OPINION In retail media the right questions are more important than the right answers

14 Oct 2025

When it comes to Retail Media, becoming a better questioner is a skill that must be learnt, says Colin Lewis

What if the role of anyone working in Retail Media is not having the right answers, the right measurement, the right AdTech, but having the skill of asking the right questions?

Much of what we do in our daily work is ask questions: we probe others or probe information. But when was the last time you stopped to think about how you ask questions?

I was reminded of this while trying to work through a particularly difficult strategy discussion with a colleague. My first instinct throughout was to keep suggesting solutions, supported by what I thought was relevant data and insight.

The problem was that we were immediately jumping into ‘solution mode’ and simply reinforcing ideas that are already there – or worse, asking questions to which everybody knows the answer they want to hear. No new ideas, mindsets, or insights could possibly have been developed, and we all came away from the meeting irritated and frustrated.

What was at the root of our problem? We did not ask enough of the right questions.

Questioning is a skill you can develop

For some people, questioning comes easily. People who work in Retail Media are typically:

  • Passionate about Retail Media
  • Interested in being part of a new ‘wave’
  • Nosy and inquisitive (at least the good ones are!)

But most of us don’t ask enough questions, nor do we understand that asking the right questions can be far more valuable than leaping to an answer.

Every facet of the Retail Media industry can benefit from being more inquisitive:

  • Working in AdTech, you need better questions to ask your target Retail Media Networks if you want them to invest in your technology
  • Working at a Retail Media Network, you need better questions to ask your brand advertisers what they are looking for if you want to grab a larger share of their marketing budget
  • Working for a brand advertiser, you need better questions of your Retail Media Network and your media agency to ensure you are deploying your budget correctly.

How to become a better questioner

Few of us think of questioning as a skill that can be developed. Barristers, journalists and doctors are taught how to ask questions as part of their training. But not those of us working in Retail Media. Sure, we might know to avoid closed-ended questions that can be answered ‘yes’ or ‘no’ as these are of no value when it comes to developing new ideas and insights. 

My observation is that we want to be positive and tend to believe we are in the solution business: our first instinct is always to suggest a solution. Giving solutions may be the most efficient way to get things done, but it can often result in a short-term gain.

What’s the first step in becoming a better questioner?

The simple answer is ask more questions. Developing the skill of being a good questioner starts with simply asking more questions.

We have all seen the virtuosity of a great TV host asking questions from their guests that elicit more interesting responses.

The good news is that by asking questions, we naturally improve our emotional intelligence according to behavioural science research. This, in turn, makes us better questioners – a virtuous circle. 

You must develop a passion for asking questions and be genuinely interested in other people and what makes them tick. If not, all you will be doing is preparing the answer in your head while they speak, instead of listening.

Worse, you will be looking for evidence that confirms what you want to believe rather than putting yourself in the other person’s position.

Of course, the sheer number of questions is not the only factor in becoming a better questioner. Knowing how to ask the right questions is equally important. A ‘perfect’ question can make all the difference.

Is there such a thing as a beautiful question?

How do we go about asking the right question? Indeed, is there such a thing as a ‘perfect’ question? Author Warren Berger calls them ‘beautiful questions’ and defines them as “actionable questions that can begin to shift the way we perceive or think about something that can serve as a catalyst for change”.

What do these look like? Let’s call them ‘empowering’ questions as they encourage development as a thinker and problem solver. Berger uses the following examples:

‘Why’ questions are ideal for coming to grips with an existing problem, helping us think analytically and critically why the problem exists. ‘Why did this campaign work?’ could give much fresher insight than, ‘Let’s look at the data and see what it says’. 

James Dyson, inventor of all those amazingly designed vacuum cleaners, purportedly said “Why do vacuum cleaners have to have bags?” and created a whole new category and price point.

‘What if’ questions can be used to explore new ideas for possible improvements and seeing if we can tackle the challenge another way. It also challenges assumptions.

‘How’ questions come when it’s time to act on ideas. Questions that start ‘How might we…?’ have the potential outcome of transforming possibility into reality.

The future of Retail Media is about asking better questions

Author, entrepreneur and futurist Peter Diamandis says in the future it will not be about “what you know” but “the quality of the questions you ask” that will be most important.

If you want to grow an industry, there is no point in asking vanilla questions or parroting the same answers you can hear anywhere.

The real skill for those working in Retail Media is to use questions as a powerful tool to unlock the right evidence, to lead by asking rather than telling, and setting aside judgement.

Questions I think about

For me, I think we need to start asking better questions around topics like measurement or self-serve to uncover deeper truths. For example:

  • Why does (almost) every Retail Media panel and (almost) every article on Retail Media measurement talk about why it lacks measurement standards, even though all of the major IAB branches around the world have issued clear standards on onsite, offsite and instore?
  • Why do media channels like TV, radio, outdoor or newspaper never get asked about their measurement standards, their ROI or ROAS?
  • How come self-serve is asked for by brand advertisers, but Retail Media Networks find that the adoption by the same brand advertisers is poor?
  • How come trade marketing budgets – which have existed for years – never have to justify any form of ROI?
  • How can brand advertisers get to understand the power of Retail Media to build brands rather than just obsessing about broad reach?
  • How can Retail Media Network get advertisers to ask better questions instead of “what can I buy?” and move them to “why you should I buy it?”.

Questions other Retail Media leaders think about

I asked on social media what questions are on people’s mind about Retail Media.

Florian Clemens, Head of Tesco Media Strategy, Proposition & Measurement put out his list of questions on social media, drawing inspiration from Tesco and what he had seen at conferences:

  • How will media planners of the future balance going after 100 micro-level business challenges of “this mascara has growth opportunities with young professional women who shop at Tesco but don’t buy their beauty products there” when they really need to run a national plan?
  • How much will in-store data allow for granular retail media optimisation using detailed, live out-of-stock data – just like Amazon already stops your SpAds campaign when a brand is OOS?
  • Is talking about Brand versus Performance Marketing still a useful shorthand or no longer best practice?
  • How do we inject more creativity into Retail Media?

Paul Thomas of TSP asked this question:

  • Why do media and channels often face-off against each other, rather than uniting into one easily accessible, marvellous toolbox that can influence customer behaviour?

Ben Foulkes, Commerce Media Lead at Kevel asked these questions:

  • Do brands that outsource their media buying to agencies really need self-service or would they be happy with minimal effort and automated ROI for certain placements?
  • Is it better to improve targeting, or to invest in more interesting formats and creative execution?

Simon Swan, Digital Marketing & E-Commerce Director for Karo Brands asked these questions:

  • Where should the role of retail media sit in an organisation departmental set up?
  • Is Retail Media the bridge between brand versus performance teams?

I would encourage you to start creating your own list of questions rather than just following what you read on LinkedIn and hear in conferences. Write down your version of Warren Berger’s  ‘beautiful question’ and create your own‘actionable questions that can begin to shift the way we perceive or think about something that can serve as a catalyst for change’.

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