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What I learned from 1,005.01 minutes of interviews during 2020!

There was a banker, a sailor, a surgeon, and a…I know, I know this sounds like the start of a terrible joke but actually, this is only a few from the list of high achievers that I have had the privilege of speaking with this year.

I am sure none of them would choose to describe themselves as such, but humility is certainly one of the common traits they all share.

Rather than focus on all the learnings from these interviews (of which there are many and that you are welcome to watch back from the recordings) I wanted to instead share my experience of developing from an okay-ish interviewer to well…someone who is now a bit better. Progression, not perfection after all.

As we hurtle towards the end of this crazy year I sat down and reflected on how I improved and what might be useful for others. Even if you have zero ambitions to be the next Joe Rogan, Larry David <insert your own blank here>, honing your interviewing craft is a really useful skill to deploy in both your personal and professional lives.

So, here we go – jump in the virtual interview chair and sit back and see what you could borrow from my experience. As the widely attributed T.S. Eliot quote goes (although this quote is disputed – there’s a research lesson within this!)  

“Immature poets imitate; mature poets steal; bad poets deface what they take, and good poets make it into something better, or at least something different.”

Or this similar quote, this time attributed to Picasso:

“good artists copy, great artists steal.”

My Top 5 Lessons:

  1. Do Your Homework

Whoever you are speaking to, is prepared to give up their valuable time for the interview, so you need to be respectful and make sure it’s a good experience for them.

There are a few obvious points here; check your facts, check your facts, and check them again! Don’t ask generic/obvious questions, like those awful interview questions we have all endured at some stage; if you had to be a superhero which one would you be?! It’s lazy and boring for listeners and interviewees.

Here’s an example of what I mean. I recently interviewed Darren Allaway a seasoned banker, who once upon a time was a professional basketball player. Even though I have met Darren previously this was something I was not aware of and figured might be an area not often talked about.

The obvious thing would have been to get into a chat about the Last Dance and NBA but instead as part of my broad research I was trying to link the current pandemic, NBA, and Darren’s outlook. Then I recalled the NBA made a bold move back in March to suspend the season, remember this was the early days of COVID-19. It was a smart and early call. So, I got into it and spent the best part of an hour digging into this and bingo found an article about the current NBA commissioner David Silver and how he acted quickly and decisively.

When I asked Darren what he thought about this it turned out that this not only appealed as a line of questioning on how leadership can be observed but Darren actually knows David!

I had also done some similar research on New Zealand’s Prime Minister Jacinda Ardern. Same theme, What Good Leadership Looks Like During The Pandemic but as my hedge nonetheless. Maybe Darren is not into basketball anymore, it could have been a big assumption from me but having two examples, gave weight to my discussion and hopefully was an angle not previously covered.

Another example is Pip Hare, I read on her blog about how she’s a fan of Aretha Franklin so dropped this into one of our q&a’s. It was a nothing comment but it showed some homework on my part and gave a little personal insight.


I write my roadmap out twice before every interview, once using good old paper and pen, like a stream of consciousness, and then once in a word doc. It’s partly a filtering exercise and partly the way I learn by going over things a few times. No one wants an overly scripted interview but equally bad is one where the interviewer is scrambling for questions.

My approach is to have a roadmap based on focus areas.

Most often this is career history, commercial awareness, leadership and management, and outlook. It helps me keep the rhythm, but I’m not obsessed with it, if we stick on one area because it’s interesting, I don’t panic about an even distribution of questions. It should after all be a free-flowing conversation.

One of my favorite interviewers Tim Ferriss is well known for his style of bouncing around between topics and going down rabbit holes. Yet if you listen closely you will notice common question areas and even a few standard rapid response questions at the end of each interview. This is a deliberate style choice; it sounds highly conversational but there is structure behind it.

But, alongside the roadmap get your q’s straight…

2. Ask Good Questions

My go-to here is Cal Fussman and his podcast Big Questions.

This is a learning that should transcend any situation. An issue with your kids/partner, a work scenario or simply maximising your opportunity when question time is limited. A good question is always a good thing.

To lift directly from Cal these are his hot takes on asking better questions (like the earlier quote, why not borrow from what works):

  • If you can make someone feel that you are genuinely curious about a subject that they are passionate about, there’s a good chance they will become comfortable and open up to you
  • If you’re not actively listening to the responses, then it really doesn’t matter how good your questions are
  • Imagine your follow-up questions as a shovel digging for gold. Sometimes the gold is well below the surface and you have to keep digging straight down to get to it
  • The word why? gently nudges someone to think more deeply about an area they already know. If the why? question is set in an area that the interviewee is passionate about, they will want to search for the answer to satisfy themselves
  • Prepare to improvise, this approach makes the back-and-forth spontaneous and builds on the sense of trust you’ve created because you’re involved in a conversation as opposed to an interview

3. Listen

Seems obvious right?! But if you’ve done your prep with 1. and 2. there’s a real danger that you become a question firing machine. STOP, don’t do it! Think of your prep questions as just that, they give you a prompt but often my best questions are those on the fly.

I make bullet notes as the conversation develops, but I’m conscious not to overdo it and be looking away constantly. You run the risk of distracting yourself from listening.

When in-person you need to hold and maintain eye contact as much as you can, even if it feels awkward. Have you noticed the head nodding? Again, this is key, stay interested, smile, relax the other person. See point 5.

When virtual, look directly at your webcam and create that engagement, interjecting is ok, it’s not a binary tennis match with q&a back and forth, so think conversation.

Remember your next question may depend on what you’ve just heard. Or it may depend on what you haven’t heard and are curious about.

4. Peel back the corporate façade

More often than not the focus of the interviews is connected to our professional lives, but that’s not to say the odd personal question is out of bounds. I already mentioned Pip Hare’s love of the Queen of Soul. When I spoke with Laurence Marshall from EquiLend we had to briefly chat football and his beloved West Ham. He talked about making decisions, so I flipped it back and asked him to predict the score that weekend. Fun, personal but also shows I was listening.

Asking somebody about a subject she or he loves makes them happy — for two reasons:

  • Many people feel they aren’t listened to enough…(or at all!). Your question may make them feel appreciated and respected
  • Many will be grateful that your question made them think about an area that they are passionate about – and they’ll generally want to dive deeper into that subject. The sense of comfort that you’re creating will lead to a sense of trust. Trust is what leads the way for your follow-up questions.

5. Be Interested

Maybe this seems so blindingly obvious it’s not worthy of being called a lesson, but it could be the most important of all.

Another of my favourite podcasters is Guy Raz who dives into the stories behind some of the world’s best-known companies. How I Built This weaves a narrative journey about innovators, entrepreneurs, and idealists and the movements they built.

I heard him being interviewed once and he spoke about how he often asks selfish questions (Tim Ferriss admits to the same).

What he meant by this was that by asking the questions you want to know; you will naturally be curious and interested. There’s also a likelihood others will want to know the same. If you like, you can play dumb, other than your research there’s little expectation for you to be the expert. If in doubt, ask the question you want to know about.

For example, I once asked Pip Hare about safety boats and rescue, perhaps a straightforward question but turns out not so obvious when you’re in the Southern Ocean and the only hope of rescue is from your fellow sailors.

I hope some of these points may prove useful next time you are in a meeting, talking with a friend, or just wanting to ask better questions.

I will leave you with this quote “The capacity to learn is a gift; the ability to learn is a skill; the willingness to learn is a choice” — Brian Herbert

Stay safe, stay curious and keep learning, here’s to 2021!

About this author

Matt Fotherby

Financial Markets, Compliance & Regulations

Matt Fotherby

Matt is our Founder and a passionate trainer.

His interest in education stems from his 10 years as an Account Executive looking after Global Hedge Fund and Asset Management clients. This led Matt to join the coveted Financial Markets Education team at UBS, a unique in-house education team that specialised in running a curriculum of financial market and product classes for both UBS employees and clients. Matt was responsible for building out the client offering; managing programs, creating content and teaching courses.

As financial markets entered a significant period of regulatory change Matt pivoted to take his client experience and market knowledge to focus on Regulations and Compliance topics.

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