deeply with these people, but also to make so many new connections! I created a spreadsheet to track ideas of who to reach out to, and my status of each of those leads or requests.

How I reach out to them

I created an invitation template that I send to each person I hope to interview. It covers the following:

  • The “ask” – would they be willing to be interviewed on a certain topic, and why I asked them in particular
  • A request for an hour of their time, either in person or via Skype
  • Full disclosure that my interview will be recorded via video and audio
  • Explanation of how this will be shared in the near term (podcast, blog post, social media)
  • Connection to my book, that this interview will ideally be integrated into that

When inviting someone, the barriers I am most concerned about are:

  • The ask is too convoluted. So I try to keep it short. One line on my book, one line on why I want to chat with them, short but specific bullets outlining what I would like from them.
  • That they will think this book (or I) am irrelevant to them and their work.

Generally, people respond to me and most have said ‘yes.’ There are a few people who never replied back. Which is a bummer, though I understand that they are busy, and likely have a long list of incoming emails.

What has surprised me is that some of the people I reached out to are pretty much famous, and they are the ones who have responded to me the quickest. Like, within hours of my request.

From this group, the ones who answered yes sent me replies that were short and filled with action. Literally a single sentence without a greeting or signature. Something like: “Would love to, as long as we can do it at my office during lunch. May 5th works.”

This surprised me, and what I find is that people who are busy are used to making quick, action-oriented decisions. They manage a lot of decisions, a lot of people, and are simply in the habit of checking their phone while waiting for coffee — making a decision, communicating it, and managing their ever-changing calendar.

Those who are very well-known, but said ‘no’ to my request, clearly had a process in place, and a pre-written messaging. For example: “Hi Dan, Thank for the kind offer, but I’m saying no to everything right now while I finish my current book. Good luck with the project, it sounds interesting!”

Again, this surprised me because they are clearly so proactive in dealing with their limits. So many people I meet say they are overwhelmed, and I think that embracing and coping with limits is a key way to not feel that as much.

One very cool part of this process is that I am learning from these people — the ones who say yes, the ones who say no, and even those who don’t respond. I will absolutely follow up with the ones who don’t respond, though. A single email could easily get lost, or arrive at exactly the worst moment. I have loads of empathy for how much each of these creative professionals juggles in their personal and professional lives.

As for why people say yes, I’m never fully clear about that. My gut is that it’s nice to have someone ask you for your wisdom. For instance, there is NO REASON why Tina Roth Eisenberg should have said yes to me. I asked her about this, and she said that I did a good job of connecting with her via social media, and she made a split-second decision to just invest in karma (my words, not hers). That she knows spending an hour of time with me could, in some way, have a wonderful, serendipitous effect months or years down the road.

When I reached out to Jeremy Chernick, the special effects designer, I was well aware of how busy his life is. He got back to me within hours, and met up with me just a week after I reached out. The day we met, he was incredibly busy, and literally running into our meeting, and running out of it. RUNNING. Yet, he gave a gracious and deeply personal interview in the 50 minutes he did spend with me.

Why did Jeremy say yes? I have no idea other than that I came to him via a mutual friend. Jeremy had every reason in the world to say “No thanks, I’m busy,” or even to cancel our meeting the morning of.

But what I observed was that a big part of Jeremy’s life is to make meaning around the work that he does, to help others understand the reality behind special effects and the work of the company he works for. Perhaps he was asked three years ago to be in charge of public relations for his company. Perhaps he just enjoys that role. Perhaps it was another reason. Regardless, he left me deeply impressed at every moment of my communication with him. The speed and the depth.

How I research interviewees and prepare questions

My research process can be described in one word: OBSESSION. I obsess over these interviewees. By the time I actually speak to them, I have not only become a fan, I have read every word about them that I can find, and have nagging questions about portions of their lives that were opaque to me in the research.

It’s weird, but I feel like I’m sitting down with a celebrity, because I have ‘lived with them’ for days in my research, and now here they are, just across the table from me, and I’M ALLOWED TO ASK THEM ANYTHING!

As I research, I begin with basic Google searches on their name. I explore every link I can find, every rabbit hole I can possibly fall into. So if that person has a website, I click every single link on it that I can find.

I will do Google searches that have date limits on them, such as ONLY looking for mentions of their name online prior to 2006, before social media, or before their most recent job.

If I find other interviews they participated in (text, audio, or video), I study them. I read every article about them I can find, and as much as possible, every blog entry and social media update. More on that last one below.

It’s worth pointing out that the themes I am focused on are very particular. I want to explore the personal/professional challenges they navigated as they embraced the idea of risk in their career.

I don’t focus on how they create their work. If I am interviewing a painter, yes, it is nice background to understand their painting process, but I won’t be asking any questions about this in my interview.

I don’t focus on stories I have heard before. I always ask for a 40-minute interview, and I want to use that time to explore themes and stories I have not heard them discuss elsewhere. I will sometimes take a single quote from another interview, and use that as the basis for an entire line of questioning.

I don’t focus on accolades or big achievements. Again and again, I find myself focusing not on their biggest success, but about a period of their lives that was much earlier in the journey. For instance, when I interviewed Jeremy Chernick, I focused very little on his most recent work in the new Broadway musical Aladdin. Instead, I was SUPER excited to hear about a road trip he took when he graduated college.

In short, in my research I am looking for the gaps, for the things that aren’t often discussed.

For instance, in researching artist Eric Wert, there were PLENTY of great articles on his artistic process. Not only is it not the focus of my book, but because of these articles, that itch has been scratched. I want to dig into areas that others haven’t.

I try to read every social media update that is available, and tend to find the gold when I go as far back as possible. I will friend them on Facebook and scroll back, post by post, year by year. Same with Twitter, Instagram, etc. It’s not enough to just quickly scroll through Instagram photos; I read the updates.

Oftentimes, I dig even further, not just reading all the old Facebook posts, but reading the comments as well. The Facebook status update may mention them feeling creative anxiety, but the comment thread with friends may be where they provide more useful context.

Recently, I realized I need to do even better at this. For one interviewee, Tammy Greenberg, she had blogged since 2005 — a huge archive. I didn’t go through every post and sure enough, something from years ago came up in our interview. She said “I blogged about it,” and I missed it in my research. It was SUCH a perfect example of the topic I am exploring, I am just thankful she brought it up. I now spend even more time researching because of this.

What I find is that for each person, there is one channel that seems to deliver more gold than others. For some, it is their Facebook updates, for others Twitter, and for others, it is listening to interviews they recorded or shared with other media outlets. Every time I hit a dead end in research, I keep looking and nearly always find a thread that leads somewhere good. That is often at minute 39 of listening to an interview with the subject, after hours of research. They say something that aligns with the topics I am focused on, and a light bulb goes off.

What is the result of the research? To ask better questions, to have a literacy of the person and their experience so that my time with them is not spent asking questions that have already been answered. It is my goal to dig deep into the emotional stuff that often isn’t talked about publicly. I can only do that if I have as complete an understanding of that person as possible.

How I prepare for the interview itself

I have shared in-depth posts about my podcasting equipment here and here.

In preparing for the actual interview, a big focus is to set expectations with the interviewee. I let them know any technical details they need to be aware of:

  • For Skype interviews, close all other programs so that we have more bandwidth for audio/video.
  • For in-person interviews, please don’t tap on the table when making a point, because it comes up as loud noises in the microphone.
  • Please turn off their cell phone.
  • I test audio levels, and ask them to be sure to speak directly into their microphone.

I have a checklist, and a big item is to indeed remember to click the ‘record’ button. I do backup recordings as well. Checklists are a critical part of a process such as this. If I am interviewing someone in Brooklyn, it will have taken two hours to reach them, days of research, and it is entirely possible that I could miss that single — but critical — step of pressing the ‘record’ button.

I also restate other expectations with the interviewee. That this interview will indeed be recorded via audio and video, and that the master audio file will be shared publicly in a week or two. I confirm that we will chat for 40 minutes. I review the topic focus again (navigating risk in their career), and I let them know that — at any point — if I ask a question that is too personal, they can just redirect me. I also tell them that if, once the the interview is over, they shared something they now regret, that I will gladly edit out of the final interview.

For the interview itself — the moment after I click ‘record’ — I have found that it is good to engage them in the topic early on, because they also give me signs of opportunities for further exploration around the topic. For example, I would rarely bring up a topic like depression with someone unless they bring it up first. I do NOT want to pry where my queries aren’t wanted. So I look for topics, but also for where they are WELCOMING me to open up lines of questions.

When I arrive to interview someone, I immediately begin setting up my equipment, and can have it all prepared and ready to go within five minutes. When the interview ends, even though the person is usually still having polite conversation with me, I rush to pack up my stuff and leave. I always want to be respectful of their time, and never ever take up more than an hour total for the interview, including setup and saying farewell.

How I prepare for the interview dialog itself

I do not have a set list of questions, even for an individual interview. I have COPIOUS notes that have general topic areas to explore, but no specific questions.

The conversation itself is an exploration, and it often goes wildly off-script, which is exactly what I want.

As I move through an interview, I am looking for that one quote, that one topic, that one insight that exposes a challenge with incredible honestly. I can feel myself exhale when that moment happens. And to be honest, in most interviews, that feeling happens multiple times. When someone shares something so REAL, so honest, that I know that this will resonate with others.

How I review the material to glean key insights

As I said at the beginning of this post, all of these interviews are research for my book Dabblers vs. Doers. I have found that the act of sharing the interviews via blog and podcast has helped me better consider how stories from the interviews can be integrated into the book.

I transcribe the interviews myself, and I’ve found that this has a dual focus:

  1. Making it useful and accessible to others via a blog post and podcast.
  2. Reviewing the material for use in the book itself. It’s nice to do it days after the interview, instead of waiting months and doing this later during the writing process.

It is also really useful to see which interviewees and which topics resonate with my audience — those who listen to the podcast and read the blog post. That is the kind of real-time feedback that will only make the book stronger in the long run.

Okay, that is nearly 3,000 words on my research/interview process, and I still feel as though I have left stuff out!

Please let me know if you have advice on how to improve my process.

Thanks so much.