Insights: What I've Learned About Interviewing - Redux
Updated lessons from the years I’ve been interviewing people as a journalist and podcast host.
With my 250th episode of Looking Sideways on the horizon, and a rather large Substack milestone also looming, I’m sharing some classic old episodes and blogs from the archive, continuing with this piece on the art of interviewing, which I first published in February 2021.
I’ve taken the Insights paywall off, updated some details and imagery, and written a new intro. Let me know what you think once you’ve had a read 🙏
This is so on brand for me that, if you’re familiar with the name, it’ll probably sound like I’m making it up.
But the first person I ever ‘officially’ interviewed was none other than ‘Mr. Manchester’ himself: the late, great Anthony H. Wilson.
Tony was a mythical figure in 1980s Manchester, and the city fairly thrummed with stories about him.
He’d booked the Sex Pistols for his show So It Goes. He’d discovered Joy Division. He’d founded Factory Records, and was one of the people behind the Hacienda. He’d turned down The Smiths.
Tony was also a fixture on local TV, as presenter of Granada Reports, the regional news vehicle; and The Other Side of Midnight, his late-night music showcase.
Here he is introducing The Fall on what is one of my favourite ever clips, and which conveys pretty accurately Tony’s patented mix of suave broadcasting genius and pretentious silliness.
By the turn of the decade, Tony was also presenting Granada Upfront, a late Friday night topical discussion show to which I’d wangled a behind-the-scenes invite so I could interview him for my school magazine.
It was the 8th of June 1990, a balmy night, and my 14th birthday.
I can remember the date this clearly because it was also the evening Cameroon beat Argentina in the opening game of the 1990 World Cup (which, given they had Maradona on the pitch, and were the holders, counted as a proper upset).
At the time, Tony Wilson was probably the most famous local media personality in Manchester; certainly more famous than the youthful and as-yet unknown Steve Coogan, who warmed the audience up with a few impressions before the show went live (and who, a few years later, went on to portray Tony in Michael Winterbottom’s brilliant 24 Hour Party People):
So when at the end of the show I plucked up the courage to ask him a few questions for my story, I was basically terrified.
At this point, my main memory is of being greatly impressed by the way he seemed to use the word ‘fuck’ as a comma. I certainly can’t remember what I asked him, or what I subsequently wrote for the story, which I lost years ago.
But still: not a bad interview with which to open my official account as a journalist.
In the 35 years that have passed since that night, I must be getting close to a thousand interviews.
Some of them still stand out: like my first interview for Snowboard UK (above), with my pal Chris Moran, conducted in our shared digs in Sheffield in July 1995, the Monday after we’d all been to Glastonbury.
Or the time I interviewed a techno DJ at a rave in a Bosnian nuclear bomb shelter, while struggling to string two words together after being up for three days straight.
Or, during that same stint as a critic for a long-lost dance music magazine, the occasion I rendered Underworld’s Karl Hyde speechless with the question ‘You can’t kiss the sky with your tongue in your cheek: discuss’.
At least 300 of those interviews have been conducted in the last eight years, while I’ve been making Looking Sideways.
During that time, I’ve been fortunate indeed to take part in some truly memorable (and even life-changing, according to some of the many messages I’m fortunate enough to receive from listeners) conversations.
My own personal highlights?
Finally meeting and interviewing the great Kevin Naughton and Craig Peterson, the surf travellers who wrote the rulebook for the lifestyle I eventually ended up following as a journalist.
My conversation with Christina Koch in which we discussed metaphysics and the experience of living in space, is another definite highlight (not least as we’ve remained friends, and Christina is off to the moon!)
I have lovely memories of my first episodes with Sophie Hellyer and Easkey Britten, conducted during my first Ireland ‘omnibus’; a trip full of cold swims, empty surfs, and a lovely warm welcome from the local community.
And while it might be recency bias, I also greatly enjoyed my forthcoming episode 250 chat with Jeremy Jones, in which we discussed Jeremy’s changing attitude to risk, his views on activism, and the responsibility he feels as a public figure.
And yet, despite basically having three decades of experience to draw from, I still get the jitters; especially when I haven’t done one for a while, or when it’s a conversation recorded in front of an audience, something I’ve been doing more of in recent years.
It was one such scenario before a live event a few years ago that inspired me to write this piece.
I was heading to Stockholm to interview Chris Burkard for Db, and as the journey progressed, I realised I was feeling increasingly more nervous.
Which, when I thought about it rationally, seemed ridiculous: especially given how many interviews I’d conducted at that point, how much I’d learned in the 30-odd years I’d been pointing a dictaphone or mic at people, and how comfortable I actually am once the conversation starts.
It was a moment of semi-revelation. What if I just … gave myself permission not to get into a state about something I’m actually really good at?
So I did. And the interview was great, and I found myself actively enjoying the experience, and leaning into the fact that, at this point, there’s a hell of a lot of cognitive muscle memory and hard-earned experience at play.
A week or so later, I was asked to give a talk on the podcast for a company down in Cornwall. As the idea of interviewing was on my mind, I decided to make that the subject of the presentation, which was the beginning of what eventually turned into this piece.
It’s my attempt to distill what I’ve learned in the 30 years of interviewing people into a few key points. It’s also about how to think creatively, and understanding where intuition ends and preparation begins. It was fun to go over it once again. Once you’ve had a read, I’d love to hear your take.
1. Decide upon your editorial position
Is it an interview, a la Frost/Nixon? It is a Michael Parkinson or David Letterman style conversation, where bonhomie is used as a device to get the goods? Or is it an interrogation, where conflict is baked in from the beginning?
And what about your audience? How much work are you going to do on their behalf? Are you going to contextualise everything, or expect them to do some heavy-lifting of their own?
When it comes to guests, your chosen approach will naturally dictate the dynamic that occurs during your actual conversations. In my case, I decided early on to maintain a neutral editorial stance during my conversations, and allow my listeners to draw their own conclusions about my guests
On a couple of occasions, this has caused some disquiet among some listeners who were disappointed that I didn’t criticise a couple of guests who evinced some particularly questionable views. I understand this. But in my view, my job is to create an environment where people feel comfortable enough to reveal their true selves, (although this feedback certainly caused me to rethink who I interview, and how I approach certain topics).
This decision also impacts how your listeners will receive your conversation. Consider: if you’re lucky enough to develop an audience, as I’m fortunate enough to have done, your audience will quickly learn and accept your editorial position.
But until that happens (or, conversely, as your audience grows), your listeners will naturally be looking for a few reference points by which to orient themselves. The more work you expect them to do, the more likely it is that you’ll lose casual listeners. Hence why this initial decision is so important.
2. Get ready to think on three planes
Three planes? What on earth does that mean?
Fair question. It means, simply, that as an interviewer an engaged interview involves thinking on three distinct planes, a cognitive balancing act that requires the concentration of a poker player, the masking skills of an actor and the lateral thinking of a chess player. Well, kinda.
First and foremost, of course, you need to take care of the actual conversation itself, as you do with any dynamic. This means reading body language, taking cues from their reactions, establishing that all-important rapport, and so on.
Then there’s the second plane, which sees you adopt the role of an omniscient narrator as you steer the conversation from above, attempt to navigate its specific nuances, try to spot those unforeseen opportunities, work out when to shift topics, and all the other unseen calculations that help you shepherd the conversation effectively.
The third? That will be our old friend the ego, which requires a section all of its own….
3. Silence your inner critic
Ah, the inner voice of doubt, that inescapable harbinger of imposter syndrome that seems to exist only to sabotage your best creative efforts.
And, in my case, seems to appear just before I’m about to press record, or as whatever conversation I’m involved in is about to take a particularly interesting turn.
You know the one. “I hate my voice”. “This person doesn’t like me”. “That was a dumb question”. “I should have reacted differently there”. “I’m interrupting too often”. And so on.
It’s difficult to escape this ubiquitous inner dialogue. But it’s also worth remembering that it is literally in your head, and a product of your own insecurities.
The other interesting thing about the inner critic is how it evolves. When I began my podcast, it preyed on very immediate insecurities: the sound of my voice, whether anybody would like the show etc. etc.
Four years later, now that I’ve been lucky enough to build up an audience of my own, it has shifted to rather more privileged concerns. Why aren’t more people listening to this? That episode was amazing - why aren’t more people downloading it? Maybe I should do video?
The hard truth? Nobody else is thinking about this stuff. And - paradoxically - creative work of substance only happens when you stop worrying about what other people think.
So concentrate on the story you’re trying to tell, and the conversation at hand, and forget the elements you can’t control.
4. Be as curious as possible
The importance of filling your mind as an aid to creativity is well-worn territory. And an omnivorous curiosity is also crucial if you plan on interviewing people.
Why? Because - doh - people are into different stuff. And the more you can hold you own in as many different arenas as possible, the higher likelihood there is of you engineering an interesting conversation.
So read widely. Explore topical issues from as many sides as possible. Watch that watercooler TV show. Use your commute or dog-walk time to listen to audiobooks documentaries
Think of it like going to the pub. Don’t be the dullard who can’t wait to drone on for hours about his pet topic, unwittingly boring everybody to tears.
Instead, try to be the person who can switch easily and authoritatively between subjects depending on the company at hand.
It’ll make your job easier, give you the tools to quickly establish a rapport, and help keep things fresh and interesting for your listeners.
5. Do your research - but wear it lightly
Sure, you COULD go all Marc Maron, and make a virtue of the fact that you go into each interview gloriously unprepared.
But he gets away with it because…well, he’s Marc Maron, and his guests know what to expect when they appear on his show.
My take is a traditional one: correct preparation for any interaction is a sign of professionalism, conscientiousness and respect. We’ve all had interactions with unprepared people, and the impression it leaves is rarely positive.
This is one reason why it’s so important to specifically research each guest. But equally important is how how you choose to employ this research, particularly when it comes to anything remotely topical.
To my mind, your job here isn’t to research a topic in order to bolster your own opinion. Instead, you need to understand the terms of a topic, and the way other people are discussing it.
Take my conversation with skater Leo Baker, for example. Leo is the world’s most high profile trans none-binary skateboarder, so in preparing for this one I made sure I understood the mainstream consensus, the way Leo frames the issue, and the issues that they have had to tackle along the way.
Being aware of the framing of an argument in this way gives you the tools to enter potentially tricky territory with confidence - and give your guest the space to give their own opinion.
Seeking out this curiosity sweet spot will enable you to follow the threads of the conversation - and pull them with confidence.
6. Pull the threads
A good conversation takes on a life of its own, and as the interviewer your job is to help steward the chat in this direction.
This is where that targeted, lightly-worn research is important. And you can use it in another way, too: by having a few specific topics in mind that will lead to an interesting segment, and plan your conversation around these.
This is especially useful when you’re speaking to somebody who has been interviewed many times about their life and career. When I’m faced with this situation, I use my research to pick out a few threads that have been mentioned in other contexts but not really explored fully.
This worked especially well in my episode 160 chat with US street skating legend Cairo Foster. Cairo has been there, seen it, done it - and chatted about it on numerous podcasts.
In preparing for this one, I discerned a few themes that, thankfully, had been not fully explored during previous interviews: the importance of travel in shaping Cairo’s worldview; the impact of his itinerant upbringing as an international student; and his awareness of the specific masculine persona traditional skate culture demands of young men, and how this impacts them.
I then messaged Cairo explaining that this was my plan, so he’d know where I was coming from. In this way, he was able to think about these topics beforehand, and we were able to hit the ground running once I hit record.
7. Forget the script
Scripts can be helpful, of course. And I’ve certainly made use of them in the past, particularly when speaking to a guest from a completely unfamiliar background.
But relying too much on a list of scripted questions can have a detrimental effect on the conversation you’re trying to have. It can be a sign of nerves and inexperience, like when you watch an inexperienced public speaker cling to their notes like a drowning person to a life raft.
Ultimately, this lack of self-confidence will undermine the delicate rapport you’re trying to craft with both guest and listener.
There’s another issue, too: slavishly sticking to the script also affects your ability to seamlessly switch between topics. What do I mean by this?
Well, to keep your chat interesting you’ll need to spot the conversational openings that will enable you to shift things onto a different topic: and gracefully shepherd your guest in this direction.
This subtle segueing between topics is one of the key interviewing skills. Accomplished smoothly, the listener (and interviewee) doesn’t even realise its happening. Carried out clumsily, it ruins the flow of the conversation, as well as the listening experience.
As you gain more experience, you get better at handling this important aspect of the interviewing dynamic.
The other reason to be prepared to jettison your plan is simple: a good conversation takes on a life of its own, and you need to be prepared to let this happen naturally. Often, this can mean throwing that topic-based plan out of the window.
8. Trust your intuition
When a conversation does begin to spin off in a different direction (even one you might be uncomfortable with!) it’s important to go with it. For one thing, it’s a promising sign that your guest is beginning to relax and open up.
For another, these Rubicon moments present you with an opportunity to head down hitherto unexplored paths, and are usually a sign that the conversation is going in the right direction.
Recognising when this is happening, and embracing it, is a question of intuition. Essentially, you’re trusting your ability to lead the conversation, whichever direction it takes.
This is usually the most intimidating part of the interview, but also the most rewarding. It’s also when you’ll be thankful for the groundwork you’ve done beforehand, which is really what gives you the foundations to take a conversation in a new and unexpected direction.
9. Build a rapport
Unless you’re fortunate to be interviewing a friend, you must assume that a state of suspicion exists between you and your guest.
If your guest has a high profile, it’s highly likely that they’ve been had bad experiences with previous interviewers. Or they may be approaching your conversation with a clear agenda, or a message they want to get across.
If your guest isn’t used to being interviewed, they’re likely to be extremely nervous, and worried about your motives.
Your job as the interviewer is to analyse this three-dimensional battleground and come up with a strategy that will break this potential tension and put your guest at ease.
It’s actually much easier than it sounds, and I’ve found there are a couple of tried and tested techniques that work most of the time.
The first is to start speaking about absolutely anything - the weather, last night’s football score, whatever news story is doing the rounds that day. And then press record. That’s it. By the time they realise what’s going on, you’re five minutes in, they’ve forgotten it’s even an interview and the tension is broken.
The second is a little bit more - dare I say - manipulative and is really only necessary when you’re dealing with a time-poor, ego-rich guest who is erring soon the side of suspicion: shameless flattery.
By this, I don’t mean tell them how great their haircut is, or how much you like their trainers.
It needs to be subtler than that, and the way I’ve found most effective is to make it clear you’ve done your homework and paid them the respect of preparing correctly for the interview. Maybe it’s a passing reference to their latest work. Or bringing up a topic you know they’re passionate about.
When it works, this ice-breaking tactic is the first step in dismantling the emotional barriers and getting to the good stuff.
One sign that I know things are going well is when the subject unconsciously repeats back to me a word I’ve used previously in the conversation. Strange but true.
All that said…
10. Accept that things may not go as planned
Of course, this is all fine until things go wrong. As the famous old Mike Tyson quote puts it, everybody has a plan until they get punched in the face.
When things do go seriously off piste, the only thing you can really do is make the most of it
In my experience, curveballs come from two directions. The first is when, early on, a guest decides to try and ‘test’ you in some way, to make sure you’re worthy of their time and attention. Think Bob Dylan berating that hapless Time journalist in Don’t Look Now.
The second comes when the guest decides they’re not interested in participating and effectively downs tools. I’ve only had this happen twice, with surfer Alex Knost, who after 45 minutes decided he’d had enough and brought the interview to a close by whistling the Simpsons theme tune and walking.
Then there was the time I headed to Corey Smith’s studio in Truckee, only to draw the interview to a close after 25 minutes; my patience with Corey’s gnomic, elliptical meanderings quickly exhausted.
In these situations, there’s really not much you can decide whether to hold your nerve and see it through regardless, or bring the thing to a temporary close. In Alex’s case, I just released the whole thing as it was and made a virtue of it.
Now you’ve read the piece - what was your first creative job? How did it inform what you do now? I’d love to hear from you on this