Please steal these 42 useful random questions about planning advertising...

At a conservative estimate, 99% of the space in the apartment I share with my fiancée is taken up by my notebooks.

I live my life like Memento, except instead of filling my body with tattoos to help me remember stuff, I fill notebooks instead.

I've small moleskines for tidbits, quotes and random thoughts.

I've large classic hardbacks for writing out the key points from books.

I've notebooks dedicated solely to notes from the training courses I do.

I've A4 notebooks with random bits of scribbled business ideas spanning the last decade.

To an outsider, it looks like an absolute mess. To me, it's heaven. It's the first thing I'd save in a fire (besides the fiancée of course!).

I do it for two reasons.

My memory is absolutely awful. I forget most of what I read in the multiple books I consume at any one time. I read something random online and then spend 20 minutes trying to figure out where I saw it. Writing things down gives me comfort. It has the perfect calming effect on my information (and alcohol) addled brain's permanent anxiety over losing a good idea. Plus the actual discipline of writing things down long form also helps me cement stuff into the brain that wouldn't otherwise go in.

But there's another added benefit. I see every notebook I fill as a load of 'pre-emptive' work. It's all ideas, quotes, thoughts for prospective future briefs, blog posts, presentations and arguments that I might need to do in a hurry. These all help to shortcut my initial information search because I usually have something to hand.

Some of the smartest people in history have kept 'commonplace books' and I can see why. It's a permanent source of inspiration to flick back through, a host of random thoughts and ideas that I can pull out of the back pocket when I need to.

I'm firmly of the opinion that every planner or strategist worth their salt should have some sort of similar note-taking habit.

'Good planning questions'

At the back of one of the smaller moleskines I filled, I've kept about 10 pages free. This is my 'good planning questions' list.

It consists of an absolute goldmine of about 80 questions that I've come up with or stolen from others or appropriated from books, blogs or talks surrounding the planning process. It's an enormous treasure chest of good questions that helps get me unstuck and change my lens on a brief when I'm in the middle of it.

We've all been in the midst of a planning brain freeze, staring at a blinking cursor and unable to really get to the crux of a business/brand problem. It's a lonely feeling.

But it's not as lonely when I have the collective questioning power of all the best planner I've ever worked with in my pocket.

I love the 'behind the music, backstage access' that people like Mark Pollard and Julian Cole give into their working process. To me that's way more helpful than teaching people the theory. So I thought I'd share 20 of the questions that I've written down. I've broken these into a few categories, but I have about 7-8 different categories in my full list, including 'measuring effectiveness', 'understanding the client's personality', 'media habits & consumption', 'sense checking the strategy' etc etc.

Hopefully it helps you to start your own list.

(A quick note - some of these sort of bleed into multiple categories, you'll see what I mean.)

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Interesting questions on the audience

• Have you created a customer journey to show how people navigate the category and where media impacts? How much time do people spend ‘in market’ or ‘out of market’ for this product/service?
• Have you diagnosed the market and our brands position within it? Competitive analysis of offers, target audiences, advantages and disadvantages in the market. Where can we win? 
• What questions would we love to ask our audience if we met them in person in a coffee shop? (This can often be very different to the questions you'd ask in a research interview or survey.)
• What are some smart ways you could speak to the audience instead of spending on research? (Intercept them, sit in a coffee shop/restaurant and watch them, get into a Facbeook group with them, analyse how they speak about a topic etc.)
• Can you conduct some interesting research that nobody else is doing to give you an edge?
• How interested are they in the product, and how often do they buy it? (There's a big difference between making an irregular grudge purchase easier and making a regular pleasure purchase more frequent for example).

Interesting questions on the category & competitors

• What are the barriers to consumption? Taste, brand, availability, social proof? 
• Who also influences them to buy? (Mums & kids/teenagers, teens and peers etc.)
• What other brands in similar/different categories have faced these challenges?
• What are the cultural issues that our audience care about, and has anything big changed in their lives recently?
• Who are some of our audience's key influences?
• What advantages do competitors have that we need to steer clear of?
• Who or what is our enemy? Cultural tension, mindset, competitor etc?
• What are the key category entry points/usage occasions that our brand is focused around? (Think Domino's Saturday night in front of the TV or Galaxy chocolate relaxing in the bath, how, where, when, with what do people consume it?)
• What is the reality of decision making in this category? (Is it rational/emotional, long or short decision span?)
• Are there any other brands that are facing the same/similar issues that we could partner with?
• What category conventions should we avoid or subvert? (Beer, perfume, cars are all good examples of categories with strong 'seas of sameness'.)
• Where is the growth in this market coming from? (What products, categories etc are growing rapidly. Is it online or offline, wholesale or DTC?)
• Do the people we're talking to have an existing habit or behaviour that we can tie our desired response to? Can we create a Pavlovian response? (Meat free Mondays, burrito Fridays)
• Who are your most compelling competitors (not most successful, but most interesting to our audience)?

Interesting questions on the brand

• What does our brand's sales funnel look like? Where are people falling off?
• Is there anything about this brand that's truly differentiated in a functional way? Do people care about this?
• Are there any durable advantages/moats that the brand has that we can exploit? (History, community, quality stores, loyal workforce etc?)
• What non durable advantages can we lean on? (Current distribution levels, better online UX, we're small so we can afford to take more risk, we're Irish, we're not Irish.)
• What are the distinctive assets we can use or mess with?
• Is there anything in our brand's history that we can lean on to help with this?
• Who might be your enemies? Who are you contrasting against?  

Interesting question on selling the work

• Have you created a checklist of why this is on brief and why it will work? 
• Can you create an experiment to prove this is the right route?
• Where does the idea rank on the Heineken creative impact ladder? 
• Can you offer up a toolkit to the brand manager to sell this upwards/internally?
• Have you shown what brand actions could lead from this?
• What might people in the media/our CEO say about it?
• What would the press release be?
• What independent expert witness or 'informant' might help to prove your case? (Rob Campbell once hired prostitutes to make a point about car brands. No I'm not making that up.)
• Can you help creative to make a crude mock-up of the idea?

Interesting random questions

• What would a more dangerous version of this idea be? How could we really push the boundaries? How could we get onto the 6 One News/Late Late Show/Joe Duffy? (Oooh dangerous!)
• Is your proposition something that creatives can easily dramatise? Is it something that has enough legs for a creative platform idea?
• What marketing effectiveness/strategy models could we use to help here? (Sharp, Binet & Field, Wavemaker Momentum etc etc.)
• What do you want to avoid? What would a bad outcome look like? 
• Are there any media publishers, journalists, influencers or vloggers that would be relevant to this topic?
• Are there any Instagram hashtags, niche forums, blogs or real world fan clubs that are uniquely interested in this space?

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If you have anything to add, please drop me a comment below, and feel free to share with any planner types who might be interested.

Shane O'Leary

@shaneoleary1

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