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In advertising there actually is such a thing as a bad question – just ask Socrates...

By Pete Jackson | Head of strategy and insights



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September 9, 2022 | 7 min read

‘There’s no such thing as a bad question,’ we hear at school and in pitch meetings. But is it really true? Pete Jackson of Wasserman, who happens to also be a trainee psychologist, says not.

A pair of lips and a finger, making the 'shh' gesture

In pitches and brief responses, there are bad questions after all. Here’s how to avoid them / Kristina Flour via Unsplash

You’ve just left the meeting having received the big brief. Questions were asked, everyone smiled and you left.

A short time later you realize: you have no idea what this challenge is about, what the brand wants or why anyone should care. How did this happen?

Questioning a brief is often crowd-sourced among an army of colleagues, all told that ‘no question is a bad question.’ It can be frightening to challenge clients, as social pressures nudge us toward the safety of agreement. It can be easy to sleepwalk through meetings that feel cozy.

But this comfort causes discomfort in the long term when we try to answer a brand problem that we didn’t question thoroughly enough.

From this one misstep arise multiple problems: unclear creative briefs; inaccurate tenders; work that needs redoing; irrelevant talent searches; ambiguous feedback; misguided presentations; re-briefs; and more hours burned.

If you can relate to even half these issues, you know we don’t have time for this. You, dear reader, don’t have time for this. We must stop wasting time asking questions that aren’t about the core problem we’re trying to solve.

So yes – when taking a brief, there is such a thing as a bad question. But there’s hope. Better questions can be learned from applied psychology, particularly Socratic questioning. Techniques psychologists use to help clients develop new perspectives can guide us toward a deeper understanding of business challenges. Here are three simple questioning approaches:

1. Start at the heart

Socratic questioning focuses on the main concern. In business, that means using your time to focus on the problem: “What is the problem? For whom? Why is it a problem? Who is this not a problem for? How will we know when we’ve solved it?”

Too often we drift toward procedural questions: “What is your preferred deck template? Who do we send the invoice to? Do you have brand guidelines?” This can reflect the army of colleagues taken to briefings, each with their own agenda, and the objective of asking ‘any’ question to justify attendance at said meeting. This eats into the crucial time. Those questions may be helpful, but ask yourself if they could come later.

Key questions:

  • What is the problem you are facing?

  • Why is this a problem for your business?

  • When did this first become a problem?

2. Clarify understanding before you move on

The first follow-up question in most descriptions of Socratic questioning is a clarifying question. Summarize what you’ve heard or reflect it back to the client or partner, sometimes paraphrasing. “This is what I’m hearing. Am I getting this right?” or “Just to recap, is the real problem here..?”

The standard question fire hydrant creates pressure to hastily move on, placing more importance on getting through the list v using crucial face time to discuss the real problem, clarify understanding and build relationships with your client.

Summarizing or reflecting gives the client a chance to confirm your understanding. In hundreds of hours as a trainee psychologist, I have rarely had clients tell me: “Yes, that’s exactly what’s going on, you nailed it!” More frequently I experience: “Yeah that’s kind of it... but that reminds me I should tell you about X, Y and Z.”

Key questions:

  • Have I got this right?

  • It sounds like... [metaphor/paraphrase]

  • This is what I am hearing...

3. Question assumptions

I once sat in a meeting about a beer brand. The lead agency said they’d been briefed on an alcohol responsibility campaign encouraging people to drink less. On the second slide were the objectives: “Increase volume by X%.” I couldn’t help myself and questioned the incongruence.

“Good point,” replied the agency employee; “the client is reasoning that if people are convinced to drink less, they’ll want drinks to be higher quality and therefore we will benefit.”


The staggering mental gymnastics reminded me how fearful we can be of clients, bosses or stakeholders with power. But challenging assumptions helps everyone sharpen the problem. It saves headaches down the line (such as having to evidence volume growth from a ‘drink less’ campaign).

Key questions:

  • How did you arrive at this assumption?

  • If we assume [something different]... would that change anything?

  • Are we assuming Y here... and does that run counter to X evidence?

Socrates said: “The highest form of human excellence is to question oneself and others.” Questions shouldn’t be crowd-sourced mindlessly, or sprayed from a fire hydrant. It is a craft that can and should be honed. When implemented well, that craft saves us time and money, and sets us on the right course.

Pete Jackson is head of strategy at Wasserman EMEA and a soon-to-be chartered psychologist.

Marketing Agency Culture Business Leadership

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Wasserman is a global sports, entertainment, and lifestyle marketing agency with expertise in creating connections between brands, properties, talent, and consumers.

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