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What Interviewing 100 Leaders Was Like

Personally interviewing 100 ­business ­people was always going to be a ­challenge. The first interview was ­released on 12th January 2016 and the 100th and final episode released on 18th June 2017, taking 523 days. It felt like doing a real-life MBA degree, so this book is all of those insights ­concentrated into an eight-hour read.

The Interview Selection Criteria

I wanted to find people in the midst of their business journey, find people who were navigating their own way, rather than those already at their destination. It meant finding people from a diverse range of industries, not just the telecoms, tech and media sector I knew well. New industries guaranteed my curiosity during the interview. However, that counted out a number of leaders I would have interviewed otherwise. These four selection criteria ensured the interview was insightful for a business audience.

Rule #1 Be Cat Curious

‘Am I curious about their personal journey and their industry?’ If I am, then the ­audience probably will be too, or at a ­minimum, my curiosity of their story will transfer to the ­audience. Being ‘as curious as a cat’ meant asking questions and then listening to their answers to follow up with another ­question that continued in that direction. I was ­fascinated by what it would be like to be a tattoo artist, as the society view of tattoos changed, through the eyes of John Wayne Roberts.

I wondered what the moments were that helped Richard Brimer turn photography into a successful career and I couldn’t help but want to know what the secret sauce was ­behind Classic Sheepskins success in ­prevailing through the closure of 21 of its competitors across Australasia. How did ­Maurice ­Callaghan do that and how had his son Kieran Callaghan taken over the mantle? It was curiosity in the invisible forces that shape us and the world we inhabit, that when made visible, makes for illuminating listening.

Rule #2 Explore New Industries

‘Is this an industry that is relatively new to me?’ If so, I am likely to ask questions that are interesting to students, businesspeople and the wider community, not just industry ­insiders. This meant interviewing ­sparingly in technology, telecoms and hospitality ­industries.

Rule #3 Talk To Current Traders

Talk to people trading today, so that the 100 interviews reflected a moment in time of how business was doing in the first part of the second decade of the 21st century. They could be just starting out like Lewis O’Donnell, who was still at high school when he started his 360-degree virtual reality company or it could be an industry veteran such as CEO Craig Hickson Progressive Meats sharing how he got started.

Rule #4 One Shot. One Take.

It’s one recording, one take, nothing gets left out. When Simply Indulgent’s Fiona ­Ritchie had a beauty customer walk in, she took the sale, then continued the interview without missing a beat. True entrepreneurship! The amount of trust these leaders placed in the process with their brand felt huge, ­because ­almost every interview was published ­without the need for time-consuming rounds of editing. There was the rare exception such as Stewart Financial Group’s CEO, Nick ­Stewart requiring a review for regulatory compliance but by in large, interviewees left the final product to my discretion. I placed more value on the flow than a highly edited radio-friendly version of what was discussed, so the interview lengths vary from twenty minutes up to over an hour. The interview seemed to wrapped up naturally. There were three additional guidelines that came about during the selection of interviewees, more out of necessity than planning.

Rule #5 Balance the Genders

Aim for a 50:50 gender balance. This came about at around interview 17 when someone called me out on Twitter about having only interviewed three women at that stage. This was a revelation as at that early stage I was going as fast as possible by asking people I had done business with or were friends. I ultimately got a 60:40 split male to female. 

Rule #6 Ask & Follow Up Recommendations

Ask and always follow up on ­interview recommendations. Early listeners and ­participants made trusted ­recommendations because they were part of the process. When you are undertaking a project where the ­concept is ­relatively new, you often find yourself ­explaining the ins and outs to people to ­allay fears or convey benefits and being referred eliminated that.

Rule #7 Interview In Person

Every interview took place face-to-face at their location of business. It introduced me to their world, surrounded by their ­operations, ­people, culture and all the things that were important to them. Interviewing Angus Thomson at Thomson Suits he was able to bring out the original handwritten sales book of suits from the companies first year of trading. Nick Story shared the performance of Hawke’s Bay Airport in the airport terminal board room as passenger planes were taking off and landing behind us. Ivan Yukich, CEO Demolition 1 could point to the demolition projects board and photographs of long ­removed buildings like the Napier Hospital and showed me the huge array of recovered items being recycled for another life on Trade Me. Greg & Rachel Hart took me on a tour of their Mangarara Farm and showed me the changes they had made to regenerate their farmland. I doubt the interviews would have flowed as easily if the chat took place in a recording studio.

The Interview Format

The format evolved and the questions ­refined throughout the project as the muscle ­memory got stronger at asking questions, but it wasn’t always that way. The first interview was as casual as you could get, sitting on a bench, ­opposite the Jiu-Jitsu training mats with ­Damian Smith. Damian was evangelising his future vision for New Zealand’s Jiu Jitsu team and that his Allegiance Academy would produce world-class athletes that would bring home medals to New Zealand.

The format remained casual up until ­interview 25. Up until then, it was easy for the ­conversation to flow freely because I knew the business owner or I was ­familiar with their business because I was either a ­customer or they were a client. Kiwitax were my ­accountants so I knew their special culture of family. Kent Baddeley was my first paying ­Tweet2eat member and Benny had opened Georgia,  stocking my favourite single origin coffee, Flight Coffee.

The casual format couldn’t continue because although the free-flowing style was easy to ­listen to, I missed asking questions that mattered to the audience. I felt that I could do better through deliberate preparation. When property tycoon Jonathan Wallace said yes, under the proviso that the interview would be done in twenty minutes, I wanted to ensure that every minute was packed with insights.

The interview was an early hit giving ­insight into how one of New Zealand’s most ­successful commercial property investors went about investing. I would later hear from many business owners how much they had learned during those 20 minutes, so ­business casual was swapped out. This meant ­having a script of areas I wanted to cover, a few key questions and then, be prepared to throw it all away and just go with the flow. If I could avoid looking at my notes during the ­interview, I would. 

Forming a hypothesis required ­researching the business and the owner to come up with a question that I couldn’t find an ­answer to, or an answer that I’d like to dig into ­further. I was curious how Farmyard Zoo came to be and what led Cliff & Dyan Comte to hand-rearing farm animals like Llama so that kids could get up close and personal with them in a way you wouldn’t see on a farm.

The One Common Denominator

This is the question I have been asked the most since the completion of the ­one-hundredth interview. The answer is more obvious than you’d expect. To be a business hero and lead a tribe of people through the unknown, it takes courage, determination, and passion and those are the character ­attributes of the people that came through from the questions and ­answers on the ­podcast. While every moment of ­courage shared was­different and the length of ­determination ­varied, the passion was ­unwavering. 

 

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