10 questions to ask when working with artists

Guidance for the head as well as the heart when working with creative talent

Welcome to late March on South Beach

Miami — home of the Dolphins, the Heat, maybe an MLS team; Scarface, Dexter, Ace Ventura; the gateway to the Americas.

It’s also home to Winter Music Conference (WMC), a slightly misleading name as a) I can count on one hand the number of people I know who have attended the actual conference, and b) winter is these parts is 80 degrees (not exactly Canada Goose weather).

For the uninitiated, WMC is a week-long event in late March consisting of pool parties, club nights, people-watching, networking, spring breakers, tricked-out cars, new music, sunburn, more pool parties, and the huge Ultra Music Festival.

In short, you probably wouldn’t want to bring your Mum along.


Breakfast time

During my WMC 2014 visit, I had a breakfast meeting one morning with a US-based music industry friend who I’ve known for several years. We’ve never done that much direct business together but have followed a similar path and ethos in our respective careers, so whenever we get together the conversation is always flowing from the get-go.

This time I wandered down to see him at the Mondrian Hotel, out of the glare and madness of the Collins Avenue hotels (I’ve never understood the appeal of paying $400+ a night to have a 12 hour party outside your window from 11am every day), to be greeted with a big welcome and a pre-paid large and tasty breakfast from my compadre — he was looking well; business was good.

I was wearing a slight hangover and mild sunburn (didn’t listen to my Mum’s advice), but after imbibing a small vat of filter coffee, we got chatting and conversation moved towards working with new talent.

Working with new people there’s often a lot of unknowns, particularly in a competitive business that also has large elements of gut instinct and passion involved. When it’s a new artist there’s a lot of investment involved — blood (sometimes), sweat (often), tears (before bedtime), and of course time and quite possibly money.

Therefore I feel it can be useful to have something to help guide the head as well as the heart.

During our chat, I was reminded me of an old note I made and never finished. At the time I wasn’t able to list the contents of this note verbatim to my breakfast partner, but he got the gist and we threw a few ideas around as to how it could tweaked to be a useful tool for everyone involved in creative business relationships.

This post is a much belated write-up of those ideas.


The Questions

I started using this list of questions when talking to prospective clients (usually artist managers, either by email, phone or in person); some people really didn’t like answering them, and some just didn’t answer them at all, but I found that I got a lot of value from the responses of those that did.

This list was created for my music booking work but with a little tweaking it could be used in a bunch of different scenarios.

I’ve made a few notes alongside some of the questions as to the reasoning for their inclusion.

1. Who is in the team and what is their experience?

(i.e. PR, Manager / Assistant, Label, Accountant, Lawyer, Publisher; but also other people who may be Brands, Advisors etc.)
An artist manager friend drilled this one into me — you’re not just taking on an artist, you’re taking on the whole team, and it needs to fit. You’ll probably know pretty quickly if it doesn’t fit.

2. Who take cares of the back-office work?

Never to be underestimated — if this stuff isn’t handled well it can create a lot of pain all round. The pain I have experienced here is broad and deep (especially when I was starting out), and definitely not for a pre-watershed article such as this.

3. What partnerships and affiliations are in place/planned?

Whether it’s brands, record labels, support gigs…leveraged partnerships can be hugely important. I’ll write more specifically about these another time.

4. Does the artist want to be famous?

This is my favourite one. I received answers that were either an instant and adamant Yes, an instant and adamant No, a very long pause for consideration before answering, or getting one answer before swapping for the other, then something in the middle. It sounds an obvious question but the answer will tell you a lot. It’s also worth noting there are different levels and perceptions of fame.

5. Who do they admire?

Which other artists and why? People in other fields? This can help both tactically and strategically. Often you hear about other artists they don’t want to be associated with too…

6. What do the team want from this relationship?

Money, love, friends, attention, long-term partner, short-term fling?

7. Is there any funding/investment in the artist?

Without anything here, it’s unfortunately tougher to succeed.

8. Who is the audience and what demographic?

Top-line social media numbers don’t cut it — genuine insight is what’s needed. Who are we actually talking to? Where are they? How engaged are they? What are their habits and interests?
Whilst a manager should know this stuff, it’s not their primary role or skill and I firmly believe there is a need for more business analysis/data science capability in the music business; not just in large companies nor as a bolted-on marketing function.

9. What makes this different to everything else out there?

In business-speak this would likely be referred to as a USP or Unfair Advantage. Hugely subjective in the music industry but still relevant. Star quality as I mentioned here is a good USP.

10. What is the happy ending to the story?

I like this one because it encourages visualisation- and it’s actually a lot harder to answer than you may think.

(Optional extras)

11. What do you want?

12. How will you know you’ve got it?

(These two are nabbed from an NLP video I saw online but are very good questions to ask, and are surprisingly difficult to answer, especially the second one; what are the things that will let you know you’ve got what you want?)


Whilst there’s not really any substitute for gut instinct and a personal relationship, I feel this little set of questions can really help accelerate a decision making process, and the strategy and plan that (hopefully) follows it.

I’d love to hear your ideas for ones to add, change or remove — you can let me know on Twitter if you like (@howardgray). For more thoughts and discussion about music, entertainment, business and technology, feel free to subscribe to my email list or join the Stems music industry meetup event I help organise.

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